(R)-5-(2-(5-cyano-2-methylphenylamino)-5-fluoropyrimidin-4-yl)-3-(hydroxymethyl)-3-methylindoline-7-carbonitrile

ID: ALA4211563

PubChem CID: 130271145

Max Phase: Preclinical

Molecular Formula: C23H19FN6O

Molecular Weight: 414.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C#N)cc1Nc1ncc(F)c(-c2cc(C#N)c3c(c2)[C@@](C)(CO)CN3)n1

Standard InChI:  InChI=1S/C23H19FN6O/c1-13-3-4-14(8-25)5-19(13)29-22-27-10-18(24)21(30-22)15-6-16(9-26)20-17(7-15)23(2,12-31)11-28-20/h3-7,10,28,31H,11-12H2,1-2H3,(H,27,29,30)/t23-/m1/s1

Standard InChI Key:  MTAANRZOZOKCIN-HSZRJFAPSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   14.0738  -12.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3681  -12.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0784  -13.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3443  -13.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3432  -14.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0512  -14.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7609  -14.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0529  -15.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3435  -15.8937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3429  -16.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0511  -17.1197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7612  -16.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7583  -15.8918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0494  -13.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7615  -13.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0312  -12.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2162  -12.2307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6365  -13.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9260  -12.6252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0693  -11.6553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4703  -17.1132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1766  -16.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8824  -17.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5883  -16.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5861  -15.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8720  -15.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1691  -15.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8665  -14.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8610  -13.8383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6363  -15.4842    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.8838  -17.9266    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
 26 28  1  0
 28 29  3  0
  9 30  1  0
 23 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4211563

   ---

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: 414.44

Molecular Weight (Monoisotopic): 414.1604

AlogP: 3.75

#Rotatable Bonds: 4

Polar Surface Area: 117.65

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.34

CX Basic pKa: 1.64

CX LogP: 3.54

CX LogD: 3.54

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.59

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