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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:50 UTC
HMDB IDHMDB01494
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcetylphosphate
DescriptionAcetylphosphate or actyl phosphate is a compound involved in taurine and hypotaurine metabolism as well as pyruvate metabolism. 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. It is also an intermediate in pyruvate metabolism. It is generated from pyruvate and the formation is catalyzed by pyruvate oxidase (EC:1.2.3.3).
Structure
Thumb
Synonyms
ValueSource
Acetyl phosphateHMDB
Acetyl-PHMDB
Chemical FormulaC2H5O5P
Average Molecular Weight140.0319
Monoisotopic Molecular Weight139.987459782
IUPAC Name(acetyloxy)phosphonic acid
Traditional Nameacetylphosphate
CAS Registry Number590-54-5
SMILES
CC(=O)OP(O)(O)=O
InChI Identifier
InChI=1S/C2H5O5P/c1-2(3)7-8(4,5)6/h1H3,(H2,4,5,6)
InChI KeyInChIKey=LIPOUNRJVLNBCD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as organic phosphoric acids. These are organic compounds containing phosphoric acid, with the general structure OP(O)(=O)O.
KingdomOrganic compounds
Super ClassOrganophosphorus compounds
ClassOrganic phosphoric acids and derivatives
Sub ClassOrganic phosphoric acids
Direct ParentOrganic phosphoric acids
Alternative Parents
Substituents
  • Organic phosphate
  • Acetate salt
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Energy source
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility17.8 mg/mLALOGPS
logP-0.92ALOGPS
logP-0.88ChemAxon
logS-0.9ALOGPS
pKa (Strongest Acidic)1.24ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.8 m3·mol-1ChemAxon
Polarizability9.87 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-9100000000-69d8c7734c01156379c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-2f22bf3e8b4d114a56d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ufr-9000000000-55ffd7f2d3597806d481View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Leigh SyndromeSMP00196Not Available
Primary hyperoxaluria II, PH2SMP00558Not Available
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)SMP00334Not Available
Pyruvate Dehydrogenase Complex DeficiencySMP00212Not Available
Pyruvate kinase deficiencySMP00559Not Available
Pyruvate MetabolismSMP00060map00620
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022653
KNApSAcK IDNot Available
Chemspider ID181
KEGG Compound IDC00227
BioCyc IDACETYL-P
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01494
Metagene LinkHMDB01494
METLIN ID6278
PubChem Compound186
PDB IDUVW
ChEBI ID15350
References
Synthesis ReferenceCostakel, O.; Kitzoulesco, I. The possibility of acetylphosphate synthesis in cancerous and noncancerous human serum at pH 4. Rev. sci. Med., Acad. rep. populaire Roumaine (1960), 5 7-10.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Libeer JC, Scharpe SL, Verkerk RM, Deprettere AJ, Schepens PJ: Simultaneous determination of p-aminobenzoic acid, acetyl-p-aminobenzoic acid and p-aminohippuric acid in serum and urine by capillary gas chromatography with use of a nitrogen-phosphorus detector. Clin Chim Acta. 1981 Sep 10;115(2):119-23. [6974621 ]
  2. Dowling TC, Frye RF, Zemaitis MA: Simultaneous determination of p-aminohippuric acid, acetyl-p-aminohippuric acid and iothalamate in human plasma and urine by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl. 1998 Sep 25;716(1-2):305-13. [9824245 ]

Enzymes

General function:
Involved in acylphosphatase activity
Specific function:
Its physiological role is not yet clear.
Gene Name:
ACYP2
Uniprot ID:
P14621
Molecular weight:
11139.52
Reactions
Acetylphosphate + Water → Acetic acid + Phosphoric aciddetails
General function:
Involved in acylphosphatase activity
Specific function:
Its physiological role is not yet clear.
Gene Name:
ACYP1
Uniprot ID:
P07311
Molecular weight:
11260.84
Reactions
Acetylphosphate + Water → Acetic acid + Phosphoric aciddetails