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Identification
NamePhosphoenolpyruvate
Accession NumberDB01819  (EXPT02550)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNII545YL308OW
CAS number138-08-9
WeightAverage: 168.042
Monoisotopic: 167.982374404
Chemical FormulaC3H5O6P
InChI KeyInChIKey=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
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
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
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 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 )
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
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-1zp7000000-44d3914b4e07e5c50e3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-5z00000000-9a4f5554af9a717d99c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-z700000000-6cdc15f3daa25fc41655View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-z400000000-39e22409d6d924a774f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0z48100000-ad1823470675975d5ff0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0z00000000-1f5b761ce5fa374b0f8eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-z200000000-d279f0ca2accb130181fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0za1000000-f084dccf78e11c8760d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0z76100000-7fa833698210746c838fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-z000000000-62e28301f20b08971b78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0z00000000-25f970898112f7b89898View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0zb1000000-58691b23d317c2418c33View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0gze741110-9d61bb13ab5261fdf9fdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-z400000000-db409b3cfa9ebabbcb58View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-m3z0000000-1ee56bc4866301d4bf2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00z0000000-bce08b01d44391bfecadView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-rz00000000-ffd3b8dcd65aaea26ac3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-z000000000-ceae3587b1e7d8b3da27View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-z000000000-701a17330cd18255d625View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-z000000000-a4178ce4951e2c3dba7bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-z000000000-9d0421620a7aaa9ef33fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-4z00000000-fb12ade375a7ac97f150View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-yz00000000-7f57e6a8e72e5992cd88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-ze00000000-c02bca019150d572b3bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-z900000000-73fa5ca52ecc17bac380View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-zb00000000-231346190165f44f28dcView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot 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 ReferencesNot 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