Page last updated: 2024-12-07

territrem b

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Description

territrem B: tremorgenic mycotoxin from Aspergillus terreus; RN given refers to (4aR-(4aalpha,6abeta,12aalpha,12bbeta))-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID114734
CHEMBL ID24686
SCHEMBL ID2379608
MeSH IDM0120339

Synonyms (20)

Synonym
4h,11h-naphtho(2,1-b)pyrano(3,4-e)pyran-1,11(5h)-dione, 4a,6,6a,12,12a,12b-hexahydro-4a,12a-dihydroxy-4,4,6a,12b-tetramethyl-9-(3,4,5-trimethoxyphenyl)-, (4ar,6ar,12as,12bs)-
4h,11h-naphtho(2,1-b)pyrano(3,4-e)pyran-1,11(5h)-dione, 4a,6,6a,12,12a,12b-hexahydro-4a,12a-dihydroxy-4,4,6a,12b-tetramethyl-9-(3,4,5-trimethoxyphenyl)-, (4ar-(4a-alpha,6a-beta,12a-alpha,12b-beta))-
territrem b
territreme b
70407-20-4
4a,12a-dihydroxy-4,4,6a,12b-tetramethyl-9-(3,4,5-trimethoxy-phenyl)-4a,6,6a,12,12a,12b-hexahydro-4h,5h-7,10-dioxa-benzo[a]anthracene-1,11-dione
bdbm50089616
CHEMBL24686 ,
(4ar,6ar,12as,12bs)-4a,12a-dihydroxy-4,4,6a,12b-tetramethyl-9-(3,4,5-trimethoxyphenyl)-4a,6,6a,12,12a,12b-hexahydro-4h,11h-benzo[f]pyrano[4,3-b]chromene-1,11(5h)-dione
4M0F
SCHEMBL2379608
HB4104
1YK ,
(4ar,6ar,12as,12bs)-4a,6,6a,12,12a,12b-hexahydro-4a,12a-dihydroxy-4,4,6a,12b-tetramethyl-9-(3,4,5-trimethoxyphenyl)-4h,11h-naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(5h)-dione
territremb(rg)
(1s,2s,7r,10r)-1,7-dihydroxy-2,6,6,10-tetramethyl-14-(3,4,5-trimethoxyphenyl)-11,15-dioxatetracyclo[8.8.0.02,7.012,17]octadeca-4,12(17),13-triene-3,16-dione
Q27452580
DTXSID80897213
CS-0107169
HY-126765

Research Excerpts

Overview

Territrem B (TRB) is a fungal metabolite isolated from Aspergillus terreus. It is a potent and irreversible inhibitor of acetylcholinesterase (AChE)

ExcerptReferenceRelevance
"Territrem B (TRB) is a fungal metabolite isolated from Aspergillus terreus shown previously to be a potent and irreversible inhibitor of acetylcholinesterase (AChE). "( Territrem B, a tremorgenic mycotoxin that inhibits acetylcholinesterase with a noncovalent yet irreversible binding mechanism.
Chen, JW; Hwang, MJ; Ling, KH; Luo, YL; Peng, FC, 1999
)
3.19
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AcetylcholinesteraseElectrophorus electricus (electric eel)IC50 (µMol)0.26000.00000.94539.9400AID398414; AID398849
AcetylcholinesteraseMus musculus (house mouse)Ki0.00170.00001.42829.3000AID1800423
AcetylcholinesteraseHomo sapiens (human)IC50 (µMol)0.00720.00000.933210.0000AID1254738; AID31497; AID594820
AcetylcholinesteraseHomo sapiens (human)Ki0.00170.00001.27869.7300AID1056366; AID1800423
Dipeptidyl peptidase 4Homo sapiens (human)IC50 (µMol)0.00760.00010.444410.0000AID1254738
Sterol O-acyltransferase 1Homo sapiens (human)IC50 (µMol)50.00000.02501.79758.0000AID31814
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (41)

Processvia Protein(s)Taxonomy
acetylcholine catabolic process in synaptic cleftAcetylcholinesteraseHomo sapiens (human)
regulation of receptor recyclingAcetylcholinesteraseHomo sapiens (human)
osteoblast developmentAcetylcholinesteraseHomo sapiens (human)
acetylcholine catabolic processAcetylcholinesteraseHomo sapiens (human)
cell adhesionAcetylcholinesteraseHomo sapiens (human)
nervous system developmentAcetylcholinesteraseHomo sapiens (human)
synapse assemblyAcetylcholinesteraseHomo sapiens (human)
receptor internalizationAcetylcholinesteraseHomo sapiens (human)
negative regulation of synaptic transmission, cholinergicAcetylcholinesteraseHomo sapiens (human)
amyloid precursor protein metabolic processAcetylcholinesteraseHomo sapiens (human)
positive regulation of protein secretionAcetylcholinesteraseHomo sapiens (human)
retina development in camera-type eyeAcetylcholinesteraseHomo sapiens (human)
acetylcholine receptor signaling pathwayAcetylcholinesteraseHomo sapiens (human)
positive regulation of cold-induced thermogenesisAcetylcholinesteraseHomo sapiens (human)
behavioral fear responseDipeptidyl peptidase 4Homo sapiens (human)
response to hypoxiaDipeptidyl peptidase 4Homo sapiens (human)
proteolysisDipeptidyl peptidase 4Homo sapiens (human)
cell adhesionDipeptidyl peptidase 4Homo sapiens (human)
positive regulation of cell population proliferationDipeptidyl peptidase 4Homo sapiens (human)
negative regulation of extracellular matrix disassemblyDipeptidyl peptidase 4Homo sapiens (human)
peptide hormone processingDipeptidyl peptidase 4Homo sapiens (human)
receptor-mediated endocytosis of virus by host cellDipeptidyl peptidase 4Homo sapiens (human)
T cell costimulationDipeptidyl peptidase 4Homo sapiens (human)
regulation of cell-cell adhesion mediated by integrinDipeptidyl peptidase 4Homo sapiens (human)
locomotory exploration behaviorDipeptidyl peptidase 4Homo sapiens (human)
psychomotor behaviorDipeptidyl peptidase 4Homo sapiens (human)
T cell activationDipeptidyl peptidase 4Homo sapiens (human)
endothelial cell migrationDipeptidyl peptidase 4Homo sapiens (human)
symbiont entry into host cellDipeptidyl peptidase 4Homo sapiens (human)
receptor-mediated virion attachment to host cellDipeptidyl peptidase 4Homo sapiens (human)
negative chemotaxisDipeptidyl peptidase 4Homo sapiens (human)
membrane fusionDipeptidyl peptidase 4Homo sapiens (human)
negative regulation of neutrophil chemotaxisDipeptidyl peptidase 4Homo sapiens (human)
glucagon processingDipeptidyl peptidase 4Homo sapiens (human)
cholesterol metabolic processSterol O-acyltransferase 1Homo sapiens (human)
cholesterol metabolic processSterol O-acyltransferase 1Homo sapiens (human)
macrophage derived foam cell differentiationSterol O-acyltransferase 1Homo sapiens (human)
cholesterol storageSterol O-acyltransferase 1Homo sapiens (human)
cholesterol effluxSterol O-acyltransferase 1Homo sapiens (human)
very-low-density lipoprotein particle assemblySterol O-acyltransferase 1Homo sapiens (human)
low-density lipoprotein particle clearanceSterol O-acyltransferase 1Homo sapiens (human)
cholesterol homeostasisSterol O-acyltransferase 1Homo sapiens (human)
positive regulation of amyloid precursor protein biosynthetic processSterol O-acyltransferase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (23)

Processvia Protein(s)Taxonomy
amyloid-beta bindingAcetylcholinesteraseHomo sapiens (human)
acetylcholinesterase activityAcetylcholinesteraseHomo sapiens (human)
cholinesterase activityAcetylcholinesteraseHomo sapiens (human)
protein bindingAcetylcholinesteraseHomo sapiens (human)
collagen bindingAcetylcholinesteraseHomo sapiens (human)
hydrolase activityAcetylcholinesteraseHomo sapiens (human)
serine hydrolase activityAcetylcholinesteraseHomo sapiens (human)
acetylcholine bindingAcetylcholinesteraseHomo sapiens (human)
protein homodimerization activityAcetylcholinesteraseHomo sapiens (human)
laminin bindingAcetylcholinesteraseHomo sapiens (human)
virus receptor activityDipeptidyl peptidase 4Homo sapiens (human)
protease bindingDipeptidyl peptidase 4Homo sapiens (human)
aminopeptidase activityDipeptidyl peptidase 4Homo sapiens (human)
serine-type endopeptidase activityDipeptidyl peptidase 4Homo sapiens (human)
signaling receptor bindingDipeptidyl peptidase 4Homo sapiens (human)
protein bindingDipeptidyl peptidase 4Homo sapiens (human)
serine-type peptidase activityDipeptidyl peptidase 4Homo sapiens (human)
dipeptidyl-peptidase activityDipeptidyl peptidase 4Homo sapiens (human)
identical protein bindingDipeptidyl peptidase 4Homo sapiens (human)
protein homodimerization activityDipeptidyl peptidase 4Homo sapiens (human)
chemorepellent activityDipeptidyl peptidase 4Homo sapiens (human)
fatty-acyl-CoA bindingSterol O-acyltransferase 1Homo sapiens (human)
sterol O-acyltransferase activitySterol O-acyltransferase 1Homo sapiens (human)
protein bindingSterol O-acyltransferase 1Homo sapiens (human)
cholesterol bindingSterol O-acyltransferase 1Homo sapiens (human)
cholesterol O-acyltransferase activitySterol O-acyltransferase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (24)

Processvia Protein(s)Taxonomy
extracellular regionAcetylcholinesteraseHomo sapiens (human)
basement membraneAcetylcholinesteraseHomo sapiens (human)
extracellular spaceAcetylcholinesteraseHomo sapiens (human)
nucleusAcetylcholinesteraseHomo sapiens (human)
Golgi apparatusAcetylcholinesteraseHomo sapiens (human)
plasma membraneAcetylcholinesteraseHomo sapiens (human)
cell surfaceAcetylcholinesteraseHomo sapiens (human)
membraneAcetylcholinesteraseHomo sapiens (human)
neuromuscular junctionAcetylcholinesteraseHomo sapiens (human)
synaptic cleftAcetylcholinesteraseHomo sapiens (human)
synapseAcetylcholinesteraseHomo sapiens (human)
perinuclear region of cytoplasmAcetylcholinesteraseHomo sapiens (human)
side of membraneAcetylcholinesteraseHomo sapiens (human)
extracellular regionDipeptidyl peptidase 4Homo sapiens (human)
lysosomal membraneDipeptidyl peptidase 4Homo sapiens (human)
plasma membraneDipeptidyl peptidase 4Homo sapiens (human)
focal adhesionDipeptidyl peptidase 4Homo sapiens (human)
cell surfaceDipeptidyl peptidase 4Homo sapiens (human)
membraneDipeptidyl peptidase 4Homo sapiens (human)
apical plasma membraneDipeptidyl peptidase 4Homo sapiens (human)
lamellipodiumDipeptidyl peptidase 4Homo sapiens (human)
endocytic vesicleDipeptidyl peptidase 4Homo sapiens (human)
lamellipodium membraneDipeptidyl peptidase 4Homo sapiens (human)
membrane raftDipeptidyl peptidase 4Homo sapiens (human)
intercellular canaliculusDipeptidyl peptidase 4Homo sapiens (human)
extracellular exosomeDipeptidyl peptidase 4Homo sapiens (human)
plasma membraneDipeptidyl peptidase 4Homo sapiens (human)
endoplasmic reticulumSterol O-acyltransferase 1Homo sapiens (human)
endoplasmic reticulum membraneSterol O-acyltransferase 1Homo sapiens (human)
membraneSterol O-acyltransferase 1Homo sapiens (human)
endoplasmic reticulum membraneSterol O-acyltransferase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID594820Inhibition of AChE-induced amyloid beta aggregation2011Bioorganic & medicinal chemistry letters, May-01, Volume: 21, Issue:9
(+)-Arisugacin A--computational evidence of a dual binding site covalent inhibitor of acetylcholinesterase.
AID398414Inhibition of electric eel AChE by Ellman's method1995Journal of natural products, Jun, Volume: 58, Issue:6
Acetylcholinesterase inhibition by territrem B derivatives.
AID31497Inhibitory activity against Acetylcholinesterase2000Bioorganic & medicinal chemistry letters, Jun-19, Volume: 10, Issue:12
Synthetic conversion of ACAT inhibitor to acetylcholinesterase inhibitor.
AID31814Inhibitory activity against acyl-CoA:cholesterol acyltransferase (ACAT)2000Bioorganic & medicinal chemistry letters, Jun-19, Volume: 10, Issue:12
Synthetic conversion of ACAT inhibitor to acetylcholinesterase inhibitor.
AID1254738Inhibition of human AChE2015Bioorganic & medicinal chemistry letters, Nov-01, Volume: 25, Issue:21
A computational view on the significance of E-ring in binding of (+)-arisugacin A to acetylcholinesterase.
AID1056366Inhibition of human acetylcholinesterase2013ACS medicinal chemistry letters, Nov-14, Volume: 4, Issue:11
Structures of human acetylcholinesterase bound to dihydrotanshinone I and territrem B show peripheral site flexibility.
AID398849Inhibition of electric eel AChE by Ellman's method1997Journal of natural products, Aug, Volume: 60, Issue:8
Structure and anti-acetylcholinesterase activity of 4 alpha-(hydroxymethyl)-4 alpha-demethylterritrem B.
AID1800423Assay of Substrate Hydrolysis from Article 10.1021/bi401043w: \\The natural product dihydrotanshinone I provides a prototype for uncharged inhibitors that bind specifically to the acetylcholinesterase peripheral site with nanomolar affinity.\\2013Biochemistry, Oct-22, Volume: 52, Issue:42
The natural product dihydrotanshinone I provides a prototype for uncharged inhibitors that bind specifically to the acetylcholinesterase peripheral site with nanomolar affinity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (24)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (16.67)18.7374
1990's7 (29.17)18.2507
2000's8 (33.33)29.6817
2010's5 (20.83)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: 18.99

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 Index18.99 (24.57)
Research Supply Index3.26 (2.92)
Research Growth Index4.62 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (18.99)

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]