Record Information
Version2.0
Creation Date2012-05-31 13:53:34 -0600
Update Date2015-09-13 12:56:11 -0600
Secondary Accession Numbers
  • ECMDB01494
Identification
Name:Acetylphosphate
Description:Acetylphosphate is an intermediate in taurine and hypotaurine 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 intermediate in pyruvate metabolism. It is generated from pyruvate and the formation is catalyzed by pyruvate oxidase (EC:1.2.3.3). (KEGG)
Structure
Thumb
Synonyms:
  • Acetyl phosphate
  • Acetyl phosphoric acid
  • Acetyl-P
  • Acetylphosphate
  • Acetylphosphoric acid
Chemical Formula:C2H5O5P
Weight:Average: 140.0319
Monoisotopic: 139.987459782
InChI Key:LIPOUNRJVLNBCD-UHFFFAOYSA-N
InChI:InChI=1S/C2H5O5P/c1-2(3)7-8(4,5)6/h1H3,(H2,4,5,6)
CAS number:590-54-5
IUPAC Name:(acetyloxy)phosphonic acid
Traditional IUPAC Name:acetylphosphate
SMILES:CC(=O)OP(O)(O)=O
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentAcyl monophosphates
Alternative Parents
Substituents
  • Acyl monophosphate
  • Acetate salt
  • Carboxylic acid salt
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Acetate metabolismPW002090 Pw002090Pw002090 greyscalePw002090 simple
Propanoate metabolismPW000940 Pw000940Pw000940 greyscalePw000940 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
1070± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
1050± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
1560± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-0002-9000000000-cfae3a8437091232f5d7View in MoNA
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9100000000-9815fa392fb818a6fab2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-f9f47252b65adfe6b7abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000w-9000000000-aee29878b0aaf31375caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9200000000-30c93bbfd1e1c181a0bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-3f8df70a36020543d1d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5ee765f8651dddb71d5cView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • 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. Pubmed: 9824245
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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. Pubmed: 6974621
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Costakel, 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)
External Links:
ResourceLink
CHEBI ID15350
HMDB IDHMDB01494
Pubchem Compound ID186
Kegg IDC00227
ChemSpider ID181
Wikipedia IDNot Available
BioCyc IDACETYL-P
EcoCyc IDACETYL-P
Ligand ExpoUVW

Enzymes

General function:
Involved in kinase activity
Specific function:
Involved in the activation of acetate to acetyl CoA and the secretion of acetate. During anaerobic growth of the organism, this enzyme is also involved in the synthesis of most of the ATP formed catabolically
Gene Name:
ackA
Uniprot ID:
P0A6A3
Molecular weight:
43290
Reactions
ATP + acetate = ADP + acetyl phosphate.
ATP + propanoate = ADP + propanoyl phosphate.
General function:
Involved in phosphate acetyltransferase activity
Specific function:
Acetyl-CoA + phosphate = CoA + acetyl phosphate
Gene Name:
pta
Uniprot ID:
P0A9M8
Molecular weight:
77171
Reactions
Acetyl-CoA + phosphate = CoA + acetyl phosphate.
General function:
Involved in acylphosphatase activity
Specific function:
An acylphosphate + H(2)O = a carboxylate + phosphate
Gene Name:
yccX
Uniprot ID:
P0AB65
Molecular weight:
10300
Reactions
An acylphosphate + H(2)O = a carboxylate + phosphate.
General function:
Involved in kinase activity
Specific function:
ATP + propanoate = ADP + propanoyl phosphate
Gene Name:
tdcD
Uniprot ID:
P11868
Molecular weight:
43384
Reactions
ATP + propanoate = ADP + propanoyl phosphate.
ATP + acetate = ADP + acetyl phosphate.
General function:
Involved in ATP binding
Specific function:
Catalyzes two reactions:the first one is the production of beta-formyl glycinamide ribonucleotide (GAR) from formate, ATP and beta GAR; the second, a side reaction, is the production of acetyl phosphate and ADP from acetate and ATP
Gene Name:
purT
Uniprot ID:
P33221
Molecular weight:
42433
Reactions
Formate + ATP + 5'-phospho-ribosylglycinamide = 5'-phosphoribosyl-N-formylglycinamide + ADP + diphosphate.
General function:
Involved in transferase activity, transferring acyl groups
Specific function:
Specific function unknown
Gene Name:
eutD
Uniprot ID:
P77218
Molecular weight:
36066