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

ID: ALA3092155

PubChem CID: 44611631

Max Phase: Preclinical

Molecular Formula: C19H13N3O3S

Molecular Weight: 363.40

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H13N3O3S/c23-17-15(12-7-3-1-4-8-12)21-22(16(17)13-9-5-2-6-10-13)19-20-14(11-26-19)18(24)25/h1-11,23H,(H,24,25)

Standard InChI Key:  RMIFJFCVPBUPGD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   15.2522  -13.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2510  -14.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9658  -14.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6822  -14.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6794  -13.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9640  -13.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3919  -13.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1468  -13.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6965  -12.8624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2813  -12.1494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4751  -12.3241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6119  -11.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4181  -11.2214    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.5012  -10.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7462  -10.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1967  -10.6831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5147  -12.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8523  -13.7004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6723  -13.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1556  -13.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8129  -12.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9940  -12.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5715   -9.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1824   -8.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7859   -9.0099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3213  -14.2838    0.0000 O   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:

   

   ALA3092155

   2-(4-Hydroxy-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: 363.40

Molecular Weight (Monoisotopic): 363.0678

AlogP: 4.07

#Rotatable Bonds: 4

Polar Surface Area: 88.24

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.16

CX Basic pKa: 0.28

CX LogP: 4.74

CX LogD: -0.17

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.57

Np Likeness Score: -1.00

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