1-(2,4-Bis-trifluoromethyl-benzyl)-5,6-dichloro-2-piperidin-4-yl-1H-benzoimidazole

ID: ALA351603

PubChem CID: 44375264

Max Phase: Preclinical

Molecular Formula: C21H17Cl2F6N3

Molecular Weight: 496.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  FC(F)(F)c1ccc(Cn2c(C3CCNCC3)nc3cc(Cl)c(Cl)cc32)c(C(F)(F)F)c1

Standard InChI:  InChI=1S/C21H17Cl2F6N3/c22-15-8-17-18(9-16(15)23)32(19(31-17)11-3-5-30-6-4-11)10-12-1-2-13(20(24,25)26)7-14(12)21(27,28)29/h1-2,7-9,11,30H,3-6,10H2

Standard InChI Key:  JKZJGSLVTMJKDI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    5.4292   -1.8625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9167   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292   -0.5292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6500   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6500   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -4.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6875   -2.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -4.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792   -5.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9375   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -3.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9375   -0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -4.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -4.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -1.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3917   -1.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -3.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7750   -3.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0000   -4.4042    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.0042   -5.0292    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.3750   -3.4167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8750   -4.5250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917   -5.6250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -5.6792    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -2.0167    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -0.3625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.0125   -0.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9542   -1.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1875   -0.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1250   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  1  0
  5  4  1  0
  6  8  1  0
  7  1  1  0
  8 11  2  0
  9 14  1  0
 10  4  2  0
 11  7  1  0
 12  5  2  0
 13  8  1  0
 14 20  1  0
 15 10  1  0
 16 15  2  0
 17  2  1  0
 18 30  1  0
 19 11  1  0
 20 19  2  0
 21  6  1  0
 22  6  1  0
 23  6  1  0
 24  9  1  0
 25  9  1  0
 26  9  1  0
 27 15  1  0
 28 16  1  0
 29 31  1  0
 30 32  1  0
 31 17  1  0
 32 17  1  0
  5  3  1  0
 16 12  1  0
 29 18  1  0
 13 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA351603

   1-[[2,4-Bis(trifluoromethyl)phenyl]methyl]-5,6-dichloro-2-piperidin-4-ylbenzimidazole

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: 496.28

Molecular Weight (Monoisotopic): 495.0704

AlogP: 6.90

#Rotatable Bonds: 3

Polar Surface Area: 29.85

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.01

CX LogP: 6.40

CX LogD: 3.88

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.40

Np Likeness Score: -1.23

References

1. He Y, Yang J, Wu B, Robinson D, Sprankle K, Kung PP, Lowery K, Mohan V, Hofstadler S, Swayze EE, Griffey R..  (2004)  Synthesis and evaluation of novel bacterial rRNA-binding benzimidazoles by mass spectrometry.,  14  (3): [PMID:14741271] [10.1016/j.bmcl.2003.11.031]

Source

Source(1):

• Scientific Literature