N-(4-(3-Bromopropoxy)phenyl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

ID: ALA4084506

PubChem CID: 137646343

Max Phase: Preclinical

Molecular Formula: C20H18BrN5O

Molecular Weight: 424.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  BrCCCOc1ccc(Nc2ncnc3c2cnn3-c2ccccc2)cc1

Standard InChI:  InChI=1S/C20H18BrN5O/c21-11-4-12-27-17-9-7-15(8-10-17)25-19-18-13-24-26(20(18)23-14-22-19)16-5-2-1-3-6-16/h1-3,5-10,13-14H,4,11-12H2,(H,22,23,25)

Standard InChI Key:  TUXMKPFAMUTGHX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   11.2668  -14.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5512  -14.9739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8490  -14.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8665  -13.7379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5821  -13.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2802  -13.7630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5986  -14.1213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0694  -14.7930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0920  -13.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5955  -12.5228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8024  -15.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3382  -16.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0754  -16.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2727  -17.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7369  -16.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9997  -15.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3070  -12.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3245  -11.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0360  -10.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7382  -11.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7248  -12.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0092  -12.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4538  -10.9390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4672  -10.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1828   -9.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1962   -8.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9118   -8.5131    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  2  0
  7  8  1  0
  7  9  2  0
  3  8  1  0
  4  9  1  0
  5 10  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
  8 11  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 24 25  1  0
 25 26  1  0
 23 24  1  0
 26 27  1  0
 20 23  1  0
 10 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4084506

   ---

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: 424.30

Molecular Weight (Monoisotopic): 423.0695

AlogP: 4.72

#Rotatable Bonds: 7

Polar Surface Area: 64.86

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.25

CX LogP: 4.31

CX LogD: 4.31

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.34

Np Likeness Score: -1.71

References

1. Elshaier YAMM, Shaaban MA, Abd El Hamid MK, Abdelrahman MH, Abou-Salim MA, Elgazwi SM, Halaweish F..  (2017)  Design and synthesis of pyrazolo[3,4-d]pyrimidines: Nitric oxide releasing compounds targeting hepatocellular carcinoma.,  25  (12): [PMID:28487127] [10.1016/j.bmc.2017.03.002]

Source

Source(1):

• Scientific Literature