Compounds > versicolorin c
Page last updated: 2024-11-07

versicolorin c

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Versicolorin C is a mycotoxin produced by the fungus Aspergillus versicolor. It is a member of the anthraquinone class of compounds, and its structure is characterized by a complex polycyclic aromatic ring system. Versicolorin C has been shown to have a variety of biological activities, including cytotoxic, genotoxic, and immunosuppressive effects. It is known to be a potent inhibitor of DNA synthesis and cell proliferation. The compound is of interest to researchers due to its potential role in the development of cancer and other diseases. Studies investigating its synthesis, biosynthesis, and biological activity aim to understand its mechanisms of action and potential therapeutic applications. Furthermore, understanding the biosynthesis and regulation of versicolorin C production in Aspergillus versicolor is crucial for developing strategies to control the contamination of food and feed by this mycotoxin.'

versicolorin C: RN given refers to versicolorin C (cis-(+-))-isomer; see also record for versicolorin [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

versicolorin B : An organic heteropentacyclic compound that is 2,3,3a,12a-tetrahydroanthra[2,3-b]furo[3,2-d]furan-5,10-dione carrying three hydroxy substituents at positions 4, 6 and 8. [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]

Cross-References

ID SourceID
PubMed CID107849
CHEMBL ID4744009
CHEBI ID72674
MeSH IDM0094890

Synonyms (25)

Synonym
versicolorin b
anthra(2,3-b)furo(3,2-d)furan-5,10-dione, 2,3,3a,12a-tetrahydro-4,6,8-trihydroxy-, (3as-cis)-
anthra(2,3-b)furo(3,2-d)furan-5,10-dione, 2,3,3a,12a-tetrahydro-4,6,8-trihydroxy-, (3as,12ar)-
(3as,12ar)-4,6,8-trihydroxy-2,3,3a,12a-tetrahydroanthra[2,3-b]furo[3,2-d]furan-5,10-dione
CHEBI:72674
anthra(2,3-b)furo(3,2-d)furan-5,10-dione, 2,3,3a,12a-tetrahydro-4,6,8-trihydroxy-, cis-(+-)-
anthra(2,3-b)furo(3,2-d)furan-5,10-dione, 2,3,3a,12a-tetrahydro-4,6,8-trihydroxy-, (3ar,12as)-rel-
versicolorin c
4331-22-0
w81kf41t35 ,
unii-w81kf41t35
16049-49-3
unii-6a6v34kgoc
6a6v34kgoc ,
C20575
BABJNKGTTYCTOO-ULCDLSAGSA-N
anthra[2,3-b]furo[3,2-d]furan-5,10-dione, 2,3,3a,12a-tetrahydro-4,6,8-trihydroxy-, cis-(.+/-.)-
anthra(2,3-b)furo(3,2-d)furan-5,10-dione, 2,3,3a,12a-tetrahydro-4,6,8-trihydroxy-, cis-(-)-
(+/-)-versicolorin b
anthra(2,3-b)furo(3,2-d)furan-5,10-dione, 2,3,3a,12a-tetrahydro-4,6,8-trihydroxy-, cis-(+/-)-
versicolorin b, (+/-)-
Q27140066
DTXSID50936320
(4s,8r)-2,16,18-trihydroxy-7,9-dioxapentacyclo[10.8.0.03,10.04,8.014,19]icosa-1,3(10),11,14(19),15,17-hexaene-13,20-dione
CHEMBL4744009
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
Aspergillus metaboliteAny fungal metabolite produced during a metabolic reaction in the mould, Aspergillus.
[role 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]

Drug Classes (4)

ClassDescription
organic heteropentacyclic compound
cyclic acetalAn acetal in the molecule of which the acetal carbon and one or both oxygen atoms thereon are members of a ring.
polyphenolMembers of the class of phenols that contain 2 or more benzene rings each of which is substituted by at least one hydroxy group.
p-quinonesA quinone in which the two oxo groups of the quinone are located para to each other on the 6-membered quinonoid ring.
[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 (4)

Assay IDTitleYearJournalArticle
AID1733337Antiproliferative activity against human NCI-H157 cells assessed as cell viability at 50 uM measured after 72 hrs by sulforhodamine B assay2021Bioorganic & medicinal chemistry letters, 05-01, Volume: 39Evaluation of the antiproliferative activity of 106 marine microbial metabolites against human lung cancer cells and potential antiproliferative mechanism of purpuride G.
AID1733309Antiproliferative activity against human NCI-H157 cells assessed as reduction in cell viability measured after 72 hrs by sulforhodamine B assay2021Bioorganic & medicinal chemistry letters, 05-01, Volume: 39Evaluation of the antiproliferative activity of 106 marine microbial metabolites against human lung cancer cells and potential antiproliferative mechanism of purpuride G.
AID1733310Antiproliferative activity against human A549 cells assessed as reduction in cell viability measured after 72 hrs by sulforhodamine B assay2021Bioorganic & medicinal chemistry letters, 05-01, Volume: 39Evaluation of the antiproliferative activity of 106 marine microbial metabolites against human lung cancer cells and potential antiproliferative mechanism of purpuride G.
AID1733336Antiproliferative activity against human A549 cells assessed as cell viability at 50 uM measured after 72 hrs by sulforhodamine B assay2021Bioorganic & medicinal chemistry letters, 05-01, Volume: 39Evaluation of the antiproliferative activity of 106 marine microbial metabolites against human lung cancer cells and potential antiproliferative mechanism of purpuride G.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (21.43)18.7374
1990's3 (21.43)18.2507
2000's2 (14.29)29.6817
2010's4 (28.57)24.3611
2020's2 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.11

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.11 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index4.82 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.11)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
lysine
Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.		2.610aspartate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
lysine;
organic molecular entity;
proteinogenic amino acid		algal metabolite;
anticonvulsant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
chrysophanic acid
chrysophanic acid: RN given refers to parent cpd; structure in Merck, 9th ed, #2260. chrysophanol : A trihydroxyanthraquinone that is chrysazin with a methyl substituent at C-3. It has been isolated from Aloe vera and exhibits antiviral and anti-inflammatory activity.		2.3110dihydroxyanthraquinoneanti-inflammatory agent;
antiviral agent;
plant metabolite
physcione
physcione: structure. physcion : A dihydroxyanthraquinone that is 9,10-anthraquinone bearing hydroxy substituents at positions 1 and 8, a methoxy group at position 3, and a methyl group at position 6. It has been widely isolated and characterised from both terrestrial and marine sources.		2.3110dihydroxyanthraquinoneanti-inflammatory agent;
antibacterial agent;
antifungal agent;
antineoplastic agent;
apoptosis inducer;
hepatoprotective agent;
metabolite
versiconal hemiacetal acetate
versiconal hemiacetal acetate: intermediate in biosynthesis of aflatoxin B1; structure in first source. versiconal hemiacetal acetate : An anthrafuran that is 2,3-dihydroanthra[2,3-b]furan-5,10-dione substituted at positions 2, 4, 6 and 8 by hydroxy groups and at position 3 by a 2-acetoxyethyl group. An intermediate in the biosynthesis of aflatoxin.		2.3820acetate ester;
anthrafuran;
lactol;
palmitoyl amino acid;
polyphenol		metabolite
dothistromin
dothistromin: metabolite of peanut pathogen Cercospora arachidicola; RN given refers to (2R-(2alpha,3abeta,12abeta))-isomer; structure given in first source		2.0310anthraquinone
aflatoxin b1
Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.		2.6730aflatoxin;
aromatic ether;
aromatic ketone		carcinogenic agent;
human metabolite
benzofurans
Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.		1.9910
ergosterol
[no description available]		2.31103beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
ergostanoid;
phytosterols		fungal metabolite;
Saccharomyces cerevisiae metabolite
averufin
averufin: isolated from Aspergillus sp.; has antifungal activity		2.420cyclic ketal;
organic heteropentacyclic compound;
polyketide;
polyphenol		fungal metabolite
versicolorin a
versicolorin A: see also versicolorin. versicolorin A : An organic heteropentacyclic compound that is 3a,12a-dihydroanthra[2,3-b]furo[3,2-d]furan-5,10-dione carrying three hydroxy substituents at positions 4, 6 and 8.		2.8940cyclic acetal;
organic heteropentacyclic compound;
p-quinones;
polyphenol		Aspergillus metabolite;
carcinogenic agent
sterigmatocystin
[no description available]		2.0710sterigmatocystinsmetabolite
5-methoxysterigmatocystin
5-methoxysterigmatocystin: has antineoplastic activity; structure in first source		2.0710sterigmatocystins
averantin
averantin: aflatoxin B(1) precursor; structure in first source. averantin : A tetrahydroxyanthraquinone that is 1,3,6,8-tetrahydroxy-9,10-anthraquinone bearing a 1-hydroxyhexyl substituent at position 2.. (S)-averantin : An optically active form of averantin having S-configuration.		2.4620averantin
diorcinol
diorcinol : An aromatic ether that is diphenyl ether in which both phenyl groups are substituted at position 3 by a hydroxy group and at position 5 by a methyl group.		2.3110aromatic ether;
phenols		fungal metabolite;
marine metabolite;
metabolite
versiconal
versiconal: RN not in Chemline 7/83; structure. versiconal : A secondary metabolite that is an intermediate in the biosynthesis of afflatoxin. Can exist as both a tricyclic anthraquinone-hydroxyaldehyde form or as a tetracyclic anthrafuran form.. versiconal hemiacetal : An anthrafuran that is 2,3-dihydroanthra[2,3-b]furan-5,10-dione substituted at positions 2, 4, 6 and 8 by hydroxy groups and at position 3 by a 2-hydroxyethyl group. An intermediate in the biosynthesis of aflatoxin.		1.9810anthrafuran;
lactol;
versiconal
ConditionIndicatedRelationship StrengthStudiesTrials
Astrocytoma, Grade IV
[description not available]		02.1110
Glioblastoma
A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.		02.1110
Adenocarcinoma, Basal Cell
[description not available]		02.0710
Cancer of Lung
[description not available]		02.0710
Adenocarcinoma
A malignant epithelial tumor with a glandular organization.		02.0710
Lung Neoplasms
Tumors or cancer of the LUNG.		02.0710