(2S)-2-{[(2S,3R,4R,5R,6R)-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}-2-(phosphonooxy)propanoic acid

• ChemBase ID: 3791
• Molecular Formular: C20H32N3O23P3
• Molecular Mass: 775.395663
• Monoisotopic Mass: 775.06394419
• SMILES: CC(=O)N[C@H]1[C@@H](O[C@H](CO)[C@H](O)[C@@H]1OC(C)(OP(=O)(O)O)C(=O)O)O[P@@](=O)(O)O[P@@](=O)(O)OC[C@@H]1O[C@H]([C@H](O)[C@H]1O)n1ccc(=O)[nH]c1=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)OC(C(=O)O)(OP(=O)(O)O)C)NC(=O)C
• InChI: InChI=1S/C20H32N3O23P3/c1-7(25)21-11-15(43-20(2,18(30)31)45-47(33,34)35)13(28)8(5-24)42-17(11)44-49(38,39)46-48(36,37)40-6-9-12(27)14(29)16(41-9)23-4-3-10(26)22-19(23)32/h3-4,8-9,11-17,24,27-29H,5-6H2,1-2H3,(H,21,25)(H,30,31)(H,36,37)(H,38,39)(H,22,26,32)(H2,33,34,35)/t8-,9+,11-,12+,13+,14-,15-,16-,17+,20+/m1/s1
• InChIKey: NLBIPGBVVPCESQ-ZEVJXODCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S,3R,4R,5R,6R)-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}-2-(phosphonooxy)propanoic acid
• IUPAC Traditional name: (2S)-2-{[(2S,3R,4R,5R,6R)-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}-2-(phosphonooxy)propanoic acid
• Synonyms: 3'-1-Carboxy-1-Phosphonooxy-Ethoxy-Uridine-Diphosphate-N-Acetylglucosamine

Database IDs

• PubChem SID: 160967228; 46509124
• PubChem CID: 46936910

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.795335
• H Acceptors: 19
• H Donor: 11
• LogD (pH = 5.5): -14.381409
• LogD (pH = 7.4): -17.067093
• Log P: -5.098882
• Molar Refractivity: 145.4677 cm^3
• Polarizability: 60.0478 Å^3
• Polar Surface Area: 393.47 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.8
• LOG S: -1.76
• Solubility (Water): 1.36e+01 g/l

DETAILS

DrugBank - DB04174

Drug information: experimental