Showing Metabocard for cyclohexa-1,5-diene-1-carbonyl-CoA (BASm0002636)
| Common Name | Cyclohexa-1,5-diene-1-carbonyl-coa |
|---|---|
| Description | Cyclohex-1,5-diene-1-carboxyl-CoA is an intermediate in Benzoate degradation via CoA ligation. Biodegradation of aromatic compounds is a common process in anoxic environments. The many natural and synthetic aromatic compounds found in the environment are usually degraded by anaerobic microorganisms into only few central intermediates, prior to ring cleavage. Benzoyl-CoA is the most important of these intermediates since a large number of compounds, including chloro-, nitro-, and aminobenzoates, aromatic hydrocarbons, and phenolic compounds, are initially converted to benzoyl-CoA prior to ring reduction and cleavage. In this pathway, cyclohex-1,5-diene-1-carboxyl-CoA is generated from benzoyl-CoA via the enzyme benzoyl-CoA reductase subunit (EC 1.3.99.15) and is then converted to Cyclohex-1,4-diene-1-carboxyl-CoA. |
| Structure | |
| Molecular Formula | C28H42N7O17P3S |
| Average Mass | 873.65600 |
| Monoisotopic Mass | 873.15707 |
| IUPAC Name | {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-{[({[(3-{[2-({2-[(cyclohexa-1,5-dien-1-yl)carbonylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxy}phosphonic acid |
| Traditional Name | [(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-2-({[(3-{[2-({2-[(cyclohexa-1,5-dien-1-yl)carbonylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxyphosphonic acid |
| CAS Registry Number | 148471-94-7 |
| SMILES | CC(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-])[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C1=CCCC=C1 |
| InChI Identifier | InChI=1S/C28H42N7O17P3S/c1-28(2,22(38)25(39)31-9-8-18(36)30-10-11-56-27(40)16-6-4-3-5-7-16)13-49-55(46,47)52-54(44,45)48-12-17-21(51-53(41,42)43)20(37)26(50-17)35-15-34-19-23(29)32-14-33-24(19)35/h4,6-7,14-15,17,20-22,26,37-38H,3,5,8-13H2,1-2H3,(H,30,36)(H,31,39)(H,44,45)(H,46,47)(H2,29,32,33)(H2,41,42,43)/t17-,20-,21-,22?,26-/m1/s1 |
| InChI Key | IHXBZDHPKCDGKN-VBDPZXIHSA-N |
| CHEBI ID | CHEBI:57374 |
| HMDB ID | HMDB0012207 |
| State | Solid |
| Water Solubility | 3.49e+00 g/l |
| logP | 0.14 |
| logS | -2.40 |
| pKa (Strongest Acidic) | 0.83 |
| pKa (Strongest Basic) | 4.95 |
| Hydrogen Acceptor Count | 17 |
| Hydrogen Donor Count | 9 |
| Polar Surface Area | 363.63 Ų |
| Rotatable Bond Count | 21 |
| Physiological Charge | -4 |
| Formal Charge | 0 |
| Refractivity | 195.40 m³·mol⁻¹ |
| Polarizability | 78.59 |