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

ID: ALA2332865

PubChem CID: 71575541

Max Phase: Preclinical

Molecular Formula: C18H13FN6O2

Molecular Weight: 364.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H13FN6O2/c19-11-1-3-12(4-2-11)23-18(26)24-13-5-7-14(8-6-13)27-17-15-9-22-25-16(15)20-10-21-17/h1-10H,(H2,23,24,26)(H,20,21,22,25)

Standard InChI Key:  GXAOAPJGDJRCES-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.3132  -24.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0260  -25.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7390  -24.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7364  -23.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0147  -23.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3044  -23.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0109  -23.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0097  -24.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7253  -25.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4424  -24.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4396  -23.8327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7235  -23.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1532  -23.4171    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8699  -23.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5836  -23.4117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8731  -24.6531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2943  -25.0768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2936  -25.9027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5780  -26.3135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5769  -27.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2923  -27.5528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7895  -26.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0077  -26.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0126  -27.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983  -27.3849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2763  -26.7139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4556  -25.0527    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  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
  3 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332865

   1-(4-fluorophenyl)-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: 364.34

Molecular Weight (Monoisotopic): 364.1084

AlogP: 3.93

#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: 3.12

CX LogD: 3.08

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: -1.83

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