Brevianamide F (Cyclo(L-Pro-L-Trp)) is a mycotoxin extracted from Colletotrichum gloeosporioides with anti-bacterial effect. Brevianamide F has PI3Kα inhibitory activity with IC50 of 4.8 µM.

Physicochemical Properties

Molecular Formula	C16H17N3O2
Molecular Weight	283.331
Exact Mass	283.132
Elemental Analysis	C, 67.83; H, 6.05; N, 14.83; O, 11.29
CAS #	38136-70-8
Related CAS #	38136-70-8
PubChem CID	181567
Appearance	White to off-white solid powder
Boiling Point	633.2°C
LogP	1.413
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Heavy Atom Count	21
Complexity	453
Defined Atom Stereocenter Count	2
SMILES	O=C1[C@]([H])(C([H])([H])C2=C([H])N([H])C3=C([H])C([H])=C([H])C([H])=C23)N([H])C([C@]2([H])C([H])([H])C([H])([H])C([H])([H])N21)=O
InChi Key	RYFZBPVMVYTEKZ-KBPBESRZSA-N
InChi Code	InChI=1S/C16H17N3O2/c20-15-14-6-3-7-19(14)16(21)13(18-15)8-10-9-17-12-5-2-1-4-11(10)12/h1-2,4-5,9,13-14,17H,3,6-8H2,(H,18,20)/t13-,14-/m0/s1
Chemical Name	(3S,8aS)-3-(1H-indol-3-ylmethyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Synonyms	Brevianamide F
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

Targets	PI3Kα (IC50 = 4.8 μM)
ln Vitro	Both MSSA and MRSA are moderately active against by brevianamide F[1].
References	[1]. Antibacterial Activity of Endophytic Actinomycetes Isolated from the Medicinal Plant Vochysia divergens (Pantanal, Brazil). Front Microbiol. 2017 Sep 6;8:1642. [2]. Secondary Metabolites and PI3K Inhibitory Activity of Colletotrichum gloeosporioides, a Fungal Endophyte of Uncaria rhynchophylla. Curr Microbiol. 2019 Jul;76(7):904-908.
Additional Infomation	Brevianamide F is a pyrrolopyrazine that is hexahydropyrrolo[1,2-a]pyrazine-1,4-dione bearing an indol-3-ylmethyl substituent at position 3 (the 3S,8aS-diastereomer, obtained by formal cyclocondensation of L-tryptophan and L-proline). It has a role as a metabolite. It is a pyrrolopyrazine, a member of indoles and a dipeptide. Brevianamide F has been reported in Aspergillus versicolor, Exophiala pisciphila, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO: 50~57 mg/mL (176.5~201.2 mM) Ethanol: ~19 mg/mL (~67.1 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (8.82 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (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 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.82 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (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 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (8.82 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	3.5295 mL	17.6473 mL	35.2945 mL
	5 mM	0.7059 mL	3.5295 mL	7.0589 mL
	10 mM	0.3529 mL	1.7647 mL	3.5295 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.