Compounds > Tonantzitlolone A
Page last updated: 2024-11-13

Tonantzitlolone A

Cross-References

ID SourceID
PubMed CID25053359
CHEMBL ID3581994
CHEBI ID182283

Synonyms (4)

Synonym
CHEBI:182283
tonantzitlolone a
[(1r,2s,3r,6s,8e,10s,12r,14r,15r)-1,2-dihydroxy-3,7,7,10,14-pentamethyl-11-oxo-16,17-dioxatricyclo[10.3.1.13,6]heptadec-8-en-15-yl] (e)-3-methylpent-2-enoate
CHEMBL3581994

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"Synthesis of analogues of englerin A with a reduced propensity for hydrolysis of the glycolate moiety led to a compound which possessed the renal cancer cell selectivity of the parent and was orally bioavailable in mice."( Synthesis of a stable and orally bioavailable englerin analogue.
Beutler, JA; Chain, WJ; Fash, DM; Figg, WD; Hayavi, S; Li, Z; Neckers, L; Peer, CJ; Ramos, JW; Sourbier, C; Sulzmaier, FJ; Talisman, IJ, 2016)		0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
fatty acid esterA carboxylic ester in which the carboxylic acid component can be any fatty acid.
[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 (37)

Assay IDTitleYearJournalArticle
AID1284142Inhibition of Xenopus laevis kinesin-5 assessed as velocity at 150 uM incubated for 7 mins measured for 600 secs by single molecule TIRF microscopy (Rvb = 17.2 +/- 8.3 nm/s)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1228728Antiviral activity against Sindbis virus strain HRsp infected in african green monkey Vero cells assessed as inhibition of virus induced cell death measured after 7 days2015Journal of natural products, May-22, Volume: 78, Issue:5
Antiviral Activity of Flexibilane and Tigliane Diterpenoids from Stillingia lineata.
AID1284138Inhibition of Xenopus laevis kinesin-5 assessed as attachment to microtubules incubated for 7 mins measured for 600 secs by single molecule TIRF microscopy2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1284135Cytotoxicity against mouse L929 cells after 5 days by MTT assay2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1284163Inhibition of eGFP-tagged rat kinesin-1 assessed as velocity at 300 uM incubated for 7 mins measured for 60 secs by single molecule TIRF microscopy (Rvb = 535.7 +/- 35.7 nm/s)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1540945Cytotoxicity against African green monkey Vero cells assessed as reduction in cell viability measured after 1 hr by MTT assay
AID1284152Inhibition of Xenopus laevis kinesin-5 assessed as motile protein molecules at 300 uM incubated for 7 mins measured for 600 secs by single molecule TIRF microscopy (Rvb = 42.81 +/- 0.25%)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1284144Inhibition of Xenopus laevis kinesin-5 assessed as velocity at 600 uM incubated for 7 mins measured for 600 secs by single molecule TIRF microscopy (Rvb = 17.2 +/- 8.3 nm/s)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1228730Cytotoxicity against african green monkey Vero cells assessed as inhibition of cell metabolism after 72 hrs by MTS assay2015Journal of natural products, May-22, Volume: 78, Issue:5
Antiviral Activity of Flexibilane and Tigliane Diterpenoids from Stillingia lineata.
AID1284151Inhibition of Xenopus laevis kinesin-5 assessed as motile protein molecules at 150 uM incubated for 7 mins measured for 600 secs by single molecule TIRF microscopy (Rvb = 42.81 +/- 0.25%)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1228739Cytotoxicity against human HCT116 cells at 1 uM after 72 hrs by MTS assay2015Journal of natural products, May-22, Volume: 78, Issue:5
Antiviral Activity of Flexibilane and Tigliane Diterpenoids from Stillingia lineata.
AID1228727Antiviral activity against Chikungunya virus strain 899 infected in african green monkey Vero cells assessed as inhibition of virus induced cell death measured after 7 days2015Journal of natural products, May-22, Volume: 78, Issue:5
Antiviral Activity of Flexibilane and Tigliane Diterpenoids from Stillingia lineata.
AID1284150Inhibition of Xenopus laevis kinesin-5 assessed as relative number of MT-bound proteins at 600 uM incubated for 7 mins measured for 600 secs by single molecule TIRF microscopy (Rvb = 100 +/- 0.9%)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1284170Inhibition of eGFP-tagged rat kinesin-1 assessed as relative number of MT-bound proteins at 600 uM incubated for 7 mins measured for 60 secs by single molecule TIRF microscopy (Rvb = 100 +/- 1.8%)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1284164Inhibition of eGFP-tagged rat kinesin-1 assessed as velocity at 600 uM incubated for 7 mins measured for 60 secs by single molecule TIRF microscopy (Rvb = 535.7 +/- 35.7 nm/s)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1484124Antiproliferative activity against human A498 cells after 48 hrs by MTT assay2017Journal of natural products, 03-24, Volume: 80, Issue:3
Englerins: A Comprehensive Review.
AID1284139Inhibition of Xenopus laevis kinesin-5 assessed as decrease in protein molecules per micrometer microtubule length for 7 mins measured for 600 secs by single molecule TIRF microscopy2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1284134Antiproliferative activity against human U937 cells after 5 days by MTT assay2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1301140Activation of PKC in human 786-0 cells at 1 uM2016Bioorganic & medicinal chemistry letters, 06-01, Volume: 26, Issue:11
Synthesis of a stable and orally bioavailable englerin analogue.
AID1284169Inhibition of eGFP-tagged rat kinesin-1 assessed as relative number of MT-bound proteins at 300 uM incubated for 7 mins measured for 60 secs by single molecule TIRF microscopy (Rvb = 100 +/- 1.8%)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1284148Inhibition of Xenopus laevis kinesin-5 assessed as relative number of MT-bound proteins at 150 uM incubated for 7 mins measured for 600 secs by single molecule TIRF microscopy (Rvb = 100 +/- 0.9%)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1284167Inhibition of eGFP-tagged rat kinesin-1 assessed as attachment frequency at 300 uM incubated for 7 mins measured for 60 secs by single molecule TIRF microscopy (Rvb = 7.72 +/- 0.31 /microM/micrometer/sec)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1284166Inhibition of eGFP-tagged rat kinesin-1 assessed as attachment frequency at 600 uM incubated for 7 mins measured for 60 secs by single molecule TIRF microscopy (Rvb = 7.72 +/- 0.31 /microM/micrometer/sec)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1228740Cytotoxicity against human MCF7 cells at 1 uM after 72 hrs by MTS assay2015Journal of natural products, May-22, Volume: 78, Issue:5
Antiviral Activity of Flexibilane and Tigliane Diterpenoids from Stillingia lineata.
AID1228729Antiviral activity against Semliki forest virus strain Vietnam infected in african green monkey Vero cells assessed as inhibition of virus induced cell death measured after 7 days2015Journal of natural products, May-22, Volume: 78, Issue:5
Antiviral Activity of Flexibilane and Tigliane Diterpenoids from Stillingia lineata.
AID1284174Cytotoxicity against Potorous tridactylus PtK2 cells assessed as effect on phenotype of interphase cell at 21.5 uM after 18 hrs by DAPI staining-based fluorescence microscopy2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1284147Inhibition of Xenopus laevis kinesin-5 assessed as attachment frequency at 600 uM incubated for 7 mins measured for 600 secs by single molecule TIRF microscopy (Rvb = 1.08 +/- 0.10 /microM/micrometer/sec)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1284143Inhibition of Xenopus laevis kinesin-5 assessed as velocity at 300 uM incubated for 7 mins measured for 600 secs by single molecule TIRF microscopy (Rvb = 17.2 +/- 8.3 nm/s)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1228741Cytotoxicity against human PC3 cells at 1 uM after 72 hrs by MTS assay2015Journal of natural products, May-22, Volume: 78, Issue:5
Antiviral Activity of Flexibilane and Tigliane Diterpenoids from Stillingia lineata.
AID1284173Inhibition of eGFP-tagged rat kinesin-1 assessed as motile protein molecules at 600 uM incubated for 7 mins measured for 60 secs by single molecule TIRF microscopy (Rvb = 88.74 +/- 0.34%)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1284172Inhibition of eGFP-tagged rat kinesin-1 assessed as motile protein molecules at 300 uM incubated for 7 mins measured for 60 secs by single molecule TIRF microscopy (Rvb = 88.74 +/- 0.34%)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1284149Inhibition of Xenopus laevis kinesin-5 assessed as relative number of MT-bound proteins at 300 uM incubated for 7 mins measured for 600 secs by single molecule TIRF microscopy (Rvb = 100 +/- 0.9%)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1284136Cytotoxicity against Potorous tridactylus PtK2 cells after 5 days by MTT assay2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1284153Inhibition of Xenopus laevis kinesin-5 assessed as motile protein molecules at 600 uM incubated for 7 mins measured for 600 secs by single molecule TIRF microscopy (Rvb = 42.81 +/- 0.25%)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1284137Cell cycle arrest in Potorous tridactylus PtK2 cells assessed as unphysiological monoastral half spindle formation at 21.5 uM after 18 hrs by DAPI staining-based fluorescence microscopy2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1284146Inhibition of Xenopus laevis kinesin-5 assessed as attachment frequency at 300 uM incubated for 7 mins measured for 600 secs by single molecule TIRF microscopy (Rvb = 1.08 +/- 0.10 /microM/micrometer/sec)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
AID1284145Inhibition of Xenopus laevis kinesin-5 assessed as attachment frequency at 150 uM incubated for 7 mins measured for 600 secs by single molecule TIRF microscopy (Rvb = 1.08 +/- 0.10 /microM/micrometer/sec)2016European journal of medicinal chemistry, Apr-13, Volume: 112The natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell proliferation and kinesin-5 function.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's5 (100.00)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: 12.72

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 Index12.72 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.72)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (20.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
chloroquine
Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.		2.1110aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug
nevirapine
Nevirapine: A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV INFECTIONS and AIDS.. nevirapine : A dipyridodiazepine that is 5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine which is substituted by methyl, oxo, and cyclopropyl groups at positions 4, 6, and 11, respectively. A non-nucleoside reverse transcriptase inhibitor with activity against HIV-1, it is used in combination with other antiretrovirals for the treatment of HIV infection.		2.1110cyclopropanes;
dipyridodiazepine		antiviral drug;
HIV-1 reverse transcriptase inhibitor
zidovudine
Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.		2.1110azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
lamivudine
[no description available]		2.1110monothioacetal;
nucleoside analogue;
oxacycle;
primary alcohol		allergen;
anti-HBV agent;
antiviral drug;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor;
HIV-1 reverse transcriptase inhibitor;
prodrug
monastrol
monastrol: stops mitosis by fostering formation of monopolar spindles; structure in first source. (S)-monastrol : An ethyl 4-(3-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate that has S configuration.. monastrol : A racemate comprising equimolar amounts of R- and S-monastrol.. ethyl 4-(3-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate : A member of the class of thioureas that is 3,4-dihydropyrimidine-2(1)-thione substituted by a 3-hydroxyphenyl group at position 4, an ethoxycarbonyl group at position 5, and a methyl group at position 6.		2.1310enoate ester;
ethyl ester;
phenols;
racemate;
thioureas		antileishmanial agent;
antimitotic;
antineoplastic agent;
EC 3.5.1.5 (urease) inhibitor
englerin a
[no description available]		3.6420cinnamate ester;
glycolate ester;
guaiane sesquiterpenoid		antineoplastic agent;
metabolite
didanosine
Didanosine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite.. didanosine : A purine 2',3'-dideoxyribonucleoside that is inosine in which the hydroxy groups at both the 2' and the 3' positions on the sugar moiety have been replaced by hydrogen. An antiviral drug, it is used as a medication to treat HIV/AIDS.		2.1110purine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor;
geroprotector;
HIV-1 reverse transcriptase inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Cancer of Kidney
[description not available]		03.0610
Kidney Neoplasms
Tumors or cancers of the KIDNEY.		03.0610
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