2.02012-05-31 13:53:34 -06002015-09-13 12:56:11 -0600ECMDB01494M2MDB000402AcetylphosphateAcetylphosphate 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)Acetyl phosphateAcetyl phosphoric acidAcetyl-PAcetylphosphateAcetylphosphoric acidC2H5O5P140.0319139.987459782(acetyloxy)phosphonic acidacetylphosphate590-54-5CC(=O)OP(O)(O)=OInChI=1S/C2H5O5P/c1-2(3)7-8(4,5)6/h1H3,(H2,4,5,6)LIPOUNRJVLNBCD-UHFFFAOYSA-NSolidCytosollogp-0.92logs-0.90solubility1.78e+01 g/llogp-0.88pka_strongest_acidic1.24pka_strongest_basic-7.4iupac(acetyloxy)phosphonic acidaverage_mass140.0319mono_mass139.987459782smilesCC(=O)OP(O)(O)=OformulaC2H5O5PinchiInChI=1S/C2H5O5P/c1-2(3)7-8(4,5)6/h1H3,(H2,4,5,6)inchikeyLIPOUNRJVLNBCD-UHFFFAOYSA-Npolar_surface_area83.83refractivity23.8polarizability9.87rotatable_bond_count2acceptor_count4donor_count2physiological_charge-2formal_charge0Reductive carboxylate cycle (CO2 fixation)ec00720Pyruvate metabolismec00620Methane metabolismec00680Propanoate metabolism
Starting from L-threonine, this compound is deaminated through a threonine deaminase resulting in a hydrogen ion, a water molecule and a (2z)-2-aminobut-2-enoate. The latter compound then isomerizes to a 2-iminobutanoate, This compound then reacts spontaneously with hydrogen ion and a water molecule resulting in a ammonium and a 2-Ketobutyric acid. The latter compound interacts with CoA through a pyruvate formate-lyase / 2-ketobutyrate formate-lyase resulting in a formic acid and a propionyl-CoA.
Propionyl-CoA can then be processed either into a 2-methylcitric acid or into a propanoyl phosphate.
Propionyl-CoA interacts with oxalacetic acid and a water molecule through a 2-methylcitrate synthase resulting in a hydrogen ion, a CoA and a 2-Methylcitric acid.The latter compound is dehydrated through a 2-methylcitrate dehydratase resulting in a water molecule and cis-2-methylaconitate. The latter compound is then dehydrated by a
bifunctional aconitate hydratase 2 and 2-methylisocitrate dehydratase resulting in a water molecule and methylisocitric acid. The latter compound is then processed by 2-methylisocitrate lyase resulting in a release of succinic acid and pyruvic acid.
Succinic acid can then interact with a propionyl-CoA through a propionyl-CoA:succinate CoA transferase resulting in a propionic acid and a succinyl CoA. Succinyl-CoA is then isomerized through a methylmalonyl-CoA mutase resulting in a methylmalonyl-CoA. This compound is then decarboxylated through a methylmalonyl-CoA decarboxylase resulting in a release of Carbon dioxide and Propionyl-CoA.
ropionyl-CoA interacts with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate.
Propionyl-CoA can react with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. The latter compound is then dephosphorylated through a ADP driven acetate kinase/propionate kinase protein complex resulting in an ATP and Propionic acid.
Propionic acid can be processed by a reaction with CoA through a ATP-driven propionyl-CoA synthetase resulting in a pyrophosphate, an AMP and a propionyl-CoA.PW000940ec00640MetabolicTaurine and hypotaurine metabolismec00430Microbial metabolism in diverse environmentsec01120Metabolic pathwayseco01100Acetate metabolismThe acetate biosynthesis starts with acetyl-CoA reacting with phosphate through a phosphate acetyltransferase resulting in the release of a coenzyme A and an acetyl phosphate. The latter compound in turn reacts with ADP through an acetate kinase resulting in the release of an ATP and an acetate. The acetate reacts with ATP and coenzyme A through an acetyl-CoA synthase resulting in the release of a diphosphate, an AMP and an acetyl-CoA.
Acetyl-CoA can be biosynthesized by acetoacetate reacting with an acetyl-CoA through an acetoacetyl-CoA transferase resulting in the release of an acetate and an acetoacetyl-CoA. The acetoacetyl-CoA reacts with an acetyl-CoA acetyltransferase resulting in the release of an coenzyme A and 2 acetyl-CoAPW002090Metabolicacetate formation from acetyl-CoA IPWY0-1312mixed acid fermentationFERMENTATION-PWYSpecdb::CMs8026Specdb::CMs174705Specdb::NmrOneD1719Specdb::NmrOneD147920Specdb::NmrOneD147921Specdb::NmrOneD147922Specdb::NmrOneD147923Specdb::NmrOneD147924Specdb::NmrOneD147925Specdb::NmrOneD147926Specdb::NmrOneD147927Specdb::NmrOneD147928Specdb::NmrOneD147929Specdb::NmrOneD147930Specdb::NmrOneD147931Specdb::NmrOneD147932Specdb::NmrOneD147933Specdb::NmrOneD147934Specdb::NmrOneD147935Specdb::NmrOneD147936Specdb::NmrOneD147937Specdb::NmrOneD147938Specdb::NmrOneD147939Specdb::MsMs1613Specdb::MsMs1614Specdb::MsMs1615Specdb::MsMs257304Specdb::MsMs257305Specdb::MsMs257306Specdb::MsMs277242Specdb::MsMs277243Specdb::MsMs277244Specdb::MsMs2364808Specdb::MsMs2364809Specdb::MsMs2364810Specdb::MsMs2597500Specdb::MsMs2597501Specdb::MsMs2597502Specdb::NmrTwoD1077Specdb::NmrTwoD1658HMDB01494186181C0022715350ACETYL-PUVWKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Winder, 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 80:2939-2948.18331064Bennett, 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 5:593-599.19561621Libeer 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):119-23.6974621Dowling 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):305-13.9824245Costakel, 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.http://hmdb.ca/system/metabolites/msds/000/001/356/original/HMDB01494.pdf?1358463422Acetate kinaseP0A6A3ACKA_ECOLIackAhttp://ecmdb.ca/proteins/P0A6A3.xmlPhosphate acetyltransferaseP0A9M8PTA_ECOLIptahttp://ecmdb.ca/proteins/P0A9M8.xmlAcylphosphataseP0AB65ACYP_ECOLIyccXhttp://ecmdb.ca/proteins/P0AB65.xmlPropionate kinaseP11868TDCD_ECOLItdcDhttp://ecmdb.ca/proteins/P11868.xmlPhosphoribosylglycinamide formyltransferase 2P33221PURT_ECOLIpurThttp://ecmdb.ca/proteins/P33221.xmlEthanolamine utilization protein eutDP77218EUTD_ECOLIeutDhttp://ecmdb.ca/proteins/P77218.xmlAcetyl-CoA + Phosphate <> Acetylphosphate + Coenzyme AR00230PHOSACETYLTRANS-RXNAcetic acid + Adenosine triphosphate <> Acetylphosphate + ADPR00315ACETATEKIN-RXNAcetylphosphate + Water <> Acetic acid + PhosphateR00317Adenosine triphosphate + Acetic acid > ADP + AcetylphosphateAcetyl-CoA + Inorganic phosphate > CoA + AcetylphosphateAcetyl-CoA + Phosphate > Coenzyme A + AcetylphosphatePW_R006095Acetylphosphate + ADP > Adenosine triphosphate + Acetic acidPW_R006097Acetyl-CoA + Phosphate <> Acetylphosphate + Coenzyme AAcetic acid + Adenosine triphosphate <> Acetylphosphate + ADPAcetic acid + Adenosine triphosphate <> Acetylphosphate + ADPGutnick 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 glucoseShake flask and filter culture1070.0uM0.037 oCK12 NCM3722Mid-Log Phase42800000Bennett, 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 5:593-599.19561621Gutnick 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 glycerolShake flask and filter culture1050.0uM0.037 oCK12 NCM3722Mid-Log Phase42000000Bennett, 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 5:593-599.19561621Gutnick 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 acetateShake flask and filter culture1560.0uM0.037 oCK12 NCM3722Mid-Log Phase62400000Bennett, 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 5:593-599.19561621