2.0 2012-05-31 13:45:38 -0600 2015-06-03 15:53:45 -0600 ECMDB01121 M2MDB000261 N-Acetyl-D-mannosamine 6-phosphate N-Acetyl-D-mannosamine 6-phosphate is an intermediate in amino sugar metabolism and is a substrate for UDP-N-acetylglucosamine--peptide N-acetylglucosaminyltransferase, Bifunctional UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase, Alpha-N-acetylglucosaminidase and Exostosin-2. It can be generated from N-acetyl-neuraminate-9-phosphate or N-acetyl-D-mannosamine. N-acetyl-D-mannosamine-6-P N-acetyl-mannosamine-6-P N-acetyl-mannosamine-6-phosphate N-acetylmannosamine-6-P ManNAc-6-P ManNAc6P N-Acetyl-D-mannosamine 6-phosphate N-Acetyl-D-mannosamine 6-phosphoric acid N-Acetyl-D-mannosamine-6-P N-Acetyl-D-mannosamine-6-phosphate N-Acetyl-D-mannosamine-6-phosphoric acid N-Acetyl-mannosamine-6-P N-Acetyl-mannosamine-6-phosphate n-Acetyl-mannosamine-6-phosphoric acid N-Acetyl-mannosamine-6-phosphoric acid N-Acetylmannosamine-6-P C8H16NO9P 301.1877 301.056267627 {[(2R,3S,4R,5S,6S)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid [(2R,3S,4R,5S,6S)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxyphosphonic acid 873185-52-5 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-UOLFYFMNSA-N Solid Cytosol logp -2.02 ALOGPS logs -1.23 ALOGPS solubility 1.76e+01 g/l ALOGPS logp -3.3 ChemAxon pka_strongest_acidic 1.23 ChemAxon pka_strongest_basic -0.79 ChemAxon iupac {[(2R,3S,4R,5S,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-UOLFYFMNSA-N ChemAxon polar_surface_area 165.78 ChemAxon refractivity 57.9 ChemAxon polarizability 25.24 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 8 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Amino sugar and nucleotide sugar metabolism ec00520 N-acetylneuraminate and N-acetylmannosamine and N-acetylglucosamine degradation The degradation of N-acetylneuraminate begins with its incorporation into the cytosol through a hydrogen symporter. Once inside the cytosol it is degraded by a N-acetylneuraminate lyase resulting in a release of a pyruvic acid and N-acetymannosamine. The latter compound is phosphorylated by an ATP driven N-Acetylmannosamine kinase resulting in the release of an ADP, a hydrogen ion and a N-Acetyl-D-mannosamine 6-phosphate. This phosphorylated compound is then metabolized by a putative N-acetylmannosamine-6-phosphate 2-epimerase resulting in the release of a N-Acetyl-D-glucosamine 6-phosphate. This compound is then deacetylated through a N-acetylglucosamine-6-phosphate deacetylase resulting in the release of an Acetic acid and a glucosamine 6-phosphate This compound can then be deaminated through a glucosamine-6-phosphate deaminase resulting in the release of an ammonium and a beta-D-fructofuranose 6-phosphate which can then be incorporated into the glycolysis pathway. PW002030 Metabolic N-acetylneuraminate and N-acetylmannosamine degradation PWY0-1324 Specdb::CMs 21357 Specdb::CMs 37933 Specdb::CMs 134565 Specdb::CMs 142299 Specdb::NmrOneD 146470 Specdb::NmrOneD 146471 Specdb::NmrOneD 146472 Specdb::NmrOneD 146473 Specdb::NmrOneD 146474 Specdb::NmrOneD 146475 Specdb::NmrOneD 146476 Specdb::NmrOneD 146477 Specdb::NmrOneD 146478 Specdb::NmrOneD 146479 Specdb::NmrOneD 146480 Specdb::NmrOneD 146481 Specdb::NmrOneD 146482 Specdb::NmrOneD 146483 Specdb::NmrOneD 146484 Specdb::NmrOneD 146485 Specdb::NmrOneD 146486 Specdb::NmrOneD 146487 Specdb::NmrOneD 146488 Specdb::NmrOneD 146489 Specdb::MsMs 27989 Specdb::MsMs 27990 Specdb::MsMs 27991 Specdb::MsMs 34547 Specdb::MsMs 34548 Specdb::MsMs 34549 Specdb::MsMs 2348060 Specdb::MsMs 2348061 Specdb::MsMs 2348062 Specdb::MsMs 2587489 Specdb::MsMs 2587490 Specdb::MsMs 2587491 HMDB01121 440273 389249 C04257 N-ACETYL-D-MANNOSAMINE-6P BMX 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 Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml Putative N-acetylmannosamine-6-phosphate 2-epimerase P0A761 NANE_ECOLI nanE http://ecmdb.ca/proteins/P0A761.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 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-Acetyl-D-mannosamine 6-phosphate <> N-Acetyl-D-Glucosamine 6-Phosphate R02087 NANE-RXN N-Acetyl-D-Glucosamine 6-Phosphate <> N-Acetyl-D-mannosamine 6-phosphate R02087 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-Acetylmannosamine + Adenosine triphosphate > ADP + Hydrogen ion + N-Acetyl-D-mannosamine 6-phosphate PW_R005937