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

• ChemBase ID: 172378
• Molecular Formular: C37H48N4O6
• Molecular Mass: 644.80022
• Monoisotopic Mass: 644.35738528
• SMILES: C1CC(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)O
• Canonical SMILES: O=C(N[C@H]([C@H](C[C@@H](NC(=O)[C@@H](N1CCC(NC1=O)O)C(C)C)Cc1ccccc1)O)Cc1ccccc1)COc1c(C)cccc1C
• InChI: InChI=1S/C37H48N4O6/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/h5-17,24,29-32,34,42-43H,18-23H2,1-4H3,(H,38,45)(H,39,44)(H,40,46)/t29-,30-,31-,32?,34-/m0/s1
• InChIKey: HECSHMHYHYDFLR-AILSMDFESA-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-(4-hydroxy-2-oxo-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-(4-hydroxy-2-oxo-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-4-hydroxy-α-(1-methylethyl)-2-oxo-1(2H)-pyrimidine-acetamide; Lopinavir Metabolite M-3/M-4

Database IDs

• CAS Number: 357275-54-8
• PubChem SID: 164228288
• PubChem CID: 486507

CALCULATED PROPERTIES

• Acid pKa: 11.995196
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): 4.5337615
• LogD (pH = 7.4): 4.5337515
• Log P: 4.5337615
• Molar Refractivity: 179.98 cm^3
• Polarizability: 70.30828 Å^3
• Polar Surface Area: 140.23 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White to Off-White Solid
• Melting Point: 94-96°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - L469490

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)