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

ID: ALA4128163

PubChem CID: 68259039

Max Phase: Preclinical

Molecular Formula: C17H9F3N4O2S

Molecular Weight: 390.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1csc(-n2nc(-c3ccccc3)c3ncc(C(F)(F)F)cc32)n1

Standard InChI:  InChI=1S/C17H9F3N4O2S/c18-17(19,20)10-6-12-14(21-7-10)13(9-4-2-1-3-5-9)23-24(12)16-22-11(8-27-16)15(25)26/h1-8H,(H,25,26)

Standard InChI Key:  UPPDSPSCYQRYKM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   35.4173   -4.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1254   -5.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1236   -3.4377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.8322   -3.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8325   -4.6616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6111   -4.9143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.0921   -4.2518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.6107   -3.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8613   -2.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6620   -2.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9143   -1.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3670   -1.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5642   -1.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3156   -2.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8679   -5.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3878   -6.3547    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   37.8684   -7.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6455   -6.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6452   -5.9458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.3490   -7.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3491   -7.9862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.0567   -6.7603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7093   -5.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0019   -4.6650    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   34.7086   -5.8913    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   33.9960   -5.4768    0.0000 F   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
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 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
 24 26  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4128163

   2-[3-Phenyl-6-(trifluoromethyl)pyrazolo[4,3-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: 390.35

Molecular Weight (Monoisotopic): 390.0398

AlogP: 4.26

#Rotatable Bonds: 3

Polar Surface Area: 80.90

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.16

CX Basic pKa: 0.01

CX LogP: 4.54

CX LogD: 1.09

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.57

Np Likeness Score: -1.59

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