Showing Metabocard for malonyl-CoA methyl ester (BASm0004993)
| Common Name | Malonyl-coa methyl ester |
|---|---|
| Description | 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. |
| Structure | |
| Molecular Formula | C25H40N7O19P3S |
| Average Mass | 867.60700 |
| Monoisotopic Mass | 867.13125 |
| IUPAC Name | (2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-[2-({2-[(3-methoxy-3-oxopropanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidic acid |
| Traditional Name | (2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-n-[2-({2-[(3-methoxy-3-oxopropanoyl)sulfanyl]ethyl}-c-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidic |
| CAS Registry Number | Not Available |
| SMILES | COC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)([O-])[O-] |
| InChI Identifier | 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 |
| InChI Key | CHQAJZULNPRMEN-ITIYDSSPSA-N |
| CHEBI ID | CHEBI:71242 |
| State | Not Available |
| Water Solubility | 5.95e+00 g/l |
| logP | -0.40 |
| logS | -2.16 |
| pKa (Strongest Acidic) | Not Available |
| pKa (Strongest Basic) | Not Available |
| Hydrogen Acceptor Count | 20 |
| Hydrogen Donor Count | 9 |
| Polar Surface Area | 396.91 Ų |
| Rotatable Bond Count | 23 |
| Physiological Charge | Not Available |
| Formal Charge | 0 |
| Refractivity | 184.36 m³·mol⁻¹ |
| Polarizability | 75.95 |