1-(cyclopentylmethyl)-3-(1H-indol-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

ID: ALA4798416

PubChem CID: 162675018

Max Phase: Preclinical

Molecular Formula: C19H20N6

Molecular Weight: 332.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(-c1c[nH]c3ccccc13)nn2CC1CCCC1

Standard InChI:  InChI=1S/C19H20N6/c20-18-16-17(14-9-21-15-8-4-3-7-13(14)15)24-25(19(16)23-11-22-18)10-12-5-1-2-6-12/h3-4,7-9,11-12,21H,1-2,5-6,10H2,(H2,20,22,23)

Standard InChI Key:  ATUHHYYEQZBMCD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
   15.1882  -21.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8858  -21.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0465  -18.5308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8120  -19.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3784  -19.9180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8430  -18.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8604  -20.1881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5134  -19.6853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2356  -18.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4110  -18.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1816  -19.7264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0734  -17.5515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6052  -18.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8146  -16.8634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2323  -17.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5425  -17.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4131  -18.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0482  -18.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8131  -18.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9391  -17.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3028  -16.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4291  -21.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8983  -21.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3276  -22.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1237  -22.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
  4  5  1  0
  5 11  2  0
 10  6  2  0
  6  3  1  0
 10 11  1  0
  8  9  2  0
  7  8  1  0
  9 10  1  0
 11  7  1  0
  6 12  1  0
  7  2  1  0
  9 13  1  0
 13 17  1  0
 16 14  1  0
 14 15  1  0
 15 13  2  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  2  1  1  0
  1 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4798416

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 332.41

Molecular Weight (Monoisotopic): 332.1749

AlogP: 3.75

#Rotatable Bonds: 3

Polar Surface Area: 85.41

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.73

CX LogP: 3.43

CX LogD: 3.43

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.60

Np Likeness Score: -0.67

References

1. Gilles P,Kashyap RS,Freitas MJ,Ceusters S,Van Asch K,Janssens A,De Jonghe S,Persoons L,Cobbaut M,Daelemans D,Van Lint J,Voet ARD,De Borggraeve WM.  (2020)  Design, synthesis and biological evaluation of pyrazolo[3,4-d]pyrimidine-based protein kinase D inhibitors.,  205  [PMID:32835918] [10.1016/j.ejmech.2020.112638]

Source

Source(1):

• Scientific Literature