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

ID: ALA2332864

PubChem CID: 71716376

Max Phase: Preclinical

Molecular Formula: C19H22N6O2

Molecular Weight: 366.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCC1CCCCC1)Nc1ccc(Oc2ncnc3[nH]ncc23)cc1

Standard InChI:  InChI=1S/C19H22N6O2/c26-19(20-10-13-4-2-1-3-5-13)24-14-6-8-15(9-7-14)27-18-16-11-23-25-17(16)21-12-22-18/h6-9,11-13H,1-5,10H2,(H2,20,24,26)(H,21,22,23,25)

Standard InChI Key:  VLGJCFHJGFMVLX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   15.1313  -16.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1301  -17.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8449  -17.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5613  -17.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5585  -16.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8431  -15.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2714  -15.8097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9873  -16.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7002  -15.8043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9905  -17.0444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4154  -17.4677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4148  -18.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6998  -18.7031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6988  -19.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4134  -19.9411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9090  -18.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1281  -18.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1329  -19.5249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9178  -19.7733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3953  -19.1029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4162  -16.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1291  -15.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8410  -16.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5518  -15.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5529  -14.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8371  -14.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1201  -14.9739    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
  2 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 18  1  0
 17 12  1  0
 17 18  2  0
 16 17  1  0
 18 19  1  0
 19 20  1  0
 20 16  2  0
  9 21  1  0
 21 22  1  0
 22 23  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332864

   1-(cyclohexylmethyl)-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: 366.43

Molecular Weight (Monoisotopic): 366.1804

AlogP: 3.85

#Rotatable Bonds: 5

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: 3.08

CX LogD: 3.04

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.64

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