2-Chloro-N-(4-(5-fluoro-2-(4-hydroxyphenylamino)pyrimidin-4-ylamino)phenyl)benzamide

ID: ALA523991

PubChem CID: 42628076

Max Phase: Preclinical

Molecular Formula: C23H17ClFN5O2

Molecular Weight: 449.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(Nc2nc(Nc3ccc(O)cc3)ncc2F)cc1)c1ccccc1Cl

Standard InChI:  InChI=1S/C23H17ClFN5O2/c24-19-4-2-1-3-18(19)22(32)28-15-7-5-14(6-8-15)27-21-20(25)13-26-23(30-21)29-16-9-11-17(31)12-10-16/h1-13,31H,(H,28,32)(H2,26,27,29,30)

Standard InChI Key:  ZYURNHOEBWWJHI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    0.7949    0.0173    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.7949   -0.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5094   -1.2202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5094   -2.0452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7949   -2.4577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7949   -3.2827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5094   -3.6952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5094   -4.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2239   -4.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9383   -4.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6528   -4.9327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9383   -3.6952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2239   -3.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0805   -2.0452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0805   -1.2202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6340   -0.8077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6340    0.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0805    0.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3485    0.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3485    1.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6340    1.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0805    1.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6340    2.4923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3485    2.9048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630    2.4923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3485    3.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630    4.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7774    3.7298    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630    4.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6340    4.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6340    4.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3485    5.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  2  0
  2 15  1  0
  3  4  1  0
  5  4  2  0
  5  6  1  0
  5 14  1  0
  7  6  1  0
  8  7  2  0
 13  7  1  0
  9  8  1  0
 10  9  2  0
 10 11  1  0
 12 10  1  0
 13 12  2  0
 15 14  2  0
 15 16  1  0
 17 16  1  0
 18 17  2  0
 17 19  1  0
 18 22  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 24 23  1  0
 24 25  2  0
 26 24  1  0
 26 27  2  0
 30 26  1  0
 27 28  1  0
 27 29  1  0
 32 29  2  0
 31 30  2  0
 32 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA523991

   2-Chloro-N-[4-({5-Fluoro-2-[(4-Hydroxyphenyl)amino]pyrimidin-4-Yl}amino)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: 449.87

Molecular Weight (Monoisotopic): 449.1055

AlogP: 5.71

#Rotatable Bonds: 6

Polar Surface Area: 99.17

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.23

CX Basic pKa: 2.20

CX LogP: 5.74

CX LogD: 5.74

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.28

Np Likeness Score: -1.38

References

1. Aliagas-Martin I, Burdick D, Corson L, Dotson J, Drummond J, Fields C, Huang OW, Hunsaker T, Kleinheinz T, Krueger E, Liang J, Moffat J, Phillips G, Pulk R, Rawson TE, Ultsch M, Walker L, Wiesmann C, Zhang B, Zhu BY, Cochran AG..  (2009)  A class of 2,4-bisanilinopyrimidine Aurora A inhibitors with unusually high selectivity against Aurora B.,  52  (10): [PMID:19402633] [10.1021/jm9000314]

Source

Source(1):

• Scientific Literature