2-(3-((5-Cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)-4-fluorobenzo[d]-thiazole-6-carboxylic Acid; Tropifexor

ID: ALA4062567

Chembl Id: CHEMBL4062567

PubChem CID: 59053728

Max Phase: Preclinical

Molecular Formula: C29H25F4N3O5S

Molecular Weight: 603.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(F)c2nc(N3C4CCC3CC(OCc3c(-c5ccccc5OC(F)(F)F)noc3C3CC3)C4)sc2c1

Standard InChI:  InChI=1S/C29H25F4N3O5S/c30-21-9-15(27(37)38)10-23-25(21)34-28(42-23)36-16-7-8-17(36)12-18(11-16)39-13-20-24(35-41-26(20)14-5-6-14)19-3-1-2-4-22(19)40-29(31,32)33/h1-4,9-10,14,16-18H,5-8,11-13H2,(H,37,38)

Standard InChI Key:  VYLOOGHLKSNNEK-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA4062567

   2-(3-((5-Cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)-4-fluorobenzo[d]thiazole-6-carboxylic acid

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: 603.59

Molecular Weight (Monoisotopic): 603.1451

AlogP: 7.28

#Rotatable Bonds: 8

Polar Surface Area: 97.92

Molecular Species: ACID

HBA: 8

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.58

CX Basic pKa: 0.77

CX LogP: 7.37

CX LogD: 4.02

Aromatic Rings: 4

Heavy Atoms: 42

QED Weighted: 0.21

Np Likeness Score: -0.91

References

1. Tully DC, Rucker PV, Chianelli D, Williams J, Vidal A, Alper PB, Mutnick D, Bursulaya B, Schmeits J, Wu X, Bao D, Zoll J, Kim Y, Groessl T, McNamara P, Seidel HM, Molteni V, Liu B, Phimister A, Joseph SB, Laffitte B..  (2017)  Discovery of Tropifexor (LJN452), a Highly Potent Non-bile Acid FXR Agonist for the Treatment of Cholestatic Liver Diseases and Nonalcoholic Steatohepatitis (NASH).,  60  (24): [PMID:29148806] [10.1021/acs.jmedchem.7b00907]

2. Cao S, Yang X, Zhang Z, Wu J, Chi B, Chen H, Yu J, Feng S, Xu Y, Li J, Zhang Y, Wang X, Wang Y..  (2022)  Discovery of a tricyclic farnesoid X receptor agonist HEC96719, a clinical candidate for treatment of non-alcoholic steatohepatitis.,  230  [PMID:34998040] [10.1016/j.ejmech.2021.114089]

Source

Source(1):

• Scientific Literature