Page last updated: 2024-11-08

angustibalin

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

Description

angustibalin: sesquiterpene lactone from Balduina angustifolia (Pursh) Robins; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
Balduinagenus[no description available]AsteraceaeA large plant family of the order Asterales, subclass Asteridae, class Magnoliopsida. The family is also known as Compositae. Flower petals are joined near the base and stamens alternate with the corolla lobes. The common name of daisy refers to several genera of this family including Aster; CHRYSANTHEMUM; RUDBECKIA; TANACETUM.[MeSH]
Balduina angustifoliaspecies[no description available]AsteraceaeA large plant family of the order Asterales, subclass Asteridae, class Magnoliopsida. The family is also known as Compositae. Flower petals are joined near the base and stamens alternate with the corolla lobes. The common name of daisy refers to several genera of this family including Aster; CHRYSANTHEMUM; RUDBECKIA; TANACETUM.[MeSH]

Cross-References

ID SourceID
PubMed CID442142
CHEMBL ID486196
CHEBI ID2723
SCHEMBL ID509228
MeSH IDM0040273

Synonyms (31)

Synonym
angustibalin
helenalin 6-acetate
C09293
10180-86-6
helanin acetate
helenalin acetate
MLS000728543 ,
smr000445656
(5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl) acetate
6-o-acetylhelenalin
CHEMBL486196
chebi:2723 ,
[(3ar,5r,5ar,8ar,9s,9ar)-5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] acetate
NCGC00247547-01
nsc 166124
azuleno(6,5-b)furan-2,5-dione, 4-(acetyloxy)-3,3a,4,4a,7a,8,9,9a-octahydro-4a,8-dimethyl-3-methylene-, (3ar-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9aalpha))-
HMS2224K23
SCHEMBL509228
bdbm43482
cid_442142
acetic acid [(3ar,5r,5ar,8ar,9s,9ar)-5,8a-dimethyl-1-methylene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] ester
acetic acid [(3ar,5r,5ar,8ar,9s,9ar)-2,8-diketo-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] ester
[(3ar,5r,5ar,8ar,9s,9ar)-5,8a-dimethyl-1-methylidene-2,8-bis(oxidanylidene)-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] ethanoate
[(3ar,5r,5ar,8ar,9s,9ar)-5,8a-dimethyl-1-methylene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] acetate
DTXSID60144191
acetylhelenalin (angustibalin)
Q27105781
HY-114519
CS-0063359
azuleno[6,5-b]furan-2,5-dione, 4-(acetyloxy)-3,3a,4,4a,7a,8,9,9a-octahydro-4a,8-dimethyl-3-methylene-, (3ar,4s,4ar,7ar,8r,9ar)-
AKOS040748522

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 (36)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
glp-1 receptor, partialHomo sapiens (human)Potency4.46680.01846.806014.1254AID624417
thioredoxin reductaseRattus norvegicus (Norway rat)Potency56.23410.100020.879379.4328AID588453
phosphopantetheinyl transferaseBacillus subtilisPotency44.66840.141337.9142100.0000AID1490
ATAD5 protein, partialHomo sapiens (human)Potency5.17140.004110.890331.5287AID504467
TDP1 proteinHomo sapiens (human)Potency0.73560.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency3.57170.180013.557439.8107AID1460; AID1468
Smad3Homo sapiens (human)Potency0.70790.00527.809829.0929AID588855
67.9K proteinVaccinia virusPotency9.58170.00018.4406100.0000AID720579; AID720580
IDH1Homo sapiens (human)Potency6.51310.005210.865235.4813AID686970
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency3.16230.035520.977089.1251AID504332
NPC intracellular cholesterol transporter 1 precursorHomo sapiens (human)Potency0.63100.01262.451825.0177AID485313
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency56.23410.354828.065989.1251AID504847
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency4.10950.00419.984825.9290AID504444
parathyroid hormone/parathyroid hormone-related peptide receptor precursorHomo sapiens (human)Potency7.07953.548119.542744.6684AID743266
huntingtin isoform 2Homo sapiens (human)Potency3.54810.000618.41981,122.0200AID1688
mitogen-activated protein kinase 1Homo sapiens (human)Potency31.62280.039816.784239.8107AID1454
ras-related protein Rab-9AHomo sapiens (human)Potency1.00000.00022.621531.4954AID485297
DNA polymerase eta isoform 1Homo sapiens (human)Potency44.66840.100028.9256213.3130AID588591
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency31.62280.050127.073689.1251AID588590
urokinase-type plasminogen activator precursorMus musculus (house mouse)Potency0.35480.15855.287912.5893AID540303
plasminogen precursorMus musculus (house mouse)Potency0.35480.15855.287912.5893AID540303
urokinase plasminogen activator surface receptor precursorMus musculus (house mouse)Potency0.35480.15855.287912.5893AID540303
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency1.25890.00798.23321,122.0200AID2546; AID2551
gemininHomo sapiens (human)Potency0.98910.004611.374133.4983AID624296; AID624297
DNA dC->dU-editing enzyme APOBEC-3G isoform 1Homo sapiens (human)Potency1.99530.058010.694926.6086AID602310
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
XBP1Homo sapiens (human)IC50 (µMol)2.20000.16005.404910.0000AID504313
type-1 angiotensin II receptorHomo sapiens (human)IC50 (µMol)21.97402.22108.230418.7980AID463214
apelin receptorHomo sapiens (human)IC50 (µMol)26.50001.75003.39008.3500AID2784
G-protein coupled receptor 55Homo sapiens (human)IC50 (µMol)4.49430.12502.58609.7907AID2013
DNA damage-inducible transcript 3 proteinMus musculus (house mouse)IC50 (µMol)2.48000.16003.995910.0000AID504322
Transcriptional activator MybGallus gallus (chicken)IC50 (µMol)0.70820.62522.76989.5499AID746038
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, BCL-2-RELATED PROTEIN A1Homo sapiens (human)EC50 (µMol)350.00008.0570121.1218338.0000AID2765
E3 ubiquitin-protein ligase Mdm2 isoform aHomo sapiens (human)EC50 (µMol)7.68000.0800478.57894,301.1099AID1394
bcl-2-like protein 11 isoform 1Homo sapiens (human)EC50 (µMol)350.00008.0570121.1218338.0000AID2765
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
PAX8Homo sapiens (human)AC500.74200.04885.435469.1700AID687027
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (3)

Processvia Protein(s)Taxonomy
regulation of gene expressionTranscriptional activator MybGallus gallus (chicken)
mitotic cell cycleTranscriptional activator MybGallus gallus (chicken)
positive regulation of transcription by RNA polymerase IITranscriptional activator MybGallus gallus (chicken)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
protein bindingTranscriptional activator MybGallus gallus (chicken)
DNA-binding transcription factor activity, RNA polymerase II-specificTranscriptional activator MybGallus gallus (chicken)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingTranscriptional activator MybGallus gallus (chicken)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
nucleoplasmTranscriptional activator MybGallus gallus (chicken)
nucleusTranscriptional activator MybGallus gallus (chicken)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1132874Antitumor activity against mouse P388 cells allografted in DBA/2 mouse assessed as survival rate at 25 mg/kg relative to control1978Journal of medicinal chemistry, Jul, Volume: 21, Issue:7
Antitumor agents. 31. Helenalin sym-dimethylethylenediamine reaction products and related derivatives.
AID746038Inhibition of c-Myb-induced mim-1 gene expression in doxycyclin-treated chicken HD11 cells after 24 hrs by GFP assay2013European journal of medicinal chemistry, May, Volume: 63Natural sesquiterpene lactones as inhibitors of Myb-dependent gene expression: structure-activity relationships.
AID409956Inhibition of mouse brain MAOB2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
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.
AID409954Inhibition of mouse brain MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID746037Cytotoxicity against chicken HD11 cells assessed as cell viability after 24 hrs by MTS assay2013European journal of medicinal chemistry, May, Volume: 63Natural sesquiterpene lactones as inhibitors of Myb-dependent gene expression: structure-activity relationships.
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.
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.
[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-19901 (14.29)18.7374
1990's1 (14.29)18.2507
2000's1 (14.29)29.6817
2010's2 (28.57)24.3611
2020's2 (28.57)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.59

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 Index12.59 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.59)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]