Compounds > trilobolide
Page last updated: 2024-12-10

trilobolide

Description

trilobolide: structure in first source; RN given for (3S-(3alpha,3abeta,4alpha(R*),6beta,6abeta,8alpha(Z),9balpha))-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5281503
CHEMBL ID3343188
CHEBI ID9724
SCHEMBL ID1377153
MeSH IDM0228918

Synonyms (15)

Synonym
50657-07-3
C09563 ,
trilobolide
fiazivnrhqwtpy-qaapnfdwsa-
inchi=1/c27h38o10/c1-9-13(3)22(29)34-18-11-17-20(15(18)5)21-27(33,26(8,32)24(31)36-21)19(35-23(30)14(4)10-2)12-25(17,7)37-16(6)28/h9,14,17-19,21,32-33h,10-12h2,1-8h3/b13-9-/t14-,17-,18+,19-,21-,25-,26+,27+/m0/s1
[(3s,3ar,4s,6s,6as,8r,9bs)-6-acetyloxy-3,3a-dihydroxy-3,6,9-trimethyl-8-[(z)-2-methylbut-2-enoyl]oxy-2-oxo-4,5,6a,7,8,9b-hexahydroazuleno[4,5-b]furan-4-yl] (2s)-2-methylbutanoate
trilobolid
2-butenoic acid, 2-methyl-, 6-(acetyloxy)-2,3,3a,4,5,6,6a,7,8,9b-decahydro-3,3a-dihydroxy-3,6,9-trimethyl-4-(2-methyl-1-oxobutoxy)-2-oxoazuleno(4,5-b)furan-8-yl ester, (3s-(3alpha,3abeta,4alpha(r*),6beta,6abeta,8alpha(z),9balpha))-
silerin
SCHEMBL1377153
CHEBI:9724 ,
CHEMBL3343188
Q27108484
DTXSID001098581
(3s,3ar,4s,6s,6as,8r,9bs)-6-(acetyloxy)-2,3,3a,4,5,6,6a,7,8,9b-decahydro-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2s)-2-methyl-1-oxobutoxy]-2-oxoazuleno[4,5-b]furan-8-yl (2z)-2-methyl-2-butenoate

Research Excerpts

Overview

Trilobolide (Tb) is a potent natural counterpart of thapsigargin, which has shown promising results in cancer clinical trials.

ExcerptReferenceRelevance
"Trilobolide (Tb) is a potent natural counterpart of thapsigargin, which has shown promising results in cancer clinical trials. "( Tailor-made fluorescent trilobolide to study its biological relevance.
Drašar, P; Jurášek, M; Kmoníčková, E; Rimpelová, S; Ruml, T, 2014)		2.15
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
sesquiterpene lactoneAny member of a diverse class of complex, multicyclic phytochemicals showing a variety of skeleton arrangements and bioactivities, and having in common a sesquiterpenoid structure including a lactone 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 (30)

Assay IDTitleYearJournalArticle
AID1163000Cytotoxicity against human LNCAP cells after 48 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163002Cytotoxicity against human PC3 cells after 24 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163019Cytotoxicity against human HT-29 cells after 72 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1162990Cellular uptake in Endoplasmic reticulum of human U2OS cells at 1 uM after 1 hr by fluorescence microscopy2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163008Cytotoxicity against human U2OS cells after 24 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1162991Cellular uptake in Endoplasmic reticulum of human PC3 cells at 1 uM after 1 hr by fluorescence microscopy2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1162993Cellular uptake in Endoplasmic reticulum of human HeLa cells at 1 uM after 1 hr by fluorescence microscopy2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163018Cytotoxicity against human HT-29 cells after 48 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163004Cytotoxicity against human PC3 cells after 72 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163014Cytotoxicity against human MIAPaCa2 cells after 24 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163006Cytotoxicity against mouse C2C12 cells after 48 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163010Cytotoxicity against human U2OS cells after 72 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163001Cytotoxicity against human LNCAP cells after 72 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163016Cytotoxicity against human MIAPaCa2 cells after 72 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163021Cytotoxicity against rat peritoneal cells assessed as reduction in cell viability at 10 uM after 24 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163013Cytotoxicity against human MCF7 cells after 72 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163025Induction of LPS-induced NO production in human MCF7 cells at 40 uM after 24 hrs using DAR-2 probe by fluorescence assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163023Induction of LPS-induced NO production in human PC3 cells at 40 uM after 24 hrs using DAR-2 probe by fluorescence assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163024Induction of LPS-induced NO production in human LNCAP cells at 40 uM after 24 hrs using DAR-2 probe by fluorescence assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163003Cytotoxicity against human PC3 cells after 48 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163005Cytotoxicity against mouse C2C12 cells after 24 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163009Cytotoxicity against human U2OS cells after 48 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1162992Cellular uptake in Endoplasmic reticulum of human LNCAP cells at 1 uM after 1 hr by fluorescence microscopy2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163017Cytotoxicity against human HT-29 cells after 24 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1162999Cytotoxicity against human LNCAP cells after 24 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163007Cytotoxicity against mouse C2C12 cells after 72 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163012Cytotoxicity against human MCF7 cells after 48 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163015Cytotoxicity against human MIAPaCa2 cells after 48 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163011Cytotoxicity against human MCF7 cells after 24 hrs by WST-1 assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
AID1163026Induction of LPS-induced NO production in human U2OS cells at 40 uM after 24 hrs using DAR-2 probe by fluorescence assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Tailor-made fluorescent trilobolide to study its biological relevance.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (15.38)18.2507
2000's1 (7.69)29.6817
2010's8 (61.54)24.3611
2020's2 (15.38)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.46

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 Index12.46 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index5.10 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.46)

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%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
egtazic acid
Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.		2.0510diether;
tertiary amino compound;
tetracarboxylic acid		chelator
carvone
carvone: an oxidized derivative of limonene; RN given refers to cpd without isomeric designation; L-carvone has spearmint flavor, D-carvone has dill/caraway flavor. carvone : A p-menthane monoterpenoid that consists of cyclohex-2-enone having methyl and isopropenyl substituents at positions 2 and 5, respectively.		7.0110botanical anti-fungal agent;
carvones		allergen
2,5-di-tert-butylbenzoquinone
[no description available]		1.9810benzoquinones;
p-quinones
hydroxyl radical
Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.		1.9810oxygen hydride;
oxygen radical;
reactive oxygen species
thapsigargin
Thapsigargin: A sesquiterpene lactone found in roots of THAPSIA. It inhibits SARCOPLASMIC RETICULUM CALCIUM-TRANSPORTING ATPASES.. thapsigargin : An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations.		2.4420butyrate ester;
organic heterotricyclic compound;
sesquiterpene lactone		calcium channel blocker;
EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
sesquiterpenes
[no description available]		2.9540
1,2-bis(2-aminophenoxy)ethane n,n,n',n'-tetraacetic acid acetoxymethyl ester
[no description available]		2.0510
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
[no description available]		2.110BODIPY compound
ConditionIndicatedRelationship StrengthStudiesTrials
Benign Neoplasms
[description not available]		02.2510
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.2510
Carcinogenesis
The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.		02.3110
Hepatocellular Carcinoma
[description not available]		07.3110
Cancer of Liver
[description not available]		02.3110
Carcinoma, Hepatocellular
A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.		02.3110
Liver Neoplasms
Tumors or cancer of the LIVER.		02.3110
chemdatabank.com