2.0 2012-10-10 12:20:05 -0600 2015-06-03 17:26:04 -0600 ECMDB23166 M2MDB003556 malonyl-CoA methyl ester Malonyl-CoA methyl ester is an intermediate in biotin synthesis. It a substrate for the enzyme Malonyl-CoA O-methyltransferase BioC which onverts the free carboxyl group of a malonyl-thioester to its methyl ester by transfer of a methyl group from S-adenosyl-L-methionine (SAM). It allows to synthesize pimeloyl-ACP via the fatty acid synthetic pathway. E.coli employs a methylation and demethylation strategy to allow elongation of a temporarily disguised malonate moiety to a pimelate moiety by the fatty acid synthetic enzymes. Methyl 3-2-3-(2R)-4-(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-2-hydroxy-3,3-dimethylbutanoylaminopropanoylaminoethylsulfanyl-3-oxopropanoate Methyl 3-2-3-(2R)-4-(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-2-hydroxy-3,3-dimethylbutanoylaminopropanoylaminoethylsulfanyl-3-oxopropanoic acid Methyl 3-2-3-(2R)-4-(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-2-hydroxy-3,3-dimethylbutanoylaminopropanoylaminoethylsulphanyl-3-oxopropanoate Methyl 3-2-3-(2R)-4-(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-2-hydroxy-3,3-dimethylbutanoylaminopropanoylaminoethylsulphanyl-3-oxopropanoic acid C25H40N7O19P3S 867.607 867.131252359 {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-{[2-({2-[(3-methoxy-3-oxopropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3R)-3-hydroxy-3-{[2-({2-[(3-methoxy-3-oxopropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxyphosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid COC(=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N InChI=1S/C25H40N7O19P3S/c1-25(2,20(37)23(38)28-5-4-14(33)27-6-7-55-16(35)8-15(34)46-3)10-48-54(44,45)51-53(42,43)47-9-13-19(50-52(39,40)41)18(36)24(49-13)32-12-31-17-21(26)29-11-30-22(17)32/h11-13,18-20,24,36-37H,4-10H2,1-3H3,(H,27,33)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,18-,19-,20+,24-/m1/s1 CHQAJZULNPRMEN-ITIYDSSPSA-N logp -0.48 ALOGPS logs -2.34 ALOGPS solubility 3.96e+00 g/l ALOGPS logp -6.9 ChemAxon pka_strongest_acidic 0.83 ChemAxon pka_strongest_basic 4.95 ChemAxon iupac {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-{[2-({2-[(3-methoxy-3-oxopropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid ChemAxon average_mass 867.607 ChemAxon mono_mass 867.131252359 ChemAxon smiles COC(=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N ChemAxon formula C25H40N7O19P3S ChemAxon inchi InChI=1S/C25H40N7O19P3S/c1-25(2,20(37)23(38)28-5-4-14(33)27-6-7-55-16(35)8-15(34)46-3)10-48-54(44,45)51-53(42,43)47-9-13-19(50-52(39,40)41)18(36)24(49-13)32-12-31-17-21(26)29-11-30-22(17)32/h11-13,18-20,24,36-37H,4-10H2,1-3H3,(H,27,33)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,18-,19-,20+,24-/m1/s1 ChemAxon inchikey CHQAJZULNPRMEN-ITIYDSSPSA-N ChemAxon polar_surface_area 389.93 ChemAxon refractivity 183.32 ChemAxon polarizability 74.61 ChemAxon rotatable_bond_count 23 ChemAxon acceptor_count 18 ChemAxon donor_count 9 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 312581 Specdb::NmrOneD 312582 Specdb::NmrOneD 312583 Specdb::NmrOneD 312584 Specdb::NmrOneD 312585 Specdb::NmrOneD 312586 Specdb::NmrOneD 312587 Specdb::NmrOneD 312588 Specdb::NmrOneD 312589 Specdb::NmrOneD 312590 Specdb::NmrOneD 312591 Specdb::NmrOneD 312592 Specdb::NmrOneD 312593 Specdb::NmrOneD 312594 Specdb::NmrOneD 312595 Specdb::NmrOneD 312596 Specdb::NmrOneD 312597 Specdb::NmrOneD 312598 Specdb::NmrOneD 312599 Specdb::NmrOneD 312600 Specdb::MsMs 27785 Specdb::MsMs 27786 Specdb::MsMs 27787 Specdb::MsMs 34343 Specdb::MsMs 34344 Specdb::MsMs 34345 46926156 C19673 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A 3-oxoacyl-[acyl-carrier-protein] synthase 1 P0A953 FABB_ECOLI fabB http://ecmdb.ca/proteins/P0A953.xml 3-oxoacyl-[acyl-carrier-protein] synthase 2 P0AAI5 FABF_ECOLI fabF http://ecmdb.ca/proteins/P0AAI5.xml Biotin synthesis protein BioC P12999 BIOC_ECOLI bioC http://ecmdb.ca/proteins/P12999.xml S-adenosyl-L-methionine + Malonyl-CoA > S-Adenosylhomocysteine + malonyl-CoA methyl ester