obacunone profile

Obacunone is a natural product with a complex structure that has been isolated from the fruits of various plants in the Rutaceae family, such as Murraya koenigii and Citrus species. It exhibits a range of biological activities, including anti-inflammatory, antioxidant, anti-cancer, and antiviral properties. Obacunone has been shown to inhibit the production of pro-inflammatory mediators, such as nitric oxide and prostaglandins, and to scavenge free radicals, suggesting its potential as an anti-inflammatory agent. Studies have also indicated that obacunone can induce apoptosis in cancer cells and inhibit the proliferation of various cancer cell lines. The compound's antiviral activity has been attributed to its ability to interfere with viral replication. The unique structural features of obacunone, coupled with its diverse biological activities, have made it a target of ongoing research. Scientists are investigating its potential therapeutic applications, particularly in the development of novel drugs for inflammatory diseases, cancer, and viral infections. Furthermore, the complex synthesis of obacunone poses a challenge for researchers, prompting studies focused on developing efficient and sustainable synthetic routes. Understanding the biosynthesis of obacunone in plants is another area of research, aimed at optimizing its production and developing alternative sources.'

obacunone: from bark of Chinese plant Phellodendron amurense; shortens sleeping time induced in mice by alpha-chloralose-urethane [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Related Flora

Flora	Rank	Flora Definition	Family	Family Definition
Phellodendron	genus	A plant genus of the family RUTACEAE. Members contain BERBERINE, indolopyridoquinazoline and other ALKALOIDS and limonoids.[MeSH]	Rutaceae	A plant family in the order Sapindales that grows in warmer regions and has conspicuous flowers.[MeSH]

ID Source	ID
PubMed CID	119041
CHEMBL ID	404140
CHEBI ID	7713
SCHEMBL ID	564187
MeSH ID	M0184305

Synonym
obacunoic acid, eta-lactone
ai3-37934
oxireno(4,4a)-2-benzopyrano(6,5-g)(2)benzoxepin-3,5,9(3ah,4bh,6h)-trione, 1-(3-furanyl)-1,6a,7,11a,11b,12,13,13a-octahydro-4b,7,7,11a,13a-pentamethyl-, (1s,3as,4ar,4br,6ar,11ar,11br,11br,13as)-
obacunone
C08775
751-03-1
chebi:7713 ,
CHEMBL404140
MLS002473187
smr001397279
NCGC00247493-01
HMS2198M14
ccris 8657
S3784
AKOS015897086
SCHEMBL564187
AC-34270
Q-100808
obacunon
obacunone, analytical standard
casimirolide
HY-N0428
(1s,3as,4ar,4br,6ar,11ar,11br,13as)-1-(furan-3-yl)-4b,7,7,11a,13a-pentamethyl-1,6a,7,11a,11b,12,13,13a-octahydrooxepino[4',3':3,4]benzo[1,2-f]oxireno[2,3-d]isochromene-3,5,9(3ah,4bh,6h)-trione
mfcd00075888
DTXSID20996592
8-(furan-3-yl)-1,1,5a,7a,11b-pentamethyl-5b,6,7,7a,8,11b,13,13a-octahydrooxireno[4',5']pyrano[4',3':5,6]naphtho[2,1-c]oxepine-3,10,12(1h,5ah,10ah)-trione
Q27107562
CCG-269280
EX-A4868
CS-0008951
A865740
AS-56011
(1r,2r,4s,7s,8s,11r,12r,18r)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.02,4.02,8.012,18]icos-13-ene-5,15,20-trione
Z3234884793

Research Excerpts

Overview

Obacunone is a small molecule with a broad spectrum of biological activities, particularly antioxidant and anti-inflammatory effects. It is a limonoid that is predominantly found in Citrus.

Excerpt	Reference	Relevance
"Obacunone (OB) is a small molecule with a broad spectrum of biological activities, particularly antioxidant and anti-inflammatory effects. "	( Obacunone targets macrophage migration inhibitory factor (MIF) to impede osteoclastogenesis and alleviate ovariectomy-induced bone loss. Chen, K; Chen, L; He, J; Hu, S; Huang, F; Jiang, H; Jiang, M; Li, X; Lin, D; Lin, X; Liu, Q; Xu, J; Ye, T; Zeng, Y; Zheng, L, 2023)	3.8
"Obacunone is a highly oxygenated triterpenoid limonoid compound with various pharmacological properties."	( Obacunone protects retinal pigment epithelium cells from ultra-violet radiation-induced oxidative injury. Dai, CM; Huang, DR; Li, SY; Li, XF, 2021)	2.79
"Obacunone (OBA) is a highly oxygenated triterpenoid with various pharmacological activities. "	( Obacunone causes sustained expression of MKP-1 thus inactivating p38 MAPK to suppress pro-inflammatory mediators through intracellular MIF. Cai, R; Fei, Q; Gao, Y; Han, Y; Hou, R; Liu, F; Liu, H; Peng, C; Qi, Y, 2018)	3.37
"Obacunone is a limonoid that is predominantly found in Citrus. "	( Dietary obacunone supplementation stimulates muscle hypertrophy, and suppresses hyperglycemia and obesity through the TGR5 and PPARγ pathway. Horiba, T; Katsukawa, M; Mita, M; Sato, R, 2015)	2.29

Treatment

Treatment with obacunone increased apoptosis by up-regulating expression of the pro-apoptotic protein Bax. Treatment also significantly increased the weight of the gastrocnemius and quadriceps muscles.

Excerpt	Reference	Relevance
"Obacunone treatment also significantly increased the weight of the gastrocnemius and quadriceps muscles."	( Dietary obacunone supplementation stimulates muscle hypertrophy, and suppresses hyperglycemia and obesity through the TGR5 and PPARγ pathway. Horiba, T; Katsukawa, M; Mita, M; Sato, R, 2015)	1.57
"Treatment with obacunone increased apoptosis by up-regulating expression of the pro-apoptotic protein Bax and down-regulating the anti-apoptotic protein Bcl2, as well as inducing G1 cell cycle arrest."	( Obacunone exhibits anti-proliferative and anti-aromatase activity in vitro by inhibiting the p38 MAPK signaling pathway in MCF-7 human breast adenocarcinoma cells. Jayaprakasha, GK; Kim, J; Patil, BS, 2014)	2.18

Toxicity

Excerpt	Reference	Relevance
" In order to determine the toxic components, we investigated the cytotoxicity of extracts and chosen components using CCK-8 assay in HepG2 cells."	( Subchronic Toxicity Studies of Cortex Dictamni Extracts in Mice and Its Potential Hepatotoxicity Mechanisms in Vitro. Fan, Q; Wang, C; Wang, T; Wu, J; Xu, A; Zhang, J; Zhao, B, 2018)	0.48

Pharmacokinetics

The purpose of the narrative review is to systematically review relevant studies on the pharmacological effects and pharmacokinetic characteristics of obacunone. The aim is to provide researchers with the latest and useful information.

Excerpt	Reference	Relevance
" This rapid and sensitive method was fully validated and successfully applied to the pharmacokinetic study of limonin, dictamnine, obacunone and fraxinellone in the rat plasma after oral administration of Cortex Dictamni extract."	( Simultaneous determination of limonin, dictamnine, obacunone and fraxinellone in rat plasma by a validated UHPLC-MS/MS and its application to a pharmacokinetic study after oral administration of Cortex Dictamni extract. Gao, E; Qu, W; Sun, J; Wang, P; Yu, Z; Zhao, Y, 2013)	0.85
" The purpose of the narrative review is to systematically review relevant studies on the pharmacological effects and pharmacokinetic characteristics of obacunone to provide researchers with the latest and useful information."	( The pharmacological and pharmacokinetic properties of obacunone from citrus fruits: A comprehensive narrative review. Chen, X; Yang, S; Zheng, W, 2023)	1.36

Compound-Compound Interactions

Excerpt	Reference	Relevance
" Therefore, ultrafiltration liquid chromatography combined with high-speed countercurrent chromatography is not only a powerful tool for screening and isolating α-glucosidase and xanthine oxidase inhibitors in complex samples but is also a useful platform for discovering bioactive compounds for the prevention and treatment of diabetes mellitus and gout."	( Ultrafiltration liquid chromatography combined with high-speed countercurrent chromatography for screening and isolating potential α-glucosidase and xanthine oxidase inhibitors from Cortex Phellodendri. Guo, L; Li, S; Liu, C; Ma, B; Qin, Y; Ren, J; Tang, Y; Wang, J; Wang, Y; Yang, X; Zhang, Y, 2014)	0.4

Bioavailability

Excerpt	Reference	Relevance
" Pharmacokinetic studies have shown that the oral bioavailability of obacunone is low."	( The pharmacological and pharmacokinetic properties of obacunone from citrus fruits: A comprehensive narrative review. Chen, X; Yang, S; Zheng, W, 2023)	1.39

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

Class	Description
limonoid	Any triterpenoid that is highly oxygenated and has a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. The term 'limonoid' comes from limonin, the first tetranortriterpenoid obtained from citrus bitter principles.
[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	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, Beta-lactamase	Escherichia coli K-12	Potency	28.1838	0.0447	17.8581	100.0000	AID485341
ATAD5 protein, partial	Homo sapiens (human)	Potency	0.2592	0.0041	10.8903	31.5287	AID504467
thioredoxin glutathione reductase	Schistosoma mansoni	Potency	44.6684	0.1000	22.9075	100.0000	AID485364
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (23)

Assay ID	Title	Year	Journal	Article
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1347082	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID504810	Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347083	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812	Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347086	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1707260	Antiproliferative activity against human SW480 cells incubated for 72 hrs by MTT assay	2020	Journal of medicinal chemistry, 12-24, Volume: 63, Issue:24	Development of Potential Antitumor Agents from the Scaffolds of Plant-Derived Terpenoid Lactones.
AID1707258	Antiproliferative activity against human MDA-MB-435 cells incubated for 48 hrs by [3H]-thymidine incorporation assay	2020	Journal of medicinal chemistry, 12-24, Volume: 63, Issue:24	Development of Potential Antitumor Agents from the Scaffolds of Plant-Derived Terpenoid Lactones.
AID328116	Neuroprotective activity against rat cortical cells assessed as glutamate-induced neurotoxicity by MTT assay	2008	Journal of natural products, Feb, Volume: 71, Issue:2	Neuroprotective limonoids of root bark of Dictamnus dasycarpus.
AID1707257	Antiproliferative activity against human MCF7 cells incubated for 48 hrs by [3H]-thymidine incorporation assay	2020	Journal of medicinal chemistry, 12-24, Volume: 63, Issue:24	Development of Potential Antitumor Agents from the Scaffolds of Plant-Derived Terpenoid Lactones.
AID755466	Antiinflammatory activity in mouse J774A1 cells assessed as reduction of LPS-induced nitric oxide production treated 2 hrs before LPS addition measured after 20 hrs by using Griess reagent	2013	Bioorganic & medicinal chemistry letters, Jul-01, Volume: 23, Issue:13	Rearranged limonoids and chromones from Harrisonia perforata and their anti-inflammatory activity.
AID328118	Neuroprotective activity against rat cortical cells at 0.1 uM assessed as glutamate-induced neurotoxicity by MTT assay	2008	Journal of natural products, Feb, Volume: 71, Issue:2	Neuroprotective limonoids of root bark of Dictamnus dasycarpus.
AID1101971	Antifeedant activity against larvae of Spodoptera frugiperda (fall armyworm) at 100 ppm measured every 30 min for 8 hr by binary choice assay relative to control	2002	Journal of agricultural and food chemistry, Nov-06, Volume: 50, Issue:23	Citrus limonoids and their semisynthetic derivatives as antifeedant agents against Spodoptera frugiperda larvae. A structure-activity relationship study.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	2 (3.77)	18.2507
2000's	10 (18.87)	29.6817
2010's	27 (50.94)	24.3611
2020's	14 (26.42)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (1.89%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	52 (98.11%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
berberine [no description available]	7.48	2	alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound	antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker
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.	2.08	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
4-nitroquinoline-1-oxide 4-nitroquinoline N-oxide : A quinoline N-oxide carrying a nitro substituent at position 4.	3	1	C-nitro compound; quinoline N-oxide	carcinogenic agent
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.	3	1	amino 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
palmatine burasaine: structure in first source	7.48	2	berberine alkaloid; organic heterotetracyclic compound	plant metabolite
titanium Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.	2.41	1	titanium group element atom
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	2.06	1	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
azoxymethane Azoxymethane: A potent carcinogen and neurotoxic compound. It is particularly effective in inducing colon carcinomas.	2.41	2
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).	2	1	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	3.89	4	D-glucopyranose	epitope; mouse metabolite
triptonide triptonide: extracted from Tripterygium wilfordii; structure given in first source. triptonide : A diterpene triepoxide that is triptobenzene K in which the acylhydroquinone moiety has undergone oxidation to the corresponding triepoxyketone derivative. It has been isolated from the roots of Tripterygium wilfordii.	2.25	1	butenolide; cyclic ketone; diterpene triepoxide; organic heteroheptacyclic compound	anti-inflammatory agent; antineoplastic agent; immunosuppressive agent
dictamnine dictamnine: furanoquinoline alkaloid; crosslinks DNA in presence of ultraviolet light	8.73	3	alkaloid antibiotic; organic heterotricyclic compound; organonitrogen heterocyclic compound; oxacycle
jatrorrhizine jatrorrhizine: isolated from bark of Enantia chlorantha (Annonaceae); structure given in first source	7.05	1	alkaloid
nagilactone c nagilactone C: norditerpene lactone isolated from leaves of Podocarpus; structure	2.25	1
brusatol brusatol: quassinoid from B. javanica; structure	2.25	1	triterpenoid
inermin inermin: phytoalexin produced in plants after injection with fungi; RN given refers to (cis-(+-))-isomer; RN for cpd without isomeric designation; structure. (-)-maackiain : The (-)-enantiomer of maackiain.	3.89	2	maackiain
triptolide [no description available]	2.25	1	diterpenoid; epoxide; gamma-lactam; organic heteroheptacyclic compound	antispermatogenic agent; plant metabolite
parthenolide [no description available]	2.25	1	germacranolide
fraxinellone fraxinellone: structure given in first source; RN given for (3R-cis)-isomer	8.92	4	2-benzofurans
chlorolissoclimide chlorolissoclimide: structure given in first source; a labdane cytotoxin isolated from Lissoclinum voeltzkowi Michaelson	2.25	1
bruceine a bruceine A: quassinoid which inhibits protein synthesis & DNA synthesis in cells; RN given refers to (11 beta,12 alpha,15 beta)-isomer; structure given in first source	2.25	1	quassinoid
bruceine b bruceine B: quassinoid which inhibits protein synthesis & DNA synthesis in cells; structure in first source	2.25	1	triterpenoid
jolkinolide a jolkinolide A: isolated from Euphorbia fischeriana	2.25	1	diterpene lactone	metabolite
jolkinolide b jolkinolide B: isolated from Euphorbia fischeriana	2.25	1	diterpene lactone	metabolite
limonin [no description available]	4.82	12	epoxide; furans; hexacyclic triterpenoid; lactone; limonoid; organic heterohexacyclic compound	inhibitor; metabolite; volatile oil component
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	3.73	3
tripdiolide tripdiolide: structure	2.25	1	oxacycle
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	1.99	1	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
taurolithocholic acid Taurolithocholic Acid: A bile salt formed in the liver from lithocholic acid conjugation with taurine, usually as the sodium salt. It solubilizes fats for absorption and is itself absorbed. It is a cholagogue and choleretic.. taurolithocholic acid : The bile acid taurine conjugate of lithocholic acid.	2.15	1	bile acid taurine conjugate; monocarboxylic acid amide	human metabolite
rutaevin rutaevin: from root bark of Dictamnus daycarpus Turcz.	3.39	2	steroid lactone
naringin [no description available]	1.99	1	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; neohesperidoside	anti-inflammatory agent; antineoplastic agent; metabolite
trifolirhizin trifolirhizin: from Sophora flavescens; has inhibitory effect on tyrosinase and melanin synthesis; structure in first source	3.03	1	pterocarpans
thapsigargin Thapsigargin: A sesquiterpene lactone found in roots of THAPSIA. It inhibits SARCOPLASMIC RETICULUM CALCIUM-TRANSPORTING ATPASES.. thapsigargin : An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations.	2.25	1	butyrate ester; organic heterotricyclic compound; sesquiterpene lactone	calcium channel blocker; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
bruceantin [no description available]	2.25	1	triterpenoid
andrographolide [no description available]	2.25	1	carbobicyclic compound; gamma-lactone; labdane diterpenoid; primary alcohol; secondary alcohol	anti-HIV agent; anti-inflammatory drug; antineoplastic agent; metabolite
shihulimonin a shihulimonin A: isolated from Evodia rutaecarpa; structure in first source	2.25	1	limonoid
dichapetalin a dichapetalin A: isolated from Dichapetalum; structure in first source	2.25	1
ginkgolide b [no description available]	2.25	1
dizocilpine maleate Dizocilpine Maleate: A potent noncompetitive antagonist of the NMDA receptor (RECEPTORS, N-METHYL-D-ASPARTATE) used mainly as a research tool. The drug has been considered for the wide variety of neurodegenerative conditions or disorders in which NMDA receptors may play an important role. Its use has been primarily limited to animal and tissue experiments because of its psychotropic effects.. dizocilpine maleate : A maleate salt obtained by reaction of dizocilpine with one equivalent of maleic acid.	2.04	1	maleate salt; tetracyclic antidepressant	anaesthetic; anticonvulsant; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist
17-hydroxyjolkinolide b 17-hydroxyjolkinolide B: isolated from Euphorbia fischeriana	2.25	1	diterpene lactone	metabolite
bn 52020 [no description available]	2.25	1
dichlorolissoclimide dichlorolissoclimide: structure given in first source; a labdane cytotoxin isolated from Lissoclinum voeltzkowi Michaelson	2.25	1
acebutolol alpha-D-glucosyl-(1->4)-alpha-D-mannose : An alpha-D-glucosyl-(1->4)-D-mannopyranose in which the anomeric hydroxy group has alpha configuration.	2.07	1	alpha-D-glucosyl-(1->4)-D-mannopyranose
nomilin [no description available]	3.29	6
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	2.77	3
14-o-phosphonooxymethyltriptolide 14-O-phosphonooxymethyltriptolide disodium salt: pro-drug of triptolide; has antineoplastic activity	2.25	1
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	2.1	1	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger

Condition	Relationship Strength	Studies
Innate Inflammatory Response [description not available]	3.06	4
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.	8.06	4
Benign Neoplasms [description not available]	2.25	1
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.	2.25	1
Lung Injury, Acute [description not available]	2.41	1
Acute Lung Injury A condition of lung damage that is characterized by bilateral pulmonary infiltrates (PULMONARY EDEMA) rich in NEUTROPHILS, and in the absence of clinical HEART FAILURE. This can represent a spectrum of pulmonary lesions, endothelial and epithelial, due to numerous factors (physical, chemical, or biological).	7.41	1
Age-Related Osteoporosis [description not available]	3.01	2
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	3.01	2
Bone Loss, Osteoclastic [description not available]	2.6	1
Sunburn An injury to the skin causing erythema, tenderness, and sometimes blistering and resulting from excessive exposure to the sun. The reaction is produced by the ultraviolet radiation in sunlight.	2.6	1
Chronic Illness [description not available]	2.25	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.8	3
Colorectal Cancer [description not available]	7.25	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).	2.25	1
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.	2.25	1
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)	2.55	2
Cirrhosis, Liver [description not available]	2.31	1
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	2.31	1
Age-Related Macular Degeneration [description not available]	2.31	1
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.	2.31	1
Acute Liver Injury, Drug-Induced [description not available]	2.17	1
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	2.17	1
Diabetic Glomerulosclerosis [description not available]	2.21	1
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	2.8	3
Diabetic Nephropathies KIDNEY injuries associated with diabetes mellitus and affecting KIDNEY GLOMERULUS; ARTERIOLES; KIDNEY TUBULES; and the interstitium. Clinical signs include persistent PROTEINURIA, from microalbuminuria progressing to ALBUMINURIA of greater than 300 mg/24 h, leading to reduced GLOMERULAR FILTRATION RATE and END-STAGE RENAL DISEASE.	2.21	1
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	7.8	3
Cancer of Prostate [description not available]	2.55	2
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	2.55	2
Breast Cancer [description not available]	2.1	1
Breast Neoplasms Tumors or cancer of the human BREAST.	2.1	1
Cardiometabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components not only include metabolic dysfunctions of METABOLIC SYNDROME but also HYPERTENSION, and ABDOMINAL OBESITY.	2.11	1
Hypertrophy General increase in bulk of a part or organ due to CELL ENLARGEMENT and accumulation of FLUIDS AND SECRETIONS, not due to tumor formation, nor to an increase in the number of cells (HYPERPLASIA).	7.11	1
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	7.49	2
Metabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components of metabolic syndrome include ABDOMINAL OBESITY; atherogenic DYSLIPIDEMIA; HYPERTENSION; HYPERGLYCEMIA; INSULIN RESISTANCE; a proinflammatory state; and a prothrombotic (THROMBOSIS) state.	2.11	1
Cancer of Pancreas [description not available]	2.06	1
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	2.06	1
Carcinoma, Epidermoid [description not available]	3	1
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	3	1
Cancer of Mouth [description not available]	3.36	2
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	3	1
Mouth Neoplasms Tumors or cancer of the MOUTH.	3.36	2
Leukemia L 1210 [description not available]	2	1
Cancer of Colon [description not available]	2.41	2
Condition, Preneoplastic [description not available]	2	1
Colonic Neoplasms Tumors or cancer of the COLON.	2.41	2
Precancerous Conditions Pathological conditions that tend eventually to become malignant.	2	1

obacunone

Description

Cross-References

Synonyms (34)

Research Excerpts

Overview

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Drug Classes (1)

Protein Targets (3)

Potency Measurements

Bioassays (23)

Research

Studies (53)

Market Indicators

Research Demand Index: 26.88

Study Types

obacunone

Description

Related Flora

Cross-References

Synonyms (34)

Research Excerpts

Overview

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Drug Classes (1)

Protein Targets (3)

Potency Measurements

Bioassays (23)

Research

Studies (53)

Market Indicators

Research Demand Index: 26.88

Study Types

Related Drugs (47)

Related Conditions (46)