(3R)-5-[2-[5-[dideuterio(hydroxy)methyl]-2-methyl-anilino]pyrimidin-4-yl]-3-(hydroxymethyl)-3-methyl-indoline-7-carbonitrile

ID: ALA4206684

PubChem CID: 145976657

Max Phase: Preclinical

Molecular Formula: C23H23N5O2

Molecular Weight: 401.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [2H]C([2H])(O)c1ccc(C)c(Nc2nccc(-c3cc(C#N)c4c(c3)[C@@](C)(CO)CN4)n2)c1

Standard InChI:  InChI=1S/C23H23N5O2/c1-14-3-4-15(11-29)7-20(14)28-22-25-6-5-19(27-22)16-8-17(10-24)21-18(9-16)23(2,13-30)12-26-21/h3-9,26,29-30H,11-13H2,1-2H3,(H,25,27,28)/t23-/m1/s1/i11D2

Standard InChI Key:  DJHBXXYGFAJRGL-CVWTWWASSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   20.8879  -14.7094    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.7051  -14.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3001  -14.0038    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.9127  -12.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2069  -12.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9172  -13.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1832  -13.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1820  -14.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8901  -14.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5997  -14.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8917  -15.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1823  -15.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.8899  -17.1775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   18.8883  -13.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.0550  -12.2885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4753  -13.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7648  -12.6830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9081  -11.7131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3091  -17.1709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0155  -16.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7212  -17.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4271  -16.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4249  -15.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7109  -15.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0079  -15.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7226  -17.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4102  -14.3022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  5  6  1  1
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 18  1  0
 17  7  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  9 11  1  0
 17 18  2  0
 18  5  1  0
  5 19  1  0
 19 20  1  0
 20 17  1  0
  7 21  1  0
 21 22  3  0
  4 23  1  0
 15 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 29  2  1  0
 26 31  1  0
  2 32  1  0
M  ISO  2   1   2   3   2
M  END

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: 401.47

Molecular Weight (Monoisotopic): 401.1852

AlogP: 3.24

#Rotatable Bonds: 5

Polar Surface Area: 114.09

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.93

CX Basic pKa: 2.42

CX LogP: 2.78

CX LogD: 2.78

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.52

Np Likeness Score: -0.35

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