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CHEBI:44897 - phosphoenolpyruvic acid

Default Structure
ChEBI IDCHEBI:44897
ChEBI Namephosphoenolpyruvic acid
Stars
ASCII Namephosphoenolpyruvic acid
DefinitionA monocarboxylic acid that is acrylic acid substituted by a phosphonooxy group at position 2. It is a metabolic intermediate in pathways like glycolysis and gluconeogenesis.
Secondary ChEBI IDsCHEBI:26055, CHEBI:44894
Last Modified18 April 2024
DownloadsMolfile
FormulaC3H5O6P
Net Charge0
Average Mass168.041
Monoisotopic Mass167.98237
SMILESC=C(OP(=O)(O)O)C(=O)O
InChIInChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)
InChIKeyDTBNBXWJWCWCIK-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
fundamental metabolite  Any metabolite produced by all living cells.
ChEBI Ontology
Outgoing Relation(s)
phosphoenolpyruvic acid (CHEBI:44897) has functional parent acrylic acid (CHEBI:18308)
phosphoenolpyruvic acid (CHEBI:44897) has role fundamental metabolite (CHEBI:78675)
phosphoenolpyruvic acid (CHEBI:44897) is a carboxyalkyl phosphate (CHEBI:36952)
phosphoenolpyruvic acid (CHEBI:44897) is a monocarboxylic acid (CHEBI:25384)
phosphoenolpyruvic acid (CHEBI:44897) is conjugate acid of phosphoenolpyruvate (CHEBI:18021)
phosphoenolpyruvic acid (CHEBI:44897) is conjugate acid of phosphonatoenolpyruvate (CHEBI:58702)
Incoming Relation(s)
phosphoenolpyruvate (CHEBI:18021) is conjugate base of phosphoenolpyruvic acid (CHEBI:44897)
phosphonatoenolpyruvate (CHEBI:58702) is conjugate base of phosphoenolpyruvic acid (CHEBI:44897)
IUPAC Name 
2-(phosphonooxy)prop-2-enoic acid
Synonyms  Source
2-PHOSPHOENOLPYRUVIC ACIDPDBeChem
2-(phosphonooxy)-2-propenoic acidChemIDplus
PEPKEGG COMPOUND
PHOSPHOENOLPYRUVATEPDBeChem
Phosphoenolpyruvic acidKEGG COMPOUND
Manual XrefsDatabases
C00000798KNApSAcK
C00074KEGG COMPOUND
DB01819DrugBank
HMDB0000263HMDB
PEPPDBeChem
Phosphoenolpyruvic_acidWikipedia
Registry NumbersSources
Reaxys:1775389Reaxys
CAS:138-08-9KEGG COMPOUND
CAS:138-08-9ChemIDplus