(2S,3S,4S,5R,6R)-6-{[(2R,3S)-3-({[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}amino)-1-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-4-phenylbutan-2-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 165416
• 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)CC(C)C)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O)Cc1ccccc1)[C@H]1CO[C@@H]2[C@H]1CCO2
• Canonical SMILES: CC(CN(S(=O)(=O)c1ccc(cc1)N)C[C@H]([C@H](Cc1ccccc1)NC(=O)O[C@H]1CO[C@@H]2[C@H]1CCO2)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C33H45N3O13S/c1-18(2)15-36(50(43,44)21-10-8-20(34)9-11-21)16-24(47-32-28(39)26(37)27(38)29(49-32)30(40)41)23(14-19-6-4-3-5-7-19)35-33(42)48-25-17-46-31-22(25)12-13-45-31/h3-11,18,22-29,31-32,37-39H,12-17,34H2,1-2H3,(H,35,42)(H,40,41)/t22-,23-,24+,25-,26-,27-,28+,29-,31+,32+/m0/s1
• InChIKey: QZOVHLAWBUMQFG-XXNFXRIYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[(2R,3S)-3-({[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}amino)-1-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-4-phenylbutan-2-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[(2R,3S)-3-({[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}amino)-1-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-4-phenylbutan-2-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (1R,2S)-1-[[[(4-Aminophenyl)sulfonyl](2-methylpropyl)amino]methyl]-2-[[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl]oxy]carbonyl]amino]-3-phenylpropyl β-D-Glucopyranosiduronic Acid; Darunavir O-β-D-Glucuronide

Database IDs

• CAS Number: 1159613-27-0
• PubChem SID: 162259549
• PubChem CID: 71315191

CALCULATED PROPERTIES

• Acid pKa: 3.1256769
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): -1.0604439
• LogD (pH = 7.4): -2.1034553
• Log P: 0.99384135
• Molar Refractivity: 174.6213 cm^3
• Polarizability: 70.14446 Å^3
• Polar Surface Area: 236.64 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D193515

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)