Compounds > toosendanin
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toosendanin

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Toosendanin is a natural limonoid compound isolated from the seeds of the Chinese medicinal plant Melia toosendan. It exhibits a range of biological activities, including insecticidal, antifungal, and anti-inflammatory properties. The compound's complex structure has attracted significant interest from synthetic chemists, and several synthetic routes have been developed. Toosendanin's potential as a biopesticide and its unique biological activities make it a subject of ongoing research. Its insecticidal activity has led to studies exploring its potential for controlling agricultural pests. Toosendanin's diverse biological properties and structural complexity make it a valuable target for further investigation, potentially leading to the development of new pharmaceuticals or agricultural applications.'

FloraRankFlora DefinitionFamilyFamily Definition
MeliagenusA plant genus of the family MELIACEAE. Members contain meliavolkinin, melianin C and limonoids.[MeSH]MeliaceaeThe mahogany plant family of the order Sapindales, subclass Rosidae, class Magnoliopsida.[MeSH]

Cross-References

ID SourceID
PubMed CID9851101
CHEMBL ID503044
CHEBI ID192461
PubMed CID115060
SCHEMBL ID20638526
MeSH IDM0111040

Synonyms (26)

Synonym
CHEMBL503044
[(1s,2r,4r,5r,6s,8r,10s,11s,12r,14r,15r,16r,19s,21r)-4-acetyloxy-6-(uran-3-yl)-12,16,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-21-yl] acetate
CHEBI:192461
AKOS025311566
12-acetoxyamoorastatin
Q-100679
mfcd00210564
[(1s,2r,4r,5r,6s,8r,10s,11s,12r,14r,15r,16r,19s,21r)-4-acetyloxy-6-(furan-3-yl)-12,16,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-21-yl] acetate
HY-N0263
CS-0008285
AS-56295
brn 1674886
toosendanin ,
chuanliansu
24-norchola-20,22-diene-4-carboxaldehyde, 3,12-bis(acetyloxy)-14,15:21,23-diepoxy-1,7,19-trihydroxy-4,8-dimethyl-11-oxo-, cyclic 4,19-hemiacetal, (1-alpha,3-alpha,4-beta(r), 5-alpha,7-alpha,12-alpha,13-alpha,14-beta,15-beta,17-alpha)-
58812-37-6
S9305
AKOS015897147
[(1s,2r,4r,5r,6s,8r,10s,11s,12r,14r,16r,19s,21r)-4-acetyloxy-6-(furan-3-yl)-12,16,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-21-yl] acetate
HMS3887I11
DTXSID00974333
9-(furan-3-yl)-1,6,14-trihydroxy-4,6a,9a-trimethyl-11-oxotetradecahydro-1h-4,11b-(methanooxymethano)naphtho[1',2':6,7]indeno[1,7a-b]oxirene-3,10-diyl diacetate
CCG-270108
toosendanin; chuanliansu; 12-acetoxyamoorastatin
SCHEMBL20638526
NCGC00482963-01

Research Excerpts

Overview

Toosendanin (TSN) is a natural anti-cancer compound that is isolated from the traditional Chinese herbal Melia toos endan Sieb et Zucc. Toos Endanin is a commercial insecticidal active ingredient used to manage various pests in the field and showed adverse effects against S. coli.

ExcerptReferenceRelevance
"Toosendanin (TSN) is a natural anti-cancer compound that is isolated from the traditional Chinese herbal Melia toosendan Sieb et Zucc. "( Design, synthesis, and anti-triple negative breast cancer activity of novel Toosendanin derivatives.
Chen, CH; Chen, Y; Li, D; Liu, Q; Pan, ZH; Shao, LD; Xiao, WW; Zhang, H, 2023)		2.58
"Toosendanin (TSN) is an active compound from the fruit of Melia toosendan Sieb et Zucc. "( Toosendanin-induced apoptosis of CMT-U27 is mediated through the mitochondrial apoptotic pathway.
Li, J; Liang, ZX; Ma, Y; Mei, C; Wang, HJ; Xian, H; Yang, Y; Zhang, X; Zhi, Y, 2023)		3.8
"Toosendanin (TSN) is a commercial insecticidal active ingredient used to manage various pests in the field and showed adverse effects against S."( Characterization of the physiological, histopathological, and gene expression alterations in Spodoptera frugiperda larval midguts affected by toosendanin exposure.
Cai, X; Huang, Y; Lin, J; Lin, Y; Liu, J; Liu, L; Shu, B, 2023)		1.83
"Toosendanin (TSN) is a botanical compound with broad-spectrum insecticidal activities against many pests."( Characterization and transcriptomic analyses of the toxicity induced by toosendanin in Spodoptera frugipreda.
Cai, X; Huang, Y; Lin, J; Lin, Y; Liu, L; Shu, B; Zhang, J, 2024)		2.4
"Toosendanin (TSN) is a tetracyclic triterpenoid extracted from Melia toosendan Sieb, et Zucc, which primarily grows in specific areas of China. "( Toosendanin induces apoptosis of MKN‑45 human gastric cancer cells partly through miR‑23a‑3p‑mediated downregulation of BCL2.
Feng, Y; Li, S; Liu, C; Pan, Y; Shao, S; Zhang, W; Zhang, Z; Zhu, S, 2020)		3.44
"Toosendanin is a phytochemical found in the medicinal plant Melia toosendan Sieb."( Characterization of a 2,3-oxidosqualene cyclase in the toosendanin biosynthetic pathway of Melia toosendan.
Lian, X; Qi, X; Wang, F; Wang, X; Xue, Z; Zhang, X, 2020)		1.53
"Toosendanin (TSN) is a crucial component from Toosendan Fructus with a promising anti-tumor capacity. "( Toosendanin triggered hepatotoxicity in zebrafish via inflammation, autophagy, and apoptosis pathways.
Gao, S; Liang, Q; Liu, K; Liu, Q; She, G; Sun, M; Xia, Q; Zhang, H; Zhang, Y; Zhuang, K, 2021)		3.51
"Toosendanin (TSN) is a triterpenoid purified from the medicinal herb Melia toosendan Sieb. "( Anti-cancer effect of toosendanin and its underlying mechanisms.
Cao, L; Li, Z; Ma, J; Wang, ZR; Zhang, S, 2019)		2.27
"Toosendanin (TSN) is a hepatotoxic triterpenoid extracted from Melia toosendan Sieb et Zucc. "( Identification of amino acid and glutathione N-conjugates of toosendanin: bioactivation of the furan ring mediated by CYP3A4.
Chen, X; Deng, P; Yu, J; Zhong, D, 2014)		2.09
"Toosendanin (TSN) is a triterpenoid extracted from the bark or fruits of Melia toosendan Sieb et Zucc and possesses antitumour effects on various human cancer cells."( Toosendanin inhibits growth and induces apoptosis in colorectal cancer cells through suppression of AKT/GSK-3β/β-catenin pathway.
Chu, SJ; Feng, CC; Lu, YM; Wang, G; Zhang, J; Zhang, R; Zhu, JS, 2015)		2.58
"Toosendanin (TSN) is a major triterpenoid existing in Melia toosendan, which has been used as a digestive tract parasiticide and insecticide but with serious hepatotoxicity. "( Determination of toosendanin in rat plasma by ultra-performance liquid chromatography-electrospray ionization-mass spectrometry and its application in a pharmacokinetic study.
Wang, C; Wang, X; Wang, Z, 2013)		2.17
"Toosendanin is a pre-synaptic blocker at the neuromuscular junction and its inhibitory effect is divided into an initial facilitative/stimulatory phase followed by a prolonged inhibitory phase. "( The pre-synaptic blocker toosendanin does not inhibit secretion in exocrine cells.
Cui, ZJ; He, XH, 2002)		2.06
"Toosendanin is a triterpenoid derivative extracted from a digestive tract-parasiticide in Chinese traditional medicine."( Cure of experimental botulism and antibotulismic effect of toosendanin.
Shi, YL; Wang, ZF, 2004)		1.29
"Toosendanin is a triterpenoid derivative extracted from Melia toosendan Sieb et Zucc. "( The long-term effect of toosendanin on current through nifedipine-sensitive Ca2+ channels in NG108-15 cells.
Li, MF; Shi, YL, 2005)		2.08
"Toosendanin (TSN) is a triterpenoid derivative found in Melia toosendan Sieb. "( Qualitative and quantitative analysis of toosendanin in Melia toosendan Sieb. Et Zucc (Meliaceae) with liquid chromatography/tandem mass spectrometry.
Ong, CN; Ong, ES, 2007)		2.05
"Toosendanin (TSN) is a triterpenoid extracted from Melia toosendan Sieb et Zucc, which was used as a digestive tract-parasiticide and agricultural insecticide in ancient China. "( Biological effects of toosendanin, a triterpenoid extracted from Chinese traditional medicine.
Li, MF; Shi, YL, 2007)		2.1

Effects

Toosendanin (TSN) has shown therapeutic effects on NSCLC; however, the role of TSN on CDDP sensitization inNSCLC remains unknown. TSN has an unprecedented dual mode of action on the protein-conducting channel acting as a cargo-dependent inhibitor of translocation.

ExcerptReferenceRelevance
"Toosendanin has an unprecedented dual mode of action on the protein-conducting channel acting as a cargo-dependent inhibitor of translocation and as cargo-free channel activator."( Bimodal modulation of the botulinum neurotoxin protein-conducting channel.
Clancy, CM; Dickerson, TJ; Eubanks, LM; Fischer, A; Janda, KD; Johnson, EA; Montal, M; Nakai, Y; Pellett, S; Tepp, WH, 2009)		1.07
"Toosendanin (TSN) has exhibited antitumor effects on various human cancer cells, but its influence on GC is largely unidentified."( Toosendanin suppresses oncogenic phenotypes of human gastric carcinoma SGC‑7901 cells partly via miR‑200a‑mediated downregulation of β-catenin pathway.
Chen, XY; Hou, LD; Huang, YX; Liu, H; Wang, G; Zhang, J; Zhang, R; Zhu, JS, 2017)		2.62
"Toosendanin (TSN) has shown therapeutic effects on NSCLC; however, the role of TSN on CDDP sensitization in NSCLC remains unknown."( Toosendanin mediates cisplatin sensitization through targeting Annexin A4/ATP7A in non-small cell lung cancer cells.
Li, XL; Tang, JH; Wang, ND; Yan, J; Zhang, Z; Zhao, XH; Zheng, MD, 2018)		2.64
"Toosendanin extract has potent anti-cancer effects via suppressing proliferation and inducing apoptosis of cancer cells in vivo and in vitro. "( Anticancer effects of crude extract from Melia toosendan Sieb. et Zucc on hepatocellular carcinoma in vitro and in vivo.
He, X; He, YJ; Liu, XL; Wang, H; Wang, J; Wang, P; Wang, YL; Zhang, L, 2016)		1.88
"Toosendanin has an unprecedented dual mode of action on the protein-conducting channel acting as a cargo-dependent inhibitor of translocation and as cargo-free channel activator."( Bimodal modulation of the botulinum neurotoxin protein-conducting channel.
Clancy, CM; Dickerson, TJ; Eubanks, LM; Fischer, A; Janda, KD; Johnson, EA; Montal, M; Nakai, Y; Pellett, S; Tepp, WH, 2009)		1.07
"Toosendanin has no effect on intracellular calcium or secretion in the non-excitable pancreatic acinar cells, ruling out general toosendanin inhibition of exocytosis."( The anti-botulism triterpenoid toosendanin elicits calcium increase and exocytosis in rat sensory neurons.
Cui, ZJ; Fang, XF, 2011)		1.38

Actions

Toosendanin could inhibit the proliferation and induce the apoptosis of both P53 and P53 human hepatocarcinoma cells. It did not inhibit the fusion process between autophagosome and lysosome.

ExcerptReferenceRelevance
"Toosendanin did not inhibit the fusion process between autophagosome and lysosome but elevated lysosomal pH and impaired lysosomal enzymes activity."( Toosendanin, a novel potent vacuolar-type H
Chen, QL; Chen, XP; Dong, Y; Fu, J; Keon, KA; Li, M; Lu, JH; Lu, JJ; Rubinstein, JL; Shen, HM; Wang, SF; Zeng, SX; Zhang, S; Zhu, G, 2022)		2.89
"Toosendanin could inhibit the proliferation and induce the apoptosis of both P53 and P53 human hepatocarcinoma cells, which involved the participation of mitochondria-dependent pathway. "( [Human hepatocarcinoma cell apoptosis induced by toosendanin through mitochondria-dependent pathway].
Jiang, H; Wang, J; Wang, P, 2011)		2.07

Toxicity

ExcerptReferenceRelevance
"Drug-induced liver injury is a clinically leading side-effect of drugs."( Optimization of extraction and analytical protocol for mass spectrometry-based metabolomics analysis of hepatotoxicity.
Hu, DD; Li, F; Xiao, XR; Yang, R; Zhao, Q, 2018)		0.48

Pharmacokinetics

The method was successfully applied to a pharmacokinetic study of toosendanin after its oral administration in rats at a dose of 10 mg/kg.

ExcerptReferenceRelevance
" The method was successfully applied to a pharmacokinetic study of TSN in rats after a single intravenous and oral administration of 2 and 60 mg/kg."( Determination of toosendanin in rat plasma by ultra-performance liquid chromatography-electrospray ionization-mass spectrometry and its application in a pharmacokinetic study.
Wang, C; Wang, X; Wang, Z, 2013)		0.73
" This analytical method was successfully applied to determine the pharmacokinetic parameters of isotoosendanin after an oral administration of 200 mg/kg to rats."( Determination of isotoosendanin in rat plasma by liquid chromatography-tandem mass spectrometry: application to pharmacokinetics study.
Cui, S; Deng, Z; Liu, S; Xie, Y; Yao, Q; Zhong, H, 2013)		0.93
" The method was successfully applied to a pharmacokinetic study of toosendanin after its oral administration in rats at a dose of 10 mg/kg."( A Sensitive Liquid Chromatography-Mass Spectrometry Method for Determination of Toosendanin in Rat Plasma and its Application to Pharmacokinetic Study.
Deng, Z; Guo, J; Li, Q; Liu, C; Liu, M; Pan, Z; Shen, C; Si, Y; Tu, H; Wu, X; Xin, X; Zhong, C; Zhu, Z, 2022)		1.18

Bioavailability

ExcerptReferenceRelevance
" Its bioavailability in rats is low, which indicates the hepatotoxicity might be induced by its metabolites."( Metabolite analysis of toosendanin by an ultra-high performance liquid chromatography-quadrupole-time of flight mass spectrometry technique.
Leung, EL; Li, N; Liu, L; Wu, JL; Zhou, H, 2013)		0.7
"The pharmacokinetic results indicate that XHX can significantly decrease the absorption and bioavailability and accelerate the elimination process of toosendanin in CLZ."( Determination of toosendanin and trans-anethole in Fructus Meliae Toosendan and Fructus Foeniculi by HPLC-MS/MS and GC-MS/MS in rat plasma and their potential herb-herb interactions.
Liu, L; Shi, L; Wang, Q; Xu, Y; Yu, J; Zhang, R; Zhang, T; Zhang, Y; Zhao, J, 2020)		1.1

Dosage Studied

ExcerptRelevanceReference
" Application of frequent, low doses of celangulin/toosendanin (1:9) mixture also reduced the dosage of biocides, thereby reducing the cost of exterminating rotifers, and indicating a considerable practical application in microalgal cultivation."( Efficacy of binary combinations of botanical pesticides for rotifer elimination in microalgal cultivation.
Huang, Y; Li, L; Liu, J; Pang, T; Zhang, L, 2014)		0.66
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
limonoidAny triterpenoid that is highly oxygenated and has a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. The term 'limonoid' comes from limonin, the first tetranortriterpenoid obtained from citrus bitter principles.
[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 (79)

Assay IDTitleYearJournalArticle
AID1100882Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean time to pupation at 52 ug/ml in artificial diet (Rvb = 22 days)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1082998Insecticidal activity against pre-third-instar larvae of Mythimna separata (Oriental armyworm) in wheat leaves at 1 mg/mL after 5 days by leaf-dipping method2012Journal of agricultural and food chemistry, Aug-29, Volume: 60, Issue:34
Synthesis and quantitative structure-activity relationship (QSAR) study of novel isoxazoline and oxime derivatives of podophyllotoxin as insecticidal agents.
AID1101943Antifeedant activity against larvae of Epilachna paenulata in Cucurbita maxima leaves at 10 ug/cm2 after 24 hr by leaf disc choice test2002Bioscience, biotechnology, and biochemistry, Aug, Volume: 66, Issue:8
Potent limonoid insect antifeedant from Melia azedarach.
AID1100875Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean pupation at 52 ug/ml in artificial diet (Rvb = 87.5 %)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1112940Insecticidal activity against pre-third-instar larvae of Mythimna separata (Oriental armyworm) assessed as corrected mortality rate at 1 mg/ml measured after 20 days by the leaf-dipping method2013Journal of agricultural and food chemistry, Jan-23, Volume: 61, Issue:3
Synthesis and quantitative structure-activity relationship (QSAR) study of novel 4-acyloxypodophyllotoxin derivatives modified in the A and C rings as insecticidal agents.
AID1105325Antifeedant activity against Tribolium castaneum (red flour beetle) assessed as reduction of food consumption after 3 days by flour disk bioassay relative to control2011Molecules (Basel, Switzerland), Jul-20, Volume: 16, Issue:7
Antifeedant diterpenoids against Tribolium castaneum from the stems and twigs of Ceriops tagal (Rhizophoraceae).
AID1082014Feeding deterrent activity against Tribolium castaneum (red flour beetle) adults using wheat flour assessed as inhibition of insect feeding measured after 3 days2011Journal of agricultural and food chemistry, Apr-27, Volume: 59, Issue:8
Feeding deterrents from Aconitum episcopale roots against the red flour beetle, Tribolium castaneum.
AID1080794In vivo insecticidal activity against pre-third-instar larval stage of Mythimna separata (Oriental armyworm) in corn leaves assessed as corrected mortality rate at 1 mg/ml treated for 3 secs before larval infestation measured after 36 days by leaf-dipping2009Journal of agricultural and food chemistry, Sep-09, Volume: 57, Issue:17
Semisynthesis and quantitative structure-activity relationship (QSAR) study of novel aromatic esters of 4'-demethyl-4-deoxypodophyllotoxin as insecticidal agents.
AID1101936Antifeedant activity against larvae of Spodoptera eridania in Cucurbita maxima leaves at 4 ug/cm2 after 24 hr by leaf disk choice test2002Bioscience, biotechnology, and biochemistry, Aug, Volume: 66, Issue:8
Potent limonoid insect antifeedant from Melia azedarach.
AID1100889Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean length at 5 ug/ml in artificial diet measured after 7 days (Rvb = 28 +/- 4.1 mg)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1092158Insecticidal activity against pre-third-instar larvae of Mythimna separata (Oriental armyworm) in compound treated fresh corn leaves assessed as corrected mortality at 1 mg/ml measured after 10 days by leaf-dipping method2012Bioorganic & medicinal chemistry letters, Sep-01, Volume: 22, Issue:17
Regioselective synthesis of fraxinellone-based hydrazone derivatives as insecticidal agents.
AID1100896Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean weight gain at 25 ug/ml in artificial diet measured after 7 days (Rvb = 469.5 +/- 6.59 mg)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1100879Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean emergence at 5 ug/ml in artificial diet (Rvb = 83.3 %)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID590132Insecticidal activity against Mythimna separata Walker assessed as mortality rate at 1 mg/mL after 35 days by leaf dipping method2011Bioorganic & medicinal chemistry letters, Apr-01, Volume: 21, Issue:7
Natural products-based insecticidal agents 9. Design, semisynthesis and insecticidal activity of 28-acyloxy derivatives of toosendanin against Mythimna separata Walker in vivo.
AID590130Insecticidal activity against Mythimna separata Walker assessed as mortality rate at 1 mg/mL after 10 days by leaf dipping method2011Bioorganic & medicinal chemistry letters, Apr-01, Volume: 21, Issue:7
Natural products-based insecticidal agents 9. Design, semisynthesis and insecticidal activity of 28-acyloxy derivatives of toosendanin against Mythimna separata Walker in vivo.
AID1100901Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mortality at 52 ug/ml in artificial diet measured after 7 days (Rvb = 8.33%)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1080795In vivo insecticidal activity against pre-third-instar larval stage of Mythimna separata (Oriental armyworm) in corn leaves assessed as corrected mortality rate at 1 mg/ml treated for 3 secs before larval infestation measured after 24 days by leaf-dipping2009Journal of agricultural and food chemistry, Sep-09, Volume: 57, Issue:17
Semisynthesis and quantitative structure-activity relationship (QSAR) study of novel aromatic esters of 4'-demethyl-4-deoxypodophyllotoxin as insecticidal agents.
AID1101938Antifeedant activity against larvae of Spodoptera eridania in Cucurbita maxima leaves at 14 ug/cm2 after 24 hr by leaf disk choice test2002Bioscience, biotechnology, and biochemistry, Aug, Volume: 66, Issue:8
Potent limonoid insect antifeedant from Melia azedarach.
AID1082882Insecticidal activity against Mythimna separata (Oriental armyworm) in wheat leaves assessed as mortality rate at 1 mg/mL at 25 degC measured after 10 days by leaf-dipping method relative to control2012Journal of agricultural and food chemistry, Jul-18, Volume: 60, Issue:28
Synthesis and insecticidal activity of some novel fraxinellone-based esters.
AID1101941Antifeedant activity against larvae of Epilachna paenulata in Cucurbita maxima leaves at 4 ug/cm2 after 24 hr by leaf disc choice test2002Bioscience, biotechnology, and biochemistry, Aug, Volume: 66, Issue:8
Potent limonoid insect antifeedant from Melia azedarach.
AID1100884Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean weight of pupae at 25 ug/ml in artificial diet (Rvb = 281.5 +/- 10.3 mg)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID460808Inhibition of Clostridium botulinum strain Hall A hyper botulinum neurotoxin type A1 in rat spinal cord cells assessed as intact SNAP25 protein level at 200 uM after 24 hrs by Western blot using monoclonal anti-SNAP25 antibody2010Bioorganic & medicinal chemistry, Feb, Volume: 18, Issue:3
Toosendanin: synthesis of the AB-ring and investigations of its anti-botulinum properties (Part II).
AID590131Insecticidal activity against Mythimna separata Walker assessed as mortality rate at 1 mg/mL after 20 days by leaf dipping method2011Bioorganic & medicinal chemistry letters, Apr-01, Volume: 21, Issue:7
Natural products-based insecticidal agents 9. Design, semisynthesis and insecticidal activity of 28-acyloxy derivatives of toosendanin against Mythimna separata Walker in vivo.
AID1091880In vivo insecticidal activity against pre-third-instar larval stage of Mythimna separata (Oriental armyworm) in corn leaves assessed as corrected mortality rate at 1 mg/ml treated for 3 secs before larval infestation on corn leaves measured after 20 days 2010Bioorganic & medicinal chemistry letters, Apr-15, Volume: 20, Issue:8
Natural products-based insecticidal agents 5. Design, semisynthesis and insecticidal activity of novel 4'-substituted benzenesulfonate derivatives of 4-deoxypodophyllotoxin against Mythimna separata Walker in vivo.
AID1100881Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean time to pupation at 25 ug/ml in artificial diet (Rvb = 22 days)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1112941Insecticidal activity against pre-third-instar larvae of Mythimna separata (Oriental armyworm) assessed as corrected mortality rate at 1 mg/ml measured after 10 days by the leaf-dipping method2013Journal of agricultural and food chemistry, Jan-23, Volume: 61, Issue:3
Synthesis and quantitative structure-activity relationship (QSAR) study of novel 4-acyloxypodophyllotoxin derivatives modified in the A and C rings as insecticidal agents.
AID1100883Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean weight of pupae at 5 ug/ml in artificial diet (Rvb = 281.5 +/- 10.3 mg)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1100886Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean pupation at 5 ug/ml in artificial diet (Rvb = 87.5 %)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1082997Insecticidal activity against pre-third-instar larvae of Mythimna separata (Oriental armyworm) in wheat leaves at 1 mg/mL after 20 days by leaf-dipping method2012Journal of agricultural and food chemistry, Aug-29, Volume: 60, Issue:34
Synthesis and quantitative structure-activity relationship (QSAR) study of novel isoxazoline and oxime derivatives of podophyllotoxin as insecticidal agents.
AID1092096In vivo insecticidal activity against pre-third-instar larval stage of Mythimna separata (Oriental armyworm) in corn leaves assessed as corrected mortality rate at 1 mg/ml treated for 3 secs before larval infestation on corn leaves measured after 35 days 2011Bioorganic & medicinal chemistry letters, Sep-15, Volume: 21, Issue:18
Natural products-based insecticidal agents 11. Synthesis and insecticidal activity of novel 4α-arylsulfonyloxybenzyloxy-2β-chloropodophyllotoxin derivatives against Mythimna separata Walker in vivo.
AID1100916Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean weight gain at 5 ug/ml in artificial diet measured after 7 days (Rvb = 75.5 +/- 8.24 mg)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1092157Insecticidal activity against pre-third-instar larvae of Mythimna separata (Oriental armyworm) in compound treated fresh corn leaves assessed as corrected mortality at 1 mg/ml measured after 20 days by leaf-dipping method2012Bioorganic & medicinal chemistry letters, Sep-01, Volume: 22, Issue:17
Regioselective synthesis of fraxinellone-based hydrazone derivatives as insecticidal agents.
AID1100909Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean length at 5 ug/ml in artificial diet measured after 7 days (Rvb = 0.95 +/- 0.2 cm)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID590129Insecticidal activity against Mythimna separata Walker assessed as mortality at 1 mg/mL by leaf dipping method2011Bioorganic & medicinal chemistry letters, Apr-01, Volume: 21, Issue:7
Natural products-based insecticidal agents 9. Design, semisynthesis and insecticidal activity of 28-acyloxy derivatives of toosendanin against Mythimna separata Walker in vivo.
AID368092Antibotulinum activity against botulinum neurotoxin serotype A-induced toxicity in iv dosed mouse assessed as time to death2009Bioorganic & medicinal chemistry, Feb-01, Volume: 17, Issue:3
Function-oriented synthesis applied to the anti-botulinum natural product toosendanin.
AID1100920Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mortality at 5 ug/ml in artificial diet measured after 7 days (Rvb = 8.33%)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1092156Insecticidal activity against pre-third-instar larvae of Mythimna separata (Oriental armyworm) in compound treated fresh corn leaves assessed as corrected mortality at 1 mg/ml measured after 35 days by leaf-dipping method2012Bioorganic & medicinal chemistry letters, Sep-01, Volume: 22, Issue:17
Regioselective synthesis of fraxinellone-based hydrazone derivatives as insecticidal agents.
AID1101706Antifeedant activity against adult of Tribolium castaneum (red flour beetle) after 3 days2002Journal of agricultural and food chemistry, Mar-13, Volume: 50, Issue:6
Feeding deterrents from Dictamnus dasycarpus Turcz against two stored-product insects.
AID1100872Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean emergence at 25 ug/ml in artificial diet (Rvb = 83.3 %)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1101937Antifeedant activity against larvae of Spodoptera eridania in Cucurbita maxima leaves at 10 ug/cm2 after 24 hr by leaf disk choice test2002Bioscience, biotechnology, and biochemistry, Aug, Volume: 66, Issue:8
Potent limonoid insect antifeedant from Melia azedarach.
AID1100888Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean length at 52 ug/ml in artificial diet measured after 7 days (Rvb = 28 +/- 4.1 mg)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1101942Antifeedant activity against larvae of Epilachna paenulata in Cucurbita maxima leaves at 8 ug/cm2 after 24 hr by leaf disc choice test2002Bioscience, biotechnology, and biochemistry, Aug, Volume: 66, Issue:8
Potent limonoid insect antifeedant from Melia azedarach.
AID1100874Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean pupation at 25 ug/ml in artificial diet (Rvb = 87.5 %)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1100877Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean emergence days at 25 ug/ml in artificial diet (Rvb = 33 days)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1092098In vivo insecticidal activity against pre-third-instar larval stage of Mythimna separata (Oriental armyworm) in corn leaves assessed as corrected mortality rate at 1 mg/ml treated for 3 secs before larval infestation on corn leaves measured after 10 days 2011Bioorganic & medicinal chemistry letters, Sep-15, Volume: 21, Issue:18
Natural products-based insecticidal agents 11. Synthesis and insecticidal activity of novel 4α-arylsulfonyloxybenzyloxy-2β-chloropodophyllotoxin derivatives against Mythimna separata Walker in vivo.
AID1100876Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean emergence days at 5 ug/ml in artificial diet (Rvb = 33 days)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1091894In vivo insecticidal activity against pre-third-instar larval stage of Mythimna separata (Oriental armyworm) in corn leaves assessed as corrected mortality rate at 1 mg/ml treated for 3 secs before larval infestation on corn leaves measured after 10 days 2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Natural products-based insecticidal agents 6. Design, semisynthesis, and insecticidal activity of novel monomethyl phthalate derivatives of podophyllotoxin against Mythimna separata Walker in vivo.
AID1100892Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean length at 25 ug/ml in artificial diet measured after 7 days (Rvb = 28 +/- 4.1 mg)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1100903Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mortality at 25 ug/ml in artificial diet measured after 7 days (Rvb = 8.33%)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1080796In vivo insecticidal activity against pre-third-instar larval stage of Mythimna separata (Oriental armyworm) in corn leaves assessed as corrected mortality rate at 1 mg/ml treated for 3 secs before larval infestation measured after 12 days by leaf-dipping2009Journal of agricultural and food chemistry, Sep-09, Volume: 57, Issue:17
Semisynthesis and quantitative structure-activity relationship (QSAR) study of novel aromatic esters of 4'-demethyl-4-deoxypodophyllotoxin as insecticidal agents.
AID1101708Antifeedant activity against adult of Sitophilus zeamais after 3 days2002Journal of agricultural and food chemistry, Mar-13, Volume: 50, Issue:6
Feeding deterrents from Dictamnus dasycarpus Turcz against two stored-product insects.
AID1112939Insecticidal activity against pre-third-instar larvae of Mythimna separata (Oriental armyworm) assessed as corrected mortality rate at 1 mg/ml measured after 35 days by the leaf-dipping method2013Journal of agricultural and food chemistry, Jan-23, Volume: 61, Issue:3
Synthesis and quantitative structure-activity relationship (QSAR) study of novel 4-acyloxypodophyllotoxin derivatives modified in the A and C rings as insecticidal agents.
AID1092097In vivo insecticidal activity against pre-third-instar larval stage of Mythimna separata (Oriental armyworm) in corn leaves assessed as corrected mortality rate at 1 mg/ml treated for 3 secs before larval infestation on corn leaves measured after 20 days 2011Bioorganic & medicinal chemistry letters, Sep-15, Volume: 21, Issue:18
Natural products-based insecticidal agents 11. Synthesis and insecticidal activity of novel 4α-arylsulfonyloxybenzyloxy-2β-chloropodophyllotoxin derivatives against Mythimna separata Walker in vivo.
AID1091893In vivo insecticidal activity against pre-third-instar larval stage of Mythimna separata (Oriental armyworm) in corn leaves assessed as corrected mortality rate at 1 mg/ml treated for 3 secs before larval infestation on corn leaves measured after 20 days 2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Natural products-based insecticidal agents 6. Design, semisynthesis, and insecticidal activity of novel monomethyl phthalate derivatives of podophyllotoxin against Mythimna separata Walker in vivo.
AID1082824Antifeedant activity against Mythimna separata (Oriental armyworm) larvae assessed as antifeedant index by area of the leaf consumed2012Journal of agricultural and food chemistry, Apr-04, Volume: 60, Issue:13
Metabolites from Aspergillus fumigatus, an endophytic fungus associated with Melia azedarach, and their antifungal, antifeedant, and toxic activities.
AID1082880Insecticidal activity against Mythimna separata (Oriental armyworm) in wheat leaves assessed as mortality rate at 1 mg/mL at 25 degC measured after 35 days by leaf-dipping method relative to control2012Journal of agricultural and food chemistry, Jul-18, Volume: 60, Issue:28
Synthesis and insecticidal activity of some novel fraxinellone-based esters.
AID1082881Insecticidal activity against Mythimna separata (Oriental armyworm) in wheat leaves assessed as mortality rate at 1 mg/mL at 25 degC measured after 25 days by leaf-dipping method relative to control2012Journal of agricultural and food chemistry, Jul-18, Volume: 60, Issue:28
Synthesis and insecticidal activity of some novel fraxinellone-based esters.
AID1091879In vivo insecticidal activity against pre-third-instar larval stage of Mythimna separata (Oriental armyworm) in corn leaves assessed as corrected mortality rate at 1 mg/ml treated for 3 secs before larval infestation on corn leaves measured after 30 days 2010Bioorganic & medicinal chemistry letters, Apr-15, Volume: 20, Issue:8
Natural products-based insecticidal agents 5. Design, semisynthesis and insecticidal activity of novel 4'-substituted benzenesulfonate derivatives of 4-deoxypodophyllotoxin against Mythimna separata Walker in vivo.
AID1100893Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean weight gain at 5 ug/ml in artificial diet measured after 7 days (Rvb = 469.5 +/- 6.59 mg)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1100873Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean emergence at 52 ug/ml in artificial diet (Rvb = 83.3 %)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1102049Antifeedant activity against third-instar larval stage of Epilachna paenulata infested cucurbita maxima leaves assessed as feeding reduction after 24 hr by leaf disk choice assay2003Journal of agricultural and food chemistry, Jan-15, Volume: 51, Issue:2
Antifeedant and insecticide properties of a limonoid from Melia azedarach (Meliaceae) with potential use for pest management.
AID1100885Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean weight of pupae at 52 ug/ml in artificial diet (Rvb = 281.5 +/- 10.3 mg)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1100898Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean weight gain at 52 ug/ml in artificial diet measured after 7 days (Rvb = 469.5 +/- 6.59 mg)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1091881In vivo insecticidal activity against pre-third-instar larval stage of Mythimna separata (Oriental armyworm) in corn leaves assessed as corrected mortality rate at 1 mg/ml treated for 3 secs before larval infestation on corn leaves measured after 10 days 2010Bioorganic & medicinal chemistry letters, Apr-15, Volume: 20, Issue:8
Natural products-based insecticidal agents 5. Design, semisynthesis and insecticidal activity of novel 4'-substituted benzenesulfonate derivatives of 4-deoxypodophyllotoxin against Mythimna separata Walker in vivo.
AID1082823Toxicity in Artemia salina (brine shrimp) at 28 degC after 48 hr2012Journal of agricultural and food chemistry, Apr-04, Volume: 60, Issue:13
Metabolites from Aspergillus fumigatus, an endophytic fungus associated with Melia azedarach, and their antifungal, antifeedant, and toxic activities.
AID721566Toxicity in brine shrimp larvae assessed as mortality after 24 hrs by microtiter plate analysis2013European journal of medicinal chemistry, Jan, Volume: 59Lignans from Schisandra sphenathera Rehd. et Wils. and semisynthetic schisantherin A analogues: absolute configuration, and their estrogenic and anti-proliferative activity.
AID1100906Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean length at 25 ug/ml in artificial diet measured after 7 days (Rvb = 0.95 +/- 0.2 cm)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1100899Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mortality measured after 7 days2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1100913Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean weight gain at 25 ug/ml in artificial diet measured after 7 days (Rvb = 75.5 +/- 8.24 mg)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1101707Antifeedant activity against larvae of Tribolium castaneum (red flour beetle) after 3 days2002Journal of agricultural and food chemistry, Mar-13, Volume: 50, Issue:6
Feeding deterrents from Dictamnus dasycarpus Turcz against two stored-product insects.
AID1101933Antifeedant activity against larvae of Spodoptera eridania in Cucurbita maxima leaves at 0.25 ug/cm2 after 24 hr by leaf disk choice test2002Bioscience, biotechnology, and biochemistry, Aug, Volume: 66, Issue:8
Potent limonoid insect antifeedant from Melia azedarach.
AID1082996Insecticidal activity against pre-third-instar larvae of Mythimna separata (Oriental armyworm) in wheat leaves at 1 mg/mL after 33 days by leaf-dipping method2012Journal of agricultural and food chemistry, Aug-29, Volume: 60, Issue:34
Synthesis and quantitative structure-activity relationship (QSAR) study of novel isoxazoline and oxime derivatives of podophyllotoxin as insecticidal agents.
AID1101935Antifeedant activity against larvae of Spodoptera eridania in Cucurbita maxima leaves at 1 ug/cm2 after 24 hr by leaf disk choice test2002Bioscience, biotechnology, and biochemistry, Aug, Volume: 66, Issue:8
Potent limonoid insect antifeedant from Melia azedarach.
AID1101934Antifeedant activity against larvae of Spodoptera eridania in Cucurbita maxima leaves at 0.5 ug/cm2 after 24 hr by leaf disk choice test2002Bioscience, biotechnology, and biochemistry, Aug, Volume: 66, Issue:8
Potent limonoid insect antifeedant from Melia azedarach.
AID1100880Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean time to pupation at 5 ug/ml in artificial diet (Rvb = 22 days)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1091892In vivo insecticidal activity against pre-third-instar larval stage of Mythimna separata (Oriental armyworm) in corn leaves assessed as corrected mortality rate at 1 mg/ml treated for 3 secs before larval infestation on corn leaves measured after 33 days 2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Natural products-based insecticidal agents 6. Design, semisynthesis, and insecticidal activity of novel monomethyl phthalate derivatives of podophyllotoxin against Mythimna separata Walker in vivo.
AID1100918Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean length at 52 ug/ml in artificial diet measured after 7 days (Rvb = 0.95 +/- 0.2 cm)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1100911Insecticidal activity against Spodoptera frugiperda (fall armyworm) assessed as mean weight gain at 52 ug/ml in artificial diet measured after 7 days (Rvb = 75.5 +/- 8.24 mg)2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae).
AID1103949Antifeedant activity against third-instar Epilachna paenulata measured assessed per cm2 leaf disk2009Bioresource technology, Jul, Volume: 100, Issue:14
Antifeedant activity of ethanolic extract from Flourensia oolepis and isolation of pinocembrin as its active principle compound.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (127)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (3.94)18.7374
1990's7 (5.51)18.2507
2000's30 (23.62)29.6817
2010's54 (42.52)24.3611
2020's31 (24.41)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.76

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 Index28.76 (24.57)
Research Supply Index4.75 (2.92)
Research Growth Index5.16 (4.65)
Search Engine Demand Index36.71 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.76)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews5 (4.35%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other20 (100.00%)84.16%
Other110 (95.65%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
uracil
2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder		2.0710pyrimidine nucleobase;
pyrimidone		allergen;
Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
prodrug;
Saccharomyces cerevisiae metabolite
catechin
[no description available]		2.0510hydroxyflavan
rotenone
Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.		2.0510organic heteropentacyclic compound;
rotenones		antineoplastic agent;
metabolite;
mitochondrial NADH:ubiquinone reductase inhibitor;
phytogenic insecticide;
piscicide;
toxin
podophyllotoxin
Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.		2.9840furonaphthodioxole;
lignan;
organic heterotetracyclic compound		antimitotic;
antineoplastic agent;
keratolytic drug;
microtubule-destabilising agent;
plant metabolite;
tubulin modulator
flavone
flavone: RN given refers to unlabeled cpd; structure given in first source. flavone : The simplest member of the class of flavones that consists of 4H-chromen-4-one bearing a phenyl substituent at position 2.		2.0510flavonesmetabolite;
nematicide
hymexazol
hymexazol : A member of the class of isoxazoles carrying hydroxy and methyl substituents at positions 3 and 5 respectively. It is used worldwide as a systemic soil and seed fungicide for the control of diseases caused by Fusarium, Aphanomyces, Pythium, and Corticium spp. in rice, sugarbeet, fodderbeet, vegetables, cucurbits, and ornamentals.. hymexazol: a chemical used to sterilize soil; structure in first source		2.0710heteroaryl hydroxy compound;
isoxazoles		antifungal agrochemical
carbendazim
carbendazim: carcinogen when combined with sodium nitrite; principle metabolite of thiophanate methyl & benomyl; structure. carbendazim : A member of the class of benzimidazoles that is 2-aminobenzimidazole in which the primary amino group is substituted by a methoxycarbonyl group. A fungicide, carbendazim controls Ascomycetes, Fungi Imperfecti, and Basidiomycetes on a wide variety of crops, including bananas, cereals, cotton, fruits, grapes, mushrooms, ornamentals, peanuts, sugarbeet, soybeans, tobacco, and vegetables.		2.0710benzimidazole fungicide;
benzimidazoles;
benzimidazolylcarbamate fungicide;
carbamate ester		antifungal agrochemical;
antinematodal drug;
metabolite;
microtubule-destabilising agent
pinocembrin
pinocembrin : A dihydroxyflavanone in which the two hydroxy groups are located at positions 5 and 7. A natural product found in Piper sarmentosum and Cryptocarya chartacea.		2.0510(2S)-flavan-4-one;
dihydroxyflavanone		antineoplastic agent;
antioxidant;
metabolite;
neuroprotective agent;
vasodilator agent
dictamnine
dictamnine: furanoquinoline alkaloid; crosslinks DNA in presence of ultraviolet light		2.0110alkaloid antibiotic;
organic heterotricyclic compound;
organonitrogen heterocyclic compound;
oxacycle
fraxinellone
fraxinellone: structure given in first source; RN given for (3R-cis)-isomer		2.74302-benzofurans
cyclo(prolylglycyl)
cyclo(prolylglycyl): RN given is for 17O-labeled cpd		2.0710
4'-demethyldesoxypodophyllotoxin
4'-demethyldesoxypodophyllotoxin: from the root of Bursera tonkinensis Guillaum; structure in first source. 4'-demethyldeoxypodophyllotoxin : A member of the class of furonaphthodioxoles that is (5R,5aR,8aR)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one substituted at position 5 by a 4-hydroxy-3,5-dimethoxyphenyl group.		2.0510furonaphthodioxole;
gamma-lactone;
lignan;
methoxybenzenes;
phenols		antineoplastic agent;
antioxidant;
immunosuppressive agent;
plant metabolite
brevianamide f
brevianamide F : A pyrrolopyrazine that is hexahydropyrrolo[1,2-a]pyrazine-1,4-dione bearing an indol-3-ylmethyl substituent at position 3 (the 3S,8aS-diastereomer, obtained by formal cyclocondensation of L-tryptophan and L-proline).. brevianamide F: isolated from the endophyte from Aspergillus fumigatus associated with Melia azedarach L that could be used to develop a natural eco-friendly herbicide.structure in first source		2.0710dipeptide;
indoles;
pyrrolopyrazine		metabolite
anthricin
deoxypodophyllotoxin : A member of the class of furonaphthodioxoles that is (5R,5aR,8aR)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one substituted at position 5 by a 3,4,5-trimethoxyphenyl group.. anthricin: antitumor constituent from Anthriscus sylvestris (L.) Hoffm; structure in first source		2.0510furonaphthodioxole;
gamma-lactone;
lignan;
methoxybenzenes		antineoplastic agent;
apoptosis inducer;
plant metabolite
tryptoquivaline
fumitremorgin C : An organic heteropentacyclic compound that is a mycotoxic indole alkaloid produced by several fungi. A potent and specific inhibitor of the breast cancer resistance protein multidrug transporter.		2.0710aromatic ether;
indole alkaloid;
organic heteropentacyclic compound		breast cancer resistance protein inhibitor;
mycotoxin
naringenin
(S)-naringenin : The (S)-enantiomer of naringenin.		2.0510(2S)-flavan-4-one;
naringenin		expectorant;
plant metabolite
schizandrin c
schizandrin C: from Schizandra chinensis Baill & Fructus schisandrae; protects liver from carbon tetrachloride injury;		2.0810tannin
schizandrin
[no description available]		2.0810
gomisin j
gomisin J: a lignan from Schizandra fruits		2.0810
helvolic acid
helvolic acid : A steroid C-21 acid having a 29-nordammarane skeleton substituted with an acetoxy group at C-16 and oxo groups at C-3 and -7, with double bonds at C-1, -17(20) and -24.. helvolic acid: structure		2.07103-oxo-Delta(1) steroid;
acetate ester;
monocarboxylic acid;
steroid acid		antibacterial agent;
fungal metabolite;
mycotoxin
8-hydroxypinoresinol
8-hydroxypinoresinol: cytoprotective lignan from Forsythia suspensa; structure in first source		2.0810lignan
quercetin
[no description available]		2.05107-hydroxyflavonol;
pentahydroxyflavone		antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
chrysin
chrysin : A dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7.		2.05107-hydroxyflavonol;
dihydroxyflavone		anti-inflammatory agent;
antineoplastic agent;
antioxidant;
EC 2.7.11.18 (myosin-light-chain kinase) inhibitor;
hepatoprotective agent;
plant metabolite
yunaconitine
yunaconitine: alkaloid found in folk medicine caowu; RN given refers to (1alpha,3alpha,6alpha,14alpha,16beta)-isomer; RN for cpd without isomeric designation not avail 8/91. yunaconitine : A diterpene alkaloid with formula C35H49NO11 that is isolated from several Aconitum species.		2.0610acetate ester;
aromatic ether;
benzoate ester;
bridged compound;
diterpene alkaloid;
organic heteropolycyclic compound;
polyether;
secondary alcohol;
tertiary alcohol;
tertiary amino compound		antifeedant;
human urinary metabolite;
phytotoxin;
plant metabolite;
xenobiotic
jbp 485
JBP 485: has antihepatitis activity		2.0710
pseurotin
pseurotin: metabolite isolated from culture filtrates of Pseudeurotium ovalis Stolk; structure. pseurotin A : A spirocyclic that is 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione bearing 1,2-dihydroxyhex-3-en-1-yl, methyl, methoxy, benzoyl and hydroxy substituents at positions 2, 3, 8, 8 and 9 respectively.		2.0710azaspiro compound;
lactam;
oxaspiro compound		metabolite
tryprostatin a
tryprostatin A: isolated from Aspergillus fumigatus; a mammalian cell cycle inhibitor; structure given in first source. tryprostatin A : A cyclic dipeptide that is brevianamide F (cyclo-L-Trp-L-Pro) substituted at positions 2 and 6 on the indole ring by prenyl and methoxy groups respectively.		2.0710aromatic ether;
dipeptide;
indole alkaloid;
indoles;
pyrrolopyrazine		breast cancer resistance protein inhibitor
fumiquinazoline f
fumiquinazoline F: structure in first source. fumiquinazoline F : A fumiquinazoline that consists of pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione bearing a methyl substituent at position 1 and an indol-3-yl group at position 4.		2.0710fumiquinazoline;
indoles;
pyrazinoquinazoline
(S)-Isosclerone
[no description available]		2.0710tetralins
5-Hydroxyauranetin
5-hydroxy-3,6,7,8,4'-pentamethoxyflavone: has diuretic activity; isolated from Rubus rosaefolius		2.0510ether;
flavonoids
fumiquinazoline a
fumiquinazoline A : A fumiquinazoline that consists of imidazoindole and pyrazinoquinazoline units connected by a methylene group.. fumiquinazoline A: structure in first source		2.0710fumiquinazoline;
imidazoindole;
pyrazinoquinazoline
gedunin
[no description available]		210acetate ester;
enone;
epoxide;
furans;
lactone;
limonoid;
organic heteropentacyclic compound;
pentacyclic triterpenoid		antimalarial;
antineoplastic agent;
Hsp90 inhibitor;
plant metabolite
6-methoxyspirotryprostatin b
6-methoxyspirotryprostatin B: cytotoxic compound from the marine-derived fungus Aspergillus sydowi; structure in first source. 6-methoxyspirotryprostatin B : An indole alkaloid isolated from a marine-derived fungal strain Aspergillus sydowii PFW1-13 and has been shown to exhibit cytotoxic activity.		2.0710aromatic ether;
azaspiro compound;
indole alkaloid;
indolones		antineoplastic agent;
Aspergillus metabolite
chlorine
chloride : A halide anion formed when chlorine picks up an electron to form an an anion.		1.9810halide anion;
monoatomic chlorine		cofactor;
Escherichia coli metabolite;
human metabolite
taurine
[no description available]		2.110amino sulfonic acid;
zwitterion		antioxidant;
Escherichia coli metabolite;
glycine receptor agonist;
human metabolite;
mouse metabolite;
nutrient;
radical scavenger;
Saccharomyces cerevisiae metabolite
4-aminopyridine
[no description available]		3.7930aminopyridine;
aromatic amine		avicide;
orphan drug;
potassium channel blocker
acetaminophen
paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.. Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.		2.2110acetamides;
phenols		antipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
cyclooxygenase 3 inhibitor;
environmental contaminant;
ferroptosis inducer;
geroprotector;
hepatotoxic agent;
human blood serum metabolite;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
xenobiotic
bay-k-8644
methyl 2,6-dimethyl-5-nitro-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylate : A pentasubstituted dihydropyridine carrying methoxycarbonyl, 2-(trifluoromethyl)phenyl and nitro substituents at positions 3, 4 and 5 respectively as well as two methyl substituents at positions 2 and 6.. Bay-K-8644 : A racemate comprising equimolar amounts of (R)- and (S)-Bay-K-8644. 3-Pyridinecarboxylic acid, 1,4-dihydro-2,6-dimethyl-5-nitro-4-(2-(trifluoromethyl)phenyl)-, Methyl ester: A dihydropyridine derivative, which, in contrast to NIFEDIPINE, functions as a calcium channel agonist. The compound facilitates Ca2+ influx through partially activated voltage-dependent Ca2+ channels, thereby causing vasoconstrictor and positive inotropic effects. It is used primarily as a research tool.		1.9910(trifluoromethyl)benzenes;
C-nitro compound;
dihydropyridine;
methyl ester
verapamil
verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.		1.9910aromatic ether;
nitrile;
polyether;
tertiary amino compound
dantrolene
dantrolene : The hydrazone resulting from the formal condensation of 5-(4-nitrophenyl)furfural with 1-aminohydantoin. A ryanodine receptor antagonist used for the relief of chronic severe spasticity and malignant hyperthermia.. Dantrolene: Skeletal muscle relaxant that acts by interfering with excitation-contraction coupling in the muscle fiber. It is used in spasticity and other neuromuscular abnormalities. Although the mechanism of action is probably not central, dantrolene is usually grouped with the central muscle relaxants.		1.9910hydrazone;
imidazolidine-2,4-dione		muscle relaxant;
neuroprotective agent;
ryanodine receptor antagonist
fluorouracil
5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.. Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.		2.2510nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
nifedipine
Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.		7.9240C-nitro compound;
dihydropyridine;
methyl ester		calcium channel blocker;
human metabolite;
tocolytic agent;
vasodilator agent
tetraethylammonium
Tetraethylammonium: A potassium-selective ion channel blocker. (From J Gen Phys 1994;104(1):173-90)		1.9910quaternary ammonium ion
reserpine
reserpine : An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.. Reserpine: An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use.		1.9910alkaloid ester;
methyl ester;
yohimban alkaloid		adrenergic uptake inhibitor;
antihypertensive agent;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
environmental contaminant;
first generation antipsychotic;
plant metabolite;
xenobiotic
amifampridine
Amifampridine: 4-Aminopyridine derivative that acts as a POTASSIUM CHANNEL blocker to increase release of ACETYLCHOLINE from nerve terminals. It is used in the treatment of CONGENITAL MYASTHENIC SYNDROMES.		3.520aminopyridine
lysine
Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.		2.3110aspartate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
lysine;
organic molecular entity;
proteinogenic amino acid		algal metabolite;
anticonvulsant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
tubocurarine
tubocurarine : A benzylisoquinoline alkaloid muscle relaxant which constitutes the active component of curare.. Tubocurarine: A neuromuscular blocker and active ingredient in CURARE; plant based alkaloid of Menispermaceae.. isoquinoline alkaloid : Any alkaloid that has a structure based on an isoquinoline nucleus. They are derived from the amino acids like tyrosine and phenylalanine.		1.9610bisbenzylisoquinoline alkaloiddrug allergen;
muscle relaxant;
nicotinic antagonist
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.		1.9910diether;
tertiary amino compound;
tetracarboxylic acid		chelator
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.		7.110furans;
mancude organic heteromonocyclic parent;
monocyclic heteroarene		carcinogenic agent;
hepatotoxic agent;
Maillard reaction product
monocrotaline
Monocrotaline: A pyrrolizidine alkaloid and a toxic plant constituent that poisons livestock and humans through the ingestion of contaminated grains and other foods. The alkaloid causes pulmonary artery hypertension, right ventricular hypertrophy, and pathological changes in the pulmonary vasculature. Significant attenuation of the cardiopulmonary changes are noted after oral magnesium treatment.		2.2110pyrrolizidine alkaloid
podophyllotoxin
Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.		2.7630furonaphthodioxole;
lignan;
organic heterotetracyclic compound		antimitotic;
antineoplastic agent;
keratolytic drug;
microtubule-destabilising agent;
plant metabolite;
tubulin modulator
dithiothreitol
1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.. 1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.		2.01101,4-dimercaptobutane-2,3-diol;
butanediols;
dithiol;
glycol;
thiol		chelator;
human metabolite;
reducing agent
ecdysone
[no description available]		3.141014alpha-hydroxy steroid;
22-hydroxy steroid;
25-hydroxy steroid;
2beta-hydroxy steroid;
3beta-sterol;
6-oxo steroid;
ecdysteroid		prohormone
monomethyl phthalate
monomethyl phthalate: structure in first source		2.0510methyl ester;
phthalic acid monoester
cadmium
Cadmium: An element with atomic symbol Cd, atomic number 48, and atomic weight 112.41. It is a metal and ingestion will lead to CADMIUM POISONING.. elemental cadmium : An element in the zinc group of the periodic table with atomic number 48, atomic mass 112, M.P. 321degreeC, and B.P. 765degreeC). An odourless, tasteless, and highly poisonous soft, ductile, lustrous metal with electropositive properties. It has eight stable isotopes: (106)Cd, (108)Cd,(110)Cd, (111)Cd, (112)Cd, (113)Cd, (114)Cd and (116)Cd, with (112)Cd and (114)Cd being the most common.		1.9810cadmium molecular entity;
zinc group element atom
cadmium chloride
Cadmium Chloride: A cadmium halide in the form of colorless crystals, soluble in water, methanol, and ethanol. It is used in photography, in dyeing, and calico printing, and as a solution to precipitate sulfides. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). cadmium dichloride : A cadmium coordination entity in which cadmium(2+) and Cl(-) ions are present in the ratio 2:1. Although considered to be ionic, it has considerable covalent character to its bonding.		1.9810cadmium coordination entity
barium chloride
barium chloride: RN given refers to parent cpd. barium chloride : The inorganic dichloride salt of barium.		1.9810barium salt;
inorganic chloride		potassium channel blocker
paclitaxel
Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).		7.610taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
lovastatin
Lovastatin: A fungal metabolite isolated from cultures of Aspergillus terreus. The compound is a potent anticholesteremic agent. It inhibits 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It also stimulates the production of low-density lipoprotein receptors in the liver.. lovastatin : A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom).		2.3110delta-lactone;
fatty acid ester;
hexahydronaphthalenes;
polyketide;
statin (naturally occurring)		anticholesteremic drug;
antineoplastic agent;
Aspergillus metabolite;
prodrug
honokiol
[no description available]		2.1110biphenyls
peptide elongation factor 2
Peptide Elongation Factor 2: Peptide Elongation Factor 2 catalyzes the translocation of peptidyl-tRNA from the A site to the P site of eukaryotic ribosomes by a process linked to the hydrolysis of GTP to GDP.		2.610
lignans
Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)		2.1110
cerivastatin
cerivastatin : (3R,5S)-3,5-dihydroxyhept-6-enoic acid in which the (7E)-hydrogen is substituted by a 4-(4-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl group. Formerly used (as its sodium salt) to lower cholesterol and prevent cardiovascular disease, it was withdrawn from the market worldwide in 2001 following reports of a severe form of muscle toxicity.. cerivastatin: cerivastatin is the ((E)-(+))-isomer; structure given in first source		2.3110dihydroxy monocarboxylic acid;
pyridines;
statin (synthetic)
anethole
trans-anethole : The trans-stereoisomer of anethole.. anethole : A monomethoxybenzene that is methoxybenzene substituted by a prop-1-en-1-yl group at position 4.. anethole: an isomer of estragole; structurally similar to CAPSAICIN; has some neurological and insecticidal and skin absorption effects; RN given refers to unspecified stereoisomer		7.4720anetholeflavouring agent
1,2-bis(2-aminophenoxy)ethane n,n,n',n'-tetraacetic acid acetoxymethyl ester
[no description available]		1.9910
u-50488
3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-benzeneacetamide, (trans)-Isomer: A non-peptide, kappa-opioid receptor agonist which has also been found to stimulate the release of adrenocorticotropin (ADRENOCORTICOTROPIC HORMONE) via the release of hypothalamic arginine vasopressin (ARGININE VASOPRESSIN) and CORTICOTROPIN-RELEASING HORMONE. (From J Pharmacol Exp Ther 1997;280(1):416-21). U50488 : A monocarboxylic acid amide obtained by formal condensation between the carboxy group of 3,4-dichlorophenylacetic acid and the secondary amino group of (1R,2R)-N-methyl-2-(pyrrolidin-1-yl)cyclohexanamine		2.2510dichlorobenzene;
monocarboxylic acid amide;
N-alkylpyrrolidine		analgesic;
antitussive;
calcium channel blocker;
diuretic;
kappa-opioid receptor agonist
quercetin
[no description available]		7.21107-hydroxyflavonol;
pentahydroxyflavone		antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
scopoletin
[no description available]		2.1310hydroxycoumarinplant growth regulator;
plant metabolite
genistein
[no description available]		2.08107-hydroxyisoflavonesantineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
geroprotector;
human urinary metabolite;
phytoestrogen;
plant metabolite;
tyrosine kinase inhibitor
barium
Barium: An element of the alkaline earth group of metals. It has an atomic symbol Ba, atomic number 56, and atomic weight 138. All of its acid-soluble salts are poisonous.		2.4220alkaline earth metal atom;
elemental barium
tetrodotoxin
tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.. Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.		210azatetracycloalkane;
oxatetracycloalkane;
quinazoline alkaloid		animal metabolite;
bacterial metabolite;
marine metabolite;
neurotoxin;
voltage-gated sodium channel blocker
diosbulbin b
diosbulbin B: from the rhizome of Dioscorea bulbifera; structure in first source		2.2110naphthofuran
regorafenib
[no description available]		7.3110(trifluoromethyl)benzenes;
aromatic ether;
monochlorobenzenes;
monofluorobenzenes;
phenylureas;
pyridinecarboxamide		antineoplastic agent;
hepatotoxic agent;
tyrosine kinase inhibitor
cytochrome c-t
Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.		2.7630
cholecystokinin
Cholecystokinin: A peptide, of about 33 amino acids, secreted by the upper INTESTINAL MUCOSA and also found in the central nervous system. It causes gallbladder contraction, release of pancreatic exocrine (or digestive) enzymes, and affects other gastrointestinal functions. Cholecystokinin may be the mediator of satiety.		2.0110
snx 230
omega-conotoxin-MVIIC: isolated from Conus magus; amino acid sequence given in first source		2.0210
rhodojaponin iii
rhodojaponin III: from Rhododendron Molle G. Don; structure given in first source; RN given refers to (2beta,3beta,6beta,14R)-isomer; RN for cpd without isomeric designation not avail 7/91		2.0310diterpene
ConditionIndicatedRelationship StrengthStudiesTrials
Botulism, Infantile
[description not available]		04.9280
Botulism
A disease caused by potent protein NEUROTOXINS produced by CLOSTRIDIUM BOTULINUM which interfere with the presynaptic release of ACETYLCHOLINE at the NEUROMUSCULAR JUNCTION. Clinical features include abdominal pain, vomiting, acute PARALYSIS (including respiratory paralysis), blurred vision, and DIPLOPIA. Botulism may be classified into several subtypes (e.g., food-borne, infant, wound, and others). (From Adams et al., Principles of Neurology, 6th ed, p1208)		04.9280
ER-Negative PR-Negative HER2-Negative Breast Cancer
[description not available]		03.2230
Necrosis
The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.		07.4110
Triple Negative Breast Neoplasms
Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.		03.2230
Benign Neoplasms
[description not available]		04.6940
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.		04.6940
Colorectal Cancer
[description not available]		02.930
Colorectal Neoplasms
Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.		02.930
Blue-Eared Pig Disease
[description not available]		02.4110
Swine Diseases
Diseases of domestic swine and of the wild boar of the genus Sus.		02.4110
Cancer of Ovary
[description not available]		02.610
Ovarian Neoplasms
Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.		02.610
Bone Loss, Osteoclastic
[description not available]		02.610
Age-Related Osteoporosis
[description not available]		02.610
Bone Loss, Perimenopausal
[description not available]		02.610
Osteoporosis
Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.		07.610
Osteoporosis, Postmenopausal
Metabolic disorder associated with fractures of the femoral neck, vertebrae, and distal forearm. It occurs commonly in women within 15-20 years after menopause, and is caused by factors associated with menopause including estrogen deficiency.		02.610
Benign Neoplasms, Brain
[description not available]		02.6320
Astrocytoma, Grade IV
[description not available]		02.6320
Brain Neoplasms
Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.		02.6320
Glioblastoma
A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.		02.6320
Acute Liver Injury, Drug-Induced
[description not available]		03.7380
Chemical and Drug Induced Liver Injury
A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.		03.7380
Canine Diseases
[description not available]		02.610
Rodent Diseases
Diseases of rodents of the order RODENTIA. This term includes diseases of Sciuridae (squirrels), Geomyidae (gophers), Heteromyidae (pouched mice), Castoridae (beavers), Cricetidae (rats and mice), Muridae (Old World rats and mice), Erethizontidae (porcupines), and Caviidae (guinea pigs).		02.610
Esophageal Squamous Cell Carcinoma
A carcinoma that originates usually from cells on the surface of the middle and lower third of the ESOPHAGUS. Tumor cells exhibit typical squamous morphology and form large polypoid lesions. Mutations in RNF6, LZTS1, TGFBR2, DEC1, and WWOX1 genes are associated with this cancer.		07.610
Carcinoma, Epidermoid
[description not available]		03.0120
Cancer of Esophagus
[description not available]		02.610
Carcinoma, Squamous Cell
A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)		03.0120
Esophageal Neoplasms
Tumors or cancer of the ESOPHAGUS.		02.610
Carcinoma, Squamous Cell of Head and Neck
[description not available]		02.610
Cancer of Head
[description not available]		02.610
Cancer of Mouth
[description not available]		02.610
Squamous Cell Carcinoma of Head and Neck
The most common type of head and neck carcinoma that originates from cells on the surface of the NASAL CAVITY; MOUTH; PARANASAL SINUSES, SALIVARY GLANDS, and LARYNX. Mutations in TNFRSF10B, PTEN, and ING1 genes are associated with this cancer.		02.610
Head and Neck Neoplasms
Soft tissue tumors or cancer arising from the mucosal surfaces of the LIP; oral cavity; PHARYNX; LARYNX; and cervical esophagus. Other sites included are the NOSE and PARANASAL SINUSES; SALIVARY GLANDS; THYROID GLAND and PARATHYROID GLANDS; and MELANOMA and non-melanoma skin cancers of the head and neck. (from Holland et al., Cancer Medicine, 4th ed, p1651)		02.610
Mouth Neoplasms
Tumors or cancer of the MOUTH.		02.610
Colitis
Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.		07.2110
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.8130
Cancer of Stomach
[description not available]		02.8830
Stomach Neoplasms
Tumors or cancer of the STOMACH.		02.8830
Bone Cancer
[description not available]		02.6120
Osteogenic Sarcoma
[description not available]		02.6120
Bone Neoplasms
Tumors or cancer located in bone tissue or specific BONES.		02.6120
Osteosarcoma
A sarcoma originating in bone-forming cells, affecting the ends of long bones. It is the most common and most malignant of sarcomas of the bones, and occurs chiefly among 10- to 25-year-old youths. (From Stedman, 25th ed)		07.6120
Hepatocellular Carcinoma
[description not available]		03.2250
Cancer of Liver
[description not available]		03.0740
Metastase
[description not available]		02.6120
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.		03.2250
Liver Neoplasms
Tumors or cancer of the LIVER.		03.0740
Neoplasm Metastasis
The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.		02.6120
Innate Inflammatory Response
[description not available]		02.3110
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		07.3110
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.		02.1510
Cancer of Pancreas
[description not available]		02.1510
Pancreatic Neoplasms
Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).		02.1510
Carcinoma, Anaplastic
[description not available]		02.1510
Invasiveness, Neoplasm
[description not available]		02.1510
Carcinoma
A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.		07.1510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.1710
Obesity
A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).		02.1710
Breast Cancer
[description not available]		07.1710
Experimental Neoplasms
[description not available]		02.1710
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.1710
Carcinoma, Non-Small Cell Lung
[description not available]		02.5720
Cancer of Lung
[description not available]		02.8630
Carcinoma, Non-Small-Cell Lung
A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.		02.5720
Lung Neoplasms
Tumors or cancer of the LUNG.		02.8630
Diseases, Metabolic
[description not available]		02.2110
Metabolic Diseases
Generic term for diseases caused by an abnormal metabolic process. It can be congenital due to inherited enzyme abnormality (METABOLISM, INBORN ERRORS) or acquired due to disease of an endocrine organ or failure of a metabolically important organ such as the liver. (Stedman, 26th ed)		02.2110
Ewing Sarcoma
[description not available]		02.2110
Sarcoma, Ewing
A malignant tumor of the bone which always arises in the medullary tissue, occurring more often in cylindrical bones. The tumor occurs usually before the age of 20, about twice as frequently in males as in females.		02.2110
Gastric Stasis
[description not available]		02.1310
Muscle Contraction
A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.		02.1310
Gastroparesis
Chronic delayed gastric emptying. Gastroparesis may be caused by motor dysfunction or paralysis of STOMACH muscles or may be associated with other systemic diseases such as DIABETES MELLITUS.		02.1310
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		07.0510
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted
[description not available]		02.0610
Hepatitis C
INFLAMMATION of the LIVER in humans caused by HEPATITIS C VIRUS, a single-stranded RNA virus. Its incubation period is 30-90 days. Hepatitis C is transmitted primarily by contaminated blood parenterally and is often associated with transfusion and intravenous drug abuse. However, in a significant number of cases, the source of hepatitis C infection is unknown.		02.0610
Glial Cell Tumors
[description not available]		02.4120
Glioma
Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)		07.4120
Neuroblastoma
A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)		07.730
Ascariasis
Infection by nematodes of the genus ASCARIS. Ingestion of infective eggs causes diarrhea and pneumonitis. Its distribution is more prevalent in areas of poor sanitation and where human feces are used for fertilizer.		02.9410