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

ID: ALA507170

PubChem CID: 44139712

Max Phase: Preclinical

Molecular Formula: C20H18FN5O2

Molecular Weight: 379.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC1CC1)c1ccc(Nc2nc(Nc3ccc(O)cc3)ncc2F)cc1

Standard InChI:  InChI=1S/C20H18FN5O2/c21-17-11-22-20(25-15-7-9-16(27)10-8-15)26-18(17)23-13-3-1-12(2-4-13)19(28)24-14-5-6-14/h1-4,7-11,14,27H,5-6H2,(H,24,28)(H2,22,23,25,26)

Standard InChI Key:  MOVLGZOUINJGGA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   14.4442  -11.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7312  -12.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0145  -11.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3036  -12.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3075  -12.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0243  -13.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7335  -12.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4382  -10.8531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1609  -12.0843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5946  -13.3429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3212  -15.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3152  -14.5777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5985  -14.1692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8877  -14.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8916  -15.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6083  -15.8181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0380  -15.8089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0419  -16.6351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3290  -17.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3350  -17.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0517  -18.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7589  -17.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7550  -17.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0556  -19.1103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1708  -14.1747    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.8732  -11.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6969  -11.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2803  -10.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  2  7  2  0
  1  8  2  0
  1  9  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 18 23  2  0
 21 24  1  0
 17 18  1  0
 11 17  1  0
 14 25  1  0
 10 13  1  0
  5 10  1  0
  9 26  1  0
 27 26  1  0
 28 27  1  0
 26 28  1  0
  1  2  1  0
  2  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA507170

   2,4-Bisanilinopyrimidine, 14

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: 379.40

Molecular Weight (Monoisotopic): 379.1445

AlogP: 3.70

#Rotatable Bonds: 6

Polar Surface Area: 99.17

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.23

CX Basic pKa: 2.19

CX LogP: 3.58

CX LogD: 3.58

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.49

Np Likeness Score: -1.14

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