2-(2-methoxyphenyl)-4-(4-methyl-1H-indol-5-ylamino)thieno[2,3-b]pyridine-5-carbonitrile

ID: ALA480839

PubChem CID: 44570803

Max Phase: Preclinical

Molecular Formula: C24H18N4OS

Molecular Weight: 410.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1-c1cc2c(Nc3ccc4[nH]ccc4c3C)c(C#N)cnc2s1

Standard InChI:  InChI=1S/C24H18N4OS/c1-14-16-9-10-26-20(16)8-7-19(14)28-23-15(12-25)13-27-24-18(23)11-22(30-24)17-5-3-4-6-21(17)29-2/h3-11,13,26H,1-2H3,(H,27,28)

Standard InChI Key:  ZYTAPJWMMBTUHH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -0.3512  -14.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3524  -15.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3620  -15.9225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0781  -15.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3602  -14.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0763  -14.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6916  -14.1317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558  -13.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5330  -13.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0654  -14.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0668  -15.9215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0674  -16.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687  -18.3936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3519  -17.9775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3584  -16.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0702  -16.3237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5684  -16.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0562  -17.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5707  -18.2344    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8783  -17.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2887  -16.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1125  -16.8450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5268  -17.5589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1113  -18.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2889  -18.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8745  -16.1338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0500  -16.1361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  3  4  2  0
 14 15  2  0
 15 12  1  0
  4  6  1  0
 15 16  1  0
  6  7  1  0
 16 17  3  0
 18 19  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  5  1  1  0
  1 10  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  1  0
  5  6  2  0
  2 11  1  0
 23 24  2  0
 24 25  1  0
 11 12  1  0
 25 26  2  0
 12 19  2  0
 26 27  1  0
  2  3  1  0
 27 28  2  0
 28 23  1  0
 21 23  1  0
 18 13  2  0
 24 29  1  0
  1  2  2  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA480839

   2-(2-methoxyphenyl)-4-(4-methyl-1H-indol-5-ylamino)thieno[2,3-b]pyridine-5-carbonitrile

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: 410.50

Molecular Weight (Monoisotopic): 410.1201

AlogP: 6.38

#Rotatable Bonds: 4

Polar Surface Area: 73.73

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 1.49

CX LogP: 5.39

CX LogD: 5.39

Aromatic Rings: 5

Heavy Atoms: 30

QED Weighted: 0.36

Np Likeness Score: -1.21

References

1. Wu B, Boschelli DH, Lee J, Yang X, Chaudhary D..  (2009)  Second generation 4-(4-methyl-1H-indol-5-ylamino)-2-phenylthieno[2,3-b]pyridine-5-carbonitrile PKCtheta inhibitors.,  19  (3): [PMID:19111463] [10.1016/j.bmcl.2008.12.021]

Source

Source(1):

• Scientific Literature