pyrazolotriazine

Any organic heterobicyclic compound where the triazine ring is ortho-fused to a pyrazole ring.


trans-isogeraniol

An isogeraniol that has (E)-configuration.


name: N-(very-long-chain fatty acyl)-sphingoid base

description: A ceramide where the acyl chain chain length is greater than C22 and the sphingoid base is undefined


A ceramide where the acyl chain chain length is greater than C27 and the sphingoid base is undefined


ADP orthovanadate

A vanadium coordination entity that is ADP in which a hydrogen of the terminal phosphate group has been replaced by a (trihydroxido)(oxido)vanadium moiety.


alkapentaene

Acyclic branched or unbranched hydrocarbons having five carbon-carbon double bonds.


An alkapentaene that is henicos-1-ene with 4 cis double bonds at positions 6,9,12 and 15.


An alkapentaene that is tricos-1-ene with 4 cis double bonds at positions 6,9,12 and 15.


name: inositol-1-phospho-N-(2-hydroxy-very-long-chain fatty acyl)-4R-hydroxysphingoid base(1-)

description: An inositol phosphoceramide (1-) in which the acyl chain length is greater than C22 and  hydroxylated at position 2 and the ceramide base is hydroxylated at position 4.


Gln-Lys-Arg

A tripeptide composed of L-glutamine, L-lysine, and L-arginine units joined in sequence by peptide linkages.


A dipeptide resulting from the formal condensation of the carboxy group of L-alpha-aminobutyric acid [(2S)-2-aminobutanoic acid] with the amino group of glycine.


L-beta-ethynylserine zwitterion

An L-alpha-amino acid zwitterion obtained by transfer of a proton from the carboxy group to the amino group of L-beta-ethynylserine. The major species at pH 7.3.


L-Lys-D-Asp

A dipeptide obtained by formal condensation of the carboxy group of L-lysine with the amino group of D-aspartic acid. It is a constituent of bacterial peptidoglycan type A4alpha.


A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 2', 3 and 4. The precursor of 3',4'-dihydroxyaurone.


L-Lys-D-Glu

A dipeptide obtained by formal condensation of the carboxy group of L-lysine with the amino group of D-glutamic acid. It is a constituent of bacterial peptidoglycan type A4alpha.


A phenolate anion resulting from the deprotonation of the phenolic hydroxy group that is ortho to the acyl substituent; major species at pH 7.3.


A hydroxyaurone that is aurone which is substituted by hydroxy groups at the 3' and 4' positions; major species at pH 7.3. It shows inhibitory activity against several isoforms of the histone deacetylase complex (HDAC).


L-Orn-D-Asp

A dipeptide obtained by formal condensation of the carboxy group of L-ornithine with the amino group of D-aspartic acid. It is a constituent of bacterial peptidoglycan type A4beta.


L-Orn-D-Glu

A dipeptide obtained by formal condensation of the carboxy group of L-ornithine with the amino group of D-glutamic acid. It is a constituent of bacterial peptidoglycan type A4beta.


name: anthocyanidin 3-O-beta-D-glucoside 5-O-beta-D-[(6-O-(E)-4-coumaroyl)glucoside] betaine

description: An oxonium betaine obtained by deprotonation of the 7-hydroxy group of anthocyanidin 3-O-beta-D-glucoside 5-O-beta-D-[(6-O-4-hydroxycinnamoyl)glucoside]. It is the major microspecies at pH 7.3


A triglyceride where at least one of R1, R2 or R3 is a linoleoyl group. Formula is C23H36O6R2


An organic anion obtained by selective deprotonation of the 3- and 5-hydroxy groups of  delphinidin; major species at pH 7.3.


An oxonium betaine obtained by deprotonation of the 5 position of delfinidin 3-O-beta-D-glucoside. It is the major microspecies at pH 7.3.


An organic anion obtained by selective deprotonation of the 3- and 5-hydroxy groups of pelargonidin; major species at pH 7.3.


An organic betaine obtained by deprotonation of the hydroxy group at the 5 position of pelargonidin 3-O-beta-D-glucoside. It is the major microspecies at pH 7.3.


An organic anion obtained by selective deprotonation of the 3- and 5-hydroxy groups of peonidin; major species at pH 7.3.


peonidin 3-O-beta-D-glucoside betaine

An oxonium betaine obtained by deprotonation of the 5 position of peonidin 3-O-beta-D-glucoside. It is the major microspecies at pH 7.3.


An organic anion obtained by selective deprotonation of the 3- and 5-hydroxy groups of malvidin; major species at pH 7.3.


malvidin 3-O-beta-D-glucoside betaine

An oxonium betaine obtained by deprotonation of the hydroxy group at the 5 position of malvidin 3-O-beta-D-glucoside. It is the major microspecies at pH 7.3.


PFE-PKIS 18

A member of the class of pyrimidines that is pyrimidine which has been substituted at positions 2, 4, and 5 by (1-isopropyl-2-oxo-2,3-dihydro-1H-indol-5-yl)amino, [3-(methylsulfonyl)benzyl]amino, and trifluoromethyl groups, respectively.


name: omega-hydroxy-ultra-long chain fatty acylceramide

description: A ceramide with no defined sphingoid base and an N-omega-hydroxyacyl chain length greater than C27


A ceramide with no defined sphingoid base and a linoleoyl group esterified to a N-omega-hydroxyacyl chain length greater than C27


profoxydim

A cyclic ketone that is 3-hydroxycyclohex-2-en-1-one substituted by a N-[2-(4-chlorophenoxy)propoxy]butanimidoyl group at position 2 and by a thian-3-yl group at position 5. It is a herbicide used for the control of grass weeds in rice.


A hydroperoxyicosatrienoate resulting from the deprotonation of the carboxy group of (8Z,11Z,13E,15S)-15-hydroperoxyicosa-8,11,13-trienoic acid. The major species at pH 7.3.


m-tyraminium

An ammonium ion that is the conjugate acid of m-tyramine; major species at pH 7.3.


heazlewoodite

A sulfide mineral with formula Ni3S2 which is named after Heazlewood, Tasmania, where it was first described.


N-glycolylneuraminyllactosylceramide

A sialotriaosylceramide in which the triaosyl group is 3,5-dideoxy-5-(2-hydroxyacetamido)-D-glycero-alpha-D-galacto-non-2-ulopyranonosyl-(2->3)-beta-D-galactopyranosyl-(1->4)-beta-D-glucopyranosyl attached to the primary hydroxy function of ceramide. A tumour antigen found in solid tumors such as breast carcinoma, nonsmall cell lung cancer, and melanoma, but not usually detected in normal human cells.


A primary ammonium ion resulting from the protonation of the amino group of 2-amino-2-deoxy-D-galactopyranose. Major species at pH 7.3.


A hydroperoxy polyunsaturated fatty acid anion resulting from the deprotonation of the carboxy group of (15S)-hydroperoxy-(11Z,13E)-icosadienoic acid. Major species at pH 7.3.


L-beta-ethynylserine

A non-proteinogenic L-alpha-amino acid that is L-propargylglycine which is carrying a hydroxy group at the 3R position.


name: Glyceraldehyde 3-phosphate diethyl acetal


A nucleoside 5'-monophosphate(2-) that results from the removal of two protons from the phosphate group of N(6)-methyl-AMP.


A hydroperoxy fatty acid that is (11Z,13E)-icosadienoic acid in which the pro-S hydrogen at position 15 has been replaced by a hydroperoxy group.


A beta-D-glucoside resulting from the formal condensation of beta-D-glucoyranose with the alcoholic hydroxy group of 18-hydroxyocctadec-9-enoic acid.


(2E)-3-methylhex-2-enoic acid

A monounsaturated fatty acid that is (2E)-hexenoic acid in which the hydrogen at position 3 has been replaced by a methyl group. A malodourous component in the sweat of schizophrenics.


isogeraniol

A homoallylic alcohol that is 2,6-dimethylocta-2,5-diene in which a hydrogen of the methyl group at position 8 has been replaced by a hydroxy group.


RETUSIN

A monohydroxyflavone that is 5-hydroxyflavone which is substituted by methoxy groups at positions 3,3',4' and 7.


An N(2)-acyl-L-glutamine that is L-glutamine in which one of the hydrogens of the alpha-amino group has been replaced by a 4-(2,4-dichlorophenoxy)butanoyl group.


A hydroperoxyicosatrienoic acid that is (8Z,11Z,13E)-icosatrienoic acid in which the pro-S hydrogen at position 15 has been replaced by a hydroperoxy group.


A hydroxypyridine that is pyridine substituted by hydroxy groups at positions 2 and 5 and chloro groups at positions 3 and 6. It is a metabolite of the agrochemical chlorpyrifos.


A hydroxypyridine that is pyridine substituted by hydroxy groups at positions 2,3 and 5 and a chloro group at position 6. It is a metabolite of the agrochemical chlorpyrifos.


An organic anion that is the conjugate base of 3,6-dihydroxypyridine-2,5-dione, obtained by selective deprotonation of the hydroxy group at positions 2.


An enolate anion resulting from the deprotonation of the hydroxy group of 6-chloro-3-hydroxypyridine-2,5-dione. The major species at pH 7.3.


A pyridone that is pyridine-2,5-dione which is substituted at positions 3 and 6 by chloro groups. It is a metabolite of the agrochemical, chlorpyrifos.


A homodetic cyclic peptide resulting from the formal condensation of the carboxy group of N(2)-(3-phenylpropanoyl)-L-ornithyl-L-prolyl-3-cyclohexyl-D-alanyl-L-tryptophyl-L-arginine with the 5-amino group of the N(2)-acylornithyl residue.


A monochloropyridine that is 2,5-dioxo-2,5-dihydropyridine which is substituted at positions 3 and 6 by a hydroxy group and a chlorine, respectively.


Major species at pH 7.3.


An ammonium ion derivative that is the conjugate acid of 5-aminopentanal, obtained by protonation of the amino group; major species at pH 7.3.


An iminium ion obtained by protonation of the imino group of 1-piperideine; major microspecies at pH 7.3.


3-amino-2-oxopropyl phosphate

A oxoalkyl phosphate having 3-amino-2-oxopropyl as the oxoalkyl group.


Pro-Arg-Pro

A tripeptide composed of L-proline, L-arginine and L-proline joined in sequence by peptide linkages.


Ser-Trp-Lys

A tripeptide formed from L-serine, L-tryptophan and L-lysine residues joined in sequence by peptide linkages.


Thr-Thr-Thr

A tripeptide composed of three L-threonine units joined by peptide linkages.


An L-cysteine thioether that is L-cysteine in which the hydrogen of the thiol group has been replaced by a 1,2-dicarboxyethyl group. It is a chemical modification which occurs in tissue proteins and formed by a Michael addition of cysteine to fumaric acid.


A pyridone that is pyridine-2,5-dione which is substituted at positions 3 and 6 by hydroxy groups. A metabolite of the agrochemical, chlorpyrifos.


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

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


A member of the class of phenylethanolamines that is phenylethanolamine in which the the phenyl group is substituted at the para- position by a methoxy group, while the am no group is substituted by a 4-(p-nitrophenyl)butan-2-yl group. A beta-adrenergic agonist that has been used illegally in China as an animal feed additive to as a growth promotion to enhance the the lean meat-to-fat ratio for livestock.


N(delta)-methyl-L-argininium

An L-arginine derivative in which the delta-nitrogen atom carries a methyl group; major species at pH 7.3.


An L-arginine derivative in which the omega-nitrogen atom carries a hydroxy group and the delta-nitrogen atom carries a methyl group; major species at pH 7.3.


8-oxocitronellyl enol

An alpha,beta-unsaturated aldehyde that is octa-2,7-dienal which is substituted by a hydroxy group at position 8, methyl groups at positions 2 and 6, and in which both double bonds have E configuration.


A beta-D-glucoside resulting from the formal condensation of the omega-hydroxy group of 16-hydroxyhexadecanoic acid (16-hydroxypalmitic acid) with beta-D-glucose.


An alkylglycerol that is glycerol in which the hydrogen of one of the primary hydroxy groups has been replaced by a dodecyl group.


An organic cation resulting from the deprotonation of the phosphate group and protonation of the alpha-amino and imine nitrogens of the L-arginine moiety of L-arginyl-AMP; Major species at pH 7.3.


dolabellane diterpenoid

A diterpenoid compound having a dolabellane skeleton.


An imidohydrazide resulting from the formal condensation of the hydrazide carbonyl group of N'-(p-chlorophenyl)-3,3-dimethyl-2-oxobutanehydrazide with the amino group of p-chloroaniline. A potent and selective antagonist of sphingosine-1-phosphate receptor 3 (S1PR3).


A secondary carboxamide resulting from the formal condensation of the carboxy group of O-phospho-D-serine with the amino group of m-octylaniline. An analogue of sphingosine-1-phosphate (S1P), it is a potent antagonist for both S1P1 and S1P3 receptors. It can inhibit S1P-induced migration of thyroid cancer cells, ovarian cancer cells, and neural stem cells.


An N(6)-acyl-L-lysine residue derived from N(6)-(2-hydroxyisobutanoyl)-L-lysine.


A nucleotide-sugar oxoanion arising from deprotonation of the diphosphate OH groups of 2''-O-(2-hydroxyisobutanoyl)-ADP-D-ribose; major species at pH 7.3.


The x-ref to MetaCyc (4-Cl-L-Threonyl-PCP) in CHEBI:141018 is wrong


NSC 23766

An aminopyrimidine that is 6-methylpyrimidine-2,4-diamine in which the amino groups at positions 2 and 4 are substituted by 5-(diethylamino)pentan-2-yl and 4-amino-2-methylquinolin-6-yl groups respectively. An inhibitor of the signalling G-protein known as RAC1 (Ras-related C3 botulinum toxin substrate 1).


hydrazonamide

Any organonitrogen compound derived from carboxamides, RC(=O)NR2, by formal condensation with hydrazine (or a substituted hydrazine) to replace the double-bonded oxygen atom by =NNR2 to give RC(=NNR2)NR2.


imidohydrazide

Any organonitrogen compound resulting from the formal condensation of the carbonyl group of a hydrazide, RC(=O)NHNR2, with a primary amino compound (or a substituted hydrazine) to replace the double-bonded oxygen atom by =NR to give RC(=NR)NHNR2.


A monocarboxylic acid anion resulting from the deprotonation of the carboxy group of steviolbioside. The major species at pH 7.3.


A monocarboxylic acid anion resulting from the deprotonation of the carboxy group of steviolmonoside. The major species at pH 7.3.


A monocarboxylic acid anion that is the conjugate base of steviol, obtained by deprotonation of the carboxy group.


rebaudioside A

A rebaudioside that is rubusoside in which the hydroxy groups at positions 3 and 4 of the beta-D-glucopyranosyloxy group at the 13alpha position have both been converted to the corresponding beta-D-glucopyranoside.


rebaudioside B(1-)

A monocarboxylic acid anion resulting from the deprotonation of the carboxy group of rebaudioside B. The major species at pH 7.3.


D-guloside

Any guloside in which the glycoside group is derived from D-gulose.


A nucleotide-sugar oxoanion arising from deprotonation of the diphosphate OH groups of 3''-O-butanoyl-ADP-D-ribose; major species at pH 7.3.


A 3-dehydropyranoside that is any D-gulopyranoside, or any D-galactopyranoside, in which the hydroxy group at position 3 has been oxidised to give the corresponding ketone.


A 3-dehydropyranoside that is any D-glucoside, or any D-allopyranoside, in which the hydroxy group at position 3 has been oxidised to give the corresponding ketone.


rebaudioside E

A rebaudioside that is stevioside in which the hydroxy group at position 2 of the glucosyl ester moiety has been converted into the corresponding beta-D-glucoside.


REBAUDIOSIDE M

A rebaudioside that is rebaudioside A in which the the hydroxy groups at positions 2 and 3 of the beta-D-glucosyl ester moiety have both been converted to the corresponding beta-D-glucoside. Found in very low concentraitions in the leaves of Stevia Rebaudiana, it is more than 200 times sweeter than sucrose.


An N-acetyl-L-amino acid that is L-cysteine in which the hydrogen of the thiol group has been replace by a 1,2-dicarboxyethyl group. The first metabolite in the disposal of S-(2-succino)-L-cysteine by Bacillus subtilis.


RUBUSOSIDE

A steviol glycoside that is steviol in which both the carboxy group and the tertiary allylic hydroxy group have been converted to their corresponding beta-D-glucosides. A precious bioactive natural sweetener which mainly exists the in Chinese sweet tea plant, Rubus suavissimus.


rebaudioside D

A rebaudioside that is rebaudioside A in which the hydroxy group at position 2 of the beta-D-glucosyl ester moiety has been converted to the corresponding beta-D-glucoside. Found in minute quantities in the leaves of Stevia rebaudiana.


rebaudioside

Any of the steviol glycosides found in the leaves of the stevia plant, Stevia rebaudiana. They are typically more than 100 times sweeter than sucrose.


STEVIOL

An ent-kaurane diterpenoid that is 5beta,8alpha,9beta,10alpha-kaur-16-en-18-oic acid in which the hydrogen at position 13 has been replaced by a hydroxy group.


L-psicose

The L-enantiomer of psicose.


steviol glycoside

A diterpene glycoside derived from steviol by formal esterification of the carboxy group with glucose (or a glucose derivative) and glycosylation of the tertiary hydroxy group with combinations of glucose and rhamnose to give the corresponding glycosides.


steviolmonoside

A beta-D-glucoside resulting from the formal condensation the tertiary allylic hydroxy group of steviol with beta-D-glucopyranose.


steviolbioside

A beta-D-glucoside that is steviolmonoside in which the hydroxy group at position 2 of the glucoside moiety has been converted into its beta-D-glucoside.


20-HETE methyl ester

A methyl ester resulting from the formal condensation of the carboxy group of (5Z,8Z,11Z,14Z)-20-hydroxyicosa-5,8,11,14-tetraenoic acid (20-HETE) with methanol.


A hydroperoxy fatty ester resulting from the formal condensation of the carboxy group of  (5Z,9E,11Z,14Z)-8-hydroperoxy-20-hydroxyicosa-5,9,11,14-tetraenoic acid with methanol.


A hydroperoxy fatty ester that is the methyl ester of 12-hydroperoxy-20-hydroxy-(5Z,8Z,10E,14Z)-icosatetraenoic acid.


A hydroperoxy fatty ester resulting from the formal condensation of the carboxy group of (5Z,7E,11Z,14Z)-9-hydroperoxy-20-hydroxyicosa-5,7,11,14-tetraenoic acid with methanol.


A hydroperoxy fatty ester that is the methyl ester of (9R,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoic acid.


hydroperoxy fatty ester

Any fatty acid ester carrying one or more hydroperoxy substituents.


polyunsaturated fatty ester

Any fatty acid ester resulting from the formal esterification of the carboxy group of a polyunsaturated fatty acid.


solasodine 3-beta-D-glucoside(1+)

A secondary ammonium ion resulting from the protonation of the amino group of solasodine 3-beta-D-glucoside. The major species at pH 7.3.


A secondary ammonium ion resulting from the protonation of the amino group of solasodine. The major species at pH 7.3.


pregnenolone 3-beta-D-glucoside

A sterol 3-beta-D-glucoside in which the sterol is 3beta-hydroxypregn-5-en-20-one.


An epoxy steroid that is pregnenolone which has an epoxy group whose oxygen is attached to the 16alpha and 17alpha-positions.


An epoxy steroid that is 3beta-hydroxypregnenolone 3-beta-D-glucoside in which the hydrogens at the 16alpha and 17alpha positions have been replaced by the oxygen of the epoxide ring.


epiandrosterone 3-beta-D-glucoside

A sterol 3-beta-D-glucoside that has epiandrosterone as the sterol component.


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


A sterol 3beta-D-glucoside in which the parent sterol is 16,17-didehydropregnenolone.


1,4-cyclohexanedicarboxylic acid

A dicarboxylic acid that is cyclohexane substituted by carboxy groups at positions 1 and 4.


betaenone A

A carbotricyclic compound that is tricyclo[6.2.2.0(2,7)]dodecan-9-one which is substituted by hydroxy groups at positions 1, 4, and 11; by methyl groups at positions 4, 6, 8, and 11; by a hydroxymethylene group at position 10; and by a (2R)-butan-2-yl group at position 12 (the 1S,2S,4R,6R,7S,8R,10Z,11S,12R stereoisomer). A phytotoxin produced by Pleospora betae, the causal fungus of leaf spot disease on sugar beet.


stemphyloxin II

A carbotricyclic compound that is betaenone A in which the butan-2-yl side-chain has been hydroxylated at position 1. A phytotoxin isolated from the endophytic fungus Stemphylium botryosum, it shows high affinity for ferric (but not ferrous) ions.


stemphyloxin I

An octahydronaphthalene that is 2,4,5,7-tetramethyloctahydronaphthalen-1(2H)-one which is substituted by hydroxy groups at positions 2 and 7, a (2R)-1-hydroxybutan-2-yl group at position 3, and a (2Z)-3-hydroxyprop-2-enoyl group at position 4 (the 2S,3R,4R,4aS,5R,7R,8aS stereoisomer). Isolated from the endophytic fungus Stemphylium botryosum, it is the causal agent of leaf spot and foliage blight disease in tomatoes. Its phytotoxcity is at least 200 times greater than that of stemphyloxin II. It shows high affinity for Fe(3+) (but not Fe(2+)) ions.


dihydrostemphyloxin I

An octahydronaphthalene that is stemphyloxin I in which the C=C bond of the enol moiety has been reduced to a C-C bond.


campesterol 3-beta-D-glucoside

A sterol 3-beta-D-glucoside resulting from the formal condensation of the hydroxy group of campesterol with beta-D-glucopyranose. Found in cloves, common wheat, and peaches.


3-oxo aldehyde

Any aldehyde having an oxo substituent at the 3-position.


(S)-gabaculine

The (S)-enantiomer of gabaculine.


rac-gabaculine

A racemate composed of equimolar amounts of (R)- and (S)-gabaculine. It is an irreversible inhibitor of GABA transaminase.


A dicarboxylic acid anion that is the conjugate base of adipiodone arising from deprotonation of the two carboxy groups; major species at pH 7.3.


viguilenin

An organic heterocricyclic compound and germacranolide with formula C20H30O7 isolated from Viguiera linearis.


ASPERPHENAMATE

A carboxylic ester resulting from the formal condensation of the carboxy group of N-benzoyl-L-phenylalanine with the hydroxy group of N-benzoyl-L-phenylalaninol. A metabolite found in several Pencillium and Aspergillus species, as well as in plants as a product of endophytic fungi.


N-benzoyl-L-phenylalaninate

An N-acyl-L-alpha-amino acid anionresulting from the deprotonation of the carboxy group of N-benzoyl-L-phenylalanine. The major species at pH 7.3.


N-benzoyl-L-phenylalaninol

A member of the class of benzamides resulting from the formal condensation of the carboxy group of benzoic acid with the amino group of L-phenylalaninol.


bassianolide

A cyclodepsipeptide consisting of a cyclic tetramer of the depsipeptide D-Hiv-N-methyl-L-leucine (where D-Hiv = D-alpha-hydroxyisovaleric acid). Found in the fungal species Beauveria bassiana and Verticillium lecanii, it has insecticidal properties and is used as a commercial biopesticide to control of insects of agricultural, veterinary and medical significance. For elucidation of the structure, see Suzuki et al., Tetrahedron Lett. 1977 v25, 2167-2170.


(+)-isoepoxydon

A cyclic ketone that is (-)-phyllostine in which the carbonyl group which is furthest from the hydroxymethyl substituent has been formally reduced to give the corresponding secondary alcohol with S configuration. A metabolite of the patulin pathway in Penicillium urticae.


phyllostine

An epoxide resulting from epoxidation of the 5-6 double bond of 2-(hydroxymethyl)-1,4-benzoquinone (the 5S,6R enantiomer).


isopatulin

A furopyran and lactone that is (2H-pyran-3(6H)-ylidene)acetic acid which is substituted by hydroxy groups at positions 4 an 6 and in which the hydroxy group at position 4 has condensed with the carboxy group to give the corresponding bicyclic lactone. Also known as neopatulin, it is a mycotoxic substance produced by Aspergillus and Penicillium species.


(E)-ascladiol

A butenolide that is furan-2(5H)-one which is substituted by a hydroxymethyl group at position 4 and a 2-hydroxyethylidene group at position 5 (the 5E isomer). A direct precursor of patulin in cell-free preparations of Penicillium urticae patulin-minus mutants J1 and S11, but not S15.


A sterol 3-beta-D-glucoside having 24-methylenecholesterol as the sterol component.


A 1-methyl-4-pyridone-5-carboxamide with 2 deuterium atoms replacing 2 hydrogen atoms.


An ether that is 2-(1H-imidazol-1-yl)-1-(4-methoxyphenyl)ethanol in which the hydrogen of the hydroxy group has been substituted by a 3-(4-methoxyphenyl)propyl group.


SKF-96365 free base(1+)

An organic cation obtained by protonation of the imidazole group of SKF-96365 free base.


(+)-minovincinine

A monoterpenoid indole alkaloid that is (+)-vincadifformine which carries a hydroxy group at position 19S. A natural product found in several plant species including Alstonia venenata and Catharanthus trichophyllus.


A glycosyloxyflavone that is myricetin in which the hydroxy group at position 3 has been converted to the corresponding beta-D-glucosyl-(1->2)-alpha-L-rhamnoside.


guloside

Any hexoside in which the glycoside group is derived from gulose.


L-guloside

Any guloside in which the glycoside group is derived from L-gulose.


A glycosyloxyflavone that is myricetin 3-O-[beta-D-glucosyl-(1->2)-alpha-L-rhamnoside] in which the hydroxy group at position 6 of the glucosyl group has been acylated by a caffeoyl [(1E)-1-(3,4-dihydroxyphenyl)-3-oxoprop-1-en-3-yl] group.


A dipyridodiazepine that is nevirapine in which one of the hydrogens of the methyl group has been substituted by a hydroxy group. It is a metabolite of the anti-HIV drug, nevirapine.


A pyrazolone that is antipyrine in which one of the hydrogens of the 5-methyl group is substituted by a hydroxymethyl group. It is a metabolite of the analgesic drug, antipyrene.


A hydroquinone that is propofol which is substituted by a hydroxy group at position 4. It is a metabolite of the short acting anaesthetic drug, propofol.


5,6-trans-vitamin D3

A member of the class of D3 vitamins that is calciol in which the double bond at position 5 adopts a trans-configuration. During exposure to sunlight, previtamin D3 and vitamin D3 in the skin become photoisomerized to 5,6-trans-vitamin D3.


A member of the class of piperidines that is donepezil in which the 5-methoxy group has been demethylated to the corresponding hydroxy derivative. It is metabolite of donepezil, a drug used in the treatment of dementia.


epoxy steroid

Any steroid whose structure includes an epoxy group.


A thienopyridine that is ticlopidine which carries a hydroxy group at position 7. It is a metabolite of the antiplatelet drug, ticlopidine.


bisnorcholic acid

A bile acid that is 24-dinor-5beta-cholan-22-oic acid bearing three hydroxy substituents at positions 3alpha, 7alpha and 12alpha.


O-desethyl candesartan

A benzimidazolecarboxylic acid that is candesartan in which the ethoxy group has been replaced by a hydroxy group. It is the inactive metabolite of the anti-hypertensive drug, candesartan.


promazine sulfoxide

A member of the class of  phenothiazines that is promazine carrying an oxo group at position 5. It is a metabolite of the anti-psychotic medication, chlorpromazine.


tauroursocholic acid

A bile acid taurine conjugate of  ursocholic acid.


A dipeptide that is N-[(2S)-2-aminobutanoyl]glycine in which the terminal amino group has been acylated by formal condensation of the 5-carboxy group of 2-oxopentanedioic acid.


cellulose acetate

A glucan derivative obtained through the esterification of cellulose by acetic anhydride or acetic acid, resulting in the substitution of some of the hydroxy groups of cellulose by acetyl groups. It is used in a variety of applications including base material for photographic film, clothing, membrane filters, coatings, food packaging, and as a frame material for eyeglasses.


BENZOXAZOLINONE

A member of the class of benzoxazoles that is 2,3-dihydro-1,3-benzoxazole carrying an oxo group at position 2.


A pyrazine that is substituted by an acetyl group at position 2. It has been identified as one of the volatile flavor constituents in popcorn, bread crust, vinegar, and potato snacks.


methyl 3-aminopyrazine-2-carboxylate

A pyrazine that is substituted by a methoxycarbonyl group at position 2 and an amino group at position 3.


A member of the class of  pyrrolidines that is pyrrolidine which is substituted by a methyl group at position 2.


A long-chain fatty acid that is the 17-O-beta-D-glucoside of (9Z)-17-hydroxyoctadec-9-enoic acid.


A hydroxycoumarin that is 4-methylcuomarin which is substituted by hydroxy groups at positions 3 and 4. A hyaluronan synthesis inhibitor. It has also been used as a fluorescent sensor to monitor the consumption of a boronic acid in Suzuki coupling reactions; fluorescence is readily detectable by the naked eye using a standard 365 nm UV lamp.


A glycosyloxyflavone that is myricetin 3-O-[beta-D-glucosyl-(1->2)-alpha-L-rhamnoside] in which the hydroxy group at position 6 of the beta-D-glucosyl group has been converted to the corresponding acetate.  Identified in PMID: 23549747 Fig. S21 peak 4.


A glycosyloxyflavone that is myricetin in which the hydroxy group at position 3 has been converted to the corresponding O-beta-D-glucosyl-(1->2)-beta-D-glucoside. Identified in PMID 29667287 Fig. S17, peak 8.


A methyl propenyl ketone in which the double bond has (E)-configuration. It is a key odorant responsible for the chestnut-like aroma in green tea.


monoacylglycerol 22:4

A monoglyceride in which the acyl groups contain a total of 22 carbons and 4 double bonds


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

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


A hydroperoxyoctadecatrienoic acid that is (9Z,11E,15Z)-octadecatrienoic acid which is substituted at position 13 by a hydroperoxy group.


An O-acyl carbohydrate that is beta-D-glucopyranose in which the anomeric hydroxy hydrogen has been replaced by a 4-hydroxybenzoyl group.


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


monoacylglycerol 22:5

A monoglyceride in which the acyl groups contain a total of 22 carbons and 5 double bonds.


A steroid acid that is 3beta-hydroxy-4alpha-methyl-5alpha-cholesta-8,24-diene in which the hydrogen at the 4beta position has been replaced by a carboxy group.


An N(2)-acyl-L-glutamine resulting from the formal condensation of the alpha-amino group of L-glutamine with the carboxy group of (2E)-3-methylhex-2-enoic acid.


An N-acyl-L-alpha-amino acid resulting from the formal condensation of the carboxy group of 4-(indol-3-yl)butanoic acid with the amino group of L-cysteine.


An N(2)-acyl-L-glutamine that has 3-hydroxy-3-methylhexanoyl as the N(2)-acyl group.


N(6)-lactoyl-L-lysine residue

An N(6)-acyl-L-lysine residue that has lactoyl as the N(6)-acyl group.


(Z)-2,3-didehydroaspartate residue

An anionic amino acid residue that is the (Z)-isomer of the alpha,beta-didehydro derivative of aspartate residue. Major microspecies at pH 7.3.


2,3-dehydroamino acid

A dehydroamino acid whose side-chain contains a double bond at the 2-3 position.


alpha-N-acetylneuraminosyl-(2->3)-[beta-D-galactosyl-(1->3)-N-acetyl-beta-D-galactosaminyl-(1->4)]-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1')-N-acylsphingosine in which the acyl group is acetyl. Ganglioside GM1 with an acetyl group substituting for the long fatty acid typicalof ceramide.


(Z)-2,3-didehydroaspartic acid

A 2,3-dehydroamino acid resulting from the formal dehydrogenation of the side chain of aspartic acid to introduce a C=C double bond at the 2-3 position.


ALPHA-HYDROXY-MIDAZOLAM

An imidazobenzodiazepine that is midazolam in which one of the hydrogens of the methyl group is substituted by a hydroxy group. It is the major metabolite of the anesthetic, midazolam.


An imidazobenzodiazepine that is midazolam which is substituted by a hydroxy group at position 4. It is the minor hydroxylated metabolite of the anesthetic, midazolam.


An imidazobenzodiazepine that is midazolam which is substituted by a hydroxy group at positions 2 and 4. It is the minor metabolite of the anesthetic, midazolam.


An Aspidosperma alkaloid that is hoerhammericine in which the hydroxy group at position 19 has been converted to the corresponding acetate ester. Note the stereoconfiguration of the epoxy group is based on CHEBI:144374, and that of the 19-acetoxy group on the hydroxy group of CHEBI:144372.


1-hydroxymidazolam beta-D-glucuronide

A beta-D-glucosiduronic acid that is beta-D-glucuronic acid in which the anomeric hydroxyl hydrogen has been replaced by a 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-4-yl group. It is the glucuronidated conjugate of the midazolam metabolite, 1-hydroxymidazolam.


4-hydroxymidazolam beta-D-glucuronide

A beta-D-glucosiduronic acid that is beta-D-glucuronic acid in which the anomeric hydroxyl hydrogen has been replaced by a 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-4-yl group. It is the glucuronidated conjugate of the midazolam metabolite, 4-hydroxymidazolam.


CODAMINE

A benzylisoquinoline alkaloid that is 1,2,3,4-tetrahydroisoquinolin-7-ol which is substituted by 3,4-dimethoxybenzyl, methyl, and methoxy groups at positions 1, 2, and 6, respectively (the 1S enantiomer).


A ganglioside derivative that is gangliosde GM1 in which the sialic acid residue contains CH2OH instead of COOH.


A ganglioside derivative that is ganglioside GM1 with a single bond instead of the C4=C5 double bond of sphingosine.


A (14)C-modified compound that is erythromycin A in which one of the methyl groups of the dimethylnitrilo group has a (14)C label. It is used in a breath test to detect liver cytochrome P450 enzyme (CYP3A4) activity in humans.


A steroid acid resulting from the formal oxidation of the formyl group of 4alpha-formyl-ergosta-7,24(28)-dien-3beta-ol to the corresponding carboxylic acid.


4-O-beta-D-glucosyl-trans-sinapic acid

A beta-D-glucoside resulting from the formal condensation of the phenolic hydroxy group of trans-sinapic acid with beta-D-gucopyranose.


A 6-sulfo-D-quinovose (6-deoxy-6-sulfo-D-glucopyranose) that has beta configuration at the anomeric centre.


A primary allylic alcohol that is 2-pentene in which a hydrogen at position 1 has been replaced by a hydroxy group.


A 6-sulfo-D-quinovose that has alpha configuration at the anomeric centre.


Any 3beta-hydroxy steroid which is substituted at the 4alpha and 4beta positions by hydroxymethyl and methyl groups, respectively.


A 2-penten-1-ol in which the double bond has (Z)-configuration. It is a volatile compound found in green tea, virgin olive oil, and broccoli. It is also used as a fragrance ingredient cosmetics, shampoos and soaps as well as in non-cosmetic products such as household cleaners and detergents.


Any 3beta-hydroxy steroid which is substituted at the 4alpha and 4beta positions by formyl and methyl groups, respectively.


crenolanib

A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a 8-(4-aminopiperidin-1-yl)quinolin-2-yl group at position 1 and by a (3-methyloxetan-3-yl)methoxy group at position 5. It is an inhibitor of type III tyrosine kinases, PDGFRalpha/beta and FLT3 (IC50 of 11, 3.2, and 4 nM). Currently under clinical development for the treatment of acute myeloid leukemia.


sulfachloropyrazine

A sulfonamide containing a 5-chloropyrazin-2-yl moiety linked to the amide nitrogen; principally used in veterinary medicine.


binimetinib

A member of the class of benzimidazoles that is 1-methyl-1H-benzimidazole which is substituted at positions 4, 5, and 6 by fluorine, (4-bromo-2-fluorophenyl)nitrilo, and N-(2-hydroxyethoxy)aminocarbonyl groups, respectively. It is a MEK1 and MEK2 inhibitor (IC50= 12 nM). Approved by the FDA for the  treatment of patients with unresectable or metastatic melanoma with a BRAF V600E or V600K mutation in combination with encorafenib.


gilteritinib

A member of the class of pyrazines that is pyrazine-2-carboxamide which is substituted by {3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}nitrilo, (oxan-4-yl)nitrilo and ethyl groups at positions 3,5 and 6, respectively. It is a potent inhibitor of FLT3 and AXL tyrosine kinase receptors (IC50 = 0.29 nM and 0.73 nM, respectively). Approved by the FDA for the treatment of acute myeloid leukemia in patients who have a FLT3 gene mutation.


pexidartinib

A pyrrolopyridine that is 5-chloro-1H-pyrrolo[2,3-b]pyridine which is substituted by a [6-({[6-(trifluoromethyl)pyridin-3-yl]methyl}amino)pyridin-3-yl]methyl group at position 3. It is a potent multi-targeted receptor tyrosine kinase inhibitor of CSF-1R, KIT, and FLT3 (IC50 of 20 nM, 10 nM and 160 nM, respectively). Approved by the FDA for the treatment of adult patients with symptomatic tenosynovial giant cell tumor (TGCT).


enasidenib

A 1,3,5-triazine which is substituted by (2-hydroxy-2-methylpropyl)nitrilo, 6-(trifluoromethyl)pyridin-2-yl and [2-(trifluoromethyl)pyridin-4-yl]nitrilo groups at positions 2,4 and 6, respectively. It is an isocitrate dehydrogenase-2 (IDH2) inhibitor which has been approved for the treatment of adults with relapsed or refractory acute myeloid leukaemia (AML).


An N(6)-acyl-L-lysine that has lactoyl as the N(6)-acyl group.


An N(6)-acyl-L-lysine that has 2-hydroxyisobutanoyl as the N(6)-acyl group.


A 2-acylglycero-3-phospho-1'-glycerol(1-) obtained by deprotonation of the phosphate OH group of any 2-acyl-sn-glycero-3-phosphoglycerol; Major species at pH 7.3.


A carbohydrate acid derivative anion  resulting from the deprotonation of the carboxy group of alpha-Neup5Ac-(2->3)-beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->4)-beta-D-GlcpNAc. The major species at pH 7.3


A carbohydrate acid derivative anion resulting from the deprotonation of the carboxy group of alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->4)-beta-D-GlcNAc-(1->3)-beta-D-Gal-(1->4)-[alpha-L-Fuc-(1->3)]-beta-D-GlcNAc-(1->3)-beta-D-Gal-(1->4)-beta-D-GlcNAc. The major species at pH 7.3.


bentranil

A benzoxazine that is 4H-3,1-benzoxazin-4-one substituted by a phenyl group at position 2. It is a postemergence herbicide used for the control of annual weeds in cereal crops, maize, and rice.


(R)-diclofop

A 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid that is the (R)-enantiomer of diclofop.


(S)-diclofop

A 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid that is the (S)-enantiomer of diclofop.


sulfabromomethazine

A sulfonamide consisting of 5-bromo-4,6-dimethylpyrimidine with a 4-aminobenzenesulfonamido group at the 2-position. A long-acting derivative of sulfamezathine, it is used in the poultry, swine and cattle industries for the treatment of coccidiosis and various bacterial infections.


DICLOFOP

An aromatic ether that is 2-(4-hydroxyphenoxy)propanoic acid in which the hydrogen of the hydroxy group at position 4 has been substituted by a 2,4-dichlorophenyl group.


sulfaethoxypyridazine

A sulfonamide consisting of 6-ethoxypyridazine with a 4-aminobenzenesulfonamido group at the 3-position. Generally licensed for veterinary use only against bacterial infections, such as fowl cholera and salmonella infection.


ketene acetal

An organooxygen compound having the structure RR'C=C(OR'')(OR''') where R'', R''' =/= H. Formally, they are ethers of the enolic form of esters. They bear the same structural relationship to ketenes that acetals bear to aldehydes and ketones.


A sulfonamide consisting of butanoic acid with a 4-aminobenzenesulfonamido group at its 4-position.


A sulfonamide consisting of hexanoic acid with a 4-aminobenzenesulfonamido group at its 6-position.


DICLOFOP-METHYL

A methyl ester resulting from the formal condensation of the carboxylic acid group of 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid with methanol.


(R)-diclofop-methyl

A methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate that is the (R)-enantiomer of diclofop-methyl.


(S)-diclofop-methyl

A methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate that is the (S)-enantiomer of diclofop-methyl.


A sulfonamide consisting of 4-phenylbutanoic acid with a 4-aminobenzenesulfonamido group at the phenyl 4-position.


A member of the class of N-acetylneuraminic acids that is N-acetyl-9-O-acetyl-alpha-neuraminic acid in which the hydroxy group at position 2 (adjacent to the carboxy group) has been methylated to give the corresponding methoxy group.


rigosertib

An N-[2-methoxy-5-({[2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonyl}methyl)phenyl]glycine in which the double bond has E-configuration. It is a non-ATP-competitive inhibitor of PLK1 with an IC50 of 9 nM and exhibits anti-cancer properties.


A sulfonamide consisting of 1,3-thiazol-5-ylacetic acid with a 4-aminobenzenesulfonamido group at the thiazole 2-position.


Dianion of 6-O-phosphono-D-galactono-1,5-lactone arising from deprotonation of the phosphate OH groups; major species at pH 7.3.


Dianion of 2-deoxy-6-O-phosphono-D-glucono-1,5-lactone arising from deprotonation of the phosphate OH groups; major species at pH 7.3.


A monocarboxylic acid anion that is the conjugate base of rigosertib, resulting from the deprotonation of the carboxy group. The major species at pH 7.3.


Dianion of 2-amino-2-deoxy-6-O-phosphono-D-glucono-1,5-lactone arising from deprotonation of the phosphate OH groups; major species at pH 7.3.


Anion of 6-O-sulfono-D-glucono-1,5-lactone arising from deprotonation of the sulfate OH group; major species at pH 7.3.


A glycophytoceramide having a 4-O-benzyl-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


D-glucopyranose 6-sulfate(1-)

An organosulfate oxoanion resulting from deprotonation of the sulfate OH group of D-glucopyranose 6-sulfate; major species at pH 7.3.


glasdegib

A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a (2R,4S)-4-{[(4-cyanophenyl)carbamoyl]amino}-1-methylpiperidin-2-yl group at position 2. It is a hedgehog signalling pathway inhibitor that acts by binding to Smoothened (SMO) receptors and blocking signal transduction (IC50 = 5 nM). It is used in combination with low-dose cytarabine, for the treatment of newly-diagnosed acute myeloid leukemia (AML) in adult patients (aged >= 75 years), or who have medical conditions that prevent the use of standard chemotherapy.


SAPACITABINE

A nucleoside analogue resulting from the formal condensation of the carboxy group of hexadecanoic acid with the amino group of CNDAC. It is the prodrug of CNDAC and is currently in clinical development for the treatment of acute myeloid leukemia (AML).


ivosidenib

A tertiary carboxamide resulting from the formal condensation of the carboxy group of (2S)-1-(4-cyanopyridin-2-yl)-5-oxopyrrolidine-2-carboxylic acid with the secondary amino group of (2S)-2-(2-chlorophenyl)-N-(3,3-difluorocyclobutyl)-2-[(5-fluoropyridin-3-yl)amino]acetamide. It is approved by the FDA for the treatment of acute myeloid leukemia (AML) in patients with an isocitrate dehydrogenase-1 (IDH1) mutation.


indisulam

A chloroindole that is 3-chloro-1H-indole substituted by a [(4-sulfamoylphenyl)sulfonyl]nitrilo group at position 7. It is a carbonic anhydrase inhibitor and a potential anti-cancer agent currently in clinical development.


A glycophytoceramide having a 4-O-(3,4-dichlorobenzyl)-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


A glycophytoceramide having a 4-O-(4-methylbenzyl)-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


A lysophosphatidylethanolamine zwitterion in which the remaining acyl group (position not specified) contains an oleoyl chain.


A pyrimidine 2'-deoxyribonucleoside that is 2'-deoxycytidine having a cyano group in the 2'-position. It is the active metabolite of the anti-cancer drug, sapacitabine which is currently in clinical development for the treatment of hematologic malignancies and solid tumors.


D-glucopyranose 6-sulfate

A monosaccharide sulfate that is D-glucopyranose carrying a single sulfo substituent at position 6.


A glucosamine oligosaccharide comprising N-acetyl-alpha-neuraminosyl, beta-D-galactosyl, 2-acetamido-2-deoxy-3-O-(alpha-L-fucosyl)-beta-D-glucosyl, beta-D-galactosyl, 2-acetamido-2-deoxy-3-O-(alpha-L-fucosyl)-beta-D-glucosyl, beta-D-galactosyl, and 2-acetamido-2-deoxy-D-glucose joined together in sequence by (2->3), (1->4), (1->3), (1->4), (1->3) and (1->4) glycosidic linkages, respectively.


A glycophytoceramide having a 4-O-[4-(trifluoromethyl)benzyl]-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


A glycophytoceramide having a 4-O-(4-tert-butylbenzyl)-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


A glucosamine oligosaccharide comprising N-acetyl-alpha-neuraminosyl, beta-D-galactosyl, 2-acetamido-2-deoxy-beta-D-glucosyl, beta-D-galactosyl, 2-acetamido-2-deoxy-3-O-(alpha-L-fucosyl)-beta-D-glucosyl, beta-D-galactosyl, and 2-acetamido-2-deoxy-D-glucose joined together in sequence by (2->3), (1->4), (1->3), (1->4), (1->3) and (1->4) glycosidic linkages, respectively.


A glycophytoceramide having a 4-O-(cyclopropylmethyl)-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


A glycophytoceramide having a 4-O-allyl-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


A glycophytoceramide having a 4-O-(4-chlorobenzyl)-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


A 2'-deoxyribonucleoside 5'-diphosphate obtained by deprotonation of the three diphosphate OH groups of 2'-deoxy-5-(hydroxymethyl)cytidine 5'-diphosphate ; major species at pH 7.3.


A 2',3'-dideoxyribonucleoside triphosphate oxoanion obtained from 2',3'-dideoxythymidine triphosphate by deprotonation of three of the four free triphosphate OH groups; major species at pH 7.3.


A 2',3'-dideoxyribonucleoside diphosphate oxoanion obtained from 2',3'-dideoxythymidine diphosphate by deprotonation of the diphosphate OH groups; major species at pH 7.3.


A 2',3'-dideoxyribonucleoside monophosphate oxoanion obtained from 2',3'-dideoxythymidine phosphate by deprotonation of the phosphate OH groups; major species at pH 7.3


A sophoroside resulting from the formal condensation of the alcoholic hydroxy group of 17-hydroxyoleic acid with beta-sophorose.


sophoroside

Any glycoside of sophorose (2-O-beta-D-glucopyranosyl-D-glucopyranose).


halauxifen

A  pyridinemonocarboxylic acid that is 4-amino-3-chloropyridine-2-carboxylic acid which is substituted by a 4-chloro-2-fluoro-3-methoxyphenyl group at position 6. It is a herbicide used for the control of broad-leaved weeds in cereals and oilseed rape.


A primary ammonium ion derivative resulting from the protonation of the primary amino group of beta-D-glucosaminyl-(1->4)-N-acetyl-D-glucosamine. The major species at pH 7.3.


A tetrasaccharide derivative consisting of a beta-D-glucosyl residue glycosidically linked to a 5-aminopentyl group and which carries at O-3 a 2,4-di-O-acetyl-6-deoxy-3-O-methyl-alpha-L-talosyl-(1->3)-beta-D-glucosyl-(1->3)-2-O-acetyl-6-deoxy-alpha-L-talosyl trisaccharide unit.


metamifop

A 2-{4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy}-N-(2-fluorophenyl)-N-methylpropanamide that has R-configuration. It is an inhibitor of acetyl-coenzyme A carboxylase (ACCase) and a postemergence herbicide which exhibits high control efficacy against sensitive weeds, especially Echinochloa crus-galli in paddy fields.


rac-metamifop

A racemate comprising equimolar amounts of metamifop and (S)-metamifop.


A member of the class of 1,3-benzoxazoles that is 6-chloro-1,3-benzoxazol-2-ol in which the hydrogen of the hydroxy group at position 2 is substituted by a 4-({1-[(2-fluorophenyl)(methyl)amino]-1-oxopropan-2-yl}oxy)phenyl group.


(S)-metamifop

A 2-{4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy}-N-(2-fluorophenyl)-N-methylpropanamide that has S-configuration.


A tetrasaccharide derivative consisting of a beta-D-glucosyl residue glycosidically linked to a 5-aminopentyl group and which carries at O-3 a 2-O-acetyl-6-deoxy-3-O-methyl-alpha-L-talosyl-(1->3)-beta-D-glucosyl-(1->3)-2-O-acetyl-6-deoxy-alpha-L-talosyl trisaccharide unit.


A glycophytoceramide having a 4-O-(3-phenylpropyl)-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


A glycophytoceramide having a 4-O-(4-phenylbutyl)-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


A glycophytoceramide having a 4-O-(5-phenylpentyl)-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


A glycophytoceramide having a 4-O-(6-phenylhexyl)-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


A glycophytoceramide having a 4-O-[3-(4-methylphenyl)propyl]-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


N-acylethanolamine phosphate(2-)

An organophosphate oxoanion resulting from the removal of both protons from the phosphate group of any N-acylethanolamine.


donepezil (1+)

A piperidinium ion resulting from the protonation of amino group of donepezil.


donepezil

A member of the class of indanones that is 5,6-dimethoxyindan-1-one which is substituted at position 2 by an (N-benzylpiperidin-4-yl)methyl group.


thiencarbazone-methyl

An N-sulfonylurea in which the sulfur atom is attached to a 4-(methoxycarbonyl)-2-methylthiophen-3-yl group and in which the non-sulfonated nitrogen is substituted by a 3-methoxy-4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl group. It is a herbicide used for the selective control of grasses and broadleaf weeds primarily in corn.


thiencarbazone

An N-sulfonylurea in which the sulfur atom is attached to a 4-carboxy-2-methylthiophen-3-yl group and in which the non-sulfonated nitrogen is substituted by a 3-methoxy-4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl group. It is a metabolite of the herbicide, thiencarbazone-methyl.


A piperidinium ion resulting from the protonation of the amino group of (R)-donepezil.


tolpyralate

A racemate comprising equimolar amounts of (R)- and (S)-tolpyralate. It is a proherbicide used for the control of grass and broadleaf weeds in corn.


A glycophytoceramide having a 4-O-[3-(4-chlorophenyl)propyl]-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


(R)-tolpyralate

A 1-({1-ethyl-4-[3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl]-1H-pyrazol-5-yl}oxy)ethyl methyl carbonate that has R-configuration.


(S)-tolpyralate

A 1-({1-ethyl-4-[3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl]-1H-pyrazol-5-yl}oxy)ethyl methyl carbonate that has S-configuration.


A benzoylpyrazole that is 1H-pyrazole substituted by an ethyl, 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl, and 1-[(methoxycarbonyl)oxy]ethoxy groups at positions 1, 4 and 5, respectively.


A glycophytoceramide having a 4-O-[3-(4-methoxyphenyl)propyl]-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


A glycophytoceramide having a 4-O-[3-(3,4-dichlorophenyl)propyl]-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


A benzoylpyrazole that is 1H-pyrazole substituted by an ethyl, 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl, and a hydroxy group at positions 1, 4 and 5, respectively. It is the active metabolite of the proherbicide, tolpyralate.


A glycophytoceramide having a 4-O-[3-(4-fluorophenyl)propyl]-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


An oxopurine that is 1-methyl-7H-xanthine in which the hydrogen attached to the nitrogen at position 3 has been replaced by a propyl group.


A glycophytoceramide having a 4-O-{3-[4-(trifluoromethyl)phenyl]propyl}-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


Fasnall

A racemate comprising equimolar amounts of (R)- and (S)-Fasnall. Both enantiomers act as fatty acid synthase inhibitors, although the (S)-enantiomer was found to be more than 4 times as active as the (R)-enantiomer.


A glycophytoceramide having a 4-O-[3-(4-tert-butylphenyl)propyl]-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


A glycophytoceramide having a 4-O-(4-fluorobenzyl)-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


A glycophytoceramide having a 4-O-(3,4-difluorobenzyl)-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


A glycophytoceramide having a 4-O-(cyclobutylmethyl)-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


A glycophytoceramide having a 4-O-(2-adamantylethyl)-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


A thienopyrimidine that is 5,6-dimethylthieno[2,3-d]pyrimidin-4-amine in which the amino group at position 4 has been substituted by an N-(1-benzylpyrrolidin-3-yl) group.


A glycophytoceramide having a 4-O-propyl-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens.


(R)-Fasnall

An N-(1-benzylpyrrolidin-3-yl)-5,6-dimethylthieno[2,3-d]pyrimidin-4-amine in which the chiral centre has R configuration. Both enantiomers act as fatty acid synthase inhibitors, although the (S)-enantiomer was found to be more than 4 times as active as the (R)-enantiomer.


(S)-Fasnall

An N-(1-benzylpyrrolidin-3-yl)-5,6-dimethylthieno[2,3-d]pyrimidin-4-amine in which the chiral centre has S configuration. Both enantiomers act as fatty acid synthase inhibitors, although the (S)-enantiomer was found to be more than 4 times as active as the (R)-enantiomer.


pevonedistat

A pyrrolopyrimidine that is 7H-pyrrolo[2,3-d]pyrimidine which is substituted by a (1S)-2,3-dihydro-1H-inden-1-ylnitrilo group at position 4 and by a (1S,3S,4S)-3-hydroxy-4-[(sulfamoyloxy)methyl]cyclopentyl group at position 7. It is a potent and selective NEDD8-activating enzyme inhibitor with an IC50 of 4.7 nM, and currently under clinical investigation for the treatment of acute myeloid leukemia (AML) and myelodysplastic syndromes.


motixafortide

A heterodetic cyclic peptide that has antineoplastic activity. It is a CXC chemokine receptor 4 (CXCR4) antagonist with an IC50 value of 0.8 nM and is currently under clinical investigation for the treatment of hematological malignancies, solid tumors, and stem cell mobilization. It was granted orphan drug designation by the FDA for the treatment of pancreatic cancer in 2019.


An organic heterotricyclic compound that is 9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidine which is substituted by a [6-(hydroxyacetyl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl]nitrilo group at position 2 and by a trans-4-methylcyclohexyl group at position 9. It is a FLT3 and CDK4 dual kinase inhibitor that has antineoplastic activity. Currently under clinical investigation in patients with relapsed or refractory acute myeloid leukemia (AML).


N-acylethanolamine phosphate

Any carboxamide resulting from the formal condensation of a carboxylic acid with the amino group of O-phosphoethanolamine (2-aminoethyl dihydrogen phosphate).


Major species at pH 7.3.


name: 7-N-[(5S)-5-amino-5-carboxypentyl]formamidino-7-deazaguanosine 5'-monophosphate zwitterion residue

description: Major species at pH 7.3


viteagnusin D

A labdane diterpenoid resulting from the formal allylic rearrangement of the allylic hydroxy group of peregrinol.


A peptide anion obtained by deprotonation of both carboxy groups and protonation of the glutamyl amino group of S-nitrosoglutathione; major species at pH 7.3.


nitrosothio compound

Any nitroso compound in which a carbon atom of an organyl group is attached to the sulfur atom of a nitrosothio group: R-S-N=O.


S-nitroso-coenzyme A(4-)

Tetraanion of S-nitrosothiol arising from deprotonation of phosphate and diphosphate groups; Major species at pH 7.3.


sulfinamide glutathione(1-)

A sulfinamide glutathione peptide anion; major species at pH 7.3.


sulfinamide-coenzyme A(4-)

A sulfinamide derivative of coenzyme A; major species at pH 7.3.


A labdane diterpenoid resulting from the formal dehydration of the allylic hydroxy group of peregrinol.


peregrinol

A labdane diterpenoid that is labdane which has been hydroxylated at position 5 of the decalin ring and in which the 3-methylpentyl substituent (also at position 5 of the decalin ring) has been dehydrogenated to introduce a trans double bond at the 3-4 position and hydroxylated at position 5.


ethametsulfuron

An N-sulfonylurea that is urea in which one of the nitrogens has been substituted by a 4-ethoxy-6-(methylamino)-1,3,5-triazin-2-yl group, while the other has been substituted by a (2-carboxyphenyl)sulfonyl group.


A labdane diterpenoid that is peregrinol in which one of the hydrogens of the methyl group attached to the double bond has been replaced by a hydroxy group.


ETHAMETSULFURON METHYL

A methyl ester resulting from the formal condensation of the carboxy group of ethametsulfuron with methanol. A herbicide used for the control of broad-leaved weeds in oil seed rape and fodder rape.


macropolylide

Macrolides (macrocyclic lactones) in which the macrocyclic ring contains more than one ester linkage. Macropolylides include macrodiolides, macrotriolides, macrotetrolides and macropentolides, each containing di-, tri-, tetra-, and penta- ester linkages, respectively, in one macrocyclic ring. Macrocyclic lactones containing nitrogen in their skeletons (azamacrolides and macrolide lactams) and also containing oxazole or thiazole in their skeletons are known in nature.


macrodiolide

A macropolylide which contains two ester linkages in one macrocyclic ring.


picloram-methyl

A methyl ester resulting from the formal condensation of the carboxy group of picloram with methanol.


macrotriolide

A macropolylide which contains three ester linkages in one macrocyclic ring.


MANT-GTP

A mixture of 2'-O-(N-methylanthraniloyl)guanosine triphosphate (2'-MANT-GTP; R1 = N-methylanthraniloyl and R2 = H) and 3'-O-(N-methylanthraniloyl)gluanosine triphosphate ((3'-MANT-GTP; R1 = H and R2 = N-methylanthraniloyl). At neutral pH, the isomers are in equilibrium. Used as a fluorescent guanine nucleotide analogue, particularly for kinetic analysis of enzymes and signaling  proteins.


macrotetrolide

A macropolylide which contains four ester linkages in one macrocyclic ring.


An oxabicycloalkane that is 1-methyl-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptan-2-ol in which the hydroxy group is substituted by a (2-methylphenyl)methoxy group.


exo-(+)-cinmethylin

A 1-methyl-2-[(2-methylbenzyl)oxy]-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane that is the exo-(+)-isomer of cinmethylin.


REL-CINMETHYLIN

A 1-methyl-2-[(2-methylbenzyl)oxy]-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane that is the exo-(-)-isomer of cinmethylin.


macrolide lactam

A macrolide in which the macrocyclic lactone ring includes an amide group.


A carbotricyclic compound that is isopimarane with double bonds introduced at the 7-8 and 15-16 positions and in which the hydrogen at position 9 is beta instead of alpha.


dibunate

A naphthalenemonosulfonate obtained by the deprotonation of the sulfonic acid group of dibunic acid.


An imidazolium ion resulting from the protonation of the dihydro imidazole ring of tetryzoline.


A purine ribonucleoside 5'-triphosphate that is GTP substituted at the 2' position by an N-methylanthraniloyl group.


A purine ribonucleoside 5'-triphosphate that is GTP substituted at the 3' position by an N-methylanthraniloyl group.


An alpha-D-GalpNAc-(1->3)-D-GalpNAc in which the anomeric hydroxy group has alpha- configuration.


An amino tetrasaccharide consisting of 2-acetamido-2-deoxy-beta-D-galactopyranosyl, alpha-D-galactopyranosyl, beta-D-galactopyranosyl, and beta-D-glucopyranose units joined together in sequence by (1->3), (1->4), and (1->4) glycosidic linkages, respectively.


A member of the class of neuraminic acids that is neuraminic acid attached in sequence to beta-D-galactopyranosyl, 2-acetamido-2-deoxy-beta-D-glucopyranosyl, beta-D-galactopyranosyl, 2-acetamido-2-deoxy-beta-D-glucopyranosyl, beta-D-galactopyranosyl, and beta-D-glucopyranose units by (2->3), (1->4), (1->3), (1->4), 1->3), and (1->4) glycosidic linkages, respectively.


A member of the class of neuraminic acids that is neuraminic acid attached in sequence to beta-D-galactopyranosyl, 2-acetamido-2-deoxy-beta-D-galactopyranosyl, beta-D-galactopyranosyl, and beta-D-gucoopyranose units by (2->3), (1->3), (1->4), and (1->4) glycosidic linkages, respectively. It corresponds to the carbohydrate portion of ganglioside GM1b.


An alpha-D-Glcp-(1->4)-D-Galp in which the carbon bearing the anomeric hydroxy group has alpha configuration.


A deoxytalose that is alpha-L-talopyranose in which the hydroxy group at position 6 has been replaced by hydrogen.


A tetrasaccharide that is beta-D-glucopyranuroic acid, attached in sequence to beta-D-galactopyranosyl, beta-D-galactopyranosyl, and beta-D-xylopyranose by (1->3), (1->3), and (1->4) glycosidic linkages, respectively.


A glucotriose consisting of three molecules of beta-D-glucopyranose attached in sequence by (1->2) and (1->6) glycosidic linkages.


An amino tetrasaccharide comprising three residues of D-mannose and one of N-acetyl-alpha-D-glucosamine, in a linear sequence, all joined by beta-(1->3)-linkages.


A glucotriose consisting of three molecules of beta-D-glucopyranose attached in sequence by (1->6) and (1->3) glycosidic linkages.


A beta-D-Galf-(1->6)-D-Galf which has beta configuration at the anomeric centre.


An oligosaccharide sulfate that is 2-acetamido-2-deoxy-6-O-sulfo-beta-D-galactopyranose in which the hydroxy group at position 3 has been converted into the corresponding beta-D-glucopyranuronoside.


An amino disaccharide composed of D-galactose and 2-acetamido-2-deoxy-alpha-D-glucopyranosyl residues in (alpha-1->3) linkage.


alpha-D-arabinofuranose

A D-arabinofuranose that has alpha-configuration at the anomeric carbon.


An oligosaccharide sulfate that is 2-acetamido-2-deoxy-4-O-sulfo-beta-D-galactopyranose in which the hydroxy group at position 3 has been converted into the corresponding beta-D-glucopyranuronoside.


An oligosaccharide sulfate that is 2-acetamido-2-deoxy-4-O-sulfo-beta-D-galactopyranose in which the hydroxy group at position 3 has been converted to the corresponding alpha-L-idopyranuronoside.


A beta-D-Galp-(1->3)-D-GlcpNAc in which the N-acetylaminoglucose moiety has alpha configuration.


A galactotriose consisting of two alpha-D-galactopyranose units and a beta-D-galactopyranose joined in sequence by (1->4) glycosidic linkages.


A member of the class of neraminic acids that is beta-D-Galp-(1->3)-2-acetamido-2-deoxy-beta-D-GalpNAc-(1->4)-beta-D-Galp-(1->4)-beta-D-Glcp in which position 3 of the Galp residue is attached to position 2 of the N-glycolylneuraminic acid.


An amino disaccharide comprising a beta-D-mannosyl residue linked (1->3) to an N-acetyl-D-glucosamine residue at the reducing end.


A polysaccharide derivative that is alpha-D-Glcp-(1->3)-alpha-D-Manp-(1->2)-alpha-D-Manp-(1->2)-alpha-D-Manp-(1->3)-beta-D-Manp-(1->4)-beta-D-GlcpNAc-(1->4)-beta-D-GlcpNAc-(1->4) in which the mannopyranosyl group attached by a (1->4)-linkage to the 2-acetamidoglucopyranosyl group is substituted at position 6 by an alpha-D-Manp group, which in turn is substituted at positions 3 and 6 by 2-O-alpha-D-Manp-alpha-D-Manp groups.


A glycosylxylose that is beta-D-xylopyranose in which the hydroxy group at position 2 has been converted to the corresponding 2-O-beta-D-glucopyranoside.


normethylfondaparinux

A heparin pentasaccharide resulting from the hydrolysis of the O-methyl group of fondaparinux.


An alpha-L-arabinofuranoside resulting from the formal condensation of the 6-hydroxy group of beta-D-glucopyranose with the anomeric hydroxy group of alpha-L-arabinofuranose.


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


A glucotriose that is beta-D-glucose in which the hydroxy groups at positions 2 and 4 have each been converted to the corresponding beta-D-glucoside.


A beta-D-Galp-(1->3)-D-Glcp in which the carbon bearing the anomeric hydroxy group has beta configuration.


A beta-D-Galp-(1->3)-D-GalpNAc-(1->3)-D-GalpNAc in which both of the N-acetylgalactose units have alpha configuration at position 1.


methyl beta-D-glucopyranuronate

A methyl D-glucopyranuronate in which the carbon bearing the anomeric hydroxy group has beta configuration.


beta-D-glucofuranose

A D-glucofuranose that has beta- configuration at the anomeric centre.


A polysaccharide consisting of alpha-D-Manp-(1->2)-alpha-D-Manp-(1->2)-alpha-D-Manp-(1->3)-beta-D-Manp-(1->4)-beta-D-GlcpNAc-(1->4)-alpha-D-GlcpNAc in which the hydroxy group at position 6 of the beta-D-Manp group is substituted by an alpha-D-Manp-(1->2)-alpha-D-Manp-(1->3)-[alpha-D-Manp-(1->2)-alpha-D-Manp-(1->6)-]-alpha-D-Manp group.


An alpha-D-Manp-(1->2)-alpha-D-Manp-(1->2)-alpha-D-Manp-(1->3)-D-Manp in which the carbon bearing the anomeric hydroxy group has beta- configuration.


A trisaccharide consisting of beta-D-xylopyranose, alpha-L-arabinopyranose and beta-D-glucopyranose joined together in sequence by (1->2) and (1->6)-glycosidic bonds, respectively.


An amino pentasaccharide that is beta-D-Manp-(1->4)-beta-D-GlcpNAc-(1->4)-beta-D-GlcpNAc in which the mannosyl group has been glycosylated by alpha-D-mannopyranosyl groups at positions 3 and 6.


A high-mannose oligosaccharide that is beta-D-mannopyranose in which the hydrogens of hydroxy groups are replaced by a 3-O-alpha-D-mannopyranosyl-alpha-D-mannopyranosyl group at position 6, a alpha-D-mannopyranosyl-(1->2)-alpha-D-mannopyranosyl-(1->2)-alpha-D-mannopyranosyl group at position 3, and a chitobiose group at position 1.


A branched amino nonasaccharide comprising a linear heptasaccharide chain consisting of N-acetylalpha-neuraminic acid, beta-D-galactose, N-acetyl-beta-D-glucosamine, beta-D-galactose, N-acetyl-beta-D-glucosamine, beta-D-galactose, and beta-D-glucose residues, linked sequentially (2->3), (1->4), (1->3), (1->4), (1->3), and (1->4), with alpha-L-fucosyl residues linked (1->3) to each of the N-acetyl-D-glucosamine residues.


An amino tetrasaccharide comprising a linear chain of three alpha-D-mannose and one N-acetyl-alpha-D-glucosamine resides joined in sequence by (1->2), (1->6) and (1->2) glycosidic linkages.


An amino disaccharide consisting of beta-D-glucopyranuronic acid residue joined by a (1->4) glycosidic linkage to a 2-deoxy-2-(sulfoamino)-alpha-D-glucopyranosyl residue.


A high mannose oligosaccharide consisting of three alpha-D-mannopyranose residues, a beta-D-mannopyranose residue, a 2-acetamido-beta-D-glucopyranosyl residue and a 2-acetamido-alpha-D-glucopyranosyl residues joined in sequence by (1->2), (1->2), (1->3), (1->4), and (1->4) glycosidic linkages, and in which the second mannosyl group from the chitobiose moiety is substituted at position 6 by a alpha-D-mannopyranosyl-(1->6)-[alpha-D-mannopyranosyl-(1->2)-alpha-D-mannopyranosyl-(1->3)]-alpha-D-mannopyranosyl group.


A beta-D-Glcp-(1->3)-[beta-D-Glcp-(1->6)]-D-Glcp which has beta- configuration at the anomeric carbon of the non-terminal glucopyranose ring.


An amino tetrasaccharide consisting of alpha-D-mannose, beta-D-mannose, N-acetyl-beta-D-glucosamine and N-acetyl-alpha-D-glucosamine joined together in sequence by (1->3), (1->4) and (1->4) glycosidic linkages.


A alpha-D-Gal-(1->4)-D-Gal in which both galactose residues have alpha- configuration at the anomeric centre.


A member of the class of neuraminic acids that is neuraminic acid attached in sequence to beta-D-galactopyranosyl, 2-acetamido-2-deoxy-beta-D-glucopyranosyl, beta-D-galactopyranosyl, and beta-D-glucopyranosyl, residues by (2->3), (1->3), (1->3) and (1->4) glycosidic linkages. The galactosyl residue attached to the neuraminic acid is glycosylated at position 4 by a beta-D-acetamidogalactosyl residue, while the other galactosiyl residue has been glycosylated at position 4 by a beta-D-galactopyranosyl-(1->3)-2-acetamido-beta-D-galactopyranosyl residue.


A high-mannose oligosaccharide that is alpha-D-Manp-(1->6)-[alpha-D-Manp-(1->2)-alpha-D-Manp-(1->2)-alpha-D-Manp-(1->3)]-beta-D-Manp-(1->4)-beta-D-GlcpNAc-(1->4)-2-D-GlcpNAc inomeric hydroxy group of the terminal N-acetamidoglucose residue has alpha configuration.


A disaccharide that is alpha-D-arabinopyranose in which the hydroxy group at position 2 has been converted into the corresponding beta-D-glucoside.


A glucotriose consisting of three molecules of beta-D-glucopyranose joined in a linear sequence by (1->4) and (1->6) glycosidic linkages.


A beta-D-GlcpNAc-(1->4)-beta-D-GlcpA-(1->3)-D-GlcpNAc in which the carbon bearing the anomeric hydroxy group has beta configuration.


A member of the class of neuraminic acids that is neuraminic acid attached in sequence to beta-D-galactopyranosyl, 2-acetamido-2-deoxy-beta-D-glucopyranosyl, beta-D-galactopyranosyl, and beta-D-glucopyranosyl, residues by (2->3), (1->3), (1->3) and (1->4) glycosidic linkages. The galactosyl residue attached to the neuraminic acid is glycosylated at position 4 by a beta-D-acetamidogalactosyl residue, while the other galactosyl residue has been glycosylated at position 4 by a 2-acetamido-beta-D-galactopyranosyl residue.


An amino trisaccharide consisting of beta-D-mannose, beta-D-2-acetamido-2-deoxyglucose and alpha-D-2-acetamido-2-deoxyglucose residues joined by sequential (1->4)-linkages.


An amino disaccharide that is an N-acetyl-alpha-D-glucosamine in which the hydroxy group at position 3 has been converted into the corresponding beta-D-glucopyranoside.


A deoxyallose that is beta-D-allopyranose in which the hydroxy group at position 6 has been replaced by a hydrogen.


sambubiose

A disaccharide consisting of beta-D-xylose and beta-D-glucose linked via a 1->2 glycosidic bond.


CID 91859537

A polysaccharide consisting of alpha-D-Glcp-(1->2)-alpha-D-Glcp-(1->3)-alpha-D-Glcp-(1->3)-alpha-D-Manp-(1->2)-beta-D-Manp-(1->2)-alpha-D-Manp-(1->3)-beta-D-Manp-(1->4)-beta-D-GlcpNAc-(1->4)-alpha-D-GlcpNAc in which the beta-D-Manp- residue attached to the beta-D-Glcp residue is glycosylated at position 6 by an alpha-D-mannopyranosyl group, which in turn is substituted at positions 3 and 6 by 2-O-alpha-D-mannopyranosyl-alpha-D-mannopyranosyl groups.


A high-mannose oligosaccharide and an amino nonasaccharide that is alpha-D-Manp-(1->3)-alpha-D-Manp-(1->6)-[alpha-D-Manp-(1->2)-alpha-D-Manp-(1->2)-alpha-D-Manp-(1->3)]-beta-D-Manp-(1->4)-beta-D-GlcpNAc-(1->4)-alpha-D-GlcpNAc in which position 2 of the alpha-D-mannopyranosyl group at the end of the shortest branch from the chitobiose moiety has been converted to the corresponding alpha-D-mannopyranoside.


A glycosylxylose that is beta-D-xylopyranose in which the hydroxy group at position 3 has been converted into the corresponding beta-D-glucopyranoside.


A glucotriose consisting of three molecules of beta-D-glucopyranose joined in a linear sequence by 1->2 glycosidic linkages.


A disaccharide that is beta-D-glucopyranose in which the hydroxy group at position 6 has been converted into the corresponding alpha-L-arabinopyranoside.


A tetrasaccharide derivative consisting of alpha-L-fucose, beta-D-galactose and two N-acetyl-alpha-D-galactosamine residues joined in sequence by (1->2), (1->3) and (1->3) glycosidic bonds.


An amino octasaccharide consisting of four beta-D-galactopyranosyl-(1->4)-beta-D-N-acetylglucosamine disaccharides linked together by (1->3) glycosidic linkage, but with beta-D-glucopyranose replacing beta-D-N-acetylglucosamine as the terminal monosaccharide.


A glycosylxylose that is beta-D-xylopyranose in which the hydroxy group at position 4 has been converted into the corresponding beta-D-galactopyranoside.


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


A deosygulose that is beta-D-gulopyranose in which the hydroxy group at position 6 has been replaced by a hydrogen.


A trisaccharide that is beta-D-galactopyranose in which the hydroxy groups at positions 2 and 3 have each been converted into the corresponding beta-D-glucopyranoside.


An amino trisaccharide consisting of N-acetyl-beta-D-galactopyranosamine, beta-D-galactopyranose and beta-D-glucopyranose residues joined in sequence by (1->4) glycosidic bonds.


An amino tetrasaccharide consisting of a 6-O-[(2-aminoethoxy)(hydroxy)phosphoryl-alpha-D-mannopyranosyl residue, two alpha-D-mannopyranosyl residues, and a 2-amino-alpha-D-glucose residue linked together in sequence by (1->2), (1->6) and (1->4) glycosidic bonds.


A beta-D-Xylp-(1->2)-D-GlcpA in which the carbon bearing the anomeric hydroxy group has beta configuration.


A glucotriose consisting of three molecules of beta-D-glucopyranose joined in a linear sequence by 1->6 glycosidic linkages.


deoxytalose

A deoxyhexose resulting from the replacement of at least one hydroxy group of a talose by a hydrogen.


A member of the class of indoles that is 1H-indole substituted by a [(8aS)-1-oxo-1,2,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazin-3-yl]methyl group at position 3.


carpronium

A methyl ester resulting from the formal condensation of the carboxy group of  4-(trimethylammonio)butanoic acid with methanol.


A member of the class of indoles that is 1H-indole substituted by a 3-methylbut-1-en-3-yl group at position 2 and a [(8aS)-1-oxo-1,2,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazin-3-yl]methyl group at position 3.


galactoxylomannan

An exopolysaccharide composed of an alpha-(1->6)-galactan backbone containing four potential short oligosaccharide branch structures, produced by the human pathogenic fungus Cryptococcus neoformans, that produces immune paralysis in some animals, including humans.


A member of the class of indoles that is 1H-indole substituted by a 3-methylbut-1-en-3-yl group at position 2 and a (1-hydroxy-7,8-dihydro-6H-pyrrolo[1,2-a]pyrazin-5-ium-3-yl)methyl group at position 3.


A hydroxy monocarboxylic acid anion resulting from the deprotonation of the carboxy group of (R)-2-hydroxy-3-methylbutyric acid. The major species at pH 7.3.


bolandiol

A 3beta-hydroxy steroid that is estr-4-ene substituted by a beta-hydroxy group at positions 3 and 17. It is a synthetic anabolic steroid that is used as a dietary supplement by athletes to enhance performance.


PIBUTIDINE

An aromtic ether that is 4-(piperidin-1-ylmethyl)pyridin-2-ol in which the hydroxy group has been substituted by a {(2Z)-4-[(2-amino-3,4-dioxocyclobut-1-en-1-yl)amino]but-2-en-1-yl}oxy group. It is a H2 receptor antagonist which was developed for the treatment of peptic ulcers and duodenal ulcers.


A 2-(D-glucosyloxy)benzoic acid with beta configuration at the anomeric centre.


D-glucofuranose

The furanose form of D-glucose.


A piperidinium ion resulting from the protonation of the piperidine nitrogen of pibutidine; major species at pH 7.3.


fluopimomide

A benzamide resulting from the formal condensation of the carboxy group of 2,3,5,6-tetrafluoro-4-methoxybenzoic acid with the amino group of 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]methanamine. It is a benzamide fungicide, synthesized by Shandong Sino-Agri United Biotechnology Co., Ltd (China). Used for the control of cucumber and grape downy mildew, phytophthora capsici, litchi downy blight, potato late blight, rice sheath blight, and cotton rhizoctonia solani.


A member of the class of napthalenes that is naphthalene which is substituted by an isopropyl group at positions 2 and 6. It is a plant growth regulator which inhibits the sprouting of potatoes during storage.


A benzoate resulting from the removal of a proton from the carboxylic acid group of 2-(beta-D-glucopyranosyloxy)benzoic acid.


N,N-dimethyl-L-prolinium residue

The N,N-dimethylated derivative of L-proliniumyl group


tandospirone

A dicarboximide that is (3aR,4S,7R,7aS)-hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione which is substituted by a 4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl group at position 2. It is a potent and selective 5-HT1A receptor partial agonist (Ki = 27 nM).


An ammonium ion resulting from the addition of a proton to the piperazine nitrogen which is attached to the alkyl chain. The major species at pH 7.3.


A member of the class of indoles that is 1H-indole substituted by a 3-methylbut-1-en-3-yl group at position 2 and a (1-hydroxy-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrazin-2-ium-3-yl)methyl group at position 3.


Major species at pH 7.3.


beta-D-glucosyl salicylate

A D-glucosyl salicylate in which the glucosyl moiety has beta-configuration at the anomeric centre. A transferrin binding compound used in research for cancer therapy.


notoamide S

A notoamide that is 2-(2-methylbut-3-en-2-yl)-7-(3-methylbut-2-en-1-yl)-1H-indol-6-ol which has been substituted at position 3 by a [(3S,8aS)-1,4-dioxooctahydropyrrolo[1,2-a]pyrazin-3-yl]methyl group.  Isolated from a mussel-derived Aspergillus species. The precursor of notoamide E.


notoamide E

A pyranoindole that is notoamide S in which the phenolic hydrosy group at position 6 of the indole moiety has formal addition to the 3-methylbut-2-en-1-yl group at postion 7 of the indole moiety to give the corresponding 7,7-dimethyl-1,7-dihydropyrano[2,3-g]indole derivative. Isolated from a mussel-derived Aspergillus species.


NOTOAMIDE C

A notoamide that is 7,7-dimethyl-1,7-dihydropyrano[2,3-g]indol-2(3H)-one which is substituted at position 3 by 3-methylbut-1-en-3-yl and [(3S,8aS)-1,4-dioxooctahydropyrrolo[1,2-a]pyrazin-3-yl]methyl groups (the all-S stereoisomer). Isolated from a mussel-derived Aspergillus species.


notoamide D

An organic heterohexacyclic compound isolated from a mussel-derived Aspergillus species that is 3,6b,7,7a,10,11,12,12a,14a,15-decahydro-8H,13H-pyrano[2,3-g]pyrrolo[1'',2'':4',5']pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-8,13-dione which is substituted by two methyl groups at position 3, a hydroxy group at the 6b position, and a 2-methylbut-3-en-2-yl group at the 14a position (the 6bR, 7aS, 12aS, 14aS stereoisomer).


(R)-propyromazine

A 1-methyl-1-[1-oxo-1-(10H-phenothiazin-10-yl)propan-2-yl]pyrrolidinium that has R-configuration.


(S)-propyromazine

A 1-methyl-1-[1-oxo-1-(10H-phenothiazin-10-yl)propan-2-yl]pyrrolidinium that has S-configuration.


notoamide

Any member of the class of indole alkaloids isolated from a marine-derived Aspergillus fungus and derived from proline, tryptophan and one or two isoprene units. They are closely related to  brevianamides,  paraherquamides,  marcfortines,  asperparalines and stephacidins.


A methyl glycoside that is beta-D-Gal-(1->4)-[beta-D-Gal-(1->4)-beta-D-Glc-(1->6)]-beta-D-GlcNAc in which the hydroxy group at the reducing-end anomeric centre is methylated.


A methyl glycoside that is beta-D-Gal-(1->4)-[beta-D-Gal-(1->4)-beta-D-Glc-(1->6)]-beta-D-GlcNAc in which the CH2OH of the galactose within the trisaccharide chain is replaced by anionic carboxylate and the hydroxy group at the reducing-end anomeric centre is methylated.


An anthocyanin cation consisting of delphinidin having a rutinosyl [6-deoxy-alpha-L-mannosyl-(1->6)-beta-D-glucosyl] residue attached at the 3-hydroxy position and a beta-D-glucosyl residue at the 7-hydroxy position.


A conjugate base of delphinidin 3-O-rutinoside-7-O-beta-D-glucoside arising from selective deprotonation of the 5-hydroxy group; major species at pH 7.3.


A glycoside that is beta-D-Gal-(1->4)-[beta-D-Gal-(1->4)-beta-D-Glc-(1->6)]-beta-D-GlcNAc in which the hydroxy group at the reducing-end anomeric centre is replaced by a 3-azaniumylpropyl group.


amezinium metilsulfate

A pyridazinium ion that is pyridazin-1-ium which is substituted by a phenyl, amino and methoxy groups at positions 1, 4 and 6, respectively.


pyridazinium ion

An organic cation resulting from the protonation of one of the nitrogens of pyridazine or its derivatives.


TRAMIPROSATE

An amino sulfonic acid that is the 3-amino derivative of propanesulfonic acid.


A glycoside that is beta-D-Gal-(1->4)-[beta-D-GalA(-)-(1->4)-beta-D-Glc-(1->6)]-beta-D-GlcNAc in which the hydroxy group at the reducing-end anomeric centre is replaced by a 3-azaniumylpropyl group.


A methyl glycoside that is beta-D-Gal-(1->4)-[beta-D-Gal-(1->4)-beta-D-Glc-(1->6)]-beta-D-GlcNAc in which the hydroxy group at position 6 of the galactose residue linked to O-4 of the reducing end glucosyl residue is replaced by an ammoniumyl group and the hydroxy group at the reducing-end anomeric centre is methylated.


A methyl glycoside that is beta-D-Gal-(1->4)-[beta-D-Gal-(1->4)-beta-D-Glc-(1->6)]-beta-D-GlcNAc in which the CH2OH of the galactose within the trisaccharide chain is replaced by anionic carboxylate, the hydroxy group at position 6 of the galactose residue linked to O-4 of the reducing end glucosaminyl residue is replaced by an ammoniumyl group and the hydroxy group at the reducing-end anomeric centre is methylated.


prednisolone sodium phosphate

A synthetic glucocorticoid resulting from the formal condensation of the 21-hydroxy group of prednisolone with one of the hydroxy groups of phosphoric acid. It is a prodrug for prednisolone that is activated in vivo by phosphatases.


prednisolone phosphate(2-)

A steroid phosphate oxoanion which is the dianion obtained by the deprotonation of the phosphate OH groups of prednisolone phosphate.


glycosylarabinose

A disaccharide having arabinose at the reducing end with a glycosyl residue attached at an unspecified position via a glycosidic bond.


Any glycoside derived from dimeric Lewis X {beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-beta-D-GlcpNAc}.


A methyl glycoside that is alpha-L-Fucp-(1->3)-[beta-D-Galp-(1->4)]-beta-D-Glcp (LacLe(x)) in which the hydroxy group at the reducing-end anomeric centre is methylated.


A methyl glycoside that is alpha-L-Fucp-(1->3)-[beta-D-Glcp-(1->4)]-beta-D-GlcpNAc (Le(x)) in which the hydroxy group at the reducing-end anomeric centre is methylated.


silanamine

An N-silyl compound that is silane in which a hydrogen is substituted by an amino group.


A monounsaturated fatty aldehyde that is heptadecanal carrying a double bond at position 16.


N-(trifluoroacetyl)glycine

An N-acylglycine resulting from the formal condensation of the amino group of glycine with the carboxy group of trifluoroacetic acid.


tiquizium

A member of the class of quinolizines that is trans-5-methyloctahydro-2H-quinolizinium which is substituted by a di(thiophen-2-yl)methylidene group at position 3. Its bromide salt is used as an antispasmodic drug.


A primary alcohol that is hex-3-ene substituted by a hydroxy group at position 1.


A monohydroxyacetophenone that is acetophenone in which one of the hydrogens ortho to the acetyl group has been replaced by a hydroxy group.


A carboxylic ester resulting from the formal condensation of the carboxy group of isobutyric acid with the 1-hydroxy group of 2,4,4-trimethylpentane-1,3-diol.


A methyl glycoside that is beta-D-Galp-(1->4)-[alpha-L-Rhap-(1->3)]-beta-D-GlcpNAc (LacLe(x)) in which the hydroxy group at the reducing-end anomeric centre is methylated.


A methyl glycoside that is beta-D-Galp-(1->4)-[alpha-L-Rhap-(1->3)]-beta-D-Glcp (RhaLac) in which the hydroxy group at the reducing-end anomeric centre is methylated.


A steroid acid that is 4beta,14-dimethyl-5alpha,9beta-9,19-cyclocholest-24-en-3beta-ol in which the 4alpha hydrogen has been replaced by a carboxy group.


A cyclic adenyl ribonucleotide that is cAMP (cyclic adenosine 3',5'-phosphate) in which the hydrogen at position 8 has been replaced by a piperidin-1-yl group. A selective cAMP-dependent protein kinase A (PKA) activator and cAMP analogue with high selectivity for site A of PKA type I and for site B of PKA type II.


An ammonium ion derivative that is the conjugate acid of (S)-methcathinone obtained from the protonation of the amino group. It is the major species at pH 7.3.


A monocarboxylic acid anion resulting from the deprotonation of the carboxy group of (Z)-3-amino-2-methylacrylic acid. The major species at pH 7.3.


A methylhypoxanthine that is hypoxanthine with the methyl group at position 9.


A methylhypoxanthine that is hypoxanthine with the methyl group at position 7.


gamma-octalactone

A gamma-lactone that is oxolan-2-one substituted by a butyl group at position 5. It is a volatile compound found in peaches, mangoes, beef and ham.


A methylhypoxanthine that is hypoxanthine with the methyl group at position 3.


gamma-decalactone

A gamma-lactone that is oxolan-2-one substituted by a hexyl group at position 5.


(Z)-3-amino-2-methylacrylic acid

An alpha,beta-unsaturated monocarboxylic acid that is methacrylic acid (2-methylacrylic acid) in which the pro-Z hydrogen at the beta position has been replaced by an amino group.


A disaccharide derivative that is alpha-mannobiose in which the hydroxy group at position 3 of each mannose residue has been substituted by a methyl group.


phosphatidylethanolamine 42:5

A phosphatidylethanolamine in which the acyl groups at C-1 and C-2 contain 42 carbons in total with 5 double bonds.


Asn-Arg

A dipeptide obtained by formal condensation of the carboxy group of L-asparagine with the amino group of L-arginine.


L-lyxonate

A lyxonate that is the conjugate base of L-lyxonic acid, obtained by the deprotonation of the carboxy group.


A sialopentaosylceramide consisting of a branched hexasaccharide made up from one sialyl residue, two galactose residues, one L-fucose residue, one N-acetyl-6-sulfoglucosamine residue and one glucose residue, which at the reducing end is attached to a d18:1/18:0 ceramide moiety via a beta-linkage; commonly known as sialyl 6-sulfo Lewis X.


lyxonic acid

A pentonic acid resulting from the formal oxidation of the aldehyde group of lyxose to the corresponding carboxylic acid.


lyxonate

A pentonate resulting from the deprotonation of the carboxy group of a lyxonic acid.


D-lyxonate

A lyxonate that is the conjugate base of D-lyxonic acid, obtained by the deprotonation of the carboxy group.


A bile acid that is 5alpha-cholan-24-oic acid carrying an oxo group at position 3 and a hydroxy group at position 7beta.


A 3-hydroxy steroid that is estriol carrying an oxo group at position 6.


16-sinapoyloxypalmitic acid

A carboxylic ester resulting from the formal condensation of the carboxy group of trans-sinapic acid with the hydroxy group of 16-hydroxyhexadecanoic acid.


A monocarboxylic acid anion that is the conjugate base of 16-sinapoyloxypalmitic acid resulting from the deprotonation of the carboxy group.


quercetin 3-O-gentiotetroside

A quercetin O-glucoside that is quercetin attached to a beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside residue at position 3 via a glycosidic linkage.


A sialopentaosylceramide consisting of a branched hexasaccharide made up from one lactamized sialyl residue, two galactose residues, one L-fucose residue, one N-acetyl-6-sulfoglucosamine residue and one glucose residue, which at the reducing end is attached to a d18:1/18:0 ceramide moiety via a beta-linkage; commonly known as lactamized sialyl 6-sulfo Lewis X ganglioside.


A glycosyloxyflavone that is apigenin substituted by a 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside group at position 7.


L-canaline zwitterion

An amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of L-canaline; major species at pH 7.3.


A sialotetraosylceramide consisting of a linear pentasaccharide made up from one lactamized sialyl residue, two galactose residues, one N-acetyl-6-sulfoglucosamine residue and one glucose residue, which at the reducing end is attached to a d18:1/18:0 ceramide moiety via a beta-linkage.


A neoglycolipid consisting of a linear pentasaccharide made up from one lactamized sialyl residue, two galactose residues, one N-acetyl-6-sulfonatoglucosamine residue (with associated sodium cation) and one glucose residue, which at the reducing end is attached glycosidically to a 2-(tetradecyl)hexadecyl group.


curcumin 4'-O-beta-D-gentiotrioside

A glycoside that is curcumin substituted by a beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside group at position 4'.


curcumin 4'-O-beta-D-gentiotetraside

A glycoside that is curcumin substituted by a beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside group at position 4'.


A neoglycolipid consisting of a branched hexasaccharide made up from one lactamized sialyl residue, two galactose residues, onr fucose residue, one N-acetyl-6-sulfonatoglucosamine residue (with associated sodium cation) and one glucose residue, which at the reducing end is attached glycosidically to a 2-(tetradecyl)hexadecyl group.


genistin 7-O-gentiobioside

A glycosyloxyisoflavone that is genistein substituted by a 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside group at position 7.


A member of the class of chitobioses consisting of N-acetyl-D-glucosamine having a beta-D-glucosaminyl residue attached at the 4-position.


sesaminol

A furofuran that is cis-tetrahydro-1H,3H-furo[3,4-c]furan substituted by a 6-hydroxy-1,3-benzodioxol-5-yl group at position 1S and a 1,3-benzodioxol-5-yl group at position 4S. It is metabolite found in sesame seeds.


The conjugate base of 2-azelaoyl-sn-glycero-3-phosphocholine, obtained by deprotonation of the free carboxy group; major species at pH 7.3.


The conjugate base of 2-glutaroyl-sn-glycero-3-phosphocholine, obtained by deprotonation of the free carboxy group; major species at pH 7.3.


A 2-acyl-sn-glycero-3-phosphocholine in which the acyl group is specified as 5-oxovaleroyl.


A 2-acyl-sn-glycero-3-phosphocholine in which the acyl group is specified as 9-oxononanoyl.


SESAMINOL MONOGLUCOSIDE

A beta-D-glucoside that is sesaminol in which the hydroxy group at position 5 is substituted by a beta-D-glucopyranoside group. A metabolite found in sesame seeds.


sesaminol 2-O-beta-D-gentiobioside

A disaccharide derivative that is sesaminol in which the hydroxy group at position 5 has been substituted by a 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside group. It is a metabolite found in sesame seeds.


A monomethoxyflavone that is myricetin in which the hydroxy group at position 7 is substituted by a methoxy group.


A carboxylic ester resulting from the formal condensation of caffeic acid with the hydroxy group at position 6 of the terminal glucose residue of quercetin 3-O-beta-D-glucosyl-(1->2)-beta-D-glucoside.


A glycosyloxyflavone that is myricetin 3-O-[beta-D-glucosyl-(1->2)-alpha-L-rhamnoside] in which the terminal glucose residue has been esterified at position 6 by formal condensation with 4-coumaric acid. Identified in Fig. S21 of PMID:29967287.


dihydroouabagenin

A hexahydroxy steroidal lactone that is the 20,22-dihydro derivative of ouabagenin.


A monocarboxylic acid anion that is the conjugate base of mupirocin obtained by the deprotonation of the carboxy group; major microspecies at pH 7.3.


A member of the class of hydroxyindoles that is melatonin in which the hydrogen at position 2 of the indole ring has been replaced by a hydroxy group. A predominant hydroxylated melatonin metabolite in plants.


name: ring-opened abasic DNA residue cross-linked to a protein cysteinyl group

description: An abasic DNA-protein cross-linked residue resulting from the formal condensation of L-cysteine residue of a protein with a ring-opened abasic site [also known as AP (apurinic or apyrimidinic) site] of DNA forming a thiazolidine covalent linkage.


N-oleoylethanolamine phosphate

A N-acylethanolamine phosphate in which the acyl group is specifed as (9Z)-octadec-9-enoyl. It is a lysophosphatidic acid-1 (LPA1) receptor agonist.


An organic anion that is the conjugate base of digoxin resulting from the deprotonation of furanone moiety; major species at pH 7.3.


An organic anion that is the conjugate base of digitoxin resulting from the deprotonation of furanone moiety; major species at pH 7.3.


An organic anion that is the conjugate base of digoxigenin resulting from the deprotonation of the furanone moiety; major species at pH 7.3.


An organic anion that is the conjugate base of ouabain resulting from the deprotonation of the furanone moiety; major species at pH 7.3.


An organic anion that is the conjugate base of ouabagenin resulting from the deprotonation of the furanone moiety; major species at pH 7.3.


A 2-benzofuran consisting of phthalide having a butylidene group at the 3-position.


A quinolone that is 4-quinolone substituted at positions 1, 3, 5, 6 and 7 by ethyl, carboxy, amino, fluorine, and cyclohexylamino groups, respectively. It can directly bind to and block the transcription activity of the active forkhead box protein O1 (Foxo1), but not the Ser256-phosphorylated form. It induces cell death and growth arrest in Burkitt lymphoma cell lines at low concentrations.


S-benzyl-L-cysteinylglycine zwitterion

An S-conjugate L-cysteinylglycine zwitterion substituted by a benzyl group; major species at pH 7.3.


benzylcysteine

An S-conjugate L-cysteine zwitterion substituted by a benzyl group; major species at pH 7.3.


An S-conjugate L-cysteinylglycine zwitterion substituted by a (1-hydroxy-3-methylhexan-3-yl) group; major species at pH 7.3.


An S-conjugate L-cysteine zwitterion substituted by a (1-hydroxy-3-methylhexan-3-yl) group; major species at pH 7.3.


(R)-(+)-perillyl alcohol

A perillyl alcohol in which the chiral centre has R configuration.


(S)-methcathinone

A 2-methylamino-1-phenylpropan-1-one that has (S)-configuration.


abasic DNA-protein cross-linked residue

An organic group that is any protein residue cross-linked with an abasic site of DNA.


4-phospho-L-aspartate(2-) residue

Major species at pH 7.3.


D-cystine zwitterion

A cysteine zwitterion derived from D-cysteine by transfer of a proton from each of the carboxy groups to the amino groups.


neophytadiene

A diterpene that is 3-methylidenehexadec-1-ene substituted at positions 7, 11 and 15 by a methyl group.


name: an L-amino acyl-L-seryl dipeptide residue


name: an L-amino acyl-L-threonyl dipeptide residue


name: an L-amino acyl-L-cysteinyl dipeptide residue


An amino-acid residue that is formed when the carboxy group of any amino acid (where R is the side chain) undergoes a cyclodehydration reaction with a neighboring L-serine amino acid in a protein, resulting in the formation of a 2-oxazoline moiety.


An amino-acid residue that is formed when the carboxy group of any amino acid (where R is the side chain) undergoes a cyclodehydration reaction with a neighbouring L-serine amino acid in a protein, resulting in the formation of a 2-oxazoline ring which is dehydrogenated to the corresponding 1,3-oxazole moiety.


An amino-acid residue that is formed when the carboxy group of any amino acid (where R is the side chain) undergoes a cyclodehydration reaction with a neighboring L-cysteine amino acid in a protein, resulting in the formation of a 2-thiazoline moiety.