Asperphenamate

Names

[ Name ]:
Asperphenamate

[Synonym ]:
Auranamide
N-benzoylphenylalaninyl-N-benzoylphenylalaninate
N-Benzoyl-L-phenylalanine (S)-2-benzoylamino-3-phenylpropyl ester
(2S)-2-(Benzoylamino)-3-phenylpropanoic acid (2S)-2-(benzoylamino)-3-phenylpropyl ester

Biological Activity

[Description]:

Asperphenamate, a fungal metabolite of Aspergillus flatiipes with anti-cancer effect, exhibits IC50 values of 92.3 μM, 96.5 μM and 97.9 μM in T47D, MDA-MB-231 and HL-60 cells, respectively[1][2].

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Metabolic Enzyme/Protease >> Cathepsin

[In Vitro]

Asperphenamate can inhibit cancer cell proliferation by fully inducing autophagy. asperphenamate showed inhibition effects against cathepsin L. At the same time, it also displayed weak inhibitory ability against cathepsin S.

[References]

[1]. Alice M.Clark, et al. Synthesis of asperphenamate, a novel fungal metabolite. Phytochemistry

[2]. LeiYuan, et al. Total synthesis and anticancer activity studies of the stereoisomers of asperphenamate and patriscabratine. Chinese Chemical Letters Volume 21, Issue 2, February 2010, Pages 155-158.

[3]. Yuan L, et al. Discovery of novel cathepsin inhibitors with potent anti-metastatic effects in breast cancer cells. Bioorg Chem. 2018 Dec;81:672-680.

Chemical & Physical Properties

[ Density]:
1.198g/cm3

[ Boiling Point ]:
774.3ºC at 760 mmHg

[ Molecular Formula ]:
C₃₂H₃₀N₂O₄

[ Molecular Weight ]:
506.59200

[ Flash Point ]:
422.1ºC

[ Exact Mass ]:
506.22100

[ PSA ]:
84.50000

[ LogP ]:
5.39400

[ Index of Refraction ]:
1.611