sulfuric acid methyl N-[(1R)-1-{[(2S,3S)-3-hydroxy-4-[(2R)-2-[(methoxycarbonyl)amino]-3,3-dimethyl-N'-{[4-(pyridin-2-yl)phenyl]methyl}butanehydrazido]-1-phenylbutan-2-yl]carbamoyl}-2,2-dimethylpropyl]carbamate

• ChemBase ID: 160850
• Molecular Formular: C38H54N6O11S
• Molecular Mass: 802.93396
• Monoisotopic Mass: 802.35712758
• SMILES: C(=O)(N[C@@H](C(=O)N[C@H]([C@H](CN(NC(=O)[C@H](NC(=O)OC)C(C)(C)C)Cc1ccc(cc1)c1ncccc1)O)Cc1ccccc1)C(C)(C)C)OC.S(=O)(=O)(O)O
• Canonical SMILES: OS(=O)(=O)O.COC(=O)N[C@H](C(C)(C)C)C(=O)NN(Cc1ccc(cc1)c1ccccn1)C[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@@H](C(C)(C)C)NC(=O)OC)O
• InChI: InChI=1S/C38H52N6O7.H2O4S/c1-37(2,3)31(41-35(48)50-7)33(46)40-29(22-25-14-10-9-11-15-25)30(45)24-44(43-34(47)32(38(4,5)6)42-36(49)51-8)23-26-17-19-27(20-18-26)28-16-12-13-21-39-28;1-5(2,3)4/h9-21,29-32,45H,22-24H2,1-8H3,(H,40,46)(H,41,48)(H,42,49)(H,43,47);(H2,1,2,3,4)/t29-,30-,31-,32-;/m0./s1
• InChIKey: DQSGVVGOPRWTKI-WYDLTDSDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: sulfuric acid methyl N-[(1R)-1-{[(2S,3S)-3-hydroxy-4-[(2R)-2-[(methoxycarbonyl)amino]-3,3-dimethyl-N'-{[4-(pyridin-2-yl)phenyl]methyl}butanehydrazido]-1-phenylbutan-2-yl]carbamoyl}-2,2-dimethylpropyl]carbamate
• IUPAC Traditional name: sulfuric acid methyl N-[(1R)-1-{[(2S,3S)-3-hydroxy-4-[(2R)-2-[(methoxycarbonyl)amino]-3,3-dimethyl-N'-{[4-(pyridin-2-yl)phenyl]methyl}butanehydrazido]-1-phenylbutan-2-yl]carbamoyl}-2,2-dimethylpropyl]carbamate
• Synonyms: 3,12-Bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-[[4-(2-pyridinyl)phenyl]methyl]-dimethyl Ester, (3S,8S, 9S, 12S)-2,5,6,13-Pentaazatetradecanedioic Acid; BMS-232632; CGP-73547; Reyataz; Atazanavir Bisulfate SaltSee A790051

Database IDs

• CAS Number: 229975-97-7
• PubChem SID: 162254985
• PubChem CID: 71313510

CALCULATED PROPERTIES

• Acid pKa: 11.919422
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 4.5060835
• LogD (pH = 7.4): 4.5393934
• Log P: 4.5398483
• Molar Refractivity: 191.8025 cm^3
• Polarizability: 76.91037 Å^3
• Polar Surface Area: 171.22 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - A790050

Atazanavir is a novel azapeptide HIV protease inhibitor (PI). Antiviral.

REFERENCES

• Palella, F.J. Jr., et al.: N. Engl. J. Med., 338(13)
• 853 (13)
• Nolan, D., et al.: Drugs, 63(13)
• 2555 (13)
• Musial, B.L., et al.: Am. J. Health Syst. Pharm., 61, 1365 (13)
• Wood, R., et al.: J. Acquir. Immune Defic. Syndr., 36, 684 (13)