(2R,4R)-3-(4-(3,5-Dimethylisoxazol-4-yl)benzoyl)-2-(2-methoxyphenyl)thiazolidine-4-carboxylic Acid

ID: ALA4171813

PubChem CID: 145950070

Max Phase: Preclinical

Molecular Formula: C23H22N2O5S

Molecular Weight: 438.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1[C@H]1SC[C@@H](C(=O)O)N1C(=O)c1ccc(-c2c(C)noc2C)cc1

Standard InChI:  InChI=1S/C23H22N2O5S/c1-13-20(14(2)30-24-13)15-8-10-16(11-9-15)21(26)25-18(23(27)28)12-31-22(25)17-6-4-5-7-19(17)29-3/h4-11,18,22H,12H2,1-3H3,(H,27,28)/t18-,22+/m0/s1

Standard InChI Key:  KPRSLSKWHAJENP-PGRDOPGGSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   42.5847   -7.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4019   -7.0989    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   43.6563   -6.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9933   -5.8400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.3346   -6.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6231   -5.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6241   -5.0930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.9149   -6.3179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.3595   -5.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9921   -5.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6991   -4.6132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.4073   -4.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6218   -3.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0378   -3.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2405   -3.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0304   -4.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6159   -4.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0710   -6.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.7737   -5.8945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.7653   -5.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0484   -4.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3487   -5.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6579   -2.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7826   -1.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0531   -1.5284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.4774   -2.1085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.8513   -2.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4831   -3.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5094   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0782   -7.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.7895   -7.5294    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
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 23  2  0
 15 23  1  0
 27 28  1  0
 24 29  1  0
 18 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4171813

   ---

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: 438.51

Molecular Weight (Monoisotopic): 438.1249

AlogP: 4.31

#Rotatable Bonds: 5

Polar Surface Area: 92.87

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.35

CX Basic pKa: 1.41

CX LogP: 3.31

CX LogD: 0.01

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.63

Np Likeness Score: -0.80

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