US9409887, I-4

ID: ALA3962343

PubChem CID: 117828117

Max Phase: Preclinical

Molecular Formula: C23H25ClN6O2

Molecular Weight: 452.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)Nc1cccc(Nc2nc(Nc3ccc(NC(C)C)cc3OC)ncc2Cl)c1

Standard InChI:  InChI=1S/C23H25ClN6O2/c1-5-21(31)27-15-7-6-8-16(11-15)28-22-18(24)13-25-23(30-22)29-19-10-9-17(26-14(2)3)12-20(19)32-4/h5-14,26H,1H2,2-4H3,(H,27,31)(H2,25,28,29,30)

Standard InChI Key:  IEZFFFOOLULQBR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  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
   -4.9485   -5.8368    0.0000 Cl  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
  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
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  2  0
 25 31  2  0
 31 21  1  0
 19 32  2  0
 32 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3962343

   N-[3-[[5-chloro-2-[2-methoxy-4-(propan-2-ylamino)anilino]pyrimidin-4-yl]amino]phenyl]prop-2-enamide

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: 452.95

Molecular Weight (Monoisotopic): 452.1728

AlogP: 5.57

#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: 13.94

CX Basic pKa: 5.74

CX LogP: 4.89

CX LogD: 4.88

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.31

Np Likeness Score: -1.41

References

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

Source

Source(1):

• BindingDB Database