2.0 2012-05-31 13:45:54 -0600 2015-10-15 16:13:51 -0600 ECMDB01129 M2MDB000266 N-Acetylmannosamine N-Acetylmannosamine is a monosaccharide that is used as a precursor in the chemical or enzymatic synthesis of the neuraminic acids found in glycolipids and glycoproteins. 2-Acetamido-2-deoxy-D-mannopyranose 2-Acetamido-2-deoxy-D-mannose ManNAc N-Acetyl-D-mannosamine N-Acetylmannosamine C8H15NO6 221.2078 221.089937217 N-[(3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid N-acetylmannosamine 3615-17-6 [H][C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1NC(C)=O 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 Solid Cytosol Extra-organism Periplasm logp -2.31 ALOGPS logs -0.43 ALOGPS solubility 8.25e+01 g/l ALOGPS logp -2.4 ChemAxon pka_strongest_acidic 7.38 ChemAxon pka_strongest_basic 1.46 ChemAxon iupac N-[(3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid ChemAxon average_mass 221.2078 ChemAxon mono_mass 221.089937217 ChemAxon smiles [H][C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1NC(C)=O 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 122.74 ChemAxon refractivity 47.55 ChemAxon polarizability 20.69 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Amino sugar and nucleotide sugar metabolism ec00520 <i>N</i>-acetylneuraminate and <i>N</i>-acetylmannosamine degradation PWY0-1324 Specdb::CMs 1084847 Specdb::NmrOneD 254108 Specdb::NmrOneD 254109 Specdb::NmrOneD 254110 Specdb::NmrOneD 254111 Specdb::NmrOneD 254112 Specdb::NmrOneD 254113 Specdb::NmrOneD 254114 Specdb::NmrOneD 254115 Specdb::NmrOneD 254116 Specdb::NmrOneD 254117 Specdb::NmrOneD 254118 Specdb::NmrOneD 254119 Specdb::NmrOneD 254120 Specdb::NmrOneD 254121 Specdb::NmrOneD 254122 Specdb::NmrOneD 254123 Specdb::NmrOneD 254124 Specdb::NmrOneD 254125 Specdb::NmrOneD 254126 Specdb::NmrOneD 254127 Specdb::MsMs 29603 Specdb::MsMs 29604 Specdb::MsMs 29605 Specdb::MsMs 36161 Specdb::MsMs 36162 Specdb::MsMs 36163 HMDB01129 439281 388414 C00645 17122 N-ACETYL-D-MANNOSAMINE N-Acetylmannosamine 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 Satoh, Chiyoko; Akio, Kiyomoto. Nitrogen-containing sugars. I. Synthesis of 2-acetamido-2-deoxy-D-mannose from 1-deoxy-1-nitro-D-mannitol pentaacetate. Chemical & Pharmaceutical Bulletin (1964), 12(5), 615-19. http://hmdb.ca/system/metabolites/msds/000/001/016/original/HMDB01129.pdf?1358462604 Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml N-acetylneuraminate lyase P0A6L4 NANA_ECOLI nanA http://ecmdb.ca/proteins/P0A6L4.xml UDP-N-acetylglucosamine 2-epimerase P27828 WECB_ECOLI wecB http://ecmdb.ca/proteins/P27828.xml N-acetylmannosamine kinase P45425 NANK_ECOLI nanK http://ecmdb.ca/proteins/P45425.xml PTS system mannose-specific EIIAB component P69797 PTNAB_ECOLI manX http://ecmdb.ca/proteins/P69797.xml Mannose permease IIC component P69801 PTNC_ECOLI manY http://ecmdb.ca/proteins/P69801.xml Mannose permease IID component P69805 PTND_ECOLI manZ http://ecmdb.ca/proteins/P69805.xml Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml 2-deoxyglucose-6-P phosphatase P77247 yniC http://ecmdb.ca/proteins/P77247.xml sugar phosphatas P77625 yfbT http://ecmdb.ca/proteins/P77625.xml Mannose permease IIC component P69801 PTNC_ECOLI manY http://ecmdb.ca/proteins/P69801.xml Mannose permease IID component P69805 PTND_ECOLI manZ http://ecmdb.ca/proteins/P69805.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-Acetylmannosamine > N-Acetyl-D-mannosamine 6-phosphate + Pyruvic acid TRANS-RXN0-446 N-Acetylmannosamine + Adenosine triphosphate > N-Acetyl-D-mannosamine 6-phosphate + ADP + Hydrogen ion R02705 NANK-RXN N-Acetylneuraminic acid + N-acetylneuraminate <> N-Acetylmannosamine + Pyruvic acid R01811 ACNEULY-RXN Uridine diphosphate-N-acetylglucosamine + Water <> N-Acetylmannosamine + Uridine 5'-diphosphate R00414 N-Acetylneuraminic acid <> N-Acetylmannosamine + Pyruvic acid R01811 Adenosine triphosphate + N-Acetylmannosamine <> ADP + N-Acetyl-D-mannosamine 6-phosphate R02705 N-Acetylmannosamine + Phosphate <> N-Acetyl-D-mannosamine 6-phosphate + Water R02706 N-Acetylmannosamine + Phosphoenolpyruvic acid > N-Acetyl-D-mannosamine 6-phosphate + Pyruvic acid TRANS-RXN0-446 N-acetylneuraminate > N-Acetylmannosamine + Pyruvic acid