4-(4-methyl-1H-indol-5-ylamino)-5-(5-(piperazin-1-ylmethyl)benzofuran-2-yl)nicotinonitrile

ID: ALA583906

PubChem CID: 44626360

Max Phase: Preclinical

Molecular Formula: C28H26N6O

Molecular Weight: 462.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(Nc2c(C#N)cncc2-c2cc3cc(CN4CCNCC4)ccc3o2)ccc2[nH]ccc12

Standard InChI:  InChI=1S/C28H26N6O/c1-18-22-6-7-32-25(22)4-3-24(18)33-28-21(14-29)15-31-16-23(28)27-13-20-12-19(2-5-26(20)35-27)17-34-10-8-30-9-11-34/h2-7,12-13,15-16,30,32H,8-11,17H2,1H3,(H,31,33)

Standard InChI Key:  DHUPFOOXPODTRC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 40  0  0  0  0  0  0  0  0999 V2000
   10.4352   -7.6119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1666   -8.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7104   -9.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2418   -7.4510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6187   -8.0793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7867   -8.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5203   -8.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1896   -9.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8655   -8.8707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5854   -9.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5922  -10.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3099  -10.5036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0206  -10.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0091   -9.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2908   -8.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7143   -8.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4225   -8.4131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2790   -8.0293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9872   -7.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7037   -8.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4113   -7.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9703   -6.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2483   -6.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8385   -5.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6751   -6.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3984   -6.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0073   -6.2061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6579   -5.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3422   -8.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9027   -7.7286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2887   -6.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8528   -6.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0282   -6.3290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6415   -7.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0793   -7.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  3  0
 14 16  1  0
  7  8  1  0
 15 18  1  0
  8  9  2  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
  4  1  1  0
 20 21  1  0
 21 26  2  0
  6  7  1  0
 25 22  2  0
 22 19  1  0
 10 11  1  0
 22 23  1  0
 25 26  1  0
 11 12  2  0
  2  3  1  0
 12 13  1  0
  3  7  2  0
 24 25  1  0
 26 27  1  0
 27 28  1  0
 28 24  2  0
 13 14  2  0
  2 29  1  0
  1  2  2  0
 29 30  1  0
 30 31  1  0
 14 15  1  0
 15 10  2  0
 10  9  1  0
  6  4  2  0
  5  6  1  0
 30 35  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA583906

   4-(4-methyl-1H-indol-5-ylamino)-5-(5-(piperazin-1-ylmethyl)benzofuran-2-yl)nicotinonitrile

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: 462.56

Molecular Weight (Monoisotopic): 462.2168

AlogP: 5.31

#Rotatable Bonds: 5

Polar Surface Area: 92.91

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.23

CX LogP: 3.80

CX LogD: 1.97

Aromatic Rings: 5

Heavy Atoms: 35

QED Weighted: 0.33

Np Likeness Score: -0.87

References

1. Prashad AS, Wang D, Subrath J, Wu B, Lin M, Zhang MY, Kagan N, Lee J, Yang X, Brennan A, Chaudhary D, Xu X, Leung L, Wang J, Boschelli DH..  (2009)  C-5 substituted heteroaryl-3-pyridinecarbonitriles as PKCtheta inhibitors: part II.,  19  (19): [PMID:19703774] [10.1016/j.bmcl.2009.07.113]

Source

Source(1):

• Scientific Literature