(2R,4R)-2-(2-Chlorophenyl)-3-(2'-methylbiphenyl-4-carbonyl)thiazolidine-4-carboxylic Acid

ID: ALA4171999

PubChem CID: 145951370

Max Phase: Preclinical

Molecular Formula: C24H20ClNO3S

Molecular Weight: 437.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccccc1-c1ccc(C(=O)N2[C@@H](c3ccccc3Cl)SC[C@H]2C(=O)O)cc1

Standard InChI:  InChI=1S/C24H20ClNO3S/c1-15-6-2-3-7-18(15)16-10-12-17(13-11-16)22(27)26-21(24(28)29)14-30-23(26)19-8-4-5-9-20(19)25/h2-13,21,23H,14H2,1H3,(H,28,29)/t21-,23+/m0/s1

Standard InChI Key:  WQPQTJFLCWWRJD-JTHBVZDNSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   20.2894  -28.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1066  -28.5811    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.3610  -27.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6980  -27.3223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0393  -27.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3278  -27.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3288  -26.5752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6196  -27.8001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0642  -27.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6968  -26.5051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4039  -26.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1120  -25.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3265  -25.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7425  -24.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9452  -24.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7351  -25.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3206  -26.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7757  -27.7921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4784  -27.3767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4701  -26.5588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7531  -26.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0534  -26.5758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7829  -28.6093    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.3651  -24.1853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5752  -23.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9960  -22.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2065  -23.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9994  -23.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5801  -24.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3738  -25.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  5  6  1  1
  6  7  2  0
  6  8  1  0
  3  9  1  1
  4 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  9 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  9  1  0
 18 23  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 15 24  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4171999

   ---

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: 437.95

Molecular Weight (Monoisotopic): 437.0852

AlogP: 5.66

#Rotatable Bonds: 4

Polar Surface Area: 57.61

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.67

CX Basic pKa: ┄

CX LogP: 6.01

CX LogD: 2.69

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.57

Np Likeness Score: -0.75

References

1. Hansen AH, Sergeev E, Bolognini D, Sprenger RR, Ekberg JH, Ejsing CS, McKenzie CJ, Rexen Ulven E, Milligan G, Ulven T..  (2018)  Discovery of a Potent Thiazolidine Free Fatty Acid Receptor 2 Agonist with Favorable Pharmacokinetic Properties.,  61  (21): [PMID:30247908] [10.1021/acs.jmedchem.8b00855]

Source

Source(1):

• Scientific Literature