N-[(2S,4S,5S)-5-[2-(2,6-dimethylphenoxy)acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl]-3-(2H3)methyl-2-(2-oxo-1,3-diazinan-1-yl)(2H5)butanamide

• ChemBase ID: 172376
• Molecular Formular: C37H48N4O5
• Molecular Mass: 628.80082
• Monoisotopic Mass: 628.36247066
• SMILES: C1CCNC(=O)N1C(C(=O)N[C@H](C[C@@H]([C@@H](NC(=O)COc1c(cccc1C)C)Cc1ccccc1)O)Cc1ccccc1)C(C)C
• Canonical SMILES: O=C(N[C@H]([C@H](C[C@H](Cc1ccccc1)NC(=O)C(N1CCCNC1=O)C(C)C)O)Cc1ccccc1)COc1c(C)cccc1C
• InChI: InChI=1S/C37H48N4O5/c1-25(2)34(41-20-12-19-38-37(41)45)36(44)39-30(21-28-15-7-5-8-16-28)23-32(42)31(22-29-17-9-6-10-18-29)40-33(43)24-46-35-26(3)13-11-14-27(35)4/h5-11,13-18,25,30-32,34,42H,12,19-24H2,1-4H3,(H,38,45)(H,39,44)(H,40,43)/t30-,31-,32-,34?/m0/s1
• InChIKey: KJHKTHWMRKYKJE-QZKHDZGUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,4S,5S)-5-[2-(2,6-dimethylphenoxy)acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl]-3-(^2H₃)methyl-2-(2-oxo-1,3-diazinan-1-yl)(^2H₅)butanamide
• IUPAC Traditional name: N-[(2S,4S,5S)-5-[2-(2,6-dimethylphenoxy)acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl]-3-(^2H₃)methyl-2-(2-oxo-1,3-diazinan-1-yl)(^2H₅)butanamide
• Synonyms: (αS)-N-[(1S,3S,4S)-4-[[2-(2,6-Dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-α-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetamide-d8; A 157378.0-d8; ABT 378-d8; Aluviran-d8; Koletra-d8; Lopinavir-d8

Database IDs

• PubChem SID: 164228286
• PubChem CID: 71749833

CALCULATED PROPERTIES

• Acid pKa: 13.3924265
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 4.687642
• LogD (pH = 7.4): 4.6876416
• Log P: 4.687642
• Molar Refractivity: 179.3637 cm^3
• Polarizability: 69.683624 Å^3
• Polar Surface Area: 120.0 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 97-99°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L469482

A labelled selective HIV protease inhibitor. An analogue of Ritonavir. Antiviral.

REFERENCES

• Sham, H.L., et al.: Antimicrob. Ag. Chemother., 42, 3218 (1998)
• Kumar, G.N., et al.: Drug Metab. Dispos., 27, 86 (1998)
• Murphy, R.L., et al.: Antiviral Ther., 4, Suppl. 3, 85 (1999)