1.0 2016-09-30 22:48:35 UTC 2020-06-04 20:47:46 UTC BMDB0001882 BMDB01882 Dihydroxyacetone Dihydroxyacetone, also known as chromelin or DHA, belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. Dihydroxyacetone exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Dihydroxyacetone exists in all living species, ranging from bacteria to humans. In cattle, dihydroxyacetone is involved in the metabolic pathway called the mitochondrial electron transport chain pathway. 1,3-Dihydroxy-2-propanone 1,3-Dihydroxyacetone 1,3-Dihydroxydimethyl ketone 1,3-Dihydroxypropan-2-one 1,3-Dihydroxypropanone 1,3-Propanediol-2-one alpha,Alpha'-dihydroxyacetone Bis(hydroxymethyl) ketone DHA Glycerone Chromelin a,Alpha'-dihydroxyacetone Α,alpha'-dihydroxyacetone a,A'-dihydroxyacetone Aliphatic ketone Dihydroxy-acetone Dihyxal Ketochromin Otan Oxantin Oxatone Protosol Soleal Triulose Viticolor 1,3 Dihydroxy 2 propanone Summers brand OF dihydroxyacetone ICN brand OF dihydroxyacetone Vitadye 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 belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Monosaccharides Alpha-hydroxy ketones Glycerone and derivatives Hydrocarbon derivatives Organic oxides Primary alcohols Alcohol Aliphatic acyclic compound Alpha-hydroxy ketone Carbonyl group Glycerone or derivatives Hydrocarbon derivative Ketone Monosaccharide Organic oxide Primary alcohol Aliphatic acyclic compounds Ketoses a small molecule ketotriose Solid melting_point 90 °C logp -1.65 ALOGPS logs 0.97 ALOGPS 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 number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 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::NmrTwoD 1718 Specdb::MsIr 1435 Specdb::MsIr 1436 Specdb::MsIr 1437 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 Epidermis Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. 11913692 Milk Milk from Friesuan Holstein cows (n=1035) Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 Ruminal Fluid 16.56 +/- 4.22 uM Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid Samples collected from 16 multiparous Holstein cows Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. 25599412 Ruminal Fluid 6.5 uM By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 6.8 uM By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 6.3 uM By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 16.6 uM By NMR. No barley grains in diet (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 7.2 uM By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter) Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594 doi: 10.1007/s11306-010-0227-6 Ruminal Fluid 7.9 uM By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter) Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594 doi: 10.1007/s11306-010-0227-6 Ruminal Fluid 6.4 uM By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter) Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594 doi: 10.1007/s11306-010-0227-6 Ruminal Fluid 15.6 uM By NMR. Primiparous Holstein cows, no barley grains in diet. Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594 doi: 10.1007/s11306-010-0227-6 Ruminal Fluid 7 +/- 2 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid 7 +/- 3 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid 7 +/- 2 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid 17 +/- 5 uM Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Skeletal Muscle Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 C00184 DB01775 FDB030826 670 650 16016 DIHYDROXYACETONE 34170 Dihydroxyacetone 6368 Hochuli, 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. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. 11913692