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

ID: ALA4175033

PubChem CID: 145951076

Max Phase: Preclinical

Molecular Formula: C22H20N2O4S

Molecular Weight: 408.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1noc(C)c1-c1ccc(C(=O)N2[C@@H](c3ccccc3)SC[C@H]2C(=O)O)cc1

Standard InChI:  InChI=1S/C22H20N2O4S/c1-13-19(14(2)28-23-13)15-8-10-16(11-9-15)20(25)24-18(22(26)27)12-29-21(24)17-6-4-3-5-7-17/h3-11,18,21H,12H2,1-2H3,(H,26,27)/t18-,21+/m0/s1

Standard InChI Key:  WDIDYNSUIJBGIF-GHTZIAJQSA-N

Molfile:  

     RDKit          2D

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   28.8617   -6.9255    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.1160   -6.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4531   -5.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.7943   -6.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0829   -5.7368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0839   -4.9197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3747   -6.1446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8192   -5.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4518   -4.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1589   -4.4398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8670   -4.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0816   -3.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4976   -2.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7003   -3.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4901   -3.9057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0757   -4.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5307   -6.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2334   -5.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2251   -4.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5082   -4.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8084   -4.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1177   -2.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2424   -1.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5129   -1.3551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9372   -1.9351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3110   -2.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9428   -3.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9691   -1.3496    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
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  3  9  1  1
  4 10  1  0
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 15 16  1  0
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  9 18  2  0
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 20 21  1  0
 21 22  2  0
 22  9  1  0
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 24 25  2  0
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 26 27  1  0
 27 23  2  0
 15 23  1  0
 27 28  1  0
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4175033

   ---

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: 408.48

Molecular Weight (Monoisotopic): 408.1144

AlogP: 4.30

#Rotatable Bonds: 4

Polar Surface Area: 83.64

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.47

CX Basic pKa: 1.41

CX LogP: 3.59

CX LogD: 0.20

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.69

Np Likeness Score: -0.88

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