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Record Information
Version1.0
Creation Date2016-07-13 19:42:50 UTC
Update Date2016-07-20 20:56:42 UTC
LmdbLMDB00122
Secondary Accession NumbersNone
Metabolite Identification
Common NamePhosphoenolpyruvic acid
DescriptionPhosphoenolpyruvate (PEP) is an important chemical compound in biochemistry. It has a high energy phosphate bond, and is involved in glycolysis and gluconeogenesis. In glycolysis, PEP is formed by the action of the enzyme enolase on 2-phosphoglycerate. Metabolism of PEP to pyruvate by pyruvate kinase (PK) generates 1 molecule of adenosine triphosphate (ATP) via substrate-level phosphorylation. ATP is one of the major currencies of chemical energy within cells. In gluconeogenesis, PEP is formed from the decarboxylation of oxaloacetate and hydrolysis of 1 guanosine triphosphate molecule. This reaction is catalyzed by the enzyme phosphoenolpyruvate carboxykinase (PEPCK). This reaction is a rate-limiting step in gluconeogenesis. (wikipedia).
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
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
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 KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0292-0962000000-44d3914b4e07e5c50e3fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0292-0962000000-44d3914b4e07e5c50e3fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9200000000-ae9d81fc88a98f678268Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9410000000-072478606f0ab6809902Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00p0-0493110000-9d61bb13ab5261fdf9fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-9100000000-db409b3cfa9ebabbcb58Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4j-5090000000-1ee56bc4866301d4bf2eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0090000000-bce08b01d44391bfecadSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-016r-7900000000-ffd3b8dcd65aaea26ac3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-9000000000-ceae3587b1e7d8b3da27Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-701a17330cd18255d625Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-a4178ce4951e2c3dba7bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-9d0421620a7aaa9ef33fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004i-9100000000-33b795aea615bc3ef7fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-016r-7900000000-ffd3b8dcd65aaea26ac3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-ceae3587b1e7d8b3da27Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-701a17330cd18255d625Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-a4178ce4951e2c3dba7bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-9d0421620a7aaa9ef33fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9100000000-db409b3cfa9ebabbcb58Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4j-5090000000-1ee56bc4866301d4bf2eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0090000000-bce08b01d44391bfecadSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-9100000000-33b795aea615bc3ef7fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-00di-0900000000-5200e24d9bacedeb3612Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-9000000000-64c7b0a6d679df615962Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-9000000000-54ff8e6208b30c8f879eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-10d0f179adb0e6bdec0dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f253c7e0f0c1a8352903Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-8310e25f1579dbfbf6f4Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Milk
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
DrugBank IDDB01819
HMDB IDHMDB0000263
FooDB IDFDB031112
Phenol Explorer IDNot Available
KNApSAcK IDC00000798
BiGG IDNot Available
BioCyc IDPHOSPHO-ENOL-PYRUVATE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPhosphoenolpyruvic_acid
Chemspider ID980
ChEBI ID44897
PubChem Compound ID1005
Kegg Compound IDC00074
YMDB IDYMDB00276
ECMDB IDECMDB00263
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available