Compounds > pr toxin
Page last updated: 2024-12-08

pr toxin

Description

PR Toxin: mycotoxin from Penicillium roqueforti; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID440907
CHEMBL ID4176158
CHEBI ID7883
MeSH IDM0064778

Synonyms (25)

Synonym
pr toxine [french]
ccris 4938
toxin (penicillium roquefortii)
spiro(naphth(1,2-b)oxirene-5(1ah),2'-oxirane)-3'-carboxaldehyde, 2-(acetyloxy-2,3,3a,4,6,7b-hexahydro-3,3',3a-trimethyl-6-oxo-, (1ar,2r,2'r,3r,3's,3ar,7bs)-
hsdb 7247
toxin pr
spiro(naphthalene-2(1h),2'-oxirane)-3'-carboxaldehyde, 3,5,6,7,8,8a-hexahydro-7-acetoxy-5,6-epoxy-3',8,8a-trimethyl-3-oxo-
pr toxin
pr-toxin
56299-00-4
C06079 ,
AC1L9A5V ,
[(1ar,2r,3r,3's,3ar,5r,7bs)-3'-formyl-3,3',3a-trimethyl-6-oxospiro[2,3,4,7b-tetrahydro-1ah-naphtho[1,2-b]oxirene-5,2'-oxirane]-2-yl] acetate
pr toxine
unii-f9w0x88afm
f9w0x88afm ,
spiro(naphth(1,2-b)oxirene-5(1ah),2'-oxirane)-3'- carboxaldehyde, 2-(acetyloxy-2,3,3a,4,6,7b-hexahydro- 3,3',3a-trimethyl-6-oxo-, (1ar,2r,2'r,3r,3's,3ar,7bs)-
pr-toxin [hsdb]
spiro(naphth(1,2-b)oxirene-5(1ah),2'-oxirane)-3'-carboxaldehyde, 2-(acetyloxy)-2,3,3a,4,6,7b-hexahydro-3,3',3a-trimethyl-6-oxo-, (1ar-(1a.alpha.,2.beta.,3.beta.,3a.beta.,5.beta.(s*),7b.alpha.))-
spiro(naphthalene-2(1h),2'-oxirane)-3'-carboxaldehyde, 3,5,6,7,8,8a-hexahydro-7-acetoxy-5,6-epoxy-3',8,8a- trimethyl-3-oxo-
CHEBI:7883
Q26841183
DTXSID40971740
3'-formyl-3,3',3a-trimethyl-6-oxo-2,3,3a,4,6,7b-hexahydro-1ah-spiro[naphtho[1,2-b]oxirene-5,2'-oxiran]-2-yl acetate
CHEMBL4176158

Research Excerpts

Overview

PR toxin is a well-known isoprenoid mycotoxin. It is almost solely produced by Penicillium roqueforti after growth on food or animal feed.

ExcerptReferenceRelevance
"PR toxin is a well-known isoprenoid mycotoxin almost solely produced by Penicillium roqueforti after growth on food or animal feed. "( Penicillium roqueforti PR toxin gene cluster characterization.
Coton, E; Coton, M; Hidalgo, PI; Meslet-Cladière, L; Piqueras, J; Poirier, E; Ullán, RV, 2017)		2.21
"PR toxin is a secondary metabolite of the fungus Penicillium roqueforti. "( Secondary metabolites resulting from degradation of PR toxin by Penicillium roqueforti.
Chang, SC; Lu, KL; Yeh, SF, 1993)		1.98

Toxicity

ExcerptReferenceRelevance
" Zearalenone was about 3 times more toxic than its analogue zearalenol."( Toxicity of trichothecenes, moniliformin, zearalenone/ol, griseofulvin, patulin, PR toxin and rubratoxin B on protozoan tetrahymena pyriformis.
Cole, RJ; Cutler, HG; Nishie, K, 1989)		0.5
"The toxic effects of PR toxin were observed in mice, rats, anesthetized cats and isolated rat auricle preparations."( Acute toxicity of PR toxin, a mycotoxin from Penicillium roqueforti.
Chen, CF; Chen, FC; Wei, RD, 1982)		0.92
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
oxacycleAny organic heterocyclic compound containing at least one ring oxygen atom.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID1503713Cytotoxicity against human HCT8 cells by MTT assay2017Journal of natural products, 10-27, Volume: 80, Issue:10
Sesquiterpenes from the Endophyte Glomerella cingulata.
AID1503718Cytotoxicity against human A2780 cells by MTT assay2017Journal of natural products, 10-27, Volume: 80, Issue:10
Sesquiterpenes from the Endophyte Glomerella cingulata.
AID1503715Cytotoxicity against human Bel7402 cells by MTT assay2017Journal of natural products, 10-27, Volume: 80, Issue:10
Sesquiterpenes from the Endophyte Glomerella cingulata.
AID1503716Cytotoxicity against human BCG823 cells by MTT assay2017Journal of natural products, 10-27, Volume: 80, Issue:10
Sesquiterpenes from the Endophyte Glomerella cingulata.
AID1503714Cytotoxicity against human HCT116 cells by MTT assay2017Journal of natural products, 10-27, Volume: 80, Issue:10
Sesquiterpenes from the Endophyte Glomerella cingulata.
AID1503717Cytotoxicity against human A549 cells by MTT assay2017Journal of natural products, 10-27, Volume: 80, Issue:10
Sesquiterpenes from the Endophyte Glomerella cingulata.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (37)

TimeframeStudies, This Drug (%)All Drugs %
pre-199015 (40.54)18.7374
1990's5 (13.51)18.2507
2000's9 (24.32)29.6817
2010's8 (21.62)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.40

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index21.40 (24.57)
Research Supply Index3.69 (2.92)
Research Growth Index4.50 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.40)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (5.13%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other37 (94.87%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
patulin
Patulin: 4-Hydroxy-4H-furo(3,2-c)pyran-2(6H)-one. A mycotoxin produced by several species of Aspergillus and Penicillium. It is found in unfermented apple and grape juice and field crops. It has antibiotic properties and has been shown to be carcinogenic and mutagenic and causes chromosome damage in biological systems.. patulin : A furopyran and lactone that is (2H-pyran-3(6H)-ylidene)acetic acid which is substituted by hydroxy groups at positions 2 and 4 and in which the hydroxy group at position 4 has condensed with the carboxy group to give the corresponding bicyclic lactone. A mycotoxin produced by several species of Aspergillus and Penicillium, it has antibiotic properties but has been shown to be carcinogenic and mutagenic.		2.6830furopyran;
gamma-lactone;
lactol		antimicrobial agent;
Aspergillus metabolite;
carcinogenic agent;
mutagen;
mycotoxin;
Penicillium metabolite
2-heptanone
heptan-2-one : A dialkyl ketone with methyl and pentyl as the alkyl groups.		2.0110dialkyl ketone;
methyl ketone		mouse metabolite;
pheromone
2-naphthol
2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.		6.51360naphtholantinematodal drug;
genotoxin;
human urinary metabolite;
human xenobiotic metabolite;
mouse metabolite;
radical scavenger
moniliformin
moniliformin: RN given refers to parent cpd; structure; do not confuse with plant product, moniliformin		6.9710
caprylates
Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.. octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis.		2.0110fatty acid anion 8:0;
straight-chain saturated fatty acid anion		human metabolite;
Saccharomyces cerevisiae metabolite
beta-lactams
2-azetidinone: structure in first source. azetidin-2-one : An unsubstituted beta-lactam compound.. beta-lactam : A lactam in which the amide bond is contained within a four-membered ring, which includes the amide nitrogen and the carbonyl carbon.		3.2510beta-lactam antibiotic allergen;
beta-lactam
costaclavin
costaclavin: RN given refers to (8beta,10beta)-isomer		2.0310
aristolochene
[no description available]		2.4120aristolochene
nsc 259,968
bouvardin: cyclic hexapeptide from plant Bouvardia ternifolia		1.9610
griseofulvin
Griseofulvin: An antifungal agent used in the treatment of TINEA infections.. griseofulvin : An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topical treatment.		6.97101-benzofurans;
antibiotic antifungal drug;
benzofuran antifungal drug;
organochlorine compound;
oxaspiro compound		antibacterial agent;
Penicillium metabolite
ergosterol
[no description available]		2.01103beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
ergostanoid;
phytosterols		fungal metabolite;
Saccharomyces cerevisiae metabolite
mycophenolic acid
Mycophenolic Acid: Compound derived from Penicillium stoloniferum and related species. It blocks de novo biosynthesis of purine nucleotides by inhibition of the enzyme inosine monophosphate dehydrogenase (IMP DEHYDROGENASE). Mycophenolic acid exerts selective effects on the immune system in which it prevents the proliferation of T-CELLS, LYMPHOCYTES, and the formation of antibodies from B-CELLS. It may also inhibit recruitment of LEUKOCYTES to sites of INFLAMMATION.. mycophenolate : A monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of mycophenolic acid.. mycophenolic acid : A member of the class of 2-benzofurans that is 2-benzofuran-1(3H)-one which is substituted at positions 4, 5, 6, and 7 by methyl, methoxy, (2E)-5-carboxy-3-methylpent-2-en-1-yl, and hydroxy groups, respectively. It is an antibiotic produced by Penicillium brevi-compactum, P. stoloniferum, P. echinulatum and related species. An immunosuppressant, it is widely used (partiularly as its sodium salt and as the 2-(morpholin-4-yl)ethyl ester prodrug, mycophenolate mofetil) to prevent tissue rejection following organ transplants and for the treatment of certain autoimmune diseases.		9.05402-benzofurans;
gamma-lactone;
monocarboxylic acid;
phenols		anticoronaviral agent;
antimicrobial agent;
antineoplastic agent;
EC 1.1.1.205 (IMP dehydrogenase) inhibitor;
environmental contaminant;
immunosuppressive agent;
mycotoxin;
Penicillium metabolite;
xenobiotic
sesquiterpenes
[no description available]		8.470
curcumin
Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.		2.1510aromatic ether;
beta-diketone;
diarylheptanoid;
enone;
polyphenol		anti-inflammatory agent;
antifungal agent;
antineoplastic agent;
biological pigment;
contraceptive drug;
dye;
EC 1.1.1.205 (IMP dehydrogenase) inhibitor;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor;
EC 1.8.1.9 (thioredoxin reductase) inhibitor;
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor;
EC 3.5.1.98 (histone deacetylase) inhibitor;
flavouring agent;
food colouring;
geroprotector;
hepatoprotective agent;
immunomodulator;
iron chelator;
ligand;
lipoxygenase inhibitor;
metabolite;
neuroprotective agent;
nutraceutical;
radical scavenger
penicillic acid
Penicillic Acid: A mycotoxin with antibiotic and carcinogenic activity produced by various strains of PENICILLIUM and ASPERGILLUS. It has been found in tobacco, sausages, and corn.		7.4120
zearalenone
Zearalenone: (S-(E))-3,4,5,6,8,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione. One of a group of compounds known under the general designation of resorcylic acid lactones. Cis, trans, dextro and levo forms have been isolated from the fungus Gibberella zeae (formerly Fusarium graminearum). They have estrogenic activity, cause toxicity in livestock as feed contaminant, and have been used as anabolic or estrogen substitutes.. zearalenone : A macrolide comprising a fourteen-membered lactone fused to 1,3-dihydroxybenzene; a potent estrogenic metabolite produced by some Giberella species.		6.9710macrolide;
resorcinols		fungal metabolite;
mycoestrogen
roquefortine
roquefortine: metabolite of Penicillium roqueforti; structure		9.3460pyrroloindole
andrastin a
andrastin A: a farnesyltransferase inhibitor; structure given in first source. andrastin A : A 19-oxo steroid that is that is andrastin B in which the hydroxy group at position 19 has been oxidised to give the corresponding aldehyde. A farnesyltransferase inhibitor produced by Penicillium roqueforti, a filamentous fungus involved in the ripening of several kinds of blue cheeses.		2.0510
ergoline
Ergolines: A series of structurally-related alkaloids that contain the ergoline backbone structure.. ergoline : An indole alkaloid whose structural skeleton is found in many naturally occurring and synthetic ergolines which are known to bind to neurotransmitter receptors, such as dopamine, noradrenaline and serotonin receptors and function as unselective agonists or antagonists at these receptors.		3.0850diamine;
ergoline alkaloid;
indole alkaloid fundamental parent;
indole alkaloid;
organic heterotetracyclic compound
glaucarubin
Glaucarubin: (1 beta,2 alpha,11 beta,12 alpha,15 beta(S))-11,20-Epoxy-1,2,11,12-tetrahydroxy-15-(2-hydroxy-2-methyl-1-oxobutoxy)picras-3-en-16-one. A quassinoid (Simaroubolide) from Simaruba glauca, a tropical shrub. It has been used as an antiamebic agent and is found to be cytotoxic. It may be of use in cancer chemotherapy.		1.9610
phenanthrenes
Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.		1.9610
ConditionIndicatedRelationship StrengthStudiesTrials
Bovine Diseases
[description not available]		01.9610
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