1-[4-(1H-Pyrazolo[3,4-d]pyrimidin-4-yloxy)-phenyl]-3-pyridin-3-yl-urea

ID: ALA2332861

PubChem CID: 71720012

Max Phase: Preclinical

Molecular Formula: C17H13N7O2

Molecular Weight: 347.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(Oc2ncnc3[nH]ncc23)cc1)Nc1cccnc1

Standard InChI:  InChI=1S/C17H13N7O2/c25-17(23-12-2-1-7-18-8-12)22-11-3-5-13(6-4-11)26-16-14-9-21-24-15(14)19-10-20-16/h1-10H,(H2,22,23,25)(H,19,20,21,24)

Standard InChI Key:  KFUQJGBOFJJPNY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   17.8864  -10.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5992  -11.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3123  -10.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3097   -9.9981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5879   -9.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8776  -10.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5839  -10.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5827  -10.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2983  -11.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0154  -10.8467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0126  -10.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2965   -9.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7263   -9.5997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4431  -10.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1568   -9.5943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4462  -10.8358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8671  -11.2595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8664  -12.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1508  -12.4962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1498  -13.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8652  -13.7357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3625  -12.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5806  -12.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5855  -13.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3713  -13.5677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8493  -12.8967    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:

   

   ALA2332861

   1-[4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl]-3-pyridin-3-ylurea

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: 347.34

Molecular Weight (Monoisotopic): 347.1131

AlogP: 3.18

#Rotatable Bonds: 4

Polar Surface Area: 117.71

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.39

CX Basic pKa: 4.32

CX LogP: 1.76

CX LogD: 1.71

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.52

Np Likeness Score: -1.95

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