N-(3-(2-(3-Amino-6-(1-(1-isopropylpiperidin-4-yl)-1H-pyrazol-4-yl)pyrazin-2-yl)-1H-benzo[d]imidazol-1-yl)phenyl)acrylamide

ID: ALA3814884

PubChem CID: 127052414

Max Phase: Preclinical

Molecular Formula: C31H33N9O

Molecular Weight: 547.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)Nc1cccc(-n2c(-c3nc(-c4cnn(C5CCN(C(C)C)CC5)c4)cnc3N)nc3ccccc32)c1

Standard InChI:  InChI=1S/C31H33N9O/c1-4-28(41)35-22-8-7-9-24(16-22)40-27-11-6-5-10-25(27)37-31(40)29-30(32)33-18-26(36-29)21-17-34-39(19-21)23-12-14-38(15-13-23)20(2)3/h4-11,16-20,23H,1,12-15H2,2-3H3,(H2,32,33)(H,35,41)

Standard InChI Key:  VAQTZTINFQWWJP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.5265    8.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9759   10.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6383    7.9411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8879    6.3826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8114    5.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2517    3.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749    2.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6621    2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2218    4.2301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2965    5.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0791   -0.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2418   -1.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2286   -5.1568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5770   -4.4998    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3688   -3.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1870   -4.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9674   -6.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3957    2.3477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0374   -7.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6659   -9.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2216   -9.5371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1488   -8.4888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5202   -7.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8470  -10.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6911  -11.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7038  -11.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  1  4  2  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  6 11  2  0
 12 13  1  0
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 18 19  2  0
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 13 19  1  0
 14 20  1  0
 21 22  1  0
 21 23  2  0
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 24 25  1  0
 25 26  2  0
 23 26  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 27 31  1  0
 27 32  1  0
 26 30  1  0
 22 33  1  0
 18 21  1  0
  8 20  1  0
  5  6  1  0
 32 34  1  0
 32 38  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 36 39  1  0
 39 40  1  0
 39 41  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3814884

   ---

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: 547.67

Molecular Weight (Monoisotopic): 547.2808

AlogP: 5.10

#Rotatable Bonds: 7

Polar Surface Area: 119.78

Molecular Species: BASE

HBA: 9

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 9.56

CX LogP: 4.14

CX LogD: 2.00

Aromatic Rings: 5

Heavy Atoms: 41

QED Weighted: 0.27

Np Likeness Score: -1.33

References

1. Hennessy EJ, Chuaqui C, Ashton S, Colclough N, Cross DA, Debreczeni JÉ, Eberlein C, Gingipalli L, Klinowska TC, Orme JP, Sha L, Wu X..  (2016)  Utilization of Structure-Based Design to Identify Novel, Irreversible Inhibitors of EGFR Harboring the T790M Mutation.,  7  (5): [PMID:27190603] [10.1021/acsmedchemlett.6b00058]

Source

Source(1):

• Scientific Literature