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Identification
YMDB IDYMDB00276
NamePhosphoenolpyruvic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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.
Structure
Thumb
Synonyms
  • 2-(phosphonooxy)-2-propenoate
  • 2-(phosphonooxy)acrylate
  • 2-hydroxy-2-propenoate (dihydrogen phosphate) (ester)
  • 2-hydroxy-2-propenoate phosphate (ester)
  • 2-hydroxy-Acrylic acid dihydrogen phosphate
  • 2-phosphonooxyprop-2-enoate
  • 2-phosphonooxyprop-2-enoic acid
  • O-phosphono-enol-pyruvate
  • P-enol-pyruvate
  • PEP
  • pep, phosphoenolpyruvic acid
  • Phosphoenolpyruvate
  • phosphoenolpyruvate(1-)
  • Phosphoenolpyruvic acid
  • 2-(Phosphonooxy)-2-propenoic acid
  • 2-PHOSPHOENOLPYRUVIC ACID
  • 2-PHOSPHOENOLPYRUVate
CAS number138-08-9
WeightAverage: 168.042
Monoisotopic: 167.982374404
InChI KeyDTBNBXWJWCWCIK-UHFFFAOYSA-N
InChIInChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)
IUPAC Name2-(phosphonooxy)prop-2-enoic acid
Traditional IUPAC Namephosphoenolpyruvic acid
Chemical FormulaC3H5O6P
SMILES[H]OC(=O)C(OP(=O)(O[H])O[H])=C([H])[H]
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility13.2 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondrion
Organoleptic PropertiesNot Available
SMPDB Pathways
Ethanol fermentationPW002448 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycolysis IPW002386 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyruvate metabolismPW002447 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Citrate cycle (TCA cycle)ec00020 Map00020
Glycolysis / Gluconeogenesisec00010 Map00010
Methane metabolismec00680 Map00680
Phenylalanine, tyrosine and tryptophan biosynthesisec00400 Map00400
Pyruvate metabolismec00620 Map00620
SMPDB Reactions
2-phospho-D-glyceric acidPhosphoenolpyruvic acid + water
Adenosine triphosphate + Pyruvic acidADP + Phosphoenolpyruvic acid
Adenosine triphosphate + Pyruvic acidADP + Phosphoenolpyruvic acid
Adenosine triphosphate + Oxalacetic acidADP + Phosphoenolpyruvic acid
KEGG Reactions
D-Erythrose 4-phosphate + Phosphoenolpyruvic acid + waterphosphate + 7-phospho-2-dehydro-3-deoxy-D-arabino-heptonic acid
Phosphoenolpyruvic acid + 3-Phosphoshikimic acidphosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimic acid
2-phospho-D-glyceric acidPhosphoenolpyruvic acid + water
Adenosine triphosphate + Oxalacetic acidPhosphoenolpyruvic acid + Carbon dioxide + ADP
Phosphoenolpyruvic acid + hydron + ADPPyruvic acid + Adenosine triphosphate
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
15 ± 15 µM Synthetic medium with 2% glucoseaerobic;growing cellsBaker's yeastPMID: 6229402
15 ± 15 µM Synthetic medium with 2% galactoseaerobic;resting cellsBaker's yeastPMID: 6229402
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0292-0962000000-44d3914b4e07e5c50e3fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0292-0962000000-44d3914b4e07e5c50e3fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9200000000-ae9d81fc88a98f678268JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9410000000-072478606f0ab6809902JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udr-1900000000-9a4f5554af9a717d99c7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000x-9200000000-6cdc15f3daa25fc41655JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9100000000-39e22409d6d924a774f1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00xu-0912000000-ad1823470675975d5ff0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-1f5b761ce5fa374b0f8eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-d279f0ca2accb130181fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0920000000-f084dccf78e11c8760d7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00lr-0911000000-7fa833698210746c838fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-62e28301f20b08971b78JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-25f970898112f7b89898JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0930000000-58691b23d317c2418c33JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00p0-0493110000-9d61bb13ab5261fdf9fdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-9100000000-db409b3cfa9ebabbcb58JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4j-5090000000-1ee56bc4866301d4bf2eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0090000000-bce08b01d44391bfecadJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-016r-7900000000-ffd3b8dcd65aaea26ac3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-9000000000-ceae3587b1e7d8b3da27JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-701a17330cd18255d625JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-a4178ce4951e2c3dba7bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-9d0421620a7aaa9ef33fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0k9i-1900000000-fb12ade375a7ac97f150JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0f76-8900000000-7f57e6a8e72e5992cd88JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000j-9300000000-c02bca019150d572b3bcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-05bf-9200000000-73fa5ca52ecc17bac380JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0079-9300000000-231346190165f44f28dcJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Thevelein, J. M., Hohmann, S. (1995). "Trehalose synthase: guard to the gate of glycolysis in yeast?" Trends Biochem Sci 20:3-10.7878741
  • Schwartz, J. M., Kanehisa, M. (2006). "Quantitative elementary mode analysis of metabolic pathways: the example of yeast glycolysis." BMC Bioinformatics 7:186.16584566
  • Braus, G. H. (1991). "Aromatic amino acid biosynthesis in the yeast Saccharomyces cerevisiae: a model system for the regulation of a eukaryotic biosynthetic pathway." Microbiol Rev 55:349-370.1943992
  • Larimer, F. W., Morse, C. C., Beck, A. K., Cole, K. W., Gaertner, F. H. (1983). "Isolation of the ARO1 cluster gene of Saccharomyces cerevisiae." Mol Cell Biol 3:1609-1614.6355828
  • Burke, R. L., Tekamp-Olson, P., Najarian, R. (1983). "The isolation, characterization, and sequence of the pyruvate kinase gene of Saccharomyces cerevisiae." J Biol Chem 258:2193-2201.6185493
  • Teshiba, S., Furter, R., Niederberger, P., Braus, G., Paravicini, G., Hutter, R. (1986). "Cloning of the ARO3 gene of Saccharomyces cerevisiae and its regulation." Mol Gen Genet 205:353-357.2880280
  • Lagunas, R., Gancedo, C. (1983). "Role of phosphate in the regulation of the Pasteur effect in Saccharomyces cerevisiae." Eur J Biochem 137:479-483.6229402
Synthesis Reference:Simon, 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.
External Links:
ResourceLink
CHEBI ID44897
HMDB IDHMDB00263
Pubchem Compound ID1005
Kegg IDC00074
ChemSpider ID980
FOODB IDFDB001451
WikipediaPhosphoenolpyruvic_acid
BioCyc IDPHOSPHO-ENOL-PYRUVATE

Enzymes

General function:
Involved in 3-dehydroquinate dehydratase activity
Specific function:
The AROM polypeptide catalyzes 5 consecutive enzymatic reactions in prechorismate polyaromatic amino acid biosynthesis
Gene Name:
ARO1
Uniprot ID:
P08566
Molecular weight:
174754.0
Reactions
3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate → 3-dehydroquinate + phosphate.
3-dehydroquinate → 3-dehydroshikimate + H(2)O.
Shikimate + NADP(+) → 3-dehydroshikimate + NADPH.
ATP + shikimate → ADP + shikimate 3-phosphate.
Phosphoenolpyruvate + 3-phosphoshikimate → phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate.
General function:
Involved in catalytic activity
Specific function:
Stereospecific condensation of phosphoenolpyruvate (PEP) and D-erythrose-4-phosphate (E4P) giving rise to 3-deoxy-D- arabino-heptulosonate-7-phosphate (DAHP)
Gene Name:
ARO4
Uniprot ID:
P32449
Molecular weight:
39748.80078
Reactions
Phosphoenolpyruvate + D-erythrose 4-phosphate + H(2)O → 3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate + phosphate.
General function:
Involved in catalytic activity
Specific function:
Stereospecific condensation of phosphoenolpyruvate (PEP) and D-erythrose-4-phosphate (E4P) giving rise to 3-deoxy-D- arabino-heptulosonate-7-phosphate (DAHP)
Gene Name:
ARO3
Uniprot ID:
P14843
Molecular weight:
41069.5
Reactions
Phosphoenolpyruvate + D-erythrose 4-phosphate + H(2)O → 3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate + phosphate.
General function:
Involved in magnesium ion binding
Specific function:
ATP + pyruvate = ADP + phosphoenolpyruvate
Gene Name:
PYK1
Uniprot ID:
P00549
Molecular weight:
54544.10156
Reactions
ATP + pyruvate → ADP + phosphoenolpyruvate.
General function:
Involved in magnesium ion binding
Specific function:
May be used by cells under conditions in which the level of glycolytic flux is very low
Gene Name:
PYK2
Uniprot ID:
P52489
Molecular weight:
55194.69922
Reactions
ATP + pyruvate → ADP + phosphoenolpyruvate.
General function:
Involved in phosphoenolpyruvate carboxykinase (ATP) activity
Specific function:
ATP + oxaloacetate = ADP + phosphoenolpyruvate + CO(2)
Gene Name:
PCK1
Uniprot ID:
P10963
Molecular weight:
60982.69922
Reactions
ATP + oxaloacetate → ADP + phosphoenolpyruvate + CO(2).
General function:
Involved in magnesium ion binding
Specific function:
2-phospho-D-glycerate = phosphoenolpyruvate + H(2)O
Gene Name:
ERR1
Uniprot ID:
Q12007
Molecular weight:
47327.10156
Reactions
2-phospho-D-glycerate → phosphoenolpyruvate + H(2)O.
General function:
Involved in magnesium ion binding
Specific function:
2-phospho-D-glycerate = phosphoenolpyruvate + H(2)O
Gene Name:
ERR3
Uniprot ID:
P42222
Molecular weight:
47312.10156
Reactions
2-phospho-D-glycerate → phosphoenolpyruvate + H(2)O.
General function:
Involved in magnesium ion binding
Specific function:
2-phospho-D-glycerate = phosphoenolpyruvate + H(2)O
Gene Name:
ENO1
Uniprot ID:
P00924
Molecular weight:
46815.69922
Reactions
2-phospho-D-glycerate → phosphoenolpyruvate + H(2)O.
General function:
Involved in magnesium ion binding
Specific function:
2-phospho-D-glycerate = phosphoenolpyruvate + H(2)O
Gene Name:
ENO2
Uniprot ID:
P00925
Molecular weight:
46913.69922
Reactions
2-phospho-D-glycerate → phosphoenolpyruvate + H(2)O.

Transporters

General function:
Involved in binding
Specific function:
Transport of citrate across inner mitochondrial membrane
Gene Name:
CTP1
Uniprot ID:
P38152
Molecular weight:
32173.0