(2S)-N-[(2S,4S,5S)-5-[2-(2,6-dimethylphenoxy)acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl]-2-(2,4-dioxo-1,3-diazinan-1-yl)-3-methylbutanamide

• ChemBase ID: 172377
• Molecular Formular: C37H46N4O6
• Molecular Mass: 642.78434
• Monoisotopic Mass: 642.34173521
• SMILES: C1CC(=O)NC(=O)N1[C@H](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](NC(=O)[C@@H](N1CCC(=O)NC1=O)C(C)C)Cc1ccccc1)O)Cc1ccccc1)COc1c(C)cccc1C
• InChI: InChI=1S/C37H46N4O6/c1-24(2)34(41-19-18-32(43)40-37(41)46)36(45)38-29(20-27-14-7-5-8-15-27)22-31(42)30(21-28-16-9-6-10-17-28)39-33(44)23-47-35-25(3)12-11-13-26(35)4/h5-17,24,29-31,34,42H,18-23H2,1-4H3,(H,38,45)(H,39,44)(H,40,43,46)/t29-,30-,31-,34-/m0/s1
• InChIKey: PSUMJBRVYHIASB-MEROQGEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(2S,4S,5S)-5-[2-(2,6-dimethylphenoxy)acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl]-2-(2,4-dioxo-1,3-diazinan-1-yl)-3-methylbutanamide
• IUPAC Traditional name: (2S)-N-[(2S,4S,5S)-5-[2-(2,6-dimethylphenoxy)acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl]-2-(2,4-dioxo-1,3-diazinan-1-yl)-3-methylbutanamide
• Synonyms: (αS)-N-[(1S,3S,4S)-4-[[(2,6-Dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-α-(1-methylethyl)-2,4-dioxo-1(2H)-pyrimidineacetami-de; Lopinavir Metabolite M-1

Database IDs

• CAS Number: 192725-39-6
• PubChem SID: 164228287
• PubChem CID: 486506

CALCULATED PROPERTIES

• Acid pKa: 11.664182
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 4.502481
• LogD (pH = 7.4): 4.502458
• Log P: 4.5024815
• Molar Refractivity: 179.2768 cm^3
• Polarizability: 69.76271 Å^3
• Polar Surface Area: 137.07 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 106-108°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L469485

A major metabolite of Lopinavir (L469480) .

REFERENCES

• Molla, A., et al.: J. Virology, 250, 255 (1998)
• Sham, H., et al.: Antimicrob. Agents Chemother., 42, 3218 (1998)
• Kumar, G., et al.: Drug Metab. Dispos., 27, 86 (1998)