Compounds > 11alpha,13-dihydrohelenalin
Page last updated: 2024-11-08

11alpha,13-dihydrohelenalin

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

Cross-References

ID SourceID
PubMed CID442294
CHEMBL ID188283
CHEBI ID8268
MeSH IDM0087540

Synonyms (20)

Synonym
ambros-2-en-12-oic acid, 6-alpha,8-beta-dihydroxy-4-oxo-, 12,8-lactone, (11s)-
11alpha,13-dihydrohelenalin
dihydrohelenalin
C09531
34257-95-9
CHEMBL188283 ,
11,13-dihyrdrohelenalin
chebi:8268 ,
(1s,3ar,5r,5ar,8ar,9s,9as)-9-hydroxy-1,5,8a-trimethyl-3a,4,5,5a,9,9a-hexahydro-1h-azuleno[6,7-b]furan-2,8-dione
AC1L9CK5 ,
t7z3nv8u7t ,
ambros-2-en-12-oic acid, 6alpha,8beta-dihydroxy-4-oxo-, 12,8-lactone, (11s)-
dtxcid201012824
4-hydroxy-3,4a,8-trimethyl-3,3a,4,4a,7a,8,9,9a- octahydroazuleno[6,5-b]furan-2,5-dione
dihydrohelenalin (plenolin)
DTXSID70874699 ,
Q27108022
(3s,3as,4s,4ar,7ar,8r,9ar)-3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-3,4a,8-trimethylazuleno(6,5-b)furan-2,5-dione
ambros-2-en-12-oic acid, 6.alpha.,8.beta.-dihydroxy-4-oxo-, 12,8-lactone, (11s)-
azuleno(6,5-b)furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-3,4a,8-trimethyl-, (3s,3as,4s,4ar,7ar,8r,9ar)-

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Within a series of helenalin esters, the acetate (2) and isobutyrate (3) were more toxic than helenalin itself (1)."( Structure-cytotoxicity relationships of some helenanolide-type sesquiterpene lactones.
Beekman, AC; Konings, AW; Pras, N; Schmidt, TJ; van Uden, W; Wikström, HV; Woerdenbag, HJ, 1997)		0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
sesquiterpene lactoneAny member of a diverse class of complex, multicyclic phytochemicals showing a variety of skeleton arrangements and bioactivities, and having in common a sesquiterpenoid structure including a lactone 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]

Protein Targets (3)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Nuclear factor NF-kappa-B p105 subunitHomo sapiens (human)IC100 (µMol)200.000010.000010.000010.0000AID242927
Nuclear factor NF-kappa-B p100 subunit Homo sapiens (human)IC100 (µMol)200.000010.000010.000010.0000AID242927
Transcription factor p65Homo sapiens (human)IC100 (µMol)200.00005.00009.000010.0000AID242927; AID262798
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (107)

Processvia Protein(s)Taxonomy
negative regulation of transcription by RNA polymerase IINuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
positive regulation of transcription by RNA polymerase IINuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
cellular response to lipopolysaccharideNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
negative regulation of transcription by RNA polymerase IINuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
regulation of transcription by RNA polymerase IINuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
transcription by RNA polymerase IINuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
apoptotic processNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
inflammatory responseNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
canonical NF-kappaB signal transductionNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
JNK cascadeNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
negative regulation of gene expressionNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
positive regulation of macrophage derived foam cell differentiationNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
positive regulation of lipid storageNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
negative regulation of calcidiol 1-monooxygenase activityNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
negative regulation of vitamin D biosynthetic processNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
negative regulation of cholesterol transportNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
negative regulation of interleukin-12 productionNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
response to muscle stretchNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
non-canonical NF-kappaB signal transductionNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
negative regulation of apoptotic processNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
positive regulation of DNA-templated transcriptionNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
positive regulation of transcription by RNA polymerase IINuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
negative regulation of inflammatory responseNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
B cell receptor signaling pathwayNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
negative regulation of protein metabolic processNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
mammary gland involutionNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
positive regulation of transcription initiation by RNA polymerase IINuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
cellular response to mechanical stimulusNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
cellular response to nicotineNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
cellular response to interleukin-1Nuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
cellular response to interleukin-6Nuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
cellular response to tumor necrosis factorNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
cellular response to dsRNANuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
positive regulation of canonical Wnt signaling pathwayNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
cellular response to interleukin-17Nuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
cellular response to virusNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
antibacterial innate immune responseNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
positive regulation of hyaluronan biosynthetic processNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
cellular response to angiotensinNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
positive regulation of miRNA metabolic processNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
cellular response to stressNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
innate immune responseNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
response to cytokineNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
follicular dendritic cell differentiationNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
germinal center formationNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
regulation of DNA-templated transcriptionNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
canonical NF-kappaB signal transductionNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
extracellular matrix organizationNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
response to lipopolysaccharideNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
positive regulation of transcription by RNA polymerase IINuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
rhythmic processNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
spleen developmentNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
cellular response to stressNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
innate immune responseNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
non-canonical NF-kappaB signal transductionNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
response to cytokineNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
inflammatory responseNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
positive regulation of interleukin-1 beta productionTranscription factor p65Homo sapiens (human)
positive regulation of interleukin-6 productionTranscription factor p65Homo sapiens (human)
positive regulation of interleukin-8 productionTranscription factor p65Homo sapiens (human)
positive regulation of amyloid-beta formationTranscription factor p65Homo sapiens (human)
positive regulation of NF-kappaB transcription factor activityTranscription factor p65Homo sapiens (human)
nucleotide-binding oligomerization domain containing 2 signaling pathwayTranscription factor p65Homo sapiens (human)
negative regulation of transcription by RNA polymerase IITranscription factor p65Homo sapiens (human)
liver developmentTranscription factor p65Homo sapiens (human)
hair follicle developmentTranscription factor p65Homo sapiens (human)
defense response to tumor cellTranscription factor p65Homo sapiens (human)
response to ischemiaTranscription factor p65Homo sapiens (human)
acetaldehyde metabolic processTranscription factor p65Homo sapiens (human)
chromatin organizationTranscription factor p65Homo sapiens (human)
DNA-templated transcriptionTranscription factor p65Homo sapiens (human)
regulation of DNA-templated transcriptionTranscription factor p65Homo sapiens (human)
regulation of transcription by RNA polymerase IITranscription factor p65Homo sapiens (human)
inflammatory responseTranscription factor p65Homo sapiens (human)
cellular defense responseTranscription factor p65Homo sapiens (human)
neuropeptide signaling pathwayTranscription factor p65Homo sapiens (human)
canonical NF-kappaB signal transductionTranscription factor p65Homo sapiens (human)
positive regulation of cell population proliferationTranscription factor p65Homo sapiens (human)
response to xenobiotic stimulusTranscription factor p65Homo sapiens (human)
animal organ morphogenesisTranscription factor p65Homo sapiens (human)
response to UV-BTranscription factor p65Homo sapiens (human)
positive regulation of vascular endothelial growth factor productionTranscription factor p65Homo sapiens (human)
positive regulation of gene expressionTranscription factor p65Homo sapiens (human)
positive regulation of Schwann cell differentiationTranscription factor p65Homo sapiens (human)
negative regulation of angiogenesisTranscription factor p65Homo sapiens (human)
cytokine-mediated signaling pathwayTranscription factor p65Homo sapiens (human)
protein catabolic processTranscription factor p65Homo sapiens (human)
response to muramyl dipeptideTranscription factor p65Homo sapiens (human)
response to progesteroneTranscription factor p65Homo sapiens (human)
positive regulation of interleukin-12 productionTranscription factor p65Homo sapiens (human)
positive regulation of interleukin-6 productionTranscription factor p65Homo sapiens (human)
positive regulation of interleukin-8 productionTranscription factor p65Homo sapiens (human)
response to insulinTranscription factor p65Homo sapiens (human)
tumor necrosis factor-mediated signaling pathwayTranscription factor p65Homo sapiens (human)
negative regulation of protein sumoylationTranscription factor p65Homo sapiens (human)
response to cobalaminTranscription factor p65Homo sapiens (human)
toll-like receptor 4 signaling pathwayTranscription factor p65Homo sapiens (human)
intracellular signal transductionTranscription factor p65Homo sapiens (human)
cellular response to hepatocyte growth factor stimulusTranscription factor p65Homo sapiens (human)
response to muscle stretchTranscription factor p65Homo sapiens (human)
non-canonical NF-kappaB signal transductionTranscription factor p65Homo sapiens (human)
vascular endothelial growth factor signaling pathwayTranscription factor p65Homo sapiens (human)
prolactin signaling pathwayTranscription factor p65Homo sapiens (human)
negative regulation of protein catabolic processTranscription factor p65Homo sapiens (human)
negative regulation of apoptotic processTranscription factor p65Homo sapiens (human)
positive regulation of canonical NF-kappaB signal transductionTranscription factor p65Homo sapiens (human)
response to amino acidTranscription factor p65Homo sapiens (human)
negative regulation of DNA-templated transcriptionTranscription factor p65Homo sapiens (human)
positive regulation of DNA-templated transcriptionTranscription factor p65Homo sapiens (human)
positive regulation of transcription by RNA polymerase IITranscription factor p65Homo sapiens (human)
negative regulation of insulin receptor signaling pathwayTranscription factor p65Homo sapiens (human)
regulation of inflammatory responseTranscription factor p65Homo sapiens (human)
positive regulation of T cell receptor signaling pathwayTranscription factor p65Homo sapiens (human)
positive regulation of NF-kappaB transcription factor activityTranscription factor p65Homo sapiens (human)
response to cAMPTranscription factor p65Homo sapiens (human)
defense response to virusTranscription factor p65Homo sapiens (human)
cellular response to hydrogen peroxideTranscription factor p65Homo sapiens (human)
interleukin-1-mediated signaling pathwayTranscription factor p65Homo sapiens (human)
response to interleukin-1Transcription factor p65Homo sapiens (human)
cellular response to lipopolysaccharideTranscription factor p65Homo sapiens (human)
cellular response to lipoteichoic acidTranscription factor p65Homo sapiens (human)
cellular response to peptidoglycanTranscription factor p65Homo sapiens (human)
cellular response to nicotineTranscription factor p65Homo sapiens (human)
cellular response to interleukin-1Transcription factor p65Homo sapiens (human)
cellular response to interleukin-6Transcription factor p65Homo sapiens (human)
cellular response to tumor necrosis factorTranscription factor p65Homo sapiens (human)
postsynapse to nucleus signaling pathwayTranscription factor p65Homo sapiens (human)
antiviral innate immune responseTranscription factor p65Homo sapiens (human)
negative regulation of non-canonical NF-kappaB signal transductionTranscription factor p65Homo sapiens (human)
positive regulation of non-canonical NF-kappaB signal transductionTranscription factor p65Homo sapiens (human)
negative regulation of miRNA transcriptionTranscription factor p65Homo sapiens (human)
positive regulation of miRNA transcriptionTranscription factor p65Homo sapiens (human)
cellular response to angiotensinTranscription factor p65Homo sapiens (human)
positive regulation of leukocyte adhesion to vascular endothelial cellTranscription factor p65Homo sapiens (human)
positive regulation of miRNA metabolic processTranscription factor p65Homo sapiens (human)
negative regulation of extrinsic apoptotic signaling pathwayTranscription factor p65Homo sapiens (human)
cellular response to stressTranscription factor p65Homo sapiens (human)
response to cytokineTranscription factor p65Homo sapiens (human)
innate immune responseTranscription factor p65Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (28)

Processvia Protein(s)Taxonomy
transcription cis-regulatory region bindingNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
RNA polymerase II transcription regulatory region sequence-specific DNA bindingNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specificNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
chromatin bindingNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
DNA-binding transcription factor activityNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
transcription coregulator activityNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
protein bindingNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
identical protein bindingNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
actinin bindingNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
DNA-binding transcription factor activityNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
protein bindingNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
sequence-specific double-stranded DNA bindingNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
transcription cis-regulatory region bindingTranscription factor p65Homo sapiens (human)
RNA polymerase II transcription regulatory region sequence-specific DNA bindingTranscription factor p65Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingTranscription factor p65Homo sapiens (human)
RNA polymerase II core promoter sequence-specific DNA bindingTranscription factor p65Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificTranscription factor p65Homo sapiens (human)
transcription coactivator bindingTranscription factor p65Homo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specificTranscription factor p65Homo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificTranscription factor p65Homo sapiens (human)
DNA bindingTranscription factor p65Homo sapiens (human)
chromatin bindingTranscription factor p65Homo sapiens (human)
DNA-binding transcription factor activityTranscription factor p65Homo sapiens (human)
protein bindingTranscription factor p65Homo sapiens (human)
enzyme bindingTranscription factor p65Homo sapiens (human)
protein kinase bindingTranscription factor p65Homo sapiens (human)
chromatin DNA bindingTranscription factor p65Homo sapiens (human)
ubiquitin protein ligase bindingTranscription factor p65Homo sapiens (human)
peptide bindingTranscription factor p65Homo sapiens (human)
phosphate ion bindingTranscription factor p65Homo sapiens (human)
identical protein bindingTranscription factor p65Homo sapiens (human)
protein homodimerization activityTranscription factor p65Homo sapiens (human)
actinin bindingTranscription factor p65Homo sapiens (human)
histone deacetylase bindingTranscription factor p65Homo sapiens (human)
NF-kappaB bindingTranscription factor p65Homo sapiens (human)
ankyrin repeat bindingTranscription factor p65Homo sapiens (human)
general transcription initiation factor bindingTranscription factor p65Homo sapiens (human)
DNA-binding transcription factor bindingTranscription factor p65Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (16)

Processvia Protein(s)Taxonomy
extracellular regionNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
nucleusNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
nucleoplasmNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
cytoplasmNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
mitochondrionNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
cytosolNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
secretory granule lumenNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
specific granule lumenNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
chromatinNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
transcription regulator complexNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
I-kappaB/NF-kappaB complexNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
nucleusNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
cytoplasmNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
NF-kappaB p50/p65 complexNuclear factor NF-kappa-B p105 subunitHomo sapiens (human)
nucleusNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
nucleoplasmNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
cytoplasmNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
cytosolNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
chromatinNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
Bcl3/NF-kappaB2 complexNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
cytoplasmNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
nucleusNuclear factor NF-kappa-B p100 subunit Homo sapiens (human)
nucleolusTranscription factor p65Homo sapiens (human)
nucleusTranscription factor p65Homo sapiens (human)
glutamatergic synapseTranscription factor p65Homo sapiens (human)
nucleusTranscription factor p65Homo sapiens (human)
nucleoplasmTranscription factor p65Homo sapiens (human)
cytoplasmTranscription factor p65Homo sapiens (human)
cytosolTranscription factor p65Homo sapiens (human)
NF-kappaB p50/p65 complexTranscription factor p65Homo sapiens (human)
NF-kappaB complexTranscription factor p65Homo sapiens (human)
chromatinTranscription factor p65Homo sapiens (human)
transcription regulator complexTranscription factor p65Homo sapiens (human)
cytoplasmTranscription factor p65Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID121639In vivo antileukemic activity against P-388 lymphocytic leukemia in BDF1 male mice at 15(mg/kg)/day intraperitoneal dose expressed as T/C1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Antitumor agents. 44. Bis(helenalinyl) esters and related derivatives as novel potent antileukemic agents.
AID1132876Antitumor activity against mouse P388 cells allografted in DBA/2 mouse assessed as survival rate at 48 mg/kg relative to control1978Journal of medicinal chemistry, Jul, Volume: 21, Issue:7
Antitumor agents. 31. Helenalin sym-dimethylethylenediamine reaction products and related derivatives.
AID110390Antileukemic activity of compound against the P-388 lymphocytic leukemic BDF1 male mice at 15(mg/kg)/day, administered intraperitoneally; 11.4/9.66 (Treated/control)1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Antitumor agents. 44. Bis(helenalinyl) esters and related derivatives as novel potent antileukemic agents.
AID1149569Antitumor activity against mouse P388 cells allografted in DBA/2 mouse at 25 mg/kg/day, ip relative to control1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Antitumor agents. 21. A proposed mechanism for inhibition of cancer growth by tenulin and helenalin and related cyclopentenones.
AID1149566Antitumor activity against mouse EAC cells allografted in CF1 mouse assessed as survival at 33.3 mg/kg/day, ip after 7 days1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Antitumor agents. 21. A proposed mechanism for inhibition of cancer growth by tenulin and helenalin and related cyclopentenones.
AID1132872Cytotoxicity against human Hep2 cells assessed as growth inhibition by microtiter method1978Journal of medicinal chemistry, Jul, Volume: 21, Issue:7
Antitumor agents. 31. Helenalin sym-dimethylethylenediamine reaction products and related derivatives.
AID492467Cytotoxicity against human HepG2 cells2010Journal of natural products, Mar-26, Volume: 73, Issue:3
Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach.
AID262798Inhibition of NF-kappaB DNA binding by EMSA2006Journal of medicinal chemistry, Apr-06, Volume: 49, Issue:7
Development of a structural model for NF-kappaB inhibition of sesquiterpene lactones using self-organizing neural networks.
AID110403Antileukemic activity of compound against the P-388 lymphocytic leukemic BDF1 male mice at 25(mg/kg)/day, administered intraperitoneally; 13.3/9.66 (Treated/control)1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Antitumor agents. 44. Bis(helenalinyl) esters and related derivatives as novel potent antileukemic agents.
AID121641In vivo antileukemic activity against P-388 lymphocytic leukemia in BDF1 male mice at 25(mg/kg)/day intraperitoneal dose expressed as T/C1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Antitumor agents. 44. Bis(helenalinyl) esters and related derivatives as novel potent antileukemic agents.
AID401843Cytotoxicity against mouse cloned EN2 cells after 72 hrs by MTT assay1997Journal of natural products, Mar, Volume: 60, Issue:3
Structure-cytotoxicity relationships of some helenanolide-type sesquiterpene lactones.
AID110550Antileukemic activity of compound against the P-388 lymphocytic leukemic BDF1 male mice at 8(mg/kg)/day, administered intraperitoneally; 10.7/9.66 (Treated/control)1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Antitumor agents. 44. Bis(helenalinyl) esters and related derivatives as novel potent antileukemic agents.
AID1149568Antitumor activity against rat Walker 256 cells allografted in Sprague-Dawley rat at 2.5 mg/kg/day, ip relative to control1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Antitumor agents. 21. A proposed mechanism for inhibition of cancer growth by tenulin and helenalin and related cyclopentenones.
AID121648In vivo antileukemic activity against P-388 lymphocytic leukemia in BDF1 male mice at 8(mg/kg)/day intraperitoneal dose expressed as T/C1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Antitumor agents. 44. Bis(helenalinyl) esters and related derivatives as novel potent antileukemic agents.
AID401842Cytotoxicity against mouse cloned EN2 cells after 2 hrs by MTT assay1997Journal of natural products, Mar, Volume: 60, Issue:3
Structure-cytotoxicity relationships of some helenanolide-type sesquiterpene lactones.
AID1149570Cytotoxicity against human Hep2 cells1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Antitumor agents. 21. A proposed mechanism for inhibition of cancer growth by tenulin and helenalin and related cyclopentenones.
AID1132879Antitumor activity against rat Walker 256 cells allografted in Sprague-Dawley rat assessed as survival rate at 2.5 mg/kg relative to control1978Journal of medicinal chemistry, Jul, Volume: 21, Issue:7
Antitumor agents. 31. Helenalin sym-dimethylethylenediamine reaction products and related derivatives.
AID1149567Antitumor activity against mouse EAC cells allografted in CF1 mouse assessed as tumor growth inhibition at 33.3 mg/kg/day, ip after 7 days1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Antitumor agents. 21. A proposed mechanism for inhibition of cancer growth by tenulin and helenalin and related cyclopentenones.
AID242927Concentration required for complete inhibition of Nuclear factor kappa B DNA binding2004Journal of medicinal chemistry, Nov-18, Volume: 47, Issue:24
Quantitative structure-activity relationship of sesquiterpene lactones as inhibitors of the transcription factor NF-kappaB.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (42.86)18.7374
1990's1 (14.29)18.2507
2000's2 (28.57)29.6817
2010's1 (14.29)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.51

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

MetricThis Compound (vs All)
Research Demand Index12.51 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.51)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (14.29%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
malonic acid
malonic acid : An alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.. dicarboxylic acid : Any carboxylic acid containing two carboxy groups.		1.9610alpha,omega-dicarboxylic acidhuman metabolite
succinic acid
Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.		1.9610alpha,omega-dicarboxylic acid;
C4-dicarboxylic acid		anti-ulcer drug;
fundamental metabolite;
micronutrient;
nutraceutical;
radiation protective agent
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.		2.3620nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
colchicine
(S)-colchicine : A colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions.		3.1510alkaloid;
colchicine		anti-inflammatory agent;
gout suppressant;
mutagen
diethyl malonate
diethyl malonate: isomer of diethylmalonic acid; one of most used compounds in drug synthesis, don't confuse with ethylmalonic acid		1.9610dicarboxylic acid
podophyllotoxin
Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.		3.1510furonaphthodioxole;
lignan;
organic heterotetracyclic compound		antimitotic;
antineoplastic agent;
keratolytic drug;
microtubule-destabilising agent;
plant metabolite;
tubulin modulator
cyclopentenone
2-cyclopenten-1-one : An enone that is cyclopentanone having a C=C double bond at position 2.		1.9510alicyclic ketone;
enone		Hsp70 inducer
thiocholchicine
thiocholchicine: RN refers to (S)-isomer		3.1510
helenalin
helenalin: toxic principle of Helenium microcephalum (smallhead sneezeweed); structure. helenalin : A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer).. NF-kappaB inhibitor : An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.		4.4670cyclic ketone;
gamma-lactone;
organic heterotricyclic compound;
secondary alcohol;
sesquiterpene lactone		anti-inflammatory agent;
antineoplastic agent;
metabolite;
plant metabolite
diethyl succinate
diethyl succinate: carboxylesterase substrate		1.9610fatty acid ester
zidovudine
Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.		3.1510azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
etoposide
[no description available]		3.1510beta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound		antineoplastic agent;
DNA synthesis inhibitor
betulinic acid
[no description available]		3.1510hydroxy monocarboxylic acid;
pentacyclic triterpenoid		anti-HIV agent;
anti-inflammatory agent;
antimalarial;
antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
plant metabolite
suksdorfin
suksdorfin: from the fruit of Lomatium sukdorfi; structure given in first source		3.1510
heraclenol
heraclenol: isolated from the herb Huanghuaren		3.1510
dehydroleucodine
dehydroleucodine: has antimicrobial activity; RN given refers to (3aS-(3aalpha,9aalpha,9bbeta))-isomer		2.4320
Mexicanin I
[no description available]		2.730sesquiterpene lactone
parthenolide
[no description available]		2.0310germacranolide
npf-etoposide
NPF-etoposide: RN given refers to (5R-(5alpha,5abeta,8aalpha,9beta))-isomer; structure in first source		3.1510
gl 331
GL 331: structure in first source		3.1510
arnicolide d
arnicolide D: cytotoxic; from Centipeda minima L.; structure in first source		2.4320sesquiterpene lactone
santamarine
santamarine: sesquiterpene derivative of costunolide. santamarin : A sesquiterpene lactone of the eudesmanolide group.		2.4320sesquiterpene lactone
tenulin
tenulin: toxic constituent of Helenium amarum (bitter sneezeweed); structure		1.9510sesquiterpene lactone
angustibalin
angustibalin: sesquiterpene lactone from Balduina angustifolia (Pursh) Robins; structure		2.3720sesquiterpene lactone
bevirimat
bevirimat: an HIV inhibitor; disrupts late step in processing HIV Major Core Protein p24, preventing the capsid precursor p25 from being converted to mature capsid p24. bevirimat : A pentacyclic triterpenoid obtained by the formal condensation of 2,2-dimethylsuccinic acid with the 3-hydroxy group of betulinic acid. It is isolated from the Chinese herb Syzygium claviflorum. The first in the class of HIV-1 maturation inhibitors to be studied in humans, bevirimat was identified as a potent HIV drug candidate and several clinical trials were conducted, but development into a new drug was plagued by numerous resistance-related problems.		3.1510dicarboxylic acid monoester;
monocarboxylic acid;
pentacyclic triterpenoid		HIV-1 maturation inhibitor;
metabolite
melphalan
Melphalan: An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen.. melphalan : A phenylalanine derivative comprising L-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring.		1.9510L-phenylalanine derivative;
nitrogen mustard;
non-proteinogenic L-alpha-amino acid;
organochlorine compound		alkylating agent;
antineoplastic agent;
carcinogenic agent;
drug allergen;
immunosuppressive agent
ic9564
IC9564: betulinic acid derivative; structure in first source		3.1510
moronic acid
moronic acid: from root bark extract of Ozoroa mucronata; RN & N1 from 9th CI. moronic acid : A pentacyclic triterpenoid that is olean-18-ene substituted at position 3 by an oxo group and position 28 by a carboxy group.		3.1510pentacyclic triterpenoidanti-HIV agent;
anti-HSV-1 agent;
metabolite
mercaptopurine
Mercaptopurine: An antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia.. purine-6-thiol : A thiol that is the tautomer of mercaptopurine.. mercaptopurine : A member of the class of purines that is 6,7-dihydro-1H-purine carrying a thione group at position 6. An adenine analogue, it is used in the treatment of acute lymphocytic leukemia (ALL), chronic myeloid leukemia (CML), Crohn's disease, and ulcerative colitis.		1.9510aryl thiol;
purines;
thiocarbonyl compound		anticoronaviral agent;
antimetabolite;
antineoplastic agent
bigelovin
bigelovin: a potent cytotoxic sesquiterpene lactone from Inula sp.; structure given in first source; RN refers to (3aR-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9abeta))-isomer. bigelovin : A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetoxy group at position 4. Isolated from Inula hupehensis, it exhibits antineoplastic activity.		1.9910acetate ester;
cyclic ketone;
gamma-lactone;
organic heterotricyclic compound;
sesquiterpene lactone		antineoplastic agent;
apoptosis inducer;
immunomodulator;
plant metabolite
costunolide
[no description available]		2.0310germacranolide;
heterobicyclic compound		anthelminthic drug;
antiinfective agent;
antineoplastic agent;
antiparasitic agent;
antiviral drug;
metabolite
molephantinin
molephantinin: germacranolide from Elephantopus mollis; RN given refers to (3aR-(3aR*,4S*(E),6E,9Z,11S*,11aS*))-isomer; structure in first source		3.8230germacranolide
furanoheliangolide
furanoheliangolide: structure in first source		2.4320
daurichromenic acid
daurichromenic acid: structure in first source		3.1510
desmosdumotin c
desmosdumotin C: an antitumor agent; structure in first source		3.1510olefinic compound
tirotundin
tirotundin: structure in first source		2.0310
cumambrin b
cumambrin B: RN given for (3aR-(3aalpha,4alpha,6alpha,6aalpha,9aalpha,9bbeta))-isomer; isolated from Chrysanthemum boreale; structure in first source		2.4320
chamissonolide
chamissonolide: structure given in first source		2.4120
gomisin-g
[no description available]		3.1510
achalensolide
achalensolide: structure in first source		2.4320
centratherin
centratherin: from Eremanthus eriopus (Asteraceae); structure in first source		2.0310
ConditionIndicatedRelationship StrengthStudiesTrials
Carcinoma 256, Walker
A transplantable carcinoma of the rat that originally appeared spontaneously in the mammary gland of a pregnant albino rat, and which now resembles a carcinoma in young transplants and a sarcoma in older transplants. (Stedman, 25th ed)		02.3620
Experimental Leukemia
[description not available]		02.6530
Carcinoma, Ehrlich Tumor
A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.		02.3720
Leukemia, Lymphocytic
[description not available]		01.9510
Leukemia, Lymphoid
Leukemia associated with HYPERPLASIA of the lymphoid tissues and increased numbers of circulating malignant LYMPHOCYTES and lymphoblasts.		01.9510