A steroidal acyl-CoA(4-) arising from deprotonation of the phosphate and diphosphate OH groups of (22E)-3-oxo-chola-4,22-dien-24-oyl-CoA; major species at pH 7.3.


name: short-chain (3S)-hydroxy fatty acyl-CoA(4-)

description: A (3S)-3-hydroxyacyl-CoA arising from deprotonation of the phosphate and diphosphate OH groups of any short-chain (3S)-hydroxy fatty acyl-CoA; major species at pH 7.3.


An alpha-amino-acid residue anion obtained by deprotonation of the carboxy groups of C-terminal-gamma-(L-glutamyl 5-semialdehyde)-L-2-glutamic acid group. Major structure at pH 7.3.


An alpha-D-glucoside that is the 2-aminoethyl glycoside of a disaccharide consisting of a beta- and an alpha-D-glucosyl residue linked (1->4).


An alpha-amino-acid residue anion obtained by deprotonation of the carboxy groups as well as protonatoin of the amino group of C-terminal-gamma-(L-ornithyl)-L-2-glutamic acid group. Major structure at pH 7.3.


An alpha-D-glucoside that is the 2-aminoethyl glycoside of a trisaccharide consisting of  beta-D-glucosyl, alpha-D-glucosyl and alpha-D-galactosyl residues linked sequentially (1->4).


L-alpha-phenylglycine zwitterion

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


N-acetyl-L-alpha-phenylglycinate

A monocarboxylic acid anion that is the conjugate base of N-acetyl-L-alpha-phenylglycine, obtained by deprotonation of the carboxy group; major species at pH 7.3.


(9R,10S)-dihydroxyoctadecanoic acid

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


A brassinosteroid that is 24-epi-cathasterone on which the hydroxy hydrogen at position 22 has been replaced by a sulfo group.


A class of glycoglycerolipids that consists of any 1,2-diacyl-sn-glycerol having an (alpha-D-galactopyranosyl)-(1->2)-(alpha-D-glucopyranosyl) glycosyl moiety attached at position 3.


A cholestanoid that zymosterol in which the two methyl groups at positions 26 and 27 have been replaced by a  cyclopropane ring.


An S-substituted glutathione in which the thiol hydrogen of glutathoine has been replaced by a 6-methylthiohexylhydroximoyl group.


A monohydroxybenzoic acid that is 2,5-dihydroxybenzoic acid in which the phenolic hydrogen at position 5 has been replaced by a beta-D-glucosyl residue.


A 3-(3-sn-phosphatidyl)-sn-glycerol 1-phosphate in which both phosphatidyl acyl groups are specified as hexadecanoyl (palmitoyl).


1-naphthyl beta-D-glucoside

A beta-D-glucoside that is beta-D-glucopyranose in which the anomeric hydroxy hydrogen has been replaced by a 1-naphthyl group.


An alpha-D-glucoside that is the 2-aminoethyl glycoside of a tetrasaccharide consisting of two beta-D-glucosyl residues, an alpha-D-glucosyl residue and (at the reducing end) an alpha-D-galactosyl residue, all linked sequentially (1->4).


A dipeptide that is cysteinylglycine in which the thiol hydrogen has been replaced by a 4-hydroxy-1-oxononan-3-yl group.


quercetin 3-beta-gentiobioside

A quercetin O-glycoside in which the hydroxy hydrogen at position 3 of quercetin has been replaced by a gentiobiosyl group.


An alpha-D-glucoside that is the 2-aminoethyl glycoside of a pentasaccharide consisting of  alpha-D-galactosyl, beta-D-glucuronosyl, beta-D-glucosyl, alpha-D-glucosyl and alpha-D-galactosyl residues, all linked sequentially (1->4).


quercetin 3-beta-gentiotrioside

A quercetin O-glycoside in which the hydroxy hydrogen at position 3 of quercetin has been replaced by a gentiotriosyl group.


An alpha-D-glucoside that is the 2-aminoethyl glycoside of a hexasaccharide consisting of alpha-D-glucosyl, alpha-D-galactosyl, beta-D-glucuronosyl, beta-D-glucosyl, alpha-D-glucosyl and alpha-D-galactosyl residues, all linked sequentially (1->4).


A 3-(4-hydroxycyclohex-2-en-1-ylidene)pyruvate obtained by deprotonation of the carboxy group of 3-[(1Z,4R)-4-hydroxycyclohex-2-en-1-ylidene]pyruvic acid; major species at pH 7.3.


A tetrahydro-4-hydroxyphenylpyruvate obtained by deprotonation of the carboxy group of 3-[(1R,4R)-4-hydroxycyclohex-2-en-1-yl]pyruvic acid; major species at pH 7.3.


A tetrahydro-4-hydroxyphenylpyruvate obtained by deprotonation of the carboxy group of 3-[(1S,4R)-4-hydroxycyclohex-2-en-1-yl]pyruvic acid; major species at pH 7.3.


kaempferol 3-beta-gentiobioside

A kaempferol O-glucoside in which the hydroxy hydrogen at position 3 of kaempferol has been replaced by a gentiobiosyl group.


A phosphatidylglycerol (18:1/16:1) in which the 1- and 2-acyl groups are specified as oleoyl and (3E)-hexadecenoyl respectively.


phosphatidylglycerol 34:3

A phosphatidylglycerol in which the two acyl groups contain 34 carbon atoms and 3 double bonds.


phosphatidylglycerol (18:2/16:1)

A phosphatidylglycerol 34:3 in which the acyl group at position 1 contains 18 carbons and two double bonds while that at position 2 contains 16 carbons and 1 double bond.


A phosphatidylglycerol (18:2/16:1) in which the 1- and 2-acyl groups are specified as linoleoyl and (3E)-hexadecenoyl respectively.


phosphatidylglycerol 34:4

A phosphatidylglycerol in which the two acyl groups contain 34 carbon atoms and 4 double bonds.


phosphatidylglycerol 18:3/16:1

A phosphatidylglycerol 36:1 in which the acyl group at position 1 contains 18 carbons and 3 double bonds while that at position 2 contains 16 carbons and 1 double bond.


A phosphatidylglycerol (18:3/16:1) in which the 1- and 2-acyl groups are specified as alpha-linolenoyl and (3E)-hexadecenoyl respectively.


A monogalactosyldiacylglycerol 34:4 in which the 1- and 2-acyl groups are specified as oleoyl and (7Z,10Z,13Z)-hexadecatrienoyl respectively.


A 3-[alpha-D-galactosyl-(1->6)-beta-D-galactosyl]-1,2-diacyl-sn-glycerol in which the 1- and 2-acyl groups are both specified as alpha-linolenoyl.


A 3-[alpha-D-galactosyl-(1->6)-beta-D-galactosyl]-1,2-diacyl-sn-glycerol in which the 1- and 2-acyl groups are both specified as linoleoyl.


A 3-[alpha-D-galactosyl-(1->6)-beta-D-galactosyl]-1,2-diacyl-sn-glycerol in which the 1- and 2-acyl groups are specified as alpha-linolenoyl and hexadecanoyl respectively.


4-thiouridine 5'-phosphate(1-) residue

An organic anionic group obtained by deprotonation of the phosphate OH group of 5-thiouridine 5'-phosphate residue; major species at pH 7.3.


An organic anionic group obtained by deprotonation of the phosphate OH group of 5-methyl-2-thiouridine 5'-phosphate residue; major species at pH 7.3.


phosphatidylglycerol (18:2/16:0)

A phosphatidylglycerol 34:2 in which the 1- and 2-acyl groups are specified as octadecadienoyl and hexadecanoyl respectively.


phosphatidylglycerol (18:3/16:0)

A phosphatidylglycerol 34:3 in which the 1- and 2-acyl groups are specified as octadecatrienoyl and hexadecanoyl respectively.


A phosphatidylglycerol (18:3/16:0) in which the 1- and 2-acyl groups are specified as alpha-linolenoyl and hexadecanoyl respectoively.


A hydroperoxyoctadecatrienoic acid that is (9Z,11E,14Z)-octadecatrienoic acid in which the hydroperoxy group is located at position 13S.


A member of the class of benzaldehydes in which the hydrogen at position 3 of benzaldehyde has been replaced by a methoxy group.


FLAMENOL

A member of the class of resorcinols that is phloroglucinol in which one of the phenolic hydrogens has been replaced by a methyl group.


alpha-allenylagmatine

A member of the class of guanidines that is agmatine in which one of the methylene hydrogens adjacent to the primary amino group has been replaced by an allenyl group.


carboxymethyl-CoA

An S-alkyl-CoA having carboxymethyl as the S-alkyl component.


2-hydroxyethyl hexadecanoate

A hexadecanoate ester obtained by the formal condensation of carboxy group of hexadecaoic acid with one of the hydroxy groups of ethylene glycol


A hydroxy monocarboxylic acid anion that is the conjugate base of 12-hydroxyjasmonic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


A 5-oxo monocarboxylic acid anion obtained by deprotonation of the carboxy and sulfate groups of 12-sulfojasmonic acid. Major species at pH 7.3


A 5-oxo monocarboxylic acid anion obtained by deprotonation of the carboxy and sulfate groups of 11-sulfojasmonic acid. Major species at pH 7.3


A 1,3-diglyceride in which both acyl groups are specified as octanoyl.


A 3-(3-sn-phosphatidyl)-sn-glycerol 1-phosphate in which the phosphatidyl acyl groups at positions 1 and 2 are specified as oleoyl and hexadecanoyl respectively.


beta-Asp-Glu

A dipeptide consisting of an L-aspartyl residue attached to L-glutamic acid via the beta-carboxy group.


N-isovaleryl-L-alanine

An N-acyl-L-alanine resulting from the formal condensation of carboxy group of isovaleric acid with the amino group of L-alanine.


5-hydroxyoctadecanoic acid

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


RNA polyanion 2',3'-cyclic phosphate

An ionic polymer obtained by global deprotonation of the phosphate OH groups of any RNA terminating in a 2',3'-cyclic phosphate. Major structure at pH 7.3


RNA polyanion nucleotide 2'-phosphate

An ionic polymer obtained by global deprotonation of the phosphate OH groups of any RNA terminating in a 2'-phosphate. Major structure at pH 7.3


A cyclic tetrasaccharide constructed from four alpha-glucopyranosyl residues joined by alternate alpha-(1->6)- and alpha-(1->3)-linkages.


A glucotetrose composed of two isomaltose units joined by an alpha-(1->3)-linkage.


mandelamide

A monocarboxylic acid amide that is phenylacetamide in which one of the benzylic hydrogens has been replaced by a hydroxy group.


A dipeptide zwitterion resulting from transfer of a proton from the carboxy to the amino group of any (E)-1-(glycyl-L-cystein-S-yl)-omega-(methylthio)alkylhydroximate; major species at pH 7.3.


XANTHOGALENOL

A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 6', a methoxy group at position 4' and a prenyl group at position 3'.


A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 2' and 4, methoxy group at positions 4' and 6' and a prenyl group at position 3'.


An aci-nitro compound resulting from the formal tautomerisation of the nitro group of (2-nitroethyl)benzene.


A dipeptide zwitterion resulting from transfer of a proton from the carboxy to the amino group of S-[(Z)-N-hydroxy-2-phenylethanimidoyl]-L-cysteinylglycine; major species at pH 7.3.


A dipeptide zwitterion resulting from transfer of a proton from the carboxy to the amino group of S-[(E)-N-hydroxy-2-(indol-3-yl)ethanimidoyl]-L-cysteinylglycine; major species at pH 7.3.


Cys(IAN)-Gly zwitterion

A dipeptide zwitterion resulting from transfer of a proton from the carboxy to the amino group of Cys(IAN)-Gly; major species at pH 7.3.


glycolaldehyde triphosphate(4-)

An organophosphate oxoanion obtained by removal of four protons from the triphosphate function of glycolaldehyde triphosphate; major species at pH 7.3.


A L-histidine derivative that is ergothioneine in which the thiol hydrogen has been replaced by a hydroxy group.


(R)-cyflumetofen

A 2-methoxyethyl 2-(4-tert-butylphenyl)-2-cyano-3-oxo-3-[2-(trifluoromethyl)phenyl]propanoate that has R configuration.


(S)-cyflumetofen

A 2-methoxyethyl 2-(4-tert-butylphenyl)-2-cyano-3-oxo-3-[2-(trifluoromethyl)phenyl]propanoate that has S configuration.


Cyflometofen

A nitrile that is acetonitrile in which the methyl hydrogens have been replaced by o-trifluoromethylbenzoyl, p-tert-butylphenyl, and (2-methoxyethoxy)carbonyl groups.


2-methoxyethyl ester

A carboxylic ester resulting from the formal condensation between a carboxylic acid and the hydroxy group of 2-methoxyethanol. In contrast to many other water-solubilising esters, the 2-methoxyethyl esters of many amino acids are crystalline, allowing them to be easily purified.


2-methoxyethyl group

An organyl group resulting from the formal cleavage of the hydroxy group from 2-methoxyethanol. It is used as a protecting group for carboxylic acids (in contrast to many other water-solubilising esters, the 2-methoxyethyl esters of many amino acids are crystalline, enabling them to be easily purified).


pheophytin a(1-)

A cyclic tetrapyrrole anion that is the carbanion obtained by removal of the acidic proton from position 21 of pheophytin a. Major species at pH 7.3


A cyclic tetrapyrrole anion obtained by deprotonation of the carboxy groups of nickel-sirohydrochlorin; major species at pH 7.3.


tenuazonic acid(1-)

An organic anion that is the carbanion obtained by removal of the acidic proton from position 3 of tenuazonic acid; major speies at pH 7.3.


3beta-hydroxy-Delta(5)-steroid group

An organic group derived from any 3beta-hydroxy-Delta(5)-steroid.


3-oxo-Delta(5)-steroid group

An organic group derived from any 3-oxo-Delta(5)-steroid.


A tertiary amino compound that is 2-(aminomethyl)-N,N-dimethylpropane-1,3-diamine in which the primary ammino groups have each been acylated by condensation with the carboxy group of 2-{3-[(1R)-3-(3,4-dimethoxyphenyl)-1-hydroxypropyl]phenoxy}acetic acid, the hydroxy groups of which have been esterified by condensation with the carboxy group of L-pipecolic acid, the nitrogen of which has been acylated by condensation with (2S)-2-(3,4,5-trimethoxyphenyl)butyric acid. It is a synthetic, cell-permeable ligand that can be used to induce homodimerization of fusion proteins containing the DmrB domain.


beta-bitter acid

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


3-oxo-Delta(4)-steroid group

An organic group derived from any 3-oxo-Delta(4)-steroid.


An aromatic ketone that is any 2-acylphloroglucinol in which both of the ring hydrogens have been replaced by prenyl groups.


colupulone

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


adlupulone

A beta-bitter acid in which the acyl group is specified as 2-methylbutanoyl.


3-hydroxyacyl group

Any univalent carboacyl group that is derived from a 3-hydroxycarboxylic acid.


A member of the class of fluorenes that is 9H-fluorene in which both of the hydrogens at position 9 have been replaced by p-hydroxyphenyl groups.


An alpha-amino-acid anion that is the conjugate base of O-succinyl-L-serine having anionic carboxy groups and a protonated amino group; major species at pH 7.3.


Any glycoside derived from N-acetyl-beta-D-glucosaminyl-(1->4)-N-acetyl-beta-D-glucosamine.


A tetrasaccharide consisting of beta-D-Delta(4)-glucopyranuronic acid, beta-D-glucopyranosyl, alpha-L-rhamnopyranosyl and D-glucopyranosyl residues, joined in sequence by (1->4), (1->4) and (1->3)-glycosidic bonds, respectively.


pyrrolopurine

Any organic heterotricyclic compound with a skeleton consisting of a pyrrole ring fused to a purine ring system.


Any oligosaccharide having a beta-D-glucose residue at the reducing end.


A secondary aliphatic ammonium ion obtained by protonation of both amino groups of piperazine.


A glycosylceramide in which the oligoglycosyl component can be any oligoglycosyl-(1->4)-beta-D-glucosyl residue.


An O-acyl carbohydrate that is beta-D-glucopyranose in which the anomeric hydroxy hydrogen has been replaced by a 3,4-dihydroxybenzoyl group.


A ribonucleotide residue(1-) obtained by deprotonation of the phosphate OH group of 5-hydroxy-UMP residue. Major microspecies at pH 7.4.


name: C2-C8-saturated long-chain fatty acyl pantetheine-4-phosphorylserine(1-) residue

description: An O-(S-[long-chain acyl]pantetheine-4'-phosphoryl)serine(1-) residue in which the S-acyl group is an C2-C8-saturated long-chain fatty acyl; major species at pH 7.3.


An organic anionic group obtained by deprotonation of the carboxy and phosphate OH groups of 5-(carboxymethoxy)uridine 5'-phosphate residue. Major microspecies at pH 7.4.


An organic anionic group obtained by deprotonation of the carboxy group of alpha-N-acetylneuraminosyl-(2->3)-beta-D-galactosyl-(1->4)-[alpha-L-fucosyl-(1->3)]-N-acetyl-D-glucosaminyl group.


An omega-carboxyacyl-CoA(5-) obtained by deprotonation of the phosphate, diphosphate and carboxy groups of any 3-carboxy-3-hydroxypropanoyl-CoA; major species at pH 7.3.


A steroid glucuronide anion that is the conjugate base of 17-epiestriol 3-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A steroid glucuronide anion that is the conjugate base of 17-epiestriol 17-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A steroid glucuronide anion that is the conjugate base of 17-epiestriol 16-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A steroid glucuronide anion that is the conjugate base of 16-epiestriol 3-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A steroid glucuronide anion that is the conjugate base of 16-epiestriol 16-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


nickel-sirohydrochlorin a,c-diamide(6-)

A cyclic tetrapyrrole anion obtained by deprotonation of the carboxy groups of nickel-sirohydrochlorin a,c-diamide; major species at pH 7.3.


A cyclic tetrapyrrole anion obtained by deprotonation of the carboxy groups of 15,17(3)-seco-F430-17(3)-acid; major species at pH 7.3.


5beta steroid

Any steroid that has beta-configuration at position 5.


A hydroxy monocarboxylic acid anion that is the conjugate base of 3-dimethylallyl-4-hydroxymandelic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


2'-unsubstituted isoflavones

An isoflavone that has an H at position 2'


A branched amino pentasaccharide compound consisting of a (C6H8O3)-(1->3)-[D-GalNAc-(1->2)-L-Fuc-(1->4)]-D-GlcNAc moiety attached to N-acetyl-D-galactosaminitol via a (1->3)-linkage. The unknown residue C6H8O3 is tentatively assigned by the authors of PMID:2817893 as 'an unsaturated hexosyl residue'.


A polysaccharide composed of a backbone of linear trisaccharide repeating units consisting of alpha-L-rhamnose, alpha-D-galactose and alpha-D-mannose residues linked sequentially (1->3) and (1->2), the repeating units being joined to each other via alpha(1->2)-linkages; corresponds to the backbone of the O-antigen repeat unit of the O:12 antigen common to Salmonella serogroups A, B and D.


A steroid glucuronide anion that is the conjugate base of chenodeoxycholic acid 3-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid functions; major species at pH 7.3.


A nucleotide-sugar oxoanion obtained by deprotonation of the diphosphate OH groups of dTDP-L-rhamnose; major species at pH 7.3.


An organic anionic group obtained by deprotonation of the triphosphate OH groups of any 5'-(5'-triphosphoguanosine)-(purine-ribonucleotide) residue; major species at pH 7.3.


An anionic amino-acid residue consisting of an O-(S-acylpantetheine-4'-phosphoryl)-L-serine residue in which the S-acyl group is specified as (3S)-hydroxy-3-methylglutaryl.


A methyl glycoside in which the glycosyl moiety consists of three alpha-D-galactosyl-(1->2)-[alpha-abequosyl-(1->3)]-alpha-D-mannosyl-(1->4)-alpha-L-rhamnosyl tetrasaccharide units all linked sequentially (1->4). Corresponds to the O polysaccharide of Salmonella Typhimurium, a serogroup B nontyphoidal Salmonella serovar.


A steroid glucuronide anion that is the conjugate base of chenodeoxycholic acid 24-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A steroid glucuronide anion that is the conjugate base of cholic acid 24-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A steroid glucuronide anion that is the conjugate base of deoxycholic acid 24-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A steroid glucuronide anion that is the conjugate base of lithocholic acid 24-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A steroid glucuronide anion that is the conjugate base of hyodeoxycholic acid 24-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A steroid glucuronide anion that is the conjugate base of hyocholic acid 24-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A steroid glucuronide anion that is the conjugate base of hyodeoxycholic acid 6-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid functions; major species at pH 7.3.


hyocholate 6-O-(beta-D-glucuronide)(2-)

A steroid glucuronide anion that is the conjugate base of hyocholic acid 6-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid functions; major species at pH 7.3.


name: (7S)-7-hydroxy-C2-C8-saturated long-chain fatty acyl pantetheine-4-phosphorylserine(1-) residue

description: An O-(S-[long-chain acyl]pantetheine-4'-phosphoryl)serine(1-) residue in which the S-acyl group is an (7S)-7-hydroxy-C2-C8-saturated long-chain fatty acyl; major species at pH 7.3.


name: (7R,8R)-7,8-dihydroxy-C2-C8-saturated long-chain fatty acyl pantetheine-4-phosphorylserine(1-) residue

description: An O-(S-[long-chain acyl]pantetheine-4'-phosphoryl)serine(1-) residue in which the S-acyl group is an (7R,8R)-7,8-dihydroxy-C2-C8-saturated long-chain fatty acyl; major species at pH 7.3.


ginkgolide

Organic heterohexacyclic compounds that are diterpenoid trilactones found in the ginkgo tree (also known as the maidenhair tree, Ginkgo biloba). They have a cage skeleton consisting of six 5-membered rings (a spiro[4.4]nonane carbobicyclic ring, three lactones and a tetrahydrofuran ring) which includes a tert-butyl substituent. The ginkolides vary only in the number and positions of their hydroxy substituents.


An O-(S-acylpantetheine-4'-phosphoryl)-L-serine(1-) residue in which the S-acyl group is specified as 7-oxoheptanoyl. Major species at pH 7.3


An alpha-amino-acid residue cation obtained by protonation of the amino and imino nitrogens of N-(4-aminobutylidene)-L-lysine residue; major species at pH 7.3


A glycerophospholipid, where R1 and R2 are acyl chains and R3 any of the groups that represent the different phospholipid classes (choline, ethanolamine, glycerol, etc).


A glycerophospholipid that is a lysophospholipid where only R1 or R2 is an acyl chain, the other is a hydrogen, and R3 is any group that represents the different classes of glycerophospholipids (choline, ethanolamine, inositol, etc).


A steroid glucuronide anion that is the conjugate base of 5alpha-dihydrotestosterone 17-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


dodecenol

A fatty alcohol containing 12 carbons and 1 double bond.


A steroid glucuronide anion that is the conjugate base of 5alpha-dihydrotestosterone 17-O-[beta-D-glucuronosyl-(1->2)-glucuronide] arising from deprotonation of the carboxylic acid functions; major species at pH 7.3.


N-isovalerylsarcosine

An N-acyl-amino acid resulting from the formal condensation of carboxy group of isovaleric acid with the amino group of sarcosine.


A polyunsaturated fatty acid that is octadecapentaenoic acid in which the five double bonds are located at positions 2, 4, 6, 8 and 10 (the all-trans-geoisomer).


A isothiocyanate that is hexane in which two of the terminal methyl hydrogens at positions 1 and 6 have been replaced by isothiocyanato and methylsulfanyl groups.


A monohydroxybenzoic acid that is 2,5-dihydroxybenzoic acid in which the phenolic hydrogen at position 2 has been replaced by a beta-D-glucosyl residue.


A desulfoglucosinolic acid resulting from the formal condensation of the thiol group of (3S)-N,3-dihydroxypent-4-enethioamide with beta-D-glucopyranose.


2-hydroxylinoleic acid

A 2-hydroxy fatty acid derived from linoleic acid.


An O-acyl carbohydrate obtained by formal condensation of the carboxy group of 2-oxindole-3-acetic acid with the anomeric hydroxy group of beta-D-glucose.


A steroid glucuronide anion that is the conjugate base of 2-hydroxy-17beta-estradiol 3-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A member of the class of indoles that is 1H-indole carrying methoxy and isothiocyanatomethyl substituents at positions 1 and 3 respectively.


A steroid glucuronide anion that is the conjugate base of 2-hydroxy-17beta-estradiol 2-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


2-trans-4'-dihydroabscisic acid

An apo carotenoid sesquiterpenoid that is 2-trans-abscisic acid in which the keto group at position 4' has been reduced to the corresponding alcohol.


An organic cation obtained by protonation of the amino group of 4-methoxy-3-indolylmethylamine.


A steroid glucuronide anion that is the conjugate base of 4-hydroxy-17beta-estradiol 3-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A steroid glucuronide anion that is the conjugate base of 4-hydroxy-17beta-estradiol 4-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A member of the class of indoles that is 1H-indole carrying isothiocyanatomethyl and methoxy substituents at positions 3 and 4 respectively.


An N-acyl-amino acid obtained by formal condensation of the carboxy group of 6-hydroxyindole-3-acetic acid with the amino group of phenylalanine.


An indole phytoalexin that is camalexin in which the hydrogen at position 6 on the indole fragment has been replaced by a methoxy group.


6-(methylthio)hexanonitrile oxide

A nitrile oxide that is pentane in which two of the terminal methyl hydrogens at positions 1 and 5 have been replaced by oxidonitrile and methylsulfanyl groups.


A glucosinolic acid that is glucoraphenin in which the hydroxy hydrogen at position 6 on the glucose fragment has been replaced by a sinapoyl group.


A member of the class of oxindoles that is 7-hydroxy-2-oxindole-3-acetic acid in which the phenolic hydrogen has been replaced by a beta-D-glucosyl residue.


7-(methylthio)heptanonitrile oxide

A nitrile oxide that is hexane in which two of the terminal methyl hydrogens at positions 1 and 6 have been replaced by oxidonitrile and methylsulfanyl groups.


An omega-(methylsulfany)alkyl desulfoglucosinolate in which the omega-(methylsulfany)alkyl group is specified as 7-(methylsulfanyl)heptyl.


An isothiocyanate that is octane in which two of the terminal methyl hydrogens at positions 1 and 8 have been replaced by isothiocyanato and methylsulfanyl groups.


An S-substituted L-cysteine in which the thiol hydrogen of L-cysteine has been replaced by a 9-(methylthio)nonylhydroximoyl group.


CONIFERYALDEHYDE GLUCOSIDE

A beta-D-glucoside that is coniferaldehyde in which the phenolic hydrogen has been replaced by a beta-D-glucosyl residue.


An omega-(methylsulfany)alkyl desulfoglucosinolate in which the omega-(methylsulfany)alkyl group is specified as 5-(methylsulfanyl)pentyl.


desulfoglucoiberin

A desulfoglucosinolic acid resulting from the formal condensation of the thiol group of N-hydroxy-3-(methylsulfinyl)butanethioamide with beta-D-glucopyranose.


An omega-(methylsulfany)alkyl desulfoglucosinolate in which the omega-(methylsulfanyl)alkyl group is specified as 6-(methylsulfanyl)hexyl.


A desulfoglucosinolic acid resulting from the formal condensation of the thiol group of N-hydroxypent-4-enethioamide with beta-D-glucopyranose.


desulfogluconasturtiin

A desulfoglucosinolic acid resulting from the formal condensation of the thiol group of N-hydroxy-3-phenylpropanethioamide with beta-D-glucopyranose.


desulfosinigrin

A desulfoglucosinolic acid resulting from the formal condensation of the thiol group of N-hydroxybut-3-enethioamide with beta-D-glucopyranose.


glucohesperin

An omega-[(methylsulfiny)alkyl]glucosinolic acid in which the omega-(methylsulfinyl)alkyl group is specified as 6-(methylsulfinyl)hexyl.


raphanusamic acid

A thiazolidinemonocarboxylic acid that is 2-thioxo-1,3-thiazolidine with the carboxy group located at position 4 (the R-enantiomer).


An organophosphate oxoanion obtained by deprotonation of the diphosphate OH groups of any ditrans,polycis-polyprenyl diphosphate; major species at pH 7.3.


peptidylamidoglycolate zwitterion

A peptide zwitterion obtained by transfer of a proton from the carboxy to the amino terminus of any peptidylamidoglycolate; major species at pH 7.3.


A peptide cation obtained by protonation of the amino terminus of any peptidylamide; major species at pH 7.3.


(omega-1)-methyl-branched lipid

A methyl-branched lipid having at least one methyl group  branched at C(omega-1) and either a single or a double bond between C(omega-1)  and C(omega-2). The class includes both (omega-1)-methyl-branched fatty acids and derivatives.


A methyl-branched lipid having an OH group at position Comega, at least one methyl group  branched at C(omega-1) and either a single or a double bond between C(omega-1)  and C(omega-2). The class includes both (omega-1)-methyl-branched fatty alcohols and derivatives.


A steroid glucuronide anion that is the conjugate base of lithocholic acid 3-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid functions; major species at pH 7.3.


A steroid acid anion that has a carboxylate group located at the 4alpha-position together with a hydroxy substituent located at the 3beta-position. Major microspecies at pH 7.4.


A steroid glucuronide anion that is the conjugate base of 2-hydroxyestrone 3-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A steroid glucuronide anion that is the conjugate base of 2-hydroxyestrone 2-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A steroid glucuronide anion that is the conjugate base of 4-hydroxyestrone 3-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A steroid glucuronide anion that is the conjugate base of estrone 4-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A steroid glucuronide anion that is the conjugate base of 2-methoxyestrone 3-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A 17-oxo steroid that is estrone in which the hydrogen at position 4 has been replaced by a methoxy group.


A steroid glucuronide anion that is the conjugate base of 4-methoxyestrone 3-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A steroid glucuronide anion that is the conjugate base of 2-methoxy-17beta-estradiol 3-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A 17beta-hydroxy steroid that is 17beta-estradiol in which the hydrogen at position 4 has been replaced by a methoxy group.


A steroid glucuronide anion that is the conjugate base of 4-methoxy-17beta-estradiol 3-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A 7-methyl guanosine (m7G) linked via an inverted 5'-5' triphosphate bridge to an initiating 2'-O-methyl-purine-ribonucleotide-ribonucleotide; major species at pH 7.3


A 7-methyl guanosine (m7G) linked via an inverted 5'-5' triphosphate bridge to an initiating 2'-O-methyl-purine-ribonucleotide-2'-O-methyl-ribonucleotide; major species at pH 7.3


isowyosine 5'-monophosphate(1-) residue

An organic anionic group obtained by deprotonation of the phosphate OH group of isowyosine 5'-monophosphate residue; major species at pH 7.3.


2-hydroxy-3-O-methyl estrone

A 2-hydroxy steroid that is 2-hydroxyestrone in which the hydroxy group at position 3 has been converted to the corresponding methyl ether.


A steroid glucuronide anion that is the conjugate base of 5alpha-androstane-3beta,17beta-diol 17-O-(beta-D-glucuronide) arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


5alpha-dihydrotestosterone sulfate(1-)

A steroid sulfate oxoanion that is the conjugate base of 5alpha-dihydrotestosterone sulfate, obtained by deprotonation of the sulfo group; major species at pH 7.3.


A steroid sulfate oxoanion that is the conjugate base of (3beta,5alpha,17beta)-3-hydroxyandrostan-17-yl sulfate, obtained by deprotonation of the sulfo group; major species at pH 7.3.


S-prenyl-L-cysteine zwitterion

An L-alpha-amino acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of S-prenyl-L-cysteine; major species at pH 7.3.


A hydroxy fatty-acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 2-hydroxyhexacosanoic acid.


An L-glutamic acid derivative obtained by replacement of one of the amino hydrogens of L-glutamic acid has been replaced by a (2S)-2-amino-2-carboxyethyl group.


An N-(polyunsaturated fatty acyl)ethanolamine obtained by formal epoxidation across the 5,6-double bond of anandamide.


An N-(polyunsaturated fatty acyl)ethanolamine obtained by formal epoxidation across the 8,9-double bond of anandamide.


An N-(polyunsaturated fatty acyl)ethanolamine obtained by formal epoxidation across the 11,12-double bond of anandamide.


An N-(polyunsaturated fatty acyl)ethanolamine obtained by formal epoxidation across the 14,15-double bond of anandamide.


An N-(polyunsaturated fatty acyl)ethanolamine that is anandamide in which one of the methyl hydrogens at position 20 has been replaced by a hydroxy group.


staphyloferrin B(2-)

A tricarboxylic acid dianion obtained by deprotonation of the three carboxy groups and protonation of the amino group of staphyloferrin B; major species at pH 7.3.


A glutathione conjugate in which the thiol hydrogen of glutathione has been replaced by a 2,5-dihydroxyphenyl group.


An  aromatic ether that is the derivative of 2-phenylethylamine with methoxy substituents at the 3- and 4-positions. It is an alkaloid isolated from the Cactaceae family.


A fatty acid ester obtained by formal condensation of the carboxy group of oleic acid with the hydroxy group of 9-hydroxyoctadecanoic acid.


L-polyhomomethionine

A class of sulfur-containing amino acids consisting of homologues of methionine where there is a minimum of four methylene groups between the alpha-carbon and sulfur atoms.


L-dihomomethionine

An L-polyhomomethionine in which there are four methylene groups between the alpha-carbon and sulfur atoms.


L-trihomomethionine

An L-polyhomomethionine in which there are five methylene groups between the alpha-carbon and sulfur atoms.


C-terminal Xaa-Gly(1-) residue

An organic anionic group obtained by deprotonation of the OH group of C-terminal Xaa-Gly residue


name: C-terminal alpha-amino-acid amide residue

description: An alkylamino group derived from any alpha-amino-acid amide.


L-tetrahomomethionine

An L-polyhomomethionine in which there are six methylene groups between the alpha-carbon and sulfur atoms.


An organic anionic group obtained by deprotonation of the OH group of C-terminal Xaa-hydroxyglycino residue.


L-pentahomomethionine

An L-polyhomomethionine in which there are seven methylene groups between the alpha-carbon and sulfur atoms.


L-hexahomomethionine

An L-polyhomomethionine in which there are eight methylene groups between the alpha-carbon and sulfur atoms.


N-hydroxy-L-polyhomomethionine

A class of N-hydroxy-alpha-amino-acids consisting of homologues of N-hydroxymethionine where there is a minimum of four methylene groups between the alpha-carbon and sulfur atoms.


N,N-dihydroxy-L-polyhomomethionine

A class of N,N-dihydroxy-alpha-amino-acids consisting of homologues of N,N-dihydroxymethionine where there is a minimum of four methylene groups between the alpha-carbon and sulfur atoms.


A 1-(alk-1Z-enyl)-sn-glycero-3-phospho-(N-acyl)ethanolamine(1-) obtained by deprotonation of the phosphate OH group of 1-O-(1Z-octadecenyl)-sn-glycero-3-phospho-(N-hexadecanoyl)ethanolamine; major species at pH 7.3.


A 1-(alk-1Z-enyl)-sn-glycero-3-phospho-(N-acyl)ethanolamine(1-) obtained by deprotonation of the phosphate OH group of 1-(1Z-octadecenyl)-sn-glycero-3-phospho-(N-oleoyl)ethanolamine; major species at pH 7.3.


resolvin T1

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


A beta-diketone obtained by formal oxidation of the 2 and 4 hydroxy groups of scyllo-inositol to the corresponding ketones.


A 1-(alk-1Z-enyl)-sn-glycero-3-phospho-(N-acyl)ethanolamine(1-) obtained by deprotonation of the phosphate OH group of 1-(1Z-octadecenyl)-sn-glycero-3-phospho-(N-arachidonoyl)ethanolamine; major species at pH 7.3.


A 1-(Z)-alk-1-enyl-sn-glycero-3-phosphate(2-) obtained by deprotonation of the phosphate OH groups of any 1-(1Z-octadecenyl)-sn-glycero-3-phosphate; major species at pH 7.3.


resolvin T2

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


resolvin T3

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


resolvin T4

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


A 5(),6(S)-epoxy-18-hydroxy-(7E,9E,11Z,14Z,16E)-icosapentaenoic acid in which the 18-hydroxy group has S-configuration.


N-hydroxy-L-dihomomethionine

An N-hydroxy-L-polyhomomethionine in which there are four methylene groups between the alpha-carbon and sulfur atoms.


N-hydroxy-L-trihomomethionine

An N-hydroxy-L-polyhomomethionine in which there are five methylene groups between the alpha-carbon and sulfur atoms.


N-hydroxy-L-tetrahomomethionine

An N-hydroxy-L-polyhomomethionine in which there are six methylene groups between the alpha-carbon and sulfur atoms.


N-hydroxy-L-pentahomomethionine

An N-hydroxy-L-polyhomomethionine in which there are seven methylene groups between the alpha-carbon and sulfur atoms.


N-hydroxy-L-hexahomomethionine

An N-hydroxy-L-polyhomomethionine in which there are eight methylene groups between the alpha-carbon and sulfur atoms.


N,N-dihydroxy-L-dihomomethionine

An N,N-dihydroxy-L-polyhomomethionine in which there are four methylene groups between the alpha-carbon and sulfur atoms.


N,N-dihydroxy-L-trihomomethionine

An N,N-dihydroxy-L-polyhomomethionine in which there are five methylene groups between the alpha-carbon and sulfur atoms.


N,N-dihydroxy-L-tetrahomomethionine

An N,N-dihydroxy-L-polyhomomethionine in which there are six methylene groups between the alpha-carbon and sulfur atoms.


N,N-dihydroxy-L-pentahomomethionine

An N,N-dihydroxy-L-polyhomomethionine in which there are seven methylene groups between the alpha-carbon and sulfur atoms.


An androstanoid that is 5alpha-dihydrotestosterone carrying an additional hydroxy susbstituent at position 19.


An androstanoid that is 5alpha-dihydrotestosterone carrying an additional oxo susbstituent at position 19.


N,N-dihydroxy-L-hexahomomethionine

An N,N-dihydroxy-L-polyhomomethionine in which there are eight methylene groups between the alpha-carbon and sulfur atoms.


(18S)-resolvin E2

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


name: cyclobutane pyrimidine dimer 5'-phosphate residue

description: A deoxyribonucleotide residue derived from cyclobutane pyrimidine dimer 5'-phosphate.


An androstanoid that is 5alpha-dihydrotestosterone carrying an additional hydroxy susbstituent at position 18.


(18S)-resolvin E1

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


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 8,9-epoxy-(5Z,11Z,14Z)-icosatrienoic acid.


short chain fatty acyl-CoA(4-)

A fatty acyl-CoA(4-) arising from deprotonation of the phosphate and diphosphate OH groups of any short-chain fatty acyl-CoA; major species at pH 7.3.


The monoprotonated form of quinine, the predominant species at pH7.3.


An L-isoleucine derivative resulting from the formal condensation of the carboxy group of (+)-7-isojasmonic acid with the amino group of L-isoleucine.


An L-isoleucine derivative resulting from the formal condensation of the carboxy group of (+)-12-hydroxy-7-isojasmonic acid with the amino group of L-isoleucine.


A tripeptide consisting of Z-Val-Ala-Asp(OMe) in which the C-terminal OH group has been replaced by a fluoromethyl group. An irreversible pan-caspase inhibitor.


A 3-oxo-Delta(4) steroid that is progesterone substituted by hydroxy groups at positions 6, 16 and 17 (6beta,16alpha,17alpha-stereoisomer).


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 11,12-epoxy-(5Z,8Z,14Z)-icosatrienoic acid.


A pregnane sterol that is pregnenolone substituted by two hydroxy groups at positions 16 and 17 (16alpha,17alpha-stereoisomer).


acetoacetic acid

A 3-oxo monocarboxylic acid anion that is the conjugate base of acetoacetic acid, arising from deprotonation of the carboxy group.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 14,15-epoxy-(5Z,8Z,11Z)-icosatrienoic acid.


name: DNA with 3-terminal trans-a,b-unsaturated sugar


A cholestanoid that is desmosterol carrying an additional hydroxy susbstituent at position 26.


A cholestanoid that is 7-dehydrocholesterol carrying an additional hydroxy substituent at position 25.


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


A cholestanoid that is 7-dehydrocholesterol carrying an additional hydroxy substituent at position 24 (24S-stereoisomer).


A cholestanoid that is 5alpha-cholestan-3beta-ol carrying an additional oxo substituent at position 7.


cholestanol 7alpha,8alpha-epoxide

A cholestanoid that is lathosterol in which the double bond at position 7,8 has been oxidised to the corresponding epoxide (the 7alpha,8alpha stereoisomer).


galunisertib

A pyrrolopyrazole that is 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole which is substituted at positions 2 and 3 by 6-methylpyridin-2-yl and 6-(aminocarbonyl)quinolin-4-yl groups, respectively. A Transforming growth factor-betaRI (TGF-betaRI) kinase inhibitor, it blocks TGF-beta-mediated tumor growth in glioblastoma.


The carbohydrate acid derivative anion formed from beta-D-GlcA3S-(1->3)-beta-D-Gal-(1->4)-D-GlcNAc by loss of two protons, one from each of its sulfo and carboxy groups.


A beta-D-galactoside that is the 4-methoxyphenyl glycoside of a disaccharide consisting of a 3-O-sulfo-beta-D-glucuronic acid residue linked (1->3) to beta-D-galactose.


The carbohydrate acid derivative anion formed from beta-D-GlcA3S-(1->3)-beta-D-Gal-OC6H4-4-OMe by loss of two protons, one from each of its sulfo and carboxy groups.


A beta-D-galactoside that is the 4-methoxyphenyl glycoside of a disaccharide consisting of a beta-D-glucuronic acid residue linked (1->3) to beta-D-galactose.


The carbohydrate acid derivative anion formed from beta-D-GlcA-(1->3)-beta-D-Gal-OC6H4-4-OMe by loss of a proton from its carboxy group.


A beta-D-galactoside that is the 4-[2-(4-sulfanylbutanamido)ethyl]phenyl glycoside of a disaccharide consisting of a 3-O-sulfo-beta-D-glucuronic acid residue linked (1->3) to beta-D-galactose.


The carbohydrate acid derivative anion formed from beta-D-GlcA3S-(1->3)-beta-D-Gal-OC6H4-4-[CH2]2NHC(O)[CH2]3SH by loss of two protons, one from each of its sulfo and carboxy groups.


An androstanoid that is testosterone carrying an additional hydroxy substituent at the 1beta-position. A metabolite of testosterone.


An androstanoid that is testosterone carrying an additional hydroxy substituent at the 2beta-position.


A random copolymer based on poly-L-lysine containing a disaccharide glycomimetic of the natural HNK-1 (human natural killer-1) glycoepitope. The proportions of the HNK-1 glycomimetic-modified poly-L-lysine component and the unmodified poly-L-lysine component (labelled m and m respectively in the diagram) are respectively x% and (100-x)%.


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


A fatty acid ester obtained by formal condensation of the carboxy group of oleic acid with the hydroxy group of 13-hydroxyoctadecanoic acid.


A fatty acid ester obtained by formal condensation of the carboxy group of (9Z)-hexadecenoic acid with the hydroxy group of 9-hydroxyoctadecanoic acid.


A fatty acid ester obtained by formal condensation of the carboxy group of (9Z)-hexadecenoic acid with the hydroxy group of 12-hydroxyoctadecanoic acid.


A fatty acid ester obtained by formal condensation of the carboxy group of (9Z)-hexadecenoic acid with the hydroxy group of 13-hydroxyoctadecanoic acid.


A beta-D-galactoside that is the methyl glycoside of a disaccharide consisting of a 3-O-sulfo-beta-D-glucuronic acid residue linked (1->3) to beta-D-galactose.


The carbohydrate acid derivative anion formed from beta-D-GlcA3S-(1->3)-beta-D-Gal-OMe by loss of two protons, one from each of its sulfo and carboxy groups.


12-(octadecanoyloxy)octadecanoic acid

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


13-(octadecanoyloxy)octadecanoic acid

A fatty acid ester obtained by formal condensation of the carboxy group of octadecanoic acid with the hydroxy group of 13-hydroxyoctadecanoic acid.


9-(octadecanoyloxy)octadecanoic acid

A fatty acid ester obtained by formal condensation of the carboxy group of octadecanoic acid with the hydroxy group of 9-hydroxyoctadecanoic acid.


A fatty acid ester obtained by formal condensation of the carboxy group of (9Z)-hexadecenoic acid with the hydroxy group of 5-hydroxyoctadecanoic acid.


A fatty acid ester obtained by formal condensation of the carboxy group of (9Z)-octadecenoic acid with the hydroxy group of 5-hydroxyoctadecanoic acid.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 5,6-epoxy-(8Z,11Z,14Z)-icosatrienoic acid.


A ketogluconate that is the conjugate base of 5-dehydro-L-gluconic acid, obtained by deprotonation of the carboxy group. Major microspecies at pH 7.3


A ketoaldonic acid phosphate consisting of (2xi)-3-deoxy-beta-D-threo-hept-6-ulopyranosonic acid carrying a single phospho substituent at position 7.


acetyl phosphate(1-)

An acyl monophosphate(1-) that is the conjugate base of acetyl dihydrogen phosphate.


A 3-oxo-5alpha-steroid that is 5alpha-estrane which is substituted by an oxo group at position 3, a hydroxy group at the 17beta position, and which has a double bond between positions 1 and 10. It is a 19-norsteroid arising from successive oxidation of dihydrotestosterone at C19.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 5-hydroxy-(6E,8Z,11Z,14Z)-icosatetraenoic acid.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 12-hydroxy-(5Z,8Z,10E,14Z)-icosatetraenoic acid.


A member of the class of thienotriazolodiazepines that is the tert-butyl ester of [(6S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl]acetic acid. An inhibitor of bromodomain-containing protein 4 that exhibits anti-cancer and cardioprotective properties.


N-carbamoyl-L-methioninate

An N-carbamoyl-L-alpha-amino acid anion obtained by deprotonation of the carboxy group of N-carbamoyl-L-methionine. Major microspecies at pH 7.3.


An L-5-monosubstituted hydantoin in which the substituent is specified as 2-(methylthio)ethyl.


TETRADECANAMIDE

A fatty amide of myristic acid.


An 8-{3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl}octanoic acid that has 1S,2S-configuration.


An O-acyl carbohydrate consisting of maltose carrying an anomeric O-acetyl substituent.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 15-hydroxy-(5Z,8Z,11Z,13E)-icosatetraenoic acid.


A D-5-monosubstituted hydantoin in which the substituent is specified as 2-(methylthio)ethyl.


N-carbamoyl-D-methioninate

An N-carbamoyl-D-alpha-amino acid anion obtained by deprotonation of the carboxy group of N-carbamoyl-D-methionine. Major microspecies at pH 7.3.


A (4Z,7Z,10Z,13Z,16Z)-19,20-epoxydocosapentaenoic acid with (19R,20S)-configuration.


A 6-acetamido-3-aminohexanoic acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of (3S)-6-acetamido-3-aminohexanoic acid; major species at pH 7.3.


A 16-HETE(1-) that is the conjugate base of 16(R)-HETE, obtained by deprotonation of the carboxy group; major species at pH 7.3.


A 16-HETE(1-) that is the conjugate base of 16(S)-HETE, obtained by deprotonation of the carboxy group; major species at pH 7.3.


An organophosphate oxoanion obtained by deprotonation of the diphosphate OH groups of alpha-D-mannosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-1-diphospho-ditrans,polycis-undecaprenol. Major species at pH 7.3.


An organophosphate oxoanion obtained by deprotonation of both free diphosphate OH groups of alpha-D-mannosyl-(1->3)-alpha-D-mannosyl-(1->3)-alpha-D-mannosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-1-diphospho-ditrans,polycis-undecaprenol; major species at pH 7.3.


A branched polysaccharide derivative composed of a backbone of repeating beta-D-Gal-(1->4)-beta-D-Glc-(1->6)-[alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->4)]-beta-D-GlcNAc units, joined by (1->3)-linkages as shown. Group B Streptococcus (GBS) type III capsular polysaccharide.


A glycoside that consists of four N-formyl-alpha-D-perosamine residues linked sequentially (1->2), (1->3) and (1->2) and linked at the reducing end glycosidically to a 5-(methoxycarbonyl)pentyl group.


prostaglandin E2 2-glyceryl ester

A 2-monoglyceride obtained by formal condensation of the carboxy group of prostaglandin E2 with the 2-hydroxy group of glycerol.


A glycoside that consists of three N-formyl-alpha-D-perosamine residues linked sequentially (1->2) and (1->3) and linked at the reducing end glycosidically to a 5-(methoxycarbonyl)pentyl group.


A glycoside that consists of three N-formyl-alpha-D-perosamine residues linked sequentially (1->3) and (1->2) and linked at the reducing end glycosidically to a 5-(methoxycarbonyl)pentyl group.


A glycoside that consists of two N-formyl-alpha-D-perosamine residues linked (1->3) and linked at the reducing end glycosidically to a 5-(methoxycarbonyl)pentyl group.


prostaglandin I2 2-glyceryl ester

A 2-monoglyceride obtained by formal condensation of the carboxy group of prostaglandin I2 with the 2-hydroxy group of glycerol.


prostaglandin F2alpha 2-glyceryl ester

A 2-monoglyceride obtained by formal condensation of the carboxy group of prostaglandin F2alpha with the 2-hydroxy group of glycerol.


A nucleotide-sugar oxoanion arising from deprotonation of the diphosphate OH groups of any UDP-2,3-diacyl-alpha-D-glucosamine; major species at pH 7.3.


An organophosphate oxoanion obtained by deprotonation of the phosphate OH groups of any 2,3-diacyl-alpha-D-glucosaminyl 1-phosphate. Major microspecies at pH 7.3


A glycoside that consists of an N-formyl-2,3-di-O-methyl-alpha-D-perosamine residue linked (1->3) to an N-formyl-alpha-D-perosamine residue which is linked glycosidically to a 5-(methoxycarbonyl)pentyl group.


An N(4)-glycosylated L-asparagine residue derived from N(4)-{beta-D-GlcNAc-(1->2)-alpha-D-Man-(1->3)-[beta-D-GlcNAc-(1->2)-alpha-D-Man-(1->6)]-beta-D-Man-(1->4)-beta-D-GlcNAcl-(1->4)-[alpha-L-Fuc-(1->3)]-beta-D-GlcNAc}-Asn.


A (4Z,7Z,10Z,13Z,16Z)-19,20-epoxydocosapentaenoic acid with (19S,20R)-configuration.


A glycoside that consists of an N-formyl-2-O-methyl-alpha-D-perosamine residue linked (1->3) to an N-formyl-alpha-D-perosamine residue which is linked glycosidically to a 5-(methoxycarbonyl)pentyl group.


An N(4)-glycosylated L-asparagine residue derived from N(4)-{beta-D-GlcNAc-(1->2)-alpha-D-Man-(1->3)-[beta-D-GlcNAc-(1->2)-alpha-D-Man-(1->6)]-[beta-D-Xyl-(1->2)]-beta-D-Man-(1->4)-beta-D-GlcNAcl-(1->4)-beta-D-GlcNAc}-Asn.


15(S)-HPETE 2-glyceryl ester

A 2-monoglyceride obtained by formal condensation of the carboxy group of 15(S)-HPETE with the 2-hydroxy group of glycerol.


A glycoside that consists of an N-formyl-2-O-methyl-alpha-D-perosamine residue and two N-formyl-alpha-D-perosamine residues linked sequentially (1->2) and (1->3) and linked at the reducing end glycosidically to a 5-(methoxycarbonyl)pentyl group.


acetylsalicylate

A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.


An EpETE obtained by formal epoxidation of the 8,9-double bond of all-cis-5,8,11,14,17-icosapentaenoic acid.


A glycoside that consists of an alpha-D-mannose residue linked (1->3) to an N-formyl-alpha-D-perosamine residue which in turn is linked glycosidically to a 5-(methoxycarbonyl)pentyl group.


1-pyrroline-5-carboxylic acid

A 1-pyrrolinecarboxylic acid that is 1-pyrroline in which one of the hydrogens at position 5 is replaced by a carboxy group.


A glycoside that consists of an alpha-D-mannose residue and three N-formyl-alpha-D-perosamine residues linked sequentially (1->2), (1->3) and (1->2) and linked at the reducing end glycosidically to a 5-(methoxycarbonyl)pentyl group.


A glycoside that consists of an alpha-D-mannose residue and five N-formyl-alpha-D-perosamine residues all linked sequentially (1->2) and linked at the reducing end glycosidically to a 5-(methoxycarbonyl)pentyl group.


A methyl glycoside that consists of a 4-O-(5-aminopentyl)-alpha-D-mannose residue and two N-formyl-alpha-D-perosamine residues linked sequentially (1->2) and (1->3) and linked at the reducing end glycosidically to a methyl group.


A methyl glycoside that consists of a 4-O-(5-aminopentyl)-alpha-D-mannose residue and three N-formyl-alpha-D-perosamine residues linked sequentially (1->2), (1->3) and (1->2) and linked at the reducing end glycosidically to a methyl group.


Brucella O-antigen

A diblock copolymer in which one block consists of tetrasaccharide components comprising N-formyl-alpha-D-perosamine residues linked sequentially (1->2), (1->3) and (1->2) [alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo-(1->3)-alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo], with the second block consisting of N-formyl-alpha-D-perosamine residues linked solely (1->2). The percentage of (1->3) linkages compared with (1->2) ranges from 1% to 20% in different Brucella biovars.


An N(4)-glycosylated L-asparagine residue derived from N(4)-{beta-D-GlcNAc-(1->2)-alpha-D-Man-(1->3)-[beta-D-GlcNAc-(1->2)-alpha-D-Man-(1->6)]-beta-D-Man-(1->4)-beta-D-GlcNAcl-(1->4)-[alpha-L-Fuc-(1->6)]-beta-D-GlcNAc}-Asn.


A thiohydroximic acid in which the C-substituent is specified as (3-indolyl)methyl (the E-geoisomer).


DNA without the base

DNA from which the base has been cleaved.


A branched amino decasaccharide comprising a sequence of alpha-sialyl, beta-D-galactosyl, N-acetyl-beta-D-glucosaminyl, beta-D-galactosyl, beta-D-glucosyl and 2,5-anydro-D-mannose residues linked sequentially (2->3), (1->4), (1->3), (1->4) and (1->6), to the N-acetyl-glucosaminyl residue of which is linked also (1->6) an alpha-sialyl-(2->3)-beta-D-galactosyl disaccharide unit, while to the 2,5-anhydro-D-mannose residue at the reducing end is also linked (1->4) a further alpha-sialyl(2->3)-beta-D-galactosyl disaccharide unit. Obtained by depolymerisation of the group B Streptococcus (GBS) type III capsular polysaccharide during which process the 2,5-anhydro-D-mannose residue is formed from a the original reducing-end N-acetyl-glucosaminyl residue (PMID:28439022).


ilomastat

An N-acyl-amino acid obtained by formal condensation of the carboxy group of (2R)-2-[2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoic acid with the amino group of N-methyl-L-tryptophanamide. A cell permeable broad-spectrum matrix metalloproteinase (MMP) inhibitor


A branched amino pentadecasaccharide comprising beta-D-galactosyl, beta-D-glucosyl and 2,5-anydro-D-mannose residues linked sequentially (1->4) and (1->6), to the galactosyl residue of which are linked (1->3) two units of beta-D-Gal-(1->4)-beta-D-Glc-(1->6)-[alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->4)]-beta-D-GlcNAc themselves linked (1->3). Obtained by depolymerisation of the group B Streptococcus (GBS) type III capsular polysaccharide during which process the 2,5-anhydro-D-mannose residue is formed from the original reducing-end N-acetyl-glucosaminyl residue (PMID:28439022).


A 1-alkyl-3-acyl-sn-glycerol that has octadec-9-en-1-yl as the alkyl group and octadec-9-enoyl as the acyl group.


A thia-alkylglucosinolic acid in which the thia-alkyl substituent can be any omega-(methylsulfanyl)alkyl group.


An alkylglucosinolic acid in which the alkyl substituent can be any omega-(methylsulfanyl)alkyl group.


A glutathione conjugate in which the mercapto hydrogen of glutathione has been replaced by an N-hydroxy-2-(indol-3-yl)ethanimidoyl group.


An EpETE obtained by formal epoxidation of the 11,12-double bond of all-cis-5,8,11,14,17-icosapentaenoic acid.


An EpETE obtained by formal epoxidation of the 14,15-double bond of all-cis-5,8,11,14,17-icosapentaenoic acid.


A glutathione conjugate in which the mercapto hydrogen of glutathione has been replaced by an N-hydroxy-2-phenylethanimidoyl group.


mycobilin a

A linear tetrapyrrole obtained by the enzymic degradation of heme by Mycobacterium tuberculosis enzyme MhuD.


biliverdin beta

A linear tetrapyrrole obtained by the enzymic degradation of heme by Pseudomonas aeruginosa heme oxygenase.


bacteriochlorophyllide e

A chlorophyllide obtained by hydrolysis of the terpenoid ester moiety of any bacteriochlorophyll e.


7,7-dihydroxybacteriochlorophyllide c

A chlorophyllide in which two of the methyl hydrogens at position 7 of any bacteriochlorophyllide c have been replaced by hydroxy groups.


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

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


An aminoalkylindole that is indole carrying a methylaminomethyl substituent at postion 3.


4-phospho-L-aspartic acid residue

An L-alpha-amino acid residue derived from 4-phospho-L-aspartic acid.


A 13-hydroxy-14,15-epoxy-(5Z,8Z,11Z)-icosatrienoate that is the conjugate base of 13(S)-hydroxy-(14S,15S)-epoxy-(5Z,8Z,11Z)-icosatrienoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


O-(alpha-D-mannosyl)-L-serine residue

An L-alpha-amino acid residue derived from O-(alpha-D-mannosyl)-L-serine.


An L-alpha-amino acid residue derived from O-(alpha-D-mannosyl)-L-threonine.


A 13-hydroxy-14,15-epoxy-(5Z,8Z,11Z)-icosatrienoate that is the conjugate base of 13-hydroxy-(14R,15S)-epoxy-(5Z,8Z,11Z)-icosatrienoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


A trihydroxyicosatrienoate that is the conjugate base of 13,14,15-trihydroxy-(5Z,8Z,11Z)-icosatrienoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


A trihydroxyicosatrienoate that is the conjugate base of 11,14,15-trihydroxy-(5Z,8Z,12E)-icosatrienoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


epoxy(hydroxy)icosatrienoate

An icosanoid anion obtained by the deprotonation of the carboxy group of any epoxy(hydroxy)icosatrienoic acid.


trihydroxyicosatrienoate

An icosanoid anion obtained by the deprotonation of the carboxy group of any trihydroxyicosatrienoic acid.


anaerobilin

A linear tetrapyrrole obtained by degradation of heme by an enzyme isolated from Escherichia coli O157:H7.


A sphingomyelin d18:1 in which the ceramide N-acyl group is specified as dodecanoyl (lauroyl).


A benzopteridine that is riboflavin in which the methyl group at position 8 has been replaced by an amino group.


A benzopteridine that is riboflavin in which the methyl group at position 8 has been replaced by a methylamino group.


A trihydroxyicosatrienoate that is the conjugate base of 11,12,15-trihydroxy-(5Z,8Z,13E)-icosatrienoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


An epoxy(hydroxy)icosatrienoate that is the conjugate base of 13-hydroxy-14,15-epoxy-(5Z,8Z,11Z)-icosatrienoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


(R)-2-(phosphonomethyl)malic acid

A dicarboxylic acid that is succinic acid in which the methylene hydrogens at position 2 have been replaced by phosphonomethyl and hydroxy groups (the R-enantiomer).


A HETE that is arachidonic acid carrying a hydroxy substituent at position 7.


A HETE that is arachidonic acid carrying a hydroxy substituent at position 13.


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


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


dihydroxydocosahexaenoic acid

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


A dihydroxydocosahexaenoic acid that is (4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoic acid in which the two hydroxy substituents are located at the 14S- and 22-positions.


A dihydroxydocosahexaenoic acid that is (4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoic acid in which the two hydroxy substituents are located at the 14R- and 22-positions.


A deoxyribonucleotide residue derived from 5-hydroxymethyldeoxycytidine 5'-monophosphate.


An organophosphate oxoanion obtained by deprotonation of the carboxy and phosphate OH groups of pyridinium-3,5-biscarboxylic acid mononucleotide; major species at pH 7.3.


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


An organophosphate oxoanion obtained by deprotonation of the carboxy and phosphate OH groups of 5-carboxy-1-(5-O-phosphono-beta-D-ribofuranosyl)pyridinium-3-carbonyl adenylate; major species at pH 7.3.


An organic anionic group obtained by deprotonation of the carboxy and phosphate OH groups of S-[5-carboxy-1-(5-O-phosphono-beta-D-ribofuranosyl)pyridinium-3-carbonyl]-L-cysteine residue


An organic anionic group obtained by deprotonation of the sulfanylcarbonyl and phosphate OH groups of S-[1-(5-O-phosphono-beta-D-ribofuranosyl)-5-(sulfanylcarbonyl)pyridinium-3-carbonyl]-L-cysteine residue.


An organophosphate oxoanion obtained by deprotonation of the sulfanylcarbonyl and phosphate OH groups of 1-(5-O-phosphono-beta-D-ribofuranosyl)-5-(sulfanylcarbonyl)pyridinium-3-carbonyl adenylate; major species at pH 7.3.


A member of the class of benzaldehydes carrying hydroxy and methoxy substituents at positions 2 and 5 respectively.


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


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


An epoxy(hydroxy)icosatrienoate that is the conjugate base of 11 hydroxy-(14R,15S)-epoxy-(5Z,8Z,12E)-icosatrienoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


A member of the class of pteridines that is pteridine in which the hydrogens at positions 2 and 4 are replaced by amino groups, whilst that at position 6 is replaced by a carbaldehyde group.


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


A member of the class of naphthaldehydes that is naphthalene-1-carbaldehyde substituted by a hydroxy group at position 2. Active core of sirtinol (CHEBI:73158).


20-hydroxyprostaglandin E2

A prostaglandin E derivative that is prostaglandin E2 in which one of the methyl hydrogens at position 20 has been replaced by a hydroxy group.


5-formylsalicylic acid

A monohydroxybenzoic acid in which a benzoic acid nucleus is substituted at positions 2 and 5 by a formyl group and an hydroxy group  respectively.


An organophosphate oxoanion obtained by deprotonation of the carboxy and phosphate OH groups of pyridinium-3,5-bisthiocarboxylic acid mononucleotide; major species at pH 7.3.


An organophosphate oxoanion obtained by deprotonation of the phosphate OH groups of Ni(II)-pyridinium-3,5-bisthiocarboxylic acid mononucleotide; major species at pH 7.3.


ACLONIFEN

A primary amino compound that is aniline in which the phenyl group has been substituted at positions 2, 3, and 6 by chlorine, phenoxy, and nitro groups, respectively. A protoporphyrinogen oxidase (PPO) inhibitor, it is used as a herbicide against a broad range of weeds in a wide range of crops.


long-chain fatty acyl-AMP

A fatty acyl-AMP that results from the formal condensation of the phosphoryl group of AMP with the carboxyl group of any long-chain fatty acid.


1,2-naphthoquinone-4-sulfonic acid

An arenesulfonic acid that is 1,2-naphthoquinone substituted at position 4 with a sulfonic acid group. Used principally as a reagent in colorimetric determinations.


An organic anionic group obtained by deprotonation of the phosphate OH groups of N(6)-(Ni(2+)-pyridinium-3,5-bisthiocarboxylate mononucleotide)-L-lysine residue.


prohexadione

A 4-oxo monocarboxylic acid that is cyclohexanecarboxylic acid which is substituted by oxo groups at positions 3 and 5, and by a propanoyl group at position 4. A plant growth regulator, it is used (commonly as the corresponding calcium salt, known as prohexadione-calcium) as an anti-lodging agent in small-grain cereals.


An organic anionic group obtained by deprotonation of the phosphate OH groups of Ni(II)-pyridinium-3,5-bisthiocarboxylate mononucleotide group


A  heteroarenecarbaldehyde in which a formyl group is located at position 6 of 2,3-dihydro-1,4-benzodioxine.


An O-acyl carbohydrate obtained by the formal condensation of the 20-carboxy group of 20-hydroxy-20-oxoleukotriene B4 with the anomeric hydroxy group of beta-D-glucuronic acid.


A member of the class of coumarins that is coumarin in which the hydrogen at position 3 is replaced by an acetyl group.


(24S)-hydroxycholesterol 24-sulfate

A steroid sulfate that is (24S)-24-hydroxycholesterol carrying a single sulfo substituent at the O-24 position.


thymidine 5'-monophosphate(1-) residue

An organic anionic group obtained by deprotonation of the phosphate OH group of dTMP residue. Major species at pH 7.3


4-O-methyl-dTMP(1-) residue

An organic anionic group obtained by deprotonation of the phosphate OH group of 4-O-methyl-dTMP residue. Major species at pH 7.3


(24S)-hydroxycholesterol 3-sulfate

A steroid sulfate that is (24S)-24-hydroxycholesterol carrying a single sulfo substituent at the O-3 position.


(24S)-hydroxycholesterol 3,24-disulfate

A steroid sulfate that is (24S)-24-hydroxycholesterol in which both hydroxy hydrogens have been replaced by sulfo groups.


19-hydroxyleukotriene B4(1-)

A leukotriene anion that is the conjugate base of 19-hydroxyleukotriene B4, obtained by deprotonation of the carboxy group; major species at pH 7.3.


18-hydroxyleukotriene B4(1-)

A leukotriene anion that is the conjugate base of 18-hydroxyleukotriene B4, obtained by deprotonation of the carboxy group; major species at pH 7.3.


Alexa Fluor 633

An organic molecular entity (structure not reported) that is a fluorescent dye with a maximum absorption wavelength at 632 nm and emission wavelength 647 nm. It is a bright and photostable far-red dye with excitation ideally suited to the 633 nm laser line. Alexa Fluor 633 succinimidyl ester is not suitable for labeling nucleic acids.


Alexa Fluor 647

An iminium betaine fluorescent dye with a max absorption wavelength 650 nm and emission wavelength 665 nm. Alexa Fluor 6 is a bright and photostable far-red dye with excitation ideally suited to the 633 nm laser line.


A pyridine nucleotide having 3,5-dicarboxypyridine as the nucleobase.


An acyclic mixed acid anhydride obtained by condensation of one of the carboxy group of pyridinium-3,5-biscarboxylic acid mononucleotide with the phosphste group of AMP.


An acyclic mixed acid anhydride obtained by condensation of one of the carboxy group of pyridinium-3-sulfanylcarbonyl-5-carboxylic acid mononucleotide with the phosphste group of AMP.


A pyridine nucleotide having pyridinium-3,5-bisthiocarboxylic acid as the nucleobase.


A nickel coordination entity obtained by complexation of nickel(II) with pyridinium-3,5-bisthiocarboxylic acid mononucleotide.


4'-adenylkanamycin A

A aminoglycoside phosphate obtained by formal condensation of the phosphate group of AMP with the 4'-hydroxy group of kanamycin A.


A hydroxycoumarin that is coumarin in which a hydroxy group replaces the hydrogen at position 4 and a chloro substituent replaces the hydrogen at position 6.


1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl group at position 1 is specified as hexanoyl.


A member of the class of benzimidazoles that is 1H-benzimidazole carrying a single hydroxy substituent at position 5.


(S)-2-halocarboxylic acid anion

A carboxylic acid anion obtained by deprotonation of the carboxy group of any (S)-2-halocarboxylic acid; major species at pH 7.3.


(R)-2-halocarboxylic acid anion

A carboxylic acid anion obtained by deprotonation of the carboxy group of any (R)-2-halocarboxylic acid; major species at pH 7.3.


A docosanoid anion obtained by deprotonation of the three carboxy groups and protonation of the glutamyl alpha-amino group of  (13R)-S-glutathionyl-(14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoic acid; major species at pH 7.3.


A docosanoid anion obtained by deprotonation of the two carboxy groups and protonation of the glutamyl alpha-amino group of (13R)-S-cysteinylglycinyl-(14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoic acid; major species at pH 7.3.


L-sorbose 1-phosphate(2-)

An organophosphate oxoanion obtained by deprotonation of the phosphate OH groups of L-sorbose 1-phosphate. Major microspecies at pH 7.3


A 1-palmitoyl-2-acyl-sn-glycero-3-phosphocholine in which the 2-acyl group is specified as (11Z,14Z,17Z)-icosatrienoyl.


A cholesteryl ester obtained by formal condensation of the carboxy group of (11Z,14Z,17Z)-icosatrienoic acid with the 3-hydroxy group of cholesterol.


3-O-acetylated rhamnogalacturonan I

A galacturonan derivative obtained by acetylation at position 3 of galacturonyl residues of rhamnogalacturonan I. A representative structure is shown.


secondary ammonium ion

An organic cation obtained by protonation of any secondary amino compound; major species at pH 7.3.


An organic anion derived from prohexadione by deprotonation of both the carboxy group and a hydroxy group of any of the enolate forms of the triketo moiety. The corresponding calcium salt, prohexadione-calcium, is used as an anti-lodging agent in small-grain cereals.


DEHYDROACETIC ACID

A pyran-2,4-dione substituted at position 3 by an acetyl group and at position 6 by a methyl group. A fungicide and bactericide it is used primarily in processed fruit and vegetables.


pyrandione

Any pyran compound that contains an unsaturated six-membered ring with one ring oxygen atom and two oxo substituents.


A pyrandione based on the structure of 2H-pyran-2,4(3H)-dione and its substituted derivatives.


An N-acylphosphatidylethanolamine(1-) in which the N-acyl group is specified as oleoyl; major species at pH 7.3.


an L-aminoacyl-L-amino acid zwitterion

Any peptide zwitterion comprising two L-amino acid residues. Major structure at pH 7.3.


methyl beta-(acetylthio)isobutyrate

A methyl ester derived from beta-(acetylthio)isobutyric acid.


(R)-3-(acetylthio)isobutyric acid

A monocarboxylic acid that is isobutyric acid in which a hydrogen of one of the methyl groups has been replaced by an acetylthio group (the R enantiomer). It is an important intermediate for the preparation of various angiotensin-converting enzyme inhibitors such as captopril and alacepril.


A monounsaturated fatty acid anion that is the conjugate base of (9Z)-heptadecenoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


A hydroxylamine that is N-hydroxyquinolin-4-one in which the hydrogen at position 2 has been replaced by a (1E)-non-1-en-1-yl group. It is the most active agent produced by Pseudomonas aeruginosa that modulates the growth and virulence of Staphylococcus aureus; the corresponding Z isomer is inactive.


A docosanoid anion that is the conjugate base of (13R,14S)-dihydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


furanochromone

An organic heterotricyclic compound that is chromone which is ortho-fused to a furan ring and its substituted derivatives thereof.


A docosanoid anion that is the conjugate base of (7R,14S)-dihydroxy-(4Z,8E,10E,12Z,16Z,19Z)-docosahexaenoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


A 3-oxo-fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 11-oxo-ETE.


An oxo-fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 15-oxo-ETE.


isonitramine

A azaspiro compound that is 2-azaspiro[5.5]undecane carrying a hydroxy substituent at position 7 (the 6R,7R-diastereomer). A synthetic Nitraria alkaloid.


The ketoaldonic acid phosphate formed formally from D-erythronic acid by oxidation of the 3-hydroxy group to an oxo group and phosphorylation at the 1-hydroxy group.


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

A  ketoaldonic acid that is butyric acid carrying an oxo substituent at position 2 as well as two hydroxy substituents at positions 3 and 4 (the S-enantiomer).


An omega-hydroxy fatty acid anion that is the conjugate base of 18-hydroxy-9,10-epoxyoctadecanoic acid arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A 9,10-epoxy-18-hydroxyoctadecanoate that is the conjugate base of (9S,10R)-9,10-epoxy-18-hydroxyoctadecanoic acid arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A 9,10-epoxy-18-hydroxyoctadecanoate that is the conjugate base of (9R,10S)-9,10-epoxy-18-hydroxyoctadecanoic acid arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A 9,10-epoxyoctadecanoate that is the conjugate base of (9R,10S)-9,10-epoxyoctadecanoic acid arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A 9,10-epoxyoctadecanoate that is the conjugate base of (9S,10R)-epoxyoctadecanoic acid arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A phosphatidylinositol mannoside consisting of two alpha-D-mannopyranose residues attached at positions 2 and 6 of 1-phosphatidyl-1D-myo-inositol via glycosidic linkages.


poly[(GA)]

A single-stranded RNA polynucleotide consisting of a repeating unit of deoxyguanosine and 5-methyldeoxyadenosine residues, with all residues connected by 3'-5' phosphodiester linkages.


An (omega-1)-hydroxy fatty acid anion that is the conjugate base of 9,10-epoxy-17-hydroxyoctadecanoic acid arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A tetrasaccharide composed from two alpha-D-Xyl-(1->6)-beta-D-Glc joined by a (->4)-linkage between the two Glc residues.


An octadecanoid anion that is the conjugate base of 9,10-epoxy-18-hydroxy-(12Z)-octadecenoic acid arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A branched nonasaccharide composed from six beta-D-glucosyl and three alpha-D-xylosyl residues


An octadecanoid anion that is the conjugate base of 18-hydroxy-12,13-epoxy-(9Z)-octadecenoic acid arising from deprotonation of the carboxylic acid function; major species at pH 7.3


optovin

A member of the class of thiazolidinone that is rhodanine in which the two methylene hydrogens have been replaced by a 2,5-dimethyl-1-(pyridin-3-yl)-1H-pyrrol-3-yl]methylidene group. A TRPA1 ligand that can be reversibly photoactivated.


TETROQUINONE

A hydroxybenzoquinone in which all four protons of the benzoquinone structure are substituted by hydroxy groups. A systemic keratolytic, it is normally supplied as its hydrate (CHEBI:137471).


An epoxy(hydroxy)icosatrienoate that is the conjugate base of 5,6-epoxy-20-hydroxy-(8Z,11Z,14Z)-eicosatrienoic acid arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


An epoxy(hydroxy)icosatrienoate that is the conjugate base of 8,9-epoxy-20-hydroxy-(5Z,11Z,14Z)-icosatrienoic acid arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


An epoxy(hydroxy)icosatrienoate that is the conjugate base of 20-hydroxy-11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


An icosanoid anion that is the conjugate base of 14,15-epoxy-20-hydroxy-(5Z,8Z,11Z)-icosatrienoic acid arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A (S)-3-hydroxyacyl-CoA(4-) arising from deprotonation of the phosphate and diphosphate OH groups of any 4-saturated-(3S)-hydroxyacyl-CoA; major species at pH 7.3.


A phosphatidylinositol mannoside consisting of alpha-D-mannopyranose and 6-acyl-alpha-D-mannopyranose residues attached at positions 2 and 6 respectively of 1-phosphatidyl-1D-myo-inositol via glycosidic linkages.


A monoterpenoid indole alkaloid that is a reactive intermediate in the biosynthesis of vindoline by Catharanthus roseus.


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

A ketoaldonic acid that is butyric acid carrying an oxo substituent at position 2 as well as two hydroxy substituents at positions 3 and 4 (the R-enantiomer).


An alpha-amino-acid cation obtained by deprotonation of the carboxy group and protonation of the amino groups of (2R,5S)-2,5-diaminohexanoic acid; major species at pH 7.3.


A steroid glucosiduronic acid that is 16alpha-hydroxyestrone in which the phenolic hydrogen has been replaced by a beta-D-glucuronyl residue.


A steroid glucosiduronic acid that is 16alpha-hydroxyestrone in which the hydroxy hydrogen at position 16 has been replaced by a beta-D-glucuronyl residue.


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


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


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


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


7-oxoresolvin D2(1-)

A docosanoid anion that is the conjugate base of 7-oxoresolvin D2, obtained by deprotonation of the carboxy group; major species at pH 7.3.


16-oxoresolvin D2(1-)

A docosanoid anion that is the conjugate base of 16-oxoresolvin D2, obtained by deprotonation of the carboxy group; major species at pH 7.3.


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

A ketoaldonic acid that is butyric acid carrying an oxo substituent at position 3 as well as two hydroxy substituents at positions 2 and 4 (the S-enantiomer).


quinoxaline herbicide

A quinoxaline pesticide that has herbicidal activity.


quizalofop-P

A 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid that has R configuration. An acetyl-CoA carboxylase inhibitor, it is used (generally as the corresponding ethyl or tefuryl ester proherbicides) for the control of annual and perennial grass weeds in sugar beet.


QUIZALOFOP

A monocarboxylic acid that is 2-phenoxypropanoic acid in which the phenyl group is substituted at the para position by a (6-chloroquinoxalin-2-yl)oxy group.


(S)-quizalofop

A 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid that has S configuration. It is the (inactive) enantiomer of the herbicide quizalofop-P.


A steroid acid anion that is the conjugate base of (2Z,10Z)-3-hydroxy-5,17-dioxo-4,5-secoestra-2,10-diene-3-oic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3. A meta-cleavage  metabolite in the estrogen degradation pathway.


(+)-isoafricanol

A tricyclic sesquiterpene with formula C15H26O, that is isolated from Streptomyces violaceusniger, S. malaysiensis and Leptographium lundbergii.


(-)-spiroviolene

A spirocyclic diterpene with formula C20H32 which is produced by a diterpene cyclase gene expressed in an engineered Streptomyces host.


A nucleotide-sugar oxoanion arising from deprotonation of the free diphosphate OH groups of CDP-D-ribulose. Major microspecies at pH 7.3.


A nucleotide-sugar oxoanion arising from deprotonation of the free diphosphate OH groups of CDP-D-ribose. Major microspecies at pH 7.3.


20-hydroxyprostaglandin E1

A prostaglandin E derivative that is prostaglandin E1 in which one of the methyl hydrogens at position 20 has been replaced by a hydroxy group.


tsukubadiene

A tricyclic diterpene with formula C20H32 which is produced by a diterpene cyclase gene expressed in an engineered Streptomyces host.


20-hydroxyprostaglandin A1

A prostaglandin A derivative that is prostaglandin A1 in which one of the methyl hydrogens at position 20 has been replaced by a hydroxy group.


A tricyclic sesquiterpene with formula C15H24 which is biosynthesised from farnesyl diphosphate by a diterpene cyclase enzyme from Dictyostelium discoideum.


A bicyclic sesquiterpene with formula C15H24 which is biosynthesised from farnesyl diphosphate by a diterpene cyclase enzyme from Dictyostelium discoideum.


A steroidal acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-oxochenodeoxycholic acid.


(-)-alpha-amorphene

A member of the cadinene family of sesquiterpenes having a 4,7-dimethyl-1-(propan-2-yl)-1,2,4a,5,6,8a-hexahydronaphthalene skeleton with 1S,4aR,8aS-stereochemistry. It is isolated from the essential oils of several plant species.


A choloyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-oxocholic acid.


(+)-corvol ether A

A tricyclic sesquiterpenoid with formula C15H26O which is biosynthesised from farnesyl diphosphate by a sesquiterpene cyclase enzyme from Kitasatospora setae.


A choloyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-oxodeoxycholic acid.


A choloyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-oxocholan-24-oic acid.


An L-alpha-amino acid residue derived from N-acetyl-beta-D-glucosaminyl-(1->4)-alpha-D-mannosyl-L-threonine.


N-propanoyl-L-methionine

An N-acyl-L-alpha-amino acid obtained by formal condensation of the carboxy group of propanoic acid with the amino group of L-methionine.


A dihydroxyicosatetraenoate that is the conjugate base of (5S,6R)-dihydroxy-(7E,9E,11Z,14Z)-icosatetraenoic acid arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


A bis(hydroperoxy)icosatetraenoate that is the conjugate base of (5S,15S)-dihydroperoxy-(6E,8Z,11Z,13E)-icosatetraenoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


bis(hydroperoxy)icosatetraenoate

An icosanoid anion arising from deprotonation of the carboxylic acid function of any dihydroperoxyicosatetraenoic acid; major species at pH 7.3.


pivaloyl-CoA

A short-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of pivalic acid.


An hydroperoxy(hydroxy)icosatetraenoate that is the conjugate base of (5S)-hydroxy-(15S)-hydroperoxy-(6E,8Z,11Z,13E)-icosatetraenoic acid; major species at pH 7.3.


An hydroperoxy(hydroxy)icosatetraenoate that is the conjugate base of (5S,6R)-dihydroxy-(15S)-hydroperoxy-(7E,9E,11Z,13E)-icosatetraenoic acid; major species at pH 7.3.


hydroperoxy(hydroxy)icosatetraenoate

An icosanoid anion that is any icosatetraenoate bearing hydroxy and hydroperoxy substituents. An oxidation product of icosatetraenoic acid metabolism.


A steroid acid anion, that is the conjugate base of pyridinestrone-3-carboxylic acid. An abiotic metabolite in the 4,5-seco pathway of aerobic estrogen degradation by the bacterium Sphingomonas sp. strain KC8.


N-(fatty acyl)-L-alpha-amino acid

An N-acyl-L-alpha-amino acid resulting from the formal condensation of the carboxy group of any fatty acid with the amino group of any L-amino acid.


A glycoside consisting of D-glyceric acid having a 6-O-octanoyl-alpha-D-glucosyl-(1->6)-alpha-D-glucosyl residue attached at position 2 via a glycosidic linkage.


A glycoside consisting of D-glyceric acid having an alpha-D-glucosyl-(1->6)-alpha-D-glucosyl residue attached at position 2 via a glycosidic linkage.


A dihydroxyicosatetraenoate  that is the conjugate base of (5S,6S)-dihydroxy-(7E,9E,11Z,14Z)-icosatetraenoic acid arising from deprotonation of the carboxylic acid function; major species at pH 7.3.


An epoxide fluorescent probe for use in in vivo visualization of hydrogen sulfide. The probe employs a fluorescein as a fluorophore, and is equipped with an operating epoxide unit. FEPO functions via epoxide ring opening via nucleophilic attack by H2S.


An organic heterotricyclic compound that is 9H-imidazo[1,2-a]benzimidazole which is substituted at positions 2, 3, and 9 by phenyl, 2,3-dimethoxycinnamoyl, and methyl groups, respectively. It is a potent activator of osteoblast differentiation.


(+)-eremophilene

A member of the classs of octahydronaphthalenes and a sesquiterpene that is 1,2,3,4,4a,5,6,7-octahydronaphthalene which is substituted by an isopropenyl group at position 3 and by methyl groups at positions 4a and 5 (the 3S,4aS,5R- diastereoisomer).


A sesquiterpene that is 1,2,3,3a,4,5,6,8a-octahydroazulene carrying methyl, methylidene and isopropyl substituents at positions 1, 4 and 7 respectively.


A sesquiterpenoid obtained formally from (-)-germacrene A by hydroxylation at position 6 and hydrogenation across the C(11)-C(12) double bond.


A tricyclic diterpene with formula C20H32 which is produced by a diterpene cyclase gene expressed in roots of Arabidopsis.


An 11-HETE(1-) that is the conjugate base of 11(S)-HETE, obtained by deprotonation of the carboxy group; major species at pH 7.3.


An enal obtained by formal dehydrogenation across positions 2 and 3 of any n-alkanal


A 2-acyl-sn-glycero-3-phosphoethanolamine zwitterion obtained by transfer of a proton from the phosphate to the amino group of 2-(11R)-hydroxy-(5Z,8Z,12E,14Z)-icosatetraenoyl-sn-glycero-3-phosphoethanolamine; major species at pH 7.3.


A 2-acyl-sn-glycero-3-phosphoethanolamine zwitterion obtained by transfer of a proton from the phosphate to the amino group of 2-[(5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dien-1-oyl]-sn-glycero-3-phosphoethanolamine; major species at pH 7.3.


A 2-acyl-sn-glycero-3-phosphocholine in which the acyl group is specified as (11R)-hydroxy-(5Z,8Z,12E,14Z)-icosatetraenoyl.


A 2-acyl-sn-glycero-3-phosphocholine in which the acyl group is specified as (15R)-hydroxy-(5Z,8Z,11Z,13E)-icosatetraenoyl.


A 2-acyl-sn-glycero-3-phosphocholine in which the acyl group is specified as (15S)-hydroxy-(5Z,8Z,11Z,13E)-icosatetraenoyl.


A 2-acyl-sn-glycero-3-phosphocholine in which the acyl group is specified as (5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dien-1-oyl


alkylamine

Any primary amine in which the substituent attached to nitrogen is an alkyl group.


A polyunsaturated fatty acyl-CoA(4-) obtained by deprotonation of the phosphate and diphosphate functions of (2E,4Z)-deca-2,4-dienoyl-CoA; major species at pH 7.3.


An organophosphate oxoanion that is the trianion arising from deprotonation of the phosphate and carboxylic acid functions of N-acetyl-alpha-D-muramate 1-phosphate. Major microspecies at pH 7.3.


An aminobenzoate that is the conjugate base of 4-aminosalicylic acid, obtained by deprotonation of the carboxy group. Major miscrospecies at pH 7.3.


long-chain 3-oxo-fatty acyl-CoA

A long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of any long-chain (C13 to C22) 3-oxo-fatty acid.


A member of the class of pteroates that is the conjugate base of 2-hydroxy-7,8-dihydropteroic acid, obtained by deprotonation of the carboxy group. Major microspecies at pH 7.3.


An amino disaccharide consisting of a 2,3-di-O-methyl-N-formyl-alpha-D-perosamine residue linked (1->3) to N-formyl-alpha-D-perosamine.


A glycosyl group formed formally by loss of the hydroxy group from the anomeric carbon of   alpha-D-Rhap2,3-Me24NFo-(1->3)-alpha-D-Rhap4NFo.


long-chain (3S)-hydroxy fatty acyl-CoA

A long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of any long-chain (C13 to C22) (3S)-hydroxy-fatty acid.


An icosanoid anion that is the conjugate base of (6E,8Z,11Z)-5-oxoicosatrienoic acid (5-oxo-ETrE), obtained by deprotonation of the carboxy group; major species at pH 7.3.


A steroidal acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (22E)-3-oxochola-4,22-dien-24-oic acid.


An amino disaccharide consisting of a 4-formamido-alpha-D-threo-pentopyranosyl residue linked (1->3) to anN-formyl-alpha-D-perosamine residue.


A glycosyl group formed by loss of the hydroxy group from the anomeric carbon of 4-formamido-alpha-D-threo-pentopyranosyl-(1->3)-N-formyl-alpha-D-perosamine.


short-chain (3S)-hydroxy fatty acyl-CoA

A short-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of any short-chain (C3 to C5) (3S)-hydroxy-fatty acid.


O-nonadecanoylcarnitine

An O-acylcarnitine having nonadecanoyl as the acyl substituent.


N-acetyl-L-alpha-phenylglycine

An N-acyl-L-alpha-amino acid that is L-alpha-phenylglycine in which a hydrogen attached to the nitrogen has been replaced by an acetyl group.


The glycosyl group formed formally by loss of the hydroxy group from the reducing-end anomeric carbon of alpha-D-Rhap4NFo-(1->3)-alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo.


A 3-(4-hydroxycyclohex-2-en-1-ylidene)pyruvic acid having 1Z,4R stereochemistry.


A tetrahydro-4-hydroxyphenylpyruvic acid with (1R,4R)-stereochemistry.


A tetrahydro-4-hydroxyphenylpyruvic acid with (1S,4R)-stereochemistry.


allocholate

A bile acid anion that is the conjugate base of allocholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


allodeoxycholate

A bile acid anion that is the conjugate base of allodeoxycholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


A steroidal acyl-CoA(4-) obtained by deprotonation of phosphate and diphosphate functions of allocholoyl-CoA; major species at pH 7.3.


A steroidal acyl-CoA(4-) obtained by deprotonation of phosphate and diphosphate functions of allodeoxycholoyl-CoA; major species at pH 7.3.


The glycosyl group formed formally by loss of the hydroxy group from the reducing-end anomeric carbon of alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo-(1->3)-alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo.


An amino trisaccharide consisting of three N-formyl-alpha-D-perosamine residues linked sequentially (1->2).


A glycosylglycerol derivative in which the glycosyl moiety is beta-D-glucopyranosyl-(1->6)-beta-D-galactopyranosyl attached at O-3, with O-1 and O-2 both acylated.


A steroidal acyl-CoA(4-) obtained by deprotonation of phosphate and diphosphate functions of beta-muricholoyl-CoA; major species at pH 7.3.


An S-conjugate in which the mercapto hydrogen of L-cysteinylglycine  has been replaced by an N-hydroxy-2-phenylethanimidoyl group.


A glycosyl group formed formally by loss of the hydroxy group from the anomeric carbon of alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo.


A glycosyl group formed formally by loss of the hydroxy group from the reducing-end anomeric carbon of alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo.


An S-conjugate in which the mercapto hydrogen of L-cysteinylglycine has been replaced by an N-hydroxy-2-(indol-3-yl)ethanimidoyl group.


A monocarboxylic acid anion obtained by deprotonation of the carboxy and sulfino groups of 3-sulfinopropionic acid. Major microspecies at pH 7.3


BENZENEMETHANETHIOL

A thiol that is toluene in which one of the methyl hydrogens has been replaced by a sulfanyl group.


thiobenzaldehyde

A thioaldehyde that is benzaldehyde in which the oxygen has been replaced by divalent sulfur.


Cys(IAN)-Gly

An S-conjugate in which the mercapto hydrogen of L-cysteinylglycine has been replaced by a cyano(indol-3-yl)methyl group.


glycolaldehyde triphosphate

A member of the class of aldehydes that is glycolaldehyde in which the hydroxy hydrogen has been replaced by a triphosphate group.


nickel-sirohydrochlorin

A metalloporphyrin that is sirohydrochlorin in which the four nitrogen atoms are bound to a central nickel atom.


A steroidal-CoA(4-) obtained by deprotonation of phosphate and diphosphate functions of ursodeoxycholoyl-CoA; major species at pH 7.3.


A glycosyl group formed formally by loss of the hydroxy group from the reducing-end anomeric carbon of alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo-(1->3)-alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo.


methylhistidine

A N(alpha)-methyl-L-histidines  that is L-histidine bearing a single methyl substituent at the N(alpha)-position.


glycolonitrile

An cyanohydrin that is acetonitrile in which one of the hydrogens has been replaced by a hydroxy group.


A carbohydrate derivative in which a tetrasaccharide derivative consisting of an alpha-D-rhamnose residue, two N-formyl-alpha-D-perosamine residues and a methyl N-formyl-alpha-D-perosaminide residue linked sequentially (1->2), (1->3) and (1->2) is linked to a protein, normally via a 3,4-diaminocyclobutane-1,2-dione-based linker attached to position 4 of the rhamnose residue at the non-reducing end.


A cholestanoid that is cholestanol substituted by a hydroxy group at position 24S.


A cholestanoid that is cholestanol which is substituted by a hydroxy group at position 26 and has R-configuration at position 25.


A carbohydrate derivative in which a tetrasaccharide derivative consisting of an alpha-D-rhamnose residue, five N-formyl-alpha-D-perosamine residues and a methyl N-formyl-alpha-D-perosaminide residue, all linked sequentially (1->2), is linked to a protein, normally via a 3,4-diaminocyclobutane-1,2-dione-based linker attached to position 4 of the rhamnose residue at the non-reducing end.


An amino tetrasaccharide consisting of an alpha-D-mannose residue and three N-formyl-alpha-D-perosamine residues linked sequentially (1->2), (1->3) and (1->2).


The glycosyl group formed formally by loss of the hydroxy group from the reducing-end anomeric carbon of alpha-D-Manp-(1->2)-alpha-D-Rhap4NFo-(1->3)-alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo.


rhosin

A D-tryptophan derivative obtained by formal condensation of the carboxy group of D-tryptophan with the amino group of (quinoxalin-6-yl)methylidenehydrazide. It directly targets the Rho GEF binding domain, thereby preventing Rho from interacting with its GEFs


A polyether that is 4,7,10-trioxatridecane substituted at positions 1 and 13 by an amino group and a 3-carboxypropanamido group respectively. Flexible and hydrophilic, it is used as an extended linker in solid-phase immunoassays.


Leu-Ser-Glu-Thr-Thr-D-Leu

A six-membered oligopeptide comprising L-leucine, L-serine, L-glutamic acid, L-threonine, L-threonine and D-leucine residues coupled in sequence.


Leu-Ser-Glu-Thr-Glu-Thr-D-Leu

A seven-membered oligopeptide comprising L-leucine, L-serine, L-glutamic acid, L-threonine, L-glutamic acid, L-threonine and D-leucine residues coupled in sequence.


A 3-hydroxyacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the 3-carboxy group of 3-carboxy-3-hydroxypropanoic acid.


17-epiestriol 3-O-(beta-D-glucuronide)

A steroid glucosiduronic acid that is 17-epiestriol having a single beta-D-glucuronic acid residue attached at position 3.


17-epiestriol 17-O-(beta-D-glucuronide)

A steroid glucosiduronic acid that is 17-epiestriol having a single beta-D-glucuronic acid residue attached at position 17.


17-epiestriol 16-O-(beta-D-glucuronide)

A steroid glucosiduronic acid that is 17-epiestriol having a single beta-D-glucuronic acid residue attached at position 16.


A nona-2,4,6-trienal in which all three double bonds adopt trans-configurations.


16-epiestriol 3-O-(beta-D-glucuronide)

A steroid glucosiduronic acid that is 16-epiestriol having a single beta-D-glucuronic acid residue attached at position 3.


16-epiestriol 16-O-(beta-D-glucuronide)

A steroid glucosiduronic acid that is 16-epiestriol having a single beta-D-glucuronic acid residue attached at position 16.


A cholanic acid conjugate anion that is the conjugate base of 7-oxotaurolithocholic acid, obtained by deprotonation of the sulfonic acid group; major species at pH 7.3.


A steroid glucosiduronic acid that is chenodeoxycholic acid  having a single beta-D-glucuronic acid residue attached at position 3.


TETRAGASTRIN

A tetrapeptide composed of L-tryptophan, L-methione, L-aspartic acid and L-phenylalaninamide residues joined in sequence.


5-formyl-dCMP(1-) residue

An organic anionic group obtained by deprotonation of the phosphate OH group of 5-formyl dCMP residue; major species at pH 7.3.


5-carboxy-dCMP(2-) residue

An organic anionic group obtained by deprotonation of the phosphate and carboxy groups of 5-carboxy-dCMP residue; major species at pH 7.3.


Val-Ala-Lys

A tripeptide composed of L-valine, L-alanine and L-lysine residues joined in sequence.