4-chloro-4-fluoro-N-[(1S)-3-{3-[3-methyl-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: 164366
• Molecular Formular: C29H41ClFN5O
• Molecular Mass: 530.1201432
• Monoisotopic Mass: 529.29836686
• SMILES: C12N(C(CC(C1)n1c(nnc1C)C(C)C)CC2)CC[C@H](NC(=O)C1CCC(CC1)(F)Cl)c1ccccc1
• Canonical SMILES: O=C(C1CCC(CC1)(F)Cl)N[C@H](c1ccccc1)CCN1C2CCC1CC(C2)n1c(C)nnc1C(C)C
• InChI: InChI=1S/C29H41ClFN5O/c1-19(2)27-34-33-20(3)36(27)25-17-23-9-10-24(18-25)35(23)16-13-26(21-7-5-4-6-8-21)32-28(37)22-11-14-29(30,31)15-12-22/h4-8,19,22-26H,9-18H2,1-3H3,(H,32,37)/t22?,23?,24?,25?,26-,29?/m0/s1
• InChIKey: NMLZEJRCFABHBR-XIXIKTKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-chloro-4-fluoro-N-[(1S)-3-{3-[3-methyl-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-chloro-4-fluoro-N-[(1S)-3-[3-(3-isopropyl-5-methyl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-phenylpropyl]cyclohexane-1-carboxamide
• Synonyms: 4-Chloro-4-fluoro-N-[(1S)-3-[(3-exo)-3-[3-methyl-5-(1-methylethyl)-4H-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]oct-8-yl]-1-phenylpropyl]cyclohexanecarboxamide; 4-Chloro Maraviroc

Database IDs

• PubChem SID: 162258501
• PubChem CID: 71314752

CALCULATED PROPERTIES

• Acid pKa: 14.422573
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.7096999
• LogD (pH = 7.4): 2.0921962
• Log P: 4.059638
• Molar Refractivity: 147.7993 cm^3
• Polarizability: 56.370872 Å^3
• Polar Surface Area: 63.05 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C367710

A chlorinated impurity of Maraviroc (M193000).

REFERENCES

• Fumero, E., et al.: Clin. Microbiol. Infect., 9, 1077 (2003)
• Walker, D.K., et al.: Drug Metab. Dispos., 33, 587 (2003)