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

ID: ALA4175443

PubChem CID: 145952174

Max Phase: Preclinical

Molecular Formula: C25H18ClNO3S

Molecular Weight: 447.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@@H]1CS[C@H](c2ccccc2Cl)N1C(=O)c1ccc(C#Cc2ccccc2)cc1

Standard InChI:  InChI=1S/C25H18ClNO3S/c26-21-9-5-4-8-20(21)24-27(22(16-31-24)25(29)30)23(28)19-14-12-18(13-15-19)11-10-17-6-2-1-3-7-17/h1-9,12-15,22,24H,16H2,(H,29,30)/t22-,24+/m0/s1

Standard InChI Key:  HFMMBBOELQDPBN-LADGPHEKSA-N

Molfile:  

     RDKit          2D

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   36.0678  -29.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8850  -29.6872    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   37.1394  -28.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4764  -28.4284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.8177  -28.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1062  -28.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1072  -27.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3980  -28.9062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.8426  -28.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4752  -27.6112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1823  -27.2015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   34.7236  -25.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5135  -26.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0990  -27.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5541  -28.8982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2568  -28.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2485  -27.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5315  -27.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8318  -27.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5613  -29.7154    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.1445  -25.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5645  -24.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9845  -24.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1952  -23.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6160  -22.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8265  -22.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6194  -23.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2001  -24.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
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  5  6  1  1
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  9 18  2  0
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 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4175443

   ---

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: 447.94

Molecular Weight (Monoisotopic): 447.0696

AlogP: 5.08

#Rotatable Bonds: 3

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: 3.30

CX Basic pKa: ┄

CX LogP: 5.97

CX LogD: 2.54

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.57

Np Likeness Score: -0.79

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