2.0 2012-05-31 10:23:52 -0600 2015-09-13 12:56:07 -0600 ECMDB00215 M2MDB000088 N-Acetyl-D-glucosamine N-Acetyl-D-Glucosamine (N-acetlyglucosamine) is a monosaccharide derivative of glucose. Chemically it is an amide between glucosamine and acetic acid. A single N-acetlyglucosamine moiety linked to serine or threonine residues on nuclear and cytoplasmic proteins -O-GlcNAc, is an ubiquitous post-translational protein modification. O-GlcNAc modified proteins are involved in sensing the nutrient status of the surrounding cellular environment and adjusting the activity of cellular proteins accordingly. O-GlcNAc initiates a protective response to stress, modulates a cell's capacity to grow and divide, and regulates gene transcription. (PMID 16237703) 2-(Acetylamino)-2-deoxyhexose 2-Acetamido-2-deoxy-D-glucose 2-Acetamido-2-deoxyglucose 2-Acetamido-D-glucose 2-Acetylamino-2-deoxy-D-glucose N-acetylglucosamine Acetylglucosamine Glcnac N-Acetylchitosamine N-Acetylglucosamine NAcGlc 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 7512-17-6 [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 Solid Cytosol Extra-organism Periplasm logp -2.60 ALOGPS logs 0.06 ALOGPS solubility 2.54e+02 g/l ALOGPS melting_point 210 oC 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 Amino sugar and nucleotide sugar metabolism ec00520 Phosphotransferase system (PTS) ec02060 ABC transporters ec02010 chitobiose degradation PWY0-1309 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 Specdb::NmrTwoD 997 Specdb::NmrTwoD 1213 HMDB00215 439174 10035566 C00140 17411 N-ACETYL-D-GLUCOSAMINE NGZ N-acetylglucosamine Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Slawson, C., Housley, M. P., Hart, G. W. (2006). "O-GlcNAc cycling: how a single sugar post-translational modification is changing the way we think about signaling networks." J Cell Biochem 97:71-83. 16237703 Zhang, He; Qi, Shanlong; Yang, Shenggui. Production of N-acetyl-D-glucosamine from chitin. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 6pp. http://hmdb.ca/system/metabolites/msds/000/000/153/original/HMDB00215.pdf?1358895005 Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml PTS system N-acetylglucosamine-specific EIICBA component P09323 PTW3C_ECOLI nagE http://ecmdb.ca/proteins/P09323.xml Probable bifunctional chitinase/lysozyme P13656 CHIA_ECOLI chiA http://ecmdb.ca/proteins/P13656.xml 6-phospho-beta-glucosidase P17411 CHBF_ECOLI chbF http://ecmdb.ca/proteins/P17411.xml Glucose-specific phosphotransferase enzyme IIA component P69783 PTGA_ECOLI crr http://ecmdb.ca/proteins/P69783.xml PTS system glucose-specific EIICB component P69786 PTGCB_ECOLI ptsG http://ecmdb.ca/proteins/P69786.xml Beta-hexosaminidase P75949 NAGZ_ECOLI nagZ http://ecmdb.ca/proteins/P75949.xml N-acetyl-D-glucosamine kinase P75959 NAGK_ECOLI nagK http://ecmdb.ca/proteins/P75959.xml Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml PTS system N-acetylglucosamine-specific EIICBA component P09323 PTW3C_ECOLI nagE http://ecmdb.ca/proteins/P09323.xml Probable bifunctional chitinase/lysozyme P13656 CHIA_ECOLI chiA http://ecmdb.ca/proteins/P13656.xml PTS system glucose-specific EIICB component P69786 PTGCB_ECOLI ptsG http://ecmdb.ca/proteins/P69786.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Phosphoenolpyruvic acid + N-Acetyl-D-glucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + Pyruvic acid TRANS-RXN-167 N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramic acid + Water > N-Acetyl-D-glucosamine + 1,6-Anhydro-N-acetylmuramate N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide + Water > N-Acetyl-D-glucosamine + 1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide + Water > N-Acetyl-D-glucosamine + 1,6-Anhydrous-N-Acetylmuramyl-tripeptide N-Acetyl-D-glucosamine + Adenosine triphosphate <> N-Acetyl-D-Glucosamine 6-Phosphate + ADP + Hydrogen ion R01201 N-ACETYLGLUCOSAMINE-KINASE-RXN Diacetylchitobiose-6-phosphate + Water > N-Acetyl-D-glucosamine + N-Acetyl-D-Glucosamine 6-Phosphate RXN0-5243 Chitobiose + Water <>2 N-Acetyl-D-glucosamine R00022 Adenosine triphosphate + N-Acetyl-D-glucosamine <> ADP + N-Acetyl-D-Glucosamine 6-Phosphate R01201 Chitin + Water <> N-Acetyl-D-glucosamine + Chitin R01206 Protein N(pi)-phospho-L-histidine + N-Acetyl-D-glucosamine <> Protein histidine + N-Acetyl-D-Glucosamine 6-Phosphate R05199 a peptidoglycan + Water a peptidoglycan with cleaved N-acetyl-glucosamine + N-Acetyl-D-glucosamine 3.2.1.17-RXN N-Acetyl-D-glucosamine + Adenosine triphosphate > Hydrogen ion + N-Acetyl-D-Glucosamine 6-Phosphate + ADP R01201 N-ACETYLGLUCOSAMINE-KINASE-RXN N-acetyl-β-D-glucosamine(anhydrous)-N-acetylmuramate + Water N-Acetyl-D-glucosamine + 1,6-Anhydro-N-acetylmuramate RXN0-5226 Phosphoenolpyruvic acid + N-Acetyl-D-glucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + Pyruvic acid TRANS-RXN-167 Adenosine triphosphate + Water + N-Acetyl-D-glucosamine > N-Acetyl-D-glucosamine + ADP + Phosphate + Hydrogen ion TRANS-RXN0-210 Adenosine triphosphate + Water + N-Acetyl-D-glucosamine > N-Acetyl-D-glucosamine + ADP + Phosphate + Hydrogen ion TRANS-RXN0-210 Chitobiose + Water <>2 N-Acetyl-D-glucosamine Chitobiose + Water <>2 N-Acetyl-D-glucosamine