2.0 2012-05-31 14:32:54 -0600 2015-09-17 15:41:49 -0600 ECMDB20202 M2MDB001048 UDP-N-Acetyl-D-mannosamine UDP-N-acetyl-D-mannosamine is a member of the chemical class known as Pyrimidine Nucleotide Sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. UDP-Acetylmannosamine UDP-ManNAc Uridine 5'-(trihydrogen diphosphate), P'-(2-(acetylamino)-2-deoxy-&alpha;-D-mannopyranosyl) ester Uridine 5'-(trihydrogen diphosphate), p'-(2-(acetylamino)-2-deoxy-a-D-mannopyranosyl) ester Uridine 5'-(trihydrogen diphosphate), P'-(2-(acetylamino)-2-deoxy-alpha-D-mannopyranosyl) ester Uridine 5'-(trihydrogen diphosphate), p'-(2-(acetylamino)-2-deoxy-α-D-mannopyranosyl) ester Uridine 5'-(trihydrogen diphosphoric acid), p'-(2-(acetylamino)-2-deoxy-&alpha;-D-mannopyranosyl) ester Uridine 5'-(trihydrogen diphosphoric acid), p'-(2-(acetylamino)-2-deoxy-a-D-mannopyranosyl) ester Uridine 5'-(trihydrogen diphosphoric acid), p'-(2-(acetylamino)-2-deoxy-alpha-D-mannopyranosyl) ester Uridine 5'-(trihydrogen diphosphoric acid), p'-(2-(acetylamino)-2-deoxy-α-D-mannopyranosyl) ester Uridine diphosphate <i>N</i>-acetylmannosamine Uridine diphosphate N-acetylgalactosamine Uridine diphosphate N-acetylmannosamine Uridine diphosphoric acid N-acetylgalactosamine Uridine diphosphoric acid N-acetylmannosamine Uridine diphosphoric acid n-acetylmannosamine Uridine-diphosphate-n-acetylgalactosamine Uridine-diphosphate-n-acetylglucosamine Uridine-diphosphoric acid-N-acetylgalactosamine Uridine-diphosphoric acid-N-acetylglucosamine C17H27N3O17P2 607.3537 607.081569477 N-[(3S,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid N-[(3S,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid 26575-17-7 CC(=O)N[C@@H]1[C@H](O)[C@@H](O)[C@H](CO)OC1OP(O)(=O)OP(O)(=O)OC[C@@H]1O[C@@H]([C@@H](O)[C@H]1O)N1C=CC(=O)NC1=O InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/t7-,8-,10+,11-,12-,13-,14-,15-,16?/m0/s1 LFTYTUAZOPRMMI-IUPDHGCPSA-N Cytosol logp -1.70 ALOGPS logs -1.67 ALOGPS solubility 1.30e+01 g/l ALOGPS logp -4.1 ChemAxon pka_strongest_acidic 1.73 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac N-[(3S,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid ChemAxon average_mass 607.3537 ChemAxon mono_mass 607.081569477 ChemAxon smiles CC(=O)N[C@@H]1[C@H](O)[C@@H](O)[C@H](CO)OC1OP(O)(=O)OP(O)(=O)OC[C@@H]1O[C@@H]([C@@H](O)[C@H]1O)N1C=CC(=O)NC1=O ChemAxon formula C17H27N3O17P2 ChemAxon inchi InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/t7-,8-,10+,11-,12-,13-,14-,15-,16?/m0/s1 ChemAxon inchikey LFTYTUAZOPRMMI-IUPDHGCPSA-N ChemAxon polar_surface_area 307.39 ChemAxon refractivity 118.4 ChemAxon polarizability 50.85 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 16 ChemAxon donor_count 9 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Amino sugar and nucleotide sugar metabolism ec00520 Metabolic pathways eco01100 Amino sugar and nucleotide sugar metabolism I The synthesis of amino sugars and nucleotide sugars starts with the phosphorylation of N-Acetylmuramic acid (MurNac) through its transport from the periplasmic space to the cytoplasm. Once in the cytoplasm, MurNac and water undergo a reversible reaction through a N-acetylmuramic acid 6-phosphate etherase, producing a D-lactic acid and N-Acetyl-D-Glucosamine 6-phosphate. This latter compound can also be introduced into the cytoplasm through a phosphorylating PTS permase in the inner membrane that allows for the transport of N-Acetyl-D-glucosamine from the periplasmic space. N-Acetyl-D-Glucosamine 6-phosphate can also be obtained from chitin dependent reactions. Chitin is hydrated through a bifunctional chitinase to produce chitobiose. This in turn gets hydrated by a beta-hexosaminidase to produce N-acetyl-D-glucosamine. The latter undergoes an atp dependent phosphorylation leading to the production of N-Acetyl-D-Glucosamine 6-phosphate. N-Acetyl-D-Glucosamine 6-phosphate is then be deacetylated in order to produce Glucosamine 6-phosphate through a N-acetylglucosamine-6-phosphate deacetylase. This compound can either be isomerized or deaminated into Beta-D-fructofuranose 6-phosphate through a glucosamine-fructose-6-phosphate aminotransferase and a glucosamine-6-phosphate deaminase respectively. Glucosamine 6-phosphate undergoes a reversible reaction to glucosamine 1 phosphate through a phosphoglucosamine mutase. This compound is then acetylated through a bifunctional protein glmU to produce a N-Acetyl glucosamine 1-phosphate. N-Acetyl glucosamine 1-phosphate enters the nucleotide sugar synthesis by reacting with UTP and hydrogen ion through a bifunctional protein glmU releasing pyrophosphate and a Uridine diphosphate-N-acetylglucosamine.This compound can either be isomerized into a UDP-N-acetyl-D-mannosamine or undergo a reaction with phosphoenolpyruvic acid through UDP-N-acetylglucosamine 1-carboxyvinyltransferase releasing a phosphate and a UDP-N-Acetyl-alpha-D-glucosamine-enolpyruvate. UDP-N-acetyl-D-mannosamine undergoes a NAD dependent dehydrogenation through a UDP-N-acetyl-D-mannosamine dehydrogenase, releasing NADH, a hydrogen ion and a UDP-N-Acetyl-alpha-D-mannosaminuronate, This compound is then used in the production of enterobacterial common antigens. UDP-N-Acetyl-alpha-D-glucosamine-enolpyruvate is reduced through a NADPH dependent UDP-N-acetylenolpyruvoylglucosamine reductase, releasing a NADP and a UDP-N-acetyl-alpha-D-muramate. This compound is involved in the D-glutamine and D-glutamate metabolism. PW000886 Metabolic enterobacterial common antigen biosynthesis ECASYN-PWY Specdb::MsMs 27473 Specdb::MsMs 27474 Specdb::MsMs 27475 Specdb::MsMs 34031 Specdb::MsMs 34032 Specdb::MsMs 34033 HMDB13112 449043 395672 C01170 16287 UDP-MANNAC 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 UDP-N-acetylglucosamine 2-epimerase P27828 WECB_ECOLI wecB http://ecmdb.ca/proteins/P27828.xml UDP-N-acetyl-D-mannosamine dehydrogenase P27829 WECC_ECOLI wecC http://ecmdb.ca/proteins/P27829.xml Uridine diphosphate-N-acetylglucosamine <> UDP-N-Acetyl-D-mannosamine R00420 UDPGLCNACEPIM-RXN Water + 2 NAD + UDP-N-Acetyl-D-mannosamine <>3 Hydrogen ion +2 NADH + UDP-N-Acetyl-D-mannosaminouronate R03317 UDPMANNACADEHYDROG-RXN UDP-N-Acetyl-D-mannosamine + 2 NAD + Water <> UDP-N-Acetyl-D-mannosaminouronate +2 NADH +2 Hydrogen ion R03317 UDP-N-Acetyl-D-mannosamine + NAD + Water <> UDP-N-Acetyl-D-mannosaminouronate + NADH + Hydrogen ion UDPMANNACADEHYDROG-RXN Uridine diphosphate-N-acetylglucosamine > UDP-N-Acetyl-D-mannosamine UDP-N-Acetyl-D-mannosamine + 2 NAD + Water > UDP-N-Acetyl-D-mannosaminouronate +2 NADH Uridine diphosphate-N-acetylglucosamine <> UDP-N-acetyl-D-mannosamine + UDP-N-Acetyl-D-mannosamine PW_R003315 UDP-N-acetyl-D-mannosamine + 2 NAD + Water + UDP-N-Acetyl-D-mannosamine > UDP-N-acetyl-α-D-mannosaminuronate +2 NADH +3 Hydrogen ion PW_R003316