4-(1-(5-(6-((2-methoxyethyl)(methyl)amino)-3H-imidazo[4,5-c]pyridin-2-yl)-2,4-dimethylbenzoyl)piperidin-4-yl)benzonitrile

ID: ALA2322359

PubChem CID: 68289174

Max Phase: Preclinical

Molecular Formula: C31H34N6O2

Molecular Weight: 522.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCN(C)c1cc2nc(-c3cc(C(=O)N4CCC(c5ccc(C#N)cc5)CC4)c(C)cc3C)[nH]c2cn1

Standard InChI:  InChI=1S/C31H34N6O2/c1-20-15-21(2)26(31(38)37-11-9-24(10-12-37)23-7-5-22(18-32)6-8-23)16-25(20)30-34-27-17-29(33-19-28(27)35-30)36(3)13-14-39-4/h5-8,15-17,19,24H,9-14H2,1-4H3,(H,34,35)

Standard InChI Key:  GGKBAEBXMLYHNN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 39 43  0  0  0  0  0  0  0  0999 V2000
    4.9292   -5.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 O   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
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.9049    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
   -0.3115    2.9665    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 N   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
   -4.0507    4.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8964    5.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3927    5.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0709    6.4181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0413    4.0747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5366    3.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1821    2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3322    1.3665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8368    1.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1914    2.8386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9779    0.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4732   -0.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1165   -1.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2646   -2.6984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7694   -2.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1261   -1.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9082   -4.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4229   -5.1382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2462    6.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9227    7.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7505    7.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049    5.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7082    5.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13  9  2  0
 13 14  1  0
 14 15  2  0
 15  7  1  0
 11 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 21  1  0
 24 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
 30 33  1  0
 33 34  3  0
 18 35  2  0
 35 36  1  0
 35 37  1  0
 37 38  2  0
 38 16  1  0
 38 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2322359

   4-[1-[5-[6-[2-methoxyethyl(methyl)amino]-3H-imidazo[4,5-c]pyridin-2-yl]-2,4-dimethylbenzoyl]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: 522.65

Molecular Weight (Monoisotopic): 522.2743

AlogP: 5.22

#Rotatable Bonds: 7

Polar Surface Area: 98.14

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.65

CX Basic pKa: 6.10

CX LogP: 5.17

CX LogD: 5.15

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.36

Np Likeness Score: -1.46

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