(2R,4R)-3-([1,1'-Biphenyl]-3-carbonyl)-2-(2-chlorophenyl)-thiazolidine-4-carboxylic Acid

ID: ALA4175455

PubChem CID: 145952606

Max Phase: Preclinical

Molecular Formula: C23H18ClNO3S

Molecular Weight: 423.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@@H]1CS[C@H](c2ccccc2Cl)N1C(=O)c1cccc(-c2ccccc2)c1

Standard InChI:  InChI=1S/C23H18ClNO3S/c24-19-12-5-4-11-18(19)22-25(20(14-29-22)23(27)28)21(26)17-10-6-9-16(13-17)15-7-2-1-3-8-15/h1-13,20,22H,14H2,(H,27,28)/t20-,22+/m0/s1

Standard InChI Key:  LETYEXDVBXLJLM-RBBKRZOGSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   18.3868  -20.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2040  -20.1244    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.4583  -19.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7954  -18.8656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1366  -19.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4252  -18.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4262  -18.1185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7169  -19.3434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1615  -18.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7941  -18.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5012  -17.6387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2093  -17.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4239  -16.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8399  -16.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0425  -16.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8324  -17.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4179  -17.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8730  -19.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5757  -18.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5674  -18.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8505  -17.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1507  -18.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8802  -20.1526    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.0487  -17.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4676  -16.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6802  -16.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4727  -17.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0589  -18.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8441  -18.1082    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
 16 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4175455

   ---

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: 423.92

Molecular Weight (Monoisotopic): 423.0696

AlogP: 5.35

#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: 3.75

CX Basic pKa: ┄

CX LogP: 5.50

CX LogD: 2.21

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.61

Np Likeness Score: -0.78

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