Compounds > versicolorin a
Page last updated: 2024-12-09

versicolorin a

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

Description

versicolorin A: see also versicolorin [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

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. [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 CID638297
CHEBI ID72676
SCHEMBL ID3272235
MeSH IDM0094888

Synonyms (26)

Synonym
4,6,8-trihydroxy-3a,12a-dihydroanthra[2,3-b]furo[3,2-d]furan-5,10-dione
nsc 274542
z-(-)-4,6,8-trihydroxy-3a,12a-dihydroanthra(2,3-b)furo(3,2-d)furan-5,10-dione
anthra(2,3-b)furo(3,2-d)furan-5,10-dione, 3a,12a-dihydro-4,6,8-trihydroxy-, z-(-)-
versicolorin a
ccris 3475
CHEBI:72676
(3as,12ar)-4,6,8-trihydroxy-3a,12a-dihydroanthra[2,3-b]furo[3,2-d]furan-5,10-dione
6807-96-1
nsc-274542
anthra[2,3-b]furo[3,2-d]furan-5,10-dione, 3a,12a-dihydro-4,6,8-trihydroxy-, (3as-cis)-
unii-du1m9u6126
du1m9u6126 ,
C20583
SCHEMBL3272235
4,6,8-trihydroxy-3a,12a-dihydroanthra[2,3-b]furo[3,2-d]furan-5,10-dione #
SJNDYXPJRUTLNW-ULCDLSAGSA-N
(3as,12ar)-3a,12a-dihydro-4,6,8-trihydroxyanthra(2,3-b)furo(3,2-d)furan-5,10-dione
anthra(2,3-b)furo(3,2-d)furan-5,10-dione, 3a,12a-dihydro-4,6,8-trihydroxy-, (3as,12ar)-
anthra(2,3-b)furo(3,2-d)furan-5,10-dione, 3a,12a-dihydro-4,6,8-trihydroxy-, (3as-cis)-
Q27140069
(4s,8r)-2,16,18-trihydroxy-7,9-dioxapentacyclo[10.8.0.03,10.04,8.014,19]icosa-1,3(10),5,11,14(19),15,17-heptaene-13,20-dione
HY-129247
CS-0104394
anthra[2,3-b]furo[3,2-d]furan-5,10-dione, 3a,12a-dihydro-4,6,8-trihydroxy-, (3as,12ar)-
AKOS040754350

Research Excerpts

Overview

Versicolorin A (VerA) is a precursor of AFB1 biosynthesis and is structurally related to the latter.

ExcerptReferenceRelevance
"Versicolorin A (VerA) is a precursor of AFB1 biosynthesis and is structurally related to the latter."( Mutagenicity and genotoxicity assessment of the emerging mycotoxin Versicolorin A, an Aflatoxin B1 precursor.
Al-Ayoubi, C; Alonso-Jauregui, M; Azqueta, A; Mirey, G; Oswald, IP; Puel, O; Rocher, O; Soler, L; Vettorazzi, A; Vignard, J, 2023)		1.87

Toxicity

ExcerptReferenceRelevance
"Aflatoxins are a group of mycotoxins that have major adverse effects on human health."( Versicolorin A enhances the genotoxicity of aflatoxin B1 in human liver cells by inducing the transactivation of the Ah-receptor.
Al-Ayoubi, C; Brouwer, A; Budin, C; Man, HY; Oswald, IP; Puel, S; Soler, L; van der Burg, B; van Vugt-Lussenburg, BMA, 2021)		2.06
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
carcinogenic agentA role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
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
cyclic acetalAn acetal in the molecule of which the acetal carbon and one or both oxygen atoms thereon are members of a ring.
organic heteropentacyclic compound
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]

Research

Studies (25)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (28.00)18.7374
1990's4 (16.00)18.2507
2000's4 (16.00)29.6817
2010's5 (20.00)24.3611
2020's5 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.48

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 Index11.48 (24.57)
Research Supply Index3.26 (2.92)
Research Growth Index4.74 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.48)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (8.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other23 (92.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
2-acetylaminofluorene
2-Acetylaminofluorene: A hepatic carcinogen whose mechanism of activation involves N-hydroxylation to the aryl hydroxamic acid followed by enzymatic sulfonation to sulfoxyfluorenylacetamide. It is used to study the carcinogenicity and mutagenicity of aromatic amines.		1.97102-acetamidofluorenesantimitotic;
carcinogenic agent;
epitope;
mutagen
furan
furan : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing four carbons and one oxygen, with formula C4H4O. It is a toxic, flammable, low-boiling (31degreeC) colourless liquid.		2.1110furans;
mancude organic heteromonocyclic parent;
monocyclic heteroarene		carcinogenic agent;
hepatotoxic agent;
Maillard reaction product
funiculosin (anthraquinone)
funiculosin (anthraquinone): see also a pyridone cpd called funiculosin; structure		1.9710trihydroxyanthraquinone
carmine
Carmine: Coloring matter from the insect Coccus cacti L. It is used in foods, pharmaceuticals, toiletries, etc., as a dye, and also has use as a microscopic stain and biological marker.		1.9710
ponceau 4r
ponceau 4R: structure in first source		1.9710
norsolorinic acid
norsolorinic acid: isolated from Aspergillus parasiticus. norsolorinic acid : A polyketide that is anthraquinone bearing four hydroxy substituents at positions 1, 3, 6 and 8 as well as a hexanoyl substituent at position 2.		3.4620polyketide;
tetrahydroxyanthraquinone		fungal metabolite
phenyl acetate
phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.		3.0510benzenes;
phenyl acetates
aflatoxicol
aflatoxicol: metabolite of aflatoxin B; RN given refers to (1S-(1alpha,6beta,9abeta))-isomer; structure		2.1710
o-methylsterigmatocystin
[no description available]		3.0710sterigmatocystins
versicolorin c
versicolorin C: RN given refers to versicolorin C (cis-(+-))-isomer; see also record for versicolorin. 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.		2.8940cyclic acetal;
organic heteropentacyclic compound;
p-quinones;
polyphenol		Aspergillus 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.		2.3720acetate ester;
anthrafuran;
lactol;
palmitoyl amino acid;
polyphenol		metabolite
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.		5.52120aflatoxin;
aromatic ether;
aromatic ketone		carcinogenic agent;
human metabolite
averufin
averufin: isolated from Aspergillus sp.; has antifungal activity		2.6530cyclic ketal;
organic heteropentacyclic compound;
polyketide;
polyphenol		fungal metabolite
sterigmatocystin
[no description available]		5.55130sterigmatocystinsmetabolite
5-methoxysterigmatocystin
5-methoxysterigmatocystin: has antineoplastic activity; structure in first source		2.0710sterigmatocystins
aflatoxin g1
aflatoxin G1: RN given refers to (7aR-cis)-isomer & is from 9th CI Form Index		2.1710
aflatoxin m1
Aflatoxin M1: A 4-hydroxylated metabolite of AFLATOXIN B1, one of the MYCOTOXINS from ASPERGILLUS tainted food. It is associated with LIVER damage and cancer resulting from its P450 activation to the epoxide which alkylates DNA. Toxicity depends on the balance of liver enzymes that activate it (CYTOCHROME P-450) and others that detoxify it (GLUTATHIONE S TRANSFERASE) (Pharmac Ther 50.443 1991). Primates & rat are sensitive while mouse and hamster are tolerant (Canc Res 29.236 1969).. aflatoxin M1 : A member of the class of aflatoxins that is aflatoxin B1 in which the hydrogen at position 9a is replaced by a hydroxy group.		3.0710aflatoxin;
aromatic ether;
aromatic ketone;
tertiary alcohol		Aspergillus metabolite;
human xenobiotic metabolite;
mammalian metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
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
Cancer of Liver
[description not available]		02.8910
Liver Neoplasms
Tumors or cancer of the LIVER.		02.8910