4,4-difluoro-N-[(1S)-3-{3-[3-(hydroxymethyl)-5-(propan-2-yl)-4H-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]octan-8-yl}-1-phenylpropyl]cyclohexane-1-carboxamide

• ChemBase ID: 170828
• Molecular Formular: C29H41F2N5O2
• Molecular Mass: 529.6649464
• Monoisotopic Mass: 529.32283202
• SMILES: C12N(C(CC(C1)n1c(nnc1CO)C(C)C)CC2)CC[C@H](NC(=O)C1CCC(CC1)(F)F)c1ccccc1
• Canonical SMILES: OCc1nnc(n1C1CC2CCC(C1)N2CC[C@@H](c1ccccc1)NC(=O)C1CCC(CC1)(F)F)C(C)C
• InChI: InChI=1S/C29H41F2N5O2/c1-19(2)27-34-33-26(18-37)36(27)24-16-22-8-9-23(17-24)35(22)15-12-25(20-6-4-3-5-7-20)32-28(38)21-10-13-29(30,31)14-11-21/h3-7,19,21-25,37H,8-18H2,1-2H3,(H,32,38)/t22?,23?,24?,25-/m0/s1
• InChIKey: QYAXWUVUSZZECX-DGGBHQDZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,4-difluoro-N-[(1S)-3-{3-[3-(hydroxymethyl)-5-(propan-2-yl)-4H-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]octan-8-yl}-1-phenylpropyl]cyclohexane-1-carboxamide
• IUPAC Traditional name: 4,4-difluoro-N-[(1S)-3-{3-[3-(hydroxymethyl)-5-isopropyl-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]octan-8-yl}-1-phenylpropyl]cyclohexane-1-carboxamide
• Synonyms: 4,4-Difluoro-N-[(1S)-1-(4-phenyl)-3-[(3-exo)-3-[3-hydroxymethyl-5-(1-methylethyl)-4H-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]oct-8-yl]propyl]-cyclohexanecarboxamide; 3-Hydroxymethyl Maraviroc

Database IDs

• CAS Number: 1217535-55-1
• PubChem SID: 164226738
• PubChem CID: 46781826

CALCULATED PROPERTIES

• Acid pKa: 13.741707
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.5263431
• LogD (pH = 7.4): 0.88295454
• Log P: 2.8089626
• Molar Refractivity: 144.583 cm^3
• Polarizability: 54.959965 Å^3
• Polar Surface Area: 83.28 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 121-123°C

Safety Information

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

DETAILS

Toronto Research Chemicals - H947765

A metabolite of Maraviroc.

REFERENCES

• Beaumont, K., et al.: Eur. J. Pharm. Sci., 12, 41 (2000)
• Walker, D.K., et al.: Drug Metab. Dispos., 33, 587 (2005).