1.0 2016-09-30 22:26:51 UTC 2020-06-04 20:57:15 UTC BMDB0000215 BMDB00215 N-Acetyl-D-glucosamine N-Acetyl-D-glucosamine belongs to the class of chemical entities known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. N-Acetyl-D-glucosamine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-D-glucosamine participates in a number of enzymatic reactions, within cattle. In particular, N-Acetyl-D-glucosamine can be biosynthesized from chitobiose; which is catalyzed by the enzyme Beta-hexosaminidase subunit alpha. In addition, N-Acetyl-D-glucosamine can be converted into N-acetyl-D-glucosamine 6-phosphate; which is mediated by the enzyme N-acetyl-D-glucosamine kinase. In cattle, N-acetyl-D-glucosamine is involved in the metabolic pathway called the amino sugar metabolism pathway. 2-acetamido-2-Deoxyglucose N Acetyl D glucosamine 2 acetamido 2 Deoxyglucose 2-acetamido-2-Deoxy-D-glucose 2 acetamido 2 Deoxy D glucose 2-(Acetylamino)-2-deoxy-a-L-glucopyranose 2-(Acetylamino)-2-deoxy-α-L-glucopyranose C8H15NO6 221.2078 221.089937217 N-[(2R,3S,4S,5R,6S)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide N-[(2R,3S,4S,5R,6S)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide [H]OC([H])([H])[C@]1([H])O[C@@]([H])(O[H])[C@@]([H])(N([H])C(=O)C([H])([H])[H])[C@]([H])(O[H])[C@@]1([H])O[H] InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8+/m0/s1 OVRNDRQMDRJTHS-DMHSOCPYSA-N belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Acylaminosugars Acetamides Carbonyl compounds Hemiacetals Hexoses Hydrocarbon derivatives N-acyl-alpha-hexosamines Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Secondary carboxylic acid amides Acetamide Acylaminosugar Alcohol Aliphatic heteromonocyclic compound Carbonyl group Carboxamide group Carboxylic acid derivative Hemiacetal Hexose monosaccharide Hydrocarbon derivative Monosaccharide N-acyl-alpha-hexosamine Organic nitrogen compound Organic oxide Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Polyol Primary alcohol Secondary alcohol Secondary carboxylic acid amide Aliphatic heteromonocyclic compounds Solid logp -2.60 ALOGPS logs 0.06 ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 11.6 ChemAxon pka_strongest_basic -0.78 ChemAxon iupac N-[(2R,3S,4S,5R,6S)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide ChemAxon average_mass 221.2078 ChemAxon mono_mass 221.089937217 ChemAxon smiles [H]OC([H])([H])[C@]1([H])O[C@@]([H])(O[H])[C@@]([H])(N([H])C(=O)C([H])([H])[H])[C@]([H])(O[H])[C@@]1([H])O[H] ChemAxon formula C8H15NO6 ChemAxon inchi InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8+/m0/s1 ChemAxon inchikey OVRNDRQMDRJTHS-DMHSOCPYSA-N ChemAxon polar_surface_area 119.25 ChemAxon refractivity 47.02 ChemAxon polarizability 20.6 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 0 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 997 Specdb::NmrTwoD 1213 Specdb::NmrOneD 1209 Specdb::MsMs 352 Specdb::MsMs 353 Specdb::MsMs 354 Specdb::MsMs 1255024 Specdb::MsMs 1255025 Specdb::MsMs 1255026 Specdb::MsMs 1370227 Specdb::MsMs 1370228 Specdb::MsMs 1370229 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 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 Milk Commercial, conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8 Milk Detected but not quantified in conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 Milk 198.908 (126.578-370.692) uM Pasteurized whole milk Esperanza Troyano, Mar Villamiel, Agustin Olano, Jesus Sanz, and Isabel Martinez-Castro. Monosaccharides and myo-Inositol in Commercial Milks. J. Agric. Food Chem., 1996, 44 (3), pp 815–817 Milk 506.311 uM Raw milk Johan E. Hoff. Determination of N-Acetylglucosamine-1-Phosphate and N-Acetylglucosamine in Milk. June 1963, Volume 46, Issue 6, Pages 573–574 Milk 230.10 +/- 2.26 uM Whole milk Tommaso R.I. Cataldi, Massimiliano Angelotti, Giuliana Bianco. Determination of mono- and disaccharides in milk and milk products by high-performance anion-exchange chromatography with pulsed amperometric detection. Analytica Chimica Acta 485 (2003) 43–49 Milk 238 +/- 90 uM 1% milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 302 +/- 76 uM 2% milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 278 +/- 94 uM 3.25% milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 351 +/- 34 uM Skim milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Neuron 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 Placenta 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 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 Prostate Tissue 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 Ruminal Fluid 16 uM N-acetyl-D-Glucosamine act as growth factor in rumen of cows for methogenic bacteria Prins RA: Presence of growth factors for Methanobacterium ruminantium in both gram-positive and gram-negative bacteria. Antonie Van Leeuwenhoek. 1974;40(4):585-9. 4219266 11861101 NGZ Zhang, He; Qi, Shanlong; Yang, Shenggui. Production of N-acetyl-D-glucosamine from chitin. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 6pp. 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 Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) BMDBP00604 Beta-1,4-galactosyltransferase 1 P08037 B4GALT1 Enzyme BMDBP00640 Beta-1,4-galactosyltransferase 3 Q5EA87 B4GALT3 Enzyme BMDBP00651 Protein O-linked-mannose beta-1,2-N-acetylglucosaminyltransferase 1 Q5EAB6 POMGNT1 Enzyme BMDBP00699 Lysozyme C, milk isozyme Q6B411 Enzyme BMDBP00700 Lysozyme C-3 Q06284 LYZ3 Enzyme BMDBP00701 Lysozyme-like protein 6 Q29RT1 LYZL6 Enzyme BMDBP00703 N-acetyl-D-glucosamine kinase Q3SZM9 NAGK Enzyme BMDBP00704 Lysozyme C, non-stomach isozyme P80189 LYS Enzyme BMDBP00705 Lysozyme C, intestinal isozyme Q6B410 Enzyme BMDBP00706 N-acetylglucosamine-1-phosphodiester alpha-N-acetylglucosaminidase P68827 NAGPA Enzyme BMDBP00707 Lysozyme C-1 Q06285 LYZ1 Enzyme BMDBP00708 Lysozyme C, tracheal isozyme Q27996 Enzyme BMDBP00709 Lysozyme C P04421 LYZ1 Enzyme BMDBP00710 Lysozyme-like protein 1 A0JNM6 LYZL1 Enzyme BMDBP00711 Sperm acrosome-associated protein 5 Q32PD6 SPACA5 Enzyme BMDBP00712 Lysozyme C-2 Q06283 LYZ2 Enzyme BMDBP01617 Collectin-43 P42916 CL43 Enzyme BMDBP01908 Conglutinin P23805 CGN1 Enzyme BMDBP01910 Mannose-binding protein C O02659 MBL Enzyme BMDBP02058 Ficolin-2 Q5I2E5 FCN2 Enzyme BMDBP02541 Sperm acrosome membrane-associated protein 3 A6QQ77 SPACA3 Enzyme