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

ID: ALA2332846

PubChem CID: 71575210

Max Phase: Preclinical

Molecular Formula: C19H16N6O3

Molecular Weight: 376.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(NC(=O)Nc2ccc(Oc3ncnc4[nH]ncc34)cc2)c1

Standard InChI:  InChI=1S/C19H16N6O3/c1-27-15-4-2-3-13(9-15)24-19(26)23-12-5-7-14(8-6-12)28-18-16-10-22-25-17(16)20-11-21-18/h2-11H,1H3,(H2,23,24,26)(H,20,21,22,25)

Standard InChI Key:  UKVCFSOPAQDUHB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    4.2569   -3.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2557   -4.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9712   -4.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6883   -4.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6855   -3.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9694   -3.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3991   -3.2468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1158   -3.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8294   -3.2414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1189   -4.4827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5461   -3.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5461   -4.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2620   -4.8864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9766   -4.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9708   -3.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2544   -3.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5402   -4.9066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5396   -5.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8239   -6.1431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8229   -6.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5383   -7.3825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0354   -5.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2537   -6.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2585   -6.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0442   -7.2144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5222   -6.5434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6829   -3.2226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4011   -3.6303    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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  2 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
 15 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332846

   1-(3-methoxyphenyl)-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: 376.38

Molecular Weight (Monoisotopic): 376.1284

AlogP: 3.80

#Rotatable Bonds: 5

Polar Surface Area: 114.05

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: 1.19

CX LogP: 2.82

CX LogD: 2.78

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.49

Np Likeness Score: -1.78

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