CHEBI:44897 - phosphoenolpyruvic acid

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ChEBI Name phosphoenolpyruvic acid
ChEBI ID CHEBI:44897
ChEBI ASCII Name phosphoenolpyruvic acid
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:44894, CHEBI:26055
Supplier Information eMolecules:30520770
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Wikipedia License
Methyl cinnamate is the methyl ester of cinnamic acid and is a white or transparent solid with a strong, aromatic odor. It is found naturally in a variety of plants, including in fruits, like strawberry, and some culinary spices, such as Sichuan pepper and some varieties of basil. Eucalyptus olida has the highest known concentrations of methyl cinnamate (98%) with a 2–6% fresh weight yield in the leaf and twigs. Methyl cinnamate is used in the flavor and perfume industries. The flavor is fruity and strawberry-like; and the odor is sweet, balsamic with fruity odor, reminiscent of cinnamon and strawberry. It is known to attract males of various orchid bees, such as Aglae caerulea.
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Formula C3H5O6P
Net Charge 0
Average Mass 168.04196
Monoisotopic Mass 167.98237
InChI InChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)
InChIKey DTBNBXWJWCWCIK-UHFFFAOYSA-N
SMILES OC(=O)C(=C)OP(O)(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): fundamental metabolite
Any metabolite produced by all living cells.
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ChEBI Ontology
Outgoing 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 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 Sources
2-(phosphonooxy)-2-propenoic acid ChemIDplus
2-PHOSPHOENOLPYRUVIC ACID PDBeChem
PEP KEGG COMPOUND
PHOSPHOENOLPYRUVATE PDBeChem
Phosphoenolpyruvic acid KEGG COMPOUND
Manual Xrefs Databases
C00000798 KNApSAcK
C00074 KEGG COMPOUND
DB01819 DrugBank
HMDB0000263 HMDB
PEP PDBeChem
Phosphoenolpyruvic_acid Wikipedia
View more database links
Registry Numbers Types Sources
138-08-9 CAS Registry Number ChemIDplus
1775389 Reaxys Registry Number Reaxys
Last Modified
18 April 2024