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

ID: ALA4126096

PubChem CID: 68259032

Max Phase: Preclinical

Molecular Formula: C19H15N5O2S

Molecular Weight: 377.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1csc(-n2nc(-c3ccccc3)c3ccc(N4CCC4)nc32)n1

Standard InChI:  InChI=1S/C19H15N5O2S/c25-18(26)14-11-27-19(20-14)24-17-13(7-8-15(21-17)23-9-4-10-23)16(22-24)12-5-2-1-3-6-12/h1-3,5-8,11H,4,9-10H2,(H,25,26)

Standard InChI Key:  VYZFMHDHVMLELE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
   24.0025  -11.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0014  -12.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7136  -13.0984    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7118  -11.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4245  -11.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4248  -12.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2076  -12.9377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.6886  -12.2710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2071  -11.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4578  -10.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2625  -10.6559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5149   -9.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9676   -9.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1606   -9.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9079  -10.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4644  -13.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9802  -14.3863    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.4648  -15.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2461  -14.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2458  -13.9774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9537  -15.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9538  -16.0260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6655  -14.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2892  -13.0974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4988  -12.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2867  -13.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0800  -13.8876    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
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 16  2  0
  7 16  1  0
 19 21  1  0
 21 22  2  0
 21 23  1  0
  2 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4126096

   2-[6-(Azetidin-1-yl)-3-phenylpyrazolo[3,4-b]pyridin-1-yl]-1,3-thiazole-4-carboxylic acid

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: 377.43

Molecular Weight (Monoisotopic): 377.0946

AlogP: 3.45

#Rotatable Bonds: 4

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: 3.16

CX Basic pKa: 0.44

CX LogP: 4.24

CX LogD: 0.79

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.59

Np Likeness Score: -1.76

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