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-(2H5)phenylbutan-2-yl]carbamoyl}-2,2-dimethylpropyl]carbamate

• ChemBase ID: 160851
• Molecular Formular: C38H52N6O7
• Molecular Mass: 704.85548
• Monoisotopic Mass: 704.38974803
• 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
• Canonical SMILES: 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/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/h9-21,29-32,45H,22-24H2,1-8H3,(H,40,46)(H,41,48)(H,42,49)(H,43,47)/t29-,30-,31-,32-/m0/s1
• InChIKey: AXRYRYVKAWYZBR-YDPTYEFTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 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-(^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-dimethyl-N'-{[4-(pyridin-2-yl)phenyl]methyl}butanehydrazido]-1-(^2H₅)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-d5; BMS-232632-d5; CGP-73547-d5; Atazanavir-d5

Database IDs

• PubChem SID: 162254986
• PubChem CID: 71313512

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: 76.93214 Å^3
• Polar Surface Area: 171.22 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 197-200°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A790052

Atazanavir is a novel azapeptide HIV protease inhibitor (PI). Antiviral. Like other antiretrovirals, it is used to treat infection of human immunodeficiency virus (HIV). Newer research has been investigating the potential anticancer effects of atazanavir

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)