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Identification
NamePhosphoenolpyruvate
Accession NumberDB01819  (EXPT02550)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot 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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganophosphorus Compounds
ClassOrganic Phosphoric Acids and Derivatives
SubclassOrganophosphate Esters
Direct parentOrganophosphate Esters
Alternative parentsOrganic Phosphoric Acids; Enones; Polyamines; Enolates; Carboxylic Acids
Substituentsenone; enolate; polyamine; carboxylic acid; carboxylic acid derivative
Classification descriptionThis compound belongs to the organophosphate esters. These are organic compounds containing phosphoric acid ester functional group.
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
GlycolysisMetabolicSMP00040
Glycogenosis, Type VII. Tarui diseaseDiseaseSMP00531
Fructose-1,6-diphosphatase deficiencyDiseaseSMP00562
Glycogenosis, Type IA. Von gierke diseaseDiseaseSMP00581
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke DiseaseDiseaseSMP00374
Triosephosphate isomeraseDiseaseSMP00563
Pyruvate MetabolismMetabolicSMP00060
Pyruvate Dehydrogenase Complex DeficiencyDiseaseSMP00212
Salla Disease/Infantile Sialic Acid Storage DiseaseDiseaseSMP00240
Pyruvate kinase deficiencyDiseaseSMP00559
Tay-Sachs DiseaseDiseaseSMP00390
Sjogren Larsson SyndromeDiseaseSMP00217
Leigh SyndromeDiseaseSMP00196
Amino Sugar MetabolismMetabolicSMP00045
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)DiseaseSMP00334
Sialuria or French Type SialuriaDiseaseSMP00216
G(M2)-Gangliosidosis: Variant B, Tay-sachs diseaseDiseaseSMP00534
Primary hyperoxaluria II, PH2DiseaseSMP00558
Warburg EffectMetabolicSMP00654
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption - 0.9135
Blood Brain Barrier + 0.9346
Caco-2 permeable - 0.7662
P-glycoprotein substrate Non-substrate 0.7679
P-glycoprotein inhibitor I Non-inhibitor 0.8508
P-glycoprotein inhibitor II Non-inhibitor 0.9478
Renal organic cation transporter Non-inhibitor 0.9503
CYP450 2C9 substrate Non-substrate 0.85
CYP450 2D6 substrate Non-substrate 0.8598
CYP450 3A4 substrate Non-substrate 0.6615
CYP450 1A2 substrate Non-inhibitor 0.8775
CYP450 2C9 substrate Non-inhibitor 0.8642
CYP450 2D6 substrate Non-inhibitor 0.9013
CYP450 2C19 substrate Non-inhibitor 0.8336
CYP450 3A4 substrate Non-inhibitor 0.9346
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9688
Ames test Non AMES toxic 0.8063
Carcinogenicity Carcinogens 0.5
Biodegradation Not ready biodegradable 0.6059
Rat acute toxicity 2.6225 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9624
hERG inhibition (predictor II) Non-inhibitor 0.937
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility13.2ALOGPS
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
Spectra
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
ResourceLink
KEGG CompoundC00074
PubChem Compound1005
PubChem Substance46506098
ChemSpider980
ChEBI26055
ChEMBL
HETPEP
WikipediaPhosphoenolpyruvate
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. 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

2. 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

3. 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

4. Capsule biosynthesis protein

Kind: protein

Organism: Neisseria meningitidis

Pharmacological action: unknown

Components

Name UniProt ID Details
Capsule biosynthesis protein Q57265 Details

5. 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

6. 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

7. 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

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