Showing Metabocard for dTDP-4-amino-4,6-dideoxy-alpha-D-glucose (BASm0004879)
| Common Name | Dtdp-4-amino-4,6-dideoxy-alpha-d-glucose |
|---|---|
| Description | dTDP-D-fucosamine 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. This compound is involved in the synthesis of enterobacterial common antigen (ECA) synthesis through the reaction: dTDP-alpha-D-fucosamine + acetyl-CoA <=> dTDP-4-acetamido-4,6-dideoxy-D-galactose + coenzyme A + H+. Enterobacterial common antigen (ECA) is an outer membrane glycolipid common to all members of Enterobacteriaceae (including E. coli). The carbohydrate portion of this glycolipid consists of N-acetyl-glucosamine, N-acetyl-D-mannosaminuronic acid and 4-acetamido-4,6-dideoxy-D-galactose. These amino sugars form trisaccharide repeat units which are part of linear heteropolysaccharide chains. |
| Structure | |
| Molecular Formula | C16H27N3O14P2 |
| Average Mass | 547.34480 |
| Monoisotopic Mass | 547.09683 |
| IUPAC Name | {[(2R,3R,4S,5R,6R)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy}({[hydroxy({[3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphinic acid |
| Traditional Name | [(2r,3r,4s,5r,6r)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy({hydroxy[3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxyphosphoryl}oxy)phosphinic acid |
| CAS Registry Number | Not Available |
| SMILES | Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)([O-])OP(=O)([O-])O[C@H]3O[C@H](C)[C@@H]([NH3+])[C@H](O)[C@H]3O)O2)c(=O)[nH]c1=O |
| InChI Identifier | InChI=1S/C16H27N3O14P2/c1-6-4-19(16(24)18-14(6)23)10-3-8(20)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(17)7(2)30-15/h4,7-13,15,20-22H,3,5,17H2,1-2H3,(H,25,26)(H,27,28)(H,18,23,24)/t7-,8?,9?,10?,11+,12+,13-,15-/m1/s1 |
| InChI Key | UIVJXHWSIFBBCY-DBRXDORISA-N |
| CHEBI ID | CHEBI:68501 |
| State | Not Available |
| Water Solubility | 1.43e+01 g/l |
| logP | -1.65 |
| logS | -1.58 |
| pKa (Strongest Acidic) | Not Available |
| pKa (Strongest Basic) | Not Available |
| Hydrogen Acceptor Count | 13 |
| Hydrogen Donor Count | 7 |
| Polar Surface Area | 260.36 Ų |
| Rotatable Bond Count | 8 |
| Physiological Charge | Not Available |
| Formal Charge | 0 |
| Refractivity | 109.74 m³·mol⁻¹ |
| Polarizability | 46.89 |