(2R)-2-[(2R)-2-{[(2R,3S,4S,5R,6S)-2-({[({[(2S,3R,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanoic acid

• ChemBase ID: 1448
• Molecular Formular: C23H36N4O20P2
• Molecular Mass: 750.494262
• Monoisotopic Mass: 750.13981283
• SMILES: C[C@@H](NC(=O)[C@@H](C)O[C@@H]1[C@@H](O)[C@H](CO)O[C@H](O[P@@](=O)(O)O[P@](=O)(O)OC[C@@H]2O[C@H]([C@H](O)[C@H]2O)n2ccc(=O)[nH]c2=O)[C@H]1NC(=O)C)C(=O)O
• Canonical SMILES: OC[C@@H]1O[C@H](O[P@](=O)(O[P@@](=O)(OC[C@@H]2O[C@H]([C@@H]([C@H]2O)O)n2ccc(=O)[nH]c2=O)O)O)[C@H]([C@@H]([C@H]1O)O[C@@H](C(=O)N[C@@H](C(=O)O)C)C)NC(=O)C
• InChI: 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-/m1/s1
• InChIKey: NTMMCWJNQNKACG-RXHIUOCHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(2R)-2-{[(2R,3S,4S,5R,6S)-2-({[({[(2S,3R,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanoic acid
• IUPAC Traditional name: (2R)-2-[(2R)-2-{[(2R,3S,4S,5R,6S)-2-[({[(2S,3R,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanoic acid
• Synonyms: Uridine-5'-Diphosphate-N-Acetylmuramoyl-L-Alanine

Database IDs

• PubChem SID: 46507193; 160964907
• PubChem CID: 46936185

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.7098851
• H Acceptors: 17
• H Donor: 10
• LogD (pH = 5.5): -11.562922
• LogD (pH = 7.4): -13.259777
• Log P: -5.131288
• Molar Refractivity: 150.1842 cm^3
• Polarizability: 61.424362 Å^3
• Polar Surface Area: 355.81 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.36
• LOG S: -1.89
• Solubility (Water): 9.58e+00 g/l

DETAILS

DrugBank - DB01673

Drug information: experimental