aspergillusone A

A member of the class of xanthones that is methyl (1S)-2,9-dihydro-1H-xanthene-1-carboxylate substituted by hydroxy groups at positions 2 and 8, a methyl group at position 6 and an oxo group at position 9. It has been isolated from the sea fan derived fungus Aspergillus sydowii.


A member of the class of indanones that is 1-indanone substituted at position 2 by bromo and [(4-methylphenyl)sulfonyl]methyl groups.


beta-bitter acid

An alicyclic ketone obtained by prenylation at positions 4, 6 and 6 of any 2-acylphloroglucinol. beta-bitter acids are well known for their contribution to the bitter taste of beer.


A member of the class of anthracenones that is 3,4-tetrahydroanthracen-1-one which is substituted by hydroxy groups at positions 2, 3, 6, 8 and 9, and a 2-oxopropyl group at position 3.


chloroprallethrin

A carboxylic ester obtained by formal condensation between the carboxy group of (1R,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid and the hydroxy group of (4S)-4-hydroxy-3-methyl-2-(prop-2-yn-1-yl)cyclopent-2-en-1-one.


yanuthone G

A class I yanuthone that is yanuthone F in which the hydroxy group attached to the epoxycyclohexenone ring has been converted into the corresponding beta-D-glucoside.


A 3-oxo steroid that has alpha configuration at position 5.


A 3-oxo-Delta(4) steroid that is B-norcholesterol in which the 3beta-hydroxy group has been converted to an oxo group and the double bond at position 5 has been moved to position 4.


ALGESTONE ACETONIDE

A cyclic ketal that is the 16alpha,17alpha-acetonide derivative of algestone.


A steroid saponin that is 6beta-hydroxytestosterone attached to a alpha-D-glucopyranosyl residue at position 6 via glycosidic linkage.


Any 3-oxo steroid that has beta- configuration at position 5.


ethyl 4-oxocyclohexanecarboxylate

An ethyl ester resulting from the formal condensation of the carboxy group of 4-oxocyclohexanecarboxylic acid with ethanol.


norethindrone acetate

A 3-oxo Delta(4)-steroid that is norethisterone in which the hydroxy group has been converted to its acetate ester.


viscumneoside I

A viscumneoside that is homoeriodictyol in which the hydroxy groups at the 7 and 4' positions have been converted to the corresponding beta-D-glucopyranoside and beta-D-apiofuranoside derivatives, respectively. Found in Viscum coloratum, an evergreen hemiparasitic plant whose stems and leaves are used in traditional Chinese medicine for the treatment of rheumatism.


7-hydroxyflavanone 7-O-beta-D-glucoside

A flavanone 7-O-beta-D-glucoside that consists of 7-hydroxyflavanone attached to a  beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.


xanthones

Any member of the class of  xanthenes based on a xanthone skeleton.


A 16-hydroxyprednisolone in which the hydroxy group at position 16 adopts alpha-configuration. It is a metabolite of budesonide found in human urine and plasma.


A 3-oxo-Delta(1) steroid containing an additional double bond between positions 4 and 5.


A C21-steroid that is cortisone in which the oxo group at position 20 is replaced by a hydroxy group.


DIHYDROISORHAMNETIN

A tetrahydroxyflavanone that is taxifolin in which the hydroxy group at position 3' is substituted by a methoxy group. It is a metabolite of taxifolin.


A steroid glucosiduronic acid that is (8xi,9xi,14xi)-androst-4-en-3-one carrying a glucosiduronic acid residue at position 17beta.


A C21-steroid that is pregnane which contains a double bond between positions 5 and 6 and is substituted by oxo groups at positions 3 and 20 as well as a hydroxy group at position 17.


A  3-oxo steroid  that is (22E)-24nor-cholesta-1,4,22-triene substituted by an oxo group at position 3. It is isolated from the Hainan soft coral Dendronephthya studeri.


A glucocorticoid that is prednisone in which the oxo group at position 20 is replaced by a hydroxy group. It is a metabolite of prednisone found in human urine.


plantagoside

A flavanone glycoside that is  (2S)-flavanone substituted by hydroxy groups at positions 5, 7, 4' and 5' and a beta-D-glucopyranosyloxy group at position 3' respectively.


yanuthone D

A class I yanuthone that is yanuthone E in which the secondary hydroxy group has been oxidised to the corresponding ketone. It is the only one of the sixteen yanuthones described up to 2015 to display strong antimicrobial activity.


fustin

A dihydroflavonol that is the 2,3-dihydro derivative of fisetin.


azanigerone B

An azaphilone that is the ester obtained by formal condensation of the carboxy group of 2,4-dimethylhexanoic acid with the tertiary hydroxy group of 7-hydroxy-3-(2-hydroxypropyl)-7-methyl-6H-2-benzopyran-6,8(7H)-dione.


viridicatumtoxin

A tetracycline-like polyketide antibiotic that is produced by several species of Penicillium and Aspergillus.


An androstanoid that is dehydroepiandrosterone carrying an additional hydroxy substituent at the 7beta-position. It is a metabolite of dehydroepiandrosterone.


A steroid sulfide consisting of 2,5-dioxo-1-pyrrolidinyl 6-{6-[3-(thiopropionyl)aminohexanoyl]amino}hexanoate having a progesterone-4-yl group attached to the sulfur.


A member of the class of furans that is 5-methyl-2-methylenefuran carrying additional oxo and hydroxy groups at positions 3 and 4 respectively.


A glucocorticoid that is prednisolone in which the oxo group at position 20 has been reduced to the corresponding beta-hydroxy group. It is a metabolite of prednisolone.


MINABEOLIDE 2

A  withanolide that is (22R)-22,26-epoxyergosta-1,4,24-triene substituted by oxo groups at positions 3 and 26 and an acetoxy group at position 18. Isolated from Paraminabea acronocephala, it exhibits anti-inflammatory activity.


A glucocorticoid that is prednisolone in which a double bond is introduced at position 6. It is a metabolite of prednisolone found in human urine.


An epoxide isolated from Streptomyces sp. E-1625. An inhibitor of interleukin-1beta converting enzyme (ICE), it acts as an anti-inflammatory agent and antibiotic.


clocortolone pivalate

The 21-O-pivalate ester of clocortolone. It is used for the relief of inflammatory and pruritic (itching) skin disorders.


yanuthone K

A class I yanuthone that is 5,6-epoxy-cyclohex-2-en-1-one which is substituted at positions 3, 4, and 6 by methyl, acetoxy, and trans,trans-farnesyl groups, respectively (the R,R,R stereoisomer). Isolated from the filamentous fungus Aspergillus niger, it shows antifungal activity towards the pathogenic yeast Candida albicans (IC50 = 17.5 +-3.9 muM).


tripteroside

A xanthone glycoside that is  norathyriol attached to a beta-D-glucopyranosyl residue at position 6 via a glycosidic linkage.


An  ergostanoid that is ergosta-1,4,24(28)-triene substituted by an oxo group at position 3. It is isolated from Hainan soft coral Dendronephthya studeri.


ROBUSTASIDE D

A beta-D-glucoside in which the anomeric position is substituted by a 4-hydroxyphenoxy residue and at position 6 by [(2E)-3-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)prop-2-enoyl]oxy residue. Isolated from Grevillea, it exhibits antimalarial activity.


(+)-tephrorin A

A  monomethoxyflavanone that is (2S)-7-methoxyflavanone substituted at position 8 by a tetrahydrofuran ring which in turn is substituted by geminal methyl groups at position 2, an acetoxy group at position 3 and a hydroxy group at position 5. Isolated from Tephrosia purpurea, it exhibits antineoplastic activity.


testosterone acetate

An androstanoid that is the acetate derivative of  testosterone.


3-oxo-Delta(4) steroid

A 3-oxo steroid conjugated to a C=C double bond at the alpha,beta position.


A 17beta-hydroxy steroid that is testosterone that contains an additional double bond between positions 6 and 7.


premithramycin A2'

A tetracenomycin that is an intermediate in the biosynthesis of the antitumour drug mithramycin by Streptomyces argillaceus.


deoxycortisol

A 3,20-dioxo steroid having the structure of cortisol but lacking one or more of its hydroxy groups.


demethyldeoxyspectinabilin

A polyketide that is deoxyspectinabilin in which the methoxy group at position 2 of the pyranone moiety has been replaced by a hydroxy group.


name: (17Z)-3,11-dioxopregna-4,17(20)-dien-21-oic acid methyl ester

description: A steroid ester that is methyl (17E)-pregna-4,17-dien-21-oate substituted by oxo groups at positions 3 and 11.


A fluorinated steroid that is pregn-4-ene substituted by a fluoro group at position 2, a methyl group at position 2 and oxo groups at positions 3, 11 and 20.


monomethoxyflavanone

Any methoxyflavanone that is flavanone substituted by a methoxy group.


A C21-steroid that is pregnane which contains a double bond between positions 5 and 6 and is substituted by oxo groups at positions 3 and 20.


HYPERXANTHONE C

A member of the class of xanthones that is 2,3,6,8-tetrahydroxyxanthone substituted by a 2-hydroxy-3-methylbut-3-enyl group at position 1. Isolated from the aerial parts of Hypericum scabrum, it exhibits cytotoxicity for human tumour cells.


ulipristal acetate

A 20-oxo steroid obtained by acetylation of the 17-hydroxy group of (11beta,17alpha)-17-acetyl-11-[4-(dimethylamino)phenyl]-3-oxoestra-4,9-dien-17-ol (ulipristal). A selective progesterone receptor modulator, which is employed as an emergency  contraceptive.


azanigerone F

An azaphilone that is 6H-2-benzopyran-6,8(7H)-dione carrying a 2-hydroxypropyl sunstyituent at position 3 as well as methyl and acetoxy substituents at position 7.


An oxaspiro compound that is 1-oxaspiro[4.5]deca-6,9-diene-2,8-dione carrying two additional tert-butyl substituents at positions 7 and 9.


testosterone 17-glucosiduronic acid

A steroid glucosiduronic that is testosterone carrying a glucosiduronic acid residue at position 17.


tephrocandidin B

A monomethoxyflavanone that is (2S)-flavanone substituted by a methoxy group at position 5, hydroxy groups at positions 7 and 4' and a 3-hydroxy-3-methylbut-1-en-1-yl group at position 8. It has been isolated from the aerial parts of Tephrosia candida.


ferroptocide

A triazolopyridazine that is 5,8-dihydro-1H-[1,2,4]triazolo[1,2-a]pyridazine-1,3(2H)-dione substituted by phenyl and (2S,3aS,4S,5S,7R,8S,8aS,9R)-7-[(chloroacetyl)oxy]-2,8a-dihydroxy-4,8,9-trimethyl-1-oxooctahydro-1H-3a,8-propanoazulen-5-yl groups at positions 2 and 6, respectively. It is a small molecule inhibitor of thioredoxin, a key component of the antioxidant system in cells. It induces rapid ferroptotic death in immortalized cancer cell lines and primary cancer cells from patients.


A beta-hydroxyketone that is 3-hydroxycyclopentanone in which a hydrogen at position 4 is replaced by a (1E)-4-hydroxy-4-methyloct-1-en-1-yl group and a hydrogen at position 5 is replaced by a 7-methoxy-7-oxoheptyl group.


A 17beta-hydroxy steroid that is testosterone bearing an additional hydroxy substituent at the 6beta-position.


An androstanoid that is dehydroepiandrosterone carrying an additional hydroxy substituent at the 7alpha-position.


A deoxycortisol that is 17xi-pregn-4-ene-3,20-dione substituted by a beta-hydroxy group at position 11 and an alpha-hydroxy group at position 17. It is a marker of virilizing adrenal hyperplasia caused by 21-hydroxylase deficiency.


A steroid acid comprising (20S)-20-hydroxypregn-4-en-3-one having a carboxymethyl group attached to the 20-hydroxy function.


platencin A3 methyl ester

A polycyclic cage that is the methyl ester derivative of platencin A3. It is isolated from Streptomyces platensis.


aureothin

A C-nitro compound that is (3Z)-3-[(2E)-2-methyl-3-(4-nitrophenyl)prop-2-en-1-ylidene]tetrahydrofuran which is substituted by a 6-methoxy-3,5-dimethyl-4-oxo-4H-pyran-2-yl group at position 5. It is isolated from the soil bacterium, Streptomyces thioluteus and exhibits antitumor, antifungal, and insecticidal activities.


(7R,8R)-alpha-diversonolic ester

A member of the class of xanthones that is methyl 2,3,4,9-tetrahydro-1H-xanthene-1-carboxylate substituted by hydroxy groups at positions 1, 2 and 8, a methyl group at position 6 and an oxo group at position 9 (the 1R,2R stereoisomer). It has been isolated from the sea fan derived fungus Aspergillus sydowii.


A 3-oxo Delta(1)-steroid that is androst-1-ene substituted by oxo groups at positions 3 and 17.


premithramycin A3'

A tetracenomycin that is an intermediate in the biosynthesis of the antitumour drug mithramycin by Streptomyces argillaceus.


TEMBOTRIONE

An aromatic ketone that is 2-benzoylcyclohexane-1,3-dione in which the phenyl group is substituted at positions 2, 3, and 4 by chlorine, (2,2,2-trifluoroethoxy)methyl, and methylsulfonyl groups, respectively. It is a post-emergence herbicide used (particularly in conjunction with the herbicide safener cyprosulfamide) for the control of a wide range of broad-leaved and grassy weeds in corn and other crops.


A steroid glucosiduronic acid that is epitestosterone in which the hydroxy hydrogen at position 17 has been replaced by a beta-D-glucuronyl residue.


(S)-donepezil

A 2-[(1-benzylpiperidin-4-yl)methyl]-5,6-dimethoxyindan-1-one that has S configuration.


aspergillusone B

A member of the class of xanthones that is methyl (1R)-2,3,4,9-tetrahydro-1H-xanthene-1-carboxylate substituted by hydroxy groups at positions 1, 2 and 8, a hydroxymethyl group at position 6 and an oxo group at position 9. It has been isolated from the sea fan derived fungus Aspergillus sydowii.


A steroid ester that is pregn-4-en-21-yl acetate substituted by a fluoro group at position 9, hydroxy groups at positions 11 and 17 and oxo groups at positions 3 and 20 respectively.


dihydroxyflavanone

Any  hydroxyflavanone carrying two hydroxy substituents.


colupulone

A beta-bitter acid in which the acyl group is specified as isobutanoyl.


A 17beta-hydroxy steroid that is testosterone in which the 4-5 double bond has been reduced to a single bond with unspecified configuration at position 5.


trinexapac-ethyl

An ethyl ester resulting from the formal condensation of the carboxy group of trinexapac with ethanol.


PESTALAMIDE A

A  pyranone that is (2S)-2-methyl-4-oxo-4-{[(4-oxo-4H-pyran-3-yl)carbonyl]amino}butanoic acid substituted by a benzyl group at position 6. It has been isolated from Aspergillus niger.


Any dihydroflavonol that has 2R,3R-configuration.


viscumneoside VI

A viscumneoside that is homoeriodictyol in which the hydroxy group at position 7 has been converted to the corresponding (6-O-acetyl)-beta-D-glucopyranoside. Found in Viscum coloratum, an evergreen hemiparasitic plant whose stems and leaves are used in traditional Chinese medicine for the treatment of rheumatism.


kadsurenin K

A neolignan with formula C20H22O5, originally isolated from Piper kadsura.


class II yanuthone

Any yanuthone whose 5,6-epoxycyclohex-2-en-1-one core is either unsubstituted at position 3 or is not attached to the 3-substituent by a carbon-carbon bond.


A steroid acid consisting of 6-[(3-thiopropionyl)amino]hexanoic acid having a progesterone-4-yl group attached to the sulfur.


clethodim

An oxime O-ether resulting from the formal conversion ot the acyclic keto group of 5-[2-(ethylsulfanyl)propyl]-3-hydroxy-2-propionylcyclohex-2-en-1-one to the corresponding oxime with subsequent O-alkylation of the oxime by an (E)-3-chloroallyl group. It is used as a selective postemergence herbicide for the control of annual and perennial grasses in numerous crops, including alfalfa, celery, clover, conifers, cotton, cranberries, garlic, onions, ornamentals, peanuts, soybeans, strawberries, sugarbeet, sunflowers, and vegetables; the (-)-enantiomer has been reported to be more active than the (+)-enantiomer.


An ergostanoid that is (22E)-ergosta-4,6,8(14),22-tetraene substituted by an oxo group at position 3. It has been isolated from the mycelia of Cordyceps sinensis.


A ring assembly that consists of two units of 4-hydroxy-3,4-dihydronaphthalen-1(2H)-one joined at their C-2 position. It has been isolated from the roots of Rubia yunnanensis.


A member of the class of furans that is (2E)-2-ethylidenefuran-3(2H)-one carrying additional hydroxy and methyl substituents at positions 4 and 5 respectively.


A 3-oxo Delta(1)-steroid with 5beta-configuration formed from 17beta-hydroxyandrosta-1,4-dien-3-one by reduction across the C4-C5 double bond.


The (S)-enantiomer of flavanone.


platensimycin A3 methyl ester

A polycyclic cage that is the methyl ester derivative of 7-hydroxy substituted  platensimycin. It is isolated from Streptomyces platensis.


A fucosyl oligoglycosylceramide where the oligosaccharide component is made up from four galactose, one galactosamine, three glucosamine, one glucose and one fucose residue.


(7R)-7-hydroxyoctanoic acid

An (omega-1)-hydroxy fatty acid that is octanoic acid in which the 7-pro-R hydrogen has been replaced by a hydroxy group.


calotropone

A 20-oxo steroid that is 17alpha-pregn-5-en-20-one substituted by a benzoyloxy group at position 12 and hydroxy groups at positions 3, 14 and 17 (the 3beta,12beta,14beta stereoisomer). It is isolated from the roots of Calotropis gigantea and displays inhibitory effects towards chronic myelogenous leukemia K562 and human gastric cancer SGC-7901 cell lines.


A cinnamate ester obtained by the formal condensation of the 1-hydroxy group of beta-D-glucopyranose with the carboxy group of trans-caffeic acid.


A ribose triphosphate that is alpha-D-ribose having a triphosphate group at position 5 as well as a methylphosphonate group at position 1.


(R)-fotemustine

A diethyl (1-{[(2-chloroethyl)(nitroso)carbamoyl]amino}ethyl)phosphonate that has R configuration.


phosphonic ester

A phosphonic acid derivative in which one or both OH groups have been esterified.


A ribose monophosphate that is alpha-D-ribose having a monophosphate group at position 5 as well as a methylphosphonate group at position 1.


NYGERONE A

A member of the class of 4-pyridones that is nigerone B in which the nitrogen of the carboxamide has been acylated by a (3S)-3-carboxybutanoyl group. It has been isolated from  Aspergillus niger ATCC 1015.


An alkenyl alcohol with a structure based on a C8 unbranched chain with the hydroxy group at C-2 and unsaturation at C-1-C-2. It is a major volatile compound present in many mushrooms and fungi.


An oct-1-en-3-ol that has S-configuration.


An oct-1-en-3-ol that has R-configuration.


A UDP-amino sugar having 2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucuronic acid as the amino sugar component.


cytidine 2'-phosphate

A cytidine phosphate compound having the phosphate group at the 2'-position.


(dihydroxyphenyl)propanoic acid

A monocarboxylic acid that is propionic acid carrying a dihydroxyphenyl substituent at position 3.


name: dTDP 1-ester with 2,6-dideoxy-L-erythro-hexopyranos-3-ulose


alpha-D-ribose 5-triphosphate

A D-ribose 5-triphosphate in which the ribose is in the furanose form and has alpha-configuration at the anomeric centre.


hydrogentungstate

A monovalent inorganic anion that consists of tungstic acid where one of the two OH groups has been deprotonated.


enamide

An alpha,beta-unsaturated carboxylic acid amide of general formula R(1)R(2)C=CR(3)-C(=O)NR(4)R(5) in which the amide C=O function is conjugated to a C=C double bond at the alpha,beta position.


pyrimorph

An enamide resulting from the formal condensation of 3-(p-tert-butylphenyl)-3-(6-chloropyridin-2-yl)acrylic acid with the amino group of morpholine. A fungicide developed in China, it shows high antifungal activity against diseases caused by Phytophthora infestans, Phytophthora capsici, Rhizoctonia solani, Peronophythora litchi, and Pseudoperonospora cubensis.


cinnamamides

An enamide which is cinnamamide or a derivative of cinnamamide obtained by replacement of one or more of its hydrogens.


A member of the class of indoles that is 5-chloro-4-(1H-indol-3-yl)-N-[(3R)-piperidin-3-yl]pyrimidin-2-amine in which the piperidine NH group is substituted by a 4-{[(2E)-4-(dimethylamino)but-2-enoyl]amino}benzoyl group. It is a first-in-class CDK12 and CDK13 covalent kinase inhibitor with IC50 of 158 nM and 69 nM, respectively.


CYSTODYTIN H

An  alkaloid ester obtained by formal condensation of cystodytin D with elaidic acid. It is isolated from the Okinawan marine tunicate Cystodytes dellechiajei and exhibits cytotoxicity against human epidermoid carcinoma KB cells.


CYSTODYTIN E

An alkaloid that is an enamide obtained by the formal condensation of tiglic acid with 6-(2-amino-1-hydroxyethyl)-4H-pyrido[2,3,4-kl]acridin-4-one. It is isolated from the Okinawan marine tunicate Cystodytes dellechiajei and exhibits cytotoxicity against human epidermoid carcinoma KB cells


CYSTODYTIN I

An alkaloid ester obtained by formal condensation of the hydroxy group of cystodytin E with the carboxy group of elaidic acid. It is isolated from the Okinawan marine tunicate Cystodytes dellechiajei and exhibits cytotoxicity against human epidermoid carcinoma KB cells.


CYSTODYTIN D

An alkaloid that is an enamide obtained by the formal condensation of 3-methylbut-2-enoic acid with 6-(2-amino-1-hydroxyethyl)-4H-pyrido[2,3,4-kl]acridin-4-one. It is isolated from the Okinawan marine tunicate Cystodytes dellechiajei and exhibits cytotoxicity against human epidermoid carcinoma KB cells.


trans-cinnamamide

The E (trans) isomer of cinnamamide.


acrylamides

An enamide which is acrylamide or a derivative of acrylamide obtained by replacement of one or more of its hydrogens.


cis-cinnamamide

The Z (cis) isomer of cinnamamide.


A cinnamate ester obtained by the formal condensation of the carboxy group of trans-cinnamic acid with the 9-hydroxy group of 7,9-dihydroxy-8,10-dimethyltrideca-2,4-dienamide (the 4R,5S,6R,7R,9E,11Z stereoisomer). It is obtained from the fermentation broth of Bacillus sp.YL-03709B and exhibits antifungal activity.


A hydroxy fatty amide ascaroside obtained by obtained by formal condensation of the 24-hydroxy group of (2E,24R)-24-hydroxy-N-(2-hydroxyethyl)-2-methylpentacos-2-enamide with ascarylopyranose (the alpha anomer). It is a metabolite of the nematode Caenorhabditis elegans.


A member of the class of indoles that is 1H-indole substituted by a 5-chloro-2-[3-(4-{[(2E)-4-(dimethylamino)but-2-enoyl]amino}benzamido)anilino]pyrimidin-4-yl group at position 3. It is a selective and potent covalent inhibitor of CDK7 that exhibits anti-proliferative effects in cancer cell lines.


ISARIOTIN F

An organic heterobicyclic compound that is a lactol isolated from the entomopathogenic fungus Isaria tenuipes and exhibits antimalarial and antineoplastic activities.


A benzoate ester obtained by the formal condensation of 6''-hydroxy group of quercetin 3-O-beta-D-galactopyranoside with the carboxy group of 4-hydroxybenzoic acid.


NSC 23766 trihydrochloride

A hydrochloride resulting from the formal reaction of NSC 23766 with 3 mol eq. of hydrogen chloride. An inhibitor of the signalling G-protein known as RAC1 (Ras-related C3 botulinum toxin substrate 1).


(S)-nomifensine

The S enantiomer of nomifensine.


dTDP-beta-D-fucofuranose

A dTDP-sugar having beta-D-fucofuranose as the sugar component.


METHYL OLEATE

A fatty acid methyl ester resulting from the formal condensation of the carboxy group of oleic acid with methanol.


fructosyllysine

A glyco-amino acid consisting of a D-fructosyl residue attached to the epsilon-amino group of L-lysine.


A C-nitro compound in which the nitro group is attached at C-4 of m-cresol.


A mononitrophenol that is 4-nitrophenol and its derivatives resulting from substitution of one or more of the hydrogens attached to the benzene ring by a non-nitro group.


An aryl sulfate that is 4-nitrocatechol in which the hydroxy group that is meta to the nitro group has been converted into the corresponding hydrogen sulfate. It is used (commonly as its dipotassium salt) as a chromogenic substrate for sulphatase.


glycerol 1-phosphoserine

A L-serine derivative consisting of L-serine having a 1-glycerophospho group attached to the side-chain hydroxy function.


glycerol 1-phosphodiester

A monoester of glycerophosphoric acid where R is an organyl group.


A glycerol 1-phosphoserine in which the glycero portion has R-configuration.


methyl green

An iminium salt composed of (4-{[4-(dimethylamino)phenyl][4-(trimethylazaniumyl)phenyl]methylidene}cyclohexa-2,5-dien-1-ylidene)(dimethyl)ammonium and chloride ions in a 1:2 ratio. A histological dye used to demonstrate nucleic acids by the Unna-Pappenheim stain, in conjunction with Pyronin Y.


A methyl ester resulting from the formal condensation of the carboxy group of 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-4-methylbenzoic acid with methanol.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (15Z,18Z,21Z,24Z)-triacontatetraenoic acid.


methylbenzene

Any alkylbenzene that is benzene substituted with one or more methyl groups.


A polymer composed of repeating 2-(N-acetyl-D-glucosaminyl)ribitol 1-phosphate units.


poly(ribitol phosphate)

A polymeric compound composed of repeating ribose-1-phosphate units.


A polymer composed of repeating 2-beta-D-glucosylribitol-1-phosphate units.


castasterone 23-O-alpha-D-glucoside

A brassinosteroid that is castasterone carrying an alpha-D-glucosyl residue at position O-23.


methyl undecenate

A fatty acid methyl ester of 10-undecenoic acid.


hemiacetal

A compound having the general formula RR'C(OH)OR'' (R'' =/= H).


bryostatin 2

A member of the class of bryostatins that is bryostatin 1 in which the acetoxy group has been replaced by a hydroxy group.


A spiro-epoxide with potent anticancer activity that lowers the mRNA levels of oncogenes and tumour supressor genes. It is isolated from Pseudomonas sp. no.2663.


myriaporone 3

A member of the class of oxanes isolated from the Mediterranean bryozoan Myriapora truncata and has been shown to exhibit inhibitory activity against murine leukemia cells.


concanamycin

Macrolide antibiotics first isolated from Streptomyces species. They possess an 18-membered lactone ring and a 6-membered hemiketal ring in which the hydroxy group at position 23 is glycosylated by 2-deoxy-beta-D-rhamnose.


A spiro-epoxide with potent cytotoxic activity against human tumour cells. It is isolated from Pseudomonas sp. no.2663.


lactol

Cyclic hemiacetals formed by intramolecular addition of a hydroxy group to an aldehydic or ketonic carbonyl group. They are thus 1-oxacycloalkan-2-ols or unsaturated analogues.


chaetoviridin D

An organic heterotetracyclic compound with formula C23H27ClO7 isolated from Chaetomium globosum. It is a diastereoisomer of chaetomugilin A (which has a significantly different optical rotation).


ossamycin

A  macrolide antibiotic that was originally isolated from the culture broths of Streptomyces hygroscopicus var. ossamyceticus.


A cyclic hemiketal isolated from the fermentation broth of Pseudomonas sp.no.2663. It displays potent cytotoxic activity against human tumour cells.


VERACEVINE

A cyclic hemiketal that is cevane that has an oxygen bridge from the 4alpha to the 9 position and is substituted by hydroxy groups at the 3beta, 4beta, 12, 14, 16beta, 17, and 20 positions.


A dicarboxylic acid comprising 2-hydroxy-2H-pyran having two carboxy groups located at the 4- and 6-positions.


A 24-membered macrolide antibiotic isolated from the fermentation broth of Streptomyces sp.NK154183. It exhibits antifungal and antitumour activity against the human colon adenocarcinoma.


hygrolidin

A macrolide consisting resulting from the formal lactonisation of the carboxy group of (2E,4E,6R,7S,8S,10E,12E,14S,15R,16S,17R,18S)-18-[(2R,4R,5S,6R)-4-{[(2E)-3-carboxyprop-2-enoyl]oxy}-2-hydroxy-5,6-dimethyltetrahydro-2H-pyran-2-yl]-7,15,17-trihydroxy-14-methoxy-2,4,6,8,10,16-hexamethylnonadeca-2,4,10,12-tetraenoic acid with the hydroxy group at position 15. It is active against SV40 tumour cells, and inhibits the growth of solid tumour-derived cell lines such as DLD-1 human colon cancer cells with increased cells in G1 and S phases.


cyclic hemiketal

A hemiacetal  having the structure R2C(OH)OR (R =/= H), derived from a ketone by formal addition of an alcohol to the carbonyl group. The term 'cyclic hemiketals', once abandoned by IUPAC, has been reinstated as a subclass of hemiacetals.


peloruside A

A macrolide that is a novel secondary metabolite isolated from a New Zealand marine sponge, Mycale hentscheli.


chaetoviridin B

An organic heterotetracyclic compound with formula C23H27ClO6 isolated from Chaetomium globosum. It exhibits antifungal activity against plant pathogenic fungi.


beta-D-fructopyranose

A D-fructopyranose in which the anomeric centre has beta-configuration.


aurafuron A

A polyketide that is 2,3-dihydrofuran substituted by hydroxy, methyl, oxo, methyl and (2S,3Z,5E,7R,8R,9E)-2,8-dihydroxy-7,9,12-trimethyltrideca-3,5,9-trien-1-yl groups at positions 2, 2, 3, 4, and 5, respectively. It is a cytotoxic natural product found in several myxobacteria species and inhibits the growth of some filamentous fungi.


hemiketal

A hemiacetal having the structure RR(1)C(OH)OR(2) (R, R(1), R(2) =/= H), derived from a ketone by formal addition of an alcohol to the carbonyl group.


avenasterol

A stigmastane sterol that is 5alpha-stigmastane carrying a hydroxy group at position 3beta and double bonds at positions 7 and 24.


chlorins

Dihydroporphyrin compounds where saturated carbon atoms are located at the nonfused carbon atoms of one of the pyrrole rings.


dihydroporphyrin

A porphyrin compound containing a porphyrin ring with one double bond fewer than in porphyrin itself.


ethyl octadecanoate

An octadecanoate ester obtained by formal condensation between the carboxy group of octadecanoic (stearic) acid and the hydroxy group of ethanol.


A member of the class of benzothiazoles that is 1,3-benzothiazole in which the hydrogen at position 2 has been replaced by a 5-fluoro-2-hydroxyphenyl group.


1-hexadecyl-sn-glycerol 3-phosphate

A 1-alkyl-sn-glycerol 3-phosphate in which the 1-alkyl group is specified as hexadecyl.


podecdysone B

A phytoecdysteroid that consists of 5beta-cholesta-8,14-dien-6-one bearing five hydroxy substituents at positions 2, 3, 20, 22 and 25.


N-acylneuraminic acid

Any neuraminic acid carrying an N-acyl substituent.


pyridinecarboxamide

A member of the class of pyridines that is a substituted pyridine in which at least one of the substituents is a carboxamide or N-substituted caraboxamide group.


picolinafen

A pyridinecarboxamide resulting from the formal condensation of the carboxy group of 6-(m-trifluoromethylphenoxy)picolinic acid with the amino group of p-fluoroaniline. A carotenoid biosynthesis inhibitor, it is used as a herbicide for the control of broad-leaved weeds in cereal crops.


florylpicoxamid

A carboxylic ester resulting from the formal condensation of the carboxy group of N-{[3-(acetyloxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine with the hydroxy group of (2S)-1,1-bis(4-fluorophenyl)propan-2-ol. It is a fungicide introduced by Dow AgroSciences for the control of a wide variety of pathogens such as Septoria spp, Powdery Mildews, Botrytis spp, and others in cereals, vines, fruits, nuts and vegetables.


A 1,3-thiazolium cation that is 5-(2-hydroxyethyl)-4-methyl-1,3-thiazole alkylated at the N3 position by a (2-methyl-4-oxo-1,4-dihydropyrimidin-5-yl)methyl group.


name: 2-[(2S,3R,6S)-2-(hydroxymethyl)-3-(1-oxopropylamino)-3,6-dihydro-2H-pyran-6-yl]acetic acid methyl ester


A 2-pyranone in which the hydrogens at positions 4 and 6 of 2H-pyran-2-one are replaced by hydroxy and 2-oxononadecyl groups respectively.


The (2S,3R)-stereoisomer of 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol.


(cyclohexylmethyl)pyrazine

A member of the class of pyrazines that is pyrazine in which one of the hydrogens is replaced by a cyclohexylmethyl group.


UDP-4-dehydro-6-deoxy-D-glucose in which the anomeric centre of the sugar component has alpha-configuration.


ganglioside GM2 (24:0)

A sialotriaosylceramide that is N-acetyl-beta-D-galactosaminyl-(1->4)-alpha-N-acetylneuraminosyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-N-acylsphingosine in which the acyl group on the sphingosine nitrogen is tetracosanoyl. A synthetic modification of the natural ganglioside GM2.


ent-dextilidine

An ethyl 2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate that has R configuration at the carbon bearing the phenyl group and S configuration at the carbon bearing the dimethylamino group. It is the enantiomer of dextilidine; the opioid analgesic tilidine is the racemate comprising equimolar amounts of dextilidine and ent-dextilidine.


DEXTILIDINE

An ethyl 2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate that has S configuration at the carbon bearing the phenyl group and R configuration at the carbon bearing the dimethylamino group. The opioid analgesic tilidine is the racemate comprising equimolar amounts of dextilidine and its enantiomer, ent-dextilidine. A prodrug, tilidine is converted by the liver to the active analgesic, nortilidine; virtually all of the opioid activity resides in the (1S,2R) isomer (i.e. the isomer derived from dextilidine).


cyproflanilide

A member of the class of benzamides that is benzene in which the hydrogens at positions 1, 2 and 3 are substituted by [2-bromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl]aminocarbonyl, fluoro, and (cyclopropylmethyl)(4-fluorobenzoyl)nitrilo groups, respectively. It is an insecticide developed by CAC Shanghai International Trading Co Ltd., China.


epsilon-metofluthrin

A carboxylic ester obtained by formal condensation between the carboxy group of (1R,3R)-2,2-dimethyl-3-[(1Z)-prop-1-en-1-yl]cyclopropane-1-carboxylic acid with the benzylic hydroxy group of [2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methanol.


broflanilide

A benzamide obtained by formal condensation of the carboxy group of 3-[benzoyl(methyl)amino]-2-fluorobenzoic acid with the amino group of 2-bromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-(trifluoromethyl)aniline. An insecticide that exhibits high larvicidal activity against Spodoptera litura and is effective against pests with resistance to cyclodienes and fipronil


CHLORFENAPYR

A member of the class of pyrroles that is 4-bromo-1H-pyrrole-3-carbonitrile which is substituted at positions 1, 2 and 5 by ethoxymethyl, p-chlorophenyl and trifluoromethyl groups, respectively. A proinsecticide used for termite control and crop protection against several insects and mite pests.


epsilon-momfluorothrin

A carboxylic ester obtained by formal condensation between the carboxy group of (1R,3R)-3-[(1Z)-2-cyanoprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylic acid with the benzylic hydroxy group of [2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methanol.


tralopyril

A pyrrole resulting from the N-dealkylation of the ethoxymethyl group of chlorfenapyr. It is the active insecticide of the proinsecticide chlorfenapyr.


N-arachidonoylphytosphingosine

A phytoceramide in which the N-acyl group is specified as arachidonoyl.


clofencet

A pyridazinone that is 1-(p-chlorophenyl)pyridazin-4-one which is substituted at positione 5 and 6 by carboxy and ethyl groups, respectively. It is used (particularly as the potassium salt, known as clofencet-potassium) as a chemical hybridisation agent for commercial hybrid seed production. It is not approved for use within the European Union.


cyclopyrimorate

A member of the class of pyridazine that is 3-chloropyridazine which has been substituted at positions 5 and 6 by (morpholin-4-ylcarbonyl)oxy and 2-cyclopropyl-6-methylphenoxy groups, respectively. A selective herbicide used to control broad-leaved and grassy weeds in cereals and rice.


flufenpyr-ethyl

An ethyl ester resulting from the formal condesnation of the carboxy group of flufenpyr with ethanol. It is used as a contact herbicide for the control of broad-leaved weeds. It acts as a protoporphyrinogen oxidase inhibitor, causing protoporphyrins to accumulate, damaging the membrane structure and cellular function. No longer approved for use in the European Union.


PYRAZON

A pyridazinone that is pyridazin-3(2H)-one substituted by an amino group at position 5, a chloro group at position 4 and a phenyl group at position 2.


NORFLURAZONE

A pyridazinone that is pyridazin-3(2H)-one which is substituted at positions 2, 4, and 5 by m-(trifluoromethyl)phenyl, chloro, and methylamino groups, respectively. A pre-emergence herbicide used to control grasses and broad-leafed weeds in a variety of crops. Not approved for use within the European Union.


flufenpyr

A ring assembly that is phenoxyacetic acid in which the phenyl group has been substituted at position 2 by chlorine, position 4 by fluorine, and position 5 by a 5-methyl-6-oxo-4-(trifluoromethyl)pyridazin-1(6H)-yl group. Its esters, particularly the ethyl ester (flufenpyr-ethyl), are used as contact herbicides for the control of broad-leaved weeds.


maleimides

Compounds containing a cyclic dicarboximide skeleton in which the two carboacyl groups on nitrogen together with the nitrogen itself form a 1H-pyrrole-2,5-dione structure.


CHLOROPHTHALIUM

A member of the class of phthalimides that is 4,5,6,7-tetrahydrophthalimide in which the nitrogen has been substituted by a p-chlorophenyl group. It is used as a herbicide.


A trisaccharide derivative in which a trisaccharide consisting of alpha-D-galactose, beta-D-galactose and beta-D-glucose residues linked sequentially (1->3) and (1->4), with the glucosyl residue at the reducing end being linked glycosidically to the terminal amide nitrogen of 19-maleimido-17-oxo-4,7,10,13-tetraoxa-16-azanonadecan-1-amide.


methoxypoly(ethylene glycol)-maleimide

A poly(ethylene glycol) derivative that is methoxypoly(ethylene glycol) in which the terminal hydroxy group has been converted to the corresponding 2-maleimidoethyl ether. Used particularly for the mPEGylation of free thiol groups in cysteine residues of proteins.


A member of the class of coumarins that is 2H-chromen-2-one substituted by 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl, methyl, and diethylamino groups at positions 3, 4 and 7, respectively. It is a thiol-reactive fluorescent dye.


FLUOROIMIDE

A maleimide that is substituted at positions 3 and 4 by chlorines and on the nitrogen by a p-fluorophenyl group. Previously used as a fungicide (now obsolete).


A member of the class of piperidines that is TEMPO carrying a maleimido group at position 4.


An N-hydroxysuccinimide ester derived from 4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid.


An aza-steroid that is 3-O-methyl-17beta-estradiol in which the 17beta-hydroxy group is replaced by a 6-(maleimid-1-yl)hexylamino group. An inibitor of phospholipase C.


An L-cysteine derivative that results when maleimide reacts with the thiol group of L-cysteine forming a thioether bond.


IPCONAZOLE

A member of the class of cyclopentanols carrying 1,2,4-triazol-1-ylmethyl, 4-chlorobenzyl and isopropyl substituents at positions 1, 2 and 5 respectively. Used to control a range of seed diseases in rice, vegetables and other, mainly non-food, crops.


A glycosylarabinose that is alpha-L-arabinopyranose in which the hydroxy group at position 3 has been converted into the corresponding beta-D-glucopyranoside.


A member of the class of piperidines carrying two aryl substituents (4-chlorophenyl and 4-(pyrazol-4-yl)phenyl) at position 4.


A synthetic chiral mycolic acid analogue comprising 3-hydroxypropanoic acid having a tetracosanyl group at position 2 and a further long-chain alkyl group containing cyclopropyl, methoxy and methyl functions attached at position 3.


mycolic acid analogue

Any 3-hydroxy fatty acid that is a synthetic analogue of a mycolic acid.


A chiral mycolic acid analogue comprising 3-hydroxypropanoic acid having a tetracosanyl group at position 2 and a further long-chain alkyl group containing two cyclopropyl rings at position 3.


A chiral mycolic acid analogue comprising 3-hydroxypropanoic acid having a tetracosanyl group at position 2 and a further long-chain alkyl group containing cyclopropyl and keto functions attached at position 3.


A chiral mycolic acid analogue comprising 3-hydroxypropanoic acid having a tetracosanyl group at position 2 and a further long-chain alkyl group containing cyclopropyl and methoxy functions attached at position 3.


A chiral mycolic acid analogue comprising 3-hydroxypropanoic acid having a tetracosanyl group at position 2 and a further long-chain alkyl group containing cyclopropyl and hydroxy functions attached at position 3.


rac-tamulosin hydrochloride

A racemate comprising equimolar amounts of tamulosin hydrochloride and its enantiomer, ent-tamulosin hydrochloride.


(RS)-mevalonate

A dihydroxy monocarboxylic acid comprising valeric acid having two hydroxy groups at the 3- and 5-positions together with a methyl group at the 3-position.


A secondary alcohol that is tridecane substituted by a hydroxy group at position 4.


A  1,3,4-oxadiazole substituted by a 2-chlorophenyl group at position 2 and a 5-methyl-2-thienyl group at position 5.


An oxime O-ether consisting of progesterone having an O-(carboxymethyl)oxime group at the 3-position and a hydroxy group at the 17alpha-position.


An oligosaccharide phosphate consisting of a linear chain of beta-D-mannose, N-acetyl-beta-D-glucosamine and N-acetyl-D-glucosamine residues all linked (1->4), to the mannose residue of which are also linked (1->3) and (1->6) respectively a 6-O-phosphono-alpha-D-mannosyl-(1->2)-alpha-D-mannosyl disaccharide unit and an alpha-D-mannosyl-(1->3)-[6-O-phosphono-alpha-D-mannosyl-(1->6)]-alpha-D-mannosyl branched trisaccharide unit.


A 3-hydroxy fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (3R)-3-hydroxytetracosanoic acid [(R)-3-hydroxylignoceric acid].


((13)C)carbon dioxide

A (13)C-modified compound that is carbon dioxide in which the carbon is present as its (13)C isotope.


(2S)-2-isopropylmalic acid

An optically active form of 2-isopropylmalic acid having S-configuration.


lificiguat

A member of the class of indazoles that is 1H-indazole which is substituted by a benzyl group at position 1 and a 5-(hydroxymethyl)-2-furyl group at position 3. It is an activator of soluble guanylate cyclase and inhibits platelet aggregation.


2-furoate ester

Any carboxylic ester where the carboxylic acid component is 2-furoic acid.


benzyl chlorides

Any benzyl halide containing a (chloromethyl)benzene skeleton.


p-nitrobenzyl chloride

A C-nitro compound that is nitrobenzene in which the hydrogen at position 4 is replaced by a chloromethyl group.


A lipid A where the free primary hydroxy group of lipid A has a branched nonasaccharide attached.


tertiary carboxamide

A carboxamide resulting from the formal condensation of a carboxylic acid with a secondary amine; formula RC(=O)NHR(1)R(2).


tolvaptan

A member of the class of benzazepines that is 2,3,4,5-tetrahydro-1H-1-benzazepine substituted by 2-methyl-4-(2-methylbenzamido)benzoyl, hydroxy, and chloro groups at positions 1, 5, and 7, respectively.


FURILAZOLE

A member of the class of oxazolidines that is 2,2-dimethyl-1,3-oxazolidine which is substituted by a dichloroacetyl group at position 3 and by a furan-2-yl group at position 5.


A member of the class of piperazines that is piperazine in which one of the nitrogens is substituted with a formyl group, while the other is substituted with a dichloroacetyl group. An antispermatogenic agent.


(S)-furilazole

A 2,2-dichloro-1-[5-(furan-2-yl)-2,2-dimethyl-1,3-oxazolidin-3-yl]ethanone that has (S)-configuration.


isoflucypram

A tertiary carboxamide resulting from the formal condensation of the carboxy group of 3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxylic acid with the amino group of N-[5-chloro-2-(propan-2-yl)benzyl]cyclopropanamine. It is a broad spectrum fungicide developed by Bayer that exhibits high efficacy against the major fungal diseases of cereal crops (wheat, triticale, rye, barley and oats).


A member of the class of benzotriazoles that is 1H-benzotriazole which is substituted by a 2-{[4-(2-methylpropanamido)phenyl][(thiophen-3-yl)methyl]amino}-2-oxoethyl group at position 1. It is a 3C-like protease inhibitor of SARS-CoV and bat coronavirus HKU4.


A sulfonamide resulting from the formal condensation of the sulfonic acid group of 2-oxo-1,2-dihydroquinoline-6-sulfonic acid with the primary amino group of (2R)-2-amino-N-(2-furylmethyl)-2-(2-methoxyphenyl)-N-(2-thienylmethyl)acetamide. OSMI-1 is a cell permeable inhibitor of O-linked beta-N-acetylglucosamine transferase (O-GlcNAc transferase, OGT).


tiapyrachlor

A member of the class of 1,3-thiazoles that is 1,3-thiazole substituted by pyridin-3-yl, chloro, and ethyl[3-(methylsulfonyl)propanoyl]amino groups at positions 2, 4 and 5, respectively. It is an insecticide developed by Corteva that has excellent activity against sap-feeding insects.


A member of the class of benzotriazoles that is 1H-benzotriazole which is substituted by a 2-oxo-2-{(4-propanamidophenyl)[(thiophen-3-yl)methyl]amino}ethyl group at position 1.  It is a 3C-like protease inhibitor of SARS-CoV and bat coronavirus HKU4.


An N-acylpiperidine that is N-acetyl 4-(1,3-thiazol-2-yl)piperidine in which the thiazole ring is substituted at position 4 by a 5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl group and in which one of the hydrogens of the acetyl group is replaced by a 5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl group.


A triazolopyridine that is 3H-[1,2,3]triazolo[4,5-b]pyridine substituted by a 4-{(3-chloropyridin-2-yl)[(3R)-piperidin-3-yl]carbamoyl}phenyl group at position 3. It is a potent inhibitor of PCSK9.


name: 2-amino-5-[diethylamino(oxo)methyl]-4-methyl-3-thiophenecarboxylic acid propan-2-yl ester


(R)-furilazole

A 2,2-dichloro-1-[5-(furan-2-yl)-2,2-dimethyl-1,3-oxazolidin-3-yl]ethanone that has (R)-configuration.


A monochlorobenzene that is benzene substituted by (chloroacetyl){2-oxo-2-[(2-phenylethyl)amino]-1-(thiophen-2-yl)ethyl}amino, chloro and methoxy groups at positions 1, 3 and 4, respectively. It is a covalent inhibitor of glutathione peroxidase 4 (GPX4) that induces ferroptosis in cells.


An isoquinolol that is 1,2,3,4-tetrahydroisoquinolin-4-ol in which the hydrogen of the secondary amine  is substituted by a 3-(3-hydroxy-3-methylbutyl)benzoyl group.


A member of the class of 1-benzothiophenes that is 3-chloro-1-benzothiophene-2-carboxamide in which the amide nitrogen is substituted by trans-4-(methylamino)cyclohexyl and 3-(pyridin-4-yl)benzyl groups. A smoothened (Smo)  receptor agonist that antagonizes cyclopamine action at the Smo receptor. Activates the Hedgehog signaling pathway in a Patched independent manner.


(R)-oxathiapiprolin

A 1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone that has R configuration at position 5 of the 4,5-dihydro-1,2-oxazole ring.


(S)-tolvaptan

The (S)-enantiomer of tolvaptan.


narlaprevir

An azabicyclohexane that is (1R,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane substituted by [(3S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl]aminoacyl and N-({1-[(tert-butylsulfonyl)methyl]cyclohexyl}carbamoyl)-3-methyl-L-valyl groups at positions 2S and 3, respectively. It is a hepatitis C virus (HCV) NS3/4A serine protease inhibitor (Ki = 6 nM) that is used for the treatment of chronic hepatitis C.


BUTACHLOR

An aromatic amide that is 2-choro-N-(2,6-diethylphenyl)acetamide in which the amide nitrogen has been replaced by a butoxymethyl group.


althiomycin

A peptide antibiotic isolated from soil and enteric bacteria. It is a protein synthesis inhibitor which exhibits antibacterial activity against both Gram-positive and Gram-negative bacteria.


DYSIDENIN

A secondary carboxamide resulting from the formal condensation of the carboxy group of (4S)-5,5,5-trichloro-N-methyl-N-[(3S)-4,4,4-trichloro-3-methylbutanoyl]-L-leucine with the amino group of (1S)-1-(1,3-thiazol-2-yl)ethanamine. It is a marine metabolite initially isolated from the sponge dysidea herbacea.


name: 4-[dimethylamino(oxo)methyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester


(S)-oxathiapiprolin

A 1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone that has S configuration at position 5 of the 4,5-dihydro-1,2-oxazole ring.


promysalin

A carboxylic ester resulting from the formal condensation of the carboxy group of (2S)-1-(2-hydroxybenzoyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid with the hydroxy group of (2R,8R)-2,8-dihydroxytetradecanamide. It is a metabolite isolated from Pseudomonas putida, , which resides in the rhizosphere of rice plants. The compound selectively inhibits the growth of Pseudomonas aeruginosa at low-micromolar concentrations.


A sulfone that is benzene substituted by [4-(dimethylcarbamoyl)phenyl]sulfonyl, chloro and [(2R)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]amino groups at positions 1, 3 and 4, respectively. It is a potent and non-ATP-competitive inhibitor of pyruvate dehydrogenase kinase 2 (PDHK2) with IC50 of 6.4 nM and exhibits glucose-lowering activity. Also inhibits PDHK1 at higher levels (IC50 = 36.8 nM).


A tertiary carboxamide resulting from the formal condensation between of the carboxy group of p-octylbenzoic acid with the amino group of 4-hydroxypiperidine.


A member of the class of pyrrolopyrazoles that is 2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole substituted by 2,4-difluorobenzyl and 4-(dimethylcarbamoyl)pyrimidin-2-yl groups at positions 2 and 5, respectively. It targets the AMPA receptor GluA2 subunit and exhibits potent effects in restoring neurological function and myelination in  mouse models for multiple sclerosis.


A tetradecanediol that is tetradecane carrying hydroxy groups at positions 1 and 5.


(±)-adrenaline

A catecholamine in which the aminoethyl side-chain is hydroxy-substituted at C-1 and methylated on nitrogen.


levisoprenaline

An optically active phenylethanolamine compound having an isopropyl substituent attached to the nitrogen atom.


noradrenaline

A catecholamine in which C-1 of the aminoethyl side-chain is hydroxy-substituted.


(+)-adrenaline

The S-enantiomer of adrenaline.


L-NOREPINEPHRINE

The S-enantiomer of noradrenaline.


(3R)-3,9-dihydroxynonanoic acid

A dihydroxy monocarboxylic acid that is 9-hydroxynonanoic acid in which the pro-R hydrogen beta to the carboxy group is replaced by a hydroxy group.


omega-hydroxy-medium-chain fatty acid

A omega-hydroxy-fatty acid with a chain length ranging from C6 to C12.


3,12-dihydroxylauric acid

A dihydroxy monocarboxylic acid that consists of lauric (dodecanoic) acid bearing two hydroxy substituents at positions 3 and 12.


(3R)-3,11-dihydroxyundecanoic acid

A dihydroxy monocarboxylic acid that is 11-hydroxyundecanoic acid in which the pro-R hydrogen beta to the carboxy group is replaced by a hydroxy group.


(3R)-3,12-dihydroxylauric acid

A dihydroxy monocarboxylic acid that is 12-hydroxylauric acid in which the pro-R hydrogen beta to the carboxy group is replaced by a hydroxy group.


(3R)-3,10-dihydroxydecanoic acid

A dihydroxy monocarboxylic acid that is 10-hydroxydecanoic acid in which the pro-R hydrogen beta to the carboxy group is replaced by a hydroxy group.


A nicotinamide dinucleotide consisting of NADP zwitterion lacking the 2'-phsopho group and having a (1R)-1-hydroxy-2-oxo-3-phosphonooxypropyl group at position 4 of the nicotinamide fragment.


pedunculosumoside D

A homoflavonoid glycoside that is 5'-prenylophioglonol attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It has been isolated from the whole plants of Ophioglossum pedunculosum.


trans-golgicide A

A racemate comprising equimolar amounts of (3aR,4R,9bS)- and (3aS,4S,9bR)-golgicide A. Commercially available golgicide A is a 10:1 mixture of cis- and trans-golgicide A; the (3aS,4R,9bR) stereoisomer is the most active.


2-hydroxyhenicosanoic acid

A 2-hydroxy fatty acid that is henicosanoic acid substituted by a hydroxy group at position 2.


A branched trisaccharide that is beta-D-Galp-(1->3)-beta-D-Glcp in which the hydroxy group at position 4 of the gluocopyranose moiety has been converted to the corresponding beta-D-glucopyranoside.


A tetrachlorophenol in which the chlorines are located at positions 2, 3, 4, and 6.


CYSTEINE

A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.


A cholestanoyl-CoA formed by thioester linkage between 3alpha,7alpha-dihydroxy-5beta-cholestan-26-oic acid and coenzyme A.


N-iodosuccinimide

A five-membered cyclic dicarboximide compound having an iodo substituent on the nitrogen atom.


An aminopiperidine that is piperidin-3-amine substituted by a [(prop-2-en-1-yl)oxy]carbonyl group at position 1.


A piperidinecarboxylate ester that is the methyl ester of 4-hydroxypiperidine-3-carboxylic acid.


A piperidinecarboxylate ester that is the methyl ester of 5-hydroxypiperidine-2-carboxylic acid.


A piperidinecarboxylate ester that is the methyl ester of 4-hydroxypiperidine-2-carboxylic acid.


hydroxy fatty acid

Any fatty acid carrying one or more hydroxy substituents.


A valeric acid derivative having an (R)-hydroxy substituent at the 2-position and an (S)-methyl substituent at the 3-position; one of 4 steroisomers of 2-hydroxy-3-methylpentanoic acid, generated by isoleucine metabolism. Found at significantly higher levels than normal in patients with maple syrup urine disease (MSUD).


resolvin D2

A member of the class of resolvins that is (4Z,8E,10Z,12E,14E,19Z)-docosahexaenoic acid carrying three hydroxy substituents at positions 7, 16 and 17 (the 7S,16R,17S-stereoisomer).


An (omega-1)-hydroxy fatty acid that is (14R)-14-hydroxypentadecanoic acid in which the 3-pro-R hydrogen is replaced by a hydroxy group.


2-hydroxyoctacosanoic acid

A 2-hydroxy fatty acid that is the 2-hydroxy derivative of octacosanoic acid.


(2R)-2-hydroxytetradecanoic acid

A 2-hydroxymyristic acid having 2R-configuration.


The S enantiomer of 3-hydroxy-3-methyl-2-oxopentanoic acid.


A docosanoid that is (9E,11E,13Z,15E,19Z)-docosapentaenoic acid carrying an epoxy group across positions 7 and 8 as well as a hydroxy substituent at position 17.  An intermediate of specialised proresolving mediators.


(11R)-11-hydroxylauric acid

An 11-hydroxylauric acid that has R configuration.


A hydroxyoctadecatrienoic acid that consists of 9Z,11E,15Z-octadecatrienoic acid bearing an additional 13-hydroxy substituent.


12,20-dioxoleukotriene B4

A member of the class of leukotrienes that is leukotriene B4 in which the hydroxy group at position 12 has been oxidised to the corresponding ketone and the methyl group at position 20 replaced by a hydroxy group.


(2Z)-2-hydroxypenta-2,4-dienoic acid

A 2-hydroxypenta-2,4-dienoic acid in which the double bond between positions 2 and 3 has Z- (trans-) geometry.


(R)-3-hydroxyoctanoic acid

The (R)-enantiomer of 3-hydroxyoctanoic acid; an important building block in the biomedical and pharmaceutical fields.


resolvin E2

A member of the class of resolvins that is (6E,8Z,11Z,14Z,16E)-icosapentaenoic acid carrying two hydroxy substituents at positions 5 and 18 (the 5S,18R stereoisomer).


(3R)-3,22-dihydroxybehenic acid

A dihydroxy monocarboxylic acid that is behenic acid (docosanoic acid) in which the pro-R hydrogen at position 3 and and one of the hydrogens of the terminal methyl group are replaced by hydroxy groups.


3,18-dihydroxyoctadecanoic acid

A dihydroxy monocarboxylic acid that consists of octadecanoic (stearic) acid bearing two hydroxy substituents at positions 3 and 18.


β-L-hydroxybutyric acid

The S-enantiomer of 3-hydroxybutyric acid; a normal human metabolite, that has been found elevated in geriatric patients remitting from depression.


2-hydroxyheptanoic acid

A monohydroxy fatty acid that is heptanoic acid with a hydroxy group substituted at position C-2.


(13R)-13-hydroxymyristic acid

An (omega-1)-hydroxy fatty acid that is myristic acid in which the 13-pro-R hydrogen is replaced by a hydroxy group.


A polyunsaturated fatty acid that is (4Z,9E,11E,13Z,15E,19Z)-docosahexaenoic acid having an epoxy group across positions 7 and 8 as well as a hydroxy substituent at the 17S-position.


A dihydroxydocosahexaenoic acid that is (4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoic acid in which the two hydroxy substituents are located at the 14S- and 21R-positions.


omega-hydroxynonacosanoic acid

A omega-hydroxy fatty acid that is nonacosanoic acid substituted by a hydroxy group at position 29.


DiHOME

A hydroxy fatty acid obtained by formal dihydroxylation across one of the double bonds of any octadecadienoic acid.


hydroxydocosapentaenoic acid

A docosanoid that is any docosapentaenoic acid carrying a single hydroxy substituent on its carbon chain.


A dihydroxydocosapentaenoic acid (DiHDPE) that is (7Z,10Z,13E,14E,19Z)-docosapentaenoic acid carrying two hydroxy substituents at the 16 and 17-S positions. It is an intermediate of specialised proresolving mediators.


9-hydroxylauric acid

A hydroxy fatty acid comprising lauric acid carrying a single hydroxy substituent at position 9.


2-hydroxy-4-methylvaleric acid

A valeric acid derivative having a hydroxy substituent at the 2-position and a methyl substituent at the 4-position; an alpha-hydroxy analogue of leucine. A bacterial metabolite, it has also been isolated from amniotic fluid, was found in a patient with dihydrolipoyl dehydrogenase deficiency and is present in the urine of patients with short bowel syndrome.


aspirin-triggered resolvin D1

A member of the class of resolvins that consists of docosa-4Z,9E,11E,13Z,15E,19Z-hexaenoic acid carrying three hydroxy substituents at positions 7, 8, and 17 (the 7S,8R,17S-stereoisomer).


(19R)-19-hydroxyicosanoic acid

An (omega-1)-hydroxy fatty acid that is arachidic acid acid in which the 19-pro-R hydrogen is replaced by a hydroxy group.


leptomycin A

A leptomycin having all-trans double bonds and a seventh methyl substituent at position 17.


aspirin-triggered resolvin D5

A member of the class of resolvins that is (5Z,8E,10Z,13Z,15Z,19Z)-docosahexaenoic acid carrying two hydroxy substituents at positions 7 and 17 (the 7S,17R-stereoisomer).


hydroxydocosahexaenoic acid

A long-chain polyunsaturated fatty acid that is any docosahexaenoic acid bearing a single hydroxy substituent. An oxidation product of docosahexaenoic acid metabolism.


(2E,7R)-7-hydroxyoct-2-enoic acid

An (omega-1)-hydroxy fatty acid that is (2E)-oct-2-enoic acid in which the hydrogen at the 7-pro-R position is replaced by a hydroxy group.


A 13-HODE in which the stereocentre at position 13 has S-configuration.


HODE

Hydroxy-octadecadienoic acids, formed in mammalian cells from the corresponding hydroperoxy compounds (HPODEs).


A monounsaturated fatty acid that is (7Z)-heptadec-7-enoic acid which is substituted by a hydroxy group at position 14 and by oxo groups at positions 10 and 13.


aspirin-triggered resolvin D6

A member of the class of resolvins that is (5E,7Z,10Z,13Z,15E,19Z)-docosahexaenoic acid carrying two hydroxy substituents at positions 4 and 17 (the 4S,17R-stereoisomer).


An HODE (hydroxyoctadecadienoic acid) in which the double bonds are at positions 9 and 11 (E and Z geometry, respectively) and the hydroxy group is at position 13 (with S-configuration).


9,10-dihydroxyoctadecanoic acid

A hydroxy-fatty acid formally derived from octacecanoic (stearic) acid by hydroxy substitution at positions 9 and 10.


An optically active form of 6-hydroxy-3-isopropenylheptanoic acid having (3S,6R)-configuration.


(2E,17R)-17-hydroxyoctadec-2-enoic acid

An (omega-1)-hydroxy fatty acid that is (2E)-octadec-2-enoic acid in which the 17-pro-R hydrogen is replaced by a hydroxy group.


resolvin D4

A member of the class of resolvins that is (6E,8E,10Z,13Z,15E,19Z)-docosahexaenoic acid carrying three hydroxy substituents at positions 4, 5 and 17 (the 4S,5R,17S-stereoisomer).


A hydroxydocosahexaenoic acid that is (4Z,9E,11E,13Z,15E,19Z)-docosa-4,9,11,13,15,19-hexaenoic acid carrying an epoxy group at position 7S and a hydroxy group at position 17R. It is a metabolite of docosahexaenoic acid, and serves as a precursor to D-resolvins.


13-hydroxytetradecanoic acid

An (omega-1)-hydroxy fatty acid that is myristic acid in which one of the methylene hydrogens at position 13 is replaced by a hydroxy group.


A dihydroxydocosapentaenoic acid (DiHDPE) that is (8Z,15E,19Z)-docosa-8,10,13,15,19-pentaenoic acid carrying two hydroxy substituents at positions 7 and 17. An intermediate of specialized proresolving mediators


aspirin-triggered resolvin D2

A member of the class of resolvins that is (4Z,8E,10Z,12E,14E,19Z)-docosahexaenoic acid carrying three hydroxy substituents at positions 7, 16 and 17 (the 7S,16R,17R-stereoisomer).


(9Z)-17-hydroxyoctadec-9-enoic acid

An (omega-1)-hydroxy fatty acid that is (9Z)-octadec-9-enoic acid (oleic acid) in which a hydrogen at position 17 has been replaced by a hydroxy group.


HOME

Any octadecenoic acid bearing a single hydroxy substituent.


A polyunsaturated hydroxy fatty acid that consists of (7Z,10Z,14E,16Z,19Z)-docosapentaenoic acid bearing a single hydroxy substituent at the 13R-position.


hydroxyoctadecanoic acid

A hydroxy fatty acid that is ocatadecanoic acid (stearic acid) in which the aliphatic chain has been substituted by one or more hydroxy groups.


(3R)-3-hydroxy fatty acid

A 3-hydroxy fatty acid in which the carbon at position 3 has R configuration.


(3R,12R)-3,12-dihydroxytridecanoic acid

An (omega-1)-hydroxy fatty acid that is (12R)-12-hydroxytridecanoic acid in which the 3-pro-R hydrogen is replaced by a hydroxy group.


(S)-2-hydroxybutyric acid

An optically active form of 2-hydroxybutyric acid having (S)-configuration.


7-oxoresolvin D2

A member of the class of resolvins that is resolvin D2 in which the 7-hydroxy group has undergone formal oxidation to the corresponding ketone.


A omega-hydroxy-fatty acid with a chain length ranging from C23 to C26.


A hydroxydocosahexaenoic acid that consists of (4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoic acid bearing an additional 13-hydroxy substituent.


An (omega-1)-hydroxy fatty acid that is (20R)-20-hydroxyhenicosanoic acid in which the 3-pro-R hydrogen is replaced by a hydroxy group.


(3R,21R)-3,21-dihydroxybehenic acid

A dihydroxy monocarboxylic acid that is behenic acid (docosanoic acid) in which the pro-R hydrogens at positions 3 and 21 are replaced by hydroxy groups.


(6S)-6-hydroxyheptanoic acid

A 6-hydroxyheptanoic acid that has S configuration at the chiral centre.


resolvin T3

A docosanoid that is (9E,11E,14E,16Z,19Z)-docosapentaenoic acid carrying three hydroxy substituents at positions 7, 8 and 13.


(S)-3-hydroxyoctadecanoic acid

A 3-hydroxyoctadecanoic acid in which the chiral centre has S configuration.


An epoxy fatty acid that is (6E,8E,10Z,13Z,15E,19Z)-docosa-6,8,10,13,15,19-hexaenoic acid which is carrying an epoxy group at position 4S and a hydroxy group at position 17R. It is a metabolite of docosahexaenoic acid that can be converted to a D-resolvin.


(12R)-12-hydroxytridecanoic acid

An (omega-1)-hydroxy fatty acid that is tridecanoic acid in which the 12-pro-R hydrogen is replaced by a hydroxy group.


(R)-2-hydroxybutyric acid

An optically active form of 2-hydroxybutyric acid having (R)-configuration.


(R)-17-hydroxyoctadecanoic acid

An (omega-1)-hydroxy fatty acid that is octadecanoic acid (stearic acid) in which the 17-pro-R hydrogen is replaced by a hydroxy group.


resolvin T2

A docosanoid that is (8Z,10E,14E,16Z,19Z)-docosapentaenoic acid carrying three hydroxy substituents at positions 7, 12 and 13.


3-hydroxyhexacosanoic acid

A 3-hydroxy fatty acid that is hexacosanoic (cerotic) acid substituted at position 3 by a hydroxy group; a component of bacterial lipopolysaccharides.


(3R,16R)-3,16-dihydroxymargaric acid

An (omega-1)-hydroxy fatty acid that is (16R)-16-hydroxymargaric acid ((16R)-16-hydroxyheptadecanoic acid) in which the 3-pro-R hydrogen is replaced by a hydroxy group.


A hydroxyicosapentaenoic acid that consists of 6E,8Z,11Z,14Z,17Z-icosapentaenoic acid with the hydroxy group located at position 5.


(16R)-16-hydroxymargaric acid

An (omega-1)-hydroxy fatty acid that is heptadecanoic acid in which the 16-pro-R hydrogen is replaced by a hydroxy group.


26-hydroxyhexacosanoic acid

The omega-hydroxy fatty acid obtained by hydroxylation at position 26 of hexacosanoic acid.


13-hydroxyoctadecanoic acid

A hydroxyoctadecanoic acid in which the hydroxy substituent is located at position 13.


2-hydroxy-3-methylhexadecanoic acid

A branched, alpha-hydroxy fatty acid comprising a C16 chain carrying a methyl branch at position 3.


A hydroxydocosapentaenoic acid that is (4Z,7Z,10Z,12E,16Z)-docosapentaenoic acid in which the hydroxy group is located at the 14S-position. An intermediate of specialised proresolving mediators


2-hydroxypalmitoleic acid

A 2-hydroxy fatty acid that is (9Z)-hexadecenoic acid which is substituted by a hydroxy group at position 2.


2-hydroxytricosanoic acid

A 2-hydroxy fatty acid that is tricosanoic acid substituted by a hydroxy group at position 2.


resolvin E3

A member of the class of resolvins that is (5Z,8Z,11Z,13E,15E)-icosapentaenoic acid which is substituted at positions 17 and 18 by hydroxy groups (the 17,18S stereoisomer).


A 12-HEPE that consists of (5Z,8Z,10E,14Z,17Z)-icosapentaenoic acid in which the 12-hydroxy group has S-configuration.


An octadecanoid that is 9,10-epoxy-(12Z)-octadecenoic acid carrying an additional hydroxy substituent at position 18.


An (omega-1)-hydroxy fatty acid that is (2E)-heptadec-2-enoic acid in which the 16-pro-R hydrogen is replaced by a hydroxy group.


2-hydroxyhexacosanoic acid

A very long-chain fatty acid that is hexacosanoic (cerotic) acid substituted at position 2 by a hydroxy group.


A (omega-1)-hydroxy fatty acid that is (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoic acid substituted at position 21 by a hydroxy group.


resolvin T4

A docosanoid that is (8E,10Z,14E,16Z,19Z)-docosapentaenoic acid carrying two hydroxy substituents at positions 7 and 13.


2-hydroxyerucic acid

A 2-hydroxy fatty acid that is erucic acid which is substituted by a hydroxy group at position 2.


Any omega-hydroxy-fatty acid which has a chain length greater than C27.


2,2-dihydroxy-3-methylbutanoic acid

A 2-hydroxy fatty acid that is  isovaleric acid  bearing two hydroxy substituents at position 2.


(2E,19R)-19-hydroxyicos-2-enoic acid

An (omega-1)-hydroxy fatty acid that is trans-2-icosenoic acid in which the pro-R hydrogen at position 19 has been replaced by a hydroxy group.


A dihydroxydocosahexaenoic acid that is (4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoic acid in which the two hydroxy substituents are located at the 14R- and 21S-positions.


(18R)-resolvin E3

A member of the class of resolvins that is (5Z,8Z,11Z,13E,15E)-icosapentaenoic acid which is substituted at positions 17 and 18 by hydroxy groups (the 17,18R) stereoisomer).


(3R)-3,13-dihydroxytridecanoic acid

A dihydroxy monocarboxylic acid that is 13-hydroxytridecanoic acid in which the pro-R hydrogen beta to the carboxy group is replaced by a hydroxy group.


resolvin

Hydroxy fatty acids that are di- or trihydroxy metabolites of the polyunsaturated omega-3 fatty acids, particularly icosapentaenoic acid, docosahexaenoic acid and docosapentaenoic acid.


A docosanoid that is (7Z,10Z,12E,16Z,19Z)-docosapentaenoic acid carrying two hydroxy substituents at positions 14S and 21. An intermediate of specialised proresolving mediators.


A DiHOME obtained by formal dihydroxylation of the 9,10-double bond of octadeca-9,12-dienoic acid (the 12Z-geoisomer).


An 18-HEPE that consists of (5Z,8Z,11Z,14Z,16E)-icosapentaenoic in which the 18-hydroxy group has R-configuration.


11-hydroxymyristic acid

A hydroxy fatty acid that is myristic acid carrying a single hydroxy substituent at position 11.


A docosanoid that is (14E,19Z)-docosa-8,10,12,14,19-pentaenoic acid carrying three hydroxy substituents at positions 7, 16 and 17. An intermediate of specialised proresolving mediators


22-hydroxyprotectin D1

A docosanoid that is protectin D1 in which one of the terminal methyl hydrogens has been replaced by a hydroxy group. An intermediate of specialised proresolving mediators


omega-hydroxy-long-chain fatty acid

A omega-hydroxy-fatty acid with a chain length ranging from C13 to C22.


2-hydroxydodec-2-enoic acid

A hydroxy monounsaturated fatty acid that is dodec-2-enoic acid in which the hydrogen at position 2 has been replaced by a hydroxy group. A minor tautomer of 2-oxododecanoic acid.


(9Z,12Z)-11-hydroxyoctadecadienoic acid

A HODE that is linoleic acid carrying a single hydroxy substituent at position 11.


9-hydroxymyristic acid

A hydroxy fatty acid that is myristic acid carrying a single hydroxy substituent at position 9.


An ultra-long-chain fatty acid that is (12Z,15Z,18Z,21Z,24Z)-triacontapentaenoic acid substituted at position 2 by a hydroxy group.


6-hydroxy-3-isopropenylheptanoic acid

A branched-chain hydroxy fatty acid consisting of heptanoic acid with an isopropenyl group at the 3-position and the hydroxy group at the 6-position.


16-oxoresolvin D2

A member of the class of resolvins that is resolvin D2 in which the 16-hydroxy group has undergone formal oxidation to the corresponding ketone.


(S)-2-hydroxylauric acid

The (S)-enantiomer of 2-hydroxylauric acid.


A 14-HDoHE in which the stereocentre at position 14 has S-configuration.


(S)-3-hydroxylauric acid

The (S)-enantiomer of 3-hydroxylauric acid.


A hydroxydocosapentaenoic acid that is (4Z,7Z,10Z,13Z,15E)-docosapentaenoic acid in which the hydroxy group is located at the 17S-position. The 17S-oxygenated product of omega-6-DPA which possesses anti-inflammatory activity.


10,13-dihydroxyoctadecanoic acid

A hydroxy fatty acid that is octadecanoic acid carrying two hydroxy substituents at positions 10 and 13.


protectin D1

A dihydroxydocosahexaenoic acid that is (4Z,7Z,11E,13E,15Z,19Z)-docosahexaenoic acid in which the two hydroxy substituents are located at positions 10 and 17 (the 10R,17S-stereoisomer). Protectin D1 is one of the specialised proresolving mediators. When produced in neural tissues, it is called neuroprotectin D1


A 9-HODE in which the 9-hydroxy group has R-stereochemistry.


R. ruber mycolic acid

A forty-six membered mycolic acid consisting of 3-hydroxydotriacontanoic acid having a tetradecyl group at the 2-position.


(3R,19R)-19-dihydroxyicosanoic acid

An (omega-1)-hydroxy fatty acid that is (19R)-19-hydroxyicosanoic acid in which the 3-pro-R hydrogen is replaced by a hydroxy group.


(9S,10R)-dihydroxyoctadecanoic acid

A hydroxy fatty acid  that is octadecanoic acid carrying two hydroxy substituents at positions 9 and 10.


(3R,9R)-3,9-dihydroxydecanoic acid

An (omega-1)-hydroxy fatty acid that is (9R)-9-hydroxydecanoic acid in which the 3-pro-R hydrogen is replaced by a hydroxy group.


A hydroperoxy fatty acid that is (4Z,8E,10Z,13Z,15E,19Z)-docosa-4,8,10,13,15,19-hexaenoic acid carrying a hydroperoxy group at the 7S-position and a hydroxy group at the 17R-position. It is an intermediate involved in the resolvin D1 biosynthesis pathway.


(3R,8R)-3,8-dihydroxynonanoic acid

An (omega-1)-hydroxy fatty acid that is (8R)-8-hydroxynonanoic acid in which the 3-pro-R hydrogen is replaced by a hydroxy group.


(S)-3-hydroxypentanoic acid

A 3-hydroxypentanoic acid in which the chiral centre at position 3 has S-configuration.


2-hydroxygondoic acid

A 2-hydroxy fatty acid that is (11Z)-icos-11-enoic acid which carries a hydroxy group at position 2.


10-hydroxymyristic acid

A hydroxy fatty acid that is myristic acid carrying a single hydroxy substituent at position 10.


(3R)-3,20-dihydroxyicosanoic acid

A dihydroxy monocarboxylic acid that is 20-hydroxyicosanoic acid in which the pro-R hydrogen beta to the carboxy group is replaced by a hydroxy group.


(R)-2-hydroxyoctadecanoic acid

The (R)-enantiomer of 2-hydroxyoctadecanoic acid.


A 15-HEPE that consists of (5Z,8Z,11Z,13E,17Z)-icosapentaenoic acid in which the 15-hydroxy group has R-configuration.


(R)-3-hydroxypentanoic acid

A 3-hydroxypentanoic acid in which the chiral centre at position 3 has R-configuration.


An (omega-1)-hydroxy fatty acid that is (18R)-18-hydroxynonadecanoic acid in which the 3-pro-R hydrogen is replaced by a hydroxy group.


(3R,10R)-3,10-dihydroxyundecanoic acid

An (omega-1)-hydroxy fatty acid that is (10R)-10-hydroxyundecanoic acid in which the 3-pro-R hydrogen is replaced by a hydroxy group.


(S)-2-acetyl-2-hydroxybutanoic acid

A 3-oxo monocarboxylic acid that is butanoic acid in which the hydrogens at position 2 are replaced by an acetyl and a hydroxy group (the S enantiomer).


(18S)-resolvin E1

A resolvin that is (6Z,8E,10E,14Z,16E)-icosa-6,8,10,14,16-pentaenoic acid which is substituted at positions 5, 12 and 18 by hydroxy groups (the 5S,12R,18S stereoisomer).


3-hydroxytetracosanoic acid

A 3-hydroxy fatty acid that is the 3-hydroxy derivative of tetracosanoic (lignoceric) acid.


(R)-3-hydroxytetradecanoic acid

A 3-hydroxytetradecanoic acid that has R configuration at position 3. It plays an intermediate role in fatty acid biosynthesis.


A docosanoid that is (8E,10E,12Z,16Z,19Z)-docosapentaenoic acid carrying two hydroxy substituents at positions 7R and 14S. An intermediate of specialised proresolving mediators.


A dihydroxydocosahexaenoic acid that is (4Z,8E,10E,12Z,16Z,19Z)-docosahexaenoic acid in which the two hydroxy substituents are located at the 7S- and 14S-positions.


A hydroxydocosahexaenoic acid that consists of 4Z,7Z,10Z,13Z,16Z,18E-docosahexaenoic acid bearing an additional 20-hydroxy substituent.


A hydroxydocosahexaenoic acid that consists of (4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoic acid bearing an additional 14-hydroxy substituent.


cis-2-hydroxypenta-2,4-dienoic acid

The cis-isomer of 2-hydroxypenta-2,4-dienoic acid.


dihydroxy mycolic acid

A 3-hydroxy fatty acid produced by Mycobacterium tuberculosis.


HEPE

A long-chain polyunsaturated fatty acid that is any icosapentaenoic acid bearing a single hydroxy substituent. An oxidation product of icosapentaenoic acid metabolism.


hydroxy polyunsaturated fatty acid

Any polyunsaturated fatty acid carrying one or more hydroxy substituents.


2-hydroxyphytanic acid

An alpha-hydroxy fatty acid formed from phytanic acid by bacterial cytochrome P450; and also formed in human peroxisomal disorders.


omega-hydroxy-short-chain fatty acid

A omega-hydroxy-fatty acid with a chain length of less than C6.


A hydroxydocosahexaenoic acid that consists of 4Z,7Z,11E,13Z,16Z,19Z-docosahexaenoic acid bearing an additional 10-hydroxy substituent.


16-hydroxy-10-oxohexadecanoic acid

An omega-hydroxy-long-chain fatty acid that is hexadecanoic acid substituted by an oxo group at position 10 and by a hydroxy group at position 16.


A C20 trienoic hydroxy fatty acid consisting of 8-hydroxyicosa-5,9,14-trienoic acid having an epoxy group at the 11,12-position.


A hydroxydocosahexaenoic acid that consists of (4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoic acid bearing an additional 7-hydroxy substituent.


(omega-1)-hydroxy fatty acid

A hydroxy fatty acid that is a straight-chain fatty acid in which one of the hydrogens attached to the carbon adjacent to the terminal methyl group (i.e. at the (omega-1) position) is replaced by a hydroxy group.


(6R)-6-hydroxyheptanoic acid

A 6-hydroxyheptanoic acid that has R configuration at the chiral centre.


(R)-2-hydroxyhexacosanoic acid

A 2-hydroxy fatty acid that is the (R)-2-hydroxy derivative of hexacosanoic acid.


A hydroperoxy fatty acid that is (5E,7Z,10Z,13Z,15E,19Z)-docosa-5,7,10,13,15,19-hexaenoic acid carrying a hydroperoxy group at the 4S-position and a hydroxy group at the 17S-position.


9,12,13-trihydroxyoctadec-10-enoic acid

A TriHOME that is octadec-10-enoic acid in which the three hydroxy substituents are located at positions 9, 12 and 13.


hydroxy monounsaturated fatty acid

Any monounsaturated fatty acid carrying one or more hydroxy substituents.


An (omega-1)-hydroxy fatty acid that is trans-2-tetradecenoic acid in which the 13-pro-R hydrogen is replaced by a hydroxy group.


The (13S)-stereoisomer of HOTrE.


A dihydroxydocosahexaenoic acid that is (4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoic acid in which the two hydroxy substituents are located at the 14R- and 21R-positions.


(3R)-3,16-dihydroxyhexadecanoic acid

A 3,16-dihydroxyhexadecanoic acid in which the chiral centre has R configuration.


17-hydroxymargaric acid

An omega-hydroxy-long-chain fatty acid that is heptadecanoic acid (margaric acid) in which one of the hydrogens of the terminal methyl group has been replaced by a hydroxy group.


(17R)-hydroxydocosahexaenoic acid

A hydroxydocosahexaenoic acid that is any docosahexaenoic acid bearing a single hydroxy substituent at the 17R-position.


A polyunsaturated fatty acid that consists of 4Z,6E,10Z-hexadecatrienoic acid bearing an additional 8R-hydroxy substituent.


β-D-hydroxybutyric acid

The R-enantiomer of 3-hydroxybutyric acid. Involved in the synthesis and degradation of ketone bodies, it can be used as an energy source by the brain during hypoglycaemia, and for the synthesis of biodegradable plastics. It is a sex pheremone in the European spider Linyphia triangularis.


(R)-2-hydroxy-alpha-linolenic acid

A HOTrE that is alpha-linolenic acid substituted at position 2 by a hydroxy group (the R-enantiomer)


2-hydroxynonadecanoic acid

A  2-hydroxy fatty acid that is nonadecanoic acid substituted by a hydroxy group at position 2.


leptomycin

A complex, very long chain, polyunsaturated fatty acid whose core structure comprises 8-oxononadeca-2,10,12,16,18-pentaenoic acid having methyl substituents at positions 3, 5, 7, 9, 11 and 15 and a 3,6-dihydropyran-6-one-2-yl group at position 19.


(S)-2-hydroxyoctadecanoic acid

An optically active form of 2-hydroxyoctadecanoic acid having (S)-configuration.


(3R)-3,19-dihydroxynonadecanoic acid

A dihydroxy monocarboxylic acid that is 19-hydroxynonadecanoic acid in which the pro-R hydrogen beta to the carboxy group is replaced by a hydroxy group.


(R)-2-hydroxylauric acid

The (R)-enantiomer of 2-hydroxylauric acid.


omega-hydroxy fatty acid

Any member of the class of naturally-occurring straight-chain fatty acids n carbon atoms long with a carboxyl group at position 1 and a hydroxyl at position n (omega).


resolvin T1

A docosanoid that is (8E,10Z,14E,16Z,18E)-docosapentaenoic acid carrying three hydroxy substituents at positions 7, 13 and 20.


A hydroxydocosahexaenoic acid that consists of 4Z,7Z,10Z,13Z,17E,19Z-docosahexaenoic acid bearing an additional 16-hydroxy substituent.


3-hydroxyicosanoic acid

A long-chain fatty acid that is icosanoic acid carrying a 3-hydroxy substituent.


resolvin D5

A member of the class of resolvins that is (4Z,8E,10Z,13Z,15E,19Z)-docosahexaenoic acid carrying two hydroxy substituents at positions 7 and 17 (the 7S,17S-stereoisomer).


3-hydroxyoctanoic acid

The (S)-enantiomer of 3-hydroxyoctanoic acid.


(R)-2-hydroxyoctacosanoic acid

A 2-hydroxy fatty acid that is the (R)-2-hydroxy derivative of octacosanoic acid.


A HEPE that is (5Z,7E,11Z,14Z,17Z)-icosapentaenoic acid carrying a hydroxy substituent at position 9.


An 18-HEPE that consists of (5Z,8Z,11Z,14Z,16E)-icosapentaenoic in which the 18-hydroxy group has S-configuration.


(S,S)-9,10-dihydroxyoctadecanoic acid

A 9,10-dihydroxyoctadecanoic acid diastereoisomer in which both stereocentres have S configuration.


(2E,8R)-8-hydroxynon-2-enoic acid

An (omega-1)-hydroxy fatty acid that is (2E)-non-2-enoic acid in which the hydrogen at the 8 pro-R position is replaced by a hydroxy group.


6-hydroxyheptanoic acid

An (omega-1)-hydroxy fatty acid that is heptanoic acid in which one of the hydrogens at position 6 is replaced by a hydroxy group.


A hydroxydocosahexaenoic acid that consists of 4Z,6E,10Z,13Z,16Z,19Z-docosahexaenoic acid bearing an additional 8-hydroxy substituent.


(3R)-3,21-dihydroxyhenicosanoic acid

A dihydroxy monocarboxylic acid that is 21-hydroxyhenicosanoic acid in which the pro-R hydrogen beta to the carboxy group is replaced by a hydroxy group.


dihydroxydocosahexaenoic acid

A docosanoid that consists of any docosahexaenoic acid carrying two hydroxy substituents at unspecified positions.


(2E,18R)-18-hydroxynonadec-2-enoic acid

An (omega-1)-hydroxy fatty acid that is nonadecanoic acid which has been dehydrogenated to introduce a double bond with E configuration between positions 2 and 3 and in which the pro-R hydrogen at position 17 has been replaced by a hydroxy group.


(10R)-10-hydroxyundecanoic acid

An (omega-1)-hydroxy fatty acid that is undecanoic acid in which the 10-pro-R hydrogen is replaced by a hydroxy group.


An ultra-long-chain fatty acid that is (13Z,16Z,19Z,22Z)-octacosatetraenoic acid substituted at position 2 by a hydroxy group.


A docosanoid that is (7Z,9E,11E,16Z,19Z)-docosapentaenoic acid carrying two hydroxy substituents at positions 13 and 14. An intermediate of specialised proresolving mediators.


8-hydroxylauric acid

A hydroxy fatty acid comprising lauric acid carrying a single hydroxy substituent at position 8.


HEDE

A hydroxy fatty acid that is any icosadienoic acid bearing a single hydroxy substituent. An oxidation product of icosadienoic acid metabolism.


2-hydroxynonanoic acid

A monohydroxy fatty acid that is nonanoic acid with a hydroxy group substituted at position C-2.


(4R)-4-hydroxypentanoic acid

An (omega-1)-hydroxy fatty acid that is valeric acid in which the 4-pro-R hydrogen is replaced by a hydroxy group.


omega-hydroxytritriacontanoic acid

An omega-hydroxy fatty acid that is tritriacontanoic acid (C33) acid) substituted by a hydroxy group at position 33.


(9R)-9-hydroxydecanoic acid

An (omega-1)-hydroxy fatty acid that is capric acid in which the 9-pro-R hydrogen is replaced by a hydroxy group.


2-hydroxyoctadecanoic acid

A long-chain fatty acid that is stearic (octadecanoic) acid substituted at position 2 by a hydroxy group.


(R,R)-3,17-dihydroxyoctadecanoic acid

An (omega-1)-hydroxy fatty acid that is (17R)-17-hydroxyoctadecanoic acid ((17R)-17-hydroxystearic acid) in which the 3-pro-R hydrogen is replaced by a hydroxy group.


A dihydroxydocosahexaenoic acid that is (4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoic acid in which the two hydroxy substituents are located at the 14S- and 21S-positions.


A hydroxyicosapentaenoic acid that consists of 5Z,8Z,10E,14Z,17Z-icosapentaenoic acid bearing an additional 12-hydroxy substituent.


A DiHDPA obtained by formal dihydroxylation of the 19,20-double bond of docosa-4,7,10,13,16,19-hexaenoic acid.


resolvin D1

A resolvin that is docosa-4Z,9E,11E,13Z,15E,19Z-hexaenoic acid which is substituted by hydroxy groups at the 7, 8, and 17 positions (the 7S,8R,17S-stereoisomer).


A hydroxydocosahexaenoic acid that consists of 4Z,7Z,10Z,13Z,15E,19Z-docosahexaenoic acid bearing an additional 17-hydroxy substituent.


(3R,15R)-3,15-dihydroxypalmitic acid

An (omega-1)-hydroxy fatty acid that is (15R)-15-hydroxypalmitic acid in which the 3-pro-R hydrogen is replaced by a hydroxy group.


3-hydroxy-3-methyl-2-oxopentanoic acid

A 3-hydroxylated derivative of 3-methyl-2-oxovaleric acid.


A 14-HDoHE in which the stereocentre at position 14 has R-configuration.


(9E)-12-hydroxyoctadec-9-enoic acid

A hydroxy fatty acid that is (9E)-octadec-9-enoic (elaidic) acid carrying a hydroxy substituent at position 12.


2-hydroxylauric acid

A monohydroxy fatty acid with a lauric acid core substituted at position 2 by a hydroxy group, which confers chirality; a component of cellular lipids in Pseudomonas strains.


A hydroxyicosapentaenoic acid that consists of 5Z,8Z,11Z,14Z,16E-icosapentaenoic acid with the hydroxy group located at position 18.


5-hydroxyoctadecanoic acid

A hydroxyoctadecanoic acid that is octadecanoic acid (stearic acid) in which one of the hydrogens at position 5 has been replaced by a hydroxy group.


A dihydroxydocosahexaenoic acid that is (4Z,8E,10E,12Z,16Z,19Z)-docosahexaenoic acid in which the two hydroxy substituents are located at the 7R- and 14S-positions.


2-hydroxyarachidic acid

A long-chain fatty acid that is arachidic (icosanoic) acid substituted at position 2 by a hydroxy group.


(R)-10-hydroxyoctadecanoic acid

A hydroxy fatty acid that is octadecanoic acid (stearic acid) in which the pro-R hydrogen has been replaced by a hydroxy group.


(S)-2-hydroxy-4-methylpentanoic acid

The (S)-enantiomer of 2-hydroxy-4-methylpentanoic acid. Derived from the metabolism of the branched-chain amino acids, it belongs to the 2-hydroxycarboxylic acid group of amino acid metabolites.


(2S)-2-hydroxytetradecanoic acid

A 2-hydroxymyristic acid having 2S-configuration.


A dihydroxydocosahexaenoic acid that is  (4Z,7Z,11E,13Z,15E,19Z)-docosahexaenoic acid in which the two hydroxy substituents are located at positions 10 and 17 (the 10S,17S-stereoisomer). A natural isomer of protectin D1, one of the specialised proresolving mediators.


11-hydroxylauric acid

A medium-chain fatty acid that is lauric acid substituted at position 11 by a hydroxy group.


3-hydroxypentanoic acid

A short-chain fatty acid that is valeric acid in which one of the methylene hydrogens at position 3 has been replaced by a hydroxy group.


(9R,10S)-dihydroxyoctadecanoic acid

A dihydroxy monocarboxylic acid that is octadecanoic acid in which the two hydroxy groups are located at positions 9R and 10S.


8-oxoresolvin D1

A resolvin that is docosa-4Z,9E,11E,13Z,15E,19Z-hexaenoic acid which is substituted by hydroxy groups at the 7 and 17 positions as well as an oxo group at the 8-position (the 7S,17S-stereoisomer).


A hydroxydocosahexaenoic acid that consists of 4Z,7Z,9E,13Z,16Z,19Z-docosahexaenoic acid with the hydroxy group located at position 11.


(18S)-resolvin E2

A member of the class of resolvins that is (6E,8Z,11Z,14Z,16E)-icosapentaenoic acid carrying two hydroxy substituents at positions 5 and 18 (the 5S,18S stereoisomer).


A polyunsaturated fatty acid that is (4Z,7Z,10Z,13Z,15E,19Z)-docosa-4,7,10,13,15,19-hexaenoic acid carrying a hydroxy substituent at the 17R-position.


A trienoic fatty acid that consists of heptadeca-5,8,10-trienoic acid bearing an additional 12-hydroxy substituent.


2-hydroxy-3-methylpentanoic acid

A branched-chain fatty acid that is 3-methylpentanoic acid carrying a hydroxy substitutent at position 2.


12,18-dihydroxyoctadecanoic acid

A long-chain fatty acid that is octadecanoic (stearic) acid substituted at positions 12 and 18 by hydroxy groups.


A HEPE that consists of (5Z,8Z,12E,14Z,17Z)-icosapentaenoic acid in which the hydroxy group is located at position 11.


(3R)-3,18-dihydroxyoctadecanoic acid

A dihydroxy monocarboxylic acid that is 8-hydroxyoctadecanoic acid (18-hydroxystearic acid1) in which the pro-R hydrogen beta to the carboxy group is replaced by a hydroxy group.


(3S,4S)-3-hydroxy-4-methyldecanoic acid

A 3-hydroxy monocarboxylic acid that is 3-hydroxydecanoic acid substituted by a methyl group at position 4 (the 3S,4S stereoisomer).


HOTrE

A long-chain polyunsaturated fatty acid that is any octadecatrienoic acid bearing a single hydroxy substituent. An oxidation product of octadecatrienoic acid metabolism.


(9Z)-16-hydroxyhexadec-9-enoic acid

An omega-hydroxy-long-chain fatty acid that is palmitoleic acid [(9Z)-16-hexadec-9-enoic acid) which is substituted by a hydroxy group at the terminal carbon.


An octadecanoid that is 12,13-epoxy-(9Z)-octadecenoic acid carrying an additional hydroxy substituent at position 18.


9,10-epoxy-18-hydroxyoctadecanoic acid

An epoxy fatty acid that is 9,10-epoxyoctadecanoic acid (9,10-epoxystearic acid) carrying an additional hydroxy substituent at position 18.


3,4-dihydroxy-4-methylhexadecanoic acid

A dihydroxy monocarboxylic acid that consists of palmitic acid bearing two hydroxy substituents at positions 3 and 4 and a methyl substituent at position 4.


(3R)-3,22-dihydroxytricosanoic acid

A dihydroxy monocarboxylic acid that is tricosanoic acid in which the pro-R hydrogen at position 3 and and one of the hydrogens of the terminal methyl group are replaced by hydroxy groups.


An (omega-1)-hydroxy-long-chain fatty acid that is the conjugate base of (9Z,12Z)-octadeca-9,12-dienoic acid which has been substituted at position 17 by a hydroxy group.


aspirin-triggered resolvin D4

A member of the class of resolvins that is (6E,8E,10Z,13Z,15E,19Z)-docosahexaenoic acid carrying three hydroxy substituents at positions 4, 5 and 17 (the 4S,5R,17R-stereoisomer).


An epoxy fatty acid that is (9Z)-11-hydroxyoctadecenoic acid in which the epoxy group is located across positions 12 and 13.


omega-hydroxyhentriacontanoic acid

An omega-hydroxy fatty acid that is hentriacontanoic acid (a C31 acid) substituted by a hydroxy group at position 31.


A hydroxyicosapentaenoic acid that consists of 5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid bearing an additional 15-hydroxy substituent.


A hydroxydocosapentaenoic acid that is (4Z,7Z,10Z,13Z,16Z)-docosapentaenoic acid in which the hydroxy group is located at position 20.


(3R)-3,17-dihydroxymargaric acid

A dihydroxy monocarboxylic acid that is 17-hydroxymargaric acid (17-hydroxyheptadecanoic acid) in which the pro-R hydrogen beta to the carboxy group is replaced by a hydroxy group.


10-hydroxylauric acid

A hydroxy fatty acid comprising lauric acid carrying a single hydroxy substituent at position 10.


(2E,9R)-9-hydroxydec-2-enoic acid

An (omega-1)-hydroxy fatty acid that is trans-2-decenoic acid in which the hydrogen at the 9-pro-R position is replaced by a hydroxy group.


A HODE that consists of 9Z,11E-octadecadienoic acid carrying a 13-hydroxy substituent.


5-hydroxyhexanoic acid

A medium-chain fatty acid that is hexanoic acid substituted at position 5 by a hydroxy group.


A polyunsaturated fatty acid that is (4Z,7Z,10Z,13Z,15E,19Z)-docosa-4,7,10,13,15,19-hexaenoic acid carrying a hydroxy substituent at the 17S-position. It is a metabolite of docosahexaenoic acid in human blood and mouse brain, and serves as a precursor to 17(S)-resolvins.


omega-hydroxyheptacosanoic acid

A omega-hydroxy fatty acid that is  heptacosanoic acid substituted by a hydroxy group at position 27.


(R)-2-hydroxylignoceric acid

A very long-chain fatty acid that is lignoceric acid bearing an (R)-2-hydroxy substituent.


(5R)-5-hydroxyhexanoic acid

An (omega-1)-hydroxy fatty acid that is caproic acid in which the 5-pro-R hydrogen is replaced by a hydroxy group.


An epoxy fatty acid that is (7E,9E,11Z,14Z,16E)-icosa-7,9,11,14,16-pentaenoic acid carrying an epoxy group at position 5S and a hydroxy group at position 18S. It is an intermediate in resolvin E1 biosynthesis.


2-hydroxyheptadecanoic acid

A 2-hydroxy fatty acid that is heptadecanoic acid (margaric acid) substituted by a hydroxy group at position 2.


(3R,13R)-3,13-dihydroxymyristic acid

An (omega-1)-hydroxy fatty acid that is (13R)-13-hydroxymyristic acid in which the 3-pro-R hydrogen is replaced by a hydroxy group.


(R)-3-hydroxylauric acid

The (R)-enantiomer of 3-hydroxylauric acid. An intermediate in fatty acid biosynthesis.


3,16-dihydroxyhexadecanoic acid

A dihydroxy monocarboxylic acid that consists of palmitic acid bearing two hydroxy substituents at positions 3 and 16.


(2E,12R)-12-hydroxytridec-2-enoic acid

An (omega-1)-hydroxy fatty acid that is (2E)-tridec-2-enoic acid in which the 12-pro-R hydrogen is replaced by a hydroxy group.


A hydroperoxy fatty acid that is (5E,7Z,10Z,13Z,15E,19Z)-docosa-5,7,10,13,15,19-hexaenoic acid carrying a hydroperoxy group at the 4S-position and a hydroxy group at the 17R-position.


9,10-epoxy-17-hydroxyoctadecanoic acid

An epoxy fatty acid that is 9,10-epoxyoctadecanoic acid (9,10-epoxystearic acid) carrying an additional hydroxy substituent at position 17.


2-hydroxypenta-2,4-dienoic acid

A 5-carbon, bis-unsaturated, alpha-hydroxy fatty acid metabolite of the proteobacterium substrate 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid (HOPDA).


A hydroxyeicosadienoic acid that consists of 11Z,13E-eicosatrienoic acid bearing a 15-hydroxy substituent. It is produced by non-enzymatic oxidation of 11,14-eicosadienoic acid. There are no reports in the literature of biological activity associated with 15-HEDE.


(3R)-3,15-dihydroxypentadecanoic acid

A dihydroxy monocarboxylic acid that is 15-hydroxypentadecanoic acid in which the pro-R hydrogen beta to the carboxy group is replaced by a hydroxy group.


3-hydroxyheptanoic acid

A 3-hydroxy fatty acid that is heptanoic acid in which one of the hydrogens at position 3 is replaced by a hydroxy group.


(8R)-8-hydroxynonanoic acid

An (omega-1)-hydroxy fatty acid that is nonanoic acid in which the 8-pro-R hydrogen is replaced by a hydroxy group.


(2E,6R)-6-hydroxyhept-2-enoic acid

A hydroxy fatty acid that is trans-2-heptenoic acid in which the 6-pro-R hydrogen is replaced by a hydroxy group.


aspirin-triggered resolvin D3

A member of the class of resolvins that is (5Z,7E,9E,13Z,15E,19Z)-docosahexaenoic acid carrying three hydroxy substituents at positions 4, 11 and 17 (the 4S,11R,17R-stereoisomer)


9-hydroxyundec-10-enoic acid

A hydroxy monounsaturated fatty acid that is undec-10-enoic acid which is substituted by a hydroxy group at position 9. It has been isolated from the leaves of Corchorus olitorius, also known as the medicinal foodstuff moroheiya.


(3R)-3,14-dihydroxymyristic acid

A dihydroxy monocarboxylic acid that is 17-hydroxymyristic acid in which the pro-R hydrogen beta to the carboxy group is replaced by a hydroxy group.


A dihydroxydocosapentaenoic acid (DiHDPE) that is (7Z,11E,13E,15Z,19Z)-docosapentaenoic acid in which the hydrogens at the 10 pro-R and 17 pro-S positions have been replaced by hydroxy groups. It is an intermediate of specialized proresolving mediators.


12-(octadecanoyloxy)octadecanoic acid

A fatty acid ester obtained by formal condensation of the carboxy group of octadecanoic acid with the hydroxy group of 12-hydroxyoctadecanoic acid.


TriHOME

A trihydroxyoctadecenoic acid metabolite of linoleic acid formed by formal hydroxylation across one of the double bonds of hydroperoxyoctadecadienoic acids (HPODEs).


The (R)-enantiomer of 3-hydroxy-3-methyl-2-oxopentanoic acid.


A DiHOME obtained by formal dihydroxylation of the 12,13-double bond of octadeca-9,12-dienoic acid (the 9Z-geoisomer).


A dihydroxydocosahexaenoic acid that is (4Z,8E,10Z,12E,16Z,19Z)-docosahexaenoic acid in which the two hydroxy substituents are located at the 7S- and 14S-positions.


18-hydroxyoctadecanoic acid

An omega-hydroxy-long-chain fatty acid that is octadecanoic (stearic) acid in which one of the hydrogens of the terminal methyl group has been replaced by a hydroxy group.


17-oxoresolvin D1

A resolvin that is docosa-4Z,9E,11E,13Z,15E,19Z-hexaenoic acid which is substituted by hydroxy groups at the 7 and 8 positions as well as an oxo group at the 17-position (the 7S,8R-stereoisomer).


(R)-2-hydroxy-4-methylpentanoic acid

The (R)-enantiomer of 2-hydroxy-4-methylpentanoic acid. Found in patients with short-bowel syndrome (an inborn error of metabolism), and in maple syrup urine disease, MSUD.


(18R)-18-hydroxynonadecanoic acid

An (omega-1)-hydroxy fatty acid that is nonadecanoic acid in which the 18-pro-R hydrogen is replaced by a hydroxy group.


(3R,22R)-3,22-dihydroxytricosanoic acid

A dihydroxy monocarboxylic acid that is tricosanoic acid in which the pro-R hydrogens at positions 3 and 22 are replaced by hydroxy groups.


resolvin D6

A member of the class of resolvins that is (5E,7Z,10Z,13Z,15E,19Z)-docosahexaenoic acid carrying two hydroxy substituents at positions 4 and 17 (the 4S,17S-stereoisomer).


(2E,15R)-15-hydroxyhexadec-2-enoic acid

An (omega-1)-hydroxy fatty acid that is (E)-hexadec-2-enoic acid in which the 15-pro-R hydrogen is replaced by a hydroxy group.


A 9,10-epoxy-18-hydroxyoctadecanoic acid in which the chiral centres at positions 9 and 10 have R- and S-configuration respectively.


(R)-2-hydroxynonanoic acid

A nine-carbon straight-chain (2R)-2-hydroxy monocarboxylic acid.


An optically active form of 6-hydroxy-3-isopropenylheptanoic acid having (3R,6R)-configuration.


A hydroxydocosapentaenoic acid that consists of (8E,10Z,13Z,16Z,19Z)-docosapentaenoic acid carrying a hydroxy substituent at position 7. An intermediate of specialised proresolving mediators.


resolvin D3

A member of the class of resolvins that is (5Z,7E,9E,13Z,15E,19Z)-docosahexaenoic acid carrying three hydroxy substituents at positions 4, 11 and 17 (the 4S,11R,17S-stereoisomer).


DiHDPE

A hydroxy fatty acid obtained by formal dihydroxylation across one of the double bonds of any docosahexaenoic acid.


A docosanoid that is (15E,19Z)-docosa-9,11,13,15,19-pentaenoic acid carrying three hydroxy substituents at positions 7S, 8 and 17S. An intermediate of specialised proresolving mediators


A HODE that consists of (10E,12Z)-octadecadienoic acid with the hydroxy substituent located at position 9.


soppiline A

A hydroxy monocarboxylic acid that is icosanoic acid carrying a hydroxy group at position 3R, methyl group at position 18, cis double bonds at positions 5 and 9, and trans double bonds at positions 7 and 18.


9,10,18-trihydroxyoctadecanoic acid

An omega-hydroxy fatty acid that is 18-hydroxyoctadecanoic acid carrying two additional hydroxy substituents at positions 9 and 10.


An (omega-1)-hydroxy fatty acid that is trans-2-pentadecenoic acid in which the 14-pro-R hydrogen is replaced by a hydroxy group.


A HEPE obtained by hydroxylation at position 19 of all-cis-5,8,11,14,17-icosapentaenoic acid.


2-hydroxybehenic acid

A long-chain fatty acid that is behenic (docosanoic) acid substituted at position 2 by a hydroxy group.


A hydroxydocosahexaenoic acid that consists of 5E,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid bearing an additional 4-hydroxy substituent.


12-hydroxyoctadecanoic acid

A hydroxy fatty acid that is stearic acid bearing a hydroxy substituent at position 12.


13-hydroxydocosanoic acid

A C22 hydroxy fatty acid with the hydroxy group at the 13-position and intermediate in the synthesis of sophorosyloxydocosanoate; a yeast glycolipid with potential medical and chemical engineering applications.


A 15-HEPE that consists of (5Z,8Z,11Z,13E,17Z)-icosapentaenoic acid in which the 15-hydroxy group has S-configuration.


2-hydroxypentadecanoic acid

A 2-hydroxy fatty acid that is pentadecanoic acid substituted by a hydroxy group at position 2.


(2E,10R)-10-hydroxyundec-2-enoic acid

An (omega-1)-hydroxy fatty acid that is trans-undec-2-enoic acid in which the 10-pro-R hydrogen is replaced by a hydroxy group.


hydroxybutyric acid

Any compound comprising a butyric acid core carrying at least one hydroxy substituent.


An 11-HEPE that consists of (5Z,8Z,12E,14Z,17Z)-icosapentaenoic acid in which the hydroxy group is located at the 11R-position.


12-hydroxyheptadecatrienoic acid

A trienoic fatty acid that consists of (5Z,8E,10E)-heptadeca-5,8,10-trienoic acid bearing an additional 12S-hydroxy substituent.