N-[3-(1H-Pyrazolo[3,4-d]pyrimidin-4-yloxy)-phenyl]-4-trifluoromethyl-benzamide

ID: ALA2332856

PubChem CID: 71575326

Max Phase: Preclinical

Molecular Formula: C19H12F3N5O2

Molecular Weight: 399.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1cccc(Oc2ncnc3[nH]ncc23)c1)c1ccc(C(F)(F)F)cc1

Standard InChI:  InChI=1S/C19H12F3N5O2/c20-19(21,22)12-6-4-11(5-7-12)17(28)26-13-2-1-3-14(8-13)29-18-15-9-25-27-16(15)23-10-24-18/h1-10H,(H,26,28)(H,23,24,25,27)

Standard InChI Key:  RIGIEHDTVCPMDK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    7.2957  -27.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0083  -26.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7213  -27.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7187  -27.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9970  -28.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2869  -27.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8655  -27.0575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5821  -26.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5853  -25.8216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7185  -25.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7173  -26.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4328  -27.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1498  -26.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1469  -25.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4309  -25.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0019  -27.0585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0012  -27.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857  -28.2949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2847  -29.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000  -29.5341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4969  -28.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7152  -28.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7201  -29.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5057  -29.3661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9836  -28.6952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4316  -28.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4274  -29.1346    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.1488  -27.8997    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.1421  -28.7206    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  1  0
  8  9  2  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 11 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 23  1  0
 22 17  1  0
 22 23  2  0
 21 22  1  0
 23 24  1  0
 24 25  1  0
 25 21  2  0
 13  7  1  0
  8  1  1  0
  4 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332856

   N-[3-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl]-4-(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: 399.33

Molecular Weight (Monoisotopic): 399.0943

AlogP: 4.42

#Rotatable Bonds: 4

Polar Surface Area: 92.79

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.39

CX Basic pKa: 1.37

CX LogP: 3.80

CX LogD: 3.76

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -1.99

References

1. Yang LL, Li GB, Ma S, Zou C, Zhou S, Sun QZ, Cheng C, Chen X, Wang LJ, Feng S, Li LL, Yang SY..  (2013)  Structure-activity relationship studies of pyrazolo[3,4-d]pyrimidine derivatives leading to the discovery of a novel multikinase inhibitor that potently inhibits FLT3 and VEGFR2 and evaluation of its activity against acute myeloid leukemia in vitro and in vivo.,  56  (4): [PMID:23362959] [10.1021/jm301537p]

Source

Source(1):

• Scientific Literature