Showing Metabocard for UDP-N-acetyl-3-O-(1-carboxyvinyl)-alpha-D-glucosamine (BASm0004876)
| Common Name | Udp-n-acetyl-3-o-(1-carboxyvinyl)-alpha-d-glucosamine |
|---|---|
| Description | UDP-n-acetyl-3-(1-carboxyvinyl)-D-glucosamine 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. |
| Structure | |
| Molecular Formula | C20H29N3O19P2 |
| Average Mass | 677.40050 |
| Monoisotopic Mass | 677.08705 |
| IUPAC Name | 2-{[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}prop-2-enoic acid |
| Traditional Name | 2-{[(2r,3r,4r,5s,6r)-2-[({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}prop-2-enoic acid |
| CAS Registry Number | 70222-94-5 |
| SMILES | C=C(O[C@H]1[C@H](O)[C@@H](CO)O[C@H](OP(=O)([O-])OP(=O)([O-])OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@@H]1NC(C)=O)C(=O)[O-] |
| InChI Identifier | InChI=1S/C20H29N3O19P2/c1-7(18(30)31)38-16-12(21-8(2)25)19(40-9(5-24)14(16)28)41-44(35,36)42-43(33,34)37-6-10-13(27)15(29)17(39-10)23-4-3-11(26)22-20(23)32/h3-4,9-10,12-17,19,24,27-29H,1,5-6H2,2H3,(H,21,25)(H,30,31)(H,33,34)(H,35,36)(H,22,26,32)/t9-,10-,12-,13-,14-,15-,16-,17-,19-/m1/s1 |
| InChI Key | BEGZZYPUNCJHKP-DBYWSUQTSA-N |
| CHEBI ID | CHEBI:68483 |
| State | Not Available |
| Water Solubility | 1.86e+01 g/l |
| logP | -1.27 |
| logS | -1.56 |
| pKa (Strongest Acidic) | Not Available |
| pKa (Strongest Basic) | Not Available |
| Hydrogen Acceptor Count | 18 |
| Hydrogen Donor Count | 9 |
| Polar Surface Area | 333.69 Ų |
| Rotatable Bond Count | 13 |
| Physiological Charge | Not Available |
| Formal Charge | 0 |
| Refractivity | 134.15 m³·mol⁻¹ |
| Polarizability | 56.58 |