2-(6-(dimethylamino)-3-phenyl-1H-pyrazolo[3,4-b]pyridin-1-yl)thiazole-4-carboxylic acid

ID: ALA4129401

PubChem CID: 145961578

Max Phase: Preclinical

Molecular Formula: C19H17N5O2S

Molecular Weight: 379.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc2c(-c3ccccc3)nn(Cc3nc(C(=O)O)cs3)c2n1

Standard InChI:  InChI=1S/C19H17N5O2S/c1-23(2)15-9-8-13-17(12-6-4-3-5-7-12)22-24(18(13)21-15)10-16-20-14(11-27-16)19(25)26/h3-9,11H,10H2,1-2H3,(H,25,26)

Standard InChI Key:  JRZTVZHVIPMUEC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   13.7753  -12.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7741  -13.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4822  -13.7092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4804  -12.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1890  -12.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1893  -13.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9679  -13.5485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4489  -12.8860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9675  -12.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2181  -11.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0188  -11.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2711  -10.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7239   -9.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9210  -10.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6724  -10.8445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2248  -14.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0248  -14.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3638  -15.2377    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.1761  -15.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3427  -14.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6332  -13.9432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0472  -13.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7585  -14.3358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0399  -13.1164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0661  -13.7083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3587  -13.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0654  -14.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  9 10  1  0
  7 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 17  2  0
 20 22  1  0
 22 23  2  0
 22 24  1  0
  2 25  1  0
 25 26  1  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4129401

   ---

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: 379.45

Molecular Weight (Monoisotopic): 379.1103

AlogP: 3.37

#Rotatable Bonds: 5

Polar Surface Area: 84.14

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.19

CX Basic pKa: 1.37

CX LogP: 3.68

CX LogD: 0.36

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.57

Np Likeness Score: -1.66

References

1. Atobe M, Naganuma K, Kawanishi M, Hayashi T, Suzuki H, Nishida M, Arai H..  (2018)  Discovery of a novel 2-(1H-pyrazolo[3,4-b]pyridin-1-yl)thiazole derivative as an EP1 receptor antagonist and in vivo studies in a bone fracture model.,  28  (14): [PMID:29934246] [10.1016/j.bmcl.2018.06.022]

Source

Source(1):

• Scientific Literature