N-isobutyl-4-(2-(4-methoxyphenyl)-3H-imidazo[4,5-b]pyridin-6-yl)thiophene-2-carboxamide

ID: ALA3125727

PubChem CID: 76321826

Max Phase: Preclinical

Molecular Formula: C22H22N4O2S

Molecular Weight: 406.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2nc3cc(-c4csc(C(=O)NCC(C)C)c4)cnc3[nH]2)cc1

Standard InChI:  InChI=1S/C22H22N4O2S/c1-13(2)10-24-22(27)19-9-16(12-29-19)15-8-18-21(23-11-15)26-20(25-18)14-4-6-17(28-3)7-5-14/h4-9,11-13H,10H2,1-3H3,(H,24,27)(H,23,25,26)

Standard InChI Key:  KMIUIHAGKAMAMN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   14.0122  -12.0129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3026  -11.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3054  -10.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0140  -10.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7203  -11.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7190  -10.7829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4995  -10.5279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9832  -11.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5015  -11.8564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8004  -11.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2052  -11.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0217  -11.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4301  -11.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0160  -10.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2010  -10.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2472  -11.1879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6578  -11.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6027  -10.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5216   -9.5544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7220   -9.3811    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.3113  -10.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8584  -10.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5021  -10.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0193   -9.5177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1725  -10.9248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3601  -11.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0305  -11.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2182  -11.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5134  -12.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  8 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
 13 16  1  0
 16 17  1  0
 19 20  1  0
 18 19  2  0
 20 21  1  0
 21 22  2  0
 22 18  1  0
  3 18  1  0
 21 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3125727

   4-[2-(4-methoxyphenyl)-1H-imidazo[4,5-b]pyridin-6-yl]-N-(2-methylpropyl)thiophene-2-carboxamide

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: 406.51

Molecular Weight (Monoisotopic): 406.1463

AlogP: 4.75

#Rotatable Bonds: 6

Polar Surface Area: 79.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.22

CX Basic pKa: 2.11

CX LogP: 4.16

CX LogD: 4.16

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.48

Np Likeness Score: -1.26

References

1. Johannes JW, Chuaqui C, Cowen S, Devereaux E, Gingipalli L, Molina A, Wang T, Whitston D, Wu X, Zhang HJ, Zinda M..  (2014)  Discovery of 6-aryl-azabenzimidazoles that inhibit the TBK1/IKK-ε kinases.,  24  (4): [PMID:24462666] [10.1016/j.bmcl.2013.12.123]

Source

Source(1):

• Scientific Literature