Asperphenamate is a fungal metabolite from Aspergillus flatiipes with anti-tumor activity, with IC50s of 92.3 μM, 96.5 μM and 97.9 μM against T47D, MDA-MB-231 and HL-60 cells respectively.

Physicochemical Properties

Molecular Formula	C32H30N2O4
Molecular Weight	506.5916
Exact Mass	506.221
CAS #	63631-36-7
PubChem CID	173952
Appearance	White to off-white solid powder
Density	1.198g/cm3
Boiling Point	774.3ºC at 760 mmHg
Flash Point	422.1ºC
Index of Refraction	1.611
LogP	5.394
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	12
Heavy Atom Count	38
Complexity	732
Defined Atom Stereocenter Count	2
SMILES	C1=CC=C(C=C1)C[C@@H](COC(=O)[C@H](CC2=CC=CC=C2)NC(=O)C3=CC=CC=C3)NC(=O)C4=CC=CC=C4
InChi Key	CVULDJMCSSACEO-VMPREFPWSA-N
InChi Code	InChI=1S/C32H30N2O4/c35-30(26-17-9-3-10-18-26)33-28(21-24-13-5-1-6-14-24)23-38-32(37)29(22-25-15-7-2-8-16-25)34-31(36)27-19-11-4-12-20-27/h1-20,28-29H,21-23H2,(H,33,35)(H,34,36)/t28-,29-/m0/s1
Chemical Name	[(2S)-2-benzamido-3-phenylpropyl] (2S)-2-benzamido-3-phenylpropanoate
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	Asperphenamate completely induces autophagy, which suppresses the growth of cancer cells. In addition to having a modest inhibitory impact on cathepsin S, asperphenamate also inhibits cathepsin L.
References	[1]. Synthesis of asperphenamate, a novel fungal metabolite. Phytochemistry. [2]. 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]. Discovery of novel cathepsin inhibitors with potent anti-metastatic effects in breast cancer cells. Bioorg Chem. 2018 Dec;81:672-680.
Additional Infomation	Asperphenamate is a carboxylic ester resulting from the formal condensation of the carboxy group of N-benzoyl-L-phenylalanine with the hydroxy group of N-benzoyl-L-phenylalaninol. A metabolite found in several Pencillium and Aspergillus species, as well as in plants as a product of endophytic fungi. It has a role as an antineoplastic agent. It is a L-phenylalanine derivative, a member of benzamides and a carboxylic ester. It is functionally related to a N-benzoyl-L-phenylalanine and a N-benzoyl-L-phenylalaninol. Asperphenamate has been reported in Begonia nantoensis, Artemisia anomala, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~197.40 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (4.93 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.9740 mL	9.8699 mL	19.7398 mL
	5 mM	0.3948 mL	1.9740 mL	3.9480 mL
	10 mM	0.1974 mL	0.9870 mL	1.9740 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.