(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-hydroxy-2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate

• ChemBase ID: 170405
• Molecular Formular: C27H37N3O8S
• Molecular Mass: 563.66298
• Monoisotopic Mass: 563.23013616
• SMILES: O(C(=O)N[C@H]([C@@H](CN(S(=O)(=O)c1ccc(cc1)N)CC(O)(C)C)O)Cc1ccccc1)[C@H]1CO[C@@H]2[C@H]1CCO2
• Canonical SMILES: O=C(O[C@H]1CO[C@@H]2[C@H]1CCO2)N[C@H]([C@@H](CN(S(=O)(=O)c1ccc(cc1)N)CC(O)(C)C)O)Cc1ccccc1
• InChI: InChI=1S/C27H37N3O8S/c1-27(2,33)17-30(39(34,35)20-10-8-19(28)9-11-20)15-23(31)22(14-18-6-4-3-5-7-18)29-26(32)38-24-16-37-25-21(24)12-13-36-25/h3-11,21-25,31,33H,12-17,28H2,1-2H3,(H,29,32)/t21-,22-,23+,24-,25+/m0/s1
• InChIKey: XGXCRIIMIUNTCF-ARXROMJUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-hydroxy-2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate
• IUPAC Traditional name: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-hydroxy-2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate
• Synonyms: N-[3-[[(4-aminophenyl)sulfonyl](2-hydroxy-2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic Acid Hexahydrofuro[2,3-b]furan-3-yl Ester; Hydroxy Darunavir

Database IDs

• CAS Number: 1130635-75-4
• PubChem SID: 164226315
• PubChem CID: 71748962

CALCULATED PROPERTIES

• Acid pKa: 13.536352
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 1.579251
• LogD (pH = 7.4): 1.5795599
• Log P: 1.5795641
• Molar Refractivity: 143.9457 cm^3
• Polarizability: 57.123264 Å^3
• Polar Surface Area: 160.65 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H931750

A metabolite of Daranavir (D193500).

REFERENCES

• Koh, Y., et al.: Antimicrob. Agents Chemother., 47, 3123 (2003)
• Arasteh, K., et al.: AIDS, 19, 943 (2003)