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

ID: ALA4776502

PubChem CID: 162643288

Max Phase: Preclinical

Molecular Formula: C20H22ClN5O

Molecular Weight: 383.88

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NCCCN1CCCC1)c1cc(-c2ccccc2Cl)nc2[nH]ncc12

Standard InChI:  InChI=1S/C20H22ClN5O/c21-17-7-2-1-6-14(17)18-12-15(16-13-23-25-19(16)24-18)20(27)22-8-5-11-26-9-3-4-10-26/h1-2,6-7,12-13H,3-5,8-11H2,(H,22,27)(H,23,24,25)

Standard InChI Key:  HSHKWFFHJKFLNK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   28.1669  -20.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1658  -20.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8738  -21.2579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8720  -19.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4596  -21.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7520  -20.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0444  -21.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0433  -22.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7557  -22.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4603  -22.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7535  -20.0292    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   28.8696  -18.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5761  -18.3926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1607  -18.3969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5806  -20.0258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5809  -20.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3596  -21.0972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.8406  -20.4347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.3591  -19.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5736  -17.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2801  -17.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2777  -16.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9842  -15.9369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7313  -16.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2763  -15.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8656  -14.9494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0668  -15.1218    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
 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
M  END

Alternative Forms

1. Parent:

   

   ALA4776502

   ---

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: 383.88

Molecular Weight (Monoisotopic): 383.1513

AlogP: 3.49

#Rotatable Bonds: 6

Polar Surface Area: 73.91

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.02

CX Basic pKa: 9.18

CX LogP: 2.24

CX LogD: 0.77

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: -1.97

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