2.0 2012-10-10 12:18:48 -0600 2015-06-03 17:26:01 -0600 ECMDB23145 M2MDB003535 UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diamino-heptanedioate UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diamino-heptanedioate is an intermediate in peptidoglycan synthesis. It is a substrate for UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--2,6-diaminopimelate ligase which catalyzes the addition of meso-diaminopimelic acid to the nucleotide precursor UDP-N-acetylmuramoyl-L-alanyl-D-glutamate (UMAG) in the biosynthesis of bacterial cell-wall peptidoglycan. (2S,6R)-2-4-(2R)-2-(2R)-2-(2R,3R,4R,5S,6R)-3-acetamido-2-(2R,3S,4R,5R)-5-(2,4-Dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yloxypropanoylaminopropanoylamino-4-carboxybutanoylamino-6-aminoheptanedioate (2S,6R)-2-4-(2R)-2-(2R)-2-(2R,3R,4R,5S,6R)-3-acetamido-2-(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yloxypropanoylaminopropanoylamino-4-carboxybutanoylamino-6-aminoheptanedioic acid UDP-N-Acetylmuramoyl-L-alanyl-D-g-glutamyl-meso-2,6-diamino-heptanedioate UDP-N-Acetylmuramoyl-L-alanyl-D-g-glutamyl-meso-2,6-diamino-heptanedioic acid UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diamino-heptanedioate UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diamino-heptanedioic acid UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diamino-heptanedioate UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diamino-heptanedioic acid C35H55N7O26P2 1051.79 1051.267197991 (2R,6S)-2-amino-6-{4-carboxy-4-[(2R)-2-[(2R)-2-{[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanamido]butanamido}heptanedioic acid (2R,6S)-2-amino-6-{4-carboxy-4-[(2R)-2-[(2R)-2-{[(2R,3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanamido]butanamido}heptanedioic acid C[C@@H](NC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@@H]1NC(C)=O)C(=O)NC(CCC(=O)N[C@@H](CCC[C@@H](N)C(O)=O)C(O)=O)C(O)=O InChI=1S/C35H55N7O26P2/c1-13(28(50)40-18(33(56)57)7-8-21(45)39-17(32(54)55)6-4-5-16(36)31(52)53)37-29(51)14(2)64-27-23(38-15(3)44)34(66-19(11-43)25(27)48)67-70(61,62)68-69(59,60)63-12-20-24(47)26(49)30(65-20)42-10-9-22(46)41-35(42)58/h9-10,13-14,16-20,23-27,30,34,43,47-49H,4-8,11-12,36H2,1-3H3,(H,37,51)(H,38,44)(H,39,45)(H,40,50)(H,52,53)(H,54,55)(H,56,57)(H,59,60)(H,61,62)(H,41,46,58)/t13-,14-,16-,17+,18?,19-,20-,23-,24-,25-,26-,27-,30-,34-/m1/s1 QUHLBZKCGUXHGP-YXVFMYSNSA-N logp -0.67 ALOGPS logs -2.24 ALOGPS solubility 6.03e+00 g/l ALOGPS logp -8.6 ChemAxon pka_strongest_acidic 1.5 ChemAxon pka_strongest_basic 9.3 ChemAxon iupac (2R,6S)-2-amino-6-{4-carboxy-4-[(2R)-2-[(2R)-2-{[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanamido]butanamido}heptanedioic acid ChemAxon average_mass 1051.79 ChemAxon mono_mass 1051.267197991 ChemAxon smiles C[C@@H](NC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@@H]1NC(C)=O)C(=O)NC(CCC(=O)N[C@@H](CCC[C@@H](N)C(O)=O)C(O)=O)C(O)=O ChemAxon formula C35H55N7O26P2 ChemAxon inchi InChI=1S/C35H55N7O26P2/c1-13(28(50)40-18(33(56)57)7-8-21(45)39-17(32(54)55)6-4-5-16(36)31(52)53)37-29(51)14(2)64-27-23(38-15(3)44)34(66-19(11-43)25(27)48)67-70(61,62)68-69(59,60)63-12-20-24(47)26(49)30(65-20)42-10-9-22(46)41-35(42)58/h9-10,13-14,16-20,23-27,30,34,43,47-49H,4-8,11-12,36H2,1-3H3,(H,37,51)(H,38,44)(H,39,45)(H,40,50)(H,52,53)(H,54,55)(H,56,57)(H,59,60)(H,61,62)(H,41,46,58)/t13-,14-,16-,17+,18?,19-,20-,23-,24-,25-,26-,27-,30-,34-/m1/s1 ChemAxon inchikey QUHLBZKCGUXHGP-YXVFMYSNSA-N ChemAxon polar_surface_area 514.63 ChemAxon refractivity 218.71 ChemAxon polarizability 94.79 ChemAxon rotatable_bond_count 27 ChemAxon acceptor_count 24 ChemAxon donor_count 15 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Specdb::EiMs 3239 Specdb::NmrOneD 332298 Specdb::NmrOneD 332299 Specdb::NmrOneD 332300 Specdb::NmrOneD 332301 Specdb::NmrOneD 332302 Specdb::NmrOneD 332303 Specdb::NmrOneD 332304 Specdb::NmrOneD 332305 Specdb::NmrOneD 332306 Specdb::NmrOneD 332307 Specdb::NmrOneD 332308 Specdb::NmrOneD 332309 Specdb::NmrOneD 332310 Specdb::NmrOneD 332311 Specdb::NmrOneD 332312 Specdb::NmrOneD 332313 Specdb::NmrOneD 332314 Specdb::NmrOneD 332315 Specdb::NmrOneD 332316 Specdb::NmrOneD 332317 Specdb::MsMs 37028 Specdb::MsMs 37029 Specdb::MsMs 37030 Specdb::MsMs 39476 Specdb::MsMs 39477 Specdb::MsMs 39478 53297336 C04877 28639