4-[5-(4-dimethylamino-piperidin-1-yl)-3H-imidazo[4,5-b]pyridine-2-carbonyl]-2-(1,3,5-trimethyl-1H-pyrazol-4-yl)-benzonitrile

ID: ALA2089057

Cas Number: 1254161-77-7

PubChem CID: 66599617

Max Phase: Preclinical

Molecular Formula: C27H30N8O

Molecular Weight: 482.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nn(C)c(C)c1-c1cc(C(=O)c2nc3nc(N4CCC(N(C)C)CC4)ccc3[nH]2)ccc1C#N

Standard InChI:  InChI=1S/C27H30N8O/c1-16-24(17(2)34(5)32-16)21-14-18(6-7-19(21)15-28)25(36)27-29-22-8-9-23(30-26(22)31-27)35-12-10-20(11-13-35)33(3)4/h6-9,14,20H,10-13H2,1-5H3,(H,29,30,31)

Standard InChI Key:  QRFNPZUNAUBFQC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 36 40  0  0  0  0  0  0  0  0999 V2000
    6.4879   -4.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4915   -3.7597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5328   -3.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945   -3.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1969   -1.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991   -0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5965   -3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8943   -3.7525    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
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7248    1.2135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6065    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7248   -1.2135    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 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1047   -0.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7065    1.0350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8532   -1.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3533   -1.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0987   -2.6109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3442   -3.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0901   -5.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6865   -6.2510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8442   -3.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0987   -2.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0893   -5.1992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7035   -6.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8775   -6.8022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5837   -7.5518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2885   -6.7952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1898   -7.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6078   -5.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8147   -4.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  4  1  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 13  1  0
 17 18  2  0
 18 10  1  0
 15 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  3  0
 24 27  1  0
 27 28  2  0
 28 21  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 32 33  1  0
 33 34  1  0
 33 35  1  0
 35 29  2  0
 35 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2089057

   Benzonitrile, 4-[[5-[4-(diMethylaMino)-1-piperidinyl]-3H-iMidazo[4,5-b]pyridin-2-yl]carbonyl]-2-(1,3,5-triMethyl-1H-pyrazol-4-yl)-

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: 482.59

Molecular Weight (Monoisotopic): 482.2543

AlogP: 3.61

#Rotatable Bonds: 5

Polar Surface Area: 106.73

Molecular Species: BASE

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.75

CX Basic pKa: 9.82

CX LogP: 2.01

CX LogD: 0.83

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.43

Np Likeness Score: -1.53

References

1. Cho YS, Angove H, Brain C, Chen CH, Cheng H, Cheng R, Chopra R, Chung K, Congreve M, Dagostin C, Davis DJ, Feltell R, Giraldes J, Hiscock SD, Kim S, Kovats S, Lagu B, Lewry K, Loo A, Lu Y, Luzzio M, Maniara W, McMenamin R, Mortenson PN, Benning R, O'Reilly M, Rees DC, Shen J, Smith T, Wang Y, Williams G, Woolford AJ, Wrona W, Xu M, Yang F, Howard S..  (2012)  Fragment-Based Discovery of 7-Azabenzimidazoles as Potent, Highly Selective, and Orally Active CDK4/6 Inhibitors.,  3  (6): [PMID:24900493] [10.1021/ml200241a]

2.  (2013)  Imidazole derivatives and their use as modulators of cyclin dependent kinases, 

Source

Source(2):

• Scientific Literature
• BindingDB Database