1,1-difluoro-2-methylpropan-2-yl 4-{5-[4-(methanesulfonyl)phenyl]-1H-pyrazolo[3,4-c]pyridin-1-yl}piperidine-1-carboxylate

ID: ALA3822488

PubChem CID: 127048820

Max Phase: Preclinical

Molecular Formula: C23H26F2N4O4S

Molecular Weight: 492.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(OC(=O)N1CCC(n2ncc3cc(-c4ccc(S(C)(=O)=O)cc4)ncc32)CC1)C(F)F

Standard InChI:  InChI=1S/C23H26F2N4O4S/c1-23(2,21(24)25)33-22(30)28-10-8-17(9-11-28)29-20-14-26-19(12-16(20)13-27-29)15-4-6-18(7-5-15)34(3,31)32/h4-7,12-14,17,21H,8-11H2,1-3H3

Standard InChI Key:  CYZKSRYMGPWAQR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   -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
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    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
    3.9258   -6.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4147   -6.9642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2000   -7.7307    0.0000 O   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
    5.9963   -8.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4851   -8.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9501   -9.6431    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.2110   -7.5813    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2704   -9.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8057   -8.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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  4  5  2  0
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  4 13  1  0
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 12 19  1  0
 22 25  1  0
 25 26  1  0
 25 27  2  0
 16  2  1  0
  2 28  1  0
 26 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 29 33  1  0
 29 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3822488

   ---

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: 492.55

Molecular Weight (Monoisotopic): 492.1643

AlogP: 4.32

#Rotatable Bonds: 5

Polar Surface Area: 94.39

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.97

CX LogP: 2.11

CX LogD: 2.11

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.53

Np Likeness Score: -1.36

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