US9409887, I-5

ID: ALA3973190

PubChem CID: 69092880

Max Phase: Preclinical

Molecular Formula: C24H25F3N6O2

Molecular Weight: 486.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)Nc1cccc(Nc2nc(Nc3ccc(NC(C)C)cc3OC)ncc2C(F)(F)F)c1

Standard InChI:  InChI=1S/C24H25F3N6O2/c1-5-21(34)30-15-7-6-8-16(11-15)31-22-18(24(25,26)27)13-28-23(33-22)32-19-10-9-17(29-14(2)3)12-20(19)35-4/h5-14,29H,1H2,2-4H3,(H,30,34)(H2,28,31,32,33)

Standard InChI Key:  VVIRSVARIBXZHS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
    3.6387   -0.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    0.0000 O   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 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
   -0.0031    3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3064    4.9494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3421    3.1476    0.0000 C   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 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
   -0.0031   -3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039   -3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3092   -5.2494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6108   -5.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9072   -5.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9020   -3.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1977   -2.9829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1903   -1.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4841   -0.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4738    0.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1696    1.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8758    0.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5693    1.4977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759    0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2862   -0.4635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0306    1.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0648    0.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8861   -0.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004   -2.9949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2096   -5.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2145   -7.1863    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2465   -5.3824    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2512   -6.5823    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  5 10  2  0
 10 11  1  0
 11 12  2  0
 12  3  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  2  0
 24 30  2  0
 30 20  1  0
 18 31  2  0
 31 14  1  0
 17 32  1  0
 32 33  1  0
 32 34  1  0
 32 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3973190

   N-(3-(2-(4-(isopropylamino)-2-methoxyphenylamino)-5-(trifluoromethyl)pyrimidin-4-ylamino)phenyl)acrylamide

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: 486.50

Molecular Weight (Monoisotopic): 486.1991

AlogP: 5.94

#Rotatable Bonds: 9

Polar Surface Area: 100.20

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.64

CX Basic pKa: 5.74

CX LogP: 5.16

CX LogD: 5.15

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.28

Np Likeness Score: -1.33

References

1.  (2016)  Mutant-selective EGFR inhibitors and uses thereof, 

Source

Source(1):

• BindingDB Database