1.0 2016-09-30 22:47:03 UTC 2020-05-21 16:26:54 UTC BMDB0001514 BMDB01514 Glucosamine Glucosamine, also known as dona or chitosamine, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Glucosamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Glucosamine exists in all living organisms, ranging from bacteria to humans. Glucosamine can be converted into glucosamine 6-phosphate; which is mediated by the enzyme hexokinase-1. In cattle, glucosamine is involved in the metabolic pathway called the amino sugar metabolism pathway. 2-Amino-2-deoxy-D-glucose Chitosamine D-Glucosamine (+)-2-Amino-2-deoxy-D-glucopyranose (3R,4R,5S,6R)-3-Amino-6-(hydroxymethyl)oxane-2,4,5-triol 2-Amino-2-deoxy-D-glucopyranose 2-Amino-2-deoxyglucose 2-Aminoglucose 2-Deoxy-2-amino-D-glucose 2-Deoxy-2-aminoglucose Cosamin D-(+)-Glucosamine Dona Fides ecopharma brand OF glucosamine sulfate Rottapharm brand OF glucosamine sulfate Xicil 2 Amino 2 deoxyglucose Glucosamine sulfate Sulfate, glucosamine Dona S Opfermann brand OF glucosamine sulfate Hespercorbin C6H13NO5 179.1711 179.079372531 (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol glucosamine 3416-24-8 N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6?/m1/s1 MSWZFWKMSRAUBD-IVMDWMLBSA-N belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Hexoses 1,2-aminoalcohols Aminosaccharides Hemiacetals Hydrocarbon derivatives Monoalkylamines Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols 1,2-aminoalcohol Alcohol Aliphatic heteromonocyclic compound Amine Amino saccharide Hemiacetal Hexose monosaccharide Hydrocarbon derivative Organic nitrogen compound Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Polyol Primary alcohol Primary aliphatic amine Primary amine Secondary alcohol Aliphatic heteromonocyclic compounds Amino sugars D-glucosamine Solid logp -2.73 ALOGPS logs 0.49 ALOGPS logp -3 ChemAxon pka_strongest_acidic 11.73 ChemAxon pka_strongest_basic 8.23 ChemAxon iupac (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol ChemAxon average_mass 179.1711 ChemAxon mono_mass 179.079372531 ChemAxon smiles N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O ChemAxon formula C6H13NO5 ChemAxon inchi InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6?/m1/s1 ChemAxon inchikey MSWZFWKMSRAUBD-IVMDWMLBSA-N ChemAxon polar_surface_area 116.17 ChemAxon refractivity 37.58 ChemAxon polarizability 16.87 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::NmrTwoD 2013 Specdb::NmrTwoD 2014 Specdb::CMs 17655 Specdb::CMs 38103 Specdb::CMs 132620 Specdb::CMs 140354 Specdb::NmrOneD 96358 Specdb::NmrOneD 96359 Specdb::NmrOneD 96360 Specdb::NmrOneD 96361 Specdb::NmrOneD 96362 Specdb::NmrOneD 96363 Specdb::NmrOneD 96364 Specdb::NmrOneD 96365 Specdb::NmrOneD 96366 Specdb::NmrOneD 96367 Specdb::NmrOneD 96368 Specdb::NmrOneD 96369 Specdb::NmrOneD 96370 Specdb::NmrOneD 96371 Specdb::NmrOneD 96372 Specdb::NmrOneD 96373 Specdb::NmrOneD 96374 Specdb::NmrOneD 96375 Specdb::NmrOneD 96376 Specdb::NmrOneD 96377 Specdb::MsMs 75216 Specdb::MsMs 75217 Specdb::MsMs 75218 Specdb::MsMs 134817 Specdb::MsMs 134818 Specdb::MsMs 134819 Specdb::MsMs 1218130 Specdb::MsMs 1218131 Specdb::MsMs 1218132 Specdb::MsMs 2226560 Specdb::MsMs 2228186 Specdb::MsMs 2228961 Specdb::MsMs 2230465 Specdb::MsMs 2231300 Specdb::MsMs 2232921 Specdb::MsMs 2233612 Specdb::MsMs 2235306 Specdb::MsMs 2236469 Specdb::MsMs 2236892 Specdb::MsMs 2238580 Specdb::MsMs 2239018 Specdb::MsMs 2240674 Specdb::MsMs 2241001 Specdb::MsMs 2242794 Specdb::MsMs 2243064 Cartilage 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 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 Fibroblasts 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 Intestine 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 Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Milk By GC-TOFMS and UPLC-QTOFMS Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. 27999311 Milk 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 Platelet 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 388352 FDB022668 C00329 439213 DB01296 47977 34633 Glucosamine 266 Li, Nan; Li, Jiheng. Preparation of D-glucosamine hydrochloride. Zhongguo Yaoke Daxue Xuebao (1997), 28(1), 56-58. 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 Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. 27999311 BMDBP00912 Hexokinase-1 P27595 HK1 Enzyme