Zwitterionic form of creatine arising from transfer of a proton from the carboxy to the guanidino group; major species at pH 7.3.


dGMP dianion

A 2'-deoxyribonucleoside 5'-monophosphate(2-) obtained by deprotonation of the phosphate OH groups of 2'-deoxyguanosine 5'-monophosphate (dGMP).


DDIT3_HUMAN DNA damage-inducible transcript 3 protein (sprot)

A DNA damage-inducible transcript 3 protein that is encoded in the genome of human.


2'-Deoxyinosine 5'-phosphate(2-)

A 2'-deoxyribonucleoside 5'-monophosphate(2-) obtained by deprotonation of the phosphate OH groups of 2'-deoxyinosine 5'-monophosphate; major species at pH 7.3.


A 2'-deoxyribonucleoside 5'-triphosphate(4-) resulting from deprotonation of the triphosphate OH groups of 2'-deoxyuridine-5'-triphosphate (dUTP); major species at pH 7.3.


Uridine-diphosphate

A nucleoside 5'-diphosphate(3-) arising from deprotonation of the diphosphate OH groups of uridine 5'-diphosphate (UDP); major species at pH 7.3.


dUDP trianion

A 2'-deoxyribonucleoside 5'-diphosphate obtained by deprotonation of the diphosphate OH groups of 2'-deoxyuridine 5'-diphosphate (dUDP).


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


SYUA_HUMAN Alpha-synuclein (sprot)

An alpha-synuclein that is encoded in the genome of human.


LPIN1_HUMAN Phosphatidate phosphatase LPIN1 (sprot)

A phosphatidate phosphatase LPIN1 that is encoded in the genome of human.


HDAC3_HUMAN Histone deacetylase 3 (sprot)

A histone deacetylase 3 that is encoded in the genome of human.


UIMC1_HUMAN BRCA1-A complex subunit RAP80 (sprot)

A BRCA1-A complex subunit RAP80 that is encoded in the genome of human.


CDK4_HUMAN Cyclin-dependent kinase 4 (sprot)

A cell division protein kinase 4 that is encoded in the genome of human.


CDK6_HUMAN Cyclin-dependent kinase 6 (sprot)

A cyclin-dependent kinase 6 that is encoded in the genome of human.


FZR1_HUMAN Fizzy-related protein homolog (sprot)

A fizzy-related protein that is encoded in the genome of human.


NEDD8 ultimate buster 1 isoform h2 (human)

A NEDD8 ultimate buster 1 (human) that is a translation product of some mRNA whose exon structure and start site selection renders it capable of giving rise to a protein with the amino acid sequence represented by UniProtKB:Q9Y5A7-2.


(R)-mevalonate

The (R)-enantiomer of mevalonate.


A 3-oxo-5alpha- steroid that is zymosterol which has been substituted by a methyl group at C-4, and in which the 3-hydroxy function has been oxidised to an oxo group.


A 3beta-sterol formed formally by loss of a methyl group from the 14-position of lanosterol.


3-hydroxy-3-methylglutaryl-coenzyme A

An acyl-CoA oxoanion that results from the removal of all five protons from the phosphate and carboxylic acid groups of (3S)-3-hydroxy-3-methylglutaryl-CoA.


A 2,3-epoxysqualene in which the chiral centre has S configuration. It is converted into lanosterol by lanosterol synthase (EC 5.4.99.7) in a key rate-limiting step in the biosynthesis of chloesterol, steroid hormones, and vitamin D.


Lanosterol

A tetracyclic triterpenoid that is lanosta-8,24-diene substituted by a beta-hydroxy group at the 3beta position. It is the compound from which all steroids are derived.


Squalene

A triterpene consisting of 2,6,10,15,19,23-hexamethyltetracosane having six double bonds at the 2-, 6-, 10-, 14-, 18- and 22-positions with (all-E)-configuration.


Trianion of (R)-5-phosphomevalonic acid arising from deprotonation of the carboxy and phosphate OH groups; major species at pH 7.3.


A 3-oxoacyl-CoA(4-) arising from deprotonation of the phosphate and diphosphate OH groups of acetoacetyl-CoA.


ABCD4_HUMAN Lysosomal cobalamin transporter ABCD4 (sprot)

A lysosomal cobalamin transporter ABCD4 that is encoded in the genome of human.


EREG_HUMAN Proepiregulin (sprot)

A proepiregulin that is encoded in the genome of human.


G6PT1_HUMAN Glucose-6-phosphate exchanger SLC37A4 (sprot)

A glucose-6-phosphate exchanger SLC37A4 that is encoded in the genome of human.


CUBN_HUMAN Cubilin (sprot)

A cubilin that is encoded in the genome of human.


alpha-D-GALACTOSE

D-Galactopyranose having alpha-configuration at the anomeric centre.


5-Phosphoribosyl 1-pyrophosphate

Pentaanion of 5-O-phosphono-alpha-D-ribofuranosyl diphosphate arising from deprotonation of the phosphate and diphosphate OH groups; major species at pH 7.3.


Deoxyadenosine-triphosphate

A 2'-deoxyribonucleoside 5'-triphosphate(4-) that is the tetraanion of 2'-deoxyadenosine 5'-triphosphate (dATP), arising from deprotonation of the four triphosphate OH groups; major species at pH 7.3.


2-Amino-5-guanidinovaleric acid

The L-enantiomer of argininium(1+).


ZDHC9_HUMAN Palmitoyltransferase ZDHHC9 (sprot)

A palmitoyltransferase ZDHHC9 that is encoded in the genome of human.


CHST7_HUMAN Carbohydrate sulfotransferase 7 (sprot)

A carbohydrate sulfotransferase 7 that is encoded in the genome of human.


An NDP-alpha-D-glucose(2-) arising from deprotonation of the diphosphate OH groups of UDP-D-glucose; major species at pH 7.3.


UDP-N-acetyl-alpha-D-glucosamine

Dianion of UDP-N-acetyl-alpha-D-glucosamine arising from deprotonation of both free diphosphate OH groups; major species at pH 7.3.


HS3S5_HUMAN Heparan sulfate glucosamine 3-O-sulfotransferase 5 (sprot)

A heparan sulfate glucosamine 3-O-sulfotransferase 5 that is encoded in the genome of human.


B4GT1_HUMAN Beta-1,4-galactosyltransferase 1 (sprot)

A beta-1,4-galactosyltransferase 1 that is encoded in the genome of human.


B3GN7_HUMAN UDP-GlcNAc:betaGal beta-1,3-N-acetylglucosaminyltransferase 7 (sprot)

A UDP-GlcNAc:betaGal beta-1,3-N-acetylglucosaminyltransferase 7 that is encoded in the genome of human.


B4GA1_HUMAN Beta-1,4-glucuronyltransferase 1 (sprot)

A beta-1,4-glucuronyltransferase 1 that is encoded in the genome of human.


B3GN3_HUMAN N-acetyllactosaminide beta-1,3-N-acetylglucosaminyltransferase 3 (sprot)

An N-acetyllactosaminide beta-1,3-N-acetylglucosaminyltransferase 3 that is encoded in the genome of human.


B3GN4_HUMAN N-acetyllactosaminide beta-1,3-N-acetylglucosaminyltransferase 4 (sprot)

An N-acetyllactosaminide beta-1,3-N-acetylglucosaminyltransferase 4 that is encoded in the genome of human.


B3GN2_HUMAN N-acetyllactosaminide beta-1,3-N-acetylglucosaminyltransferase 2 (sprot)

An N-acetyllactosaminide beta-1,3-N-acetylglucosaminyltransferase 2 that is encoded in the genome of human.


CHST1_HUMAN Carbohydrate sulfotransferase 1 (sprot)

A carbohydrate sulfotransferase 1 that is encoded in the genome of human.


CHD1L_HUMAN Chromodomain-helicase-DNA-binding protein 1-like (sprot)

A chromodomain-helicase-DNA-binding protein 1-like that is encoded in the genome of human.


DLG4_HUMAN Disks large homolog 4 (sprot)

A disks large homolog 4 that is encoded in the genome of human.


glycine zwitterion

An amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of glycine.


fatty acid anion

The conjugate base of a fatty acid, arising from deprotonation of the carboxylic acid group of the corresponding fatty acid.


An amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of 5-hydroxy-L-tryptophan; major species at pH 7.3.


MUC2_HUMAN Mucin-2 (sprot)

A mucin-2 that is encoded in the genome of human.


TPSN_HUMAN Tapasin (sprot)

A tapasin that is encoded in the genome of human.


Chenodeoxycholate anion

Conjugate base of chenodeoxycholic acid; major species at pH 7.3.


Ascorbate

The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.


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


IFI27_HUMAN Interferon alpha-inducible protein 27, mitochondrial (sprot)

An interferon alpha-inducible protein 27 that is encoded in the genome of human.


MUC5B_HUMAN Mucin-5B (sprot)

A mucin-5B that is encoded in the genome of human.


VWF_HUMAN von Willebrand factor (sprot)

A von Willebrand factor that is encoded in the genome of human.


GBP2_HUMAN Guanylate-binding protein 2 (sprot)

A guanylate-binding protein 2 that is encoded in the genome of human.


GBP5_HUMAN Guanylate-binding protein 5 (sprot)

A guanylate-binding protein 5 that is encoded in the genome of human.


Sulfate

A sulfur oxoanion obtained by deprotonation of both OH groups of sulfuric acid.


alpha-aminoacyl-tRNA

Any ribonucleic acid that is transfer RNA in which one or more of the free OH groups carries an alpha-aminoacyl group.


TRNT1_HUMAN CCA tRNA nucleotidyltransferase 1, mitochondrial (sprot)

A CCA tRNA nucleotidyltransferase 1, mitochondrial that is encoded in the genome of human.


An organic anion that is the conjugate base of riboflavin resulting from the removal of a proton from the nitrogen at position 3 (between the two carbonyl groups). Major microspecies at pH 7.3.


Trianion of flavin adenine dinucleotide arising from deprotonation of the diphosphate OH groups and the imide nitrogen.


A16L1_HUMAN Autophagy-related protein 16-1 (sprot)

An autophagy-related protein 16-1 that is encoded in the genome of human.


The conjugate base of a 1-phosphatidyl-1D-myo-inositol; major species at pH 7.3.


ATG10_HUMAN Ubiquitin-like-conjugating enzyme ATG10 (sprot)

A ubiquitin-like-conjugating enzyme ATG10 that is encoded in the genome of human.


ATG12_HUMAN Ubiquitin-like protein ATG12 (sprot)

A ubiquitin-like protein ATG12 that is encoded in the genome of human.


ATG5_HUMAN Autophagy protein 5 (sprot)

An autophagy protein 5 that is encoded in the genome of human.


HLAA_HUMAN HLA class I histocompatibility antigen, A alpha chain (sprot)

An MHC class I histocompatibility antigen A alpha chain that is encoded in the genome of human.


PDIA3_HUMAN Protein disulfide-isomerase A3 (sprot)

A protein disulfide-isomerase A3 that is encoded in the genome of human.


ERAP1_HUMAN Endoplasmic reticulum aminopeptidase 1 (sprot)

An endoplasmic reticulum aminopeptidase 1 that is encoded in the genome of human.


CALR_HUMAN Calreticulin (sprot)

A calreticulin that is encoded in the genome of human.


B2MG_HUMAN Beta-2-microglobulin (sprot)

A beta-2-microglobulin that is encoded in the genome of human.


Pyridoxal 5'-phosphate(2-)

The dianion resulting from the removal of two protons from the phosphate group of pyridoxal 5'-phosphate.


Biotin

An organic heterobicyclic compound that consists of 2-oxohexahydro-1H-thieno[3,4-d]imidazole having a valeric acid substituent attached to the tetrahydrothiophene ring. The parent of the class of biotins.


Sodium ion

A monoatomic monocation obtained from sodium.


HDAC2_HUMAN Histone deacetylase 2 (sprot)

A histone deacetylase 2 that is encoded in the genome of human.


HDAC7_HUMAN Histone deacetylase 7 (sprot)

A histone deacetylase 7 that is encoded in the genome of human.


RFA1_HUMAN Replication protein A 70 kDa DNA-binding subunit (sprot)

A replication protein A 70 kDa DNA-binding subunit that is encoded in the genome of human.


Conjugate base of porphobilinogen arising from deprotonation of the two carboxy groups and protonation of the amino group; major species at pH 7.3.


The zwitterion formed from 5-aminolevulinic acid by transfer of a proton from the carboxy group to the amino group.  It is the major species present at physiological pH.


PROTOPORPHYRIN

A cyclic tetrapyrrole that consists of porphyrin bearing four methyl substituents at positions 3, 8, 13 and 17, two vinyl substituents at positions 7 and 12 and two 2-carboxyethyl substituents at positions 2 and 18. The parent of the class of protoporphyrins.


succinyl-CoA

An acyl-CoA oxoanion that is the pentaanion of succinyl-CoA, arising from deprotonation of the phosphate, diphosphate and carboxylic acid OH groups.


Ferroprotoporphyrin IX

Heme b in which the iron has oxidation state +2.


Octaanion of preuroporphyrinogen arising from global deprotonation of the eight carboxy groups; major species at pH 7.3.


Farnesyl diphosphate

The trans,trans-stereoisomer of farnesyl diphosphate.


An amino-acid betaine gamma-aminobutyric acid zwitterion in which all of the hydrogens attached to the nitrogen are replaced by methyl groups.


Major microspecies at pH 7.3.


Carnitine

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


BAX_HUMAN Apoptosis regulator BAX (sprot)

An apoptosis regulator BAX that is encoded in the genome of human.


RGS2_HUMAN Regulator of G-protein signaling 2 (sprot)

A regulator of G-protein signaling 2 that is encoded in the genome of human.


NADPH

The reduced form of NADP+; used in anabolic reactions, such as lipid and nucleic acid synthesis, which require NADPH as a reducing agent.


An endocannabinoid and an endogenous agonist of the cannabinoid receptors (CB1 and CB2). It is an ester formed from omega-6-arachidonic acid and glycerol.


dCTP tetraanion

A 2'-deoxyribonucleoside 5'-triphosphate(4-) arising from deprotonation of the triphosphate OH groups of 2'-deoxycytidine 5'-triphosphate (dCTP); major species at pH 7.3.


ADP-D-ribose

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


A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.


The conjugate base of a 1,2-diacyl-sn-glycero-3-phosphocholine compound formed by deprotonation of the phosphate OH group.


Acetaldehyde

The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.


Octaanion of 1D-myo-inositol 1,3,4,5-tetrakisphosphate arising from global deprotonation of the phosphate OH groups; major species at pH 7.3.


Ethanolamine

A member of the class of  ethanolamines that is ethane with an amino substituent at C-1 and a hydroxy substituent at C-2, making it both a primary amine and a primary alcohol.


Choline

A choline that is the parent compound of the cholines class, consisting of ethanolamine having three methyl substituents attached to the amino function.


Acetylcholine

Actylcholine is an ester of acetic acid and choline, which acts as a neurotransmitter.


Chloride ion

A halide anion formed when chlorine picks up an electron to form an an anion.


nucleoside 5'-triphoshate(4-)

A ribonucleoside triphosphate oxoanion arising from global deprotonation of the  triphosphate groups of any nucleoside triphosphate; major species at pH 7.3.


Deoxyguanosine-triphosphate

A 2'-deoxyribonucleoside 5'-triphosphate(4-) that is the tetraanion of 2'-deoxyguanosine 5'-triphosphate (dGTP), arising from deprotonation of the four triphosphate OH groups; major species at pH 7.3.


Deoxythymidine triphosphate

A 2'-deoxyribonucleoside 5'-triphosphate(4-) obtained by deprotonation of the four triphosphate OH groups of dTTP; major species at pH 7.3.


A 3-sn-glycerophosphoserine compound having acyl substituents at the 1- and 2-hydroxy positions.


1,2-diacyl-sn-glycerol 3-phosphate

An sn-glycerol 3-phosphate compound having unspecified O-acyl groups at the 1- and 2-positions.


Nitric Oxide

A nitrogen oxide which is a free radical, each molecule of which consists of one nitrogen and one oxygen atom.


Ferriheme

Heme b in which the iron has oxidation state +3.


Oxido nitrite

The nitrogen oxoanion formed by loss of a proton from peroxynitrous acid.


Zwitterionic form of L-citrulline having an anionic carboxy group and a protonated amino group; major species at pH 7.3.


Nitrite

The nitrogen oxoanion formed by loss of a proton from nitrous acid.


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


Bicarbonate

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


S-Adenosyl-L-methioninamine

Conjugate acid of S-adenosylmethioninamine arising from protonation of the primary amino group.


Zwitterionic form of L-methionine having a anionic carboxy group and a cationic amino group; major species at pH 7.3.


Formate

A monocarboxylic acid anion that is the conjugate base of formic acid. Induces severe metabolic acidosis and ocular injury in human subjects.


2-oxo monocarboxylic acid anion

An oxo monocarboxylic acid anion in which the oxo group is located at the 2-position.


Conjugate base of 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one arising from deprotonation of the 2-hydroxy group.


Spermine (fully protonated form)

An ammonium ion obtained by the protonation of all four amino groups of spermine.


Dianion of S-methyl-5-thio-D-ribulose 1-phosphate.


Dianion of S-methyl-5-thio-alpha-D-ribose 1-phosphate.


An ammonium ion that is the trication of spermidine, formed by protonation at all three nitrogens.


The 2-oxo monocarboxylic acid anion derived from 4-methylthio-2-oxobutanoic acid. The major microspecies at pH 7.3, it is formed from L-methionine via the action of methionine transaminase.


Dianion of 5-(methylsulfanyl)-2,3-dioxopentyl phosphate.


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


An alkane-alpha,omega-diammonium(2+) that is the dication of putrescine (1,4-butanediamine) arising from protonation of both primary amino groups; major species at pH 7.3.


threo-Ds-isocitrate

The D-threo-form of isocitrate(3-).


Zwitterionic form of gamma-aminobutyric acid having an anionic carboxy group and a protonated amino group.


The trianion of a 1-phosphatidyl-1D-myo-inositol 5-phosphate.


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


Zwitterionic form of L-alanine arising from transfer of a proton from the carboxy to the amino group; major species at pH 7.3.


lipid

'Lipids' is a loosely defined term for substances of biological origin that are soluble in nonpolar solvents. They consist of saponifiable lipids, such as glycerides (fats and oils) and phospholipids, as well as nonsaponifiable lipids, principally steroids.


long-chain fatty acid

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


electron

Elementary particle not affected by the strong force having a spin 1/2, a negative elementary charge and a rest mass of 0.000548579903(13) u, or 0.51099906(15) MeV.


Phenethylamine

A phenylethylamine having the phenyl substituent at the 2-position.


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


Tetrahydrobiopterin radical cation

An organic radical cation derived from 5,6,7,8-tetrahydrobiopterin.


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


Tetraanion of 7,8-dihydroneopterin 3'-triphosphate.


The conjugate base of monodehydro-L-ascorbic acid arising from deprotonation of the 4-hydroxy group; major species at pH 7.3.


Dyspropterin

A tetrahydropterin  that is 2-amino-5,6,7,8-tetrahydropteridin-4(3H)-one substituted by a 2-oxopropanoyl group at position 6.


A 7,8-dihydrobiopterin in which the 1,2-dihydroxypropyl group has (1S,2R)-configuration.


An sn-glycerophosphoserine compound having an acyl substituent at the 1-hydroxy position.


phosphatidylethanolamine zwitterion

The zwitterion of a phosphatidylethanolamine compound formed by proton transfer from the phosphate to the primary amino group.


d,l-Serine

A serine zwitterion obtained by transfer of a proton from the carboxy to the amino group of L-serine.


acyl-CoA

A thioester that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of any carboxylic acid.


1,3-Dihydroxypropan-2-yl formate

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


A 1-O-acylglycerophosphoethanolamine having (R)-configuration.


A lysophosphatidylethanolamine obtained by selective hydrolysis of the 1-acyl substituent of any 1,2-diacyl-sn-glycero-3-phosphoethanolamine.


N-arachidonoylphosphatidylethanolamine

An acyl derivative of phosphatidic acid whose phosphorus acid component is esterified with 2-N-arachidonoylaminoethanol.


Cytidine-monophosphate

A pyrimidine nucleoside 5'-monophosphate(2-) that results from the removal of two protons from the phosphate group of cytidine 5'-monophosphate; major species at pH 7.3.


The ammonium betaine of a 1-O-acyl-sn-glycero-3-phosphocholine arising from deprotonation of the phosphate OH; major species at pH 7.3.


N-acylphosphatidylethanolamine

A phosphatidylethanolamine in which the amine function has formed an amide with a fatty acid RCO2H.


Conjugate base of CDP-ethanolamine arising from deprotonation of the phosphate OH groups and protonation of the amino group; major species at pH 7.3.


acyl group

An organic group formed by removing one or more hydroxy groups from an oxoacid that has the general structure RkE(=O)l(OH)m (l =/= 0). Although the term is almost always applied to organic compounds, with carboxylic acid as the oxoacid, acyl groups can in principle be derived from other types of acids such as sulfonic acids or phosphonic acids.


Citicoline

A member of the class of  phosphocholines that is the chloine ester of CDP. It is an intermediate obtained in the biosynthetic pathway of structural phospholipids in cell membranes.


A 2-acylglycerophosphoinositol in which sn-glycerol, acylated at O(2), is linked through a phospho group at O(3) to O(1) of D-myo-inositol.


A 1-acylglycerophosphoinositol in which sn-glycerol, acylated at O(1), is linked through a phospho group at O(3) to O(1) of D-myo-inositol.


An organophosphate oxoanion arising from deprotonation of both phosphate OH groups of a CDP-diacylglycerol.


INOSITOL

An inositol having myo- configuration.


A phosphatidylglycerol consisting of cardiolipin lacking one fatty acyl group from the 2 or 2'-position.


cardiolipin

A phosphatidylglycerol composed of two molecules of phosphatidic acid covalently linked to a molecule of glycerol.


An anionic phospholipid obtained by deprotonation of both free phosphate OH groups of any 2,2'-dilysocardiolipin.


A phosphatidylglycerol(1-) in which the phosphatidyl moiety has R-configuration and the glycerol moiety has S-configuration.


An ionic phospholipid that is a dianion of a phosphatidic acid arising from deprotonation of both phosphate OH groups.


Trianion of 1-(3-sn-phosphatidyl)-sn-glycerol 3-phosphate arising from deprotonation of all three free phosphate OH groups; major species at pH 7.3.


A  2-acylglycerophosphocholine in which the glycerol moiety has sn stereochemistry and which has an unspecified acyl group attached at the 2-position.


A glycerophosphoglycerol in which sn-glycerol, acylated at O(1), is linked through a phospho group at O(3) to O(1) of glycerol.


A glycerophosphoglycerol in which sn-glycerol, acylated at O(2), is linked through a phospho group at O(3) to O(1) of glycerol.


Choline Alfoscerate

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


Sn-glycerol 3-phosphate(2-)

An organophosphate oxoanion that is the dianion of sn-glycerol 3-phosphate arising from deprotonation of both phosphate OH groups.


Major species at pH 7.3.


phospholipid

A lipid containing phosphoric acid as a mono- or di-ester. The term encompasses phosphatidic acids and phosphoglycerides.


The pentaanion of a 1-phosphatidyl-1D-myo-inositol 3,5-bisphosphate.


carboxylic acid

A carbon oxoacid acid carrying at least one -C(=O)OH group and having the structure RC(=O)OH, where R is any any monovalent functional group. Carboxylic acids are the most common type of organic acid.


phosphocholines

Any compound having phosphocholine as part of its structure.


2-Aminoethyl dihydrogen phosphate

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


fatty acyl-CoA(4-)

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


FADH2 dianion

The organophosphate oxoanion obtained by deprotonation of the diphosphate hydroxy groups of the reduced form of flavin adenine dinucleotide (FADH2).


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


A thiol that is the tautomer of mercaptopurine.


A primary alcohol that is the S-methyl derivative of mercaptoethanol. It is found as a volatile component in Cucumis melo Var. cantalupensis.


A macromolecule consisting of 5-methyltetrahydrofolic acid with an arbitrary number of glutamate residues attached as a polypeptide to the single existent one.


Pyridine

An  azaarene comprising a benzene core in which one -CH group is replaced by a nitrogen atom. It is the parent compound of the class pyridines.


A thiopurine that is 9H-purine substituted by a methylsulfanyl group at position 6.


A monohydroxybenzoate that is the conjugate base of 3-hydroxy-4-methoxybenzoic acid, arising from deprotonation of the carboxy group.


3,4-Dihydroxybenzoic acid

A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.


Glutathione disulfide dianion

A doubly-charged peptide anion arising from deprotonation of the four carboxy groups and protonation of the two amino groups of glutathione disulfide; major species at pH 7.3.


An ionic macromolecule consisting of (6R)-5,10-methylenetetrahydrofolate(2-) with an arbitrary number of glutamate residues attached as a polypeptide to the single existent one.


A nucleotide-sugar oxoanion that is a trianion arising from deprotonation of the carboxy and diphosphate OH groups of UDP-alpha-D-glucuronic acid; major species at pH 7.3.


A dicarboxylic acid dianion obtained by deprotonation of the two carboxy groups of bilirubin; major species at pH 7.3.


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


Salicylate

Any salt or ester arising from reaction of the carboxy group of salicylic acid, or any ester resulting from the condensation of the phenolic hydroxy group of salicylic acid with an organic acid.


Bis(beta-glucosyluronate)bilirubin

Conjugate base of bis(beta-glucosyluronic acid)bilirubin.


A N-substituted amine that is 4-aminobiphenyl substituted by a hydroxy group at the nitrogen atom.


Glutathione

A tripeptide compound consisting of glutamic acid attached via its side chain to the N-terminus of cysteinylglycine.


Ethylene Oxide

A  saturated organic heteromonocyclic parent that is a three-membered heterocycle of two carbon atoms and one oxygen atom.


Acetaminophen

A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.


Conjugate base of L-gamma-glutamyl-L-cysteine arising from deprotonation of both carboxy groups and protonation of the primary amino group; major species at pH 7.3.


A C-nitro compound that is chlorobenzene carrying a nitro substituent at each of the 2- and 4-positions.


An S-substituted glutathione(1-) obtained by deprotonation of the the two carboxy groups and protonation of the glutamyl amino group of S-(2,4-dinitrophenyl)glutathione. Major microspecies at pH 7.3.


Adenosine 3',5'-bismonophosphate(4-)

An organophosphate oxoanion arising from deprotonation of the phosphate OH groups of adenosine 3',5'-bismonophosphate; major species at pH 7.3.


3'-Phosphonato-5'-adenylyl sulfate(4-)

A quadruply-charged organophosphate oxoanion arising from deprotonation of the phosphate and sufate groups of 3'-phosphonato-5'-adenylyl sulfate; major species at pH 7.3.


Butyrate

A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.


Intropin

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


Phenol

An organic hydroxy compound that consists of benzene bearing a single hydroxy substituent. The parent of the class of phenols.


Menatetrenone Epoxide

A member of the class of tetralins obtained by formal epoxidation across the 2,3-double bond of menatetrenone.


Menatetrenone

A menaquinone whose side-chain contains 4 isoprene units in an all-trans-configuration.


2-Oxobutanoic acid

A 2-oxo monocarboxylic acid that is the 2-oxo derivative of butanoic acid.


L-cystathionine

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


Deoxycholic Acid

A bile acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 12 respectively.


dolichyl D-mannosyl phosphate anion

Conjugate base of dolichyl D-mannosyl phosphate arising from deprotonation of the free OH group of the phosphate.


Dolichyl phosphate dianion

Dianion of dolichyl phosphate arising from deprotonation of both phosphate OH groups.


Conjugate base of GDP-alpha-D-mannose arising from deprotonation of both free OH groups of the diphosphate.


3-Mercaptopyruvic acid

A 2-oxo monocarboxylic acid that is  pyruvic acid substituted by a sulfanyl group at position 3.


Sulfite

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


Coenzyme Q10

A ubiquinone having a side chain of 10 isoprenoid units. In the naturally occurring isomer, all isoprenyl double bonds are in the E- configuration.


(ethanolamineP) mannose (a1-2) (ethanolamineP) mannose (a1-6) (ethanolamineP) mannose (a1-4) glucosaminyl-acyl-PI

Is a glycan


An inositol compound having an alpha-mannosyl-(1->2)-alpha-mannosyl-(1->6)-alpha-2-(2-aminoethylphosphoryl)mannosyl-alpha-glucosaminyl moiety at the 6-position, a phosphatidyl substituent at the 1-position and an undefined acyl substituent in an unspecified position.


Betaine

The amino acid betaine derived from glycine.


(Dimethylammonio)acetate

An amino acid zwitterion resulting from transfer of a proton from the carboxy to the amino group of N,N-dimethylglycine; major species at pH 7.3.


Cysteine sulfinate

An alpha-amino-acid anion that is the conjugate base of 3-sulfino-L-alanine, arising from deprotonation of the sulfino and carboxy groups and protonation of the amino group; major species at pH 7.3.


The zwitterion formed from taurine by transfer of a proton from the sulfonyl to the amino group.  It is the major species existing at physiological pH.


Zwitterionic form of hypotaurine arising from migration of a proton from the sulfonate group to the amino group; major species at pH 7.3.


Thiocyanate

A pseudohalide anion obtained by deprotonation of the thiol group of thiocyanic acid.


Hydrogen Cyanide

A one-carbon compound consisting of a methine group triple bonded to a nitrogen atom


A 6-O-[alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl]-1-phosphatidyl-1D-myo-inositol compound having an undefined acyl substituent in an unspecified position on the inositol ring.


An inositol compound having an alpha-mannosyl-(1->6)-alpha-2-(2-aminoethylphosphoryl)mannosyl-alpha-glucosaminyl group at the 6-position, a phosphatidyl group at the 1-position and an undefined acyl substituent at an unspecified position.


A UDP-D-galactose(2-) in which the anomeric centre of the galactose moiety has alpha-configuration.


N-Acetyl-D-Galactosamine

The D-enantiomer of N-acetylgalactosamine.


A diosylceramide having beta-D-galactosyl-(1->4)-beta-D-glucose as the disaccharide component.


N-acylsphingosine 1-phosphate

A ceramide phosphate compound having the phosphate group in the 1-position and an unspecified acyl group atached to the nitrogen atom.


Dianion of UDP-N-acetyl-D-galactosamine arising from deprotonation of the diphosphate OH groups; major species at pH 7.3.


A glycotriaosylceramide having alpha-D-galactosyl-(1->4)-beta-D-galactosyl-(1->4)-beta-D-glucose as the trisaccharide component.


D-glucosyl-N-acylsphingosine

Sphingosine substituted at the 1-hydroxy group by a D-glucosyl group and at the 2-amino group by an acyl group.


The cationic sphingoid resulting from the protonation of the amino group of sphingosine.


N-acyl-beta-D-galactosylsphingosine

An N-acyl-D-galactosylsphingosine in which the anomeric configuration of the galactosyl residue is beta; sphingosine substituted at the O-1 position by a beta-D-galactosyl group and at the N-2 position by an acyl group.


A sialodiosylceramide consisting of the trisaccharide alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->4)-beta-D-Glc attached to the primary hydroxy function of ceramide.


N-Acetyl-Neuraminic Acid

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


An N-acetylneuraminate that is the conjugate base of beta-D-GalNAc-(1->4)-[alpha-Neu5Ac-(2->3)]-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-Cer, obtained by deprotonation of the carboxy group; major species at pH 7.3.


The conjugate base of sphingosine 1-phosphate having an anionic phosphate group and a protonated amino group; major species at pH 7.3.


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


D-glucopyranose 1-phosphate

An organophosphate oxoanion that is the dianion of D-glucopyranose 1-phosphate arising from deprotonation of both phosphate OH groups.


L-cysteinylglycine zwitterion

The zwitterion of L-cysteinylglycine resulting from the transfer of a proton from the hydroxy group of glycine to the amino group of cysteine. Major microspecies at pH 7.3.


Pyroglutamate

Conjugate base of 5-oxo-L-proline.


5'-Uridylic acid, disodium salt

A pyrimidine nucleoside 5'-monophosphate(2-) that results from the removal of two protons from the phosphate group of UMP.


Guanosine phosphate

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


Salicyluric acid

An N-acylglycine in which the acyl group is specified as 2-hydroxybenzoyl.


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


A hydroxyaldehyde consisting of phenylacetaldehyde having three hydroxy substituents located at the alpha-, 3- and 4-positions. It is a metabolite of noradrenaline.


An amino acid zwitterion obtained from the transfer of a proton from the carboxy group to the amino group of L-dopa. Major microspecies at pH 7.3.


The anion obtained from global deprotonation of the phosphate OH groups of myo-inositol 1,3,4,5,6-pentakisphosphate; major species at pH 7.3.


myo-inositol hexakisphosphate(12-)

The organophosphate oxoanion formed by loss of 2 protons from each of the phosphate groups of 1D-myo-inositol.


Fully deprotonated form of 5-diphospho-1D-myo-inositol pentakisphosphate.


Octaanion of 1D-myo-inositol 3,4,5,6-tetrakisphosphate arising from global deprotonation of the acidic phosphate OH groups.


1D-myo-inositol 1,3,4-trisphosphate(6-)

The hexaanion of 1D-myo-inositol 1,3,4-trisphosphate.


1D-myo-inositol 3,4,6-trisphosphate

A myo-inositol trisphosphate having the three phosphate groups at the 3-, 4-, and 6-positions.


Octaanion of myo-inositol 1,3,4,6-tetrakisphosphate arising from global deprotonation of the phosphate OH groups; major species at pH 7.3.


A myo-inositol tetrakisphosphate that consists of myo-inositol having the four phospho groups located at positions 2, 3, 4 and 6 as well as a diphospho group at position 5.


A 1D-myo-inositol bis(diphosphate) trisphosphate having the three phospho groups located at positions 3, 4 and 6 and the two diphospho groups at positions 1 and 5.


A myo-inositol pentakisphosphate that consists of myo-inositol having the five phospho groups located at positions 1, 2, 3, 4 and 6 as well as a triphospho group at position 5.


An inositol phosphate oxoanion obtained by global deprotonation of the phosphate and diphosphate OH groups of 1-diphospho-1D-myo-inositol 2,3,4,5,6-pentakisphosphate.


An organophosphate oxoanion obtained by deprotonation of all but one of the phosphate and diphosphate OH groups of 1,5-bis(diphospho)-1D-myo-inositol 2,3,4,6-tetrakisphosphate. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.).


A myo-inositol tetrakisphosphate that consists of myo-inositol having the four phospho groups located at positions 3, 4, 5 and 6 as well as a diphospho group at position 1.


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


alpha-Maltotriose

A maltotriose trisaccharide in which the glucose residue at the reducing end is in the pyranose ring form and has alpha configuration at the anomeric carbon atom..


D-(+)-Maltose

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


D-fructose

Fructose is a levorotatory monosaccharide and an isomer of glucose.  Although fructose is a hexose (6 carbon sugar), it generally exists as a 5-member hemiketal ring (a furanose).


Lactobiose

A glycosylglucose disaccharide, found most notably in milk, that consists of D-galactose and D-glucose fragments bonded through a beta-1->4 glycosidic linkage. The glucose fragment can be in either the alpha- or beta-pyranose form, whereas the galactose fragment can only have the beta-pyranose form.


chemical entity

A chemical entity is a physical entity of interest in chemistry including molecular entities, parts thereof, and chemical substances.


Dicarboxylate anion of biliverdin; major species at pH 7.3.


Carbon Monoxide

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


uroporphyrinogen I(8-)

The cyclic tetrapyrrole anion that is the octacarboxylate anion of uroporphyrinogen I.


coproporphyrinogen I(4-)

The cyclic tetrapyrrole anion formed by loss of a proton from each of the four carboxy groups of coproporphyrinogen I.


Guanosine diphosphate fucose

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


Dianion of CMP-N-acetyl-beta-neuraminate arising from deprotonation of carboxylic acid and phosphate functions; major species at pH 7.3.


Androstenedione

A 3-oxo Delta(4)-steroid that is androst-4-ene substituted by oxo groups at positions 3 and 17. It is a steroid hormone synthesized in the adrenal glands and gonads.


Testosterone

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


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


Desoxycortone

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


A 18-hydroxy steroid that is corticosterone substituted by a hydroxy group at position 18.


Aldosterone

A pregnane-based steroidal hormone produced by the outer-section (zona glomerulosa) of the adrenal cortex in the adrenal gland, and acts on the distal tubules and collecting ducts of the kidney to cause the conservation of sodium, secretion of potassium, increased water retention, and increased blood pressure. The overall effect of aldosterone is to increase reabsorption of ions and water in the kidney.


Corticosterone

A 21-hydroxy steroid that consists of pregn-4-ene substituted by hydroxy groups at positions 11 and 21 and oxo groups at positions 3 and 20. Corticosterone is a 21-carbon steroid hormone of the corticosteroid type produced in the cortex of the adrenal glands.


Hydrocortisone

A 17alpha-hydroxy-C21-steroid that is pregn-4-ene substituted by oxo groups at positions 3 and 20 and hydroxy groups at positions 11, 17 and 21. Cortisol is a corticosteroid hormone or glucocorticoid produced by zona fasciculata of the adrenal cortex, which is a part of the adrenal gland. It is usually referred to as the "stress hormone" as it is involved in response to stress and anxiety, controlled by corticotropin-releasing hormone (CRH). It increases blood pressure and blood sugar, and reduces immune responses.


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


Isopentenyl pyrophosphate

A prenol phosphate comprising 3-methylbut-3-en-1-ol having an O-diphosphate substituent.


Dimethylallyl diphosphate

A prenol phosphate that is a phosphoantigen comprising the O-pyrophosphate of prenol.


Geranyl diphosphate

The diphosphate of the polyprenol compound geraniol.


A steroid acid, the 4-carboxy-4-methyl derivative of zymosterol.


A steroid acid, the 4-carboxy derivative of zymosterol.


A 3beta-hydroxy steroid, the 4-methyl derivative of zymosterol.


Presqualene diphosphate

A triterpenyl phosphate that is presqualene in which the hydroxy hydrogen has been replaced by a diphosphate group.


A 3beta-sterol formed from lanosterol by reduction across the C-24-C-25 double bond.


The 5-diphospho derivative of (R)-mevalonic acid.


A cholestanoyl-CoA formed by thioester linkage between 3alpha,7alpha,24-trihydroxy-5beta-cholestanoic acid and coenzyme A.


An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (24R,25R)-3alpha,7alpha,12alpha,24-tetrahydroxy-5beta-cholestan-26-oic acid.


An organophosphate oxoanion that is the trianion of (R)-5-phosphopantothenic acid arising from deprotonation of the carboxy and phosphate OH groups; major species at pH 7.3


DL-Pantothenic acid

A member of the class of pantothenic acids that is an amide formed from pantoic acid and beta-alanine.


Trianion of N-[(R)-4-phosphopantothenoyl]-L-cysteine arising from deprotonation of carboxylic acid and phosphate functions.


dephospho-CoA

An adenosine 5'-phosphate that is coenzyme A in which the phosphate group at position 3' has been replaced by a hydrogen atom. It is an intermediate metabolite in pantothenate and CoA biosynthesis.


propionyl-CoA

An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of propionic acid.


A steroidal acyl-CoA(4-) resulting from the removal of all four protons from the phosphate groups of chenodeoxycholoyl-CoA. 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 3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-en-26-oic acid.


A cholestanoyl-CoA formed by thioester linkage between  3alpha,7alpha,12alpha-trihydroxy-24-oxo-5beta-cholestan-26-oic acid and coenzyme A.


A cholestanoyl-CoA formed by thioester linkage between 3alpha,7alpha-dihydroxy-24-oxo-5beta-cholestan-26-oic acid and coenzyme A.


An optically active form of lysinium having L-configuration.


Biocytin

A  monocarboxylic acid amide that results from the formal condensation of the carboxylic acid group of biotin with the N(6)-amino group of L-lysine.


Thiamine(1+) diphosphate(3-)

Dianion of thiamine(1+) diphosphate arising from deprotonation of the three OH groups of the diphosphate.


Thiamine triphosphate

A thiamine phosphate that is thiamine(1+) in which the hydroxy group is replaced by a triphosphate group. It is found in low amounts in most vertebrate tissues and can phosphorylate certain proteins.


L-dehydroascorbate

An organic anion and the conjugate base of L-dehydroascorbic acid, arising from deprotonation of the acidic C2-position.


The trianion arising from deprotonation of the diphosphate hydroxy groups and the imide nitrogen of flavin mononucleotide (FMN). Major species at pH 7.3.


Nicotinate mononucleotide

A D-ribonucleotide having nicotinic acid as the nucleobase.


Nicotinamide riboside

A pyridine nucleoside consisting of nicotinamide with a beta-D-ribofuranosyl moiety at the 1-position.


A dicarboxylic acid monoanion that is the conjugate base of 2-amino-3-(3-oxoprop-1-enyl)but-2-enedioic acid and the major microspecies at pH 7.3 (according to Marvin v 6.2.0.).


3-Hydroxyanthranilic acid

An  aminobenzoic acid that is benzoic acid substituted at C-2 by an amine group and at C-3 by a hydroxy group. It is an intermediate in the metabolism of the amino acid tryptophan.


A pyridinium ion comprising nicotinamide having a methyl group at the 1-position. It is a metabolite of nicotinamide which was initially considered to be biologically inactive but has emerged as an anti-thrombotic and anti-inflammatory agent.


(S)-Nadphx

A tetrahydronicotinamide adenine dinucleotide obtained by formal stereo- and regioselective hydration across the 2,3-double bond in the nicotinyl ring of NADPH, with the hydroxy group located at position 2, having (S)-configuration.


Dianion of 10-formyltetrahydrofolic acid arising from deprotonation of both carboxylic acid functions.


A tetrahydrofolyl glutamate consisting of a tetrahydrofolyl group linked via an amide bond to a poly(gamma-glutamyl chain)


Dianion of dihydrofolic acid arising from deprotonation of both carboxylic acid functions.


A derivative of folic acid in which the pteridine ring is fully reduced; it is the parent compound of a variety of coenzymes that serve as carriers of one-carbon groups in metabolic reactions.


Dianion of (6S)-5,6,7,8-tetrahydrofolic acid arising from deprotonation of both carboxylic acid functions.


A macromolecule consisting of 10-formyltetrahydrofolic acid with an arbitrary number of glutamate residues attached as a polypeptide to the single existent one.


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


A dicarboxylic acid anion arising from deprotonation of both carboxylic acid functions of (6R)-5,10-methenyltetrahydrofolic acid.


An ionic macromolecule consisting of (6R)-5,10-methenyltetrahydrofolate(2-) with an arbitrary number of glutamate residues attached as a polypeptide to the single existent one.


A linear trisaccharide glycosyl group consisting of two galactosyl residues linked to a xylosyl residue at the reducing end.


A linear hexasaccharide glycosyl group consisisting of one iduronic acid residue sulfated on O-2, one glucosamine residue sulfated on nitrogen and at O-3, one glucuronic acid residue, and two galactose residues linked to a xylosyl residue at the reducing end and which is commonly bonded to an amino acid residue.


An aspartate(1-) that is the  conjugate base of L-aspartic acid.


A linear heptasaccharide glycosyl group consisisting of one iduronic acid residue sulfated on O-2, two glucosamine residues, of which one is N-acetylated and the other is sulfated on nitrogen and at O-3, one glucuronic acid residue, and two galactose residues linked to a xylosyl residue at the reducing end and which is commonly bonded to an amino acid residue.


A linear tetrasaccharide glycosyl group consisting of one galacturonic acid resiue and two galactosyl residues linked to a xylosyl residue at the reducing end.


N-Acetylglucosamine

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


A linear pentasaccharide glycosyl group consisisting of one N-acetylglucosamine residue, one glucuronic acid residue and two galactose residues linked to a xylosyl residue at the reducing end and which is commonly bonded to an amino acid residue.


A linear hexasaccharide glycosyl group consisisting of one iduronic acid residue, one glucosamine residue sulfated on nitrogen and at O-3, one glucuronic acid residue, and two galactose residues linked to a xylosyl residue at the reducing end and which is commonly bonded to an amino acid residue.


A linear pentasaccharide glycosyl group consisisting of one glucosamine residue sulfated on nitrogen and at O-3, one glucuronic acid residue, and two galactose residues linked to a xylosyl residue at the reducing end and which is commonly bonded to an amino acid residue.


A linear heptasaccharide glycosyl group consisisting of one iduronic acid residue sulfated on O-2, two glucosamine residues, both sulfated on nitrogen and with one also sulfated at O-3 and the other sulfated at O-6, one glucuronic acid residue, and two galactose residues linked to a xylosyl residue at the reducing end and which is commonly bonded to an amino acid residue.


A linear heptasaccharide glycosyl group consisisting of one iduronic acid residue sulfated on O-2, two glucosamine residues, one of which is sulfated on nitrogen and at O-3, one glucuronic acid residue, and two galactose residues linked to a xylosyl residue at the reducing end and which is commonly bonded to an amino acid residue.


A linear pentasaccharide glycosyl group consisisting of one glucosamine residue, one glucuronic acid residue, and two galactose residues linked to a xylosyl residue at the reducing end and which is commonly bonded to an amino acid residue.


aldehydo-L-iduronate

An iduronate that is the conjugate base of aldehydo-L-iduronic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


A linear octasaccharide glycosyl group consisisting of two iduronic acid residues, one of which is sulfated on O-2, two glucosamine residues, both sulfated on nitrogen and with one also sulfated at O-3 and the other sulfated at O-6, one glucuronic acid residue, and two galactose residues linked to a xylosyl residue at the reducing end and which is commonly bonded to an amino acid residue.


D-glucuronic acid

The D-enantiomer of glucuronic acid.


An amino hexasaccharide comprising an iduronic acid residue, an acetylated galactosamine residue, sulfated on O-4, a glucuronic acid residue, and two galactose residues, linked to a xylose residue at the reducing end. It is an intermediate in the dermatan sulfate degradation pathway.


A linear heptasaccharide glycosyl group consisting of two N-acetylgalactosamine residues, two glucuronic acid residues and two galactosyl residues linked to a xylosyl residue at the reducing end.


A linear heptasaccharide glycosyl group consisting of two N-acetylgalactosamine residues (one of which is sulfated at the 4-position), one iduronic acid residue, one glucuronic acid residue and two galactosyl residues linked to a xylosyl residue at the reducing end.


A linear heptasaccharide glycosyl group consisting of two N-acetylgalactosamine residues (one of which is sulfated at the 4-position), one iduronic acid residue sulfated at the 2-position, one glucuronic acid residue and two galactosyl residues linked to a xylosyl residue at the reducing end.


An amino pentasaccharide comprising an N-acetylated galactosamine residue, sulfated on O-4, a glucuronic acid residue and two galactose residues, linked to a xylose residue at the reducing end. It is an intermediate in the chondroitin sulfate degradation pathway.


tetradecanoyl-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 myristic acid.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (7Z,10Z,13Z,16Z)-docosatetraenoic acid. It is a member of the n-6 PUFA and is the product of linoleic acid metabolism.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of all-cis-icosa-8,11,14-trienoic acid.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (6Z,9Z,12Z,15Z,18Z)-tetracosapentaenoic acid. It is a member of the n-6 PUFA and is the product of linoleic acid metabolism.


Osbond acid

The all-cis-isomer of a C22 polyunsaturated fatty acid having five double bonds in the 4-, 7-, 10-, 13- and 16-positions. It is a member of n-6 PUFA and a product of linoleic acid metabolism.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (9Z,12Z,15Z,18Z)-tetracosatetraenoic acid. It is a member of the n-6 PUFA and is the product of linoleic acid metabolism.


gamma-Linolenoyl-CoA

An octadecatrienoyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of gamma-linolenic acid.


An acyl-CoA(4-) arising from deprotonation of the phosphate and diphosphate functions of arachidonoyl-CoA.


linoleoyl-CoA

An octadecadienoyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of linoleic acid.


Linoleic Acid

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


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (9Z,12Z,15Z,18Z,21Z)-tetracosapentaenoic acid. It is a member of the n-3 PUFA and is the product of alpha-linolenic acid metabolism.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosahexaenoic acid. It is a member of n-3 PUFA and a product of alpha-linolenoic acid metabolism.


alpha-Linolenoyl-CoA

An octadecatrienoyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of alpha-linolenic acid.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid. It is a member of n-3 PUFA and a product of alpha-linolenic acid metabolism


Stearidonoyl-CoA

An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (6Z,9Z,12Z,15Z)-octadecatetraenoic acid. It is a member of the n-3 PUFA and is the product of alpha-linolenic acid metabolism.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (8Z,11Z,14Z,17Z)-icosatetraenoic acid. It is a member of the n-3 PUFA and is the product of alpha-linolenic acid metabolism.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (6Z,9Z,12Z,15Z,18Z,21Z)-3-hydroxytetracosahexaenoic acid. It is a member of n-3 PUFA and a product of alpha-linolenoic acid metabolism.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (5Z,8Z,11Z,14Z,17Z)-icosapentaenoic acid. It is a member of n-3 PUFA and by-product of alpha-linolenic acid metabolism.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (2E,6Z,9Z,12Z,15Z,18Z,21Z)-tetracosaheptaenoic acid. It is a member of n-3 PUFA and a product of alpha-linolenoic acid metabolism.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (6Z,9Z,12Z,15Z,18Z,21Z)-3-oxotetracosahexaenoic acid. It is a member of n-3 PUFA and a product of alpha-linolenoic acid metabolism.


A polyunsaturated fatty acid anion that is the conjugate base of (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoic acid. It is a member of n-3 PUFA and a product of alpha-linolenoic acid metabolism.


Linolenic Acid

A linolenic acid with cis-double bonds at positions 9, 12 and 15. Shown to have an antithrombotic effect.


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


A tetrahydropterin that is 5,6,7,8-tetrahydrobiopterin carrying an additional hydroxy substituent at the 4a-position.


Melatonin

A member of the class of  acetamides that is acetamide in which one of the hydrogens attached to the nitrogen atom is replaced by a 2-(5-methoxy-1H-indol-3-yl)ethyl group. It is a hormone secreted by the pineal gland in humans.


An N-acylserotonin resulting from the formal condensation of the primary amino group of serotonin with the carboxy group of acetic acid.


The monoiodotyrosine that is L-tyrosine carrying an iodo-substituent at position C-3 of the benzyl group.


An alpha-amino-acid anion that is the conjugate base of 3,5-diiodo-L-tyrosine.


Hydriodic acid

A diatomic molecule containing covalently bonded hydrogen and iodine atoms.


Levothyroxine

The L-enantiomer of thyroxine.


Iodine

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


4-Hydroxyretinoic acid

A retinoid that consists of all-trans-retinoic acid bearing a hydroxy substituent at position 4 on the cyclohexenyl ring.


Tretinoin

A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.


Lauric Acid

A straight-chain, twelve-carbon medium-chain saturated fatty acid with strong bactericidal properties; the main fatty acid in coconut oil and palm kernel oil.


19-Hydroxyarachidonic acid

A HETE that consists of arachidonic acid bearing a hydroxy substituent at position 19.


A hydroxy monocarboxylic acid consisting of icosa-5,9,14-trienoic acid having three hydroxy groups placed at the 8-, 11- and 12-positions.


20-Hydroxy-leukotriene B4

The 20-hydroxy derivative of leukotriene B4.


Leukotriene B4

A leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway.


Leukotriene A4

A leukotriene that is the (5S,6S)-epoxy derivative of (7E,9E,11Z,14Z)-icosa-7,9,11,14-tetraenoic acid.


thromboxane A2

A thromboxane which is produced by activated platelets and has prothrombotic properties: it stimulates activation of new platelets as well as increases platelet aggregation.


Histaminium

An ammonium ion that is the conjugate acid of histamine protonated on the side-chain nitrogen.


Methanol

The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.


An icosatetraenoic acid in which the double bonds are located at the 6-7, 8-9, 11-12, and 14-15 positions and have E, Z, Z, and Z geometry, respectively, and in which the pro-S hydrogen is substituted by a hydroperoxy group.


An oxoicosatetraenoic acid having a 5-oxo group; and (6E)-, (8Z), (11Z)- and (14Z)-double bonds.


A HETE having a (5S)-hydroxy group and (6E)-, (8Z)-, (11Z)- and (14Z)-double bonds.


The (S)-enantiomer of 15-HPETE.


An oxoicosatetraenoic acid having (5Z,8Z,11Z,13E) double bond stereochemistry, and an oxo group in position 15.


Icomucret

An optically active form of 15-HETE having 15(S)-configuration..


An optically active form of 15-HETE having 15(R)-configuration.


A HPETE that is (5Z,8Z,10E,12R,14Z)-icosa-5,8,10,14-tetraenoic acid with the hydroperoxy group located at position 12 (the R-enantiomer).


The (S)-enantiomer of 12-HPETE.


A HETE having a (12R)-hydroxy group and (5Z)-, (8Z)-, (10E)- and (14Z)-double bonds.


A HETE having a (12S)-hydroxy group and (5Z)-, (8Z)-, (10E)- and (14Z)-double bonds.


hepoxilin A3

A hepoxilin having (5Z,9E,14Z) double bond stereochemistry, an 8-hydroxy substituent and an 11S,12S-epoxy group.


20-Hydroxyeicosatetraenoic acid

A HETE that consists of arachidonic acid bearing a hydroxy substituent at position 20.


Einecs 307-780-4

An amino disaccharide consisting of N-acetyl-D-glucosamine having a beta-D-glucuronosyl residue attached at the 3-position.


A C20 hydroxy fatty acid obtained by formal hydrogenation across the 13,-14-double bond of 15-oxolipoxin A4.


lipoxin A4

A C20 hydroxy fatty acid having (5S)-, (6R)- and (15S)-hydroxy groups as well as (7E)- (9E)-, (11Z)- and (13E)-double bonds.


A C20 hydroxy fatty acid having (5S)- and (6R)- -hydroxy groups as well as a 15-oxo group and (7E)- (9E)-, (11Z)- and (13E)-double bonds.


A 3-demethylubiquinol in which the polyprenyl chain contains 10 prenyl units.


A polyprenylhydroquinone in which the polyprenyl substituent is decaprenyl at C-2; additional methyl and methoxy groups are also present at positions C-3 and C-6 respectively.


A monohydroxybenzoic acid that is 4-hydroxybenzoic acid in which the hydrogens at positions 3 and 5 are substituted by a methoxy and a decaprenyl group.


A polyprenylhydroquinone in which the polyprenyl substituent is decaprenyl at C-2; a methoxy group is also present at C-6.


Ubiquinol

A ubiquinol in which the polyprenyl substituent is decaprenyl.


3-Decaprenyl-4,5-dihydroxybenzoic acid

A dihydroxybenzoic acid that is 3,4-dihydroxybenzoic acid in which the hydrogen at position 5 is substituted by a decaprenyl group.


4-Hydroxybenzoic acid

A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.


A monohydroxybenzoic acid that is 4-hydroxybenzoic acid in which the hydrogen at position 3 is substituted by a decaprenyl group.


All-trans-decaprenyl diphosphate

A decaprenyl diphosphate having (E)-stereochemistry exclusively in the double bonds.


leukotriene D4

A leukotriene that is (7E,9E,11Z,14Z)-icosa-7,9,11,14-tetraenoic acid substituted by a hydroxy group at position 5 (5S) and a L-cysteinylglycinyl group at position 6 (6R).


A long-chain fatty acid consisting of leukotriene B4 having a 12-keto group in place of the 12-hydroxy group.


A leukotriene that is the 14R-(S-glutathionyl),15S-hydroxy derivative of (5Z,8Z,10E,12E)-icosa-7,9,11,14-tetraenoic acid.


14,15-Leukotriene E4

A leukotriene that is the 14R-(S-cysteinyl),15S-hydroxy derivative of (5Z,8Z,10E,12E)-icosa-7,9,11,14-tetraenoic acid.


Eoxin A4

An oxylipin that is the (14S,15S)-epoxy derivative of (5Z,8Z,10E,12E)-icosa-5,8,10,12-tetraenoic acid.


leukotriene C4

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


20-Carboxy-leukotriene B4

A member of the class of leukotrienes that is leukotriene B4 in which the terminal methyl group has undergone formal oxidation to the corresponding carboxylic acid.


leukotriene E4

A leukotriene that is (7E,9E,11Z,14Z)-icosa-7,9,11,14-tetraenoic acid substituted by a hydroxy group at position 5 (5S) and an L-cystein-S-yl group at position 6 (6R).


14,15-Leukotriene D4

A leukotriene that is the 14R-(S-cysteinylglycyl),15S-hydroxy derivative of (5Z,8Z,10E,12E)-icosa-7,9,11,14-tetraenoic acid.


An octadecatetraenedioic acid obtained by oxidative degradation of leukotriene B4, a process that results in the removal of C19 and C20 with concomitant dioxygenation of C18.


A leukotriene that is leukotriene B4 bearing an additional oxo substituent at position 20.


IMP dianion

A nucleoside 5'-monophosphate(2-) that results from the removal of two protons from the phosphate group of IMP; major species at pH 7.3.


delta-12-Prostaglandin J2

A member of the class of prostaglandins J that is prosta-5,9,12-trien-1-oic acid carrying oxo and hydsroxy substituents at positions 11 and 15 respectively (the 5Z,12E,15S-stereoisomer).


Prostaglandin C2

A member of the class of prostaglandins C that is prosta-5,11,13-trien-1-oic acid carrying oxo and hydroxy substituents at positions 9 and 15 respectively (the 5Z,13E,15S-stereoisomer).


11-epi-Prostaglandin F2alpha

The prostaglandin F that is the 11-epimer of prostaglandin F2alpha.


15-deoxy-Delta(12,14)-prostaglandin D2

A prostaglandin D derivative that is prostaglandin D2 lacking the 15-hydroxy group and having C=C double bonds at positions 12(13) and 14(15).


thromboxane B2

A member of the class of thromboxanes B that is (5Z,13E)-thromboxa-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15.


15d-Prostaglandin A2

A prostaglandin A derivative that is prostaglandin A2 lacking the 15-hydroxy group and having C=C double bonds at positions 12(13) and 14(15).


6-Keto-prostaglandin F1alpha

A prostaglandin Falpha that is prostaglandin F1alpha bearing a keto substituent at the 6-position.


prostaglandin D2

A member of the class of  prostaglandins D that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9 and 15 and an oxo group at position 11 (the 5Z,9alpha,13E,15S- stereoisomer).


Malonaldehyde

A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.


12-Hydroxyheptadecatrienoic acid

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


11-Dehydro-thromboxane B2

A thromboxane obtained by formal oxidation of the hemiacetal hydroxy function of thromboxane B2.


prostaglandin J2

A member of the class of prostaglandins J that consists of prosta-5,9,13-trien-1-oic acid substituted by an oxo group at position 11 and a hydroxy group at position 15 (the 5Z,13E,15S stereoisomer).


Dinoprost

A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.


thioredoxin disulfide

A protein disulfide that is the oxidised form of a thioredoxin, in which two cysteine residues are joined by formation of a disulfide bridge.


15-Deoxy-delta-12,14-prostaglandin J2

A prostaglandin J derivative comprising prostaglandin J2 lacking the 15-hydroxy group and having C=C double bonds at the 12- and 14-positions.


A glutathione conjugate obtained by formation of a thioselenide link between the thiol group of glutathione and the selenol group of 1-seleno-N-acetyl-D-galactosamine.


Methylselenium(II)

An organoselenium compound that is a selenium analogue of methanol, comprising a methyl group covalently bound to a selenol group.


A glycal derivative that is 1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol substituted by an acetylamino group at position 2.


selenosugar B

A monosaccharide derivative that is  N-acetyl-beta-D-galactosamine in which the anomeric hydroxy group is replaced by a methylseleno group.


Methylselenic acid

An organoselenium compound that is seleninic acid in which the hydrogen attached to selenium is replaced by a methyl group.


A carboxylic acid anion resulting from the deprotonation of all four carboxy groups and the protonation of both of the primary amino groups of selenodiglutathione. The major species at pH 7.3.


N-acetyl-beta-D-galactosaminyl group

The glycosyl group obtained by removing the hydroxy group from the hemiacetal function of N-acetyl-beta-D-galactosamine.


H-gGlu-Cys(SeH)-Gly-OH

A glutathione derivative that is glutathione in which the hydrogen attached to the sulfur is replaced by a selenol group.


beta-N-ACETYL-D-GALACTOSAMINE

An N-acetyl-D-galactosamine having beta-configuration at the anomeric centre.


A retinal having 2E,4Z,6E,8E-double bond geometry.


Retinal

A retinal in which all four exocyclic double bonds have E- (trans-) geometry.


photon

Particle of zero charge, zero rest mass, spin quantum number 1, energy hnu and momentum hnu/c (h is the Planck constant, nu the frequency of radiation and c the speed of light), carrier of electromagnetic force.


Riboxin

A nucleoside 5'-diphosphate(3-) arising from deprotonation of all three OH groups of the diphosphate function of of inosine 5'-diphosphate (IDP); major species at pH 7.3.


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


Major microspecies at pH 7.3


L-selenohomocysteine

A selenoamino acid that is the selenium analogue of L-homocysteine.


L-adenosylselenomethionine

A selenomethionine consisting of L-selenomethionine having an adenosyl group attached to the selenium.


Se-Adenosylselenohomocysteine

A selenoamino acid that is L-selenomethionine in which the methyl group attached to the selenium is replaced by a 5'-adenosyl group.


Methaneselenenic acid

An organoselenium compound comprising a methyl and hydroxy group covalently bound to a selenium atom.


L-Selenocystathionine

An optically active form of selenocystathionine in which both amino acid residues have L-configuration.


Selenocysteine

The L-enantiomer of selenocysteine.


Trimethylselenonium

An organic cation consisting of three methyl groups covalently bound to a central selenium atom.


Dimethyl selenide

An organoselenium compound of two methyl groups covalently bound to a selenium.


A trivalent inorganic anion obtained by removal of all three protons from selenophosphoric acid.


Cyclic GMP

A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.


Uric Acid

An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.


dCMP dianion

A 2'-deoxyribonucleoside 5'-monophosphate(2-) obtained by deprotonation of the phosphate OH groups of 2'-deoxycytidine 5'-monophosphate (dCMP); major species at pH 7.3.


Thymidine 5'-monophosphate

A 2'-deoxyribonucleoside 5'-monophosphate(2-) obtained by deprotonation of the phosphate OH groups of dTMP; major species at pH 7.3.


L-Lactic acid

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


Urea

A carbonyl group with two C-bound amine groups. The commercially available fertilizer has an analysis of 46-0-0 (N-P2O5-K2O).


D-Glucono-1,5-lactone 6-phosphate

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


Glyoxylic acid

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


An organophosphate oxoanion that is a trianion arising from deprotonation of phosphate and carboxylic acid functions of 6-phospho-D-gluconic acid.


Xanthine

An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated.


An organophosphate oxoanion that is the dianion resulting from the removal of two protons from the phosphate group of D-ribulose 5-phosphate.


Oxalic Acid

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


Glycolate

A hydroxy monocarboxylic acid anion that is acetate where the methyl group has been hydroxylated.


L-ornithinium

A polar amino acid zwitterion of L-ornithine.


The zwitterion formed from L-proline by proton transfer from the carboxy group to the ring nitrogen. It is the predominant species at physiological pH.


Platelet activating factor-acether

A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has octadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.


Kynurenic acid

A quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by a hydroxy group at C-4.


Homovanillic Acid

A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.


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


A nucleoside 5'-monophosphate(2-) that results from the removal of two protons from the phosphate group of 5'-xanthylic acid; major species at pH 7.3.


Conjugate base of (N(omega)-L-arginino)succinic acid.


Conjugate base of 5-phospho-beta-D-ribosylamine.


Orotidine 5'-phosphate(3-)

Trianion of orotidine 5'-phosphate arising from deprotonation of carboxylic acid and phosphate functions.


organic anion

Any organic ion with a net negative charge.


The S-phytanoyl derivative of coenzyme A.


pristanoyl-CoA

A multi-methyl-branched fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of pristanic acid.


A multi-methyl-branched fatty acyl-CoA having 2-hydroxyphytanoyl as the S-acyl group.


Pristanate

A methyl-branched fatty acid anion that is the conjugate base of pristanic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


formyl-CoA

An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of formic acid.


4,8 Dimethylnonanoyl carnitine

An O-acylcarnitine compound having 4,8-dimethylnonanoyl as the acyl substituent.


A multi-methyl-branched fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-oxopristanic acid.


A 3-oxo-fatty acyl-CoA(4-) arising from deprotonation of the phosphate and diphosphate functions of 3-oxohexacosanoyl-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 (E)-2,3-didehydropristanic acid.


A medium-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 4,8-dimethylnonanoic acid.


A multi-methyl-branched fatty acyl-CoA that is the S-(4,8,12-trimethyltridecanoyl) derivative of coenzyme A.


Propionylcarnitine

An O-acylcarnitine compound having propanoyl as the acyl substituent.


A saturated fatty acyl-CoA(4-) oxoanion arising from deprotonation of the phosphate and diphosphate OH groups of tetracosanoyl-CoA. The major species at pH 7.3.


A multi-methyl-branched fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-hydroxypristanic acid.


octanoyl-coenzyme A

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


4-Hydroxyglutamate semialdehyde

The L-alpha-amino acid zwitterion formed from L-4-hydroxyglutamic semialdehyde by transfer of a proton from the carboxy to the amine group; it is the principal microspecies at pH 7.3.


An oxo dicarboxylate obtained by deprotonation of both carboxy groups of 4-hydroxy-2-oxoglutaric acid.


An L-alpha-amino acid anion resulting from deprotonation of the carboxy groups and protonation of the amino group of 4-hydroxy-L-glutamic acid


Conjugate base of 1-pyrroline-3-hydroxy-5-carboxylic acid.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of trans-2-hexacosenoic acid.


hexacosanoyl-CoA

A very long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of hexacosanoic (cerotic) acid..


A 3-hydroxy fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-hydroxyhexacosanoic acid.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of trans-oct-2-enoic acid.


An N-acetyl-D-galactosaminyl group in which a sialic acid residue (Neu5Ac) is linked alpha(2->6) to the D-GalNAc group which has alpha-configuration at its anomeric centre.


An aldehydo-N-acyl-D-mannosamine 6-phosphate that has acetyl as the acyl group.


A galactosyl group derived from the disaccharide alpha-N-acetylneuraminyl-(2->6)-D-galactose.


N-acetyl-D-galactosaminyl group

A galactosaminyl group (D-configuration) in which the amino group at C-2 is acetylated. The group may be substituted with further mono- or oligo-saccharide groups.


N-acetylneuraminyl group

A sialosyl group derived from N-acetylneuraminic acid.


alpha-D-galactosyl group

A galactosyl group obtained by removing the hydroxy group from the hemiacetal function of alpha-D-galactose and, by extension, of a lower oligosaccharide having alpha-D-galactose at the reducing end. The unsubstituted parent of the class of alpha-D-galactosyl groups.


A galactosyl group derived from the disaccharide alpha-N-acetylneuraminyl-(2->3)-D-galactose. Implied reactive epitope within gangliosides LM1, GD1a and GT1b.


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


A sialosyl group derived from the disaccharide alpha-N-acetylneuraminyl-(2->8)-alpha-N-acetylneuraminic acid.


Octanoic acid

A straight-chain saturated fatty acid that is heptane in which one of the hydrogens of a terminal methyl group has been replaced by a carboxy group. Octanoic acid is also known as caprylic acid.


Capric Acid

A C10, straight-chain saturated fatty acid.


A positively charged methylguanosine in which a single methyl substituent is located at position 7.


A dolichyl diphosphooligosaccharide compound consisting of a branched tetradecasaccharide attached to the dolichyl chain via a diphosphate linkage.


Any one of a group of prenol derivatives made up of varying numbers of cis-linked isoprene units, terminating in an alpha-saturated isoprenoid group containing an alcohol functional group, with the three isoprene units at the distal end trans-linked.


CDP trianion

A nucleoside 5'-diphosphate(3-) arising from deprotonation of the three triphosphate OH groups of cytidine 5'-diphosphate (CDP); major species at pH 7.3.


Glucosamine 6-phosphate

A 2-amino-2-deoxy-D-glucopyranose 6-phosphate that has an alpha-configuration at the anomeric position.


N-acetyl-D-glucosamine 6-phosphate(2-)

Dianion of N-acetyl-D-glucosamine 6-phosphate arising from deprotonation of both OH groups of the phosphate.


Dianion of N-acetyl-alpha-D-glucosamine 1-phosphate arising from deprotonation of the phosphate OH groups; major species at pH 7.3.


N-glycoloyl-D-glucosamine 6-phosphate

An N-acyl-D-glucosamine phosphate in which the N-acyl group is specified as glycoloyl and the phosphate group is located at position 6. An intermediate in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway


An alpha-D-Man-(1->2)-alpha-D-Man-(1->2)-alpha-D-Man-(1->3)-[alpha-D-Man-(1->2)-alpha-D-Man-(1->3)-[alpha-D-Man-(1->2)-alpha-D-Man-(1->6)]-alpha-D-Man-(1->6)]-beta-D-Man-(1->4)-beta-D-GlcNAc-(1->4)-D-GlcNAc(PP-Dol) in which the anomeric centre has alpha-configuration.


A dolichyl diphosphooligosaccharide compound consisting of a branched pentasaccharide attached to the dolichyl chain via a diphosphate linkage.


A dolichyl diphosphooligosaccharide intermediate involved in post-translational modification of proteins.


dolichyl beta-D-glucosyl phosphate

A polyprenyl glycosyl phosphate having dolichyl as the polyprenyl component and beta-D-glucose as the glycosyl component.


A dolichyl diphosphooligosaccharide compound consisting of a branched octasaccharide attached to the dolichyl chain via a diphosphate linkage.


A dolichyl diphosphooligosaccharide compound consisting of a branched tridecasaccharide attached to the dolichyl chain via a diphosphate linkage.


diacetylchitobiosyldiphosphodolichol

A chitobiosyldiphosphodolichol compound having two acetyl substituents in unspecified positions.


A dihydroorotate that is the conjugate base of (S)-dihydroorotic acid.


Carbamoyl phosphate(2-)

A doubly-charged organophosphate oxoanion arising from deprotonation of the phosphate OH groups of carbamoyl phosphate; major species at pH 7.3.


L-Ureidosuccinate

An N-carbamoyl-L-alpha-amino acid anion obtained by deprotonation of the carboxy groups of N-carbamoyl-L-aspartic acid.


A nucleobase analogue that is cytosine in which the hydrogen at position 5 is replaced by a formyl group.


Cytosine-5-carboxylic acid

A nucleobase analogue that is cytosine in which the hydrogen at position 5 is replaced by a carboxy group.


Phosphate ion

A phosphate ion that is the conjugate base of hydrogenphosphate.


nucleoside 5'-diphosphate(3-)

Trianion of nucleoside diphosphate arising from deprotonation of all three free OH groups of the diphosphate; major species at pH 7.3.


Deoxyuridine-phosphate

A 2'-deoxyribonucleoside 5'-monophosphate(2-) obtained by deprotonation of the phosphate OH groups of 2'-deoxyuridine 5'-monophosphate (dUMP); major species at pH 7.3.


An organophosphate oxoanion formed by deprotonation of the diphosphate OH groups of any 2'-deoxynucleoside 5'-diphosphate.


Tetraanion of N(6)-(1,2-dicarboxyethyl)-AMP arising from deprotonation of carboxylic acid and phosphate functions.


XYLITOL

A pentitol (five-carbon sugar alcohol) having meso-configuration, being derived from xylose by reduction of the carbonyl group.


The conjugate base of 3-dehydro-L-gulonic acid; major species at pH 7.3.


D-xylulose

The D-enantiomer of xylulose.


Leucodopachrome

Indoline substituted with hydroxy groups at C-5 and -6 and a carboxy group at C-2, and with S stereochemistry at C-2.


5,6-Indolequinone-2-carboxylic acid

An indoledione that is 1H-indole-5,6-dione substituted by a carboxy group at position 2.


Dopaquinone

An L-phenylalanine derivative in which the phenyl group of L-phenylalanine is replaced by a 3,4-dioxocyclohexa-1,5-dien-1-yl group.


Decanoyl-coa

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


Fumaric Acid

A butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle.


cis-4-Decenoyl-coenzyme A

An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of cis-dec-4-enoic acid.


An acyl-CoA(4-) oxoanion arising from deprotonation of the phosphate and diphosphate OH groups of hexanoyl-CoA; major species at pH 7.3.


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


butanoyl-CoA

An acyl-CoA(4-) that is the tetraanion of butyryl-CoA, arising from deprotonation of phosphate and diphosphate functions.


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


A hexadecenoyl-CoA(4-) obtained by deprotonation of the phosphate and diphosphate OH groups of (E)-hexadec-2-enoyl-CoA; major species at pH 7.3.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of trans-dec-2-enoic acid.


The S-(3-oxopalmitoyl) derivative of coenzyme A.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (2-trans,6-cis)-dodeca-2,6-dienoic acid.


Tetraanion of trans-dodec-2-enoyl-CoA arising from deprotonation of phosphate and diphosphate functions.


A hydroxy fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (S)-3-hydroxyhexanoyl-CoA.


An oxo-fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxylic acid group of 3-oxooctanoic acid.


An oxo-fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxylic acid group of 3-oxolauroic acid.


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


An oxo-fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxylic acid group of 3-oxodecanoic acid.


An acyl-CoA(4-) arising from deprotonation of phosphate and diphosphate functions of lauroyl-CoA; 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 (S)-3-hydroxydodecanoic acid.


An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (2-trans,4-cis)-deca-2,4-dienoic acid.


An acyl-CoA(4-) arising from deprotonation of the phosphate and diphosphate OH groups of trans-hex-2-enoyl-CoA; major species at pH 7.3.


An oxo-fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxylic acid group of 3-oxohexanoic acid.


Tetraanion of crotonoyl-CoA arising from deprotonation of phosphate and diphosphate functions.


A hydroxy fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (S)-3-hydroxyoctanoic acid.


An L-alpha-amino acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of L-2-amino-3-oxobutanoic acid. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.).


Guanine

A 2-aminopurine carrying a 6-oxo substituent.


beta-L-fucose 1-phosphate

The beta-anomer of L-fucose 1-phosphate.


A GDP-4-dehydro-L-fucose in which the anomeric centre of the fucose portion has beta-configuration. An intermediate formed during the de novo synthesis of GDP-L-fucose.


beta-L-Fucose

A L-fucopyranose with a beta-configuration at the anomeric position.


semiquinone

An organic radical resulting from the formal addition of one hydrogen atom with its electron to a quinone (or from the formal removal of one hydrogen atom with its electron from the corresponding hydroquinone).


The parent structure of the family of 1,2-naphthoquinones, in which the oxo groups of the quinone moiety are at positions 1 and 2 of the naphthalene ring. It is a metabolite of naphthalene and is found in diesel exhaust particles.


D-glyceraldehyde

The D-enantiomer of glyceraldehyde.


alpha-D-Glucose 1,6-bisphosphate

A D-glucose 1,6-bisphosphate in which both phosphate groups are monophosphates.


The open chain form of D-fructose 1-phosphate.


alpha-D-Galactose 1-phosphate

A D-galactopyranose 1-phosphate having alpha-configuration at the anomeric centre.


(2R)-2,3-Dihydroxypropanoic acid

The D-enantiomer of glyceric acid.


Zwitterionic form of homocysteine arising from transfer of a proton from the carboxy to the amino group; major species at pH 7.3.


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


Zwitterionic form of beta-alanine arising from transfer of a proton from the carboxy to the amino group; major species at pH 7.3.


A monocarboxylic acid anion that is the conjugate base of N-carbamoyl-beta-alanine arising from deprotonation of the carboxy group.


An imidazol-4-one having a 2-carboxyethyl substituent at the 5-position.


A dicarboxylic acid anion resuting from removal of a proton from both carboxy groups of N-formimidoyl-L-glutamic acid.


A primary amino compound that is the N(tele)-methyl derivative of histamine.


5-Formimidoyltetrahydrofolic acid

The 5-formimidoyl derivative of tetrahydrofolic acid.


methylmalonyl-coenzyme A

The (R)-enantiomer of methylmalonyl-CoA.


The conjugate base of 2-methyl-3-oxopropanoic acid; major species at pH 7.3.


A 3-oxoacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 2-methylacetoacetic acid.


(S)-Methylmalonyl-CoA

The (S)-enantiomer of methylmalonyl-CoA.


Glycocyamine

The N-amidino derivative of glycine.


creatinine

A lactam obtained by formal cyclocondensation of creatine. It is a metabolite of creatine.


2-Oxoadipic acid

An oxo dicarboxylic acid that is adipic acid substituted by an oxo group at position 2.


L-Saccharopine

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


An acyl-CoA oxoanion that is the pentaanion of glutaryl-CoA arising from deprotonation of phosphate, diphosphate and carboxylic acid functions.


methacrylyl-CoA

An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of methacrylic acid.


An acyl-CoA(4-) that is the tetraanion of 3-methylbut-2-enoyl-CoA arising from deprotonation of phosphate and diphosphate functions.


The S-(trans-3-methylglutaconyl) derivative of coenzyme A.


A short chain fatty acyl-CoA(4-) that is the tetraanion of isovaleryl-CoA arising from deprotonation of phosphate and diphosphate functions.


A short-chain, methyl-branched fatty acyl-CoA having 2-methylbutanoyl as the S-acyl group.


An (S)-3-hydroxyacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (2S,3S)-3-hydroxy-2-methylbutanoic acid.


isobutyryl-CoA

A short-chain, methyl-branched fatty acyl-CoA that is the S-isobutyryl derivative of coenzyme A.


A hydroxy fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (S)-3-hydroxyisobutyric acid.


An amino acid zwitterion resulting from the transfer of a proton from the carboxy to the amino group of 2-aminomuconic 6-semialdehyde; major species at pH 7.3.


A dicarboxylic acid monoanion that is the conjugate base of 2-aminomuconic acid. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.).


L-kynurenine

A kynurenine that has L configuration.


The conjugate base of 4-oxobutanoic acid; major species at pH 7.3.


alpha-D-ribofuranose 1-phosphate

Dianion of alpha-D-ribose 1-phosphate arising from deprotonation of both phosphate OH groups; major species at pH 7.3.


2-deoxy-D-ribofuranose 1-phosphate(2-)

Dianion of 2-deoxy-D-ribofuranose 1-phosphate.


A monocarboxylic acid anion that is the conjugate base of 3-ureidoisobutyric acid, obtained by deprotonation of the carboxy group.


Zwitterionic form of (R)-3-aminoisobutyric acid having an anionic carboxy group and a protonated amino group; major species at pH 7.3.


An organophosphate oxoanion resulting from the removal of both protons from the phosphate group of 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide. It is the major species at pH 7.3.


An organophosphate oxoanion that is the tetraanionic form of SAICAR. It is the major species at pH 7.3.


An organophosphate oxoanion that is the major structure at pH 7.3 of 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid.


Dianion of 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.


There is a wrong x-ref in CHEBI:61357 to MetaCyc 5-P-RIBOSYL-N-FORMYLGLYCINEAMIDE


An organophosphate oxoanion obtained by deprotonation of the phosphate OH groups as well as protonation of the endocyclic nitrogen at position 3 in the imidazole ring of 5-amino-1-(5-phospho-beta-D-ribosyl)imidazole. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.).


Methylammonium

The conjugate acid of methylamine; major species at pH 7.3.


Acetoacetic acid

A 3-oxo monocarboxylic acid that is butyric acid bearing a 3-oxo substituent.


(R)-3-Hydroxybutyric acid

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


HMG-CoA

A 3-hydroxy-3-methylglutaryl-CoA where the 3-hydroxy-3-methylglutaryl component has (S)-configuration.


Acetoacetate

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 trans-dec-3-enoic acid.


(2R)-2-hydroxypentanedioic acid

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


A 4-hydroxy monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of 4-hydroxybutyric acid.


alpha,beta-Didehydroalaninate

The conjugate base of 2-aminoacrylic acid; major species at pH 7.3.


nucleoside 5'-monophosphate(2-)

The dianion of a nucleoside monophosphate: major species at pH 7.3.


D-Mannose

D-Mannose in its six-membered ring form.


A branched amino tetrasaccharide comprised of an alpha-D-mannosyl residue linked (1->6) to the middle mannose of alpha-D-Man-(1->3)-beta-D-Man-(1->4)-beta-D-GlcNAc. An intermediate glycan structure of glycosylated proteins.


A six-membered branched glucosamine oligosaccharide consisting of five D-mannosyl residues and one N-acetylglucosamine residue (the latter being located at the reducing end). An intermediate glycan structure of glycosylated proteins.


An amino disaccharide comprising a beta-D-mannose residue linked (1->4) to an N-acetyl-beta-D-glucosamine residue at the reducing end.


Hypothiocyanite

A  sulfur oxoacid that is sulfenic acid in which the hydrogen attached to the sulfur has been replaced by a cyano group.


Hypochlorous Acid

A chlorine oxoacid with formula HOCl; a weak, unstable acid, it is the active form of chlorine in water.


NITRYL CHLORIDE

A nitro compound in which the nitrogen of the nitro group is bonded to a chlorine. It is used as a nitrating and chlorinating agent in organic synthesis.


4-Hydroxyphenylpyruvic acid

A 2-oxo monocarboxylic acid that is pyruvic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.


Icosapent

An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.


14(S)-hydroperoxydocosahexaenoic acid

A hydroperoxy fatty acid that is (4Z,8E,10Z,12E,16Z,19Z)-docosahexaenoic acid in which the hydroperoxy group is located at position 14S. An intermediate of specialised proresolving mediators


A docosanoid that is (4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoic acid carrying a hydroperoxy substituent at position 17R.


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


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


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


A docosanoid that is (4Z,8E,10Z,12E,16Z,19Z)-docosahexaenoic acid carrying two hydroperoxy substituents at the 7S- and 14S-positions.


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


Resolvin D6

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


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


A polyunsaturated fatty acid that is (6E,8Z,11Z,14Z,16E)-icosapentaenoic acid substituted at positions 5 and 18 by hydroperoxy and hydroxy groups respectively (the 5S, 18S-stereoisomer).


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


(18S)-hydroperoxyicosapentaenoic acid

A hydroperoxyicosapentaenoic acid that is an icosapentaenoic acid in which the pro-S hydrogen at position 18 has been replaced by a hydroperoxy group.


18-oxo-Resolvin E1

A nonclassic icosanoid that is (6Z,8E,10E,14Z,16E)-icosa-6,8,10,14,16-pentaenoic acid carrying two hydroxy groups at positions 5 and 12 as well as an oxo group at position 18.


18S-Resolvin E2

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


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


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


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


17-epi-resolvin D5

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


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


Resolvin E2

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


A polyunsaturated fatty acid that is (6E,8Z,11Z,14Z,16E)-icosapentaenoic acid substituted at positions 5 and 18 by hydroperoxy and hydroxy groups respectively (the 5S, 18R-stereoisomer).


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


A hydroperoxyicosapentaenoic acid that is (5Z,8Z,11Z,14Z,16E)-icosapentaenoic acid in which the pro-R hydrogen at position 18 has been replaced by a hydroperoxy group. One of the two stereoisomers formed when acetylated COX2 oxidises the omega-3 fatty acid EPA.


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


A polyunsaturated fatty acid anion that is the conjugate base of (13R)-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoic acid, arising from deprotonation of the carboxylic acid group; major species at pH 7.3. It is an intermediate in 13-series resolvins biosynthesis from DPA (omega-3).


A polyunsaturated fatty acid anion that is the conjugate base of (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.


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


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


A (7Z,10Z,12E,16Z,19Z)-14-hydroperoxydocosapentaenoic acid in which the chiral centre at position 14 has S-configuration. An intermediate of specialised proresolving mediators.


A docosanoid that is (7R,17S)-dihydroxy-(4Z,9,11,13Z,15E,19Z)-docosahexaenoic acid in which a cysteinyl group is attached at position 8S via a sulfide linkage. An intermediate of specialised proresolving mediators.


A docosanoid that is (14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoic acid in which a glutathionyl group is attached at position 13R via a sulfide linkage.


A docosanoid that is (14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoic acid in which a cysteinylglycinyl group is attached at position 13R via a sulfide linkage.