1.0 2016-10-03 18:23:55 UTC 2020-05-21 16:28:28 UTC BMDB0011744 BMDB11744 N-Acetyl-D-mannosamine N-Acetylmannosamine, also known as n-acetylmannosamine or n-acetylmannosamine, 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. N-Acetylmannosamine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetylmannosamine participates in a number of enzymatic reactions, within cattle. In particular, N-Acetylmannosamine can be biosynthesized from N-acetyl-D-glucosamine; which is catalyzed by the enzyme N-acylglucosamine 2-epimerase. In addition, N-Acetylmannosamine and uridine 5'-diphosphate can be biosynthesized from uridine diphosphate-N-acetylglucosamine through the action of the enzyme bifunctional UDP-N-acetyl glucosamine 2-epimerase / N-acetylmannosamine kinase. In cattle, N-acetylmannosamine is involved in the metabolic pathway called the amino sugar metabolism pathway. beta-ManNAc N-Acetyl-beta-mannosamine b-ManNAc Β-mannac N-Acetyl-b-mannosamine N-Acetyl-β-mannosamine 2-Acetamido-2-deoxy-D-mannopyranose 2-Acetamido-2-deoxy-D-mannose ManNAc N-Acetyl-D-mannosamine N-Acetylmannosamine, (D)-isomer N-Acetylmannosamine, (L)-isomer C8H15NO6 221.2078 221.089937217 N-[(2R,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide N-acetylmannosamine 7772-94-3 CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O 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-/m1/s1 OVRNDRQMDRJTHS-OZRXBMAMSA-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 N-acetyl-D-mannosamine Solid logp -2.60 ALOGPS logs 0.06 ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 11.6 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac N-[(2R,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide ChemAxon average_mass 221.2078 ChemAxon mono_mass 221.089937217 ChemAxon smiles CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O 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-/m1/s1 ChemAxon inchikey OVRNDRQMDRJTHS-OZRXBMAMSA-N ChemAxon polar_surface_area 119.25 ChemAxon refractivity 47.02 ChemAxon polarizability 20.82 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::CMs 21950 Specdb::CMs 37939 Specdb::CMs 102647 Specdb::CMs 102648 Specdb::CMs 102649 Specdb::CMs 102650 Specdb::CMs 136056 Specdb::CMs 143790 Specdb::NmrTwoD 1054 Specdb::NmrTwoD 1588 Specdb::NmrOneD 1647 Specdb::NmrOneD 21262 Specdb::NmrOneD 21263 Specdb::NmrOneD 21264 Specdb::NmrOneD 21265 Specdb::NmrOneD 21266 Specdb::NmrOneD 21267 Specdb::NmrOneD 21268 Specdb::NmrOneD 21269 Specdb::NmrOneD 21270 Specdb::NmrOneD 21271 Specdb::NmrOneD 21272 Specdb::NmrOneD 21273 Specdb::NmrOneD 21274 Specdb::NmrOneD 21275 Specdb::NmrOneD 21276 Specdb::NmrOneD 21277 Specdb::NmrOneD 21278 Specdb::NmrOneD 21279 Specdb::NmrOneD 21280 Specdb::NmrOneD 21281 Specdb::NmrOneD 166618 Specdb::MsMs 1427 Specdb::MsMs 1428 Specdb::MsMs 1429 Specdb::MsMs 314767 Specdb::MsMs 314768 Specdb::MsMs 314769 Specdb::MsMs 360577 Specdb::MsMs 360578 Specdb::MsMs 360579 Specdb::MsMs 2453467 Specdb::MsMs 2453468 Specdb::MsMs 2453469 Specdb::MsMs 2484675 Specdb::MsMs 2484676 Specdb::MsMs 2484677 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 Mammary Gland 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 Mammary Gland 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 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 C00645 FDB028419 9271300 63154 11096158 N-ACETYL-D-MANNOSAMINE N-acetylmannosamine 35606 6024 BMDBP00109 N-acetylneuraminate lyase Q29RY9 NPL Enzyme BMDBP02867 Glucosamine (UDP-N-acetyl)-2-epimerase/N-acetylmannosamine kinase F1MIL9 GNE Enzyme BMDBP02868 N-acetylneuraminate synthase Q1RMX7 NANS Enzyme