Showing Metabocard for UDP-alpha-D-galactofuranose (BASm0004787)
| Common Name | Udp-alpha-d-galactofuranose |
|---|---|
| Description | UDP-D-galacto-1,4-furanose is a member of the chemical class known as Pyrimidine Nucleotide Sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Uridine diphosphogalactofuranose (UDP-Galf) is the precursor of the d-galactofuranose (Galf) residues found in bacterial and parasitic cell walls, including those of many pathogens, such as Mycobacterium tuberculosis and Trypanosoma cruzi. (PMID 11573090 ) UDP-galactopyranose mutase (UGM) is a flavin-containing enzyme that catalyzes the conversion of UDP-galactopyranose to UDP-galactofuranose, the precursor of galactofuranose, which is an important cell wall component in Aspergillus fumigatus and other pathogenic microbes. (PMID 20615386 ) |
| Structure | |
| Molecular Formula | C15H24N2O17P2 |
| Average Mass | 566.30180 |
| Monoisotopic Mass | 566.05502 |
| IUPAC Name | [({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy})phosphinic acid |
| Traditional Name | {[(2r,3s,4r,5r)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy[(2r,3r,4r,5s)-5-[(1r)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxyphosphinic acid |
| CAS Registry Number | 638-23-3 |
| SMILES | O=c1ccn([C@@H]2O[C@H](COP(=O)([O-])OP(=O)([O-])O[C@H]3O[C@@H]([C@H](O)CO)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1 |
| InChI Identifier | InChI=1S/C15H24N2O17P2/c18-3-5(19)12-9(22)11(24)14(32-12)33-36(28,29)34-35(26,27)30-4-6-8(21)10(23)13(31-6)17-2-1-7(20)16-15(17)25/h1-2,5-6,8-14,18-19,21-24H,3-4H2,(H,26,27)(H,28,29)(H,16,20,25)/t5-,6-,8-,9-,10-,11-,12+,13-,14-/m1/s1 |
| InChI Key | ZQLQOXLUCGXKHS-SIAUPFDVSA-N |
| CHEBI ID | CHEBI:66915 |
| State | Solid |
| Water Solubility | 2.46e+01 g/l |
| logP | -1.31 |
| logS | -1.36 |
| pKa (Strongest Acidic) | Not Available |
| pKa (Strongest Basic) | Not Available |
| Hydrogen Acceptor Count | 15 |
| Hydrogen Donor Count | 9 |
| Polar Surface Area | 295.03 Ų |
| Rotatable Bond Count | 10 |
| Physiological Charge | Not Available |
| Formal Charge | 0 |
| Refractivity | 106.78 m³·mol⁻¹ |
| Polarizability | 46.19 |