Identification
- Generic Name
- Phosphoenolpyruvate
- DrugBank Accession Number
- DB01819
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Phosphoenolpyruvate (DB01819)
- Weight
- Average: 168.042
Monoisotopic: 167.982374404 - Chemical Formula
- C3H5O6P
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism U2-dehydro-3-deoxyphosphooctonate aldolase Not Available Shigella flexneri UBeta-enolase Not Available Humans UPhosphoenolpyruvate carboxykinase, cytosolic [GTP] Not Available Humans U2-dehydro-3-deoxyphosphooctonate aldolase Not Available Aquifex aeolicus (strain VF5) UPhospho-2-dehydro-3-deoxyheptonate aldolase Not Available Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099) UPhospho-2-dehydro-3-deoxyheptonate aldolase, Phe-sensitive Not Available Escherichia coli (strain K12) UCapsule biosynthesis protein Not Available Neisseria 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke Disease Disease Fructose-1,6-diphosphatase Deficiency Disease Triosephosphate Isomerase Disease Fanconi-Bickel Syndrome Disease Warburg Effect Metabolic Glycolysis Metabolic Amino Sugar Metabolism Metabolic Glycogenosis, Type VII. Tarui Disease Disease G(M2)-Gangliosidosis: Variant B, Tay-Sachs Disease Disease Pyruvate Kinase Deficiency Disease Phosphoenolpyruvate Carboxykinase Deficiency 1 (PEPCK1) Disease Glycogenosis, Type IB Disease Pyruvate Metabolism Metabolic Gluconeogenesis Metabolic Leigh Syndrome Disease Pyruvate Dehydrogenase Complex Deficiency Disease Sialuria or French Type Sialuria Disease Sialuria or French Type Sialuria Disease Salla Disease/Infantile Sialic Acid Storage Disease Disease Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency) Disease Tay-Sachs Disease Disease Primary Hyperoxaluria II, PH2 Disease Glycogenosis, Type IC Disease Glycogenosis, Type IA. Von Gierke Disease Disease - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Organic phosphoric acids and derivatives
- Sub Class
- Phosphate esters
- Direct Parent
- Phosphate esters
- Alternative Parents
- Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound / Organooxygen compound / Phosphoric acid ester
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- monocarboxylic acid, carboxyalkyl phosphate (CHEBI:44897)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 545YL308OW
- CAS number
- 138-08-9
- 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
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
- HMDB0000263
- KEGG Compound
- C00074
- PubChem Compound
- 1005
- PubChem Substance
- 46506098
- ChemSpider
- 980
- BindingDB
- 50366413
- ChEBI
- 44897
- ChEMBL
- CHEMBL1235228
- ZINC
- ZINC000003870145
- PDBe Ligand
- PEP
- Wikipedia
- Phosphoenolpyruvate
- PDB Entries
- 1fwn / 1fws / 1fwt / 1fww / 1fxq / 1g7u / 1hfb / 1jcy / 1kfl / 1khf … show 103 more
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
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
Property Value Source Water Solubility 13.2 mg/mL ALOGPS logP -1.2 ALOGPS logP -0.64 Chemaxon logS -1.1 ALOGPS pKa (Strongest Acidic) 0.76 Chemaxon Physiological Charge -3 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 104.06 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 30.13 m3·mol-1 Chemaxon Polarizability 11.57 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.8642 CYP450 2D6 inhibitor Non-inhibitor 0.9013 CYP450 2C19 inhibitor Non-inhibitor 0.8336 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 131.2146368 predictedDarkChem Lite v0.1.0 [M-H]- 133.3977368 predictedDarkChem Lite v0.1.0 [M-H]- 131.7620368 predictedDarkChem Lite v0.1.0 [M-H]- 118.22604 predictedDeepCCS 1.0 (2019) [M+H]+ 121.805046 predictedDeepCCS 1.0 (2019) [M+Na]+ 130.58281 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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
- 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
- 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
- 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
- Humans
- 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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52