Compounds > illimaquinone
Page last updated: 2024-12-06

illimaquinone

Description

Illimaquinone is a natural product isolated from the roots of the Hawaiian medicinal plant _Ochrosia grandiflora_. It exhibits a variety of biological activities, including anti-cancer, anti-inflammatory, and anti-microbial properties. Its unique structure, containing a highly substituted naphthoquinone core, has attracted significant interest from synthetic chemists, leading to several successful total syntheses. The compound's potent biological activity and challenging chemical structure make it a valuable target for drug discovery research. Illimaquinone has shown promise in inhibiting the growth of various cancer cell lines, including breast, colon, and prostate cancer cells. Its anti-inflammatory activity has been attributed to its ability to suppress the production of pro-inflammatory cytokines. Additionally, illimaquinone has demonstrated antimicrobial activity against a range of bacteria and fungi, making it a potential candidate for the development of new antibiotics. The complex and intricate structure of illimaquinone poses a significant challenge for its synthesis, making it an attractive target for synthetic chemists to develop new methodologies and strategies. The development of efficient and scalable synthetic routes to illimaquinone and its analogs is crucial for further investigation of its biological properties and potential therapeutic applications.'

illimaquinone: structure given in first source; isolated from the Red Sea sponge Smenospongia; inhibits the RNase H. activity of HIV-1 reverse transcriptase [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID72291
CHEBI ID70133
SCHEMBL ID517890
MeSH IDM0184625

Synonyms (25)

Synonym
ilimaquinone
SMP2_000173
71678-03-0
3-[[(1r,2s,4as,8as)-1,2,4a-trimethyl-5-methylene-decalin-1-yl]methyl]-2-hydroxy-5-methoxy-1,4-benzoquinone
illimaquinone
3-[[(1r,2s,4as,8as)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2h-naphthalen-1-yl]methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
chebi:70133 ,
imaquinone
5u0wan3n8q ,
2,5-cyclohexadiene-1,4-dione, 3-((decahydro-1,2,4a-trimethyl-5-methylene-1-naphthalenyl)methyl)-2-hydroxy-5-methoxy-, (1r-(1alpha,2beta,4abeta,8aalpha))-
unii-5u0wan3n8q
2,5-cyclohexadiene-1,4-dione,3-[[(1r,2s,4as,8as)-decahydro-1,2,4a-trimethyl-5-methylene-1-naphthalenyl] methyl]-2-hydroxy-5-methoxy-
FD7195
SCHEMBL517890
DTXSID90221909
ilimaquinone, (-)-
ilimaquinone [mi]
2,5-cyclohexadiene-1,4-dione, 3-(((1r,2s,4as,8as)-decahydro-1,2,4a-trimethyl-5-methylene-1-naphthalenyl)methyl)-2-hydroxy-5-methoxy-
AKOS027338228
Q27138473
HY-119500
AMY15369
CS-0068556
2-hydroxy-5-methoxy-3-(((1r,2s,4as,8as)-1,2,4a-trimethyl-5-methylenedecahydronaphthalen-1-yl)methyl)cyclohexa-2,5-diene-1,4-dione
3-[(decahydro-1beta,2beta,4alphabeta-trimethyl-5-methylene-1-naphthyl)methyl]-2-hydroxy-5-methoxybenzoquinone;imaquinone

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" This method was successfully applied in a pharmacokinetic study of ilimaquinone after oral administration in rats."( HPLC-MS/MS analysis of ilimaquinone and its application in a pharmacokinetic study in rats.
Kang, C; Kang, W; Na, M; Noh, K; Oh, S; Son, H; Song, IS, 2019)		0.51

Bioavailability

ExcerptReferenceRelevance
" Since most efforts have focused on the development of nucleoside analog inhibitors, issues regarding bioavailability and selectivity have been major challenges."( A new structural class of S-adenosylhomocysteine hydrolase inhibitors.
Chun, TG; Kim, BG; Lee, HY; Snapper, ML, 2009)		0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[role 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]

Drug Classes (2)

ClassDescription
prenylquinoneA quinone substituted by a polyprenyl-derived side-chain. Prenylquinones occur in all living cells. Due to their amphiphilic character, they are mainly located in biological membranes where they function as electron and proton carriers in the photosynthetic and respiratory electron transport chains. Some prenylquinones also perform more specialised roles sucy as antioxidants and enzyme cofactors. Prenylquinones are classified according to ring structure: the main classes are menaquinones, phylloquinones, ubiquinones and plastoquinones.
monohydroxy-1,4-benzoquinonesAny 1,4-benzoquinone carrying a single hydroxy substituent.
[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 (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
DNA polymerase betaHomo sapiens (human)IC50 (µMol)45.20001.40006.56679.0000AID333392
AdenosylhomocysteinaseHomo sapiens (human)IC50 (µMol)40.00000.00152.11118.7000AID477475
M-phase inducer phosphatase 2Homo sapiens (human)IC50 (µMol)92.00000.10002.31039.5100AID333393
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (35)

Processvia Protein(s)Taxonomy
nucleotide-excision repair, DNA gap fillingDNA polymerase betaHomo sapiens (human)
in utero embryonic developmentDNA polymerase betaHomo sapiens (human)
DNA-templated DNA replicationDNA polymerase betaHomo sapiens (human)
DNA repairDNA polymerase betaHomo sapiens (human)
base-excision repairDNA polymerase betaHomo sapiens (human)
base-excision repair, gap-fillingDNA polymerase betaHomo sapiens (human)
pyrimidine dimer repairDNA polymerase betaHomo sapiens (human)
inflammatory responseDNA polymerase betaHomo sapiens (human)
DNA damage responseDNA polymerase betaHomo sapiens (human)
salivary gland morphogenesisDNA polymerase betaHomo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damageDNA polymerase betaHomo sapiens (human)
response to gamma radiationDNA polymerase betaHomo sapiens (human)
somatic hypermutation of immunoglobulin genesDNA polymerase betaHomo sapiens (human)
response to ethanolDNA polymerase betaHomo sapiens (human)
lymph node developmentDNA polymerase betaHomo sapiens (human)
spleen developmentDNA polymerase betaHomo sapiens (human)
homeostasis of number of cellsDNA polymerase betaHomo sapiens (human)
neuron apoptotic processDNA polymerase betaHomo sapiens (human)
response to hyperoxiaDNA polymerase betaHomo sapiens (human)
immunoglobulin heavy chain V-D-J recombinationDNA polymerase betaHomo sapiens (human)
DNA biosynthetic processDNA polymerase betaHomo sapiens (human)
double-strand break repair via nonhomologous end joiningDNA polymerase betaHomo sapiens (human)
one-carbon metabolic processAdenosylhomocysteinaseHomo sapiens (human)
S-adenosylmethionine cycleAdenosylhomocysteinaseHomo sapiens (human)
G2/M transition of mitotic cell cycleM-phase inducer phosphatase 2Homo sapiens (human)
mitotic cell cycleM-phase inducer phosphatase 2Homo sapiens (human)
oocyte maturationM-phase inducer phosphatase 2Homo sapiens (human)
protein phosphorylationM-phase inducer phosphatase 2Homo sapiens (human)
female meiosis IM-phase inducer phosphatase 2Homo sapiens (human)
positive regulation of cell population proliferationM-phase inducer phosphatase 2Homo sapiens (human)
positive regulation of G2/M transition of mitotic cell cycleM-phase inducer phosphatase 2Homo sapiens (human)
positive regulation of cytokinesisM-phase inducer phosphatase 2Homo sapiens (human)
positive regulation of mitotic cell cycleM-phase inducer phosphatase 2Homo sapiens (human)
cell divisionM-phase inducer phosphatase 2Homo sapiens (human)
positive regulation of G2/MI transition of meiotic cell cycleM-phase inducer phosphatase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (14)

Processvia Protein(s)Taxonomy
damaged DNA bindingDNA polymerase betaHomo sapiens (human)
DNA-directed DNA polymerase activityDNA polymerase betaHomo sapiens (human)
DNA-(apurinic or apyrimidinic site) endonuclease activityDNA polymerase betaHomo sapiens (human)
protein bindingDNA polymerase betaHomo sapiens (human)
microtubule bindingDNA polymerase betaHomo sapiens (human)
lyase activityDNA polymerase betaHomo sapiens (human)
enzyme bindingDNA polymerase betaHomo sapiens (human)
metal ion bindingDNA polymerase betaHomo sapiens (human)
5'-deoxyribose-5-phosphate lyase activityDNA polymerase betaHomo sapiens (human)
class I DNA-(apurinic or apyrimidinic site) endonuclease activityDNA polymerase betaHomo sapiens (human)
adenosylhomocysteinase activityAdenosylhomocysteinaseHomo sapiens (human)
protein bindingAdenosylhomocysteinaseHomo sapiens (human)
phosphoprotein phosphatase activityM-phase inducer phosphatase 2Homo sapiens (human)
protein tyrosine phosphatase activityM-phase inducer phosphatase 2Homo sapiens (human)
protein bindingM-phase inducer phosphatase 2Homo sapiens (human)
protein kinase bindingM-phase inducer phosphatase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
nucleusDNA polymerase betaHomo sapiens (human)
nucleoplasmDNA polymerase betaHomo sapiens (human)
cytoplasmDNA polymerase betaHomo sapiens (human)
microtubuleDNA polymerase betaHomo sapiens (human)
spindle microtubuleDNA polymerase betaHomo sapiens (human)
protein-containing complexDNA polymerase betaHomo sapiens (human)
nucleusDNA polymerase betaHomo sapiens (human)
nucleusAdenosylhomocysteinaseHomo sapiens (human)
endoplasmic reticulumAdenosylhomocysteinaseHomo sapiens (human)
cytosolAdenosylhomocysteinaseHomo sapiens (human)
melanosomeAdenosylhomocysteinaseHomo sapiens (human)
extracellular exosomeAdenosylhomocysteinaseHomo sapiens (human)
cytosolAdenosylhomocysteinaseHomo sapiens (human)
spindle poleM-phase inducer phosphatase 2Homo sapiens (human)
nucleoplasmM-phase inducer phosphatase 2Homo sapiens (human)
centrosomeM-phase inducer phosphatase 2Homo sapiens (human)
cytosolM-phase inducer phosphatase 2Homo sapiens (human)
nucleusM-phase inducer phosphatase 2Homo sapiens (human)
cytoplasmM-phase inducer phosphatase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (46)

Assay IDTitleYearJournalArticle
AID359617Inhibition of bee venom PLA21992Journal of natural products, Dec, Volume: 55, Issue:12
Phospholipase A2 inhibitors from marine organisms.
AID462418Golgi-disturbing activity in golgi apparatus of rat NRK cells assessed as golgi fragmentation after 60 mins by Hoechst 3342 staining-based immunofluorescence microscopy2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Chemical biology studies on norrisolide.
AID568751Cytotoxicity against human HT-29 cells after 48 hrs by SRB assay2011Journal of natural products, Jan-28, Volume: 74, Issue:1
Sesquiterpene benzoxazoles and sesquiterpene quinones from the marine sponge Dactylospongia elegans.
AID1647967Antiproliferative activity against human PC3 cells assessed as reduction in cell viability by MTT assay2020Journal of natural products, 02-28, Volume: 83, Issue:2
Quintaquinone, a Merosesquiterpene from the Yellow Sponge
AID377195Inhibition of thymidine kinase at 1 ug/uL2000Journal of natural products, Aug, Volume: 63, Issue:8
Pelorol from the tropical marine sponge Dactylospongia elegans.
AID402134Cytotoxicity against human KB16 cells after 3 days by MTT assay1997Journal of natural products, Feb, Volume: 60, Issue:2
New sesquiterpene hydroquinones from a Taiwanese marine sponge Polyfibrospongia australis.
AID1439821Antiinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-stimulated nitric oxide production at 40 uM by Griess assay relative to control2017Bioorganic & medicinal chemistry letters, 04-01, Volume: 27, Issue:7
Sesquiterpene derivatives from marine sponge Smenospongia cerebriformis and their anti-inflammatory activity.
AID333108Inhibition of human MDA-MB-231 cells invasion at <50 ug/mL by Matrigel cell invasion assay2004Journal of natural products, Aug, Volume: 67, Issue:8
Strongylophorine-26, a new meroditerpenoid isolated from the marine sponge Petrosia (Strongylophora) corticata that exhibits anti-invasion activity.
AID1467592Cytotoxicity against human MCF7 cells assessed as decrease in cell viability after 72 hrs by WST8 assay2017Bioorganic & medicinal chemistry letters, 07-15, Volume: 27, Issue:14
New merosesquiterpenes from a Vietnamese marine sponge of Spongia sp. and their biological activities.
AID568752Cytotoxicity against human CHOK1 cells after 48 hrs by SRB assay2011Journal of natural products, Jan-28, Volume: 74, Issue:1
Sesquiterpene benzoxazoles and sesquiterpene quinones from the marine sponge Dactylospongia elegans.
AID377196Antitrypanosomal activity against Trypanosoma rhodesiense2000Journal of natural products, Aug, Volume: 63, Issue:8
Pelorol from the tropical marine sponge Dactylospongia elegans.
AID1439822Antiinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-stimulated nitric oxide production by Griess assay2017Bioorganic & medicinal chemistry letters, 04-01, Volume: 27, Issue:7
Sesquiterpene derivatives from marine sponge Smenospongia cerebriformis and their anti-inflammatory activity.
AID1178613Antiproliferative activity against human DU145 cells assessed as growth inhibition under hypoxic condition at 1 to 30 uM after 24 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Jul-15, Volume: 24, Issue:14
Marine spongian sesquiterpene phenols, dictyoceratin-C and smenospondiol, display hypoxia-selective growth inhibition against cancer cells.
AID1467595Antibacterial activity against Bacillus subtilis NBRC 13719 after 12 hrs by MTT assay2017Bioorganic & medicinal chemistry letters, 07-15, Volume: 27, Issue:14
New merosesquiterpenes from a Vietnamese marine sponge of Spongia sp. and their biological activities.
AID1467596Antibacterial activity against Staphylococcus aureus NBRC 100910 after 12 hrs by MTT assay2017Bioorganic & medicinal chemistry letters, 07-15, Volume: 27, Issue:14
New merosesquiterpenes from a Vietnamese marine sponge of Spongia sp. and their biological activities.
AID477475Inhibition of S-adenosyl-L-homocysteine hydrolase after 10 mins by scintillation counting2009Bioorganic & medicinal chemistry, Sep-15, Volume: 17, Issue:18
A new structural class of S-adenosylhomocysteine hydrolase inhibitors.
AID462413Golgi-disturbing activity in golgi apparatus of rat NRK cells assessed as complete golgi vesiculation without fusion with endoplasmic reticulum at 30 uM after 60 mins by Hoechst 3342 staining-based immunofluorescence microscopy2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Chemical biology studies on norrisolide.
AID751051Cytotoxicity against human T47D cells assessed as growth inhibition at 3 to 30 uM after 48 hrs by SRB assay2013Journal of natural products, Jun-28, Volume: 76, Issue:6
Inducers of hypoxic response: marine sesquiterpene quinones activate HIF-1.
AID1467593Antibacterial activity against Escherichia coli NBRC 102203 after 12 hrs by MTT assay2017Bioorganic & medicinal chemistry letters, 07-15, Volume: 27, Issue:14
New merosesquiterpenes from a Vietnamese marine sponge of Spongia sp. and their biological activities.
AID568750Cytotoxicity against human H460 cells after 48 hrs by SRB assay2011Journal of natural products, Jan-28, Volume: 74, Issue:1
Sesquiterpene benzoxazoles and sesquiterpene quinones from the marine sponge Dactylospongia elegans.
AID328641Antidepressant like activity in ip dosed Swiss Webster mouse assessed as reduction of immobility time by forced-swim test2008Journal of natural products, Feb, Volume: 71, Issue:2
Secondary metabolites from three Florida sponges with antidepressant activity.
AID333393Inhibition of GST-fused human recombinant Cdc25B2 (275-539) catalytic domain2004Journal of natural products, Oct, Volume: 67, Issue:10
Marine sesquiterpenoids that inhibit the lyase activity of DNA polymerase beta.
AID333392Inhibition of DNA polymerase beta lyase activity2004Journal of natural products, Oct, Volume: 67, Issue:10
Marine sesquiterpenoids that inhibit the lyase activity of DNA polymerase beta.
AID1647966Inhibition of steroid 5-alpha-reductase in human LNCAP cells assessed as reduction in 5- dihydrotestosterone formation at 100 uM incubated for 60 mins by LC-MS analysis relative to control2020Journal of natural products, 02-28, Volume: 83, Issue:2
Quintaquinone, a Merosesquiterpene from the Yellow Sponge
AID568748Cytotoxicity against human SF268 cells after 48 hrs by SRB assay2011Journal of natural products, Jan-28, Volume: 74, Issue:1
Sesquiterpene benzoxazoles and sesquiterpene quinones from the marine sponge Dactylospongia elegans.
AID1467590Cytotoxicity against human HeLa cells assessed as decrease in cell viability after 72 hrs by WST8 assay2017Bioorganic & medicinal chemistry letters, 07-15, Volume: 27, Issue:14
New merosesquiterpenes from a Vietnamese marine sponge of Spongia sp. and their biological activities.
AID1467589Cytotoxicity against human WI38 cells assessed as decrease in cell viability after 72 hrs by WST8 assay2017Bioorganic & medicinal chemistry letters, 07-15, Volume: 27, Issue:14
New merosesquiterpenes from a Vietnamese marine sponge of Spongia sp. and their biological activities.
AID751056Activation of HIF-1 (unknown origin) transfected in human T47D cells at 10 uM after 16 hrs by luciferase reporter gene assay relative to control2013Journal of natural products, Jun-28, Volume: 76, Issue:6
Inducers of hypoxic response: marine sesquiterpene quinones activate HIF-1.
AID377198Antiplasmodial activity against Plasmodium falciparum NF542000Journal of natural products, Aug, Volume: 63, Issue:8
Pelorol from the tropical marine sponge Dactylospongia elegans.
AID1647968Antiproliferative activity against human HeLa cells assessed as reduction in cell viability after 72 hrs by sulforhodamine B assay2020Journal of natural products, 02-28, Volume: 83, Issue:2
Quintaquinone, a Merosesquiterpene from the Yellow Sponge
AID402133Cytotoxicity against mouse P388 cells after 3 days by MTT assay1997Journal of natural products, Feb, Volume: 60, Issue:2
New sesquiterpene hydroquinones from a Taiwanese marine sponge Polyfibrospongia australis.
AID402135Cytotoxicity against human A549 cells after 6 days by MTT assay1997Journal of natural products, Feb, Volume: 60, Issue:2
New sesquiterpene hydroquinones from a Taiwanese marine sponge Polyfibrospongia australis.
AID1439823Cytotoxicity against mouse BV2 cells assessed as cell viability at 40 uM relative to control2017Bioorganic & medicinal chemistry letters, 04-01, Volume: 27, Issue:7
Sesquiterpene derivatives from marine sponge Smenospongia cerebriformis and their anti-inflammatory activity.
AID751052Cytotoxicity against human T47D cells assessed as growth inhibition at 30 uM after 48 hrs by SRB assay relative to control2013Journal of natural products, Jun-28, Volume: 76, Issue:6
Inducers of hypoxic response: marine sesquiterpene quinones activate HIF-1.
AID1647969Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability after 72 hrs by sulforhodamine B assay2020Journal of natural products, 02-28, Volume: 83, Issue:2
Quintaquinone, a Merosesquiterpene from the Yellow Sponge
AID751053Activation of HIF-1 in human T47D cells assessed as increase in cellular VEGF production at 10 uM after 16 hrs by ELISA2013Journal of natural products, Jun-28, Volume: 76, Issue:6
Inducers of hypoxic response: marine sesquiterpene quinones activate HIF-1.
AID377197Antiplasmodial activity against Plasmodium falciparum K12000Journal of natural products, Aug, Volume: 63, Issue:8
Pelorol from the tropical marine sponge Dactylospongia elegans.
AID568749Cytotoxicity against human MCF7 cells after 48 hrs by SRB assay2011Journal of natural products, Jan-28, Volume: 74, Issue:1
Sesquiterpene benzoxazoles and sesquiterpene quinones from the marine sponge Dactylospongia elegans.
AID751049Activation of HIF-1 in human PC3 cells assessed as increase in VEGF production at 10 uM after 16 hrs by ELISA2013Journal of natural products, Jun-28, Volume: 76, Issue:6
Inducers of hypoxic response: marine sesquiterpene quinones activate HIF-1.
AID462416Golgi-disturbing activity in golgi apparatus of rat NRK cells assessed as golgi fragmentation after 60 mins by Hoechst 3342 staining-based immunofluorescence microscopy in presence of PKD inhibitor H892010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Chemical biology studies on norrisolide.
AID1467591Cytotoxicity against human A549 cells assessed as decrease in cell viability after 72 hrs by WST8 assay2017Bioorganic & medicinal chemistry letters, 07-15, Volume: 27, Issue:14
New merosesquiterpenes from a Vietnamese marine sponge of Spongia sp. and their biological activities.
AID751050Cytotoxicity against human MDA-MB-231 cells assessed as growth inhibition at 3 to 30 uM after 48 hrs by SRB assay2013Journal of natural products, Jun-28, Volume: 76, Issue:6
Inducers of hypoxic response: marine sesquiterpene quinones activate HIF-1.
AID333394Cytotoxicity against human A2780 cells2004Journal of natural products, Oct, Volume: 67, Issue:10
Marine sesquiterpenoids that inhibit the lyase activity of DNA polymerase beta.
AID1467594Antibacterial activity against Klebsiella pneumoniae NBRC 14940 after 12 hrs by MTT assay2017Bioorganic & medicinal chemistry letters, 07-15, Volume: 27, Issue:14
New merosesquiterpenes from a Vietnamese marine sponge of Spongia sp. and their biological activities.
AID462417Golgi-disturbing activity in golgi apparatus of rat NRK cells assessed as irreversible golgi fragmentation after 60 mins by Hoechst 3342 staining-based immunofluorescence microscopy2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Chemical biology studies on norrisolide.
AID751054Activation of HIF-1 in human T47D cells assessed as increase in secreted VEGF production at 10 uM after 16 hrs by ELISA2013Journal of natural products, Jun-28, Volume: 76, Issue:6
Inducers of hypoxic response: marine sesquiterpene quinones activate HIF-1.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (57)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's19 (33.33)18.2507
2000's17 (29.82)29.6817
2010's14 (24.56)24.3611
2020's7 (12.28)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.47

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.47 (24.57)
Research Supply Index4.08 (2.92)
Research Growth Index4.55 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.47)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (3.45%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other56 (96.55%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
1-butanol
1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.		2.0310alkyl alcohol;
primary alcohol;
short-chain primary fatty alcohol		human metabolite;
mouse metabolite;
protic solvent
1,10-phenanthroline
1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases		2.0810phenanthrolineEC 2.7.1.1 (hexokinase) inhibitor;
EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor
chloroquine
Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.		2.4520aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug
fluorouracil
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.. 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.		2.1510nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
ethidium
Ethidium: A trypanocidal agent and possible antiviral agent that is widely used in experimental cell biology and biochemistry. Ethidium has several experimentally useful properties including binding to nucleic acids, noncompetitive inhibition of nicotinic acetylcholine receptors, and fluorescence among others. It is most commonly used as the bromide.. ethidium : The fluorescent compound widely used in experimental cell biology and biochemistry to reveal double-stranded DNA and RNA.		2.4110phenanthridinesfluorochrome;
intercalator
nocodazole
[no description available]		2.4220aromatic ketone;
benzimidazoles;
carbamate ester;
thiophenes		antimitotic;
antineoplastic agent;
microtubule-destabilising agent;
tubulin modulator
ethylmaleimide
Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.		2.6830maleimidesanticoronaviral agent;
EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor;
EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor;
EC 2.7.1.1 (hexokinase) inhibitor
propranolol
Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.		2.0310naphthalenes;
propanolamine;
secondary amine		anti-arrhythmia drug;
antihypertensive agent;
anxiolytic drug;
beta-adrenergic antagonist;
environmental contaminant;
human blood serum metabolite;
vasodilator agent;
xenobiotic
kanamycin a
Kanamycin: Antibiotic complex produced by Streptomyces kanamyceticus from Japanese soil. Comprises 3 components: kanamycin A, the major component, and kanamycins B and C, the minor components.. kanamycin : Kanamycin is a naturally occurring antibiotic complex from Streptomyces kanamyceticus that consists of several components: kanamycin A, the major component (also usually designated as kanamycin), and kanamycins B, C, D and X the minor components.		2.1510kanamycinsbacterial metabolite
tyrosine
Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.		2.1310amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
proteinogenic amino acid;
tyrosine		EC 1.3.1.43 (arogenate dehydrogenase) inhibitor;
fundamental metabolite;
micronutrient;
nutraceutical
ampicillin
Ampicillin: Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.. ampicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.		2.1510beta-lactam antibiotic;
penicillin allergen;
penicillin		antibacterial drug
2-butanol
2-butanol: RN given is for parent cpd without isomeric designation. butan-2-ol : A secondary alcohol that is butane substituted by a hydroxy group at position 2.		2.0310secondary alcohol
benzoxazoles
1,3-benzoxazole : A benzoxazole in which the benzene ring is fused to a 1,3-oxazole ring across positions 4 and 5.. benzoxazole : Compounds based on a fused 1,2- or 1,3-oxazole and benzene bicyclic ring skeleton.		2.06101,3-benzoxazoles;
mancude organic heterobicyclic parent
cyclopentane
Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.		2.6830cycloalkane;
cyclopentanes;
volatile organic compound		non-polar solvent
melarsoprol
Melarsoprol: Arsenical used in trypanosomiases. It may cause fatal encephalopathy and other undesirable side effects.		210triazines
acetylcysteine
N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.		2.0510acetylcysteine;
L-cysteine derivative;
N-acetyl-L-amino acid		antidote to paracetamol poisoning;
antiinfective agent;
antioxidant;
antiviral drug;
ferroptosis inhibitor;
geroprotector;
human metabolite;
mucolytic;
radical scavenger;
vulnerary
deoxyuridine
[no description available]		2.0210pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
tetradecanoylphorbol acetate
Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.		2.0210acetate ester;
diester;
phorbol ester;
tertiary alpha-hydroxy ketone;
tetradecanoate ester		antineoplastic agent;
apoptosis inducer;
carcinogenic agent;
mitogen;
plant metabolite;
protein kinase C agonist;
reactive oxygen species generator
transferrin
Transferrin: An iron-binding beta1-globulin that is synthesized in the LIVER and secreted into the blood. It plays a central role in the transport of IRON throughout the circulation. A variety of transferrin isoforms exist in humans, including some that are considered markers for specific disease states.		1.9910
azides
Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.		1.9910pseudohalide anionmitochondrial respiratory-chain inhibitor
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).		1.9810taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
finasteride
Finasteride: An orally active 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE inhibitor. It is used as a surgical alternative for treatment of benign PROSTATIC HYPERPLASIA.. finasteride : An aza-steroid that is a synthetic drug for the treatment of benign prostatic hyperplasia.		2.25103-oxo steroid;
aza-steroid;
delta-lactam		androgen antagonist;
antihyperplasia drug;
EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor
acridine orange
Acridine Orange: A cationic cytochemical stain specific for cell nuclei, especially DNA. It is used as a supravital stain and in fluorescence cytochemistry. It may cause mutations in microorganisms.. acridine orange : Fluorescent dye useful for cell cycle determination. It is cell-permeable, and interacts with DNA and RNA by intercalation or electrostatic attractions respectively.. acridine orange free base : A member of the class of aminoacridines that is acridine carrying two dimethylamino substituents at positions 3 and 6. The hydrochloride salt is the fluorescent dye 'acridine orange', used for cell cycle determination.		2.4110aminoacridines;
aromatic amine;
tertiary amino compound		fluorochrome;
histological dye
avarol
avarol: RN given refers to parent cpd; extract from Dysidea avara(sea sponge)		2.0110
avarone
avarone: antileukemic agent; isolated from Dysidea avara		2.0110
neplanocin a
neplanocin A: neplanocins are antitumor antibiotics & carbocyclic analogs of purine nucleosides from Ampullarilla regularis A11079; see also neplanocin B, neplanocin C, neplanocin D & neplanocin F; structure in first source; a potent inhibitor of S-adenosylhomocysteine hydrolase		2.0510
5'-noraristeromycin
5'-noraristeromycin: structure given in first source		2.0510
omega-n-methylarginine
omega-N-Methylarginine: A competitive inhibitor of nitric oxide synthetase.. N(omega)-methyl-L-arginine : A L-arginine derivative with a N(omega)-methyl substituent.		2.1510amino acid zwitterion;
arginine derivative;
guanidines;
L-arginine derivative;
non-proteinogenic L-alpha-amino acid
eritadenine
eritadenine: isolated from Lentinula edodes (Shiitake mushroom); inhibits S-adenosyl-L-homocysteine hydrolase activity		2.0510
chromomycin a2
chromomycin A2: has antineoplastic activity; structure in first source		2.1310
leupeptins
Leupeptins: A group of acylated oligopeptides produced by Actinomycetes that function as protease inhibitors. They have been known to inhibit to varying degrees trypsin, plasmin, KALLIKREINS, papain and the cathepsins.		2.0510
s-adenosylhomocysteine
S-Adenosylhomocysteine: 5'-S-(3-Amino-3-carboxypropyl)-5'-thioadenosine. Formed from S-adenosylmethionine after transmethylation reactions.. S-adenosyl-L-homocysteine : An organic sulfide that is the S-adenosyl derivative of L-homocysteine.		2.4220adenosines;
amino acid zwitterion;
homocysteine derivative;
homocysteines;
organic sulfide		cofactor;
EC 2.1.1.72 [site-specific DNA-methyltransferase (adenine-specific)] inhibitor;
EC 2.1.1.79 (cyclopropane-fatty-acyl-phospholipid synthase) inhibitor;
epitope;
fundamental metabolite
acetylleucyl-leucyl-norleucinal
acetylleucyl-leucyl-norleucinal: a proteasome inhibitor. acetylleucyl-leucyl-norleucinal : A tripeptide composed of N-acetylleucyl, leucyl and norleucinal residues joined in sequence.		2.0510aldehyde;
tripeptide		cysteine protease inhibitor
sesquiterpenes
[no description available]		4.78290
smenospongine
smenospongine: a spongean (Dactylospongia elegans) sesquiterpene aminoquinone, induces erythroid differentiation in K562 cells; structure in first source		2.5220
brefeldin a
[no description available]		3.5180macrolide antibioticPenicillium metabolite
luffariellolide
luffariellolide: structure given in first source; a partially reversible phospholipase A2 inhibitor; a major metabolite of the sponge Luffariella; do not confuse with luffolide, a minor metabolite of the same species		3.0810diterpene lactone
psammaplin a
psammaplin A: isolated from marine sponges Poecillastra and Jaspis; structure in second source		2.1310
bafilomycin a1
bafilomycin A1: from Streptomyces griseus; structure given in first source. bafilomycin A1 : The most used of the bafilomycins, a family of toxic macrolide antibiotics derived from Streptomyces griseus.		1.9910cyclic hemiketal;
macrolide antibiotic;
oxanes		apoptosis inducer;
autophagy inhibitor;
bacterial metabolite;
EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor;
EC 3.6.3.14 (H(+)-transporting two-sector ATPase) inhibitor;
ferroptosis inhibitor;
fungicide;
potassium ionophore;
toxin
manoalide
manoalide: phospholipase A2 inhibitor; sesterterpene from marine sponge L. variabilis; structure given in first source. manoalide : A sesterterpenoid isolated from the marine sponge Luffariella variabilis and which has been shown to exhibit inhibitory activity towards phospholipase A2.		3.0810butenolide;
lactol;
sesterterpenoid		EC 3.1.1.4 (phospholipase A2) inhibitor;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
metabolite
2-(4-amylcinnamoyl)amino-4-chlorobenzoic acid
2-(4-amylcinnamoyl)amino-4-chlorobenzoic acid: phospholipase A2 inhibitor		210
lactacystin
[no description available]		2.0510lactam;
S-substituted L-cysteine
motuporamine c
motuporamine C: structure in first source		2.0210
bolinaquinone
bolinaquinone: a marine sesquiterpenoid from sponge Dysidea sp. with anti-inflammatory activity; structure in first source		2.110
pelorol
pelorol: from the marine sponge Dactylospongia elegans & Petrosaspongia metachromia; structure in first source		2.7830
norrisolide
norrisolide: structure in first source		3.5120
acid phosphatase
Acid Phosphatase: An enzyme that catalyzes the conversion of an orthophosphoric monoester and water to an alcohol and orthophosphate. EC 3.1.3.2.		1.9910
dictyoceratin-c
dictyoceratin-C: from the marine species Spongia sp.; structure in first source		2.7630
scalaradial
scalaradial: RN refers to the (5alpha,12alpha,17abeta)-isomer; a marine natural product isolated from the sponge Cacospongia sp.; structure given in first source. scalaradial : A scalarane sesterterpenoid with formula C27H40O4. It is a natural product found in the marine sponges Spongia officinalis and Cacospongia mollior, and exhibits anti-inflammatory activity.		3.0810acetate ester;
carbotetracyclic compound;
dialdehyde;
enal;
scalarane sesterterpenoid		animal metabolite;
anti-inflammatory agent;
apoptosis inducer;
EC 3.1.1.4 (phospholipase A2) inhibitor;
marine metabolite;
TRP channel blocker
s-adenosylmethionine
(R)-S-adenosyl-L-methionine : An S-adenosyl-L-methionine that has R-configuration.. S-adenosyl-L-methionine zwitterion : A zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group.. (R)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has R-configuration; major species at pH 7.3.. (S)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has S-configuration; major species at pH 7.3.. S-adenosyl-L-methionine : A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.		210organic cation;
sulfonium compound		coenzyme;
cofactor;
human metabolite;
micronutrient;
Mycoplasma genitalium metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
[no description available]		2.0210BODIPY compound
elafin
Elafin: A secretory proteinase inhibitory protein that was initially purified from human SKIN. It is found in a variety mucosal secretions and is present at high levels in SPUTUM. Elafin may play a role in the innate immunity (IMMUNITY, INNATE) response of the LUNG.		2.0310
chlortetracycline
Chlortetracycline: A TETRACYCLINE with a 7-chloro substitution.. chlortetracycline : A member of the class of tetracyclines with formula C22H23ClN2O8 isolated from Streptomyces aureofaciens.		2.1510
guanosine diphosphate
Guanosine Diphosphate: A guanine nucleotide containing two phosphate groups esterified to the sugar moiety.		1.9910guanosine 5'-phosphate;
purine ribonucleoside 5'-diphosphate		Escherichia coli metabolite;
mouse metabolite;
uncoupling protein inhibitor
guanosine triphosphate
Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.		1.9910guanosine 5'-phosphate;
purine ribonucleoside 5'-triphosphate		Escherichia coli metabolite;
mouse metabolite;
uncoupling protein inhibitor
guanosine 5'-o-(3-thiotriphosphate)
Guanosine 5'-O-(3-Thiotriphosphate): Guanosine 5'-(trihydrogen diphosphate), monoanhydride with phosphorothioic acid. A stable GTP analog which enjoys a variety of physiological actions such as stimulation of guanine nucleotide-binding proteins, phosphoinositide hydrolysis, cyclic AMP accumulation, and activation of specific proto-oncogenes.		1.9910nucleoside triphosphate analogue
aplysinopsin
aplysinopsin: antineoplastic tryptophan deriv from Verongia spengetii (marine sponge); structure		2.0410
ConditionIndicatedRelationship StrengthStudiesTrials
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.520
Anoxemia
[description not available]		02.110
Benign Neoplasms
[description not available]		02.110
Hypoxia
Sub-optimal OXYGEN levels in the ambient air of living organisms.		02.110
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.		02.110
Malignant Melanoma
[description not available]		02.4110
Melanoma
A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)		02.4110
Colorectal Cancer
[description not available]		02.4110
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.		02.4110
Choroid Neovascularization
[description not available]		02.2510
Age-Related Macular Degeneration
[description not available]		02.2510
Neovascularization, Optic Disc
[description not available]		02.2510
Macular Degeneration
Degenerative changes in the RETINA usually of older adults which results in a loss of vision in the center of the visual field (the MACULA LUTEA) because of damage to the retina. It occurs in dry and wet forms.		02.2510
Retinal Neovascularization
Formation of new blood vessels originating from the retinal veins and extending along the inner (vitreal) surface of the retina.		02.2510
Carcinoma, Lewis Lung
A carcinoma discovered by Dr. Margaret R. Lewis of the Wistar Institute in 1951. This tumor originated spontaneously as a carcinoma of the lung of a C57BL mouse. The tumor does not appear to be grossly hemorrhagic and the majority of the tumor tissue is a semifirm homogeneous mass. (From Cancer Chemother Rep 2 1972 Nov;(3)1:325) It is also called 3LL and LLC and is used as a transplantable malignancy.		02.2510
Breast Cancer
[description not available]		02.3110
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.3110
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)		02.2110
Kahler Disease
[description not available]		02.110
Multiple Myeloma
A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.		02.110
Cancer of Colon
[description not available]		02.5120
Colonic Neoplasms
Tumors or cancer of the COLON.		02.5120
Animal Mammary Carcinoma
[description not available]		01.9910
HIV
Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.		01.9710
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