Showing Metabocard for UDP-N-acetyl-alpha-D-muramoyl-L-alanine (BASm0007000)
| Common Name | Udp-n-acetyl-alpha-d-muramoyl-l-alanine |
|---|---|
| Description | Udp-n-acetylmuramoyl-l-alanine belongs to the class of Pyrimidine Nucleotide Sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. (inferred from compound structure)UDP-N-acetylmuramoyl-L-alanine (UDP-MurNAc-L-Ala), which is the nucleotide substrate of the D-glutamic-acid-adding enzyme (the murD gene product) catalyzing the subsequent step in the pathway for peptidoglycan synthesis, appears to be an effector of the racemase activity. (PMID 8098327 ) MurD (UDP-N-acetylmuramoyl-L-alanine:D-glutamate ligase) is the second enzyme in the series of Mur ligases, and it catalyzes the addition of D-glutamic acid (D-Glu) to the cytoplasmic intermediate UDP-N-acetylmuramoyl-L-alanine (UMA). (PMID 19007109 ) |
| Structure | |
| Molecular Formula | C23H36N4O20P2 |
| Average Mass | 750.49430 |
| Monoisotopic Mass | 750.13981 |
| IUPAC Name | (2S)-2-{[(2R)-2-{[(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}-1-hydroxypropylidene]amino}propanoic acid |
| Traditional Name | (2s)-2-{[(2r)-2-{[(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}-1-hydroxypropyli |
| CAS Registry Number | 78738-65-5 |
| SMILES | CC(=O)N[C@H]1[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)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C(=O)N[C@@H](C)C(=O)[O-] |
| InChI Identifier | InChI=1S/C23H36N4O20P2/c1-8(21(35)36)24-19(34)9(2)43-18-14(25-10(3)29)22(45-11(6-28)16(18)32)46-49(40,41)47-48(38,39)42-7-12-15(31)17(33)20(44-12)27-5-4-13(30)26-23(27)37/h4-5,8-9,11-12,14-18,20,22,28,31-33H,6-7H2,1-3H3,(H,24,34)(H,25,29)(H,35,36)(H,38,39)(H,40,41)(H,26,30,37)/t8-,9+,11+,12+,14+,15+,16+,17+,18+,20+,22?/m0/s1 |
| InChI Key | NTMMCWJNQNKACG-CPDMUANVSA-N |
| CHEBI ID | CHEBI:83898 |
| State | Solid |
| Water Solubility | 1.73e+01 g/l |
| logP | -1.26 |
| logS | -1.64 |
| pKa (Strongest Acidic) | Not Available |
| pKa (Strongest Basic) | Not Available |
| Hydrogen Acceptor Count | 20 |
| Hydrogen Donor Count | 10 |
| Polar Surface Area | 366.28 Ų |
| Rotatable Bond Count | 15 |
| Physiological Charge | Not Available |
| Formal Charge | 0 |
| Refractivity | 151.55 m³·mol⁻¹ |
| Polarizability | 64.63 |