4-{2-[2-(4-Chloro-phenyl)-ethyl]-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethylsulfanyl}-phenylamine dihydrochloride

ID: ALA3215735

PubChem CID: 90664381

Max Phase: Preclinical

Molecular Formula: C22H27Cl4N3O2S

Molecular Weight: 429.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Cl.Cl.Nc1ccc(SC[C@@H]2CO[C@](CCc3ccc(Cl)cc3)(Cn3ccnc3)O2)cc1

Standard InChI:  InChI=1S/C22H24ClN3O2S.3ClH/c23-18-3-1-17(2-4-18)9-10-22(15-26-12-11-25-16-26)27-13-20(28-22)14-29-21-7-5-19(24)6-8-21;;;/h1-8,11-12,16,20H,9-10,13-15,24H2;3*1H/t20-,22-;;;/m0.../s1

Standard InChI Key:  GTQPFZFAADIHDS-VLYUBEKVSA-N

Molfile:  

     RDKit          2D

 32 32  0  0  0  0  0  0  0  0999 V2000
   13.4441   -1.3139    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.2484   -4.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9441   -5.8435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5965   -5.3123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2447   -3.1359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4984   -5.5497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5677   -6.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1038   -5.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8025   -4.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3385   -4.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.8316   -2.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0312   -5.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7853    2.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5601   -0.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2754    3.5373    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9500   -1.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2933    2.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6648    1.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6807    0.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0522   -0.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4441   -1.3139    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.9441   -1.3139    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  2  6  1  0
  3  7  2  0
  4  7  1  0
  2  8  1  1
  4  8  1  0
  3  9  1  0
  4 10  1  0
  9 10  2  0
  5 11  1  0
  2 13  1  0
  6 14  1  0
 11 14  1  0
 12 15  1  0
 11 16  1  1
 12 16  1  0
 17 20  1  0
 18 21  1  0
 13 22  1  0
 19 22  1  0
 15 23  1  0
 15 24  2  0
 17 25  2  0
 24 25  1  0
 17 26  1  0
 23 26  2  0
 18 27  2  0
 18 28  1  0
 19 29  2  0
 27 29  1  0
 19 30  1  0
 28 30  2  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 429.97

Molecular Weight (Monoisotopic): 429.1278

AlogP: 4.66

#Rotatable Bonds: 8

Polar Surface Area: 62.30

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.43

CX LogP: 4.61

CX LogD: 4.57

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.42

Np Likeness Score: -0.60

References

1. Walker KA, Kertesz DJ, Rotstein DM, Swinney DC, Berry PW, So OY, Webb AS, Watson DM, Mak AY, Burton PM..  (1993)  Selective inhibition of mammalian lanosterol 14 alpha-demethylase: a possible strategy for cholesterol lowering.,  36  (15): [PMID:8340925] [10.1021/jm00067a022]

Source

Source(1):

• Scientific Literature