1-(3-Isopropyl-phenyl)-3-[4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-phenyl]-urea

ID: ALA2332867

PubChem CID: 71575544

Max Phase: Preclinical

Molecular Formula: C21H20N6O2

Molecular Weight: 388.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1cccc(NC(=O)Nc2ccc(Oc3ncnc4[nH]ncc34)cc2)c1

Standard InChI:  InChI=1S/C21H20N6O2/c1-13(2)14-4-3-5-16(10-14)26-21(28)25-15-6-8-17(9-7-15)29-20-18-11-24-27-19(18)22-12-23-20/h3-13H,1-2H3,(H2,25,26,28)(H,22,23,24,27)

Standard InChI Key:  FLGQCNMOCNDXHW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   13.4395   -4.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1515   -4.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8640   -4.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8612   -3.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1402   -3.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4307   -3.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1410   -3.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1399   -4.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8547   -4.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5713   -4.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5684   -3.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8529   -3.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2814   -3.1481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9975   -3.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7104   -3.1427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0005   -4.3830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4250   -4.8063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4244   -5.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7094   -6.0418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7084   -6.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4232   -7.2800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9188   -5.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1379   -6.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1427   -6.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9276   -7.1122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4052   -6.4418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1527   -5.6116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4387   -6.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8677   -6.0231    0.0000 C   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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 15  6  1  0
  8 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 24  1  0
 23 18  1  0
 23 24  2  0
 22 23  1  0
 24 25  1  0
 25 26  1  0
 26 22  2  0
  2 27  1  0
 27 28  1  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332867

   1-(3-propan-2-ylphenyl)-3-[4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl]urea

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: 388.43

Molecular Weight (Monoisotopic): 388.1648

AlogP: 4.91

#Rotatable Bonds: 5

Polar Surface Area: 104.82

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.39

CX Basic pKa: 1.37

CX LogP: 4.23

CX LogD: 4.18

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.45

Np Likeness Score: -1.67

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