2.0 2012-10-10 12:13:19 -0600 2015-06-03 17:25:46 -0600 ECMDB23030 M2MDB003420 Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol is an intermediate in peptidoglycan synthesis. It is a substrate for the enzyme undecaprenyldiphospho-muramoylpentapeptide beta-N-acetylglucosaminyltransferase which catalyzes the reaction: UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = UDP + N-acetylglucosamine-(1-4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol. Mur2ac(oyl-L-ala-g-D-glu-L-lys-D-ala-D-ala)-diphosphoundecaprenol Mur2ac(oyl-L-ala-γ-D-glu-L-lys-D-ala-D-ala)-diphosphoundecaprenol C86H143N7O21P2 1673.0374 1671.981227697 (2R)-4-{[(1S)-5-amino-1-{[(1S)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}pentyl]-C-hydroxycarbonimidoyl}-2-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5R,6R)-3-hydroxy-6-{[hydroxy({[hydroxy({[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy})phosphoryl]oxy})phosphoryl]oxy}-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene]amino}propylidene]amino}butanoic acid (2R)-4-{[(1S)-5-amino-1-{[(1S)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}pentyl]-C-hydroxycarbonimidoyl}-2-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5R,6R)-3-hydroxy-6-{[hydroxy({hydroxy[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxyphosphoryl}oxy)phosphoryl]oxy}-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene]amino}propylidene]amino}butanoic acid NCCCC[C@]([H])(N=C(O)CC[C@@]([H])(N=C(O)[C@@](C)([H])N=C(O)[C@](C)([H])O[C@@]1([H])[C@@](O)([H])[C@@]([H])(CO)O[C@]([H])(OP(O)(=O)OP(O)(=O)OC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(/C)CC\C([H])=C(/C)CCC=C(C)C)[C@]1([H])N=C(C)O)C(=O)O)C(O)=N[C@](C)([H])C(O)=N[C@@](C)([H])C(=O)O InChI=1S/C86H143N7O21P2/c1-57(2)30-20-31-58(3)32-21-33-59(4)34-22-35-60(5)36-23-37-61(6)38-24-39-62(7)40-25-41-63(8)42-26-43-64(9)44-27-45-65(10)46-28-47-66(11)48-29-49-67(12)53-55-110-115(106,107)114-116(108,109)113-86-77(91-72(17)95)79(78(97)75(56-94)112-86)111-71(16)82(100)88-69(14)81(99)93-74(85(104)105)51-52-76(96)92-73(50-18-19-54-87)83(101)89-68(13)80(98)90-70(15)84(102)103/h30,32,34,36,38,40,42,44,46,48,53,68-71,73-75,77-79,86,94,97H,18-29,31,33,35,37,39,41,43,45,47,49-52,54-56,87H2,1-17H3,(H,88,100)(H,89,101)(H,90,98)(H,91,95)(H,92,96)(H,93,99)(H,102,103)(H,104,105)(H,106,107)(H,108,109)/b58-32+,59-34+,60-36-,61-38-,62-40-,63-42-,64-44-,65-46-,66-48-,67-53-/t68-,69-,70+,71+,73-,74+,75+,77+,78+,79+,86+/m0/s1 SULOOAFLXMQJSF-NDEPDNEDSA-N Membrane logp 4.06 ALOGPS logs -6.11 ALOGPS solubility 1.30e-03 g/l ALOGPS logp 15.76 ChemAxon pka_strongest_acidic 1.71 ChemAxon pka_strongest_basic 10.21 ChemAxon iupac (2R)-4-{[(1S)-5-amino-1-{[(1S)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}pentyl]-C-hydroxycarbonimidoyl}-2-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5R,6R)-3-hydroxy-6-{[hydroxy({[hydroxy({[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy})phosphoryl]oxy})phosphoryl]oxy}-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene]amino}propylidene]amino}butanoic acid ChemAxon average_mass 1673.0374 ChemAxon mono_mass 1671.981227697 ChemAxon smiles NCCCC[C@]([H])(N=C(O)CC[C@@]([H])(N=C(O)[C@@](C)([H])N=C(O)[C@](C)([H])O[C@@]1([H])[C@@](O)([H])[C@@]([H])(CO)O[C@]([H])(OP(O)(=O)OP(O)(=O)OC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(/C)CC\C([H])=C(/C)CCC=C(C)C)[C@]1([H])N=C(C)O)C(=O)O)C(O)=N[C@](C)([H])C(O)=N[C@@](C)([H])C(=O)O ChemAxon formula C86H143N7O21P2 ChemAxon inchi InChI=1S/C86H143N7O21P2/c1-57(2)30-20-31-58(3)32-21-33-59(4)34-22-35-60(5)36-23-37-61(6)38-24-39-62(7)40-25-41-63(8)42-26-43-64(9)44-27-45-65(10)46-28-47-66(11)48-29-49-67(12)53-55-110-115(106,107)114-116(108,109)113-86-77(91-72(17)95)79(78(97)75(56-94)112-86)111-71(16)82(100)88-69(14)81(99)93-74(85(104)105)51-52-76(96)92-73(50-18-19-54-87)83(101)89-68(13)80(98)90-70(15)84(102)103/h30,32,34,36,38,40,42,44,46,48,53,68-71,73-75,77-79,86,94,97H,18-29,31,33,35,37,39,41,43,45,47,49-52,54-56,87H2,1-17H3,(H,88,100)(H,89,101)(H,90,98)(H,91,95)(H,92,96)(H,93,99)(H,102,103)(H,104,105)(H,106,107)(H,108,109)/b58-32+,59-34+,60-36-,61-38-,62-40-,63-42-,64-44-,65-46-,66-48-,67-53-/t68-,69-,70+,71+,73-,74+,75+,77+,78+,79+,86+/m0/s1 ChemAxon inchikey SULOOAFLXMQJSF-NDEPDNEDSA-N ChemAxon polar_surface_area 457.37 ChemAxon refractivity 463.45 ChemAxon polarizability 181.4 ChemAxon rotatable_bond_count 59 ChemAxon acceptor_count 25 ChemAxon donor_count 13 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Peptidoglycan biosynthesis ec00550 Metabolic pathways eco01100 Specdb::MsMs 1389214 Specdb::MsMs 1389215 Specdb::MsMs 1389216 Phospho-N-acetylmuramoyl-pentapeptide-transferase P0A6W3 MRAY_ECOLI mraY http://ecmdb.ca/proteins/P0A6W3.xml UDP-N-acetylglucosamine--N-acetylmuramyl-(pentapeptide) pyrophosphoryl-undecaprenol N-acetylglucosamine transferase P17443 MURG_ECOLI murG http://ecmdb.ca/proteins/P17443.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 Uridine diphosphate-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol > Uridine 5'-diphosphate + GlcNAc-(1->4)-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 Uridine diphosphate-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol <> Uridine 5'-diphosphate + Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-gamma-D-glutamyl-L-lysyl-D-alanyl-D-alanine R05662 R06173