2.0 2012-10-10 12:18:29 -0600 2015-06-03 17:26:00 -0600 ECMDB23138 M2MDB003528 UDP-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala) UDP-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala) is an intermediate in peptidoglycan biosynthesis. It is substrate for the enzyme Phospho-N-acetylmuramoyl-pentapeptide-transferase which catalyzes the first step of the lipid cycle reactions in the biosynthesis of the cell wall peptidoglycan. The reaction is UDP-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala) + undecaprenyl phosphate = UMP + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol. UDP-Mur2Ac(oyl-L-Ala-g-D-Glu-L-Lys-D-Ala-D-Ala) UDP-Mur2ac(oyl-L-ala-γ-D-glu-L-lys-D-ala-D-ala) UDP-N-Acetylmuramoyl-L-alanyl-g-D-glutamyl-L-lysyl-D-alanyl-D-alanine UDP-N-acetylmuramoyl-L-alanyl-gamma-D-glutamyl-L-lysyl-D-alanyl-D-alanine UDP-N-Acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine C40H62N9O26P2 1146.9125 1146.328121225 (4S)-N-[(1S)-5-amino-1-{[(1S)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}pentyl]-4-carboxy-4-{[(2S)-2-{[(2R)-2-{[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-4-yl]oxy}-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}butanecarboximidate (4S)-N-[(1S)-5-amino-1-{[(1S)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}pentyl]-4-carboxy-4-{[(2S)-2-{[(2R)-2-{[(2R,3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-4-yl]oxy}-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}butanecarboximidate [H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC([O-])=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(C)[O-])C(O)=N[C@@]([H])(C)C(O)=N[C@@]([H])(CCC([O-])=N[C@@]([H])(CCCCN)C(O)=N[C@@]([H])(C)C(O)=N[C@]([H])(C)C(O)=O)C(O)=O InChI=1S/C40H65N9O26P2/c1-16(32(57)44-18(3)37(61)62)43-35(60)21(8-6-7-12-41)46-25(52)10-9-22(38(63)64)47-33(58)17(2)42-34(59)19(4)71-31-27(45-20(5)51)39(73-23(14-50)29(31)55)74-77(68,69)75-76(66,67)70-15-24-28(54)30(56)36(72-24)49-13-11-26(53)48-40(49)65/h11,13,16-19,21-24,27-31,36,39,50,54-56H,6-10,12,14-15,41H2,1-5H3,(H,42,59)(H,43,60)(H,44,57)(H,45,51)(H,46,52)(H,47,58)(H,61,62)(H,63,64)(H,66,67)(H,68,69)(H,48,53,65)/p-3/t16-,17-,18+,19+,21-,22-,23+,24+,27+,28+,29+,30+,31+,36+,39+/m0/s1 PFMVORMCVGOQKR-MZSDELDXSA-K logp -0.57 ALOGPS logs -3.45 ALOGPS solubility 4.28e-01 g/l ALOGPS logp -3.7 ChemAxon pka_strongest_acidic 1.71 ChemAxon pka_strongest_basic 10.21 ChemAxon iupac (4S)-N-[(1S)-5-amino-1-{[(1S)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}pentyl]-4-carboxy-4-{[(2S)-2-{[(2R)-2-{[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-4-yl]oxy}-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}butanecarboximidate ChemAxon average_mass 1146.9125 ChemAxon mono_mass 1146.328121225 ChemAxon smiles [H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC([O-])=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(C)[O-])C(O)=N[C@@]([H])(C)C(O)=N[C@@]([H])(CCC([O-])=N[C@@]([H])(CCCCN)C(O)=N[C@@]([H])(C)C(O)=N[C@]([H])(C)C(O)=O)C(O)=O ChemAxon formula C40H62N9O26P2 ChemAxon inchi InChI=1S/C40H65N9O26P2/c1-16(32(57)44-18(3)37(61)62)43-35(60)21(8-6-7-12-41)46-25(52)10-9-22(38(63)64)47-33(58)17(2)42-34(59)19(4)71-31-27(45-20(5)51)39(73-23(14-50)29(31)55)74-77(68,69)75-76(66,67)70-15-24-28(54)30(56)36(72-24)49-13-11-26(53)48-40(49)65/h11,13,16-19,21-24,27-31,36,39,50,54-56H,6-10,12,14-15,41H2,1-5H3,(H,42,59)(H,43,60)(H,44,57)(H,45,51)(H,46,52)(H,47,58)(H,61,62)(H,63,64)(H,66,67)(H,68,69)(H,48,53,65)/p-3/t16-,17-,18+,19+,21-,22-,23+,24+,27+,28+,29+,30+,31+,36+,39+/m0/s1 ChemAxon inchikey PFMVORMCVGOQKR-MZSDELDXSA-K ChemAxon polar_surface_area 568.45 ChemAxon refractivity 282.58 ChemAxon polarizability 105.43 ChemAxon rotatable_bond_count 30 ChemAxon acceptor_count 31 ChemAxon donor_count 13 ChemAxon physiological_charge -3 ChemAxon formal_charge -3 ChemAxon Peptidoglycan biosynthesis ec00550 Metabolic pathways eco01100 Specdb::NmrOneD 290335 Specdb::NmrOneD 290336 Specdb::NmrOneD 290337 Specdb::NmrOneD 290338 Specdb::NmrOneD 290339 Specdb::NmrOneD 290340 Specdb::NmrOneD 290341 Specdb::NmrOneD 290342 Specdb::NmrOneD 290343 Specdb::NmrOneD 290344 Specdb::NmrOneD 290345 Specdb::NmrOneD 290346 Specdb::NmrOneD 290347 Specdb::NmrOneD 290348 Specdb::NmrOneD 290349 Specdb::NmrOneD 290350 Specdb::NmrOneD 290351 Specdb::NmrOneD 290352 Specdb::NmrOneD 290353 Specdb::NmrOneD 290354 Specdb::MsMs 37223 Specdb::MsMs 37224 Specdb::MsMs 37225 Specdb::MsMs 39671 Specdb::MsMs 39672 Specdb::MsMs 39673 Phospho-N-acetylmuramoyl-pentapeptide-transferase P0A6W3 MRAY_ECOLI mraY http://ecmdb.ca/proteins/P0A6W3.xml UDP-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala) + di-trans,octa-cis-undecaprenyl phosphate > Uridine 5'-monophosphate + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine + Di-trans,poly-cis-undecaprenyl phosphate + UDP-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala) <> Uridine 5'-monophosphate + MurAc(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala)-diphospho-undecaprenol + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol R05629