2.02012-05-31 13:54:55 -06002015-09-13 12:56:12 -0600ECMDB01882M2MDB000427DihydroxyacetoneDihydroxyacetone or DHA, also known as glycerone, is a simple carbohydrate (a triose) with formula C3H6O3. It is an intermedate in the process of glycerolipid metabolism. It is converted from glycerol by glycerol dehydrogenase, NAD (EC:1.1.1.6) and converts to glycerone phosphate by dihydroxyacetone kinase (EC:2.7.1.-). (KEGG)1,3-Dihydroxy-2-propanone1,3-Dihydroxyacetone1,3-Dihydroxydimethyl ketone1,3-Dihydroxypropan-2-one1,3-DihydroxypropanoneA,a'-DihydroxyacetoneAliphatic ketoneBis(hydroxymethyl) ketoneChromelinDihydroxy-acetoneDihydroxyacetoneDihyxalGlyceroneKetochrominOtanOxantinOxatoneProtosolSolealTriuloseViticolorC3H6O390.077990.0316940581,3-dihydroxypropan-2-onedihydroxyacetone96-26-4OCC(=O)COInChI=1S/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2RXKJFZQQPQGTFL-UHFFFAOYSA-NSolidCytosolExtra-organismPeriplasmlogp-1.65logs0.97solubility8.38e+02 g/lmelting_point90 oClogp-1.5pka_strongest_acidic13.49pka_strongest_basic-3.3iupac1,3-dihydroxypropan-2-oneaverage_mass90.0779mono_mass90.031694058smilesOCC(=O)COformulaC3H6O3inchiInChI=1S/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2inchikeyRXKJFZQQPQGTFL-UHFFFAOYSA-Npolar_surface_area57.53refractivity19.6polarizability8.1rotatable_bond_count2acceptor_count3donor_count2physiological_charge0formal_charge0Methane metabolismec00680Glycerolipid metabolismec00561Propanoate 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.PW000940ec00640MetabolicMicrobial metabolism in diverse environmentsec01120Metabolic pathwayseco01100glycerol degradation VGLYCEROLMETAB-PWYSpecdb::CMs868Specdb::CMs979Specdb::CMs3123Specdb::CMs30146Specdb::CMs30520Specdb::CMs31363Specdb::CMs32014Specdb::CMs38168Specdb::CMs155922Specdb::NmrOneD1778Specdb::NmrOneD4727Specdb::NmrOneD4728Specdb::NmrOneD102618Specdb::NmrOneD102619Specdb::NmrOneD102620Specdb::NmrOneD102621Specdb::NmrOneD102622Specdb::NmrOneD102623Specdb::NmrOneD102624Specdb::NmrOneD102625Specdb::NmrOneD102626Specdb::NmrOneD102627Specdb::NmrOneD102628Specdb::NmrOneD102629Specdb::NmrOneD102630Specdb::NmrOneD102631Specdb::NmrOneD102632Specdb::NmrOneD102633Specdb::NmrOneD102634Specdb::NmrOneD102635Specdb::NmrOneD102636Specdb::NmrOneD102637Specdb::MsMs22880Specdb::MsMs22881Specdb::MsMs22882Specdb::MsMs2542673Specdb::MsMs2542674Specdb::MsMs2542675Specdb::MsMs21329Specdb::MsMs21330Specdb::MsMs21331Specdb::MsMs2419179Specdb::MsMs2419180Specdb::MsMs2419181Specdb::NmrTwoD1718HMDB01882670650C0018416016DIHYDROXYACETONE2HADihydroxyacetoneKeseler, 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 80:2939-2948.18331064Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32.6321058Phillipou G, Seaborn CJ, Phillips PJ: Re-evaluation of the fructosamine reaction. Clin Chem. 1988 Aug;34(8):1561-4.3402055Blake SM, Treble NJ: Popliteus tendon tenosynovitis. Br J Sports Med. 2005 Dec;39(12):e42; discussion e42.16306488Forest SE, Grothaus JT, Ertel KD, Rader C, Plante J: Fluorescence spectral imaging of dihydroxyacetone on skin in vivo. Photochem Photobiol. 2003 May;77(5):524-30.12812295Taylor CR, Kwangsukstith C, Wimberly J, Kollias N, Anderson RR: Turbo-PUVA: dihydroxyacetone-enhanced photochemotherapy for psoriasis: a pilot study. Arch Dermatol. 1999 May;135(5):540-4.10328194Kerr HH, Pantely GA, Metcalfe J, Welch JE: Reduction of human blood O2 affinity using dihydroxyacetone, phosphate, and pyruvate. J Appl Physiol. 1979 Sep;47(3):478-81.118143GOLDMAN L, WITTGENSTEIN E, BLANEY D, GOLDMAN J, SAWYER F: Studies of some physical properties of the dihydroxyacetone color complex. J Invest Dermatol. 1961 Apr;36:233-4.13706567WITTGENSTEIN E, BERRY HK: Staining of skin with dihydroxyacetone. Science. 1960 Sep 30;132(3431):894-5.13845496WITTGENSTEIN E, GUEST GM: Biochemical effects of dihydroxyacetone. J Invest Dermatol. 1961 Nov;37:421-6.14007781Hochuli, Erich; Taylor, Keith E.; Dutler, Hans. Dihydroxyacetone reductase from Mucor javanicus. 2. Identification of the physiological substrate and reactivity towards related compounds. European Journal of Biochemistry (1977), 75(2), 433-9.http://hmdb.ca/system/metabolites/msds/000/001/473/original/HMDB01882.pdf?1358463252Phosphoenolpyruvate-protein phosphotransferaseP08839PT1_ECOLIptsIhttp://ecmdb.ca/proteins/P08839.xmlGlycerol dehydrogenaseP0A9S5GLDA_ECOLIgldAhttp://ecmdb.ca/proteins/P0A9S5.xmlPTS-dependent dihydroxyacetone kinase, dihydroxyacetone-binding subunit dhaKP76015DHAK_ECOLIdhaKhttp://ecmdb.ca/proteins/P76015.xmlFructose-6-phosphate aldolase 2P32669FSAB_ECOLIfsaBhttp://ecmdb.ca/proteins/P32669.xmlPTS-dependent dihydroxyacetone kinase, ADP-binding subunit dhaLP76014DHAL_ECOLIdhaLhttp://ecmdb.ca/proteins/P76014.xmlFructose-6-phosphate aldolase 1P78055FSAA_ECOLIfsaAhttp://ecmdb.ca/proteins/P78055.xmlPTS-dependent dihydroxyacetone kinase, phosphotransferase subunit dhaMP37349DHAM_ECOLIdhaMhttp://ecmdb.ca/proteins/P37349.xmlPhosphocarrier protein HPrP0AA04PTHP_ECOLIptsHhttp://ecmdb.ca/proteins/P0AA04.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlFructose 6-phosphate <> Dihydroxyacetone + D-Glyceraldehyde 3-phosphateRXN0-313Dihydroxyacetone + Phosphoenolpyruvic acid > Dihydroxyacetone phosphate + Pyruvic acid2.7.1.121-RXNGlycerol + NAD <> Dihydroxyacetone + Hydrogen ion + NADHR01034GLYCDEH-RXNAdenosine triphosphate + Dihydroxyacetone <> ADP + Dihydroxyacetone phosphateR01011Dihydroxyacetone + Phosphoenolpyruvic acid > Dihydroxyacetone phosphate + Pyruvic acid2.7.1.121-RXNFructose 6-phosphate > Dihydroxyacetone + D-Glyceraldehyde 3-phosphateGlycerol + NAD > Dihydroxyacetone + NADH