Compounds > squamocin
Page last updated: 2024-11-08

squamocin

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Description

squamocin: from seeds of Annona squamosa; a trihydroxy-bis-tetrahydrofuran fatty acid lactone; inhibits E. coli NADH:quinone oxidoreductase (NDH-1); structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
AnnonagenusA plant genus of the family ANNONACEAE. It has edible fruit and seeds which contain acetogenins and benzoquinazoline and other alkaloids.[MeSH]AnnonaceaeThe custard-apple plant family of the order Magnoliales, subclass Magnoliidae, class Magnoliopsida. Some members provide large pulpy fruits and commercial timber. Leaves and wood are often fragrant. Leaves are simple, with smooth margins, and alternately arranged in two rows along the stems.[MeSH]

Cross-References

ID SourceID
PubMed CID441612
CHEMBL ID41177
CHEBI ID9246
SCHEMBL ID2702440
MeSH IDM0165910

Synonyms (16)

Synonym
squamocin
C08545
120298-30-8
bdbm50087503
3-{13-[5''-(1,5-dihydroxy-undecyl)-octahydro-[2,2'']bifuranyl-5-yl]-13-hydroxy-tridecyl}-5-methyl-5h-furan-2-one(squamocin)
3-{13-[5''-(1,5-dihydroxy-undecyl)-octahydro-[2,2'']bifuranyl-5-yl]-13-hydroxy-tridecyl}-5-methyl-5h-furan-2-one
chebi:9246 ,
CHEMBL41177 ,
(2s)-4-[(13r)-13-[(2r,5r)-5-[(2r,5r)-5-[(1s,5s)-1,5-dihydroxyundecyl]oxolan-2-yl]oxolan-2-yl]-13-hydroxytridecyl]-2-methyl-2h-furan-5-one
4-[13-hydroxy-13-[5-[5-(6-methyldodecan-2-yl)oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2h-furan-5-one
squamocin a
annonin i
2(5h)-furanone, 3-(13-(5'-(1,5-dimethylundecyl)octahydro(2,2'-bifuran)-5-yl)-13-hydroxytridecyl)-5-methyl-
SCHEMBL2702440
DTXSID80152793
Q27108334

Research Excerpts

Actions

ExcerptReferenceRelevance
"Squamocin was found to inhibit the growth of K562 cells in a time- and dose-dependent manner."( Induction of G2/M phase arrest by squamocin in chronic myeloid leukemia (K562) cells.
Hwang, SL; Lin, SR; Lin, YH; Lu, MC; Lu, YJ; Wang, SR; Wu, YC; Yang, SH, 2006)		1.33
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
polyketideNatural and synthetic compounds containing alternating carbonyl and methylene groups ('beta-polyketones'), biogenetically derived from repeated condensation of acetyl coenzyme A (via malonyl coenzyme A), and usually the compounds derived from them by further condensations, etc. Considered by many to be synonymous with the less frequently used terms acetogenins and ketides.
[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]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)IC50 (µMol)0.00060.00020.00220.0051AID144499
Acyl carrier protein, mitochondrialBos taurus (cattle)IC50 (µMol)0.00060.00020.00220.0051AID144499
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (5)

Processvia Protein(s)Taxonomy
mitochondrial electron transport, NADH to ubiquinoneNADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)
transmembrane transportNADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)
mitochondrial electron transport, NADH to ubiquinoneAcyl carrier protein, mitochondrialBos taurus (cattle)
fatty acid biosynthetic processAcyl carrier protein, mitochondrialBos taurus (cattle)
mitochondrial respiratory chain complex I assemblyAcyl carrier protein, mitochondrialBos taurus (cattle)
[2Fe-2S] cluster assemblyAcyl carrier protein, mitochondrialBos taurus (cattle)
transmembrane transportAcyl carrier protein, mitochondrialBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
NADH dehydrogenase (ubiquinone) activityNADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)
FMN bindingNADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)
metal ion bindingNADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)
NAD bindingNADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)
4 iron, 4 sulfur cluster bindingNADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)
fatty acid bindingAcyl carrier protein, mitochondrialBos taurus (cattle)
NADH dehydrogenase (ubiquinone) activityAcyl carrier protein, mitochondrialBos taurus (cattle)
oxidoreductase activityAcyl carrier protein, mitochondrialBos taurus (cattle)
mitochondrial large ribosomal subunit bindingAcyl carrier protein, mitochondrialBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
mitochondrial inner membraneNADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)
respiratory chain complex INADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)
mitochondrial matrixAcyl carrier protein, mitochondrialBos taurus (cattle)
mitochondrial membraneAcyl carrier protein, mitochondrialBos taurus (cattle)
respiratory chain complex IAcyl carrier protein, mitochondrialBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (86)

Assay IDTitleYearJournalArticle
AID380682Mutagenic activity in Salmonella Typhimurium TA98 assessed as number of revertants at 20 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380684Mutagenic activity in Salmonella Typhimurium TA98 assessed as number of revertants at 100 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID42561Effective dose required for inhibitory activity against CAK1 human tumor cell line2003Journal of medicinal chemistry, Jul-17, Volume: 46, Issue:15
Acetogenins as selective inhibitors of the human ovarian 1A9 tumor cell line.
AID380694Mutagenic activity in Salmonella Typhimurium TA100 assessed as number of revertants at 1 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID9254Effective dose required for inhibitory activity against A549 human tumor cell line.2003Journal of medicinal chemistry, Jul-17, Volume: 46, Issue:15
Acetogenins as selective inhibitors of the human ovarian 1A9 tumor cell line.
AID93852Effective dose required for inhibitory activity against KB human tumor cell line.2003Journal of medicinal chemistry, Jul-17, Volume: 46, Issue:15
Acetogenins as selective inhibitors of the human ovarian 1A9 tumor cell line.
AID1061054Antitumor activity against mouse HepS cells xenografted in mouse assessed as tumor growth inhibition at 30 ug/kg2014European journal of medicinal chemistry, Jan, Volume: 71Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins.
AID380706Mutagenic activity in Salmonella Typhimurium TA102 assessed as number of revertants at 0.1 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID335279Cytotoxicity against mouse L1210 cells
AID380696Mutagenic activity in Salmonella Typhimurium TA100 assessed as number of revertants at 20 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380697Mutagenic activity in Salmonella Typhimurium TA100 assessed as number of revertants at 50 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380681Mutagenic activity in Salmonella Typhimurium TA98 assessed as number of revertants at 10 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID234417Relative potency of inhibition of NADH oxidase (IC50); 4-dehydroxy-4-hydroxylimonorolliniastatin-1 as standard2000Journal of medicinal chemistry, Dec-14, Volume: 43, Issue:25
Semisynthesis of antitumoral acetogenins: SAR of functionalized alkyl-chain bis-tetrahydrofuranic acetogenins, specific inhibitors of mitochondrial complex I.
AID399419Cytotoxicity against african green monkey Vero cells1998Journal of natural products, Jan, Volume: 61, Issue:1
Three new bistetrahydrofuran acetogenins from the seeds of Annona spinescens.
AID380667Antifeedant effect against Myzus persicae assessed as inhibition index at 100 ug/cm2 relative to control2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380686Mutagenic activity in Salmonella Typhimurium TA98 assessed as number of revertants at 0.1 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380705Mutagenic activity in Salmonella Typhimurium TA102 assessed as number of revertants at 0.01 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID94319Effective dose required for inhibitory activity against KB-VIN human tumor cell line.2003Journal of medicinal chemistry, Jul-17, Volume: 46, Issue:15
Acetogenins as selective inhibitors of the human ovarian 1A9 tumor cell line.
AID380713Mutagenic activity in Salmonella Typhimurium TA102 assessed as number of revertants at 0.01 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380708Mutagenic activity in Salmonella Typhimurium TA102 assessed as number of revertants at 10 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380714Mutagenic activity in Salmonella Typhimurium TA102 assessed as number of revertants at 1 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380675Insecticidal activity against Myzus persicae assessed as increase in mortality at 100 ug/cm2 observed daily for 4 days2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID399418Cytotoxicity against human KB cells1998Journal of natural products, Jan, Volume: 61, Issue:1
Three new bistetrahydrofuran acetogenins from the seeds of Annona spinescens.
AID380716Mutagenic activity in Salmonella Typhimurium TA102 assessed as number of revertants at 20 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID233953Ratio of IC50 of DB to that of NADH oxidase2000Journal of medicinal chemistry, Dec-14, Volume: 43, Issue:25
Semisynthesis of antitumoral acetogenins: SAR of functionalized alkyl-chain bis-tetrahydrofuranic acetogenins, specific inhibitors of mitochondrial complex I.
AID380687Mutagenic activity in Salmonella Typhimurium TA98 assessed as number of revertants at 1 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380718Mutagenic activity in Salmonella Typhimurium TA102 assessed as number of revertants at 100 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380692Mutagenic activity in Salmonella Typhimurium TA100 assessed as number of revertants at 0.01 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380710Mutagenic activity in Salmonella Typhimurium TA102 assessed as number of revertants at 50 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID144499Inhibition of NADH oxidase activity.2000Journal of medicinal chemistry, Dec-14, Volume: 43, Issue:25
Semisynthesis of antitumoral acetogenins: SAR of functionalized alkyl-chain bis-tetrahydrofuranic acetogenins, specific inhibitors of mitochondrial complex I.
AID380679Mutagenic activity in Salmonella Typhimurium TA98 assessed as number of revertants at 0.1 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380691Mutagenic activity in Salmonella Typhimurium TA98 assessed as number of revertants at 100 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380698Mutagenic activity in Salmonella Typhimurium TA100 assessed as number of revertants at 100 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380703Mutagenic activity in Salmonella Typhimurium TA100 assessed as number of revertants at 20 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380707Mutagenic activity in Salmonella Typhimurium TA102 assessed as number of revertants at 1 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380709Mutagenic activity in Salmonella Typhimurium TA102 assessed as number of revertants at 20 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380669Antifeedant effect against Leptinotarsa decemlineata assessed as feeding reduction at 10 ug/cm22000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID353193Cytotoxicity against human SMMC-7541 cells after 72 hrs by MTT assay2009Bioorganic & medicinal chemistry letters, Apr-15, Volume: 19, Issue:8
Structure-activity relationships of diverse annonaceous acetogenins against human tumor cells.
AID380695Mutagenic activity in Salmonella Typhimurium TA100 assessed as number of revertants at 10 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380712Mutagenic activity in Salmonella Typhimurium TA102 assessed as number of revertants at 0.01 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380672Antifeedant effect against Spodoptera littoralis L6 larvae assessed as relative consumption rate at 10 ug, po after 72 hrs2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380700Mutagenic activity in Salmonella Typhimurium TA100 assessed as number of revertants at 0.1 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID1061049Selectivity index, ratio of IC50 for mouse L1210 cells to IC50 for mouse P815 cells2014European journal of medicinal chemistry, Jan, Volume: 71Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins.
AID402924Cytotoxicity against human KB3-1 cells by colorimetric assay2004Journal of natural products, Jun, Volume: 67, Issue:6
Chamuvarinin, an acetogenin bearing a tetrahydropyran ring from the roots of Uvaria chamae.
AID380690Mutagenic activity in Salmonella Typhimurium TA98 assessed as number of revertants at 50 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380673Antifeedant effect against Spodoptera littoralis L6 larvae assessed as relative growth rate at 10 ug, po after 72 hrs2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380693Mutagenic activity in Salmonella Typhimurium TA100 assessed as number of revertants at 0.1 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380683Mutagenic activity in Salmonella Typhimurium TA98 assessed as number of revertants at 50 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID1061051Cytotoxicity against mouse P815 cells expressing biotin receptor after 72 hrs by MTT assay2014European journal of medicinal chemistry, Jan, Volume: 71Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins.
AID234411Percent of relative potency by NADH oxidase assay2000Journal of medicinal chemistry, Dec-14, Volume: 43, Issue:25
Semisynthesis of antitumoral acetogenins: SAR of functionalized alkyl-chain bis-tetrahydrofuranic acetogenins, specific inhibitors of mitochondrial complex I.
AID103064Effective dose required for inhibitory activity against MCF-7 human tumor cell line.2003Journal of medicinal chemistry, Jul-17, Volume: 46, Issue:15
Acetogenins as selective inhibitors of the human ovarian 1A9 tumor cell line.
AID380702Mutagenic activity in Salmonella Typhimurium TA100 assessed as number of revertants at 10 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID353191Cytotoxicity against human SGC7901 cells after 72 hrs by MTT assay2009Bioorganic & medicinal chemistry letters, Apr-15, Volume: 19, Issue:8
Structure-activity relationships of diverse annonaceous acetogenins against human tumor cells.
AID380701Mutagenic activity in Salmonella Typhimurium TA100 assessed as number of revertants at 1 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380668Mutagenic activity in Salmonella Typhimurium TA100 assessed as number of revertants at 100 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID217192Cytotoxic activity against african green monkey (Cercopithecus aethiops) kidney epithelial cells (VERO)2000Journal of medicinal chemistry, Apr-20, Volume: 43, Issue:8
Synthesis, spectroscopy, and cytotoxicity of glycosylated acetogenin derivatives as promising molecules for cancer therapy.
AID353194Cytotoxicity against human A-5408 cells after 72 hrs by MTT assay2009Bioorganic & medicinal chemistry letters, Apr-15, Volume: 19, Issue:8
Structure-activity relationships of diverse annonaceous acetogenins against human tumor cells.
AID380715Mutagenic activity in Salmonella Typhimurium TA102 assessed as number of revertants at 10 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID78999Effective dose required for inhibitory activity against HCT-8 human tumor cell line.2003Journal of medicinal chemistry, Jul-17, Volume: 46, Issue:15
Acetogenins as selective inhibitors of the human ovarian 1A9 tumor cell line.
AID380414Mutagenic activity in Salmonella Typhimurium TA98 assessed as number of revertants at 0.01 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID1061052Cytotoxicity against mouse 4T1 cells expressing biotin receptor after 72 hrs by MTT assay2014European journal of medicinal chemistry, Jan, Volume: 71Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins.
AID380680Mutagenic activity in Salmonella Typhimurium TA98 assessed as number of revertants at 1 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID156344Effective dose required for inhibitory activity against PC-3 human tumor cell line.2003Journal of medicinal chemistry, Jul-17, Volume: 46, Issue:15
Acetogenins as selective inhibitors of the human ovarian 1A9 tumor cell line.
AID97830Cytotoxic activity against mouse lymphocytic leukemia cells (L1210)2000Journal of medicinal chemistry, Apr-20, Volume: 43, Issue:8
Synthesis, spectroscopy, and cytotoxicity of glycosylated acetogenin derivatives as promising molecules for cancer therapy.
AID144480Inhibition of NADH decylubiquinone (DB) oxidoreductase activity.2000Journal of medicinal chemistry, Dec-14, Volume: 43, Issue:25
Semisynthesis of antitumoral acetogenins: SAR of functionalized alkyl-chain bis-tetrahydrofuranic acetogenins, specific inhibitors of mitochondrial complex I.
AID379779Cytotoxicity against human KB cells1999Journal of natural products, May, Volume: 62, Issue:5
A new bistetrahydrofuran acetogenin from the roots of Annona salzmanii.
AID2971Effective dose required for inhibitory activity against 1A9 human tumor cell line.2003Journal of medicinal chemistry, Jul-17, Volume: 46, Issue:15
Acetogenins as selective inhibitors of the human ovarian 1A9 tumor cell line.
AID380704Mutagenic activity in Salmonella Typhimurium TA100 assessed as number of revertants at 50 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380699Mutagenic activity in Salmonella Typhimurium TA100 assessed as number of revertants at 0.01 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380688Mutagenic activity in Salmonella Typhimurium TA98 assessed as number of revertants at 10 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380676Insecticidal activity against Myzus persicae assessed as increase in mortality at 50 ug/cm2 observed daily for 4 days2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380711Mutagenic activity in Salmonella Typhimurium TA102 assessed as number of revertants at 100 ug/plate in absence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380717Mutagenic activity in Salmonella Typhimurium TA102 assessed as number of revertants at 50 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID1061050Selectivity index, ratio of IC50 for mouse L1210 cells to IC50 for mouse 4T1 cells2014European journal of medicinal chemistry, Jan, Volume: 71Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins.
AID353192Cytotoxicity against human MCF7 cells after 72 hrs by MTT assay2009Bioorganic & medicinal chemistry letters, Apr-15, Volume: 19, Issue:8
Structure-activity relationships of diverse annonaceous acetogenins against human tumor cells.
AID380674Insecticidal activity against Leptinotarsa decemlineata assessed as mortality at 5 ug by hemolymph injection after 72 hrs2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID96186Cytotoxic activity against human epidermoid carcinoma cells (KB)2000Journal of medicinal chemistry, Apr-20, Volume: 43, Issue:8
Synthesis, spectroscopy, and cytotoxicity of glycosylated acetogenin derivatives as promising molecules for cancer therapy.
AID157342Effective dose required for inhibitory activity against PTX10 human tumor cell line2003Journal of medicinal chemistry, Jul-17, Volume: 46, Issue:15
Acetogenins as selective inhibitors of the human ovarian 1A9 tumor cell line.
AID380685Mutagenic activity in Salmonella Typhimurium TA98 assessed as number of revertants at 0.01 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID380415Antifeedant effect against Spodoptera littoralis assessed as feeding reduction at 100 ug/cm2 relative to control2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
AID379780Cytotoxicity against african green monkey Vero cells1999Journal of natural products, May, Volume: 62, Issue:5
A new bistetrahydrofuran acetogenin from the roots of Annona salzmanii.
AID353190Cytotoxicity against human HeLa cells after 72 hrs by MTT assay2009Bioorganic & medicinal chemistry letters, Apr-15, Volume: 19, Issue:8
Structure-activity relationships of diverse annonaceous acetogenins against human tumor cells.
AID1061053Cytotoxicity against mouse L1210 cells after 72 hrs by MTT assay2014European journal of medicinal chemistry, Jan, Volume: 71Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins.
AID84380Effective dose required for inhibitory activity against HOS human tumor cell line.2003Journal of medicinal chemistry, Jul-17, Volume: 46, Issue:15
Acetogenins as selective inhibitors of the human ovarian 1A9 tumor cell line.
AID201954Effective dose required for inhibitory activity against SK-MEL-2 human tumor cell line.2003Journal of medicinal chemistry, Jul-17, Volume: 46, Issue:15
Acetogenins as selective inhibitors of the human ovarian 1A9 tumor cell line.
AID380689Mutagenic activity in Salmonella Typhimurium TA98 assessed as number of revertants at 20 ug/plate in presence of Wistar rat S9 liver homogenate2000Journal of natural products, Jun, Volume: 63, Issue:6
Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (43)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (2.33)18.7374
1990's7 (16.28)18.2507
2000's25 (58.14)29.6817
2010's9 (20.93)24.3611
2020's1 (2.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.33

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 Index23.33 (24.57)
Research Supply Index3.83 (2.92)
Research Growth Index5.52 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.33)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (6.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other42 (93.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
dimethyl sulfoxide
Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.		2.0610sulfoxide;
volatile organic compound		alkylating agent;
antidote;
Escherichia coli metabolite;
geroprotector;
MRI contrast agent;
non-narcotic analgesic;
polar aprotic solvent;
radical scavenger
benzyl benzoate
benzyl benzoate: structure; acarosan, a moist powder composed of wetted cellulose and benzyl benzoate, is used on carpets as an acaricide. benzyl benzoate : A benzoate ester obtained by the formal condensation of benzoic acid with benzyl alcohol. It has been isolated from the plant species of the genus Polyalthia.		710benzoate ester;
benzyl ester		acaricide;
plant metabolite;
scabicide
tetraethylammonium
Tetraethylammonium: A potassium-selective ion channel blocker. (From J Gen Phys 1994;104(1):173-90)		2.0110quaternary ammonium ion
egtazic acid
Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.		2.0110diether;
tertiary amino compound;
tetracarboxylic acid		chelator
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.		2.420organic heteropentacyclic compound;
rotenones		antineoplastic agent;
metabolite;
mitochondrial NADH:ubiquinone reductase inhibitor;
phytogenic insecticide;
piscicide;
toxin
4-butyrolactone
4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.		2.4120butan-4-olidemetabolite;
neurotoxin
vinblastine
[no description available]		2.420
ruthenium
Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.		2.0310iron group element atom;
platinum group metal atom
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).		2.0110taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
paxilline
paxilline: structure given in first source; RN given refers to (2R-(2alpha,4bbeta,6aalpha,12bbeta,12calpha,14abeta))-isomer. paxilline : An indole diterpene alkaloid with formula C27H33NO4 isolated from Penicillium paxilli. It is a potent inhibitor of large conductance Ca2(+)- and voltage-activated K(+) (BK)-type channels.		2.0110diterpene alkaloid;
enone;
organic heterohexacyclic compound;
terpenoid indole alkaloid;
tertiary alcohol		anticonvulsant;
Aspergillus metabolite;
EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor;
genotoxin;
geroprotector;
mycotoxin;
Penicillium metabolite;
potassium channel blocker
desacetyluvaricin
desacetyluvaricin: isolated from Uvaria accuminata; structure given in first source		210
4-hydroxy-25-desoxyneorollinicin
4-hydroxy-25-desoxyneorollinicin: isol from Rollina papilionella; structure given in first source		3.1150
hydroxyl radical
Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.		2.0210oxygen hydride;
oxygen radical;
reactive oxygen species
annonacin
annonacin: linear polyketide isolated from extracts of the stembark of Annona densicoma; structure given in first source		7.4620
acetogenins
Acetogenins: Polyketides of up to a few dozen carbons in length, formed by chain extension of multiple PROPIONATES and oxygenated to form tetrahydrofuran and lactone rings along the length of the chain. They are found in ANNONACEAE and other PLANTS. Related compounds cyclize to MACROLIDES.		3.5580
cefadroxil
uvaricin: isolated from Uvaria accuminata; structure given in first source		1.9810polyketide
zeatin
Zeatin: An aminopurine factor in plant extracts that induces cell division. (Grant & Hackh's Chemical Dict, 5th ed)		2.0110zeatinplant metabolite
chalcone
trans-chalcone : The trans-isomer of chalcone.		3.110chalconeEC 3.2.1.1 (alpha-amylase) inhibitor
licochalcone a
licochalcone A: has both anti-inflammatory and antineoplastic activities; structure given in first source; isolated from root of Glycyrrhiza inflata; RN given refers to (E)-isomer		3.110chalcones
piericidin a
piericidin A: pyridine-substituted fatty alcohol antibiotic; minor descriptor (75-85); on-line & Index Medicus search ANTIBIOTICS (75-85); RN given refers to (S-(R*,R*-(all-E)))-isomer. piericidin A : A member of the class of monohydroxypyridines that acts as an irreversible mitochondrial Complex I inhibitor that strongly associates with ubiquinone binding sites in both mitochondrial and bacterial forms of NADH:ubiquinone oxidoreductase		1.9810aromatic ether;
methylpyridines;
monohydroxypyridine;
secondary allylic alcohol		antimicrobial agent;
bacterial metabolite;
EC 1.6.5.3 [NADH:ubiquinone reductase (H(+)-translocating)] inhibitor;
mitochondrial respiratory-chain inhibitor
chamuvarinin
chamuvarinin: from the roots of Uvaria chamae; structure in first source		7.4320
murisolin
murisolin: structure in first source		2.0110polyketide
iberiotoxin
[no description available]		2.0110
warfarin
Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.		3.110benzenes;
hydroxycoumarin;
methyl ketone
isomurisolenin
isomurisolenin: an acetogenin from seeds of Annona reticulata;		3.110
ConditionIndicatedRelationship StrengthStudiesTrials
Cancer of Ovary
[description not available]		02.0110
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.		02.0110
Benign Neoplasms
[description not available]		02.4820
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.4820
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.0110
Experimental Neoplasms
[description not available]		02.0110
Bladder Cancer
[description not available]		07.0310
Urinary Bladder Neoplasms
Tumors or cancer of the URINARY BLADDER.		02.0310
Leukemia P388
An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.		01.9810
Leishmania Infection
[description not available]		02.9110
Leishmaniasis
A disease caused by any of a number of species of protozoa in the genus LEISHMANIA. There are four major clinical types of this infection: cutaneous (Old and New World) (LEISHMANIASIS, CUTANEOUS), diffuse cutaneous (LEISHMANIASIS, DIFFUSE CUTANEOUS), mucocutaneous (LEISHMANIASIS, MUCOCUTANEOUS), and visceral (LEISHMANIASIS, VISCERAL).		02.9110
Adenocarcinoma, Basal Cell
[description not available]		0210
Breast Cancer
[description not available]		0210
Adenocarcinoma
A malignant epithelial tumor with a glandular organization.		0710
Breast Neoplasms
Tumors or cancer of the human BREAST.		0210