Showing Metabocard for 2-[(2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate (BASm0004382)
| Common Name | 2-[(2r,5z)-2-carboxy-4-methylthiazol-5(2h)-ylidene]ethyl phosphate |
|---|---|
| Description | 2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate is an intermediate involved in thiamine diphosphate biosynthesis. Thiamine diphosphate, also known as vitamin B1, is known to play a fundamental role in energy metabolism. It is an essential cofactor for a variety of enzymes such as transketolase, pyruvate dehydrogenase, pyruvate decarboxylase, and alpha-ketoglutarate dehydrogenase. Thiamine is synthesized de novo by microorganisms, plants and some lower eukaryotes (e.g. Plasmodium), but not by higher eukaryotes, which must obtain it through their diet. |
| Structure | |
| Molecular Formula | C7H7NO6PS |
| Average Mass | 264.17200 |
| Monoisotopic Mass | 263.97317 |
| IUPAC Name | (5Z)-4-methyl-5-[2-(phosphonatooxy)ethylidene]-2,5-dihydro-1,3-thiazole-2-carboxylate |
| Traditional Name | (5z)-4-methyl-5-[2-(phosphonatooxy)ethylidene]-2h-1,3-thiazole-2-carboxylate |
| CAS Registry Number | Not Available |
| SMILES | CC1=N[C@@H](C(=O)[O-])S/C1=C\COP(=O)([O-])[O-] |
| InChI Identifier | InChI=1S/C7H10NO6PS/c1-4-5(2-3-14-15(11,12)13)16-6(8-4)7(9)10/h2,6H,3H2,1H3,(H,9,10)(H2,11,12,13)/p-3/b5-2- |
| InChI Key | PQMCQNOVNFNPFJ-DJWKRKHSSA-K |
| CHEBI ID | CHEBI:62899 |
| State | Not Available |
| Water Solubility | 2.65e+01 g/l |
| logP | 0.52 |
| logS | -1.08 |
| pKa (Strongest Acidic) | Not Available |
| pKa (Strongest Basic) | Not Available |
| Hydrogen Acceptor Count | 6 |
| Hydrogen Donor Count | 0 |
| Polar Surface Area | 124.91 Ų |
| Rotatable Bond Count | 4 |
| Physiological Charge | Not Available |
| Formal Charge | -3 |
| Refractivity | 66.63 m³·mol⁻¹ |
| Polarizability | 21.87 |