Back to Compounds

Phosphoenolpyruvic acid (PC000249)

Record Information
Version1.0
Creation date2015-10-09 22:29:26 UTC
Update date2017-01-19 02:36:18 UTC
FoodComEx IDPC000249
FoodDB RecordFDB001451
Chemical Information
NamePhosphoenolpyruvic acid
DescriptionPhosphoenolpyruvic acid, also known as PEP or 2-phosphonooxyprop-2-enoate, belongs to the class of organic compounds known as phosphate esters. These are organic compounds containing phosphoric acid ester functional group, with the general structure R1P(=O)(R2)OR3. R1,R2 = O,N, or halogen atom; R3 = organyl group. Phosphoenolpyruvic acid is an extremely strong acidic compound (based on its pKa). Phosphoenolpyruvic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, Phosphoenolpyruvic acid has been detected, but not quantified in, several different foods, such as pepper (c. frutescens), grapes, mexican groundcherries, black raspberries, and wasabis. This could make phosphoenolpyruvic acid a potential biomarker for the consumption of these foods.
CAS Number138-08-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1nhxbiospider
2-(Onooxy)-2-propenoateGenerator
2-(Onooxy)-2-propenoic acidChEBI
2-(phosphonooxy)-2-propenoic acidbiospider
2-(Phosphonooxy)acrylatebiospider
2-(phosphonooxy)prop-2-enoic acidbiospider
2-Dihydroxyphosphinoyloxyacrylic acidbiospider
2-Hydroxy-acrylic acid dihydrogen ateHMDB
2-hydroxy-Acrylic acid dihydrogen phosphatebiospider
2-OENOLPYRUVateGenerator
2-OENOLPYRUVIC ACIDChEBI
2-Onooxyprop-2-enoateHMDB
2-Onooxyprop-2-enoic acidHMDB
2-PHOSPHOENOLPYRUVIC ACIDbiospider
2-phosphonooxyprop-2-enoatebiospider
2-phosphonooxyprop-2-enoic acidbiospider
2-Propenoic acid, 2-(phosphonooxy)-biospider
2-Propenoic acid, 2-(phosphonooxy)-, ion(1-)biospider
Acrylic acid, 2-hydroxy-, dihydrogen phosphatebiospider
Barium silver 2-(phosphonatooxy)acrylatebiospider
OENOLPYRUVATEChEBI
Oenolpyruvic acidChEBI
P-enol-PYRbiospider
P-enol-pyruvatebiospider
PEPbiospider
Phospho-enol-pyruvatebiospider
Phosphoenolpyruvatebiospider
Phosphopyruvic acidbiospider
Chemical FormulaC3H5O6P
IUPAC name2-(phosphonooxy)prop-2-enoic acid
InChI IdentifierInChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)
InChI KeyDTBNBXWJWCWCIK-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C(=C)OP(O)(O)=O
Average Molecular Weight168.042
Monoisotopic Molecular Weight167.982374404
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphate esters. These are organic compounds containing phosphoric acid ester functional group, with the general structure R1P(=O)(R2)OR3. R1,R2 = O,N, or halogen atom; R3 = organyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentPhosphate esters
Alternative Parents
Substituents
  • Phosphoric acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 50 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Not Available