choline alfoscerate

A member of the class of phosphocholines that is the choline ester of sn-glycero-3-phosphate. It is one of the major osmolyte in the renal medullary cells.


name: (25R)-26,26,26-trifluoro-1alpha,25-dihydroxyvitamin D3 / (25R)-26,26,26-trifluoro-1alpha,25-dihydroxycholecalciferol


psychosine

A glycosylsphingoid consisting of sphingosine having a beta-D-galactosyl residue attached at the 1-position.


oxidized Watasenia luciferin

A member of the class of pyrazines in which the pyrazine ring is substituted at positions 2, 3, and 5 by [4-(sulfooxy)phenyl]acetamido, benzyl, and 4-(sulfooxy)phenyl groups, respectively.


bihapten 1 dimethyl ether

A butan-4-olide having a methylidene group at the 3-position and a 9-(2,3-dimethoxyphenyl)nonyl substituent at the 5-position.


oleoside 11-methyl ester

A secoiridoid glycoside that is [(2R,3E,4S)-3-ethylidene-2-hydroxy-5-(methoxycarbonyl)-3,4-dihydro-2H-pyran-4-yl]acetic acid in which the anometric hydroxy group has been converted to the corresponding beta-D-glucoside. It has been isolated from several plant species including Olea europaea.


A trisaccharide found in vegetables consisting of beta-D-fructofuranose having beta-D-fructofuranosyl and alpha-D-glucopyranosyl residues attached at the 1- and 2-positions respectively.


2-aminomuconic acid

The 2-amino derivative of muconic acid.


name: Capsicum annuum Fluorescent chlorophyll catabolite


The (3S)-trans-diastereomer of 3-hydroxy-L-proline.


A member of the class of furans that is furan in which the hydrogen at position 2 is replaced by a decyl group.


GLYOXYLATE

A 2-oxo monocarboxylic acid that is acetic acid bearing an oxo group at the alpha carbon atom.


name: 1,25-dihydroxy-22-oxavitamin D3 3-hemiglutarate/ 1,25-dihydroxy-22-oxacholecalciferol 3-hemiglutarate


An aminopyrimidine that is pyrimidine in which the hydrogens at positions 2, 4, and 5 are replaced by methyl, amino, and hydroxymethyl substituents, respectively.


dihydrosphingosine 1-phosphate

A sphingoid 1-phosphate that is the monophosphorylated derivative of  sphinganine.


A member of the class of furans that is furan substituted by an (ethylsulfanyl)methyl group at position 2.


Ac-SDKP

A tetrapeptide that is Ser-Asp-Lys-Pro in which the N-terminal amino group carries an acetyl group. It is selective inhibitor of primitive haematopoietic cell proliferation and exhibits anti-inflammatory, anti-fibrotic, and pro-angiogenic properties.


3-sulfopyruvic acid

A carboxyalkanesulfonic acid comprising pyruvic acid with a sulfo group attached at the C-3 position.


D-ribose with the hydroxy group substituted for a methylthio group at position C-5.


PYRIMIDINE

The parent compound of the pyrimidines; a diazine having the two nitrogens at the 1- and 3-positions.


mannitol

The D-enantiomer of mannitol.


name: Okanin 4-methyl ether 4'-O-(2''-O-caffeoyl-6''-O-acetylglucoside)


name: Kaempferol 7,4'-dimethyl ether 3-O-sulfate


An alk-1-enylacylglycerol compound having the alk-1-enyl group at position 1 and the acyl group at position 2.


A member of the class of  hydroxyfluorenes that is 9H-fluorene substituted by a hydroxy group at position 9 (the non-aromatic carbon).


keto-D-fructose 1,6-bisphosphate

A ketohexose bisphosphate that is D-fructose substituted by phosphate groups at positions 1 and 6.


A quinoline N-oxide carrying a nitro substituent at position 4.


name: Kaempferol 7,4'-dimethyl ether 3-(6''-(E)-p-coumarylglucoside)


NADH

A coenzyme found in all living cells; consists of two nucleotides joined through their 5'-phosphate groups, with one nucleotide containing an adenine base and the other containing nicotinamide.


mandelonitrile

A cyanohydrin that is phenylacetonitrile in which one of the methylene hydrogens is replaced by a hydroxy group.


HALOSTACHINE

An  alkaloid that is ethanolamine having the phenyl group at the 1-position and a methyl group attached to the nitrogen. It has been isolated from Halostachys caspica.


salicylic acid

A monohydroxybenzoic acid that is benzoic acid with a hydroxy group at the ortho position. It is obtained from the bark of the white willow and wintergreen leaves.


oligosaccharide phosphate

An oligosaccharide derivative in which at least one hydroxy group has been phosphorylated.


gallate

A trihydroxybenzoate that is the conjugate base of gallic acid.


creatine

A glycine derivative having methyl and amidino groups attached to the nitrogen.


name: 1alpha,24,25,28-tetrahydroxyvitamin D2 / 1alpha,24,25,28-tetrahydroxyergocalciferol


A doubly-charged N-acyl-L-alpha-amino acid anion resulting from deprotonation of both carboxy groups of N-formyl-L-aspartic acid.


The D-enantiomer of 5-oxoproline.


A ketoaldonic acid phosphate comprising 5-dehydro-2-deoxy-D-gluconic acid having the phosphate group at the 6-position.


L-saccharopine

The N(6)-(1,3-dicarboxypropan-1-yl) derivative of L-lysine.


name: Scutellarein 6,4'-dimethyl ether 7-(2'''-acetylrutinoside)


name: 6-Hydroxyluteolin 6,3'-dimethyl ether 7-sulfate


A cyclohexane-1,2-diol with trans-configuration. It is a metabolite of cyclohexene oxide and other such compounds.


ERGOSTEROL

A phytosterol consisting of ergostane having double bonds at the 5,6-, 7,8- and 22,23-positions as well as a 3beta-hydroxy group.


β-Cyano-L-alanine

A cyanoamino acid that is the 3-cyano-derivative of L-alanine.


L-rhamnofuranose

The furanose form of L-rhamnose.


An aldonolactone phosphate comprising D-glucono-1,5-lactone having the phosphate group at the 6-position.


A beta-amino acid comprising propionic acid having amino and 4-hydroxyphenyl groups attached at the 3-position.


name: Astaxanthin diglucoside/ Astaxanthin beta-D-diglucoside


lipid X

An N-acyl-D-glucosamine 1-phosphate where the N-acyl group is (R)-3-hydroxytetradecanoyl and carrying an additional (R)-3-hydroxytetradecanoyl group at the 3-position.


(R)-2,4-dihydroxy-3-oxobutanoic acid

The 3-dehydro derivative of L-threonic acid.


scytalone

A cyclic ketone that is 3,4-dihydronaphthalen-1(2H)-one substituted by hydroxy groups at positions 3, 6, and 8.


L-KYNURENINE

A kynurenine that has L configuration.


A tricarboxylic acid trianion, obtained by deprotonation of the three carboxy groups of citric acid.


N-acetyl-D-glucosaminic acid

The N-acetyl derivative of D-glucosaminic acid.


name: 1alpha,25-dihydroxy-(26,26)-(27,27)-diethanovitamin D3 / 1alpha,25-dihydroxy-(26,26)-(27,27)-diethanocholecalciferol


5-hydroxymethyldeoxycytidylic acid

A 2'-deoxycytidine phosphate compound having the phosphate group at the 5'-position and a hydroxymethyl substituent at the 5-position.


name: 1alpha,25-dihydroxy-20-epivitamin D2 / 1alpha,25-dihydroxy-20-epiergocalciferol


A doubly-charged N-acyl-L-alpha-amino acid anion resulting from deprotonation of both carboxy groups of N-acetyl-L-aspartic acid.


VITEXIN

An apigenin flavone glycoside, which is found in the passion flower, bamboo leaves and pearl millet


A GDP-sugar having 4-dehydro-6-deoxy-alpha-D-mannose as the sugar portion.


name: 23,23-difluoro-1alpha,25-dihydroxyvitamin D3 / 23,23-difluoro-1alpha,25-dihydroxycholecalciferol


name: Dimethylprotoporphyrin IX dimethyl ester


β-alanine

A naturally-occurring beta-amino acid comprising propionic acid with the amino group in the 3-position.


name: (6RS)-22-oxo-23,24,25,26,27-pentanorvitamin D3 6,19-sulfur dioxide adduct / (6RS)-22-oxo-23,24,25,26,27-pentanorcholecalciferol 6,19-sulfur dioxide adduct


name: trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester


ADP-D-ribose

A nucleotide-sugar having ADP as the nucleotide fragment and D-ribofuranos-5-yl as the sugar component.


monoacylglycerol phosphate

Derivatives of phosphoglycerols which have only one of the alcohol groups of the glycerol backbone ester-linked with a fatty acid.


cortisone

A C21-steroid that is pregn-4-ene substituted by hydroxy groups at positions 17 and 21 and oxo group at positions 3, 11 and 20.


A primary alcohol that is uracil bearing a hydroxymethyl substituent at the 5-position.


A member of the class of dihydroflavonols that is the 2,3-dihydro derivative of gossypetin.


name: Quercetagetin 4'-methyl ether 7-(6-(E)-caffeylglucoside)


heteroglycan

A polysaccharide composed of two or more different types of monosaccharides,


An oxo dicarboxylate obtained by removal of a proton from both of the carboxylic acid groups of (Z)-5-oxohex-2-enedioic acid.


name: Hydroxylated N-acetyl desmethyl frovatriptan


A benzenetriol carrying hydroxy groups at positions 1, 2 and 4.


name: 2-Methyl-3 or 5 or 6-(furfurylthio)pyrazine (mixture of isomers)


deoxycorticosterone

A mineralocorticoid that is progesterone substituted at position 21 by a hydroxy group.


L-alanine

The L-enantiomer of alanine.


A leukotriene that is (5S,7E,9E,11Z,14Z)-5-hydroxyicosa-7,9,11,14-tetraenoic acid in which a glutathionyl group is attached at position 6 via a sulfide linkage.


citral

A monoterpenoid that is (2E,6E)-octa-2,6-dienal substituted by methyl groups at positions 3 and 7.


name: 1alpha,25-dihydroxy-2beta-(6-hydroxyhexyl)vitamin D3 / 1alpha,25-dihydroxy-2beta-(6-hydroxyhexyl)cholecalciferol


A derivative of L-serine having a 3-O-D-galactosyl-N-acetyl-beta-D-galactosaminyl moiety attached to the side-chain oxygen.


The (R,R) diastereoisomer of butane-2,3-diol.


name: (23Z)-25-hydroxy-16,17,23,24-tetradehydrovitamin D3 / (23Z)-25-hydroxy-16,17,23,24-tetradehydrocholecalciferol


An androstane-3,17-dione with a 5beta-configuration.


A monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of 1-piperideine-6-carboxylic acid.


D-ribose

A ribose in which the chiral carbon atom furthest away from the aldehyde group (C4') has the same configuration as in D-glyceraldehyde.


bilirubin

A member of the class of  biladienes that is a linear tetrapyrrole with the dipyrrole units being of both exovinyl and endovinyl type. A product of heme degradation, it is produced in the reticuloendothelial system by the reduction of biliverdin and transported to the liver as a complex with serum albumin.


deoxyribonucleic acid

High molecular weight, linear polymers, composed of nucleotides containing deoxyribose and linked by phosphodiester bonds; DNA contain the genetic information of organisms.


name: (6R)-vitamin D2 6,19-sulfur dioxide adduct / (6R)-ergocalciferol 6,19-sulfur dioxide adduct


A 5-oxo-2-furylacetic acid having a carboxy group at the 2-position.


Compound 7 in ref.


Compound 3 in ref.


Compound 5 in ref.


Compound 8 in ref.


An amino disaccharide that consists of N-acetyl-D-glucosamine having an N-acetyl-4,6-di-O-sulfo-beta-D-galactosaminyl residue attached at position 4.


An amino disaccharide that consists of 3-sulfated N-acetyl-D-glucosamine having a 3-sulfated N-acetyl-beta-D-galactosaminyl residue attached at position 4.


A guanidinium ion resulting from the protonation of the guanidyl group of camostat. Major microspecies at pH 7.3.


A D-galactosyl-N-acylsphingosine in which the galactosyl moiety is attached by a beta-linkage at the anomeric position and in which the N-acyl moiety bears a hydroxy group alpha- to the carboxamide group


A member of the class of imidazopyrimidopyrimidines that is 5,6-dihydroimidazo[1,2-a]pyrimido[5,4-e]pyrimidine substituted by [4-(morpholin-4-yl)phenyl]amino, oxo and 2,6-dichlorophenyl groups at positions 2, 5 and 6, respectively. It is a potent inhibitor of Wee-1 kinase (Ki = <10 nM).


imidazopyrimidopyrimidine

An organic heterotricyclic compound that is imidazole which is ortho fused to a pyrimidine ring which itself is ortho fused to a pyrimidine ring.


A dicarboxylic acid monoester(1-) that is the conjugate base of 6-O-malonyl-trans-rhaponticin, resulting from the deprotonation of the carboxy group. Major microspecies at pH 7.3.


cis-rhaponticin

A rhaponticin in which the double bond adopts a cis-configuration.


OXALIC ACID

An alpha,omega-dicarboxylic acid that is ethane substituted by carboxyl groups at positions 1 and 2.


An azamacrocycle with formula C34H32N8O7S isolated from the cultured mycelium of Streptomyces nobilis. It exhibits potent cytotoxic activity against human cancer cell lines.


Thr-Thr zwitterion

A dipeptide zwitterion resulting from transfer of a proton from the carboxy to the amino group of L-threonyl-L-threonine; major species at pH 7.3.


Thr-Ser zwitterion

A dipeptide zwitterion resulting from transfer of a proton from the carboxy to the amino group of L-threonyl-L-serine; major species at pH 7.3.


Ser-Thr zwitterion

A dipeptide zwitterion resulting from transfer of a proton from the carboxy to the amino group of L-seryl-L-threonine; major species at pH 7.3.


Gly-His zwitterion

A dipeptide zwitterion resulting from transfer of a proton from the carboxy to the amino group of glycyl-L-histidine; major species at pH 7.3.


Ala-Cys zwitterion

A dipeptide zwitterion resulting from transfer of a proton from the carboxy to the amino group of L-alanyl-L-cysteine; major species at pH 7.3.


L-histidinol phosphate

The O-phospho derivative of L-histidinol.


GlyTouCan G00406II

A composition-only glycan consisting of four hexosyl groups, two acetaminohexosyl groups, and one 6-deoxyhexosyl group (identities and connectivity unknown). Composition: Hex4 HexNAc2 dHex1.


propylene glycol

The simplest member of the class of propane-1,2-diols, consisting of propane in which a hydrogen at position 1 and a hydrogen at position 2 are substituted by hydroxy groups. A colourless, viscous, hygroscopic, low-melting (-59degreeC) and high-boiling (188degreeC) liquid with low toxicity, it is used as a solvent, emulsifying agent, and antifreeze.


A nucleoside triphosphate(4-) obtained by global deprotonation of the triphosphate OH groups of 2-hydroxy-ATP; major species present at pH 7.3.


A nucleoside 5'-monophosphate(2-) that results from the removal of two protons from the phosphate group of 2-hydroxy-AMP. Major microspecies at pH 7.3.


Major microspecies at pH 7.3


A lysoglycerophospholipid that has an acyl group at position sn-1.


A disaccharide phosphate that is N-acetyl-6-O-phospho-beta-D-glucosamine having a beta-D-galactosyl residue attached at O-4.


D-phenylalanine

The D-enantiomer of phenylalanine.


A hydroxy monocarboxylic acid anion that is the conjugate base of cis,cis-2,4-dihydroxy-5-methyl-6-oxo-2,4-hexadienoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


A 2,4-dihydroxy-5-methyl-6-oxo-2,4-hexadienoic acid in which both double bonds adopt a trans-configuration.


A hydroxy monocarboxylic acid anion that is the conjugate base of trans,trans-2,4-dihydroxy-5-methyl-6-oxo-2,4-hexadienoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


A branched amino pentasaccharide consisting of a linear tetrasaccharide comprising N-acetyl-alpha-D-galactosamine, beta-D-galactose, N-acetyl-beta-D-glucosamine and N-acetyl-D-galactosamine residues linked sequentially (1->3), (1->4) and (1->6), to the beta-D-galactosamine of which is also linked (1->2) an alpha-L-fucosyl residue.


stellatic acid

A sesterterpenoid with formula C25H38O2 which is isolated from the fungus Emericella variecolor.


tropate

A hydroxy monocarboxylic acid anion that results from the deprotonation of the carboxylic acid group of tropic acid.


A tertiary ammonium ion that is the conjugate acid of dilazep resulting from the protonation of the two amino groups of the diazepane moiety.


An amino tetrasaccharide comprising alpha-D-galactose, beta-D-galactose, N-acetyl-beta-D-glucosamine and alpha-D-mannose residues linked sequentially (1->3), (1->4) and (1->2).


A branched amino pentasaccharide comprising alpha-D-galactose, beta-D-galactose, N-acetyl-beta-D-glucosamine and alpha-D-mannose residues linked sequentially (1->3), (1->4) and (1->2), to the beta-D-galactose residue of which is also linked (1->2) an alpha-L-fucosyl residue.


A branched amino pentasaccharide comprising N-acetyl-alpha-D-galactosamine, beta-D-galactose, N-acetyl-beta-D-glucosamine and alpha-D-mannose residues linked sequentially (1->3), (1->4) and (1->2), to the beta-D-galactose residue of which is also linked (1->2) an alpha-L-fucosyl residue.


An amino trisaccharide consisting of alpha-D-galactosyl, N-acetyl-beta-D-glucosaminyl and alpha-D-mannose residues joined in sequence by (1->3) and (1->2) glycosidic bonds.


A member of the class of pyrrolopyrimidines that is 7H-pyrrolo[2,3-d]pyrimidine substituted by (1-phenylethyl)amino and 4-[(4-ethylpiperazin-1-yl)methyl]phenyl groups at positions 4 and 6, respectively.


An amino tetrasaccharide comprising alpha-N-acetylneuraminyl, beta-D-galactosyl, N-acetyl-beta-D-glucosaminyl and alpha-D-mannose residues linked sequentially (2->3), (1->3) and (1->2).


nirmatrelvir

An azabicyclohexane that is (1R,5S)-3-azabicyclo[3.1.0]hexane substituted by {(1S)-1-cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl}aminoacyl, 3-methyl-N-(trifluoroacetyl)-L-valinamide, methyl and methyl groups at positions 2S, 3, 6 and 6, respectively. It is the first orally administered inhibitor of SARS-CoV-2 main protease developed by Pfizer and used in combination with ritonavir for the treatment of COVID-19.


FAVIPIRAVIR-RTP

A nuceloside analogue in which the nucleobase is favipiravir. It is a RNA-dependent RNA polymerase inhibitor which exhibits anti-influenza and anti-coronaviral activities.


A neopterin where positions C-7 and C-8 have been hydrogenated.


An  oligosaccharide derivative consisting of a linear trisaccharide backbone of a beta-D-mannosyl residue, an N-acetyl-beta-D-glucosyl residue and (at the reducing end) an N-acetyl-beta-D-glucose residue, all linked through (1->4) glycosidic linkages, to the mannosyl residue of which are linked two separate N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl tetrasaccharide units via (1->3) and (1->6) glycosidic linkages.


cholesteryl ester

A sterol ester obtained by formal condensation of the carboxy group of any carboxylic acid with the 3-hydroxy group of cholesterol.


A glycotetraosylceramide having beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucose as the tetrasaccharide component.


An ethanediol that is ethane-1,2-diol in which a hydrogen attached to a carbon is replaced by a 3,4-dimethoxyphenyl group.


A N-acyl-L-amino acid  that is L-glutamine in which one of the hydrogens attached to the alpha-amino group is replaced by an acyl group.


GDP-fucose

A GDP-fucose in which the fucosyl residue has L-configuration.


S-inosyl-L-homocysteine

L-homocysteine substituted at sulfur by a 5'-deoxyinosin-5'-yl group.


A hexose obtained by selective dehydration at the 5-position of D-fructose.


N-acetylneuraminic acid

An N-acylneuraminic acid where the N-acyl group is specified as acetyl.


THYMIDINE MONOPHOSPHATE

The neutral species of thymidine 5'-monophosphate (2'-deoxythymidine 5'-monophosphate).


name: Glycerol 1-(9Z-octadecenoate) 2-tetradecanoate 3-phosphate


name: 9-Octadecenoic acid 1-[[(1-oxohexadecyl)oxy]methyl]-2-(phosphonoxy)ethyl ester


riboflavin

D-Ribitol in which the hydroxy group at position 5 is substituted by a 7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl moiety. It is a nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables, but the richest natural source is yeast. The free form occurs only in the retina of the eye, in whey, and in urine; its principal forms in tissues and cells are as flavin mononucleotide and flavin-adenine dinucleotide.


AMYGDALIN

An amygdalin in which the stereocentre on the cyanohydrin function has R-configuration.


glucomannan

A heteroglycan consisting of beta-(1->4)-linked D-glucose (G) and D-mannose (M) in a proportion of 5:8. The basic polymeric repeating unit has the pattern: GGMMGMMMMMGGM, with branching through beta-(1->3)- and beta-(1->6)-glucosyl linkages. Acetate groups are present on C-6 every 9-19 units of the main chain.


S-substituted glutathione

A glutathione derivative that is glutathione in which the hydrogen of the thiol has been replaced by any other group.


2-hydroxyadipic acid

An adipic acid derivative having a 2-hydroxy substituent.


(S)-dihydroorotic acid

The (S)-enantiomer of dihydroorotic acid that is an intermediate in the metabolism of pyridine.


progesterone

A C21-steroid hormone in which a pregnane skeleton carries oxo substituents at positions 3 and 20 and is unsaturated at C(4)-C(5). As a hormone, it is involved in the female menstrual cycle, pregnancy and embryogenesis of humans and other species.


allysine

An alpha-amino acid consisting of lysine having an oxo group in place of the side-chain amino group.


2-dehydro-3-deoxy-D-galactonic acid

The 2-dehydro-3-deoxy derivative of D-galactonic acid.


chitin

An aminoglycan consisting of beta-(1->4)-linked N-acetyl-D-glucosamine residues.


chelirubine

A benzophenanthridine alkaloid that is sanguinarine bearing a methoxy substituent at position 10.


2-dehydro-3-deoxy-D-gluconic acid

The 2-dehydro-3-deoxy derivative of D-gluconic acid.


An indole alkaloid with formula C21H24N2O3. It is a biosynthetic precursor for a variety of monoterpenoid indole alkaloids.


fecosterol

A 3beta-sterol having a 5alpha-ergostane skeleton with a methylidene group at C-24 and double bonds at the C-8 and C-24(28) positions.


(carboxymethoxy)succinic acid

The carboxymethoxy derivative of succinic acid.


(S)-N-methylcoclaurine

The (S)-enantiomer of N-methylcoclaurine.


TETRACHLOROHYDROQUINONE

A tetrachlorobenzene that is 1,2,4,5-tetrachlorobenzene in which the hydrogens at positions 3 and 6 are replaced by hydroxy groups.


biphenylol

A member of the class of hydroxybiphenyls that is biphenyl substituted by a hydroxy group at position 2. It is generally used as a post-harvest fungicide for citrus fruits.


D-glucitol 6-phosphate

The 6-O-phospho derivative of D-glucitol.


nitrous oxide

A nitrogen oxide consisting of linear unsymmetrical molecules with formula N2O. While it is the most used gaseous anaesthetic in the world, its major commercial use, due to its solubility under pressure in vegetable fats combined with its non-toxicity in low concentrations, is as an aerosol spray propellant and aerating agent for canisters of 'whipped' cream.


all-trans-undecaprenyl diphosphate

The all-trans-isomer of undecaprenyl diphosphate.


nororientaline

An isoquinoline alkaloid consisting of a tetrahydroisoquinoline core with 4-hydroxy-3-methoxybenzyl, methoxy and hydroxy substituents at positions 1, 6 and 7 respectively; major species at pH 7.3.


A glucosaminylphosphatidylinositol compound consisting of D-glucosamine joined to 1-phosphatidyl-1D-myo-inositol via a (1->6)-alpha-linkage.


3-phosphoglyceric acid

A monophosphoglyceric acid having the phospho group at the 3-position. It is an intermediate in metabolic pathways like glycolysis and calvin cycle.


L-aspartic acid

The L-enantiomer of aspartic acid.


1-carboxyvinyl carboxyphosphonate

An organic phosphonate having O-1-carboxyvinyl and C-carboxy substituents.


cellobiose

A glycosylglucose consisting of two glucose units linked via a beta(1->4) bond.


D-glutamine

The D-enantiomer of glutamine.


L-erythrulose 1-phosphate

The L-enantiomer of erythrulose 1-phosphate.


A nitroaniline carrying a nitro group at position 4.


cyclic CMP

A 3',5'-cyclic pyrimidine nucleotide having cytosine as the nucleobase.


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.


A 3-hydroxypropionyl-CoA having a 4-hydroxy-3-methoxyphenyl group at the 3-position.


3-hydroxybenzyl alcohol

A hydroxybenzyl alcohol that is phenol substituted at position C-3 by a hydroxymethyl group.


glycolaldehyde

The glycolaldehyde derived from ethylene glycol. The parent of the class of glycolaldehydes.


N-amidino-L-aspartic acid

An aspartic acid derivative comprising L-aspartic acid carrying an N-amidino substituent.


streptomycin

A amino cyclitol glycoside that consists of streptidine having a disaccharyl moiety attached at the 4-position. The parent of the streptomycin class


The 2-carboxy derivative of D-arabinitol.


An isoquinoline alkaloid having a tetrahydroisoquinoline core with 3,4-dihydroxybenzyl, methoxy and hydroxy groups at the 1-, 6- and 7-positions respectively; major species at pH 7.3.


A dicarboxylic acid dianion that is obtained from dimethylmaleic acid by removal of a proton from each of the carboxylic acid groups.


A dihydropterin that is 7,8-dihydropteridin-4-ol substituted at positions 2 and 6 by amino and hydroxymethyl groups respectively.


2-hydroxyglutaric acid

A 2-hydroxydicarboxylic acid that is glutaric acid in which one hydrogen alpha- to a carboxylic acid group is substituted by a hydroxy group.


ketone

A compound in which a carbonyl group is bonded to two carbon atoms: R2C=O (neither R may be H).


monoacyl-sn-glycerol 3-phosphate

An sn-glycero-3-phosphate compound having a single unspecified acyl group at either position 1 or position 2.


glycoprotein

A compound in which a carbohydrate component is covalently bound to a protein component.


(1R,2R,3R)-prephytoene diphosphate

The (1R,2R,3R)-diastereomer of prephytoene diphosphate.


A 3-chloroalanine that has S configutation at the chiral centre.


2-dehydropantoic acid

An oxo monocarboxylic acid that is 2-oxobutanoic acid in which both of the hydrogens at position 3 are substituted by methyl groups and one of the hydrogens at position 4 is substituted by a hydroxy group.


A cyclohexadienecarboxylic acid that is cyclohexa-2,4-dienecarboxylic acid which is substituted at positions 1 and 6 by hydroxy groups which are both on the same side of the plane of the cyclohexadiene ring.


BIPHENYL

A benzenoid aromatic compound that consists of two benzene rings connected by a single covalent bond. Biphenyl occurs naturally in coal tar, crude oil, and natural gas. Formerly used as a fungicide for citrus crops.


A dimethoxybenzene that is benzaldehyde substituted by methoxy groups at positions 3 and 4. It is found in peppermint, ginger, raspberry, and other fruits.


macarpine

A benzophenanthridine alkaloid that is sanguinarine bearing two methoxy substituents.


phosphoramide

A compound in which one or more of the OH groups of phosphoric acid have been replaced with an amino or substituted amino group. The term is commonly confined to the phosphoric triamides, P(=O)(NR2)3, since replacement of one or two OH groups produces phosphoramidic acids: P(=O)(OH)(NR2)2 , P(=O)(OH)2(NR2).


A glycotriaosylceramide having N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucose as the glycotriaosyl component.


A dibenzazecine alkaloid that is protopine bearing a hydroxy substituent at the 6-position.


1-alkyl-sn-glycerol 3-phosphate

An alkyl-sn-glycerol 3-phosphate in which the alkyl group is at position 1 of the sn-glycerol.


7,8-dihydro-7,8-dihydroxykynurenic acid

The 7,8-dihydro-7,8-dihydroxy derivative of kynurenic acid.


A derivative of scyllo-inositol having a guanidino group in place of the 1-hydroxy group.


A derivative of alpha-D-ribose having a phosphate group at the 5-position and a diphosphate at the 1-position.


The meso-diastereomer of butane-1,2,3,4-tetrol.


L-serine

The L-enantiomer of serine.


The anion resulting from the removal of a proton from the carboxylic acid group of 5-dehydro-4-deoxy-D-glucuronic acid.


aldehydo-D-galactose

An aldohexose that is the C-4 epimer of glucose.


eltanolone

The 3alpha-stereoisomer of 3-hydroxy-5beta-pregnan-20-one.


hexanoate

A short-chain fatty acid anion that is the conjugate base of hexanoic acid (also known as caproic acid).


aldehydo-N-acetyl-D-mannosamine

An N-acetylmannosamine in open-chain aldehyde form with D-configuration.


2-aminoacrylic acid

A 2,3-dehydroamino acid that is alanine which has been dehydrogenated to introduce a double bond between positions 2 and 3.


CARNITINE

An amino-acid betaine that is butanoate substituted with a hydroxy group at position C-3 and a trimethylammonium group at C-4.


glucotropeolin

An aralkylglucosinolic acid that consists of 1-thio-beta-D-glucopyranose attached to a 2-phenyl-N-(sulfooxy)ethanimidoyl group at the anomeric sulfur.


A dicarboxylic acid dianion obtained by the deprotonation of both the carboxy groups of adipic acid.


SCOULERINE

A berberine alkaloid isolated from  Corydalis saxicola.


10-oxocapric acid

A capric acid derivative carrying an oxo group at position 10.


A derivative of pyruvic acid carrying a 3,5-diiodo-4-hydroxyphenyl group at the 3-position.


octopamine

A member of the class of phenylethanolamines that is phenol which is substituted at the para- position by a 2-amino-1-hydroxyethyl group. A biogenic phenylethanolamine which has been found to act as a neurotransmitter, neurohormone or neuromodulator in invertebrates.


long-chain fatty alcohol

A fatty alcohol with a chain length ranging from C13 to C22.


A hydroxyquinone that is the 2,8-dihydroxy derivative of 1,4-naphthoquinone.


glyceraldehyde 3-phosphate

An aldotriose phosphate that is the 3-phospho derivative of glyceraldehyde. It is an important metabolic intermediate in several central metabolic pathways in all organisms.


D-xylulose

The D-enantiomer of xylulose.


mercaptamine

An amine that consists of an ethane skeleton substituted with a thiol group at C-1 and an amino group at C-2.


urate D-ribonucleotide

A purine ribonucleoside 5'-monophosphate consisting of 5'-xanthylic acid having an oxo group at the 8-position.


putrescine

A four-carbon alkane-alpha,omega-diamine. It is obtained by the breakdown of amino acids and is responsible for the foul odour of putrefying flesh.


PHOSPHOGLYCOLIC ACID

The O-phospho derivative of glycolic acid.


phosphatidyl-N,N-dimethylethanolamine

A phosphatidylethanolamine in which the amino group is dimethylated.


PROPIONALDEHYDE

An aldehyde that consists of ethane bearing a formyl substituent. The parent of the class of propanals.


nicotinamide

A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.


Any glycosyloxyflavone that consists of a flavonol attached to a 6-O-malonyl-beta-D-glucosyl residue at position 3 via a glycosidic linkage.


A derivative of scyllo-inositol where the 1- and 3-hydroxy groups are replaced by guanidino and amino groups respectively.


name: Glycerol 1-(9Z-octadecenoate) 2-hexadecanoate 3-octadecanoate


methylglyoxal

A 2-oxo aldehyde derived from propanal.


An estradiol that is estra-1,3,5(10)-triene substituted by hydroxy groups at positions 3 and 17 (the 17alpha stereoisomer).


O-demethylpuromycin

A derivative of puromycin lacking the O-methyl group on the tyrosyl residue.


A 2-oxo monocarboxylic acid anion resulting from the removal of the proton from the carboxy group of 2-oxooctadecanoic acid (stearic acid). The major species at pH 7.3.


stachyose

A tetrasaccharide consisting of sucrose having an alpha-D-galactosyl-(1->6)-alpha-D-galactosyl moiety attached at the 6-position of the glucose.


Photinus luciferin

A 1,3-thiazolemonocarboxylic acid consisting of 3,5-dihydrothiophene-4-carboxylic acid having a 6-hydroxybenzothiazol-2-yl group at the 2-position.


A non-proteinogenic alpha-amino acid that is arginine carrying a methyl group at position 3. It is a rare amino acid produced by Pseudomonas syringae syringae, with a strong toxicity against Pseudomonas syringae glycinea, two soybean pathogens.


caryoynencin

A bacterial polyyne with four conjugated triple bonds. It is a natural product found in the carnation pathogenBurkholderia caryophylli with strong antibacterial activity.


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.


quinolobactin

A quinolinemonocarboxylic acid that is xanthurenic acid in which the hydroxy group at position 4 is replaced by a methoxy group. It is a siderophore isolated from Pseudomonas fluorescens ATCC 17400.


N-methylputrescine

An N-monosubstituted putrescine where the N-substituent is methyl.


inuloxin A

A sesquiterpene lactone with formula C15H20O3. It is a natural product isolated from the aerial parts of Inula viscosa, a widespread Mediterranean plant known for its content of pharmacologically active metabolites. It has herbicidal, antifungal and antiamoebic activity.


A branched amino oligosaccharide that is a nonadecasaccharide derivative consisting of a linear trisaccharide of beta-D-mannose and two N-acetyl-beta-D-glucosamine residues (one of which is at the reducing end) all linked in sequence (1->4), to the mannosyl residue of which are linked (1->3) and (1->6) two N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl linear octasaccharide units.


6-FAM is 6-carboxyfluorescein, mA is 2'-O-methyl-riboadenosine, rC is ribocytidine, and Dabcyl is 4-(4-dimethylaminophenylazo)benzoic acid)


A branched amino oligosaccharide that is a henicosasaccharide derivative consisting of a linear trisaccharide of beta-D-mannose and two N-acetyl-beta-D-glucosamine residues (one of which is at the reducing end) all linked in sequence (1->4), to the mannosyl residue of which are linked (1->3) and (1->6) two beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl linear nonasaccharide units.


A branched amino oligosaccharide that is a tridecasaccharide derivative consisting of a linear trisaccharide of beta-D-mannosyl, N-acetyl-beta-D-glucosaminyl and (at the reducing end) N-acetyl-beta-D-glucosamine residues, all linked in sequence (1->4), to the mannosyl residue of which are linked (1->3) and (1->6) two beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl linear pentasaccharide units.


(R)-lactaldehyde

The (R)-stereoisomer of lactaldehyde.


virensol A

An aromatic primary alcohol that is phenol in which the hydrogens at positions 2, 3 and 4 are replaced by hydroxymethyl, (1E,3E,5E)-undeca-1,3,5-trien-1-yl, and hydroxy groups, respectively.


dutomycin

An anthracycline antibiotic of formula C44H54O17 isolated from Streptomyces species. It directly binds to the human serine protease inhibitor B6 (SERPINB6), inducing autophagy and apoptosis.


A cholestanoid that is (5alpha)-cholest-7-ene substituted by a beta-hydroxy group at position 3.


BENZALDEHYDE

An arenecarbaldehyde that consists of benzene bearing a single formyl substituent; the simplest aromatic aldehyde and parent of the class of benzaldehydes.


dimethylamine

A secondary aliphatic amine where both N-substituents are methyl.


DEOXYGUANOSINE

A purine 2'-deoxyribonucleoside having guanine as the nucleobase.


D-ribulose

The D-stereoisomer of ribulose.


heparosan N-sulfate L-iduronic acid

A heparan sulfate composed of a backbone of repeating alpha-L-iduronosyl-(1->4)-N-sulfonyl-alpha-D-glucosamine units joined by (1->4)-linkages.


cerulenin

An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.


guanidinoethyl methyl phosphate

An organic phosphate that consists of phosphoethanolamine bearing N-amidino and O-methyl substituents.


long-chain fatty aldehyde

A fatty aldehyde that has a chain length ranging from C13 to C22.


cinnamyl alcohol

A primary alcohol comprising an allyl core with a hydroxy substituent at the 1-position and a phenyl substituent at the 3-position (geometry of the C=C bond unspecified).


A hydroxy monocarboxylic acid anion that results from the deprotonation of the carboxylic acid group of 3-hydroxypyruvic acid.


A group obtained by removing the hydroxy group from the hemiacetal function of N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl-(1->6)-beta-D-mannose.


gentisic acid

A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions.


L-isoleucine

The L-enantiomer of isoleucine.


name: 9,12,15-Octadecatrienoic acid 1-[(phosphonoxy)methyl]-1,2-ethanediyl ester


BROMOXYNIL

A dibromobenzene that is 2,6-dibromophenol substituted by a cyano group at position 4.


bromochloromethane

A halomethane that is chloromethane in which one of the hydrogens has been replaced by a bromine atom.


thiomorpholine-3-carboxylic acid

A thiomorpholinemonocarboxylic acid having the carboxy group at the 3-position.


A member of the class of furans that is furan in which the hydrogen at position 2 is replaced by a hexyl group.


1-alkylglycerone 3-phosphate

A glycerone 3-phosphate having an unspecified O-alkyl substituent at the 1-position.


UDP-glucuronic acid

A UDP-sugar having alpha-D-glucuronic acid as the sugar component.


glycylglycine

A dipeptide formed from glycine residues.


5'-inosine monophosphate

A purine ribonucleoside 5'-monophosphate having hypoxanthine as the nucleobase.


L-proline

Pyrrolidine in which the pro-S hydrogen at position 2 is substituted by a carboxylic acid group. L-Proline is the only one of the twenty DNA-encoded amino acids which has a secondary amino group alpha to the carboxyl group. It is an essential component of collagen and is important for proper functioning of joints and tendons. It also helps maintain and strengthen heart muscles.


4,5-dioxopentanoic acid

A dioxo monocarboxylic acid consisting of a valeric acid core with the two oxo groups at the 4- and 5-positions.


(2E)-2-hexenyl isovalerate

A 2-hexenyl isovalerate in which the double bond adopts a trans-configuration.


An epoxy steroid that is pregn-4-ene-3,20-dione which has an epoxy group whose oxygen is attached to the 9alpha and 11alpha-positions.


cis-3-hexenyl isovalerate

A 3-hexenyl isovalerate in which the double bond adopts cis-configuration.


2-methylideneglutaric acid

A dicarboxylic acid comprising a glutaric acid core with a methylene group at the 2-position.


DIHYDROSANGUINARINE

A benzophenanthridine alkaloid obtained by selective hydrogenation of the 13,14-position of sanguinarine.


A member of the class of furans that is disulfane in which both hydrogen's are substituted by 2-methylfuran-3-yl groups. It is a flavouring agent found in meat.


geranyl diphosphate

The diphosphate of the polyprenol compound geraniol.


Dibenzothiophene substituted at positions 1 and 2 by hydroxy groups.


D-lysopine

The N(2)-(R)-1-carboxyethyl derivative of L-lysine.


A dicarboxylic acid dianion obtained by removal of a proton from both carboxy groups of (2S)-2-isopropyl-3-oxosuccinic acid.


TYROSINE METHYL ESTER

An L-tyrosyl ester that is the methyl ester of L-tyrosine.


2-butenoic acid

A butenoic acid having the double bond at position C-2.


Any 3beta-hydroxy-steroid that contains a double bond between positions 5 and 6.


MYRCENE

A monoterpene that is octa-1,6-diene bearing methylene and methyl substituents at positions 3 and 7 respectively.


A UDP-amino sugar that is UDP-N-acetyl-D-glucosamine having an beta-D-galactose-1-phospho moiety attached at position 6.


hymecromone

A hydroxycoumarin that is umbelliferone substituted by a methyl group at position 4.


SALUTARIDINE

A morphinane alkaloid from the opium poppy, in which the 5,6,8,14-tetradehydromorphinan-7-one skeleton is substituted at position 4 by a hydroxyl group, positions 3 and 6 by methoxy groups and position N17 by a methyl group. An intermediate in the biosynthesis of narcotic analgesics such as morphine and codeine.


rosmarinic acid (racemate)

The 1-carboxy-2-(2,4-dihydroxyphenyl)ethyl ester of trans-caffeic acid.


A glucosyl group obtained by removing the hydroxy group from the hemiacetal function of D-galactosyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucose.


guanidinoethane sulfonic acid

The N-amidino derivative of taurine.


L-homocysteine

A sulfur-containing amino acid consisting of a glycine core with a 2-mercaptoethyl side-chain.


A pyrrolopyrazine that is pyrrolo[1,2-a]pyrazine in which the hydrogen at position 3 is replaced by a methyl group.


METACRESOL

A cresol with the methyl substituent at position 3. It is a minor urinary metabolite of toluene.


L-glutamic 5-semialdehyde

A glutamic semialdehyde arising from formal reduction of the side-chain carboxy group of L-glutamic acid.


A secondary carboxamide resulting from the formal condensation of the carboxy group of 4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylic acid with the primary amino group of 1-[2-(aminomethyl)imidazo[1,2-a]pyridin-6-yl]-N-(cyclohexylmethyl)methanamine. It is a highly potent and selective first-in-class small molecule inhibitor of METTL3 (N6-adenosine-methyltransferase 70 kDa subunit) enzyme activity and exhibits anti-leukaemic activity.


glucose

An aldohexose used as a source of energy and metabolic intermediate.


chaetoglobosin P

An alkaloid isolated from Discosia rubi that is chaetoglobosin A with a methyl substituent on C-10.


GlyTouCan G01155JM

A composition-only glycan consisting of four hexosyl groups, five acetaminohexosyl groups and one sulfate group (identities and connectivity unknown). Composition: Hex4 HexNAc5 S1.


GlyTouCan G00390GQ

A composition-only glycan consisting of two hexosyl groups, two acetaminohexosyl groups and two N-acetyl-neuraminic acid groups (identities and connectivity unknown). Composition:  Hex2 HexNAc2 NeuAc2.


2-hydroxy-6-oxohexa-2,4-dienoic acid

A muconic semialdehyde having a hydroxy substituent at the 2-position.


GlyTouCan G01605NF

A composition-only glycan consisting of five hexosyl groups, seven acetaminohexosyl groups, one 6-deoxy-hexosyl group and two N-acetyl-neuraminic acid groups (identities and connectivity unknown). Composition: Hex5 HexNAc7 dHex1 NeuAc2.


GlyTouCan G01633XH

A composition-only glycan consisting of three hexosyl groups, three acetaminohexosyl groups and four 6-deoxyhexosyl groups (identities and connectivity unknown). Composition: Hex3 HexNAc3 dHex4.


brominated flame retardant

Any organobromine compound that is used as a flame retardant. These chemicals are widely incorporated as additives in consumer products such as electronics, vehicles, polyurethane foams etc, to make them less flammable.


GlyTouCan G01791IN

A composition-only glycan consisting of seven hexosyl groups, six acetaminohexosyl groups and one N-acetyl-neuraminic acid group (identities and connectivity unknown). Composition: Hex7 HexNAc6 NeuAc1.


GlyTouCan G02287BL

A composition-only glycan consisting of seven hexosyl groups, six acetaminohexosyl groups and two 6-deoxyhexosyl groups (identities and connectivity unknown). Composition: Hex7 HexNAc6 dHex2.


pantocin A

A member of the class of indolizines that is 3,5,6,7-tetrahydroindolizine which carries a 2-aminoacyl-4-amino-4-oxobutanoic acid, oxo, amino groups at positions 3S, 5 and 6S, respectively. It is a ribosomally encoded and post-translationally modified peptide natural product found in several species of the Pantoea genus and derived from a Glu-Glu-Asn precursor peptide.


CDP

A pyrimidine ribonucleoside 5'-diphosphate having cytosine as the nucleobase.


glycol ether

A hydroxyether which contains both an ether and alcohol functional groups. It is one of the most versatile classes of organic solvents which are commonly used in paints, cleaners, adhesives, pharmaceuticals and cosmetics.


cholate 7-sulfate(2-)

A steroid sulfate oxoanion obtained by deprotonation of the carboxylic acid and sulfate functions of cholic acid 7-sulfate; major species at pH 7.3.


glycocholate 7-sulfate(2-)

A steroid sulfate oxoanion obtained by deprotonation of the carboxylic acid and sulfate functions of glycocholic acid 7-sulfate; major species at pH 7.3.


taurocholate 7-sulfate(2-)

A steroid sulfate oxoanion obtained by deprotonation of the carboxylic acid and sulfate functions of taurocholic acid 7-sulfate; major species at pH 7.3.


chenodeoxycholate 7-sulfate(2-)

A steroid sulfate oxoanion obtained by deprotonation of the carboxylic acid and sulfate functions of chenodeoxycholic acid 7-sulfate; major species at pH 7.3.


taurochenodeoxycholate 7-sulfate(2-)

A steroid sulfate oxoanion obtained by deprotonation of the carboxylic acid and sulfate functions of taurochenodeoxycholic acid 7-sulfate; major species at pH 7.3.


perfluoroalkyl substance

A perfluorinated compound in which the carbon chain atoms are completely fluorinated.


alpha-muricholate 7-sulfate(2-)

A steroid sulfate oxoanion obtained by deprotonation of the carboxylic acid and sulfate functions of alpha-muricholic acid 7-sulfate; major species at pH 7.3.


name: phosphatidylserine amidated glycine residue(2-)


A dicarboxylic acid dianion that results from the deprotonation of both of the carboxylic acid groups of itaconic acid.


The conjugate base of tauro-alpha-muricholic acid obtained by deprotonation of the carboxylic acid function; major species at pH 7.3.


norisoprenoid

Any compound formally derived from an isoprenoid by loss of a methylene group. Norisoprenoids are a diverse class of aromatic compounds that contribute to the varietal character of many wines, especially in aromatic varieties such as Riesling.


A N-acylheptadecasphingosine in which the ceramide N-acyl group is specified as octadecanoyl.


polyfluoroalkyl substance

An organofluorine compound that has multiple fluorine atoms attached to an alkyl chain (but at least one of the carbon atoms in the chain is not fully fluorinated).


PYRAZOLE

The 1H-tautomer of pyrazole.


name: 2-Methoxy-(3 or 5 or 6)-isopropylpyrazine


mono(2-ethylhexyl) phthalate

The mono(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.


CARBON MONOXIDE

A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.


polyvinyl alcohol

A homopolymer macromolecule obtained by polymerisation of vinyl alcohol.


A member of the class of  dihydrofurans that is disulfane in which both hydrogen's are substituted by 2-methyl-4,5-dihydrofuran-3-yl groups. It is a flavouring agent found in meat.


N-isopropylammelide

A dihydroxy-1,3,5-triazine consisting of ammelide bearing an N-isopropyl substituent.


D-nopaline

An amino acid opine resulting from the formal reductive condensation of the amino group of L-arginine with the keto group of 2-oxopentanedioic acid.


A tricarboxylic acid that is the 2-oxo derivative of homocitric acid.


A 17alpha-hydroxy steroid that is the 17alpha-hydroxy derivative of progesterone.


A benzoquinone resulting from the formal oxidation of catechol.


A methylcatechol having a single methyl substituent at the 4-position. It has been isolated from Picea abies.


N-carbamoyl-D-alpha-amino acid

Any N-carbamoyl-amino acid having D-configuration.


A purine 2'-deoxyribonucleoside having adenine as the nucleobase.


bis-gamma-glutamylcystine

The dimer obtained by formal oxidative coupling of gamma-glutamylcystine.


The 7H-tautomer of purine.


A CDP-sugar in which the sugar component is 3,6-dideoxy-D-mannose.


butanoyl dihydrogen phosphate

An acyl monophosphate where the acyl groups is butanoyl.


An N(4)-glycosyl-L-asparagine having (beta-N-acetyl-D-glucosaminyl as the glycosyl component.


dTDP-D-galacturonic acid

A dTDP-sugar where the sugar component is D-galacturonic acid.


estrone

A 17-oxo steroid that is estra-1,3,5(10)-triene substituted by an hydroxy group at position 3 and an oxo group at position 17.


phosphatidylglycerol phosphate

A phosphatidylglycerol in which one of the hydroxy groups of the glycerol moiety has been converted to the corresponding dihydrogen phosphate.


A scyllo-inositol phosphate compound having the phosphate group at the 6-position, guanidino groups replacing hydroxy functions at the 1-position and an alpha-L-lyxofuranosyl residue at the 4-position.


L-sorbose

The L enantiomer of sorbose, a ketone-containing hexose (a six-carbon monosaccharide).


myo-inositol

An inositol having myo- configuration.


Latia luciferin

An apo carotenoid sesquiterpenoid that consists of a cylohexene ring substituted by methyl groups at positions 2, 6 and 6 and a (1E)-1-(formyloxy)-2-methylbut-1-en-4-yl group at position 2.


GLYCERYLPHOSPHATE

A glycerol monophosphate having the phosphate group at the 2-position.


A triply-charged monocarboxylic acid anion obtained by deprotonation of the carboxy and phospho groups of 3-phosphonopyruvic acid.


propionate

The conjugate base of propionic acid; a key precursor in lipid biosynthesis.


aldehydo-N-acyl-D-glucosamine

The open-chain form of an N-acyl-D-glucosamine.


2-isopropylmaleic acid

The 2-isopropyl derivative of maleic acid.


phloretin

A member of the class of dihydrochalcones that is dihydrochalcone substituted by hydroxy groups at positions 4, 2', 4' and 6'.


UDP-glycopeptide having N-acetylmuramoyl as the glyco portion and L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine as the peptide portion (attached via an amide bond between the amino terminus and the muramoyl carboxy group).


hexyl heptanoate

A heptanoate ester obtained by the formal condensation of the carboxy group of heptanoic acid (enanthic acid) with hexan-1-ol.


N-succinyl-LL-2,6-diaminopimelic acid

A tricarboxylic acid consisting of LL-2,6-diaminopimelic acid having a succinoyl group attached to one of the nitrogens.


A 2-hydroxy carboxylate that is the conjugate base of 3-(indol-3-yl)lactic acid.


A phosphatidylinositol 3-phosphate in which the inositol moiety is the D-myo-isomer.


A ribose monophosphate having the phosphate group at the 5-position and an amino group in place of hydroxy at the anomeric centre.


L-cysteic acid

The L-enantiomer of cysteic acid.


deacetylisoipecoside

Isoipecoside in which the acetyl group attaced to the nitrogen is replaced by hydrogen.


phosphocreatine

A phosphoamino acid consisting of creatine having a phospho group attached at the primary nitrogen of the guanidino group.


name: phosphatidylethanolamine amidated glycine zwitterion


Major microspecies at pH 7.3.


phenylsilane

An organosilicon compound that is benzene in which a hydrogen is replaced by a silyl group.


A nucleoside triphosphate(4-) obtained by global deprotonation of the triphosphate OH groups of 2-oxo-ATP; major microspecies at pH 7.3


A branched amino oligosaccharide that is a tricosasaccharide derivative comprising a linear trisaccharide of beta-D-mannose and two N-acetyl-beta-D-glucosamine residues (one of which is at the reducing end) all linked in sequence (1->4), to the mannosyl residue of which are linked two N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl  linear decasaccharide units via (1->3) and (1->6) glycosidic linkages.


homoserine lactone

A butan-4-olide having an amino substituent at the 2-position.


A member of the class of furonaphthodioxoles that is (5R,5aR,8aR)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one substituted at position 5 by a 4-hydroxy-3,5-dimethoxyphenyl group.


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.


A branched amino oligosaccharide that is a nonacosasaccharide derivative comprising a linear trisaccharide of beta-D-mannose and two N-acetyl-beta-D-glucosamine residues (one of which is at the reducing end) all linked in sequence (1->4), to the mannosyl residue of which are linked two beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl linear tridecasaccharide units via (1->3) and (1->6) glycosidic linkages.


A primary alcohol resulting from the cleavage of the phosphate group of the prodrug PF-07304814. It is an inhibitor of SARS-CoV-1 and -2 main protease (3CLpro) and exhibits potent in vitro antiviral activity.


A glycotetraosylceramide having beta-D-galactosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucose as the tetrasaccharide component.


An amino tetrasaccharide comprising a chain of 3-O-sulfo-beta-D-glucuronic acid, beta-D-galactose, N-acetyl-beta-D-glucosamine and alpha-D-mannose residues linked sequentially (1->3), (1->4) and (1->2).


A branched amino heptasaccharide consisting of three sialyl residues, two galactose residues, one N-acetylglucosamine and a glucose residue at the reducing end.


ethylzingerone

A methyl ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at positions 3 and 4 by ethoxy and hydroxy groups, respectively. It is a preservative with antimicrobial activity and a good safety profile that has been approved for use in cosmetics. It is structurally similar to zingerone, a phytochemical found in the root of the ginger plant Zingiber officinale.


FLUORESCEIN

A xanthene dye that is highly fluorescent and commonly used as a fluorescent tracer.


beta-acoradiene

A spiro compound that is 1,8-dimethyl-4-(prop-1-en-2-yl)spiro[4.5]decane that has been dehydrogenated to introduce a double bond at position 8-9 (the 1R,4S,5R isomer).


alpha-acoradiene

A spiro compound that is 1,8-dimethyl-4-(prop-1-en-2-yl)spiro[4.5]decane that has been dehydrogenated to introduce a double bond at position 8-9 (the 1R,4S,5S isomer).


lycosantalene

A carbotricyclic compound that is tricyclo[2.2.1.0(2,6)]heptane carrying methyl groups at position 1 and 7 and a (6Z)-2,6-dimethylnona-2,6-dien-9-yl group at position 7. It is a diterpene produced by a terpenoid biosynthetic gene cluster in tomatoes.


A sesquiterpenoid that is cyclodeca-2,7-diene substituted by methyl, hydroxy, isoproyl, and methyl groups at positions 1, 1, 4S and 7, respectively.


beta-elemol

A sesquiterpene.


bicycloelemene

A carbobicyclic compound that is 7,7-dimethylbicyclo[4.1.0]heptane substituted by prop-1-en-2-yl, ethenyl and methyl groups at positions 2, 3 and 3, respectively (the 1R,2R,3S,6R-stereoisomer). It is a sesquiterpene isolated from the leaves of several plant species.


longiborneol

A sesquiterpene.


(+)-thalianatriene

A sesterterpene with formula C25H40 that is produced by a sesterterpene synthase gene from the plant Arabidopsis thaliana.


(-)-retigeranin B

A sesterterpene produced by a sesterterpene synthase gene identified in the plant Arabidopsis thaliana.


astellifadiene

A sesterterpene with formula C25H40 that is produced by a terpene synthase gene from Emericella variecolor NBRC 32302 which is heterologously expressed in Aspergillus oryzae NSAR1.


An indole alkaloid that is the enol tautomer of geissoschizine, which is also dehydrogenated at the 4,21-position.


name: C-terminal amino acid-glycine residue(1-)


name: C-terminal amino acid- phosphatidylethanolamine amidated glycine residue(1-)


name: C-terminal amino acid- phosphatidylserine amidated glycine residue(2-)


bictegravir

A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2R,5S,13aR)-8-hydroxy-7,9-dioxo-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxylic acid with the amino group of 2,4,6-trifluorobenzylamine. It is a second-generation integrase strand transfer inhibitor (INSTI) and used (as its sodium salt) for the treatment of HIV-1.


cabotegravir

A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (3S,11aR)-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxylic acid with the amino group of 2,4-difluorobenzylamine. Used (as its sodium salt) for treatment of HIV-1.


A retinoid that is 9-cis-retinoic acid in which the carboxy proton has been replaced by a beta-D-glucuronyl group. It is a major metabolite of 9-cis-retinoic acid.


A member of the class of furans that is furan in which the hydrogen at position 3 is replaced by a methyl group. It is a chemical that is produced in foods during food processing and preservation techniques that involve heat treatment such as cooking and pasteurization.


An organic anion that is the conjugate base of cabotegravir, obtained by deptotonation of the 6-hydroxy group.


L-phenylalanine

The L-enantiomer of phenylalanine.


A branched amino oligosaccharide that is a dodecasaccharide derivative consisting of a linear trisaccharide of beta-D-mannose and two N-acetyl-beta-D-glucosamine residues all linked in sequence (1->4), to the mannosyl residue of which are linked two N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl linear tetrasaccharide units [linked (1->3) and (1->6)], while to the N-acetyl-beta-D-glucosamine residue at the reducing end is linked (1->6) an alpha-L-fucose residue.


ANILINE

A primary arylamine in which an amino functional group is substituted for one of the benzene hydrogens.


An organic anion that is the conjugate base of bictegravir, obtained by deptotonation of the 8-hydroxy group.


UDP-sugar

A pyrimidine nucleotide-sugar having UDP as the nucleotide component attached to an unspecified sugar via an anomeric diphosphate linkage.


An organic heterotetracyclic compound that is podophyllotoxin in which the methyl ether group at position 4 of the trimethoxyphenyl group has been cleaved to afford the corresponding phenol.


tetrachloroethylene

A chlorocarbon that is tetrachloro substituted ethene.


glucaric acid

A hexaric acid derived by oxidation of sugar such as glucose with nitric acid.


A pyrazoloquinoline that is 2,5-dihydropyrazolo[4,3-c]quinolin-3-one which is substituted at position 2 by a 5-butyl-2-thienyl group.


pentadecanal

A long-chain fatty aldehyde that is pentadecane carrying an oxo substituent at position 1. It is a component of essential oils from plants like Solanum erianthum and Cassia siamea.


morphine

A morphinane alkaloid that is a highly potent opiate analgesic psychoactive drug. Morphine acts directly on the central nervous system (CNS) to relieve pain but has a high potential for addiction, with tolerance and both physical and psychological dependence developing rapidly. Morphine is the most abundant opiate found in Papaver somniferum (the opium poppy).


maltose

A glycosylglucose consisting of two D-glucopyranose units connected by an alpha-(1->4)-linkage.


A member of the class of furanochromones that is 5H-furo[3,2-g][1]benzopyran carrying an oxo group a position 5.


lufotrelvir

An indolecarboxamide resulting from the formal condensation of the carboxy group of 4-methoxy-1H-indole-2-carboxylic acid with the primary amino group of N-[(2S)-3-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]-4-(phosphonooxy)butan-2-yl]-L-leucinamide. It is the phosphate prodrug of PF-00835231, an anticoronaviral agent.


An alkyl,acyl-sn-glycero-3-phospho-1D-myo-inositol-5-phosphate in which unspecified alkyl and acyl groups are located at positions sn-1 and sn-2 respectively. Major microspecies at pH 7.3


FENOXASULFONE

A dichlorobenzene that is benzene in which the hydrogens at positions 1, 2, 4 and 5 are replaced by [(5,5-dimethyl-4,5-dihydro-1,2-oxazol-3-yl)sulfonyl]methyl, chloro, ethoxy and chloro groups, respectively. It is a rice herbicide developed by Kumiai Chemical Industry Co. Ltd which displays excellent herbicidal activity against Echinochloa spp. and other annual weeds.


2-oxohexanoic acid

A straight-chain fatty acid consisting of hexanoic acid having an oxo group at position 2.


name: 3'-end uridine-uridine 2',3'-cyclophosphate(3-) residue


sialic acid

An N-acetylneuraminic acid that is keto-neuraminic acid in which one of the hydrogens of the amino group is replaced by an acetyl group.


aceneuramate

An N-acetylneuraminate that is the conjugate base of aceneuramic acid arising from the deprotonation of the carboxy group. Major microspecies at pH 7.3.


An ethyl ester resulting from the formal condensation of the carboxy group of 3-amino-4-(cyclohexylamino)benzoic acid with ethanol. It is a potent inhibitor of ferroptosis, a distinct non-apoptotic form of cell death caused by lipid peroxidation. It is also a radical-trapping antioxidant and has the ability to reduce the accumulation of lipid peroxides and chain-carrying peroxyl radicals.


A branched amino oligosaccharide that is an icosasaccharide derivative consisting of a linear trisaccharide of beta-D-mannose and two N-acetyl-beta-D-glucosamine residues all linked in sequence (1->4), to the mannosyl residue of which are linked two N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl linear octasaccharide units [linked (1->3) and (1->6)], while to the N-acetyl-beta-D-glucosamine residue at the reducing end is linked (1->6) an alpha-L-fucose residue.


An ethyl ester resulting from the formal condensation of the carboxy group of 3-(benzylamino)-4-(cyclohexylamino)benzoic acid with ethanol. It is a potent inhibitor of ferroptosis induced by erastin in HT-1080 human fibrosarcoma cells (EC50 = 6 nM).


An ethyl ester resulting from the formal condensation of the carboxy group of 4-[(adamantan-1-yl)amino]-3-{(Z)-[(pyrimidin-5-yl)methylidene]amino}benzoic acid with tert-butanol. It is an inhibitor of ferroptosis induced by erastin in HT-1080 and NIH3T3 cells when used at a concentration of 1 muM.


An azaspiro compound that is 1'H-spiro[piperidine-4,2'-quinoxaline] in which the hydrogen at position 3' is replaced by a (3-chlorobenzyl)amino group. It is a potent inhibitor of ferroptosis.


An organic heterotetracyclic compound that is 1H-indole which is ortho-fused to a 2H-1-benzothiopyran group at positions 2-3. It is an inhibitor of 15-lipoxygenase that limits atherosclerotic lesion development in rabbits.


A peptidomimetic that is an inhibitor of ferroptosis and prevents the onset of motor decline in a mouse model for Huntington's disease.


pyridoxal

A pyridinecarbaldehyde that is pyridine-4-carbaldehyde bearing methyl, hydroxy and hydroxymethyl substituents at positions 2, 3 and 5 respectively. The 4-carboxyaldehyde form of vitamin B6, it is converted into pyridoxal phosphate, a coenzyme for the synthesis of amino acids, neurotransmitters, sphingolipids and aminolevulinic acid.


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.


TALAROCONVOLUTIN A

An octahydronaphthalene with formula C32H41NO3. It is a fungal metabolite isolated from Talaromyces convolutus and is an inducer of ferroptosis in colorectal cancer cells.


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 branched amino oligosaccharide that is a tetracosasaccharide derivative consisting of a linear trisaccharide of beta-D-mannose and two N-acetyl-beta-D-glucosamine residues all linked in sequence (1->4), to the mannosyl residue of which are linked two N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl linear decasaccharide units [linked (1->3) and (1->6)], while to the N-acetyl-beta-D-glucosamine residue at the reducing end is linked (1->6) an alpha-L-fucose residue.


A beta-carboline that is 2,3,4,4a,9,9a-hexahydro-1H-beta-carboline in which the hydrogens at positions 1, 2 and 3 are replaced by 4-(methoxycarbonyl)phenyl, chloroacetyl and methoxycarbonyl groups, respectively (the 1S,2R stereoisomer). It is a potential antineoplastic agent which triggers ferroptosis by inactivating the glutathione peroxidase 4 (GPX4) enzyme.


An alpha-amino-acid cation that is the N(6)-trimethyl derivative of L-lysine.


A branched amino oligosaccharide that is a hexacosasaccharide derivative consisting of a linear trisaccharide of beta-D-mannose and two N-acetyl-beta-D-glucosamine residues all linked in sequence (1->4), to the mannosyl residue of which are linked two beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl linear undecasaccharide units [linked (1->3) and (1->6)], while to the N-acetyl-beta-D-glucosamine residue at the reducing end is linked (1->6) an alpha-L-fucose residue.


A branched amino oligosaccharide that is an octadecasaccharide derivative consisting of a linear trisaccharide of beta-D-mannose and two N-acetyl-beta-D-glucosamine residues all linked in sequence (1->4), to the mannosyl residue of which are linked a beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl linear pentasaccharide group via a (1->3) linkage and a beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->2)-[beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->6)]-alpha-D-mannosyl branched nonasaccharide group via a (1->6) linkage, while to the N-acetyl-beta-D-glucosamine residue at the reducing end is linked (1->6) an alpha-L-fucose residue.


name: 3'-end ribonucleotide 2'-phosphate(3-) residue


A nerolidol in which the double bond at position 6 adopts a cis-configuration.


An  acetylspermine carrying an acetyl group at position N(1).


A sesquiterpene that is (9aS)-5,6,7,8,9,9a-hexahydro-1H-benzo[7]annulene substituted by methyl groups at positions 3, 5, 5 and 9R. It is a pheromone produced by males of several Phyllotreta species.


A sesquiterpenoid that is bisabolane having double bonds at positions 2 and 9 as well as a hydroxy substituent at position 1 (the 1S,6S,7R-stereoisomer). It is a male produced sex pheromone of Tibraca limbativentris.


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.


D-glucosamine

An amino sugar whose structure comprises D-glucose having an amino substituent at position 2.


name: 1alpha-Hydroxy-25,26,27-trinorvitamin D3 24-carboxylic acid


D-sorbose

Any form of sorbose that has D-configuration.


A monocarboxylic acid anion that is the conjugate base of N-(3,4-dichlorophenyl)malonamic acid arising from deprotonation of the carboxy group.


A 5'-deoxyribonucleoside compound having adenosine as the nucleobase.


Any cucurbitacin whose C(23)-C(24) double bond has been reduced.


A dicarboxylic acid dianion that results from the removal of a proton from both of the carboxylic acid groups of 3-hydroxy-3-methylglutaric acid.


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.


TRANS-PHYTOL

A diterpenoid that is hexadec-2-en-1-ol substituted by methyl groups at positions 3, 7, 11 and 15.


N-benzoylanthranilate

A benzoate that is the conjugate base of N-benzoylanthranilic acid arising from deprotonation of the carboxy group.


name: 1beta,2alpha,3beta,19alpha-Tetrahydroxy-12-ursen-28-oic acid 28-O-[b-D-Glucopyranosyl-(1->2)-b-D-glucopyranosyl] ester


chorismic acid

The (3R,4R)-stereoisomer of 5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid.


penicillin G

Any member of the group of substituted penams containing two methyl substituents at position 2, a carboxylate substituent at position 3 and a carboxamido group at position 6.


name: Ethylene oxide/propylene oxide copolymer


A CDP-sugar having 3,6-dideoxy-D-glucose as the sugar component.


di-1-propenyl sulfide

An organic sulfide that is hydrogen sulfide substituted by two prop-1-en-1-yl groups. It is a volatile constituent found in garlic and onions.


An L-ornithine compound having an acyl substituent at the N(5)-position.


The simplest member of the class of 4'methoxyisoflavones that is isoflavone substituted by a methoxy group at position 4'.


cetraxate

A cyclohexanecarboxylate ester that consists of 4-(2-carboxyethyl)phenyl cyclohexanecarboxylate bearing an aminomethyl substituent at the 4-position.


A 2-aminohexano-6-lactam derived from L-lysine.


A purine ribonucleoside 5'-monophosphate having guanine as the nucleobase.


A nitrile that is acetonitrile in which one of the hydrogens has been replaced by a p-chlorophenyl group.


testosterone

An androstanoid having 17beta-hydroxy and 3-oxo groups, together with unsaturation at C-4-C-5..


D-aldohexose 6-phosphate

Any D-aldose having a six-carbon chain with a phosphate group at C-6.


(cyclohexylmethyl)pyrazine

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


linoleic acid

An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.


(R)-mandelamide

A mandelamide in which the stereocentre at position 2 has R-configuration.


16beta-hydroxy steroid

A 16-hydroxy steroid in which the hydroxy group at position 16 has a beta-configuration.


The parent of the class of 2-acetamidofluorenes, being an ortho-fused polycyclic arene that consists of 9H-fluorene bearing an acetamido substituent at position 2. It is a carcinogenic and mutagenic derivative of fluorene.


A thiophene that is substituted by acetyl and methyl groups at positions 2 and 5, respectively.


sulfite

A sulfur oxoanion that is the conjugate base of hydrogen sulfite (H2SO3).


D-altronate

Conjugate base of D-altronic acid.


cytidine 5'-monophosphate

A pyrimidine ribonucleoside 5'-monophosphate having cytosine as the nucleobase.


QUINOLINE

The simplest member of the quinoline class of compounds, comprising a benzene ring ortho fused to C-2 and C-3 of a pyridine ring.


D-ribulose 5-phosphate

The D-enantiomer of ribulose 5-phosphate that is one of the end-products of the pentose phosphate pathway.


An N-(3,7-dimethylocta-2,6-dien-1-yl)cyclopropanecarboxamide in which the double bond at position 2 adopts an E-configuration.


D-ASPARTATE

The D-enantiomer of aspartic acid.


2-oxooctanoic acid

A 2-oxo monocarboxylic acid that is octanoic acid carrying an oxo group at position 2.


hypoxanthine

A purine nucleobase that consists of purine bearing an oxo substituent at position 6.


D-mannose 6-phosphate

A mannose phosphate in which the phosphate group is attached to position 6.


MACROCIN

A macrolide antibiotic that is tylonolide having mono- and diglycosyl moieties attached to two of its hydroxy groups.


An indole alkaloid obtained by selective hydrogenation of the 1,2-position of vomilenine.


norsalsolinol

An isoquinolinol that is 1,2,3,4-tetrahydroisoquinoline substituted by hydroxy groups at positions 6 and 7. It is present in the dopamine-rich areas of the human brain, including the substantia nigra.


(2S)-2-hydroxy monocarboxylic acid

A 2-hydroxy monocarboxylic acid in which the carbon at position 2 has (S)-configuration.


ethyl 3-(2-furyl)acrylate

A member of the class of furans that is furan substituted by a 3-ethoxy-3-oxoprop-1-en-1-yl group at position 2.


D-glyceraldehyde

The D-enantiomer of glyceraldehyde.


isovitexin 2''-O-beta-D-glucoside

A disaccharide derivative that is the 2"-O-beta-D-glucosyl derivative of isovitexin .


porphobilinogen

A dicarboxylic acid that is pyrole bearing aminomethyl, carboxymethyl and 2-carboxyethyl substituents at positions 2, 3 and 4 respectively.


An indole alkaloid obtained by formal acetylation of the 17-hydroxy group of norajmaline.


3-(4-hydroxyphenyl)lactic acid

A 2-hydroxy carboxylic acid that is lactic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.


O-acylcarnitine

Any carboxylic ester obtained by the O-acylation of carnitine.


A 1-pyrroline-5-carboxylate resulting from the removal of the proton from the carboxy group of (S)-1-pyrroline-5-carboxylic acid.


A monoglyceride in which the acyl substituent is located at position 2.


name: cis- and trans-Ethyl 2,4-dimethyl-1,3-dioxolane-2-acetate


peptidylproline (omega=0)

The cis isomer of the L-proline  peptide bond.


THEANINE

A N(5)-alkylglutamine where the alkyl group is ethyl. It has been isolated from green tea.


cis-caffeic acid

The cis-isomer of caffeic acid.


A member of the class of oxindoles that is oxindole (1,3-dihydro-2H-indol-2-one) in which one of the hydrogens at position 3 has been replaced by a methyl group.


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


A 3-chloroalanine that has R configutation at the chiral centre.


An indanone that consists of 2,3-dihydro-1H-indene substituted by an oxo group at position 1.


4-pyridoxic acid

A methylpyridine that is 2-methylpyridine substituted by a hydroxy group at C-3, a carboxy group at C-4, and a hydroxymethyl group at C-5. It is the catabolic product of vitamin B6 and is excreted in the urine.


3-(imidazol-5-yl)pyruvic acid

An oxo carboxylic acid that is pyruvic acid in which one of the methyl hydrogens has been replaced by an imidazol-5-yl group.


trans,trans-farnesyl diphosphate

The trans,trans-stereoisomer of farnesyl diphosphate.


A glyceride in which any one of the R groups (position not specified) is an acyl group while the remaining two R groups can be either H or alkyl groups.


name: 3,4-Dihydroxyphenyllactic acid methyl ester


10-hydroxycapric acid

A 10-carbon, omega-hydroxy fatty acid, shown to be the preferred hydroxylation product (together with the 9-OH isomer) of capric acid in biosystems, and used as a standard in lipid assays; reported to have cytotoxic effects.


aldehydo-N-acetyl-D-glucosamine

The open-chain form of N-acetyl-D-glucosamine.


R'C(R)S-S(R)CR'

Any disulfide with structure R'C(R)S-S(R)CR' in which R and R' can be =S or =O, or a variety of other groups.


A hydroxyindole that is 1H-indole-5,6-diol substituted by a 5,6-dihydroxy-1H-indol-3-yl group at position 3.


2-(hydroxymethyl)-4-oxobutanoic acid

A 4-oxo monocarboxylic acid that is 4-oxobutanoic acid which is substituted by a hydroxymethyl group at position 2.


pentanoic acid

A straight-chain saturated fatty acid containing five carbon atoms.


name: (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform B (protein)


A heparan sulfate having an N-acetyl-alpha-D-glucosaminyl residue at the non-reducing end. The heparan sulfate part consists of a variably sulfated repeating disaccharide unit.


N-[(S)-lactoyl]-L-phenylalanine

A L-phenylalanine derivative that is L-phenylalanine in which the amino group is replaced by a [(2S)-2-hydroxypropanoyl]amino group. It is a metabolite produced as a result of exercise in mice, racehorses, and humans which suppresses feeding and obesity.


DIADENOSINE TETRAPHOSPHATE

A diadenosyl tetraphosphate compound having the two 5'-adenosyl residues attached at the P(1)- and P(4)-positions.


The anion resulting from the removal of a proton from the carboxylic acid group of 1-pyrroline-2-carboxylic acid.


3-hydroxy-L-aspartate residue

An anionic amino-acid residue resulting from the deprotonation of the carboxy group of a 3-hydroxy-L-aspartic acid residue.


A glycosyl glycoside which is an intermediate in the breakdown of sucrose. The structure is that of sucrose in which the glucosyl 3-hydroxy group has been reduced to a keto group.


trimethylsulfonium

A sulfonium compound in which the substituents on sulfur are three methyl groups. It is found in the midgut gland of the sea hare, Aplysia brasiliana, and exhibits probable ability to inhibit cholinergic responses.


A carboxyalkyl phosphate that is mevalonic acid phosphorylated at position 5.


METHYLSULFANYLMETHANE

A methyl sulfide in which the sulfur atom is substituted by two methyl groups. It is produced naturally by some marine algae.


p-NITROPHENYLPHOSPHATE

An aryl phosphate resulting from the mono-esterification of phosphoric acid with 4-nitrophenol.


L-homocitrulline

A L-lysine derivative that is L-lysine having a carbamoyl group at the N(6)-position. It is found in individuals with urea cycle disorders.


A monocarboxylic acid that is phenylacetic acid in which the hydrogen at position 3 on the benzene ring is replaced by a hydroxy group.


pilosin

A dimethoxyflavone that is flavone carrying hydroxy groups at positions 5, 7, and 8, and methoxy groups at positions 4' and 6.


geraniol

A monoterpenoid consisting of two prenyl units linked head-to-tail and functionalised with a hydroxy group at its tail end.


cis-4-coumaric acid

The cis-form of 4-coumaric acid.


A C4-dicarboxylate resulting from the removal of a proton from both carboxylic acid groups of methylmalonic acid.


UDP-L-rhamnose

A UDP-rhamnose in which the rhamnose component has L-configuration.


dithioerythritol

The meso-diastereomer of 1,4-dimercaptobutane-2,3-diol; a sulfur-containing sugar derived from the monosaccharide erythrose; and an epimer of dithiothreitol.


D-iditol

The D-enantiomer of iditol.


THIOCTIC ACID AMIDE

A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of lipoic acid with ammonia.


11H-benzo[a]fluoren-11-ylacetic acid

A carbotetracyclic compound that is 11H-benzo[a]fluorene substituted by a carboxymethyl group at position 11.


A galactonolactone that is 3,4-dihydroxydihydrofuran-2(3H)-one substituted by a 1,2-dihydroxyethyl group at position 5 (the 3S,4S,5R-isomer).


phaseollidin hydrate

A member of the class of pterocarpans that is phaseollidin in which the prenyl group is replaced by a 3-hydroxy-3-methylbutyl group.


GDP-D-mannuronate

A nucleotide-sugar oxoanion obtained by deprotonation of the diphosphate OH groups of GDP-D-mannuronic acid; major species at pH 7.3.


A 2-oxo monocarboxylic acid anion that is the conjugate base of (4-bromophenylsulfanyl)pyruvic acid, arising from deprotonation of the carboxy group.


clenbuterol

A substituted aniline that is 2,6-dichloroaniline in which the hydrogen at position 4 has been replaced by a 2-(tert-butylamino)-1-hydroxyethyl group.


A 1-alkyl-2,3-diacylglycerol in which the acyl group at position 2 is specified as acetyl.


estrone sulphate

A steroid sulfate that is the 3-sulfate of estrone.


aminomalonic acid

An amino dicarboxylic acid that is  malonic acid in which one of the methylene hydrogens has been replaced by an amino group.


A glycerophosphoethanolamine compound having an alk-1-enyl substituent at the 1-position and an acyl substituent at the 2-position.


uracil-5-carboxylic acid

A pyrimidinemonocarboxylic acid that is uracil carrying a carboxy group at position 5.


aldehyde

A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.


enol-oxaloacetate

A C4-dicarboxylate resulting from the removal of a proton from both carboxylic acid groups of enol-oxaloacetic acid.


cystathionine

A modified amino acid generated by enzymic means from L-homocysteine and L-serine.


homocystine

An organic disulfide obtained by oxidative dimerisation of homocysteine.


SCOPOLETIN

A hydroxycoumarin that is umbelliferone bearing a methoxy substituent at position 6.


CYCLIC ADENOSINE MONOPHOSPHATE

A 3',5'-cyclic purine nucleotide having having adenine as the nucleobase.


A hydroxyaurone that is aurone substituted by a hydroxy group at position 6 and a methylenedioxy group across positions 4 and 5 respectively.


O-palmitoyl-L-carnitine

An O-acyl-L-carnitine in which the acyl group is specified as palmitoyl (hexadecanoyl).


Glutathione substituted on sulfor by a 2-hydroxyacyl group.


A catechin that is (-)-epicatechin in which the hydroxy group at position 4' is replaced by a methoxy group. It is a metabolite of (-)-epicatechin.


glycolic acid

A 2-hydroxy monocarboxylic acid that is acetic acid where the methyl group has been hydroxylated.


hydrogen donor

A molecular entity that can undergo oxidation by the loss of hydrogen atom(s).


The 7alpha-hydroxy derivative of cholesterol.


2-methylpropanal oxime

An aldoxime derived from 2-methylpropanal.


A doubly-charged N-acyl-D-alpha-amino acid anion resulting from removal of protons from both carboxy groups of any N-acyl-D-glutamic acid.


An alpha-D-galactoside having a 1D-myo-inositol substituent at the anomeric position.


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.


7,8-dihydroxykynurenic acid

A hydroxyquinoline that is kynurenic acid in which the hydrogens at positions 7 and 8 are replaced by hydroxy groups.


METHYLTHIOADENOSINE

Adenosine with the hydroxy group at C-5' substituted with a methylthio (methylsulfanyl) group.


chromotropic acid

A naphthalenesulfonic acid that is naphthalene-2,7-disulfonic acid substituted by hydroxy groups at positions 4 and 5.


Phosphatidylglycerol substituted at O-3 by a L-alanyl group.


cyanide

A pseudohalide anion that is the conjugate base of hydrogen cyanide.


L-gamma-glutamyl-L-cysteine

A molecular entity formed when L-cysteine amino group binds to the gamma-carbonyl of L-glutamic acid.


phosphatidylglycerol

A glycerophosphoglycerol that is glycerol in which the hydrogen of one of the primary hydroxy groups has been replaced by a phosphatidyl group.


N-methyl-L-alanine

A methyl-L-alanine in which one of the the amino hydrogen of L-alanine is replaced by a methyl group.


alditol

A carbohydrate that is an acyclic polyol having the general formula HOCH2[CH(OH)]nCH2OH (formally derivable from an aldose by reduction of the carbonyl group).


Any purine bearing an alkylamino substituent at the 6-position.


A phosphatidylinositol 4-phosphate having 1D-myo-configuration.


A galloyl-beta-D-glucose compound having four galloyl groups in the 1-, 2-, 3- and 6-positions.


kievitone hydrate

A hydroxyisoflavanone that is isoflavanone substituted by hydroxy groups at positions 5, 7, 2' and 4' and  a 3-hydroxy-3-methylbutyl group at position 8.


ACETYLGLUTAMIC ACID

An N-acyl-L-amino acid that is L-glutamic acid in which one of the amine hydrogens is substituted by an acetyl group.


L-arabinopyranose

The six-membered ring form of L-arabinose.


allantoate

A monocarboxylic acid anion that is the  conjugate base of allantoic acid.


KYOTORPHIN

A dipeptide composed of L-tyrosine and L-arginine joined by a peptide linkage.


An octadeca-9,11-dienoate that is the conjugate base of 9-cis,11-trans-octadecadienoic acid, formed by deprotonation of the carboxylic acid functional group.


methyl beta-D-galactoside

A beta-D-galactopyranoside having a methyl substituent at the anomeric position.


1-phospho-alpha-D-galacturonic acid

An uronic acid phosphate that is alpha-D-galacturonic acid carrying a phosphate group at position 1.


hydrogencarbonate

The carbon oxoanion resulting from the removal of a proton from carbonic acid.


(E)-indol-3-ylacetaldehyde oxime

An indol-3-ylacetaldehyde oxime in which the oxime moiety has E configuration.


A hexadienal that is hexa-2,5-dienal substituted by a an isopropyl group at position 5 and a methy group at position 2 (the 2Z-stereoisomer).


alginic acid

A linear copolymer macromolecule composed of homopolymeric blocks of 1->4-linked beta-D-mannuronic acid and alpha-L-guluronic acid residues, covalently linked together in different sequences or blocks.


5-aminolevulinic acid

The simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used (in the form of the hydrochloride salt)in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp.


guanosine 5'-diphosphate

A  purine ribonucleoside 5'-diphosphate resulting from the formal condensation of the hydroxy group at the 5' position of guanosine with pyrophosphoric acid.


PHOSPHORYLETHANOLAMINE

The ethanolamine mono-ester of phosphoric acid, and a metabolite of phospholipid metabolism. This phosphomonoester shows strong structural similarity to the inhibitory neurotransmitter GABA, and is decreased in post-mortem Alzheimer's disease brain.


PHASEOLLIDIN

A member of the class of pterocarpans that is (6aR,11aR)-pterocarpan substituted by hydroxy groups at positions 3 and 9 and a prenyl group at position 10.


QUERCITRIN

A quercetin O-glycoside that is quercetin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage.


L-cysteine

An optically active form of cysteine having L-configuration.


cytidine

A pyrimidine nucleoside in which cytosine is attached to ribofuranose via a beta-N(1)-glycosidic bond.


A phthalate that is the dianion obtained by the deprotonation of both the carboxy groups of phthalic acid.


A nitrile that is acetonitrile where one of the methyl hydrogens is substituted by a 1H-indol-3-yl group.


uracil

A common and naturally occurring pyrimidine nucleobase in which the pyrimidine ring is substituted with two oxo groups at positions 2 and 4. Found in RNA, it base pairs with adenine and replaces thymine during DNA transcription.


An  N-acetyl-D-glucosaminyl group obtained formally by removal of the hydroxy group from the hemiacetal function of beta-D-galactosyl-(1->4)-N-acetyl-D-glucosamine.


biochanin A

A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at position 5 and a methoxy group at position 4'. A phytoestrogen, it has putative benefits in dietary cancer prophylaxis.


An organophosphate oxoanion that is the trianion obtained by removal of the three protons from the diphosphate group of 2-trans,6-trans-farnesyl diphosphate.


toluene

The simplest member of the class toluenes consisting of a benzene core which bears a single methyl substituent.


betacarotene

A cyclic carotene obtained by dimerisation of all-trans-retinol. A strongly-coloured red-orange pigment abundant in plants and fruit and the most active and important provitamin A carotenoid.


linalool

A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum.


N-(long-chain-fatty-acyl)-L-glutamate

A dicarboxylic acid dianion obtained by deprotonation of the carboxy groups of any N-(long-chain-fatty-acyl)-L-glutamic acid; major species at pH 7.3.


A hexadecenal containing a double bond at position 2 (the trans-stereoisomer).


CoA-glutathione

An organic disulfide arising from oxidative coupling of the thiol functions of coenzyme A and glutathione.


The furanose form of gulonolactone having L-configuration.


OCTANE

A straight chain alkane composed of 8 carbon atoms.


gemcitabine

A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.


An N(5)-alkylglutamine where the alkyl group is specified as methyl.


maltooligosaccharide

A glucooligosaccharide derived from glucose monomers linked via alpha-D-1,4 bonds as in maltose.  The term is commonly applied to the series of linear oligosaccharides composed of two, three, four, five and six such units of glucose.


hydroquinone

A benzenediol comprising benzene core carrying two hydroxy substituents para to each other.


inosine

A purine nucleoside in which hypoxanthine is attached to ribofuranose via a beta-N(9)-glycosidic bond.


A  hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4.


The pteridine that is lumazine substituted with methyl groups at C-6 and -7 and with a 1-D-ribityl group on N-8.


An amino phenol (one of the three possible isomers) which has the single amino substituent located para to the phenolic -OH group.


An L-lysine derivative that is L-lysine in which one of the hydrogens attached to N(6) is substituted by a methyl group.


2-formylbenzoic acid

An aldehydic acid which consists of benzoic acid substituted by a formyl group at position 2. Metabolite of ampicillin phthalidyl ester.


iodine

Molecule comprising two covalently bonded iodine atoms with overall zero charge..


D-aldohexose

Any D-aldose having a chain of six carbon atoms in the molecule.


3-nitroacrylic acid

An alpha,beta-unsaturated monocarboxylic acid that is acrylic acid in which one of the hydrogens at position 3 is replaced by a nitro group.


A dihydroxy monocarboxylic acid anion that is the conjugate base of (3,4-dihydroxyphenyl)acetic acid, arising from deprotonation of the carboxy group.


all-trans-heptaprenyl diphosphate

An all-trans-polyprenyl diphosphate composed from seven isoprenyl units.


name: Aromadendrin 4'-methyl ether 7-rhamnoside


A class of galactoglycerolipids that consists of any 1,2-diacyl-sn-glycerol having a beta-D-galactosyl residue attached at position 3.


vitamin A palmitate

An all-trans-retinyl ester obtained by formal condensation of the carboxy group of palmitic (hexadecanoic acid) with the hydroxy group of all-trans-retinol. It is used in cosmetic products to treat various skin disorders such as acne, skin aging, wrinkles, dark spots, and also protect against psoriasis.


L-fuculose

A a deoxyketohexose comprising L-tagatose with the hydroxy group at position 6 replaced by hydrogen.


FERULATE

A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 3 and 4 respectively on the phenyl ring.


flavin mononucleotide

A flavin mononucleotide that is riboflavin (vitamin B2) in which the primary hydroxy group has been converted to its dihydrogen phosphate ester.


DEOXYURIDINE MONOPHOSPHATE

A pyrimidine 2'-deoxyribonucleoside 5'-monophosphate having uracil as the nucleobase.


cyclomaltodextrin

A cyclic oligosaccharide comprising a ring of D-glucose units linked by alpha-(1->4) glycosidic bonds.


dUTP

A deoxyuridine phosphate having a triphosphate group at the 5'-position.


citraconic acid

A dicarboxylic acid consisting of maleic acid having a methyl substituent at the 2-position.


An amino aldehyde that is acetaldehyde in which one of the hydrogens of the methyl group has been replaced by an amino group.


kanamycin

Kanamycin is a naturally occurring antibiotic complex from Streptomyces kanamyceticus that consists of several components: kanamycin A, the major component (also usually designated as kanamycin), and kanamycins B, C, D and X the minor components.


A linear tetrasaccharide composed of four D-mannose units, joined by alpha-linkages.


nitrate

A nitrogen oxoanion formed by loss of a proton from nitric acid. Principal species present at pH 7.3.


name: (-)-Epigallocatechin 3-gallate 7-glucoside 4"-glucuronide


guanosine 3',5'-bis(diphosphate)

A guanosine bisphosphate having diphosphate groups at both the 3' and 5'-positions.


2-hexenyl isovalerate

A fatty ester resulting from the formal condensation of the carboxy group of isovaleric acid with the hydroxy group of 2-hexen-1-ol.


A member of the class of piperidines that is piperidine substituted by (4-carboxyphenyl)methyl and {[(1R,2S)-2-phenylcyclopropyl]amino}methyl groups at positions 1 and 4, respectively. It is a potent and irreversible inhibitor of lysine specific demethylase 1 (LSD1, also known as KDM1A). It was under clinical investigation for the treatment of acute myeloid leukaemia and small cell lung carcinoma.


3-(4-morpholinylsulfonyl)-benzoic acid (2E)-2-[1-(5-chloro-2-hydroxyphenyl)ethylidene]hydrazide


A (6Z)-nerolidol in which the hydroxy group at positon 3 adopts an R-configuration.


NEROLIDIOL

A (6Z)-nerolidol in which the hydroxy group at positon 3 adopts an S-configuration.


LANPERISONE

A 2-methyl-3-(pyrrolidin-1-yl)-1-[4-(trifluoromethyl)phenyl]propan-1-one in which the methyl group at position 2 adopts R-configuration. It is a muscle relaxant and induces ferroptosis in cancer cells.


D-glucose

A glucose with D-configuration.


An aromatic ketone that is (trifluoromethyl)benzene in which the hydrogen at position 4 is replaced by a 2-methyl-3-(pyrrolidin-1-yl)propanoyl group.


A tertiary ammonium ion that is the conjugate acid of lanperisone resulting from the protonation of the pyrrolidine nitrogen. Major microspecies at pH 7.3.


sphingomyelin d18:1

Any sphingomyelin having sphingosine as the sphingoid component.


6-methylsalicylic acid

A monohydroxybenzoic acid that is salicylic acid in which the hydrogen ortho to the carboxylic acid group is substituted by a methyl group.


inclisiran

Inclisiran is a long-acting, synthetic small interfering RNA (siRNA) directed against PCSK9. It is indicated for the treatment of primary hypercholesterolemia (familial and non-familial) or mixed dyslipidemia in adults.


A indol-3-yl carboxylic acid anion that is the conjugate base of 3-(indol-3-yl)pyruvic acid


FLUCICLOVINE

A member of the class of cyclobutanes that is cyclobutane which carries a carboxy, amino and fluoro groups at positions 1, 1 and 3, respectively (the 1r,3r-stereoisomer).


(R)-secondary-alkyl sulfate oxoanion

A secondary alkyl sulfate oxoanion where the substiuents are arranged so the sulfate is in (R)-configuration. Published in DOI:10.1002/adsc.201100864


(S)-secondary-alcohol

A secondary alcohol where the substiuents are arranged so the hydroxy group is in (S)-configuration. Published in DOI:10.1002/adsc.201100864


A quinolone that is 4,6,7,8-tetrahydroquinolin-5(1H)-one substituted by methyl, (2-methoxyethoxy)carbonyl, 2-fluorophenyl and 4-chlorophenyl groups at positions 2, 3, 4 and 7, respectively (the 4S,7S-stereoisomer). It is an inhibitor of voltage-dependent anion channel 3 (VDAC3) and a ferroptosis inducer.


A fluorene that is N-9H-fluoren-9-ylidenehydroxylamine substituted by N-cyclohexylsulfonyl groups at positions 2 and 7. It induces ferroptosis via degradation of GPX4 and also binds and activates squalene synthase.


PENTACHLOROPHENOL

A  chlorophenol that is phenol substituted by 5 chloro groups.


An oxaspiro compound that is 1,2-dioxaspiro[4.5]decane substituted by methyl, 2-hydroxyethyl and tert-butyl groups at positions 3, 3 and 8, respectivey (the 5s,8s-stereoisomer). It induces ferroptosis in cancer cells by indirectly inhibiting glutathione peroxidase 4 (GPX4) enzymatic function and directly oxidizes iron leading to widespread lipid peroxidation.


A disaccharide derivative that is the 6-aminohexyl glycoside of the disaccharide alpha-L-fucopyranosyl-(1->2)-alpha-L-fucopyranose.


A thiazolidinone that is 2-sulfanylidene-1,3-thiazolidin-4-one substituted by 3-{[3-(morpholin-4-yl)propyl]amino}-3-oxopropyl and 4-ethylbenzylidene groups at positions 3 and 5, respectively. It is a ferroptosis inducer.


A linear tetrasaccharide derivative that is the 6-aminohexyl glycoside of the tetrasaccharide alpha-L-fucopyranosyl-(1->2)-alpha-L-fucopyranosyl-(1->2)-alpha-L-fucopyranosyl-(1->2)-alpha-L-fucopyranose.


a lipid IVA(4-)

Tetraanion of a lipid IVA with unspecified (3R)-3-hydroxyacyl chains.


A member of the class of furans that is furan substituted by propyl, carboxy and hydroxymethyl groups at positions 2, 3 and 4, respectively. It is an inducer of antibiotic biosynthesis in Streptomyces species.


a Kdo-lipid IVA(5-)

Kdo-lipid IVA deprotonated at both phosphono groups and at the uronic acid carboxy group and with unspecified (3R)-3-hydroxyacyl chains.


a (Kdo)2-lipid IVA(6-)

(Kdo)2-lipid IVA deprotonated at both phosphono groups and at the uronic acid carboxy group and with unspecified (3R)-3-hydroxyacyl chains.


a (Kdo)2-(acyl)-lipid IVA(6-)

(Kdo)2-(acyl)-lipid IVA deprotonated at both phosphono groups and at the uronic acid carboxy group and with unspecified (3R)-3-hydroxyacyl chains.


A lipid A oxoanion obtained via deprotonation of the carboxy and phosphate OH groups of an alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid A with unspecified (3R)-3-hydroxyacyl chains.


4-acetamidobutanoic acid

An N-acyl-gamma-aminobutyric acid resulting from the monoacetylation of the nitrogen of GABA.


4-methylglutamic acid

A glutamic acid derivative that is glutamic acid substituted by a methyl group at position 4.


An L-alpha-amino acid residue derived from O(3)-{6-O-sulfo-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->3)-N-acetyl-alpha-D-galactosaminyl}-L-threonine residue.


An L-alpha-amino acid residue derived from O(3)-{6-O-sulfo-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->3)-N-acetyl-alpha-D-galactosaminyl}-L-serine residue.


An L-alpha-amino acid residue derived from O(3)-{N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->3)-N-acetyl-alpha-D-galactosaminyl}-L-serine residue.


An L-alpha-amino acid residue derived from O(3)-{N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->3)-N-acetyl-alpha-D-galactosaminyl}-L-threonine residue.