Compounds > aromaticin
Page last updated: 2024-12-08

aromaticin

FloraRankFlora DefinitionFamilyFamily Definition
InulagenusA plant genus of the family ASTERACEAE. Members contain INULIN, alantol, helenin, alantic acid, and acrid resin.[MeSH]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]
Inula hupehensisspecies[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 CID282529
CHEMBL ID494255
CHEBI ID69335

Synonyms (18)

Synonym
nsc136049
nsc-136049
C09300
(3as,5r,5ar,8as,9ar)-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
azuleno[6,5-b]furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4a,8-dimethyl-3-methylene-, (3ar,4as,7ar,8r,9as)-
MLS000728520 ,
smr000445634
(3ar,4as,7ar,8r,9as)-4a,8-dimethyl-3-methylidene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
chebi:69335 ,
CHEMBL494255
(3as,5r,5ar,8as,9ar)-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
NCGC00247557-01
HMS2222L04 ,
(3ar-(3aalpha,4abeta,7aalpha,8alpha,9abeta))-4a,8-dimethyl-3-methylene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno(6,5-b)furan-2,5-dione
bdbm43483
(3as,5r,5ar,8as,9ar)-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-quinone
cid_282529
Q27104970
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
anti-inflammatory agentAny compound that has anti-inflammatory effects.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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 (4)

ClassDescription
gamma-lactoneA lactone having a five-membered lactone ring.
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.
cyclic ketone
organic heterotricyclic compoundAn organic tricyclic compound in which at least one of the rings of the tricyclic skeleton contains one or more heteroatoms.
[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 (26)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
glp-1 receptor, partialHomo sapiens (human)Potency10.00000.01846.806014.1254AID624417
ATAD5 protein, partialHomo sapiens (human)Potency18.14520.004110.890331.5287AID504466; AID504467
USP1 protein, partialHomo sapiens (human)Potency35.48130.031637.5844354.8130AID743255
TDP1 proteinHomo sapiens (human)Potency0.84180.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency15.95410.180013.557439.8107AID1460; AID1468
thioredoxin glutathione reductaseSchistosoma mansoniPotency35.48130.100022.9075100.0000AID485364
Smad3Homo sapiens (human)Potency4.46680.00527.809829.0929AID588855
67.9K proteinVaccinia virusPotency6.11930.00018.4406100.0000AID720579; AID720580
IDH1Homo sapiens (human)Potency12.99530.005210.865235.4813AID686970
NPC intracellular cholesterol transporter 1 precursorHomo sapiens (human)Potency3.54810.01262.451825.0177AID485313
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency20.59620.00419.984825.9290AID504444
parathyroid hormone/parathyroid hormone-related peptide receptor precursorHomo sapiens (human)Potency70.79463.548119.542744.6684AID743266
huntingtin isoform 2Homo sapiens (human)Potency5.62340.000618.41981,122.0200AID1688
ras-related protein Rab-9AHomo sapiens (human)Potency2.51190.00022.621531.4954AID485297
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency17.78280.050127.073689.1251AID588590
urokinase-type plasminogen activator precursorMus musculus (house mouse)Potency12.58930.15855.287912.5893AID540303
plasminogen precursorMus musculus (house mouse)Potency12.58930.15855.287912.5893AID540303
urokinase plasminogen activator surface receptor precursorMus musculus (house mouse)Potency12.58930.15855.287912.5893AID540303
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency8.15480.00798.23321,122.0200AID2546; AID2551
gemininHomo sapiens (human)Potency2.18370.004611.374133.4983AID624296; AID624297
DNA dC->dU-editing enzyme APOBEC-3G isoform 1Homo sapiens (human)Potency3.16230.058010.694926.6086AID602310
[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)5.71000.16005.404910.0000AID504313
DNA damage-inducible transcript 3 proteinMus musculus (house mouse)IC50 (µMol)10.00000.16003.995910.0000AID504322
[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)0.59000.0800478.57894,301.1099AID1394
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]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID626782Antiinflammatory action in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide production treated 30 mins before LPS challenge measured after 24 hrs by griess reaction2011Journal of natural products, Sep-23, Volume: 74, Issue:9
Pseudoguaianolides and guaianolides from Inula hupehensis as potential anti-inflammatory agents.
AID626783Cytotoxicity against mouse RAW264.7 cells after 24 hrs by MTT assay2011Journal of natural products, Sep-23, Volume: 74, Issue:9
Pseudoguaianolides and guaianolides from Inula hupehensis as potential anti-inflammatory agents.
AID310936Cytotoxicity against human KB cells2007Bioorganic & medicinal chemistry, Apr-15, Volume: 15, Issue:8
Quantitative structure-activity relationship of sesquiterpene lactones with cytotoxic activity.
AID387024Cytotoxicity against human KB cells2008European journal of medicinal chemistry, Oct, Volume: 43, Issue:10
Use of self-organizing maps and molecular descriptors to predict the cytotoxic activity of sesquiterpene lactones.
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.
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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (40.00)29.6817
2010's2 (40.00)24.3611
2020's1 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 91.51

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index91.51 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index157.97 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (91.51)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
pimagedine
pimagedine: diamine oxidase & nitric oxide synthase inhibitor; an advanced glycosylation end product inhibitor; used in the treatment of diabetic complications; structure. aminoguanidine : A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.		2.0610guanidines;
one-carbon compound		EC 1.14.13.39 (nitric oxide synthase) inhibitor;
EC 1.4.3.4 (monoamine oxidase) inhibitor
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.		2.4420cyclic ketone;
gamma-lactone;
organic heterotricyclic compound;
secondary alcohol;
sesquiterpene lactone		anti-inflammatory agent;
antineoplastic agent;
metabolite;
plant metabolite
ambrosin
ambrosin: from Ambrosia maritime; structure		2.4420sesquiterpene lactone
Mexicanin I
[no description available]		2.4420sesquiterpene lactone
parthenolide
[no description available]		2.0410germacranolide
confertin
confertin: structure. confertin : A pseudoguaianolide that is decahydroazuleno[6,5-b]furan-2(3H)-one substituted by an oxo group at position 5, methyl groups at positions 4a and 8 and a methylidene group at position 3. It has been isolated from the aerial parts of Inula hupehensis.		2.0610cyclic ketone;
gamma-lactone;
organic heterotricyclic compound;
pseudoguaianolide		anti-inflammatory agent;
metabolite;
plant metabolite
inuviscolide
inuviscolide: from Inula viscosa; structure in first source. inuviscolide : A sesquiterpene lactone that is decahydroazuleno[6,5-b]furan-2(3H)-one substituted by a hydroxy group at position 5, a methyl group at position 5 and methylidene groups at positions 3 and 8 (the 3aR,4aR,5R,7aS,9aS stereoisomer). Isolated from the aerial parts of Inula hupehensis, it exhibits anti-inflammatory activity.		2.0610gamma-lactone;
organic heterotricyclic compound;
sesquiterpene lactone;
tertiary alcohol		anti-inflammatory agent;
plant metabolite
vernodalin
vernodalin: RN given for (3aR-(3aalpha,4alpha,5aalpha,9aalpha,9bbeta))-isomer; structure in first source		2.4420carbonyl compound
ergolide
ergolide: a potent cytotoxic sesquiterpene lactone from Inula sp.; structure given in first source. ergolide : A sesquiterpene lactone that is decahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetyloxy group at position 4. It has been isolated from the aerial parts of Inula hupehensis.		2.0610acetate ester;
cyclic ketone;
gamma-lactone;
organic heterotricyclic compound;
sesquiterpene lactone		anti-inflammatory agent;
antineoplastic agent;
metabolite;
NF-kappaB inhibitor;
plant metabolite
coronopilin
coronopilin: isolated from Ambrosia arborescens		2.4420sesquiterpene lactone
gaillardin
gaillardin: isolated from the aerial parts of Inula oculus-christi; structure in first source		2.4420sesquiterpene lactone
parthenin
parthenin: sesqiterpene lactone from Parthenium hysterophorus; structure; RN given refers to 3aS-(3aalpha,6beta,6abeta,9abeta,9balpha)-isomer		2.4420sesquiterpene lactone
vernolepin
[no description available]		2.4420delta-lactone
vernomenin
vernomenin: generic name for group of peptide lactone antibiotics from Streptomyces loidensis; structure		2.4420delta-lactone
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.		2.0610acetate ester;
cyclic ketone;
gamma-lactone;
organic heterotricyclic compound;
sesquiterpene lactone		antineoplastic agent;
apoptosis inducer;
immunomodulator;
plant metabolite
costunolide
[no description available]		2.4420germacranolide;
heterobicyclic compound		anthelminthic drug;
antiinfective agent;
antineoplastic agent;
antiparasitic agent;
antiviral drug;
metabolite
Euparotin acetate
[no description available]		2.4420sesquiterpene lactone
eupatolide
eupatolide: sesquiterpene lactone from Eupatorium formasanum HAY; structure. eupatolide : A germacranolide with formula C15H20O3, isolated from several Inula species. It exhibits anti-cancer properties.		2.0410gamma-lactone;
germacranolide;
homoallylic alcohol;
secondary alcohol		antineoplastic agent;
plant metabolite
eupatoriopicrine
[no description available]		2.0410germacranolide
ConditionIndicatedRelationship StrengthStudiesTrials
Benign Neoplasms
[description not available]		02.0310
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.		02.0310
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