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Record Information
Version1.0
Creation Date2016-09-30 22:27:35 UTC
Update Date2020-05-21 16:28:28 UTC
BMDB IDBMDB0000263
Secondary Accession Numbers
  • BMDB00263
Metabolite Identification
Common 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 possibly soluble (in water) and an extremely strong acidic compound (based on its pKa). Phosphoenolpyruvic acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
ValueSource
2-(Phosphonooxy)-2-propenoic acidChEBI
2-PHOSPHOENOLPYRUVIC ACIDChEBI
PEPChEBI
PHOSPHOENOLPYRUVATEChEBI
2-(Phosphonooxy)-2-propenoateGenerator
2-PHOSPHOENOLPYRUVateGenerator
2-Hydroxy-acrylic acid dihydrogen phosphateHMDB
2-Phosphonooxyprop-2-enoateHMDB
2-Phosphonooxyprop-2-enoic acidHMDB
p-enol-PyruvateHMDB
PEP (phosphate)HMDB
Phosphoenolpyruvic acidHMDB
Chemical FormulaC3H5O6P
Average Molecular Weight168.042
Monoisotopic Molecular Weight167.982374404
IUPAC Name2-(phosphonooxy)prop-2-enoic acid
Traditional Namephosphoenolpyruvic acid
CAS Registry Number138-08-9
SMILES
OC(=O)C(=C)OP(O)(O)=O
InChI Identifier
InChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)
InChI KeyDTBNBXWJWCWCIK-UHFFFAOYSA-N
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
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.2ALOGPS
logP-0.64ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)0.76ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.13 m³·mol⁻¹ChemAxon
Polarizability11.57 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Liver
  • Milk
  • Placenta
  • Prostate Tissue
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000263
DrugBank IDDB01819
Phenol Explorer Compound IDNot Available
FooDB IDFDB031112
KNApSAcK IDC00000798
Chemspider ID980
KEGG Compound IDC00074
BioCyc IDPHOSPHO-ENOL-PYRUVATE
BiGG IDNot Available
Wikipedia LinkPhosphoenolpyruvic_acid
METLIN IDNot Available
PubChem Compound1005
PDB IDNot Available
ChEBI ID44897
References
Synthesis ReferenceSimon, Ethan S.; Grabowski, Sven; Whitesides, George M. Preparation of phosphoenolpyruvate from D-(-)-3-phosphoglyceric acid for use in regeneration of ATP. Journal of the American Chemical Society (1989), 111(24), 8920-1.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]

Enzymes

General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
PKM
Uniprot ID:
B3IVN4
Molecular weight:
16527.0
General function:
Carbohydrate transport and metabolism
Specific function:
Appears to have a function in striated muscle development and regeneration.
Gene Name:
ENO3
Uniprot ID:
Q3ZC09
Molecular weight:
47096.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
PKM2
Uniprot ID:
Q3ZC87
Molecular weight:
61428.0
General function:
Carbohydrate transport and metabolism
Specific function:
Glycolytic enzyme the catalyzes the conversion of 2-phosphoglycerate to phosphoenolpyruvate (By similarity). In addition to glycolysis, involved in various processes such as growth control, hypoxia tolerance and allergic responses (PubMed:7499243). May also function in the intravascular and pericellular fibrinolytic system due to its ability to serve as a receptor and activator of plasminogen on the cell surface of several cell-types such as leukocytes and neurons (By similarity). Stimulates immunoglobulin production (By similarity).
Gene Name:
ENO1
Uniprot ID:
Q9XSJ4
Molecular weight:
47326.0
Reactions
2-Phospho-D-glyceric acid → Phosphoenolpyruvic acid + Waterdetails
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
PKLR
Uniprot ID:
Q1JPG7
Molecular weight:
56870.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
ENO2
Uniprot ID:
A6QR19
Molecular weight:
47269.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
PKM
Uniprot ID:
A5D984
Molecular weight:
57949.0
Reactions
Adenosine triphosphate + Pyruvic acid → ADP + Phosphoenolpyruvic aciddetails
General function:
Energy production and conversion
Specific function:
Regulates cataplerosis and anaplerosis, the processes that control the levels of metabolic intermediates in the citric acid cycle. At low glucose levels, it catalyzes the cataplerotic conversion of oxaloacetate (OAA) to phosphoenolpyruvate (PEP), the rate-limiting step in the metabolic pathway that produces glucose from lactate and other precursors derived from the citric acid cycle. At high glucose levels, it catalyzes the anaplerotic conversion of phosphoenolpyruvate to oxaloacetate.
Gene Name:
PCK1
Uniprot ID:
Q8HYZ4
Molecular weight:
69353.0
Reactions
Guanosine triphosphate + Oxalacetic acid → Guanosine diphosphate + Phosphoenolpyruvic acid + Carbon dioxidedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
NANS
Uniprot ID:
Q1RMX7
Molecular weight:
40217.0
Reactions
N-Acetyl-D-mannosamine + Phosphoenolpyruvic acid + Water → N-Acetylneuraminic acid + Hydrogen phosphatedetails