2.0 2012-05-31 13:54:55 -0600 2015-09-13 12:56:12 -0600 ECMDB01882 M2MDB000427 Dihydroxyacetone Dihydroxyacetone 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-propanone 1,3-Dihydroxyacetone 1,3-Dihydroxydimethyl ketone 1,3-Dihydroxypropan-2-one 1,3-Dihydroxypropanone A,a'-Dihydroxyacetone Aliphatic ketone Bis(hydroxymethyl) ketone Chromelin Dihydroxy-acetone Dihydroxyacetone Dihyxal Glycerone Ketochromin Otan Oxantin Oxatone Protosol Soleal Triulose Viticolor C3H6O3 90.0779 90.031694058 1,3-dihydroxypropan-2-one dihydroxyacetone 96-26-4 OCC(=O)CO InChI=1S/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2 RXKJFZQQPQGTFL-UHFFFAOYSA-N Solid Cytosol Extra-organism Periplasm logp -1.65 ALOGPS logs 0.97 ALOGPS solubility 8.38e+02 g/l ALOGPS melting_point 90 oC logp -1.5 ChemAxon pka_strongest_acidic 13.49 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac 1,3-dihydroxypropan-2-one ChemAxon average_mass 90.0779 ChemAxon mono_mass 90.031694058 ChemAxon smiles OCC(=O)CO ChemAxon formula C3H6O3 ChemAxon inchi InChI=1S/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2 ChemAxon inchikey RXKJFZQQPQGTFL-UHFFFAOYSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 19.6 ChemAxon polarizability 8.1 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Methane metabolism ec00680 Glycerolipid metabolism ec00561 Propanoate 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. PW000940 ec00640 Metabolic Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 glycerol degradation V GLYCEROLMETAB-PWY Specdb::CMs 868 Specdb::CMs 979 Specdb::CMs 3123 Specdb::CMs 30146 Specdb::CMs 30520 Specdb::CMs 31363 Specdb::CMs 32014 Specdb::CMs 38168 Specdb::CMs 155922 Specdb::NmrOneD 1778 Specdb::NmrOneD 4727 Specdb::NmrOneD 4728 Specdb::NmrOneD 102618 Specdb::NmrOneD 102619 Specdb::NmrOneD 102620 Specdb::NmrOneD 102621 Specdb::NmrOneD 102622 Specdb::NmrOneD 102623 Specdb::NmrOneD 102624 Specdb::NmrOneD 102625 Specdb::NmrOneD 102626 Specdb::NmrOneD 102627 Specdb::NmrOneD 102628 Specdb::NmrOneD 102629 Specdb::NmrOneD 102630 Specdb::NmrOneD 102631 Specdb::NmrOneD 102632 Specdb::NmrOneD 102633 Specdb::NmrOneD 102634 Specdb::NmrOneD 102635 Specdb::NmrOneD 102636 Specdb::NmrOneD 102637 Specdb::MsMs 21329 Specdb::MsMs 21330 Specdb::MsMs 21331 Specdb::MsMs 22880 Specdb::MsMs 22881 Specdb::MsMs 22882 Specdb::MsMs 2419179 Specdb::MsMs 2419180 Specdb::MsMs 2419181 Specdb::MsMs 2542673 Specdb::MsMs 2542674 Specdb::MsMs 2542675 Specdb::NmrTwoD 1718 HMDB01882 670 650 C00184 16016 DIHYDROXYACETONE 2HA Dihydroxyacetone 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. 21097882 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. 22080510 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. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). 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European Journal of Biochemistry (1977), 75(2), 433-9. http://hmdb.ca/system/metabolites/msds/000/001/473/original/HMDB01882.pdf?1358463252 Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml Glycerol dehydrogenase P0A9S5 GLDA_ECOLI gldA http://ecmdb.ca/proteins/P0A9S5.xml PTS-dependent dihydroxyacetone kinase, dihydroxyacetone-binding subunit dhaK P76015 DHAK_ECOLI dhaK http://ecmdb.ca/proteins/P76015.xml Fructose-6-phosphate aldolase 2 P32669 FSAB_ECOLI fsaB http://ecmdb.ca/proteins/P32669.xml PTS-dependent dihydroxyacetone kinase, ADP-binding subunit dhaL P76014 DHAL_ECOLI dhaL http://ecmdb.ca/proteins/P76014.xml Fructose-6-phosphate aldolase 1 P78055 FSAA_ECOLI fsaA http://ecmdb.ca/proteins/P78055.xml PTS-dependent dihydroxyacetone kinase, phosphotransferase subunit dhaM P37349 DHAM_ECOLI dhaM http://ecmdb.ca/proteins/P37349.xml Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Fructose 6-phosphate <> Dihydroxyacetone + D-Glyceraldehyde 3-phosphate RXN0-313 Dihydroxyacetone + Phosphoenolpyruvic acid > Dihydroxyacetone phosphate + Pyruvic acid 2.7.1.121-RXN Glycerol + NAD <> Dihydroxyacetone + Hydrogen ion + NADH R01034 GLYCDEH-RXN Adenosine triphosphate + Dihydroxyacetone <> ADP + Dihydroxyacetone phosphate R01011 Dihydroxyacetone + Phosphoenolpyruvic acid > Dihydroxyacetone phosphate + Pyruvic acid 2.7.1.121-RXN Fructose 6-phosphate > Dihydroxyacetone + D-Glyceraldehyde 3-phosphate Glycerol + NAD > Dihydroxyacetone + NADH