4-(1-(2,4-dimethyl-5-(6-(piperazin-1-yl)-3H-imidazo[4,5-c]pyridin-2-yl)benzoyl)piperidin-4-yl)benzonitrile

ID: ALA2322369

PubChem CID: 68289227

Max Phase: Preclinical

Molecular Formula: C31H33N7O

Molecular Weight: 519.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C)c(-c2nc3cc(N4CCNCC4)ncc3[nH]2)cc1C(=O)N1CCC(c2ccc(C#N)cc2)CC1

Standard InChI:  InChI=1S/C31H33N7O/c1-20-15-21(2)26(31(39)38-11-7-24(8-12-38)23-5-3-22(18-32)4-6-23)16-25(20)30-35-27-17-29(34-19-28(27)36-30)37-13-9-33-10-14-37/h3-6,15-17,19,24,33H,7-14H2,1-2H3,(H,35,36)

Standard InChI Key:  XXSXHAXCDDVVBR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 39 44  0  0  0  0  0  0  0  0999 V2000
    4.3691   -8.2067    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
    4.6946   -5.8864    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
    4.7207   -3.5432    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
    1.7031   -5.6606    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
    1.5046   -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
    1.8032   -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 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
    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
    0.0000    3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2978    3.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2954    5.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0048    6.0009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3026    5.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3002    3.7488    0.0000 C   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  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  2  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 11  1  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
 23 24  3  0
  6 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 32 33  1  0
 33 25  1  0
 29 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2322369

   4-[1-[2,4-dimethyl-5-(6-piperazin-1-yl-3H-imidazo[4,5-c]pyridin-2-yl)benzoyl]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: 519.65

Molecular Weight (Monoisotopic): 519.2747

AlogP: 4.54

#Rotatable Bonds: 4

Polar Surface Area: 100.94

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.64

CX Basic pKa: 8.81

CX LogP: 4.69

CX LogD: 3.26

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.41

Np Likeness Score: -1.45

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