1-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]-5-[4-(methanesulfonyl)phenyl]-1H-pyrazolo[3,4-c]pyridine

ID: ALA3824187

PubChem CID: 68022035

Max Phase: Preclinical

Molecular Formula: C24H26N6O2S

Molecular Weight: 462.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1cnc(N2CCC(n3ncc4cc(-c5ccc(S(C)(=O)=O)cc5)ncc43)CC2)nc1

Standard InChI:  InChI=1S/C24H26N6O2S/c1-3-17-13-26-24(27-14-17)29-10-8-20(9-11-29)30-23-16-25-22(12-19(23)15-28-30)18-4-6-21(7-5-18)33(2,31)32/h4-7,12-16,20H,3,8-11H2,1-2H3

Standard InChI Key:  UGNWKIREOVBGOL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -8.5582    3.1350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5199    3.7367    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5222    4.9367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6168    1.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9144    0.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2151    1.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2185    2.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6204    2.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1852   -2.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2781   -3.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8565   -5.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3443   -5.3916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2537   -4.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6753   -2.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5602    4.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9230   -6.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0155   -7.9707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5961   -9.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0842   -9.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -8.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4111   -6.9651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6679  -10.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8586  -11.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  9  1  0
  8  6  1  0
  6  7  2  0
  7  4  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  8  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  4 13  1  0
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 12 19  1  0
 16  2  1  0
  2 25  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 22 26  1  0
 29 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3824187

   1-[1-(5-Ethylpyrimidin-2-yl)piperidin-4-yl]-5-(4-methylsulfonylphenyl)pyrazolo[3,4-c]pyridine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 462.58

Molecular Weight (Monoisotopic): 462.1838

AlogP: 3.70

#Rotatable Bonds: 5

Polar Surface Area: 93.87

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.03

CX LogP: 2.71

CX LogD: 2.71

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.45

Np Likeness Score: -1.52

References

1. Matsuda D, Kobashi Y, Mikami A, Kawamura M, Shiozawa F, Kawabe K, Hamada M, Oda K, Nishimoto S, Kimura K, Miyoshi M, Takayama N, Kakinuma H, Ohtake N..  (2016)  Design and synthesis of 1H-pyrazolo[3,4-c]pyridine derivatives as a novel structural class of potent GPR119 agonists.,  26  (15): [PMID:27390068] [10.1016/j.bmcl.2016.06.050]

2. Matsuda D, Kobashi Y, Mikami A, Kawamura M, Shiozawa F, Kawabe K, Hamada M, Nishimoto S, Kimura K, Miyoshi M, Takayama N, Kakinuma H, Ohtake N..  (2017)  Novel 3H-[1,2,3]triazolo[4,5-c]pyridine derivatives as GPR119 agonists: Synthesis and structure-activity/solubility relationships.,  25  (16): [PMID:28662959] [10.1016/j.bmc.2017.06.014]

Source

Source(1):

• Scientific Literature