3-(2-Ethoxyquinolin-6-yl)-1-((1-methylpiperidin-4-yl)-methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

ID: ALA4576165

Cas Number: 1951431-22-3

PubChem CID: 122453014

Product Number: B647548, Order Now?

Max Phase: Preclinical

Molecular Formula: C23H27N7O

Molecular Weight: 417.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOc1ccc2cc(-c3nn(CC4CCN(C)CC4)c4ncnc(N)c34)ccc2n1

Standard InChI:  InChI=1S/C23H27N7O/c1-3-31-19-7-5-16-12-17(4-6-18(16)27-19)21-20-22(24)25-14-26-23(20)30(28-21)13-15-8-10-29(2)11-9-15/h4-7,12,14-15H,3,8-11,13H2,1-2H3,(H2,24,25,26)

Standard InChI Key:  AWJAAKKEYXUCFY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    9.7716  -10.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4813  -11.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4825  -11.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2601  -12.2291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5118  -13.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3037  -13.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8812  -12.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6689  -12.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8832  -13.6419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6709  -13.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3057  -14.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5139  -14.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7393  -11.5692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2582  -10.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5117  -10.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9629   -9.5234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2164   -8.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0146   -8.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2639   -7.8004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0662   -7.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3156   -6.8508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1178   -6.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3257   -5.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6108   -8.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3614   -9.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5592   -9.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3098   -9.9613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7740  -12.3894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0685  -11.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0673  -11.1646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
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  5  6  1  0
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  7 13  1  0
  5 14  1  0
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  3 15  1  0
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 21 25  1  0
 25 26  2  0
 19 27  1  0
 26 27  1  0
 27 28  2  0
 16 28  1  0
  4 29  2  0
 29 30  1  0
 30 31  2  0
  2 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4576165

   BKI-1369

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: 417.52

Molecular Weight (Monoisotopic): 417.2277

AlogP: 3.36

#Rotatable Bonds: 5

Polar Surface Area: 94.98

Molecular Species: BASE

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.19

CX LogP: 3.10

CX LogD: 1.31

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.53

Np Likeness Score: -1.27

References

1. Vidadala RS, Rivas KL, Ojo KK, Hulverson MA, Zambriski JA, Bruzual I, Schultz TL, Huang W, Zhang Z, Scheele S, DeRocher AE, Choi R, Barrett LK, Siddaramaiah LK, Hol WG, Fan E, Merritt EA, Parsons M, Freiberg G, Marsh K, Kempf DJ, Carruthers VB, Isoherranen N, Doggett JS, Van Voorhis WC, Maly DJ..  (2016)  Development of an Orally Available and Central Nervous System (CNS) Penetrant Toxoplasma gondii Calcium-Dependent Protein Kinase 1 (TgCDPK1) Inhibitor with Minimal Human Ether-a-go-go-Related Gene (hERG) Activity for the Treatment of Toxoplasmosis.,  59  (13): [PMID:27309760] [10.1021/acs.jmedchem.6b00760]

2. 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