(2R,4R)-2-(2-Chlorophenyl)-3-(4-((2-methoxyphenyl)-ethynyl)benzoyl)thiazolidine-4-carboxylic Acid

ID: ALA4173130

PubChem CID: 145952068

Max Phase: Preclinical

Molecular Formula: C26H20ClNO4S

Molecular Weight: 477.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1C#Cc1ccc(C(=O)N2[C@@H](c3ccccc3Cl)SC[C@H]2C(=O)O)cc1

Standard InChI:  InChI=1S/C26H20ClNO4S/c1-32-23-9-5-2-6-18(23)13-10-17-11-14-19(15-12-17)24(29)28-22(26(30)31)16-33-25(28)20-7-3-4-8-21(20)27/h2-9,11-12,14-15,22,25H,16H2,1H3,(H,30,31)/t22-,25+/m0/s1

Standard InChI Key:  UQIUYRFRTDOYJE-WIOPSUGQSA-N

Molfile:  

     RDKit          2D

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   42.9603  -30.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7775  -30.6530    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   44.0319  -29.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3689  -29.3941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.7101  -29.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9987  -29.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9997  -28.6471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.2905  -29.8720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.7350  -29.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3676  -28.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0747  -28.1673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.7829  -27.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9974  -27.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4134  -26.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6161  -26.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4060  -27.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9915  -28.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.4465  -29.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.1492  -29.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.1409  -28.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.4240  -28.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.7243  -28.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.4537  -30.6812    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   41.0370  -26.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4570  -25.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8770  -25.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0877  -24.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5084  -23.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7189  -23.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5119  -24.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0926  -25.3249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8873  -26.1159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.0997  -26.3336    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
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 15 16  1  0
 16 17  2  0
 17 12  1  0
  9 18  2  0
 18 19  1  0
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 20 21  1  0
 21 22  2  0
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 18 23  1  0
 24 25  3  0
 15 24  1  0
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 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 31 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4173130

   ---

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: 477.97

Molecular Weight (Monoisotopic): 477.0802

AlogP: 5.09

#Rotatable Bonds: 4

Polar Surface Area: 66.84

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.29

CX Basic pKa: ┄

CX LogP: 5.81

CX LogD: 2.38

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.53

Np Likeness Score: -0.76

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