Common NamePhosphoenolpyruvate
DescriptionPhosphoenolpyruvate (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 FormulaC3H5O6P
Average Mass168.04200
Monoisotopic Mass167.98237
IUPAC Name2-(phosphonooxy)prop-2-enoic acid
Traditional NamePhosphoenolpyruvate
CAS Registry Number0138-08-09
SMILESC=C(OP(=O)([O-])[O-])C(=O)[O-]
InChI IdentifierInChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)
InChI KeyDTBNBXWJWCWCIK-UHFFFAOYSA-N
CHEBI IDCHEBI:58702
HMDB IDHMDB0000263
Pathways
NameSMPDB/PathBank
Pyruvate metabolism
Glycolysis
Amino Sugar Metabolism
Gluconeogenesis
Leigh Syndrome
Pyruvate Dehydrogenase Complex Deficiency
Sialuria or French Type Sialuria
Salla Disease/Infantile Sialic Acid Storage Disease
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke Disease
Tay-Sachs Disease
Glycogenosis, Type VII. Tarui disease
G(M2)-Gangliosidosis: Variant B, Tay-sachs disease
Primary hyperoxaluria II, PH2
Pyruvate kinase deficiency
Phosphoenolpyruvate carboxykinase deficiency 1 (PEPCK1)
Fructose-1,6-diphosphatase deficiency
Triosephosphate isomerase
Fanconi-bickel syndrome
Glycogenosis, Type IB
Glycogenosis, Type IC
Glycogenosis, Type IA. Von gierke disease
Warburg Effect
StateSolid
Water Solubility1.32e+01 g/l
logP-1.22
logS-1.10
pKa (Strongest Acidic)0.76
pKa (Strongest Basic)Not Available
Hydrogen Acceptor Count5
Hydrogen Donor Count3
Polar Surface Area104.06 Ų
Rotatable Bond Count3
Physiological Charge-3
Formal Charge0
Refractivity30.13 m³·mol⁻¹
Polarizability11.69

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