Page last updated: 2024-12-07

fumitremorgin a

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

Description

Fumitremorgin A is a tremorgenic mycotoxin produced by the fungus Aspergillus fumigatus. It is a potent inhibitor of the enzyme γ-aminobutyric acid (GABA) transaminase, which is responsible for the breakdown of GABA, a neurotransmitter that plays a role in regulating muscle tone and movement. Fumitremorgin A has been shown to cause tremors, muscle spasms, and other neurological symptoms in animals. It is also a potent immunosuppressant and has been shown to inhibit the growth of cancer cells. The synthesis of fumitremorgin A involves a complex series of enzymatic reactions. The compound has been isolated from a variety of fungal species and is also produced by some bacteria. Fumitremorgin A is studied because of its potential to be used as a therapeutic agent for a variety of diseases, including epilepsy, Parkinson's disease, and cancer. It is also being investigated as a potential tool for studying the role of GABA in the nervous system.'

Fumitremorgin A: isolated from fungus Aspergillus fumigatus; structure given in first source; RN given refers to (5R-(5alpha,10alpha,10aalpha,14aalpha,15balpha))-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

fumitremorgin A : An organic heterohexacyclic compound that is a mycotoxic indole alkaloid obtained by prenylation of the 10-hydroxy group of verruculogen. [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 CID107713
CHEBI ID72766
SCHEMBL ID1887086
MeSH IDM0083271

Synonyms (21)

Synonym
(5r,10s,10ar,14as,15bs)-10a-hydroxy-7-methoxy-2,2-dimethyl-10-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylprop-1-en-1-yl)-1,10,10a,14,14a,15b-hexahydro-12h-3,4-dioxa-5a,11a,15a-triazacycloocta[1,2,3-lm]indeno[5,6-b]fluorene-11,15(h,13h)-dione
CHEBI:72766
5h-12h-3,4-dioxa-5a,11a,15a-triazacyclooct(lm)indeno(5,6-b)fluorene-11,15(2h,13h)-dione, 1,10,10a,14,14a,15b-hexahydro-10a-hydroxy-7-methoxy-2,2-dimethyl-10-((3-methyl-2-butenyl)oxy)-5-(2-methyl-1-propenyl)-, (5r-(5-alpha,10-alpha,10a-alpha,14a-alpha,15b-
fumitremorgin a
5h-12h-3,4-dioxa-5a,11a,15a-triazacyclooct(lm)indeno(5,6-b)fluorene-11,15(2h,13h)-dione, 1,10,10a,14,14a,15b-hexahydro-10a-hydroxy-7-methoxy-2,2-dimethyl-10-((3-methyl-2-butenyl)oxy)-5-(2-methyl-1-propenyl)-, (5r,10s,10ar,14as,15bs)-
NCGC00180170-01
ACON1_001759
brd-8008
BRD-K19808008-001-01-0
brd8008
12626-18-5
SCHEMBL1887086
zr1c7949xt ,
unii-zr1c7949xt
C20564
fumitremorgen a
ncgc00180170-02_c32h41n3o7_5h,12h-3,4-dioxa-5a,11a,15a-triazacyclooct[lm]indeno[5,6-b]fluorene-11,15(2h,13h)-dione, 1,10,10a,14,14a,15b-hexahydro-10a-hydroxy-7-methoxy-2,2-dimethyl-10-[(3-methyl-2-buten-1-yl)oxy]-5-(2-methyl-1-propen-1-yl)-, (5r,10s,10ar,
NCGC00180170-02
DTXSID30925479
Q27140132
(9r,14s,17s,23r,24s)-23-hydroxy-5-methoxy-12,12-dimethyl-24-(3-methylbut-2-enoxy)-9-(2-methylprop-1-enyl)-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.02,7.08,25.015,23.017,21]pentacosa-1(25),2(7),3,5-tetraene-16,22-dione

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" Under light anesthesia with urethane and chloralose, a higher dosage (more than 100 micrograms/kg) was needed to cause clonic and tonic convulsion."( Pharmacological effects of the tremorgenic mycotoxin fumitremorgin A.
Kuga, T; Nishiyama, M, 1986
)
0.52
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
mycotoxinPoisonous substance produced by fungi.
[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 (5)

ClassDescription
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
diolA compound that contains two hydroxy groups, generally assumed to be, but not necessarily, alcoholic. Aliphatic diols are also called glycols.
indole alkaloidAn alkaloid containing an indole skeleton.
organic heterohexacyclic compound
organic peroxideCompounds of structure ROOR' in which R and R' are organic groups.
[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]

Pathways (2)

PathwayProteinsCompounds
fumitremorgin A biosynthesis412
superpathway of fumitremorgin biosynthesis925

Bioassays (5)

Assay IDTitleYearJournalArticle
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (43.75)18.7374
1990's1 (6.25)18.2507
2000's3 (18.75)29.6817
2010's3 (18.75)24.3611
2020's2 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.17

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 Index17.17 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index4.82 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.17)

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%
Other16 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]