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

ID: ALA2332868

PubChem CID: 71575545

Max Phase: Preclinical

Molecular Formula: C18H13FN6O2

Molecular Weight: 364.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(Oc2ncnc3[nH]ncc23)cc1)Nc1cccc(F)c1

Standard InChI:  InChI=1S/C18H13FN6O2/c19-11-2-1-3-13(8-11)24-18(26)23-12-4-6-14(7-5-12)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:  NMIMNNFWSUROHT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   10.0139   -7.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7266   -8.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4396   -7.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4369   -6.9937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7152   -6.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0051   -7.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7120   -7.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7108   -7.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4263   -8.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1434   -7.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1405   -7.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4245   -6.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8541   -6.5954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5707   -7.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2843   -6.5900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5739   -7.8313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954   -8.2550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9948   -9.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2792   -9.4915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2782  -10.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9935  -10.7307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4905   -9.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7088   -9.4904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7137  -10.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4993  -10.5628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9772   -9.8917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7277   -9.0609    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
  2 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332868

   1-(3-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: -2.08

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