4-(1-(3-(1H-benzo[d]imidazol-2-yl)-4-methylbenzoyl)piperidin-4-yl)benzonitrile

ID: ALA2322659

PubChem CID: 68288836

Max Phase: Preclinical

Molecular Formula: C27H24N4O

Molecular Weight: 420.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C(=O)N2CCC(c3ccc(C#N)cc3)CC2)cc1-c1nc2ccccc2[nH]1

Standard InChI:  InChI=1S/C27H24N4O/c1-18-6-9-22(16-23(18)26-29-24-4-2-3-5-25(24)30-26)27(32)31-14-12-21(13-15-31)20-10-7-19(17-28)8-11-20/h2-11,16,21H,12-15H2,1H3,(H,29,30)

Standard InChI Key:  JPDWPGOJRJFVMZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    4.7207   -3.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0445   -4.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6946   -5.8864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8490   -7.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3532   -7.0124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7031   -5.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5536   -4.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    0.0000 N   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
    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
   -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
    0.3114   -2.9665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5046   -8.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0228   -9.3326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0082   -8.1352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8418   -9.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3372   -9.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9826   -7.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1327   -6.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6374   -6.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4787   -7.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3307   -9.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8258   -8.8952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4691   -7.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6173   -6.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1221   -6.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9651   -7.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1612   -7.3234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 15 16  1  0
 16  8  1  0
  5 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 19  1  0
 22 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 28 31  1  0
 31 32  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA2322659

   4-[1-[3-(1H-benzimidazol-2-yl)-4-methylbenzoyl]piperidin-4-yl]benzonitrile

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: 420.52

Molecular Weight (Monoisotopic): 420.1950

AlogP: 5.43

#Rotatable Bonds: 3

Polar Surface Area: 72.78

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.47

CX Basic pKa: 5.12

CX LogP: 5.22

CX LogD: 5.22

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.48

Np Likeness Score: -1.41

References

1. Oslob JD, Johnson RJ, Cai H, Feng SQ, Hu L, Kosaka Y, Lai J, Sivaraja M, Tep S, Yang H, Zaharia CA, Evanchik MJ, McDowell RS..  (2013)  Imidazopyridine-Based Fatty Acid Synthase Inhibitors That Show Anti-HCV Activity and in Vivo Target Modulation.,  4  (1): [PMID:24900571] [10.1021/ml300335r]

2.  (2014)  Heterocyclic modulators of lipid synthesis, 

Source

Source(2):

• Scientific Literature
• BindingDB Database