3-(4-amino-3-(naphthalen-1-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-2,2-dimethylpropan-1-ol

ID: ALA4785578

PubChem CID: 162667743

Max Phase: Preclinical

Molecular Formula: C20H21N5O

Molecular Weight: 347.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(CO)Cn1nc(-c2cccc3ccccc23)c2c(N)ncnc21

Standard InChI:  InChI=1S/C20H21N5O/c1-20(2,11-26)10-25-19-16(18(21)22-12-23-19)17(24-25)15-9-5-7-13-6-3-4-8-14(13)15/h3-9,12,26H,10-11H2,1-2H3,(H2,21,22,23)

Standard InChI Key:  YQIFUMVOBHTFKS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   16.7359   -5.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5283   -5.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3180   -4.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2219   -5.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3908   -2.8514    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1563   -3.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7226   -4.2304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1832   -2.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1964   -4.4964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8453   -3.9977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5675   -3.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7470   -3.2506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5217   -4.0389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4136   -1.8763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9370   -2.4964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6697   -1.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8501   -1.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4844   -1.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1156   -1.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7449   -2.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1886   -3.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0071   -3.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3799   -2.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9298   -1.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5526   -6.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8620   -6.9810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  6  2  0
  6  7  1  0
  7 13  2  0
 12  8  2  0
  8  5  1  0
 12 13  1  0
 10 11  2  0
  9 10  1  0
 11 12  1  0
 13  9  1  0
  8 14  1  0
  9  4  1  0
 11 15  1  0
 15 20  2  0
 19 16  2  0
 16 17  1  0
 17 18  2  0
 18 15  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  4  2  1  0
  2 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4785578

   ---

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: 347.42

Molecular Weight (Monoisotopic): 347.1746

AlogP: 3.25

#Rotatable Bonds: 4

Polar Surface Area: 89.85

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.74

CX LogP: 2.99

CX LogD: 2.99

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.59

Np Likeness Score: -0.53

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