Showing Metabocard for phosphoenolpyruvate (BASm0003641)
Common Name | Phosphoenolpyruvate |
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Description | Phosphoenolpyruvate (PEP) is an important chemical compound in biochemistry. It has a high energy phosphate bond, and is involved in glycolysis and gluconeogenesis. In glycolysis, PEP is formed by the action of the enzyme enolase on 2-phosphoglycerate. Metabolism of PEP to pyruvate by pyruvate kinase (PK) generates 1 molecule of adenosine triphosphate (ATP) via substrate-level phosphorylation. ATP is one of the major currencies of chemical energy within cells. In gluconeogenesis, PEP is formed from the decarboxylation of oxaloacetate and hydrolysis of 1 guanosine triphosphate molecule. This reaction is catalyzed by the enzyme phosphoenolpyruvate carboxykinase (PEPCK). This reaction is a rate-limiting step in gluconeogenesis. (wikipedia). |
Structure | |
Molecular Formula | C3H5O6P |
Average Mass | 168.04200 |
Monoisotopic Mass | 167.98237 |
IUPAC Name | 2-(phosphonooxy)prop-2-enoic acid |
Traditional Name | Phosphoenolpyruvate |
CAS Registry Number | 0138-08-09 |
SMILES | C=C(OP(=O)([O-])[O-])C(=O)[O-] |
InChI Identifier | InChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8) |
InChI Key | DTBNBXWJWCWCIK-UHFFFAOYSA-N |
CHEBI ID | CHEBI:58702 |
HMDB ID | HMDB0000263 |
Pathways | |
State | Solid |
Water Solubility | 1.32e+01 g/l |
logP | -1.22 |
logS | -1.10 |
pKa (Strongest Acidic) | 0.76 |
pKa (Strongest Basic) | Not Available |
Hydrogen Acceptor Count | 5 |
Hydrogen Donor Count | 3 |
Polar Surface Area | 104.06 Ų |
Rotatable Bond Count | 3 |
Physiological Charge | -3 |
Formal Charge | 0 |
Refractivity | 30.13 m³·mol⁻¹ |
Polarizability | 11.69 |