6-(2-Methoxyphenyl)-N-(3-(pyrrolidin-1-yl)propyl)-1H-pyrazolo-[3,4-b]pyridine-4-carboxamide

ID: ALA4762575

PubChem CID: 162660020

Max Phase: Preclinical

Molecular Formula: C21H25N5O2

Molecular Weight: 379.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccccc1-c1cc(C(=O)NCCCN2CCCC2)c2cn[nH]c2n1

Standard InChI:  InChI=1S/C21H25N5O2/c1-28-19-8-3-2-7-15(19)18-13-16(17-14-23-25-20(17)24-18)21(27)22-9-6-12-26-10-4-5-11-26/h2-3,7-8,13-14H,4-6,9-12H2,1H3,(H,22,27)(H,23,24,25)

Standard InChI Key:  ZPTKZOACLUAFLU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   39.0039  -20.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7119  -20.5480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.7101  -18.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2977  -20.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5901  -20.1365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8825  -20.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8814  -21.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5938  -21.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2984  -21.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5916  -19.3193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.7077  -18.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4142  -17.6828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.9988  -17.6870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.4188  -19.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4190  -20.1345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1977  -20.3873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.6787  -19.7248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.1972  -19.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4117  -16.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1182  -16.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1158  -15.6377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8223  -15.2270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.5694  -15.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1144  -14.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7037  -14.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9049  -14.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3000  -18.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3 16  2  0
 15  4  2  0
  4  1  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  2  5  1  0
  6 11  1  0
  4 12  1  0
 12 13  1  0
 12 14  2  0
 15 16  1  0
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 17 18  1  0
 18 19  2  0
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 13 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 23  1  0
 11 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4762575

   ---

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: 379.46

Molecular Weight (Monoisotopic): 379.2008

AlogP: 2.85

#Rotatable Bonds: 7

Polar Surface Area: 83.14

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.02

CX Basic pKa: 9.18

CX LogP: 1.48

CX LogD: 0.01

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.62

Np Likeness Score: -1.67

References

1. Cowen SD,Russell D,Dakin LA,Chen H,Larsen NA,Godin R,Throner S,Zheng X,Molina A,Wu J,Cheung T,Howard T,Garcia-Arenas R,Keen N,Pendleton CS,Pietenpol JA,Ferguson AD.  (2016)  Design, Synthesis, and Biological Activity of Substrate Competitive SMYD2 Inhibitors.,  59  (24): [PMID:28002961] [10.1021/acs.jmedchem.6b01303]

Source

Source(1):

• Scientific Literature