(2R,3S)-3-amino-S-(4-aminophenyl)-2-hydroxy-N-[2-(2H3)methyl(2H6)propyl]-4-phenylbutane-1-sulfonamido

• ChemBase ID: 159718
• Molecular Formular: C20H29N3O3S
• Molecular Mass: 391.52756
• Monoisotopic Mass: 391.1929628
• SMILES: c1c(ccc(c1)S(=O)(=O)N(C[C@H]([C@H](Cc1ccccc1)N)O)CC(C)C)N
• Canonical SMILES: CC(CN(S(=O)(=O)c1ccc(cc1)N)C[C@H]([C@H](Cc1ccccc1)N)O)C
• InChI: InChI=1S/C20H29N3O3S/c1-15(2)13-23(27(25,26)18-10-8-17(21)9-11-18)14-20(24)19(22)12-16-6-4-3-5-7-16/h3-11,15,19-20,24H,12-14,21-22H2,1-2H3/t19-,20+/m0/s1
• InChIKey: NUMJNKDUHFCFJO-VQTJNVASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-3-amino-S-(4-aminophenyl)-2-hydroxy-N-[2-(^2H₃)methyl(^2H₆)propyl]-4-phenylbutane-1-sulfonamido
• IUPAC Traditional name: (2R,3S)-3-amino-S-(4-aminophenyl)-2-hydroxy-N-[2-(^2H₃)methyl(^2H₆)propyl]-4-phenylbutane-1-sulfonamido
• Synonyms: 4-Amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl-d9)benzenesulfonamide; 4-Amino-N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-(isobutyl-d9)benzenesulfonamide

Database IDs

• PubChem SID: 162253853
• PubChem CID: 25269885

CALCULATED PROPERTIES

• Acid pKa: 14.179071
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.8227055
• LogD (pH = 7.4): 0.47667664
• Log P: 2.0875885
• Molar Refractivity: 109.404 cm^3
• Polarizability: 43.13391 Å^3
• Polar Surface Area: 109.65 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A581402

A labelled metabolite of Darunavir.

REFERENCES

• Debouck, C., et al.: Drug Dev. Res., 21, 1 (1990)
• Krohn, A., et al.: J. Med. Chem., 34, 3340 (1990)
• Vazquez, M., et al.: J. Med. Chem., 38, 581 (1990)