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

ID: ALA2332850

PubChem CID: 71575214

Max Phase: Preclinical

Molecular Formula: C20H18N6O3

Molecular Weight: 390.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(NC(=O)Nc2ccc(Oc3ncnc4c3cnn4C)cc2)c1

Standard InChI:  InChI=1S/C20H18N6O3/c1-26-18-17(11-23-26)19(22-12-21-18)29-15-8-6-13(7-9-15)24-20(27)25-14-4-3-5-16(10-14)28-2/h3-12H,1-2H3,(H2,24,25,27)

Standard InChI Key:  SFXJOPJCHZOWAT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.7267   -4.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4395   -5.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1526   -4.5974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1500   -3.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4282   -3.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7179   -3.7778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4241   -3.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4229   -4.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1386   -5.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8557   -4.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8529   -3.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1367   -3.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5666   -3.3723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2833   -3.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9970   -3.3668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2864   -4.6084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7074   -5.0321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7067   -5.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9911   -6.2688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9901   -7.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7055   -7.5083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2027   -6.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4209   -6.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4258   -7.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2115   -7.3402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6895   -6.6692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4734   -8.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8631   -3.3540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5804   -3.7633    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
 25 27  1  0
  4 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332850

   1-(3-Methoxyphenyl)-3-[4-(1-methylpyrazolo[3,4-d]pyrimidin-4-yl)oxyphenyl]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: 390.40

Molecular Weight (Monoisotopic): 390.1440

AlogP: 3.81

#Rotatable Bonds: 5

Polar Surface Area: 103.19

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.45

CX Basic pKa: 0.96

CX LogP: 2.95

CX LogD: 2.95

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.54

Np Likeness Score: -1.90

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