[(2-chlorophenyl)methyl]({[(1r,4r)-4-({[(2-chlorophenyl)methyl]amino}methyl)cyclohexyl]methyl})amine

• ChemBase ID: 160900
• Molecular Formular: C22H28Cl2N2
• Molecular Mass: 391.37712
• Monoisotopic Mass: 390.16295427
• SMILES: c1cc(c(cc1)CNC[C@H]1CC[C@@H](CC1)CNCc1c(cccc1)Cl)Cl
• Canonical SMILES: Clc1ccccc1CNC[C@@H]1CC[C@H](CC1)CNCc1ccccc1Cl
• InChI: InChI=1S/C22H28Cl2N2/c23-21-7-3-1-5-19(21)15-25-13-17-9-11-18(12-10-17)14-26-16-20-6-2-4-8-22(20)24/h1-8,17-18,25-26H,9-16H2/t17-,18-
• InChIKey: RZRPZWGIOOZIBE-IYARVYRRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2-chlorophenyl)methyl]({[(1r,4r)-4-({[(2-chlorophenyl)methyl]amino}methyl)cyclohexyl]methyl})amine
• IUPAC Traditional name: [(2-chlorophenyl)methyl]({[(1r,4r)-4-({[(2-chlorophenyl)methyl]amino}methyl)cyclohexyl]methyl})amine
• Synonyms: trans-N1,N4-Bis[(2-chlorophenyl)methyl]-1,4-cyclohexanedimethanamine Hydrochloride; N,N'-Bis(o-chlorobenzyl)-trans-1,4-cyclohexanebis(methylamine) Dihydrochloride; AY 9944

Database IDs

• CAS Number: 366-93-8
• PubChem SID: 162255035
• PubChem CID: 9705

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.46837583
• LogD (pH = 7.4): 1.9266984
• Log P: 5.832433
• Molar Refractivity: 112.1056 cm^3
• Polarizability: 44.397713 Å^3
• Polar Surface Area: 24.06 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A794700

Cholesterol synthesis inhibitor; inhibits both 7-dehydrocholesterol Δ7-reductase and Δ8,7-sterol isomerase. A sonic hedgehog inhibitor.

REFERENCES

• Anchour, A., et al.: AIDS, 14, 1454 (2000)
• Incardona, J.P., et al.: Cell. Mol. Life Sci., 57, 1709 (2000)
• Cortez, M., et al.: Neurology, 56, 341 (2000)