Phosphoenolpyruvate

Identification

Name
Phosphoenolpyruvate
Accession Number
DB01819  (EXPT02550)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
Not Available
Product Ingredients
Not Available
Approved Prescription Products
Not Available
Approved Generic Prescription Products
Not Available
Approved Over the Counter Products
Not Available
Unapproved/Other Products
Not Available
International/Other Brands
Not Available
Brand mixtures
Not Available
Categories
UNII
545YL308OW
CAS number
138-08-9
Weight
Average: 168.042
Monoisotopic: 167.982374404
Chemical Formula
C3H5O6P
InChI Key
DTBNBXWJWCWCIK-UHFFFAOYSA-N
InChI
InChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)
IUPAC Name
2-(phosphonooxy)prop-2-enoic acid
SMILES
OC(=O)C(=C)OP(O)(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U2-dehydro-3-deoxyphosphooctonate aldolaseNot AvailableShigella flexneri
UBeta-enolaseNot AvailableHuman
UPhosphoenolpyruvate carboxykinase, cytosolic [GTP]Not AvailableHuman
U2-dehydro-3-deoxyphosphooctonate aldolaseNot AvailableAquifex aeolicus (strain VF5)
UPhospho-2-dehydro-3-deoxyheptonate aldolaseNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
UPhospho-2-dehydro-3-deoxyheptonate aldolase, Phe-sensitiveNot AvailableEscherichia coli (strain K12)
UCapsule biosynthesis proteinNot AvailableNeisseria meningitidis
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Amino Sugar MetabolismMetabolic
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)Disease
Tay-Sachs DiseaseDisease
Warburg EffectMetabolic
Sialuria or French Type SialuriaDisease
Primary hyperoxaluria II, PH2Disease
Fructose-1,6-diphosphatase deficiencyDisease
Fanconi-bickel syndromeDisease
Pyruvate MetabolismMetabolic
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke DiseaseDisease
Pyruvate kinase deficiencyDisease
Phosphoenolpyruvate carboxykinase deficiency 1 (PEPCK1)Disease
Triosephosphate isomeraseDisease
GlycolysisMetabolic
Leigh SyndromeDisease
Sialuria or French Type SialuriaDisease
G(M2)-Gangliosidosis: Variant B, Tay-sachs diseaseDisease
Glycogenosis, Type IA. Von gierke diseaseDisease
GluconeogenesisMetabolic
Pyruvate Dehydrogenase Complex DeficiencyDisease
Salla Disease/Infantile Sialic Acid Storage DiseaseDisease
Glycogenosis, Type VII. Tarui diseaseDisease
Glycogenosis, Type IBDisease
Glycogenosis, Type ICDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Naotaka Hamasaki, Hirotaka Kawamura, Norio Ohtsu, Ichiro Nakakoshi, Kikuo Ataka, Kiyosi Oomori, Masahiko Kouno, "Process for preparing monosodium phosphoenolpyruvate." U.S. Patent US4874882, issued October, 1984.

US4874882
General References
Not Available
External Links
Human Metabolome Database
HMDB00263
KEGG Compound
C00074
PubChem Compound
1005
PubChem Substance
46506098
ChemSpider
980
BindingDB
50366413
ChEBI
44897
ChEMBL
CHEMBL1235228
HET
PEP
Wikipedia
Phosphoenolpyruvate
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9135
Blood Brain Barrier+0.9346
Caco-2 permeable-0.7662
P-glycoprotein substrateNon-substrate0.7679
P-glycoprotein inhibitor INon-inhibitor0.8508
P-glycoprotein inhibitor IINon-inhibitor0.9478
Renal organic cation transporterNon-inhibitor0.9503
CYP450 2C9 substrateNon-substrate0.85
CYP450 2D6 substrateNon-substrate0.8598
CYP450 3A4 substrateNon-substrate0.6615
CYP450 1A2 substrateNon-inhibitor0.8775
CYP450 2C9 inhibitorNon-inhibitor0.8642
CYP450 2D6 inhibitorNon-inhibitor0.9013
CYP450 2C19 inhibitorNon-inhibitor0.8336
CYP450 3A4 inhibitorNon-inhibitor0.9346
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9688
Ames testNon AMES toxic0.8063
CarcinogenicityCarcinogens 0.5
BiodegradationNot ready biodegradable0.6059
Rat acute toxicity2.6225 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9624
hERG inhibition (predictor II)Non-inhibitor0.937
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0292-0962000000-44d3914b4e07e5c50e3f
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0292-0962000000-44d3914b4e07e5c50e3f
LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0udr-1900000000-9a4f5554af9a717d99c7
LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-000x-9200000000-6cdc15f3daa25fc41655
LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-001i-9100000000-39e22409d6d924a774f1
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-00xu-0912000000-ad1823470675975d5ff0
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0udi-0900000000-1f5b761ce5fa374b0f8e
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-9000000000-d279f0ca2accb130181f
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0002-0920000000-f084dccf78e11c8760d7
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-00lr-0911000000-7fa833698210746c838f
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-9000000000-62e28301f20b08971b78
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0udi-0900000000-25f970898112f7b89898
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0002-0930000000-58691b23d317c2418c33
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-00p0-0493110000-9d61bb13ab5261fdf9fd
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-004i-9100000000-db409b3cfa9ebabbcb58
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0a4j-5090000000-1ee56bc4866301d4bf2e
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0a4i-0090000000-bce08b01d44391bfecad
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-016r-7900000000-ffd3b8dcd65aaea26ac3
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-004i-9000000000-ceae3587b1e7d8b3da27
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-004i-9000000000-701a17330cd18255d625
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-004i-9000000000-a4178ce4951e2c3dba7b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-004i-9000000000-9d0421620a7aaa9ef33f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0k9i-1900000000-fb12ade375a7ac97f150
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-0f76-8900000000-7f57e6a8e72e5992cd88
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-000j-9300000000-c02bca019150d572b3bc
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-05bf-9200000000-73fa5ca52ecc17bac380
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-0079-9300000000-231346190165f44f28dc
1H NMR Spectrum1D NMRNot applicable
1H NMR Spectrum1D NMRNot applicable
13C NMR Spectrum1D NMRNot applicable
[1H,1H] 2D NMR Spectrum2D NMRNot applicable
[1H,13C] 2D NMR Spectrum2D NMRNot applicable

Taxonomy

Description
This 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 Class
Organic compounds
Class
Organic acids and derivatives
Sub Class
Organic phosphoric acids and derivatives
Direct Parent
Phosphate esters
Alternative Parents
Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
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
monocarboxylic acid, carboxyalkyl phosphate (CHEBI:44897 )

Targets

Kind
Protein
Organism
Shigella flexneri
Pharmacological action
Unknown
General Function
3-deoxy-8-phosphooctulonate synthase activity
Specific Function
Not Available
Gene Name
kdsA
Uniprot ID
P0A716
Uniprot Name
2-dehydro-3-deoxyphosphooctonate aldolase
Molecular Weight
30832.485 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Phosphopyruvate hydratase activity
Specific Function
Appears to have a function in striated muscle development and regeneration.
Gene Name
ENO3
Uniprot ID
P13929
Uniprot Name
Beta-enolase
Molecular Weight
46986.485 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Phosphoenolpyruvate carboxykinase (gtp) activity
Specific Function
Catalyzes the 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...
Gene Name
PCK1
Uniprot ID
P35558
Uniprot Name
Phosphoenolpyruvate carboxykinase, cytosolic [GTP]
Molecular Weight
69193.975 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Aquifex aeolicus (strain VF5)
Pharmacological action
Unknown
General Function
3-deoxy-8-phosphooctulonate synthase activity
Specific Function
Not Available
Gene Name
kdsA
Uniprot ID
O66496
Uniprot Name
2-dehydro-3-deoxyphosphooctonate aldolase
Molecular Weight
29734.17 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
Aldehyde-lyase activity
Specific Function
Catalyzes the condensation of phosphoenolpyruvate (PEP) and D-erythrose-4-phosphate (E4P) giving rise to 3-deoxy-D-arabino-heptulosonate-7-phosphate (DAHP).
Gene Name
aroF
Uniprot ID
Q9WYH8
Uniprot Name
Phospho-2-dehydro-3-deoxyheptonate aldolase
Molecular Weight
37377.805 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Identical protein binding
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
aroG
Uniprot ID
P0AB91
Uniprot Name
Phospho-2-dehydro-3-deoxyheptonate aldolase, Phe-sensitive
Molecular Weight
38009.165 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Neisseria meningitidis
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Not Available
Gene Name
synC
Uniprot ID
Q57265
Uniprot Name
Capsule biosynthesis protein
Molecular Weight
38347.39 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, a...
Gene Name
SLCO2A1
Uniprot ID
Q92959
Uniprot Name
Solute carrier organic anion transporter family member 2A1
Molecular Weight
70043.33 Da
References
  1. Chan BS, Endo S, Kanai N, Schuster VL: Identification of lactate as a driving force for prostanoid transport by prostaglandin transporter PGT. Am J Physiol Renal Physiol. 2002 Jun;282(6):F1097-102. [PubMed:11997326 ]
Drug created on June 13, 2005 07:24 / Updated on September 01, 2017 10:44