Compounds > eleutherin
Page last updated: 2024-12-05

eleutherin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Eleutherin is a natural product with a complex structure consisting of a benzophenone core linked to a cyclohexenone ring. It is isolated from the roots of the plant *Eleutherine bulbosa* (Iridaceae). Eleutherin exhibits various biological activities, including antimicrobial, anti-inflammatory, and anticancer properties. Its potential as a drug candidate has led to research focusing on its synthesis, structure-activity relationships, and mechanisms of action. Studies have explored its ability to inhibit the growth of various cancer cell lines, including leukemia, breast cancer, and melanoma. Additionally, its anti-inflammatory properties have been investigated in relation to its ability to suppress inflammatory cytokines. The compound's unique structure and diverse biological activities make it a subject of ongoing research, aiming to develop eleutherin-based therapeutic agents for various diseases.'

eleutherin: InChIKey: IAJIIJBMBCZPSW-DTWKUNHWSA-N [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10166
CHEMBL ID594153
CHEBI ID4774
MeSH IDM0371953

Synonyms (32)

Synonym
1h-naphtho(2,3-c)pyran-5,10-dione, 3,4-dihydro-1-beta,3-beta-dimethyl-9-methoxy-
brn 0087122
3,4-dihydro-1-beta,3-beta-dimethyl-9-methoxy-1h-naphtho(2,3-c)pyran-5,10-dione
1h-naphtho(2,3-c)pyran-5,10-dione, 3,4-dihydro-9-methoxy-1,3-dimethyl-, (1r-cis)-
eleutherin
478-36-4
(1r,3s)-9-methoxy-1,3-dimethyl-3,4-dihydro-1h-benzo[g]isochromene-5,10-dione
chebi:4774 ,
(+)-eleutherin
CHEMBL594153
5-18-03-00554 (beilstein handbook reference)
9j86wo1vyk ,
(1r,3s)-9-methoxy-1,3-dimethyl-3,4-dihydro-1h-benzo(g)isochromene-5,10-dione
unii-9j86wo1vyk
AC-34300
unii-7ftp57m80a
eleutherin, (+)-
1h-naphtho(2,3-c)pyran-5,10-dione, 3,4-dihydro-9-methoxy-1,3-dimethyl-, (1r,3s)-
1h-naphtho(2,3-c)pyran-5,10-dione, 3,4-dihydro-9-methoxy-1,3-dimethyl-, cis-(+/-)-
1h-naphtho(2,3-c)pyran-5,10-dione, 3,4-dihydro-9-methoxy-1,3-dimethyl-, cis-
eleutherin, (+/-)-
(+/-)-eleutherin
1h-naphtho(2,3-c)pyran-5,10-dione, 3,4-dihydro-9-methoxy-1,3-dimethyl-, (1r,3s)-rel-
7FTP57M80A ,
64869-73-4
1h-naphtho(2,3-c)pyran-5,10-dione, 3,4-dihydro-9-methoxy-1.beta.,3.beta.-dimethyl-
(1r,3s)-3,4-dihydro-9-methoxy-1,3-dimethyl-1h-naphtho(2,3-c)pyran-5,10-dione
DTXSID40197281
Q27106475
1h-naphtho[2,3-c]pyran-5,10-dione, 3,4-dihydro-9-methoxy-1,3-dimethyl-, (1r,3s)-
(1r,3s)-9-methoxy-1,3-dimethyl-1h,3h,4h,5h,10h-naphtho[2,3-c]pyran-5,10-dione
AKOS040760849

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
"92 µmol/kg), dosed intraperitoneally (i."( A new naphthoquinone isolated from the bulbs of Cipura paludosa and pharmacological activity of two main constituents.
Cechinel Filho, V; da Silva, GF; Delle Monache, F; Ferreira, VM; Lucena, GM; Prediger, RD; Quintão, NL; Rocha, LW; Tessele, PB, 2011)		0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
benzoisochromanequinoneA class of Streptomyces aromatic polyketide antibiotics.
p-quinonesA quinone in which the two oxo groups of the quinone are located para to each other on the 6-membered quinonoid ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID1062115Cytotoxicity against wild-type human MDA-MB-231 cells after 5 days2013Bioorganic & medicinal chemistry, Dec-15, Volume: 21, Issue:24
Synthesis and cytotoxicity of pyranonaphthoquinone natural product analogues under bioreductive conditions.
AID1062117Cytotoxicity against human MDA-MB-231 cells overexpressing NADPH-cytochrome P450 reductase after 5 days2013Bioorganic & medicinal chemistry, Dec-15, Volume: 21, Issue:24
Synthesis and cytotoxicity of pyranonaphthoquinone natural product analogues under bioreductive conditions.
AID453797Growth inhibition of Saccharomyces cerevisiae BY4741 after 24 hrs2009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Pyranonaphthoquinone derivatives of eleutherin, ventiloquinone L, thysanone and nanaomycin A possessing a diverse topoisomerase II inhibition and cytotoxicity spectrum.
AID1062116Cytotoxicity against human MDA-MB-231 cells overexpressing DT-diaphorase after 5 days2013Bioorganic & medicinal chemistry, Dec-15, Volume: 21, Issue:24
Synthesis and cytotoxicity of pyranonaphthoquinone natural product analogues under bioreductive conditions.
AID453795Induction of DNA intercalation in pRYG DNA at 100 uM by agarose gel electrophoresis2009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Pyranonaphthoquinone derivatives of eleutherin, ventiloquinone L, thysanone and nanaomycin A possessing a diverse topoisomerase II inhibition and cytotoxicity spectrum.
AID453793Inhibition of human topoisomerase 2alpha-mediated kinetoplast DNA decatenation at 100 uM2009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Pyranonaphthoquinone derivatives of eleutherin, ventiloquinone L, thysanone and nanaomycin A possessing a diverse topoisomerase II inhibition and cytotoxicity spectrum.
AID453796Inhibition of Xanthomonas vasicola XhoI assessed as pBSKS cleavage at 100 uM by endonuclease assay2009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Pyranonaphthoquinone derivatives of eleutherin, ventiloquinone L, thysanone and nanaomycin A possessing a diverse topoisomerase II inhibition and cytotoxicity spectrum.
AID453794Inhibition of human topoisomerase 2alpha-mediated relaxation of double-stranded pRYG DNA at 100 uM by agarose gel electrophoresis2009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Pyranonaphthoquinone derivatives of eleutherin, ventiloquinone L, thysanone and nanaomycin A possessing a diverse topoisomerase II inhibition and cytotoxicity spectrum.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (44.44)29.6817
2010's5 (55.56)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.81

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 Index28.81 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.92 (4.65)
Search Engine Demand Index20.59 (26.88)
Search Engine Supply Index1.50 (0.95)

This Compound (28.81)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
1,3-dipropyl-8-cyclopentylxanthine
DPCPX : An oxopurine that is 7H-xanthine substituted at positions 1 and 3 by propyl groups and at position 8 by a cyclohexyl group.		2.0810oxopurineadenosine A1 receptor antagonist;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
mercaptoethanol
Mercaptoethanol: A water-soluble thiol derived from hydrogen sulfide and ethanol. It is used as a reducing agent for disulfide bonds and to protect sulfhydryl groups from oxidation.		210alkanethiol;
primary alcohol		geroprotector
caffeine
[no description available]		2.0810purine alkaloid;
trimethylxanthine		adenosine A2A receptor antagonist;
adenosine receptor antagonist;
adjuvant;
central nervous system stimulant;
diuretic;
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor;
environmental contaminant;
food additive;
fungal metabolite;
geroprotector;
human blood serum metabolite;
mouse metabolite;
mutagen;
plant metabolite;
psychotropic drug;
ryanodine receptor agonist;
xenobiotic
ellipticine
ellipticine : A organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11.		2.0510indole alkaloid;
organic heterotetracyclic compound;
organonitrogen heterocyclic compound;
polycyclic heteroarene		antineoplastic agent;
plant metabolite
beta-lapachone
beta-lapachone: antineoplastic inhibitor of reverse transcriptase, DNA topoisomerase, and DNA polymerase. beta-lapachone : A benzochromenone that is 3,4-dihydro-2H-benzo[h]chromene-5,6-dione substituted by geminal methyl groups at position 2. Isolated from Tabebuia avellanedae, it exhibits antineoplastic and anti-inflammatory activities.		210benzochromenone;
orthoquinones		anti-inflammatory agent;
antineoplastic agent;
plant metabolite
mitomycin
Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.		2.0810mitomycinalkylating agent;
antineoplastic agent
2-naphthol
2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.		2.0410naphtholantinematodal drug;
genotoxin;
human urinary metabolite;
human xenobiotic metabolite;
mouse metabolite;
radical scavenger
etoposide
[no description available]		2.0510beta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound		antineoplastic agent;
DNA synthesis inhibitor
triazoles
Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.		2.08101,2,3-triazole
alpha-lapachone
alpha-lapachone: structure in first source		210organic heterotricyclic compound;
organooxygen compound
zm 241385
ZM 241385: a high affinity radioligand selective for the A2a adenosine receptor		2.0810diamino-1,3,5-triazine
naphthoquinones
Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.		8.5680
isoeleutherin
isoeleutherin: an immune response modulator; structure in first source		840
ventiloquinone l
ventiloquinone L: structure in first source		7.0510
ConditionIndicatedRelationship StrengthStudiesTrials
Anasarca
[description not available]		02.0610
Innate Inflammatory Response
[description not available]		02.0610
Ache
[description not available]		02.0610
Edema
Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.		02.0610
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.		02.0610
Pain
An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.		02.0610