US9328118, 91

ID: ALA3980817

PubChem CID: 117914116

Max Phase: Preclinical

Molecular Formula: C23H24F3N5O

Molecular Weight: 443.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1CCC(CCOc2ccc(-c3nc(C#N)nc4c3ccn4C)cc2C(F)(F)F)C1

Standard InChI:  InChI=1S/C23H24F3N5O/c1-3-31-10-6-15(14-31)8-11-32-19-5-4-16(12-18(19)23(24,25)26)21-17-7-9-30(2)22(17)29-20(13-27)28-21/h4-5,7,9,12,15H,3,6,8,10-11,14H2,1-2H3

Standard InChI Key:  JEYNWVWDGPTOHT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   11.8916    1.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6001    0.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9962   -1.2080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7486   -2.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7470   -3.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3945   -3.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0946   -3.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7945   -3.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4946   -3.7543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945   -3.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1969   -1.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991   -0.7525    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
    2.5965   -3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8943   -3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8919   -5.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8521   -5.8523    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.9304   -5.8546    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8906   -6.4533    0.0000 F   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
    1.2990    0.7500    0.0000 N   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
   -0.3114   -2.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4133   -1.7530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5871   -1.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.2008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5296   -1.5226    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  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 13 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 24  1  0
 28 29  1  0
 22 30  1  0
 30 31  3  0
  6 32  1  0
 32  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3980817

   4-[4-[2-(1-Ethylpyrrolidin-3-yl)ethoxy]-3-(trifluoromethyl)phenyl]-7-methylpyrrolo[2,3-d]pyrimidine-2-carbonitrile

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: 443.47

Molecular Weight (Monoisotopic): 443.1933

AlogP: 4.64

#Rotatable Bonds: 6

Polar Surface Area: 66.97

Molecular Species: BASE

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.85

CX LogP: 4.84

CX LogD: 2.41

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.56

Np Likeness Score: -1.23

References

1.  (2016)  Nitrogen-containing bicyclic aromatic heterocyclic compound, 

Source

Source(1):

• BindingDB Database