3-(4-(4-(2-methoxyphenyl)piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)benzonitrile

ID: ALA3780765

PubChem CID: 127030110

Max Phase: Preclinical

Molecular Formula: C23H21N7O

Molecular Weight: 411.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1N1CCN(c2ncnc3c2cnn3-c2cccc(C#N)c2)CC1

Standard InChI:  InChI=1S/C23H21N7O/c1-31-21-8-3-2-7-20(21)28-9-11-29(12-10-28)22-19-15-27-30(23(19)26-16-25-22)18-6-4-5-17(13-18)14-24/h2-8,13,15-16H,9-12H2,1H3

Standard InChI Key:  SLJHJMKUVDGUKD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   -2.3155    0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1852   -2.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2781   -3.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8565   -5.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3443   -5.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2537   -4.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6753   -2.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9982    3.0140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2977    3.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2918    5.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0102    6.0138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3063    5.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3004    3.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0160    7.5146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2789    8.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2706    9.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0325   10.5146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3274    9.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3192    8.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5843    7.5313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6193    8.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7423   -4.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9325   -4.5428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  6  1  0
  5  3  1  0
  3  4  2  0
  4  1  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 16 17  1  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  2 16  1  0
 19 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 23 28  1  0
 28 29  1  0
 14 30  1  0
 30 31  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA3780765

   ---

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: 411.47

Molecular Weight (Monoisotopic): 411.1808

AlogP: 3.02

#Rotatable Bonds: 4

Polar Surface Area: 83.10

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.06

CX LogP: 3.66

CX LogD: 3.66

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.51

Np Likeness Score: -2.07

References

1. Siebeneicher H, Bauser M, Buchmann B, Heisler I, Müller T, Neuhaus R, Rehwinkel H, Telser J, Zorn L..  (2016)  Identification of novel GLUT inhibitors.,  26  (7): [PMID:26949183] [10.1016/j.bmcl.2016.02.050]

2. Wang, Dasheng and 6 more authors.  2012-04-26  Development of a novel class of glucose transporter inhibitors.  [PMID:22468970]

3. Siebeneicher, Holger H and 8 more authors.  2016-04-01  Identification of novel GLUT inhibitors.  [PMID:26949183]

4. Granchi, C; Fortunato, S and Minutolo, F.  2016-09-01  Anticancer agents interacting with membrane glucose transporters.  [PMID:28042452]

5. Liu, Kevin G and 10 more authors.  2020-05-28  Discovery and Optimization of Glucose Uptake Inhibitors.  [PMID:32282207]

Source

Source(1):

• Scientific Literature