phosphoenolpyruvate (PAMDB110154)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110154
Identification
Name: phosphoenolpyruvate
Description:An organophosphate oxoanion obtained by deprotonation of the carboxy and phosphate groups of phosphoenolpyruvic acid.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • P-enol-pyr
  • P-enol-pyruvate
  • P-enol-pyruvate
  • P-enol-pyr
  • PEP
Chemical Formula: C3H2O6P
Average Molecular Weight: 165.02
Monoisotopic Molecular Weight: 167.9823744031
InChI Key: DTBNBXWJWCWCIK-UHFFFAOYSA-K
InChI: InChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)/p-3
CAS number: 138-08-9
IUPAC Name:2-(phosphonoatooxy)prop-2-enoate
Traditional IUPAC Name: phosphoenolpyruvic acid
SMILES:C=C(OP([O-])([O-])=O)C([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities 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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassOrganic phosphoric acids and derivatives
Direct Parent Phosphate 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 Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility13.2 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.13 m3·mol-1ChemAxon
Polarizability11.57 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
pyruvate + GTP → phosphoenolpyruvate + GDP + Hydrogen ion
pyruvate + dATP → phosphoenolpyruvate + dADP + Hydrogen ion
pyruvate + dGTP → phosphoenolpyruvate + dGDP + Hydrogen ion
phosphoenolpyruvate + PTS-I-Histidines → pyruvate + PTS-I-pi-phospho-L-histidines
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0292-0962000000-44d3914b4e07e5c50e3fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udr-1900000000-9a4f5554af9a717d99c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000x-9200000000-6cdc15f3daa25fc41655View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9100000000-39e22409d6d924a774f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00xu-0912000000-ad1823470675975d5ff0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-1f5b761ce5fa374b0f8eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-d279f0ca2accb130181fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0920000000-f084dccf78e11c8760d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00lr-0911000000-7fa833698210746c838fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-62e28301f20b08971b78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-25f970898112f7b89898View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0930000000-58691b23d317c2418c33View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00p0-0493110000-9d61bb13ab5261fdf9fdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-9100000000-db409b3cfa9ebabbcb58View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4j-5090000000-1ee56bc4866301d4bf2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0090000000-bce08b01d44391bfecadView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-016r-7900000000-ffd3b8dcd65aaea26ac3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-9000000000-ceae3587b1e7d8b3da27View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-701a17330cd18255d625View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-a4178ce4951e2c3dba7bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-9d0421620a7aaa9ef33fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0k9i-1900000000-fb12ade375a7ac97f150View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0f76-8900000000-7f57e6a8e72e5992cd88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000j-9300000000-c02bca019150d572b3bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-05bf-9200000000-73fa5ca52ecc17bac380View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0079-9300000000-231346190165f44f28dcView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. [19212411 ]
  • Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. [15882454 ]
  • Krogh P: Role of ochratoxin in disease causation. Food Chem Toxicol. 1992 Mar;30(3):213-24. [1618445 ]
  • Germaine GR, Tellefson LM: Promotion of Streptococcus mutans glucose transport by human whole saliva and parotid fluid. Infect Immun. 1985 Apr;48(1):7-13. [3980096 ]
  • Schatzberger P: Maternity services. BMJ. 1992 May 23;304(6838):1382-3. [1611358 ]
  • Orye E, Verhaaren H, Samuel K, van Mele B: A 46,XX,10Q+ chromosome constitution in a girl. Partial long arm duplication or insertional translocation? Humangenetik. 1975 May 26;28(1):1-8. [1150258 ]
  • Landau BR, Chandramouli V, Schumann WC, Ekberg K, Kumaran K, Kalhan SC, Wahren J: Estimates of Krebs cycle activity and contributions of gluconeogenesis to hepatic glucose production in fasting healthy subjects and IDDM patients. Diabetologia. 1995 Jul;38(7):831-8. [7556986 ]
  • Shirokane Y, Nakajima M, Mizusawa K: A new enzymatic assay of urinary guanidinoacetic acid. Clin Chim Acta. 1991 Oct 31;202(3):227-36. [1667626 ]
  • Tannen RL: Ammonia metabolism. Am J Physiol. 1978 Oct;235(4):F265-77. [29492 ]
  • Atkin BM, Buist NR, Utter MF, Leiter AB, Banker BQ: Pyruvate carboxylase deficiency and lactic acidosis in a retarded child without Leigh's disease. Pediatr Res. 1979 Feb;13(2):109-16. [219411 ]
  • Bojarska-Dahlig H, Gloabski T, Dzioegielewska I: [Salts of cyclic erythromycin A carbonate with cinnamic acid derivatives] Acta Pol Pharm. 1975;32(3):311-7. [1155186 ]
  • Matsumoto T, van der Auwera P, Watanabe Y, Tanaka M, Ogata N, Naito S, Kumazawa J: Neutrophil function in hyperosmotic NaCl is preserved by phosphoenol pyruvate. Urol Res. 1991;19(4):223-7. [1656579 ]
  • Cahill GF Jr, Aoki TT: Renal gluconeogenesis and amino-acid metabolism in man. Med Clin North Am. 1975 May;59(3):751-61. [1092934 ]
  • Beyer C: Creatine measurement in serum and urine with an automated enzymatic method. Clin Chem. 1993 Aug;39(8):1613-9. [8353946 ]
  • Momeni N, Yoshimoto T, Ryberg B, Sandberg-Wollheim M, Grubb A: Factors influencing analysis of prolyl endopeptidase in human blood and cerebrospinal fluid: increase in assay sensitivity. Scand J Clin Lab Invest. 2003;63(6):387-95. [14594319 ]
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.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CAS73-89-2
CAS138-08-9
ChEBI58702
ChemSpider2907208
HMDBHMDB00263
IAF126033756
KEGGC00074
PubChem3674425