3-(naphthalen-1-yl)-1-(piperidin-4-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

ID: ALA4776166

PubChem CID: 162643501

Max Phase: Preclinical

Molecular Formula: C21H22N6

Molecular Weight: 358.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(-c1cccc3ccccc13)nn2CC1CCNCC1

Standard InChI:  InChI=1S/C21H22N6/c22-20-18-19(17-7-3-5-15-4-1-2-6-16(15)17)26-27(21(18)25-13-24-20)12-14-8-10-23-11-9-14/h1-7,13-14,23H,8-12H2,(H2,22,24,25)

Standard InChI Key:  WHROQBPMBHWWTB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    2.8560   -5.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5496   -5.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7226   -3.0619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4881   -3.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0503   -4.4450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5150   -2.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5241   -4.7110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1771   -4.2123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8993   -3.4398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0788   -3.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8494   -4.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7413   -2.0909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2689   -2.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1397   -5.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4482   -5.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4669   -6.8048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1833   -7.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8809   -6.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0015   -1.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1820   -1.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8162   -2.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4475   -1.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0767   -2.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5204   -3.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3389   -3.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7117   -2.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2617   -1.8960    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
  2  1  1  0
  1 14  1  0
  1 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13 23  2  0
 22 19  2  0
 19 20  1  0
 20 21  2  0
 21 13  1  0
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 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4776166

   ---

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: 358.45

Molecular Weight (Monoisotopic): 358.1906

AlogP: 3.23

#Rotatable Bonds: 3

Polar Surface Area: 81.65

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.35

CX LogP: 2.76

CX LogD: -0.02

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.59

Np Likeness Score: -0.68

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