(R)-3-(4-(7-cyano-3-(hydroxymethyl)-3-methylindolin-5-yl)pyrimidin-2-ylamino)-N,4-dimethylbenzamide

ID: ALA4218285

PubChem CID: 130270547

Max Phase: Preclinical

Molecular Formula: C24H24N6O2

Molecular Weight: 428.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)c1ccc(C)c(Nc2nccc(-c3cc(C#N)c4c(c3)[C@@](C)(CO)CN4)n2)c1

Standard InChI:  InChI=1S/C24H24N6O2/c1-14-4-5-15(22(32)26-3)10-20(14)30-23-27-7-6-19(29-23)16-8-17(11-25)21-18(9-16)24(2,13-31)12-28-21/h4-10,28,31H,12-13H2,1-3H3,(H,26,32)(H,27,29,30)/t24-/m1/s1

Standard InChI Key:  AZLAULHUEAUCSF-XMMPIXPASA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    5.1962   -3.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904   -3.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2007   -4.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1736   -5.7148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8832   -5.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1752   -6.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4658   -6.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4653   -7.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1734   -8.1636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8836   -7.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8806   -6.9357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1718   -4.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8838   -4.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1536   -3.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7589   -4.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0483   -3.6691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1916   -2.6992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5926   -8.1571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2990   -7.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0048   -8.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7106   -7.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7084   -6.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9944   -6.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2914   -6.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0061   -8.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9888   -5.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6937   -5.2883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2783   -5.2980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4042   -5.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7 15  1  0
 14  4  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  6  8  1  0
 14 15  2  0
 15  2  1  0
  2 16  1  0
 16 17  1  0
 17 14  1  0
  4 18  1  0
 18 19  3  0
  1 20  1  0
 12 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 23 28  1  0
 26 29  1  0
 29 30  1  0
 29 31  2  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4218285

   ---

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: 428.50

Molecular Weight (Monoisotopic): 428.1961

AlogP: 3.10

#Rotatable Bonds: 5

Polar Surface Area: 122.96

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.46

CX Basic pKa: 2.35

CX LogP: 2.62

CX LogD: 2.62

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.49

Np Likeness Score: -0.81

References

1. Kargbo RB..  (2017)  New Substituted Cyanoindoline Derivatives as MAP3K14 Kinase Inhibitors for the Treatment of Cancer and Autoimmune Disorders.,  8  (9): [PMID:28947934] [10.1021/acsmedchemlett.7b00330]

Source

Source(1):

• Scientific Literature