3-(4-bromophenyl)-6-p-tolyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

ID: ALA4548850

PubChem CID: 22548785

Max Phase: Preclinical

Molecular Formula: C20H14BrN3O2

Molecular Weight: 408.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(-c2cc(C(=O)O)c3c(-c4ccc(Br)cc4)n[nH]c3n2)cc1

Standard InChI:  InChI=1S/C20H14BrN3O2/c1-11-2-4-12(5-3-11)16-10-15(20(25)26)17-18(23-24-19(17)22-16)13-6-8-14(21)9-7-13/h2-10H,1H3,(H,25,26)(H,22,23,24)

Standard InChI Key:  ZSKVLMBZFPQPHV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   27.0540   -2.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8712   -2.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2779   -3.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0943   -3.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5038   -2.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0908   -1.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2757   -1.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6472   -1.9521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8344   -3.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6495   -3.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3210   -2.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4283   -4.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6111   -4.0820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8394   -4.7854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4214   -2.6599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8259   -1.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2779   -1.3488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5346   -1.6836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6234   -2.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0181   -3.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3133   -2.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6059   -3.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6052   -3.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3178   -4.2653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0222   -3.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8979   -4.2660    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  1  8  2  0
  8 16  1  0
 15  9  1  0
  9 10  2  0
 10  1  1  0
  5 11  1  0
  9 12  1  0
 12 13  2  0
 12 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 15  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4548850

   3-(4-bromophenyl)-6-(4-methylphenyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

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: 408.26

Molecular Weight (Monoisotopic): 407.0269

AlogP: 5.06

#Rotatable Bonds: 3

Polar Surface Area: 78.87

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.50

CX Basic pKa: 1.62

CX LogP: 5.31

CX LogD: 2.08

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.50

Np Likeness Score: -1.04

References

1. Bagdanoff JT, Chen Z, Acker M, Chen YN, Chan H, Dore M, Firestone B, Fodor M, Fortanet J, Hentemann M, Kato M, Koenig R, LaBonte LR, Liu S, Mohseni M, Ntaganda R, Sarver P, Smith T, Sendzik M, Stams T, Spence S, Towler C, Wang H, Wang P, Williams SL, LaMarche MJ..  (2019)  Optimization of Fused Bicyclic Allosteric SHP2 Inhibitors.,  62  (4): [PMID:30688462] [10.1021/acs.jmedchem.8b01725]

Source

Source(1):

• Scientific Literature