2.0 2012-05-31 14:07:06 -0600 2015-06-03 15:54:49 -0600 ECMDB04167 M2MDB000647 UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine UDP-n-acetyl-3-(1-carboxyvinyl)-D-glucosamine 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. Enolpyruvyl-UDP-N-acetylglucosamine EP-UDPGlCNAC UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine UDP-N-acetylglucosamine-3-O-pyruvate ether UDP-GlcNAc-enolpyruvate UDP-GlcNAc-enolpyruvic acid UDP-GlcNAc-pyruvate enol ether UDP-GlcNAc-pyruvic acid enol ether UDP-GlcNacPyrEE UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine UDP-N-Acetyl-3-O-(1-carboxyvinyl)-D-glucosamine UDP-N-Acetylenolpyruvylglucosamine UDP-N-Acetylglucosamine enolpyruvate UDP-N-Acetylglucosamine enolpyruvic acid UDP-N-Acetylglucosamine-3-O-pyruvate ether UDP-N-Acetylglucosamine-3-O-pyruvateether UDP-N-Acetylglucosamine-3-O-pyruvic acid ether UdPGNAC-enolpyruvate UdPGNAC-enolpyruvic acid UNAGEP C20H29N3O19P2 677.4005 677.087048785 2-{[(2R,3R,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)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}prop-2-enoic acid 2-{[(2R,3R,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]-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}prop-2-enoic acid 70222-94-5 [H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(OC(=C)C(O)=O)[C@@]2([H])N=C(C)O)O[C@@]([H])(N2C=CC(O)=NC2=O)[C@]([H])(O)[C@]1([H])O InChI=1S/C20H29N3O19P2/c1-7(18(30)31)38-16-12(21-8(2)25)19(40-9(5-24)14(16)28)41-44(35,36)42-43(33,34)37-6-10-13(27)15(29)17(39-10)23-4-3-11(26)22-20(23)32/h3-4,9-10,12-17,19,24,27-29H,1,5-6H2,2H3,(H,21,25)(H,30,31)(H,33,34)(H,35,36)(H,22,26,32)/t9-,10-,12-,13-,14-,15-,16-,17-,19-/m1/s1 BEGZZYPUNCJHKP-DBYWSUQTSA-N Cytosol logp -1.27 ALOGPS logs -1.56 ALOGPS solubility 1.86e+01 g/l ALOGPS logp -3.5 ChemAxon pka_strongest_acidic 1.73 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac 2-{[(2R,3R,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)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}prop-2-enoic acid ChemAxon average_mass 677.4005 ChemAxon mono_mass 677.087048785 ChemAxon smiles [H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(OC(=C)C(O)=O)[C@@]2([H])N=C(C)O)O[C@@]([H])(N2C=CC(O)=NC2=O)[C@]([H])(O)[C@]1([H])O ChemAxon formula C20H29N3O19P2 ChemAxon inchi InChI=1S/C20H29N3O19P2/c1-7(18(30)31)38-16-12(21-8(2)25)19(40-9(5-24)14(16)28)41-44(35,36)42-43(33,34)37-6-10-13(27)15(29)17(39-10)23-4-3-11(26)22-20(23)32/h3-4,9-10,12-17,19,24,27-29H,1,5-6H2,2H3,(H,21,25)(H,30,31)(H,33,34)(H,35,36)(H,22,26,32)/t9-,10-,12-,13-,14-,15-,16-,17-,19-/m1/s1 ChemAxon inchikey BEGZZYPUNCJHKP-DBYWSUQTSA-N ChemAxon polar_surface_area 333.69 ChemAxon refractivity 134.15 ChemAxon polarizability 56.58 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 18 ChemAxon donor_count 9 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Amino sugar and nucleotide sugar metabolism ec00520 Peptidoglycan biosynthesis ec00550 Metabolic pathways eco01100 UDP-N-acetylmuramoyl-pentapeptide biosynthesis III (meso-DAP-containing) PWY-6387 Specdb::CMs 1083663 Specdb::NmrOneD 342668 Specdb::NmrOneD 342669 Specdb::NmrOneD 342670 Specdb::NmrOneD 342671 Specdb::NmrOneD 342672 Specdb::NmrOneD 342673 Specdb::NmrOneD 342674 Specdb::NmrOneD 342675 Specdb::NmrOneD 342676 Specdb::NmrOneD 342677 Specdb::NmrOneD 342678 Specdb::NmrOneD 342679 Specdb::NmrOneD 342680 Specdb::NmrOneD 342681 Specdb::NmrOneD 342682 Specdb::NmrOneD 342683 Specdb::NmrOneD 342684 Specdb::NmrOneD 342685 Specdb::NmrOneD 342686 Specdb::NmrOneD 342687 Specdb::MsMs 25889 Specdb::MsMs 25890 Specdb::MsMs 25891 Specdb::MsMs 32447 Specdb::MsMs 32448 Specdb::MsMs 32449 172502 10128141 C04631 16435 UDP-ACETYL-CARBOXYVINYL-GLUCOSAMINE EPU 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 UDP-N-acetylenolpyruvoylglucosamine reductase P08373 MURB_ECOLI murB http://ecmdb.ca/proteins/P08373.xml UDP-N-acetylglucosamine 1-carboxyvinyltransferase P0A749 MURA_ECOLI murA http://ecmdb.ca/proteins/P0A749.xml Phosphoenolpyruvic acid + Uridine diphosphate-N-acetylglucosamine <> Phosphate + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine R00660 UDPNACETYLGLUCOSAMENOLPYRTRANS-RXN Hydrogen ion + NADPH + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine <> NADP + UDP-N-Acetylmuraminate R03192 UDPNACETYLMURAMATEDEHYDROG-RXN UDP-N-Acetylmuraminate + NAD <> UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + NADH + Hydrogen ion R03191 UDP-N-Acetylmuraminate + NADP <> UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + NADPH + Hydrogen ion R03192 Uridine diphosphate-N-acetylglucosamine + Phosphoenolpyruvic acid > UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + Phosphate UDPNACETYLGLUCOSAMENOLPYRTRANS-RXN NADP + UDP-N-Acetylmuraminate < Hydrogen ion + NADPH + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine UDPNACETYLMURAMATEDEHYDROG-RXN Phosphoenolpyruvic acid + Uridine diphosphate-N-acetylglucosamine > Inorganic phosphate + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine UDP-N-Acetylmuraminate + NADP > UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + NADPH Hydrogen ion + NADPH + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine <> NADP + UDP-N-Acetylmuraminate UDP-N-Acetylmuraminate + NAD <> UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + NADH + Hydrogen ion Phosphoenolpyruvic acid + Uridine diphosphate-N-acetylglucosamine <> Phosphate + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine Hydrogen ion + NADPH + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine <> NADP + UDP-N-Acetylmuraminate