4-amino-6-(1-(5-chloro-2-methoxy-4-methyl-3-(pyridin-3-yl)phenyl)ethylamino)pyrimidine-5-carbonitrile

ID: ALA4527417

PubChem CID: 155544339

Max Phase: Preclinical

Molecular Formula: C20H19ClN6O

Molecular Weight: 394.87

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1c(C(C)Nc2ncnc(N)c2C#N)cc(Cl)c(C)c1-c1cccnc1

Standard InChI:  InChI=1S/C20H19ClN6O/c1-11-16(21)7-14(18(28-3)17(11)13-5-4-6-24-9-13)12(2)27-20-15(8-22)19(23)25-10-26-20/h4-7,9-10,12H,1-3H3,(H3,23,25,26,27)

Standard InChI Key:  VZMYMYAVCCFWMF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   34.1844   -4.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1833   -5.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8954   -5.9913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6092   -5.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6064   -4.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8937   -4.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4711   -5.9904    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.4725   -4.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3217   -5.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3230   -6.8106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.0329   -5.5796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0355   -7.2223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4518   -8.0386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.4479   -7.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7398   -6.8052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.7438   -8.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0341   -8.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8884   -3.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6006   -3.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5986   -2.2965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8850   -1.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1720   -2.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1776   -3.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3167   -4.3397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.3136   -3.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7453   -9.2696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3273   -8.4544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6157   -8.8674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  1  8  1  0
  4  9  1  0
  9 10  1  0
  9 11  1  0
 10 12  1  0
 12 17  2  0
 16 13  2  0
 13 14  1  0
 14 15  2  0
 15 12  1  0
 16 17  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
  6 18  1  0
  5 24  1  0
 24 25  1  0
 16 26  1  0
 27 28  3  0
 17 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4527417

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 394.87

Molecular Weight (Monoisotopic): 394.1309

AlogP: 4.14

#Rotatable Bonds: 5

Polar Surface Area: 109.74

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.64

CX LogP: 3.27

CX LogD: 3.27

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.67

Np Likeness Score: -0.99

References

1. Perry MWD, Abdulai R, Mogemark M, Petersen J, Thomas MJ, Valastro B, Westin Eriksson A..  (2019)  Evolution of PI3Kγ and δ Inhibitors for Inflammatory and Autoimmune Diseases.,  62  (10): [PMID:30582813] [10.1021/acs.jmedchem.8b01298]

Source

Source(1):

• Scientific Literature