Showing Metabocard for 3-oxo-5,6-dehydrosuberyl-CoA semialdehyde (BASm0004418)
| Common Name | 3-oxo-5,6-dehydrosuberyl-coa semialdehyde |
|---|---|
| Description | 3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde is an intermediate in phenylacetate metabolism. It is a substrate for the enzyme known as Bifunctional protein PaaZ. This enzyme consists of a C-terminal (R)-specific enoyl-CoA hydratase domain (formerly MaoC) that cleaves the phenylacetate ring and produces the highly reactive 3-oxo-5,6-dehydrosuberyl-CoA semialdehyde and an N-terminal NADP-dependent aldehyde dehydrogenase domain that oxidizes the aldehyde to 3-oxo-5,6-dehydrosuberyl-CoA. |
| Structure | |
| Molecular Formula | C29H44N7O19P3S |
| Average Mass | 919.68100 |
| Monoisotopic Mass | 919.16255 |
| 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)-N-{2-[(2-{[(5Z)-3,8-dioxooct-5-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-2-hydroxy-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]-n-{2-[(2-{[(5z)-3,8-dioxooct-5-enoyl]sulfanyl}ethyl)-c-hydroxycarbonimidoyl]ethyl}-2-hydroxy-3,3-dimethylbutanimidi |
| CAS Registry Number | Not Available |
| 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)CC(=O)CC=CCC=O |
| InChI Identifier | InChI=1S/C29H44N7O19P3S/c1-29(2,24(42)27(43)32-8-7-19(39)31-9-11-59-20(40)12-17(38)6-4-3-5-10-37)14-52-58(49,50)55-57(47,48)51-13-18-23(54-56(44,45)46)22(41)28(53-18)36-16-35-21-25(30)33-15-34-26(21)36/h3-4,10,15-16,18,22-24,28,41-42H,5-9,11-14H2,1-2H3,(H,31,39)(H,32,43)(H,47,48)(H,49,50)(H2,30,33,34)(H2,44,45,46)/b4-3-/t18-,22-,23-,24+,28-/m1/s1 |
| InChI Key | XYGQIZWAZKPGNV-ZVEAYUPDSA-N |
| CHEBI ID | CHEBI:63257 |
| State | Not Available |
| Water Solubility | 5.04e+00 g/l |
| logP | 0.38 |
| logS | -2.26 |
| pKa (Strongest Acidic) | Not Available |
| pKa (Strongest Basic) | Not Available |
| Hydrogen Acceptor Count | 21 |
| Hydrogen Donor Count | 9 |
| Polar Surface Area | 404.75 Ų |
| Rotatable Bond Count | 26 |
| Physiological Charge | Not Available |
| Formal Charge | 0 |
| Refractivity | 203.43 m³·mol⁻¹ |
| Polarizability | 82.39 |