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

ID: ALA4743519

PubChem CID: 162646627

Max Phase: Preclinical

Molecular Formula: C21H25N5O2

Molecular Weight: 379.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccccc1-c1cc(C(=O)NCC(O)CN2CCCC2)c2cn[nH]c2n1

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

Standard InChI Key:  OBYYAVWJEDVZFK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   15.7192  -12.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7181  -13.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4261  -13.7175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4243  -12.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0119  -13.7168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3042  -13.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5967  -13.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5956  -14.5314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3080  -14.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0126  -14.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3057  -12.4888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4219  -11.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1284  -10.8522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7129  -10.8564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1329  -12.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1332  -13.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9118  -13.5567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3929  -12.8943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9114  -12.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1259  -10.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8324   -9.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8300   -8.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5364   -8.3964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2836   -8.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8286   -8.1155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4178   -7.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6191   -7.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5413  -10.0308    0.0000 O   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
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 15  1  0
 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
 21 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4743519

   ---

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: 2.12

#Rotatable Bonds: 6

Polar Surface Area: 94.14

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.96

CX Basic pKa: 8.80

CX LogP: 1.59

CX LogD: 0.42

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.61

Np Likeness Score: -1.69

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