BREVIANAMIDE F

O=C1N[C@@H](CC2=CNC3=C2C=CC=C3)C(=O)N4CCC[C@@H]14

InChIKey=RYFZBPVMVYTEKZ-KBPBESRZSA-N

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

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Targets

Primary Target	Pharmacology	Condition	Potency
Mycobacterium bovis BCG 1 Target ID: CHEMBL615052 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26975378	Inhibitor 8504
Staphylococcus aureus 70 Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28932210	Inhibitor 8504

PubMed

Title	Date	PubMed
Saturation mutagenesis on Tyr205 of the cyclic dipeptide C2-prenyltransferase FtmPT1 results in mutants with strongly increased C3-prenylating activity.	2016-12	27311563
Beyond the Diketopiperazine Family with Alternatively Bridged Brevianamide F Analogues.	2015-08-21	26193166
Identification of a brevianamide F reverse prenyltransferase BrePT from Aspergillus versicolor with a broad substrate specificity towards tryptophan-containing cyclic dipeptides.	2013-02	22660767
The fumitremorgin gene cluster of Aspergillus fumigatus: identification of a gene encoding brevianamide F synthetase.	2006-07	16755625

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:59:06 GMT 2025` Edited by `admin` on `Wed Apr 02 08:59:06 GMT 2025`
Record UNII	76XZ426FPP
Record Status	`Validated (UNII)`
Record Version

Name

Type

Language

BREVIANAMIDE F

Common Name

English

CYCLO(L-PRO-L-TRP)

Preferred Name

English

CYCLO-L-TRYPTOPHYL-L-PROLINE

Common Name

English

PROLYLTRYPTOPHANYLDIKETOPIPERAZINE

Systematic Name

English

CYCLO-L-TRP-L-PRO

Common Name

English

(3S,8AS)-HEXAHYDRO-3-(1H-INDOL-3-YLMETHYL)PYRROLO(1,2-A)PYRAZINE-1,4-DIONE

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID10959075