Aurantiamide acetate

Names

[ Name ]:
Aurantiamide acetate

[Synonym ]:
(2S)-2-[(N-Benzoyl-L-phenylalanyl)amino]-3-phenylpropyl acetate
Benzenepropanamide, N-[(1S)-2-(acetyloxy)-1-(phenylmethyl)ethyl]-α-(benzoylamino)-, (αS)-
Asperglaucide

Biological Activity

[Description]:

Aurantiamide acetate (TMC-58A) is a selective and orally active cathepsin inhibitor isolated from Portulaca oleracea L. Aurantiamide acetate has anti-inflammatory activities and can be used for the study of inflammatory diseases[1][2].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Metabolic Enzyme/Protease >> Cathepsin

[In Vitro]

Aurantiamide acetate inhibits cathepsin L (3.4.22.15) and cathepsin B (3.4.22.1) with IC50 of 12 μM and 49 μM, respectiveiy[1].

[References]

[1]. K Isshiki, et al. Aurantiamide Acetate, a Selective Cathepsin Inhibitor, Produced by Aspergillus Penicilloides. Biosci Biotechnol Biochem. 2001 May;65(5):1195-7.

[2]. Chi-Su Yoon, et al. Anti-neuroinflammatory Effect of Aurantiamide Acetate From the Marine Fungus Aspergillus Sp. SF-5921: Inhibition of NF-κB and MAPK Pathways in Lipopolysaccharide-Induced Mouse BV2 Microglial Cells.Int Immunopharmacol. 2014 Dec;23(2):568-74.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
716.1±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₇H₂₈N₂O₄

[ Molecular Weight ]:
444.522

[ Flash Point ]:
386.9±32.9 °C

[ Exact Mass ]:
444.204895

[ PSA ]:
84.50000

[ LogP ]:
4.58

[ Vapour Pressure ]:
0.0±2.3 mmHg at 25°C

[ Index of Refraction ]:
1.587

Safety Information

[ Hazard Codes ]:
Xi

Related Compounds

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