4-Amino-N-[3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide

ID: ALA113302

PubChem CID: 44340691

Max Phase: Preclinical

Molecular Formula: C22H18N6O

Molecular Weight: 382.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(C(=O)Nc2cccc(Nc3nccc(-c4cccnc4)n3)c2)cc1

Standard InChI:  InChI=1S/C22H18N6O/c23-17-8-6-15(7-9-17)21(29)26-18-4-1-5-19(13-18)27-22-25-12-10-20(28-22)16-3-2-11-24-14-16/h1-14H,23H2,(H,26,29)(H,25,27,28)

Standard InChI Key:  OEPYYTCOZCQKGP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    3.8667    0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -0.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4542    1.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4625    0.5500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875    0.5333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500    0.5250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417    1.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1667    1.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0167    0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3042    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625   -3.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417    2.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0250    1.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375    0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3042    2.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875    3.0458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292    3.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3042    1.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625   -2.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0250   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4292   -2.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500   -3.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7500   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3125   -0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4292   -3.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4 10  1  0
  5  2  2  0
  6  1  1  0
  7  1  2  0
  8  3  1  0
  9  5  1  0
 10 12  2  0
 11  3  2  0
 12 13  1  0
 13  6  1  0
 14 23  2  0
 15  8  2  0
 16  8  1  0
 17 18  2  0
 18  7  1  0
 19 22  1  0
 20 19  1  0
 21 15  1  0
 22 16  2  0
 23  9  1  0
 24 28  1  0
 25  9  2  0
 26 29  2  0
 27 24  2  0
 28 13  2  0
 29 25  1  0
 17  5  1  0
 10 27  1  0
 26 14  1  0
 21 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA113302

   4-Amino-N-[3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide

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: 382.43

Molecular Weight (Monoisotopic): 382.1542

AlogP: 4.12

#Rotatable Bonds: 5

Polar Surface Area: 105.82

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.95

CX Basic pKa: 4.28

CX LogP: 3.25

CX LogD: 3.25

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.45

Np Likeness Score: -1.56

References

1. Rachid Z, Katsoulas A, Brahimi F, Jean-Claude BJ..  (2003)  Synthesis of pyrimidinopyridine-triazene conjugates targeted to abl tyrosine kinase.,  13  (19): [PMID:12951113] [10.1016/s0960-894x(03)00553-5]

2. Cui J, Fu R, Zhou LH, Chen SP, Li GW, Qian SX, Liu S..  (2013)  BCR-ABL tyrosine kinase inhibitor pharmacophore model derived from a series of phenylaminopyrimidine-based (PAP) derivatives.,  23  (8): [PMID:23473682] [10.1016/j.bmcl.2013.01.113]

Source

Source(1):

• Scientific Literature