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Identification
NamePhosphoenolpyruvate
Accession NumberDB01819  (EXPT02550)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number138-08-9
WeightAverage: 168.042
Monoisotopic: 167.982374404
Chemical FormulaC3H5O6P
InChI KeyDTBNBXWJWCWCIK-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
Taxonomy
DescriptionThis compound 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 ClassOrganophosphorus compounds
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentPhosphate esters
Alternative Parents
Substituents
  • Phosphoric acid ester
  • Organic phosphate
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Phosphoenolpyruvate carboxykinase deficiency 1 (PEPCK1)DiseaseSMP00560
Fanconi-bickel syndromeDiseaseSMP00572
Glycogenosis, Type ICDiseaseSMP00574
GluconeogenesisMetabolicSMP00128
Glycogenosis, Type IBDiseaseSMP00573
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke DiseaseDiseaseSMP00374
Triosephosphate isomeraseDiseaseSMP00563
GlycolysisMetabolicSMP00040
Glycogenosis, Type VII. Tarui diseaseDiseaseSMP00531
Fructose-1,6-diphosphatase deficiencyDiseaseSMP00562
Glycogenosis, Type IA. Von gierke diseaseDiseaseSMP00581
Tay-Sachs DiseaseDiseaseSMP00390
Sialuria or French Type SialuriaDiseaseSMP00217
Salla Disease/Infantile Sialic Acid Storage DiseaseDiseaseSMP00240
Amino Sugar MetabolismMetabolicSMP00045
Sialuria or French Type SialuriaDiseaseSMP00216
G(M2)-Gangliosidosis: Variant B, Tay-sachs diseaseDiseaseSMP00534
Pyruvate MetabolismMetabolicSMP00060
Pyruvate Dehydrogenase Complex DeficiencyDiseaseSMP00212
Pyruvate kinase deficiencyDiseaseSMP00559
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)DiseaseSMP00334
Primary hyperoxaluria II, PH2DiseaseSMP00558
Warburg EffectMetabolicSMP00654
Leigh SyndromeDiseaseSMP00196
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.8642
CYP450 2D6 substrateNon-inhibitor0.9013
CYP450 2C19 substrateNon-inhibitor0.8336
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
Spectra
Mass Spec (NIST)Not Available
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
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 ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. 2-dehydro-3-deoxyphosphooctonate aldolase

Kind: protein

Organism: Shigella flexneri

Pharmacological action: unknown

Components

Name UniProt ID Details
2-dehydro-3-deoxyphosphooctonate aldolase P0A716 Details

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
  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

2. Beta-enolase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Beta-enolase P13929 Details

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
  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
  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

3. Phosphoenolpyruvate carboxykinase, cytosolic [GTP]

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Phosphoenolpyruvate carboxykinase, cytosolic [GTP] P35558 Details

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
  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

4. 2-dehydro-3-deoxyphosphooctonate aldolase

Kind: protein

Organism: Aquifex aeolicus (strain VF5)

Pharmacological action: unknown

Components

Name UniProt ID Details
2-dehydro-3-deoxyphosphooctonate aldolase O66496 Details

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
  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

5. Phospho-2-dehydro-3-deoxyheptonate aldolase

Kind: protein

Organism: Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)

Pharmacological action: unknown

Components

Name UniProt ID Details
Phospho-2-dehydro-3-deoxyheptonate aldolase Q9WYH8 Details

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
  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

6. Phospho-2-dehydro-3-deoxyheptonate aldolase, Phe-sensitive

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Phospho-2-dehydro-3-deoxyheptonate aldolase, Phe-sensitive P0AB91 Details

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
  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

7. Capsule biosynthesis protein

Kind: protein

Organism: Neisseria meningitidis

Pharmacological action: unknown

Components

Name UniProt ID Details
Capsule biosynthesis protein Q57265 Details

Transporters

1. Solute carrier organic anion transporter family member 2A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier organic anion transporter family member 2A1 Q92959 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:16