Common NameAcetyl phosphate
DescriptionAcetylphosphate, also known as acetyl-p, belongs to the class of organic compounds known as acyl monophosphates. These are organic compounds containing a monophosphate linked to an acyl group. They have the general structure R-CO-P(O)(O)OH, R=H or organyl. Since acetylphosphate synthesis is known to depend on cholinesterase activity, pseudocholinesterase was assumed to participate to a small extent in acetylphosphate synthesis by cancerous serum. It is also an intermediate in pyruvate metabolism. Acetylphosphate is a drug. Acetylphosphate exists in all living organisms, ranging from bacteria to humans. Acetylphosphate can be converted into acetic acid; which is mediated by the enzyme acylphosphatase-1. It is generated from pyruvate and the formation is catalyzed by pyruvate oxidase (EC:1.2.3.3). In humans, acetylphosphate is involved in the metabolic disorder called the pyruvate dehydrogenase complex deficiency pathway. It is generated from sulfoacetaldehyde, converted to acetyl-CoA and acetate via phosphate acetyltransferase (EC:2.3.1.8) and acetate kinase (EC:2.7.2.1) respectively. Acetylphosphate or actyl phosphate is a compound involved in taurine and hypotaurine metabolism as well as pyruvate metabolism. Cancerous serum produced 37% less acetylphosphate than normal serum.
Structure
Molecular FormulaC2H5O5P
Average Mass140.03190
Monoisotopic Mass139.98746
IUPAC Name(acetyloxy)phosphonic acid
Traditional NameAcetyloxyphosphonic acid
CAS Registry Number590-54-5
SMILESCC(=O)OP(=O)([O-])[O-]
InChI IdentifierInChI=1S/C2H5O5P/c1-2(3)7-8(4,5)6/h1H3,(H2,4,5,6)
InChI KeyLIPOUNRJVLNBCD-UHFFFAOYSA-N
CHEBI IDCHEBI:22191
HMDB IDHMDB0001494
Pathways
NameSMPDB/PathBank
Pyruvate metabolism
Leigh Syndrome
Pyruvate Dehydrogenase Complex Deficiency
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)
Primary hyperoxaluria II, PH2
Pyruvate kinase deficiency
StateSolid
Water Solubility1.78e+01 g/l
logP-0.92
logS-0.90
pKa (Strongest Acidic)1.24
pKa (Strongest Basic)-7.39
Hydrogen Acceptor Count4
Hydrogen Donor Count2
Polar Surface Area83.83 Ų
Rotatable Bond Count2
Physiological Charge-2
Formal Charge0
Refractivity23.80 m³·mol⁻¹
Polarizability9.79

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