methyl N-[(1S)-1-{[(2S,3R)-3-hydroxy-4-[(2S)-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: 160852
• 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-SYEZAVJTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl N-[(1S)-1-{[(2S,3R)-3-hydroxy-4-[(2S)-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: methyl N-[(1S)-1-{[(2S,3R)-3-hydroxy-4-[(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethyl-N'-{[4-(pyridin-2-yl)phenyl]methyl}butanehydrazido]-1-phenylbutan-2-yl]carbamoyl}-2,2-dimethylpropyl]carbamate
• Synonyms: (3S,8R,9S,12S)-3,12-Bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-[[4-(2-pyridinyl)phenyl]methyl]-,2,5,6,10,13-pentaazatetradecanedioic Acid 1,14-Dimethyl Ester; 8-epi Atazanavir

Database IDs

• CAS Number: 1292296-09-3
• PubChem SID: 162254987
• PubChem CID: 22940470

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

DETAILS

Toronto Research Chemicals - A790055

An epimeric impurity of Atazanavir, novel azapeptide HIV protease inhibitor.

REFERENCES

• Chitturi, S.R. et al.: J. Pharmac. Biomed. Anal., 55, 31 (2011)