ROQUEFORTINE C

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H23N5O2
Molecular Weight	389.4503
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C=C)[C@@]12C[C@@H]3N([C@@H]1NC4=C2C=CC=C4)C(=O)\C(NC3=O)=C/C5=CNC=N5

InChI

InChIKey=SPWSUFUPTSJWNG-JJUKSXGLSA-N

InChI=1S/C22H23N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-9,11-12,17,20,26H,1,10H2,2-3H3,(H,23,24)(H,25,28)/b16-9+/t17-,20-,22+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H23N5O2
Molecular Weight	389.4503
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19286504 | https://www.ncbi.nlm.nih.gov/pubmed/15337583 | https://www.ncbi.nlm.nih.gov/pubmed/2231314 | https://www.ncbi.nlm.nih.gov/pubmed/16019806

Roquefortine C, a cyclopeptide derived from the diketopiperazine cyclo(Trp-dehydroHis), is a secondary metabolite produced by several Penicillium species, especially by Penicillium roqueforti, which is used as starter culture for blue cheese production. Although roquefortine C is frequently detected in the products, it obviously has an insignificant toxicity to humans after ingestion. However, intoxications in dogs and cattle have been reported. Its bacteriostatic activities against Gram-positive bacteria lead to Roquefortine C potential use in antibiotics, but its development as a drug has been stopped due to its neurotoxic effects in mice. Roquefortine C activates P-gp and inhibits P450-3A and other haemoproteins. Roquefortine C can serve as a sensitive biomarker for penitrem A intoxication.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 1A1 32 Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11559041 \| https://www.ncbi.nlm.nih.gov/pubmed/16019806	Inhibitor 8504
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11559041 \| https://www.ncbi.nlm.nih.gov/pubmed/16019806	Inhibitor 8504
P-glycoprotein 1 54 Target ID: CHEMBL4302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16019806	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Penitrem A intoxication 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19286504	Diagnostic		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Silencing of a second dimethylallyltryptophan synthase of Penicillium roqueforti reveals a novel clavine alkaloid gene cluster.	2017-08	28620689
Quinone/hydroquinone meroterpenoids with antitubercular and cytotoxic activities produced by the sponge-derived fungus Gliomastix sp. ZSDS1-F7.	2017-03	27417331
Modeling Growth and Toxin Production of Toxigenic Fungi Signaled in Cheese under Different Temperature and Water Activity Regimes.	2016-12-24	28029129
Validation and application of a liquid chromatography-tandem mass spectrometry based method for the assessment of the co-occurrence of mycotoxins in maize silages from dairy farms in NW Spain.	2016-12	27707355
OxaD: A Versatile Indolic Nitrone Synthase from the Marine-Derived Fungus Penicillium oxalicum F30.	2016-09-07	27505044
Production of the Fusarium Mycotoxin Moniliformin by Penicillium melanoconidium.	2016-06-08	27195914
The capability of fungi isolated from moldy dwellings to produce toxins.	2016	27518891
Using roquefortine C as a biomarker for penitrem A intoxication.	2009-03	19286504
Oxidative metabolism by P450 and function coupling to efflux systems: modulation of mycotoxin toxicity.	2005-04	16019806
Cytotoxicity of occupationally and environmentally relevant mycotoxins.	2004-10-01	15337583
Molecular requirements for inhibition of cytochrome p450 activities by roquefortine.	2001-09	11559041
Antimicrobial action of roquefortine.	1990-01-01	2231314
Acute toxicity studies on roquefortine and PR toxin, metabolites of Penicillium roqueforti, in the mouse.	1978-08	711058

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

The MIC of roquefortine C for gram-positive organisms were about 80 ug/mL cells on the average. The sensitive bacterium Corynebacterium flaccumfaciens was chosen for characterizing the antimicrobial action of the mycotoxin. Addition of low roquefortine C concentrations at the beginning of bacterial growth resulted in prolongation of both the lag and logarithmic phases. High toxin concentrations (100 ug/mL cells) added to growing cells caused prolongation of logarithmic growth and decreased maximum cell density.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:58:35 GMT 2025` Edited by `admin` on `Mon Mar 31 19:58:35 GMT 2025`
Record UNII	4VW6U94XFK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ROQUEFORTINE

Preferred Name

English

ROQUEFORTINE C

Common Name

English

2H-PYRAZINO(1',2':1,5)PYRROLO(2,3-B)INDOLE-1,4(3H,5AH)-DIONE, 10B-(1,1-DIMETHYL-2-PROPEN-1-YL)-6,10B,11,11A-TETRAHYDRO-3-(1H-IMIDAZOL-5-YLMETHYLENE)-, (3E,5AS,10BR,11AS)-

Common Name

English

NSC-292134

Code

English

ROQUEFORTIN

Common Name

English

2H-PYRAZINO(1',2':1,5)PYRROLO(2,3-B)INDOLE-1,4(3H,5AH)-DIONE, 10B-(1,1-DIMETHYL-2-PROPENYL)-6,10B,11,11A-TETRAHYDRO-3-(1H-IMIDAZOL-4-YLMETHYLENE)-, (3E,5AS,10BR,11AS)-

Common Name

English

(-)-ROQUEFORTINE C

Common Name

English

ROQUEFORTINE [HSDB]

Common Name

English

Code System Code Type Description

NSC

292134