1.0 2016-09-30 23:01:41 UTC 2020-05-11 20:40:10 UTC BMDB0002817 BMDB02817 N-Acetylglucosamine 6-phosphate N-Acetylglucosamine 6-phosphoric acid GlcNAc6p 2-Acetamido-2-deoxy-D-glucose 6-phosphate GlcNAc-6-P N-Acetyl-D-glucosamine 6-phosphate N-Acetylglucosamine 6-phosphate C8H16NO9P 301.1877 301.056267627 {[(2R,3S,4R,5R,6S)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid [(2R,3S,4R,5R,6S)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxyphosphonic acid 73495-11-1 CC(=O)N[C@H]1[C@@H](O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O InChI=1S/C8H16NO9P/c1-3(10)9-5-7(12)6(11)4(18-8(5)13)2-17-19(14,15)16/h4-8,11-13H,2H2,1H3,(H,9,10)(H2,14,15,16)/t4-,5-,6-,7-,8+/m1/s1 BRGMHAYQAZFZDJ-PVFLNQBWSA-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 1,2-diols Acetamides Carbonyl compounds Hemiacetals Hexose phosphates Hydrocarbon derivatives Monoalkyl phosphates Monosaccharide phosphates N-acyl-alpha-hexosamines Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Secondary alcohols Secondary carboxylic acid amides 1,2-diol Acetamide Acylaminosugar Alcohol Aliphatic heteromonocyclic compound Alkyl phosphate Carbonyl group Carboxamide group Carboxylic acid derivative Hemiacetal Hexose phosphate Hydrocarbon derivative Monoalkyl phosphate Monosaccharide Monosaccharide phosphate N-acyl-alpha-hexosamine Organic nitrogen compound Organic oxide Organic phosphoric acid derivative Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Phosphoric acid ester Polyol Secondary alcohol Secondary carboxylic acid amide Aliphatic heteromonocyclic compounds amino sugar Solid logp -2.02 ALOGPS logs -1.23 ALOGPS logp -3.3 ChemAxon pka_strongest_acidic 1.23 ChemAxon pka_strongest_basic -0.79 ChemAxon iupac {[(2R,3S,4R,5R,6S)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 301.1877 ChemAxon mono_mass 301.056267627 ChemAxon smiles CC(=O)N[C@H]1[C@@H](O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O ChemAxon formula C8H16NO9P ChemAxon inchi InChI=1S/C8H16NO9P/c1-3(10)9-5-7(12)6(11)4(18-8(5)13)2-17-19(14,15)16/h4-8,11-13H,2H2,1H3,(H,9,10)(H2,14,15,16)/t4-,5-,6-,7-,8+/m1/s1 ChemAxon inchikey BRGMHAYQAZFZDJ-PVFLNQBWSA-N ChemAxon polar_surface_area 165.78 ChemAxon refractivity 57.9 ChemAxon polarizability 25.69 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 8 ChemAxon donor_count 6 ChemAxon physiological_charge -2 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 26570 Specdb::CMs 38480 Specdb::CMs 136153 Specdb::CMs 143887 Specdb::MsMs 25787 Specdb::MsMs 25788 Specdb::MsMs 25789 Specdb::MsMs 32345 Specdb::MsMs 32346 Specdb::MsMs 32347 Specdb::MsMs 2457344 Specdb::MsMs 2457345 Specdb::MsMs 2457346 Specdb::MsMs 2481826 Specdb::MsMs 2481827 Specdb::MsMs 2481828 Specdb::NmrOneD 149340 Specdb::NmrOneD 149341 Specdb::NmrOneD 149342 Specdb::NmrOneD 149343 Specdb::NmrOneD 149344 Specdb::NmrOneD 149345 Specdb::NmrOneD 149346 Specdb::NmrOneD 149347 Specdb::NmrOneD 149348 Specdb::NmrOneD 149349 Specdb::NmrOneD 149350 Specdb::NmrOneD 149351 Specdb::NmrOneD 149352 Specdb::NmrOneD 149353 Specdb::NmrOneD 149354 Specdb::NmrOneD 149355 Specdb::NmrOneD 149356 Specdb::NmrOneD 149357 Specdb::NmrOneD 149358 Specdb::NmrOneD 149359 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 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 FDB023067 388358 439219 16G N-ACETYL-D-GLUCOSAMINE-6-P 3429 Maley, Frank; Lardy, Henry A. Phosphoric esters of biological importance. VI. The synthesis of D-glucosamine 6-phosphate and N-acetyl-D-glucosamine 6-phosphate. Journal of the American Chemical Society (1956), 78 1393-7.