methyl N-[(1R)-1-{[(2S,3S)-3-hydroxy-4-[(2R)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanehydrazido]-1-(2H5)phenylbutan-2-yl]carbamoyl}-2,2-dimethylpropyl]carbamate

• ChemBase ID: 166025
• Molecular Formular: C26H43N5O7
• Molecular Mass: 537.64892
• Monoisotopic Mass: 537.31624874
• SMILES: C(=O)(N[C@@H](C(=O)N[C@H]([C@H](CNNC(=O)[C@H](NC(=O)OC)C(C)(C)C)O)Cc1ccccc1)C(C)(C)C)OC
• Canonical SMILES: COC(=O)N[C@H](C(C)(C)C)C(=O)NNC[C@@H]([C@@H](NC(=O)[C@@H](C(C)(C)C)NC(=O)OC)Cc1ccccc1)O
• InChI: InChI=1S/C26H43N5O7/c1-25(2,3)19(29-23(35)37-7)21(33)28-17(14-16-12-10-9-11-13-16)18(32)15-27-31-22(34)20(26(4,5)6)30-24(36)38-8/h9-13,17-20,27,32H,14-15H2,1-8H3,(H,28,33)(H,29,35)(H,30,36)(H,31,34)/t17-,18-,19-,20-/m0/s1
• InChIKey: LUAXFCAWZAZCNR-MUGJNUQGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl N-[(1R)-1-{[(2S,3S)-3-hydroxy-4-[(2R)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanehydrazido]-1-(^2H₅)phenylbutan-2-yl]carbamoyl}-2,2-dimethylpropyl]carbamate
• IUPAC Traditional name: methyl N-[(1R)-1-{[(2S,3S)-3-hydroxy-4-[(2R)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanehydrazido]-1-(^2H₅)phenylbutan-2-yl]carbamoyl}-2,2-dimethylpropyl]carbamate
• Synonyms: (3S,8S,9S,12S)-3,12-Bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-[(phenyl-d5)methyl]-2,5,6,10,13-pentaazatetradecanedioic Acid 1,14-Dimethyl Ester; Des(benzylpyridyl) Atazanavir-d5

Database IDs

• PubChem SID: 162260158
• PubChem CID: 71315518

CALCULATED PROPERTIES

• Acid pKa: 12.203571
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): 2.0541718
• LogD (pH = 7.4): 2.0578246
• Log P: 2.0578778
• Molar Refractivity: 150.3008 cm^3
• Polarizability: 55.530422 Å^3
• Polar Surface Area: 167.12 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D281952

The labelled N-dealkylated metabolite (M1) of Atazanavir (A790051), a HIV protease inhibitor.

REFERENCES

• Heine, R., et al.: Drug Metab. Dispos., 37, 1826 (2009)