N-(4-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)phenyl)-3-(trifluoromethyl)benzamide

ID: ALA566775

PubChem CID: 45483758

Max Phase: Preclinical

Molecular Formula: C20H14F3N5O

Molecular Weight: 397.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ccn2-c1ccc(NC(=O)c2cccc(C(F)(F)F)c2)cc1

Standard InChI:  InChI=1S/C20H14F3N5O/c21-20(22,23)13-3-1-2-12(10-13)19(29)27-14-4-6-15(7-5-14)28-9-8-16-17(24)25-11-26-18(16)28/h1-11H,(H,27,29)(H2,24,25,26)

Standard InChI Key:  IHIKBVHWWIQIQY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    7.6652    1.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6641    0.8102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3789    0.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0953    0.8106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3771    2.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0959    1.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7092    2.1967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3682    2.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5454    2.8608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5341    2.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9356    1.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7598    1.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1823    2.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7746    2.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9518    2.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0072    2.1536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4114    1.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2364    1.4248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9507    2.0499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9910    0.7252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1650    0.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7443    0.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1486   -0.6929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9778   -0.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3947    0.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9194    0.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5155    0.7566    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.4983   -0.6722    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.1425    0.8315    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  3  4  2  0
 14 15  2  0
 15 10  1  0
  4  6  1  0
 13 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 17 18  2  0
  8  9  2  0
  1 19  1  0
  9  5  1  0
  5  1  1  0
 20 21  2  0
  7 10  1  0
 21 22  1  0
  5  6  2  0
 22 23  2  0
 10 11  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 17 20  1  0
 11 12  1  0
 22 26  1  0
  2  3  1  0
 26 27  1  0
 12 13  2  0
 26 28  1  0
  1  2  2  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA566775

   N-[4-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)phenyl]-3-(trifluoromethyl)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: 397.36

Molecular Weight (Monoisotopic): 397.1150

AlogP: 4.27

#Rotatable Bonds: 3

Polar Surface Area: 85.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.92

CX LogP: 4.13

CX LogD: 4.12

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.54

Np Likeness Score: -1.49

References

1. Jung MH, Kim H, Choi WK, El-Gamal MI, Park JH, Yoo KH, Sim TB, Lee SH, Baek D, Hah JM, Cho JH, Oh CH..  (2009)  Synthesis of pyrrolo[2,3-d]pyrimidine derivatives and their antiproliferative activity against melanoma cell line.,  19  (23): [PMID:19857963] [10.1016/j.bmcl.2009.10.051]

Source

Source(1):

• Scientific Literature