5,6-Dichloro-1-pentafluorophenylmethyl-2-piperidin-4-yl-1H-benzoimidazole

ID: ALA163487

PubChem CID: 44375263

Max Phase: Preclinical

Molecular Formula: C19H14Cl2F5N3

Molecular Weight: 450.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Fc1c(F)c(F)c(Cn2c(C3CCNCC3)nc3cc(Cl)c(Cl)cc32)c(F)c1F

Standard InChI:  InChI=1S/C19H14Cl2F5N3/c20-10-5-12-13(6-11(10)21)29(19(28-12)8-1-3-27-4-2-8)7-9-14(22)16(24)18(26)17(25)15(9)23/h5-6,8,27H,1-4,7H2

Standard InChI Key:  YJWBHCCDYIDBAY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    5.4375   -2.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -3.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9250   -1.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292   -0.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6500   -1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6500   -1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -5.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9750   -5.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4125   -5.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792   -4.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4042   -4.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000   -3.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -1.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3917   -1.5542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -6.3167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.1250   -5.4917    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2625   -5.4917    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.1167   -3.8375    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2625   -3.8417    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -2.4042    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -0.7542    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.9792   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9750   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1625   -2.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1500   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  0
  3  1  1  0
  4  3  2  0
  5  1  1  0
  6  5  1  0
  7  9  2  0
  8 10  2  0
  9 11  1  0
 10  2  1  0
 11  2  2  0
 12  1  1  0
 13  5  2  0
 14  6  2  0
 15 13  1  0
 16 15  2  0
 17  3  1  0
 18 27  1  0
 19  7  1  0
 20  9  1  0
 21  8  1  0
 22 11  1  0
 23 10  1  0
 24 15  1  0
 25 16  1  0
 26 28  1  0
 27 29  1  0
 28 17  1  0
 29 17  1  0
  6  4  1  0
  7  8  1  0
 16 14  1  0
 18 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA163487

   5,6-Dichloro-1-[(2,3,4,5,6-pentafluorophenyl)methyl]-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: 450.24

Molecular Weight (Monoisotopic): 449.0485

AlogP: 5.55

#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: 5.36

CX LogD: 2.84

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.32

Np Likeness Score: -0.97

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