(2R,4R)-2-(2-Chlorophenyl)-3-(4-(3,5-dimethylisoxazol-4-yl)benzoyl)thiazolidine-4-carboxylic Acid

ID: ALA4176503

Cas Number: 2247372-59-2

PubChem CID: 138319694

Product Number: T649206, Order Now?

Max Phase: Preclinical

Molecular Formula: C22H19ClN2O4S

Molecular Weight: 442.92

Molecule Type: Small molecule

In stock!

Associated Items:

Names and Identifiers

Canonical SMILES:  Cc1noc(C)c1-c1ccc(C(=O)N2[C@@H](c3ccccc3Cl)SC[C@H]2C(=O)O)cc1

Standard InChI:  InChI=1S/C22H19ClN2O4S/c1-12-19(13(2)29-24-12)14-7-9-15(10-8-14)20(26)25-18(22(27)28)11-30-21(25)16-5-3-4-6-17(16)23/h3-10,18,21H,11H2,1-2H3,(H,27,28)/t18-,21+/m0/s1

Standard InChI Key:  RZAMDGBOOPJHJQ-GHTZIAJQSA-N

Molfile:  

     RDKit          2D

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   11.9896   -5.3365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3308   -5.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6194   -5.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6204   -4.5895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9111   -5.8144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3557   -5.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.0744   -6.6236    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.6541   -2.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7789   -1.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.4737   -1.6049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

  1. Parent:

    ALA4176503

    TUG-1375

Associated Targets(Human)

FFAR2 Tchem Free fatty acid receptor 2 (545 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FFAR3 Tchem Free fatty acid receptor 3 (304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FFAR1 Tchem Free fatty acid receptor 1 (4763 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FFAR4 Tchem G-protein coupled receptor 120 (2999 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPARA Tclin Peroxisome proliferator-activated receptor alpha (9197 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPARD Tchem Peroxisome proliferator-activated receptor delta (6293 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NR1H3 Tchem LXR-alpha (2891 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NR1H2 Tchem LXR-beta (3841 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Hepatocyte (1455 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ffar2 Free fatty acid receptor 2 (35 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 442.92Molecular Weight (Monoisotopic): 442.0754AlogP: 4.95#Rotatable Bonds: 4
Polar Surface Area: 83.64Molecular Species: ACIDHBA: 5HBD: 1
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: 3.43CX Basic pKa: 1.41CX LogP: 4.19CX LogD: 0.80
Aromatic Rings: 3Heavy Atoms: 30QED Weighted: 0.61Np Likeness Score: -1.05

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