2-(4-chloro-3,5-diphenyl-1H-pyrazol-1-yl)thiazole-4-carboxylic acid

ID: ALA3092152

PubChem CID: 44611633

Max Phase: Preclinical

Molecular Formula: C19H12ClN3O2S

Molecular Weight: 381.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1csc(-n2nc(-c3ccccc3)c(Cl)c2-c2ccccc2)n1

Standard InChI:  InChI=1S/C19H12ClN3O2S/c20-15-16(12-7-3-1-4-8-12)22-23(17(15)13-9-5-2-6-10-13)19-21-14(11-26-19)18(24)25/h1-11H,(H,24,25)

Standard InChI Key:  AHDUYVFZHGOLRU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   22.1186   -6.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1175   -7.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8322   -7.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5487   -7.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5458   -6.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8305   -6.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2583   -6.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0132   -6.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5629   -5.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1477   -5.0872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3414   -5.2618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4783   -4.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2846   -4.1591    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.3677   -3.3384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6126   -3.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0632   -3.6209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.3812   -5.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7188   -6.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5387   -6.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0220   -6.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6794   -5.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8605   -5.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4380   -2.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0488   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6524   -1.9476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1878   -7.2215    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11  7  2  0
  5  7  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  2  0
 10 12  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
  9 17  1  0
 15 23  1  0
 23 24  1  0
 23 25  2  0
  8 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3092152

   2-(4-Chloro-3,5-diphenylpyrazol-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: 381.84

Molecular Weight (Monoisotopic): 381.0339

AlogP: 5.01

#Rotatable Bonds: 4

Polar Surface Area: 68.01

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.17

CX Basic pKa: 0.47

CX LogP: 5.65

CX LogD: 2.20

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.54

Np Likeness Score: -1.29

References

1. Atobe M, Naganuma K, Kawanishi M, Morimoto A, Kasahara K, Ohashi S, Suzuki H, Hayashi T, Miyoshi S..  (2013)  SAR-based optimization of 2-(1H-pyrazol-1-yl)-thiazole derivatives as highly potent EP1 receptor antagonists.,  23  (24): [PMID:24252546] [10.1016/j.bmcl.2013.10.065]

Source

Source(1):

• Scientific Literature