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

ID: ALA2332860

PubChem CID: 71575438

Max Phase: Preclinical

Molecular Formula: C18H14N6O2

Molecular Weight: 346.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccccc1)Nc1ccc(Oc2ncnc3[nH]ncc23)cc1

Standard InChI:  InChI=1S/C18H14N6O2/c25-18(22-12-4-2-1-3-5-12)23-13-6-8-14(9-7-13)26-17-15-10-21-24-16(15)19-11-20-17/h1-11H,(H2,22,23,25)(H,19,20,21,24)

Standard InChI Key:  ZCBKNYPBRJBNLL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    7.6623  -10.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3749  -10.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0880  -10.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0854   -9.5590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3636   -9.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6535   -9.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3601   -9.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3590  -10.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0744  -10.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7916  -10.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7888   -9.5763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0726   -9.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5023   -9.1607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2191   -9.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9326   -9.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2221  -10.3968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6435  -10.8205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6428  -11.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9273  -12.0571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9263  -12.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6416  -13.2964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1386  -11.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3570  -12.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3618  -12.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1474  -13.1283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6254  -12.4573    0.0000 N   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
M  END

Alternative Forms

1. Parent:

   

   ALA2332860

   1-phenyl-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: 346.35

Molecular Weight (Monoisotopic): 346.1178

AlogP: 3.79

#Rotatable Bonds: 4

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: 2.98

CX LogD: 2.94

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.52

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