Phosphoenolpyruvate
Basic information
- CAS
138-08-9- Standard SMILES
C=C(OP(=O)(O)O)C(=O)O- InChIKey
DTBNBXWJWCWCIK-UHFFFAOYSA-N- Molecular formula
- C3H5O6P
- Average molar mass
- 168.04 g/mol
- Monoisotopic mass
- 167.98237487
Overview
Phosphoenolpyruvic acid is a monocarboxylic acid that is acrylic acid substituted by a phosphonooxy group at position 2. It is a metabolic intermediate in pathways like glycolysis and gluconeogenesis. It has a role as a fundamental metabolite. It is a monocarboxylic acid and a carboxyalkyl phosphate. It is functionally related to an acrylic acid. It is a conjugate acid of a phosphoenolpyruvate and a phosphonatoenolpyruvate.
Names & identifiers
- Preferred name
- Phosphoenolpyruvate
- IUPAC
- 2-phosphonooxyprop-2-enoic acid
- English name
- 2-dihydroxyphosphinoyloxyacrylic acid
- Molecular formula
- C3H5O6P
- Molecular weight
- 168.04
Names & synonyms
phosphoenolpyruvatePhosphoenolpyruvic acid138-08-92-(phosphonooxy)prop-2-enoic acid2-Phosphonooxyprop-2-enoic acid2-(phosphonooxy)-2-propenoic acid2-(phosphonooxy)-2-propenoate545YL308OWCHEBI:44897DTXSID808617971-carboxyethenoxy(oxonio)phosphinate2-(hydroxy(oxonio)phosphoryl)oxyprop-2-enoate
Show more names
PEP【phosphate】2-PhosphoenolpyruvatePhosphoenolpyruvicacid2-Phosphonooxypropenoic acid2-(Phosphonooxy)acrylic acidGlucosamine Hydrochloride Impurity 262-dihydroxyphosphinoyloxyacrylic acid2-(Dihydroxyphosphinyloxy)acrylic acid
CHEBI:18021DTXSID00223277RefChem:173566DTXCID00145768DTXCID90197579200-804-32-Propenoic acid, 2-(phosphonooxy)-Phosphopyruvic acid
Properties
Computed structural properties
- XLogP
- -1.1
- Topological polar surface area
- 104 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 201
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Other Biomolecules
DrugsPharmaceuticals -> Listed in ZINC15
Physical DescriptionSolid
Collision Cross Section
138 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
164.28 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
131 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine]
163.7 Ų [M-H]-
Physicochemical properties
- Boiling point
- 466.7 · 466.7±47.0 °C(Predicted)
- Density
- 1.804 · 1.804±0.06 g/cm3(Predicted)
- pka
- 1.39 · 1.39±0.10(Predicted)
- FDA UNII
- 545 YL308OW · 545YL308OW
- EPA Substance Registry System
- Phosphopyruvic acid (138-08-9)
- TSCA
- TSCA listed
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationChemical: 2-Propenoic acid, 2-(phosphonooxy)-
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Safety data
- tsca
- TSCA listed
Chemistry & industry
Pharmacology
Tissue LocationsPlacenta
Cellular LocationsCytoplasm
Metabolite PathwaysAmino Sugar Metabolism
Uses & manufacturing
General Manufacturing Information2-Propenoic acid, 2-(phosphonooxy)-: INACTIVE
Applications
UsesPhosphoenolpyruvic acid (Phosphoenolpyruvate) is a glycolysis metabolite with a high-energy phosphate group. Phosphoenolpyruvic acid is involved in glycolysis and gluconeogenesis, and used as energy source to produce ATP, under the energy-limited conditions. Phosphoenolpyruvic acid also exhibits cytoprotective and anti-oxidative properties[1].
Upstream & downstream products
Upstream raw materials
Related reactions
16 records
Compound notes
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