(2S,3S,4S,5R,6R)-6-[(4-{[(2R,3S)-3-({[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}amino)-2-hydroxy-4-phenylbutyl](2-methylpropyl)sulfamoyl}phenyl)amino]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 165415
• Molecular Formular: C33H45N3O13S
• Molecular Mass: 723.7877
• Monoisotopic Mass: 723.26730952
• SMILES: O(C(=O)N[C@H]([C@@H](CN(S(=O)(=O)c1ccc(cc1)N[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)C(=O)O)O)O)O)CC(C)C)O)Cc1ccccc1)[C@H]1CO[C@@H]2[C@H]1CCO2
• Canonical SMILES: CC(CN(S(=O)(=O)c1ccc(cc1)N[C@@H]1O[C@H](C(=O)O)[C@H]([C@H]([C@H]1O)O)O)C[C@H]([C@H](Cc1ccccc1)NC(=O)O[C@H]1CO[C@@H]2[C@H]1CCO2)O)C
• InChI: InChI=1S/C33H45N3O13S/c1-18(2)15-36(50(44,45)21-10-8-20(9-11-21)34-30-28(40)26(38)27(39)29(49-30)31(41)42)16-24(37)23(14-19-6-4-3-5-7-19)35-33(43)48-25-17-47-32-22(25)12-13-46-32/h3-11,18,22-30,32,34,37-40H,12-17H2,1-2H3,(H,35,43)(H,41,42)/t22-,23-,24+,25-,26-,27-,28+,29-,30+,32+/m0/s1
• InChIKey: XXXHCLBMCZVFGB-VMMQOENWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-[(4-{[(2R,3S)-3-({[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}amino)-2-hydroxy-4-phenylbutyl](2-methylpropyl)sulfamoyl}phenyl)amino]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-[(4-{[(2R,3S)-3-({[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}amino)-2-hydroxy-4-phenylbutyl](2-methylpropyl)sulfamoyl}phenyl)amino]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-Deoxy-1-[[4-[[[(2R,3S)-3-[[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl]oxy]carbonyl]amino]-2-hydroxy-4-phenylbutyl](2-methylpropyl)amino]sulfonyl]phenyl]amino]-β-D-glucopyranuronic Acid; Darunavir N-β-D-Glucuronide

Database IDs

• CAS Number: 1159613-25-8
• PubChem SID: 162259548
• PubChem CID: 71315190

CALCULATED PROPERTIES

• H Donor: 7
• LogD (pH = 5.5): -1.4075838
• LogD (pH = 7.4): -2.4457912
• Log P: 1.024834
• Molar Refractivity: 175.3635 cm^3
• Polarizability: 70.07403 Å^3
• Polar Surface Area: 233.65 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false
• Acid pKa: 3.0329907
• H Acceptors: 13

DETAILS

Toronto Research Chemicals - D193510

A metabolite of Darunavir (D193500); an inhibitor of human immunodeficiency virus protease.

REFERENCES

• Vermeir, M. et al.: Drug Metab. Disp., 37, 809 (2009)
• Koh, Y., et al.: Antimicrob. Agents Chemother., 47, 3123 (2009)
• Arasteh, K., et al.: AIDS, 19, 943 (2009)