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

ID: ALA4125953

PubChem CID: 68259159

Max Phase: Preclinical

Molecular Formula: C20H17N5O2S

Molecular Weight: 391.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1csc(-n2nc(-c3ccccc3)c3ccc(N4CCCC4)nc32)n1

Standard InChI:  InChI=1S/C20H17N5O2S/c26-19(27)15-12-28-20(21-15)25-18-14(17(23-25)13-6-2-1-3-7-13)8-9-16(22-18)24-10-4-5-11-24/h1-3,6-9,12H,4-5,10-11H2,(H,26,27)

Standard InChI Key:  RONGSMANPJPFKO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   33.4622  -11.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4610  -12.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1691  -13.0860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.1673  -11.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8759  -11.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8761  -12.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6548  -12.9253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.1358  -12.2628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6544  -11.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9050  -10.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7056  -10.6559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9580   -9.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4107   -9.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6079   -9.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3592  -10.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9116  -13.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4315  -14.3657    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   35.9120  -15.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6892  -14.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6889  -13.9568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.3927  -15.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3928  -15.9971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.1003  -14.7713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7530  -13.0851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0094  -12.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4621  -13.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8702  -14.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6696  -13.9009    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 28  1  0
 28 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4125953

   2-(3-Phenyl-6-pyrrolidin-1-ylpyrazolo[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: 391.46

Molecular Weight (Monoisotopic): 391.1103

AlogP: 3.84

#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: 4.76

CX LogD: 1.30

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.57

Np Likeness Score: -1.69

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