Showing Metabocard for beta-L-fucose 1-phosphate (BASm0002543)
| Common Name | Beta-l-fucose 1-phosphate | ||||||||
|---|---|---|---|---|---|---|---|---|---|
| Description | Fucose 1-phosphate (CAS: 16562-58-6) belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphate group linked to the carbohydrate unit. Fucose 1-phosphate is an intermediate in the reversible synthesis of GDP-L-fucose catalyzed by the enzyme guanosine triphosphate fucose pyrophosphorylase (GFPP, EC 2.7.7.30). The reversible reaction is magnesium-dependent, although the enzyme is partially active when cobalt or manganese is substituted. The reaction is unusual in that, of the four canonical nucleoside triphosphates, only guanosine can be utilized efficiently to form a nucleotide-sugar. Free cytosolic fucose is phosphorylated by L-fucokinase (EC 2.7.1.52) to form fucose-1-phosphate in the salvage pathway of GDP-L-fucose (PMID: 16185085 , 14686921 ). | ||||||||
| Structure | |||||||||
| Molecular Formula | C6H13O8P | ||||||||
| Average Mass | 244.13600 | ||||||||
| Monoisotopic Mass | 244.03480 | ||||||||
| IUPAC Name | {[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phosphonic acid | ||||||||
| Traditional Name | [(3s,4r,5s,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphosphonic acid | ||||||||
| CAS Registry Number | 16562-59-7 | ||||||||
| SMILES | C[C@@H]1O[C@H](OP(=O)([O-])[O-])[C@@H](O)[C@H](O)[C@@H]1O | ||||||||
| InChI Identifier | InChI=1S/C6H13O8P/c1-2-3(7)4(8)5(9)6(13-2)14-15(10,11)12/h2-9H,1H3,(H2,10,11,12)/t2-,3+,4+,5-,6+/m0/s1 | ||||||||
| InChI Key | PTVXQARCLQPGIR-SXUWKVJYSA-N | ||||||||
| CHEBI ID | CHEBI:57268 | ||||||||
| HMDB ID | HMDB0001265 | ||||||||
| Pathways |
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| State | Solid | ||||||||
| Water Solubility | 3.42e+01 g/l | ||||||||
| logP | -1.53 | ||||||||
| logS | -0.85 | ||||||||
| pKa (Strongest Acidic) | 1.16 | ||||||||
| pKa (Strongest Basic) | -3.61 | ||||||||
| Hydrogen Acceptor Count | 7 | ||||||||
| Hydrogen Donor Count | 5 | ||||||||
| Polar Surface Area | 136.68 Ų | ||||||||
| Rotatable Bond Count | 2 | ||||||||
| Physiological Charge | -2 | ||||||||
| Formal Charge | 0 | ||||||||
| Refractivity | 45.25 m³·mol⁻¹ | ||||||||
| Polarizability | 19.71 |