CHEBI:17981 - O-acetyl-L-serine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name O-acetyl-L-serine
ChEBI ID CHEBI:17981
ChEBI ASCII Name O-acetyl-L-serine
Definition An acetyl-L-serine where the acetyl group is attached to the side-chain oxygen. It is an intermediate in the biosynthesis of the amino acid cysteine in bacteria.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:12724, CHEBI:7668, CHEBI:44568, CHEBI:12710, CHEBI:12685, CHEBI:21938
Supplier Information ZINC000004546338
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5-Hydroxyeicosatetraenoic acid (5-HETE, 5(S)-HETE, or 5S-HETE) is an eicosanoid, i.e. a metabolite of arachidonic acid. It is produced by diverse cell types in humans and other animal species. These cells may then metabolize the formed 5(S)-HETE to 5-oxo-eicosatetraenoic acid (5-oxo-ETE), 5(S),15(S)-dihydroxyeicosatetraenoic acid (5(S),15(S)-diHETE), or 5-oxo-15-hydroxyeicosatetraenoic acid (5-oxo-15(S)-HETE). 5(S)-HETE, 5-oxo-ETE, 5(S),15(S)-diHETE, and 5-oxo-15(S)-HETE, while differing in potencies, share a common mechanism for activating cells and a common set of activities. They are therefore a family of structurally related metabolites. Animal studies and a limited set of human studies suggest that this family of metabolites serve as hormone-like autocrine and paracrine signalling agents that contribute to the up-regulation of acute inflammatory and allergic responses. In this capacity, these metabolites may be members of the innate immune system. In vitro studies suggest that 5(S)-HETE and/or other of its family members may also be active in promoting the growth of certain types of cancers, in simulating bone reabsorption, in signaling for the secretion of aldosterone and progesterone, in triggering parturition, and in contributing to other responses in animals and humans. However, the roles of 5(S)-HETE family members in these responses as well as in inflammation and allergy are unproven and will require much further study. Among the 5(S)-HETE family members, 5(S)-HETE takes precedence over the other members of this family because it was the first to be discovered and has been studied far more thoroughly. However, 5-oxo-ETE is the most potent member of this family and therefore may be its critical member with respect to physiology and pathology. 5-OxoETE has gained attention in recent studies.
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Formula C5H9NO4
Net Charge 0
Average Mass 147.12930
Monoisotopic Mass 147.05316
InChI InChI=1S/C5H9NO4/c1-3(7)10-2-4(6)5(8)9/h4H,2,6H2,1H3,(H,8,9)/t4-/m0/s1
InChIKey VZXPDPZARILFQX-BYPYZUCNSA-N
SMILES CC(=O)OC[C@H](N)C(O)=O
Metabolite of Species Details
Saccharomyces cerevisiae (NCBI:txid4932) Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Homo sapiens (NCBI:txid9606) See: MetaboLights Study
Roles Classification
Biological Role(s): Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing O-acetyl-L-serine (CHEBI:17981) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
O-acetyl-L-serine (CHEBI:17981) has role bacterial metabolite (CHEBI:76969)
O-acetyl-L-serine (CHEBI:17981) is a acetate ester (CHEBI:47622)
O-acetyl-L-serine (CHEBI:17981) is a acetyl-L-serine (CHEBI:22194)
O-acetyl-L-serine (CHEBI:17981) is tautomer of O-acetyl-L-serine zwitterion (CHEBI:58340)
Incoming O-acetyl-L-serine residue (CHEBI:141128) is substituent group from O-acetyl-L-serine (CHEBI:17981)
O-acetyl-L-serine zwitterion (CHEBI:58340) is tautomer of O-acetyl-L-serine (CHEBI:17981)
IUPAC Name
O-acetyl-L-serine
Synonyms Sources
L-Serine, acetate (ester) ChemIDplus
O-acetyl-L-serine ChEBI
O-Acetyl-L-serine KEGG COMPOUND
O3-acetyl-L-serine ChEBI
O3-Acetyl-L-serine KEGG COMPOUND
Manual Xrefs Databases
ACETYLSERINE MetaCyc
C00007459 KNApSAcK
C00979 KEGG COMPOUND
DB01837 DrugBank
HMDB0003011 HMDB
O-Acetylserine Wikipedia
OAS PDBeChem
View more database links
Registry Numbers Types Sources
1723791 Reaxys Registry Number Reaxys
5147-00-2 CAS Registry Number KEGG COMPOUND
5147-00-2 CAS Registry Number ChemIDplus
Citation Type Source
23483228 PubMed citation Europe PMC
Last Modified
12 February 2016