US9321760, 63

ID: ALA3984858

PubChem CID: 89444857

Max Phase: Preclinical

Molecular Formula: C25H28ClFN6O

Molecular Weight: 482.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(c1ccc(Cl)cc1OC1CNC1)N1CCN(c2ncnc(N)c2-c2ccc(F)cc2)CC1

Standard InChI:  InChI=1S/C25H28ClFN6O/c1-16(21-7-4-18(26)12-22(21)34-20-13-29-14-20)32-8-10-33(11-9-32)25-23(24(28)30-15-31-25)17-2-5-19(27)6-3-17/h2-7,12,15-16,20,29H,8-11,13-14H2,1H3,(H2,28,30,31)

Standard InChI Key:  ZEDLSCZYQROHLE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
    3.6375   -0.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    0.7484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993    2.9963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9014    3.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9034    4.9484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3027    3.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012    3.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2954    3.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2906    5.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3280    5.8645    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0108    6.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3074    5.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935   -3.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2883   -5.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5847   -6.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806   -7.2040    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8864   -5.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8915   -3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1954   -3.0153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4915   -3.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8985   -3.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2766   -4.8194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8250   -5.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  3  1  0
  6  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15  9  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 16  1  0
  2 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 29 23  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3984858

   6-[4-[1-[2-(Azetidin-3-yloxy)-4-chlorophenyl]ethyl]piperazin-1-yl]-5-(4-fluorophenyl)pyrimidin-4-amine

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: 482.99

Molecular Weight (Monoisotopic): 482.1997

AlogP: 3.75

#Rotatable Bonds: 6

Polar Surface Area: 79.54

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.56

CX LogP: 4.27

CX LogD: 2.86

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.55

Np Likeness Score: -0.94

References

1.  (2016)  Aminopyrimidine derivatives for use as modulators of kinase activity, 

Source

Source(1):

• BindingDB Database