inuviscolide

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

Description

inuviscolide: from Inula viscosa; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

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. [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]

Flora	Rank	Flora Definition	Family	Family Definition
Inula	genus	A plant genus of the family ASTERACEAE. Members contain INULIN, alantol, helenin, alantic acid, and acrid resin.[MeSH]	Asteraceae	A 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 hupehensis	species	[no description available]	Asteraceae	A 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 Source	ID
PubMed CID	176489
CHEMBL ID	521960
CHEBI ID	69345
SCHEMBL ID	12476693
MeSH ID	M0429837

Synonyms (11)

Synonym
CHEMBL521960
chebi:69345 ,
inuviscolide
63109-30-8
(3ar,4ar,5r,7as,9as)-5-hydroxy-5-methyl-3,8-dimethylidenedecahydroazuleno[6,5-b]furan-2(3h)-one
SCHEMBL12476693
Q27137686
DTXSID80979063
5-hydroxy-5-methyl-3,8-dimethylidenedecahydroazuleno[6,5-b]furan-2(3h)-one
CS-0638972
HY-N11110

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

Role	Description
anti-inflammatory agent	Any compound that has anti-inflammatory effects.
plant metabolite	Any 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)

Class	Description
gamma-lactone	A lactone having a five-membered lactone ring.
organic heterotricyclic compound	An organic tricyclic compound in which at least one of the rings of the tricyclic skeleton contains one or more heteroatoms.
sesquiterpene lactone	Any 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.
tertiary alcohol	A tertiary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has three other carbon atoms attached to it.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (6)

Assay ID	Title	Year	Journal	Article
AID626782	Antiinflammatory 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 reaction	2011	Journal of natural products, Sep-23, Volume: 74, Issue:9	Pseudoguaianolides and guaianolides from Inula hupehensis as potential anti-inflammatory agents.
AID625544	Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced NO production pretreated for 30 mins before LPS challenge measured 24 hrs after LPS challenge by Griess reaction method	2011	European journal of medicinal chemistry, Nov, Volume: 46, Issue:11	Sesquiterpene lactones from Inula falconeri, a plant endemic to the Himalayas, as potential anti-inflammatory agents.
AID379443	Antiinflammatory activity against Swiss mouse assessed as inhibition of TPA-induced edema at 0.5 mg/ear applied simultaneously with TPA measured after 4 hrs	1999	Journal of natural products, Apr, Volume: 62, Issue:4	A glycosyl analogue of diacylglycerol and other antiinflammatory constituents from Inula viscosa.
AID626783	Cytotoxicity against mouse RAW264.7 cells after 24 hrs by MTT assay	2011	Journal of natural products, Sep-23, Volume: 74, Issue:9	Pseudoguaianolides and guaianolides from Inula hupehensis as potential anti-inflammatory agents.
AID379444	Antiinflammatory activity against Swiss mouse assessed as inhibition of arachidonic acid-induced edema at 0.5 mg/ear applied 30 mins before arachidonic acid challenge measured after 1 hr	1999	Journal of natural products, Apr, Volume: 62, Issue:4	A glycosyl analogue of diacylglycerol and other antiinflammatory constituents from Inula viscosa.
AID625545	Cytotoxicity against mouse RAW264.7 cells at antiinflammatory IC50 level by MTT assay	2011	European journal of medicinal chemistry, Nov, Volume: 46, Issue:11	Sesquiterpene lactones from Inula falconeri, a plant endemic to the Himalayas, as potential anti-inflammatory agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	1 (11.11)	18.2507
2000's	3 (33.33)	29.6817
2010's	4 (44.44)	24.3611
2020's	1 (11.11)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.62

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.

Metric	This Compound (vs All)
Research Demand Index	12.62 (24.57)
Research Supply Index	2.30 (2.92)
Research Growth Index	4.92 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (12.62)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	9 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
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.	2.47	2	guanidines; one-carbon compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 1.4.3.4 (monoamine oxidase) inhibitor
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	2	1	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic
phenylbutazone Phenylbutazone: A butyl-diphenyl-pyrazolidinedione that has anti-inflammatory, antipyretic, and analgesic activities. It has been used in ANKYLOSING SPONDYLITIS; RHEUMATOID ARTHRITIS; and REACTIVE ARTHRITIS.. phenylbutazone : A member of the class of pyrazolidines that is 1,2-diphenylpyrazolidine-3,5-dione carrying a butyl group at the 4-position.	2	1	pyrazolidines	antirheumatic drug; EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor; metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug
phenidone phenidone: photographic developer; RN given refers to parent cpd; structure	2	1
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.	2.03	1	acetate 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
alantolactone alantolactone: allergenic sesquiterpene lactone; crystalline mixture of alantolactones from group of sesquiterpenes; structure. alantolactone : A sesquiterpene lactone that is 3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2-one bearing two methyl substituents at positions 5 and 8a as well as a methylidene substituent at position 3.	2.06	1	naphthofuran; olefinic compound; sesquiterpene lactone	antineoplastic agent; apoptosis inducer; plant metabolite
tomentosin tomentosin: isolated from fresh Inula viscosa (Asteraceae) flowers; structure in first source	2.46	2	sesquiterpene lactone
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.	2.48	2	cyclic ketone; gamma-lactone; organic heterotricyclic compound; pseudoguaianolide	anti-inflammatory agent; metabolite; plant metabolite
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.	2.47	2	acetate ester; cyclic ketone; gamma-lactone; organic heterotricyclic compound; sesquiterpene lactone	anti-inflammatory agent; antineoplastic agent; metabolite; NF-kappaB inhibitor; plant metabolite
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	2.1	1
aromaticin [no description available]	2.06	1	cyclic ketone; gamma-lactone; organic heterotricyclic compound; sesquiterpene lactone	anti-inflammatory agent; metabolite; plant metabolite
sesquiterpenes [no description available]	3.32	6
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.	2.06	1	acetate ester; cyclic ketone; gamma-lactone; organic heterotricyclic compound; sesquiterpene lactone	antineoplastic agent; apoptosis inducer; immunomodulator; plant metabolite
leukotriene b4 Leukotriene B4: The major metabolite in neutrophil polymorphonuclear leukocytes. It stimulates polymorphonuclear cell function (degranulation, formation of oxygen-centered free radicals, arachidonic acid release, and metabolism). (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene B4 : A leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway.	2	1	dihydroxy monocarboxylic acid; hydroxy polyunsaturated fatty acid; leukotriene; long-chain fatty acid	human metabolite; mouse metabolite; plant metabolite; vasoconstrictor agent
kaempferol-7-methyl ether rhamnocitrin : A monomethoxyflavone that is the 7-methyl ether derivative of kaempferol.	2	1	flavonols; monomethoxyflavone; trihydroxyflavone	plant metabolite
ilicic acid ilicic acid: from Inula viscosa; structure in first source	2.41	2	eudesmane sesquiterpenoid
concanavalin a Concanavalin A: A MANNOSE/GLUCOSE binding lectin isolated from the jack bean (Canavalia ensiformis). It is a potent mitogen used to stimulate cell proliferation in lymphocytes, primarily T-lymphocyte, cultures.	2.11	1

Condition	Relationship Strength	Studies
Chronic Illness [description not available]	2	1
Anasarca [description not available]	2	1
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	2	1
Dermatitis Any inflammation of the skin.	2.42	2
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	2	1
Innate Inflammatory Response [description not available]	2.44	2
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	2.44	2
Malignant Melanoma [description not available]	2.04	1
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)	2.04	1

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