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

dunnione

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

Description

dunnione: RN given for (+)-isomer; an industrial fungicide; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID262097
CHEMBL ID3398290
CHEBI ID4723
SCHEMBL ID103115
MeSH IDM0449542

Synonyms (34)

Synonym
dl-dunnione
nsc-95403
87402-65-1
nsc95403
33404-57-8
dunnione
2,3,3-trimethyl-2h-benzo[g][1]benzofuran-4,5-dione
naphtho(1,2-b)furan-4,5-dione, 2,3-dihydro-2,3,3-trimethyl-
q5dze9stu9 ,
dunnione, (+/-)-
dunnione, (s)-
w59r466kwx ,
unii-q5dze9stu9
521-49-3
unii-w59r466kwx
2,3-dihydro-2,3,3-trimethylnaphtho(1,2-b)furan-4,5-dione
unii-v54u6ys3c9
einecs 251-507-0
AC1Q6KGN ,
SCHEMBL103115
CHEBI:4723 ,
2,3-dihydro-2,3,3-trimethylnaphtho[1,2-b]furan-4,5-dione
surecn103115
CHEMBL3398290
AKOS030228712
2,3,3-trimethyl-2h,3h,4h,5h-naphtho[1,2-b]furan-4,5-dione
AS-70068
(+/-)-dunnione
Q27106452
2,3-dihydro-2,3,3-trimethylnaphtho(1,2-b)furan-4,5-dione; 2,3,3-trimethyl-2h-benzo[g][1]benzofuran-4,5-dione
DTXSID80955029
2,3,3-trimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
naphtho[1,2-b]furan-4,5-dione, 2,3-dihydro-2,3,3-trimethyl-
sl-11010

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Furthermore, we show that the induction of cellular NAD(+) levels using dunnione, which targets intracellular NQO1, prevents the toxic effects of cisplatin through the regulation of PARP-1 and SIRT1 activity."( Dunnione ameliorates cisplatin ototoxicity through modulation of NAD(+) metabolism.
Cho, EY; Choe, SK; Khadka, D; Kim, HJ; Kwak, TH; Lee, S; Lee, SB; Oh, GS; Pandit, A; Park, R; Shen, A; Shim, H; So, HS; Yang, SH, 2016)		2.11
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
naphthofuran
[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 (8)

Assay IDTitleYearJournalArticle
AID1191934Cytotoxicity against human A549 cells after 72 hrs by MTT assay2015Bioorganic & medicinal chemistry letters, Mar-15, Volume: 25, Issue:6
Synthesis and evaluation of (±)-dunnione and its ortho-quinone analogues as substrates for NAD(P)H:quinone oxidoreductase 1 (NQO1).
AID1441542Electrochemical behavior of the compound assessed as electrochemical redox potential with reference to ferrocene at 1 mM using Ag/AgCl reference electrode measured up to -2 V at potential sweep rates of 50 mV/s by cyclic voltammetry2017European journal of medicinal chemistry, Mar-31, Volume: 129Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile.
AID1441540Substrate activity at recombinant human CPR expressed in baculovirus infected insect cells assessed as compound reduction rate by measuring NADPH consumption per umol of enzyme preincubated for 3 mins followed by NADPH addition measured for 5 mins at 2 se2017European journal of medicinal chemistry, Mar-31, Volume: 129Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile.
AID1191935Cytotoxicity against human A549 cells after 72 hrs by MTT assay in presence of NQO1 inhibitor dicoumarol2015Bioorganic & medicinal chemistry letters, Mar-15, Volume: 25, Issue:6
Synthesis and evaluation of (±)-dunnione and its ortho-quinone analogues as substrates for NAD(P)H:quinone oxidoreductase 1 (NQO1).
AID1191936Selectivity ratio of IC50 for human A549 cells in presence of NQO1 inhibitor dicoumarol to IC50 for human A549 cells2015Bioorganic & medicinal chemistry letters, Mar-15, Volume: 25, Issue:6
Synthesis and evaluation of (±)-dunnione and its ortho-quinone analogues as substrates for NAD(P)H:quinone oxidoreductase 1 (NQO1).
AID1441539Substrate activity at recombinant human NQO1 expressed in Escherichia coli assessed as compound reduction rate by measuring NADPH consumption per umol of enzyme preincubated for 3 mins followed by NADPH addition measured for 5 mins at 2 sec time interval 2017European journal of medicinal chemistry, Mar-31, Volume: 129Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile.
AID1191933Activity of human recombinant NQO1 assessed as ratio of kcat to Km preincubated for 3 mins before NADPH addition at 0.1 to 5 umol/L by NADPH recycling assay2015Bioorganic & medicinal chemistry letters, Mar-15, Volume: 25, Issue:6
Synthesis and evaluation of (±)-dunnione and its ortho-quinone analogues as substrates for NAD(P)H:quinone oxidoreductase 1 (NQO1).
AID1441541Selectivity ratio of compound reduction rate catalyzed by recombinant human NQO1 expressed in Escherichia coli to compound reduction rate catalyzed by recombinant human CPR expressed in baculovirus infected insect cells2017European journal of medicinal chemistry, Mar-31, Volume: 129Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (7.14)29.6817
2010's11 (78.57)24.3611
2020's2 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.71

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index20.71 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index5.79 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.71)

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%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
lapachol
lapachol : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone substituted by hydroxy and 3-methylbut-2-en-1-yl groups at positions 2 and 3, respectively. It is a natural compound that exhibits antibacterial and anticancer properties, first isolated in 1882 from the bark of Tabebuia avellanedae.		2.1110
beta-lapachone
beta-lapachone: antineoplastic inhibitor of reverse transcriptase, DNA topoisomerase, and DNA polymerase. beta-lapachone : A benzochromenone that is 3,4-dihydro-2H-benzo[h]chromene-5,6-dione substituted by geminal methyl groups at position 2. Isolated from Tabebuia avellanedae, it exhibits antineoplastic and anti-inflammatory activities.		2.8130benzochromenone;
orthoquinones		anti-inflammatory agent;
antineoplastic agent;
plant metabolite
vitamin k 3
Vitamin K 3: A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.		2.11101,4-naphthoquinones;
vitamin K		angiogenesis inhibitor;
antineoplastic agent;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor;
human urinary metabolite;
nutraceutical
lawsone
lawsone: a molluscacide from leaves of Lawsonia inermis L. topical sunscreening agent; structure; powdered leaves of Lawsonia inermis(Lythraceae) used as brown hair dye. lawsone : 1,4-Naphthoquinone carrying a hydroxy function at C-2. It is obtained from the leaves of Lawsonia inermis.		2.1110
2-methylanthraquinone
2-methylanthraquinone: form Morinda officinalis How.. 2-methylanthraquinone : An anthraquinone that is 9,10-anthraquinone in which the hydrogen at position 2 is substituted by a methyl group.		2.0610anthraquinone
2-methylpentane
Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.		2.610alkane
ethyl acetate
ethyl acetate : The acetate ester formed between acetic acid and ethanol.		2.610acetate ester;
ethyl ester;
volatile organic compound		EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor;
metabolite;
polar aprotic solvent;
Saccharomyces cerevisiae metabolite
tiletamine hydrochloride
Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.		2.5220
alkenes
[no description available]		2.1110
2-butene
2-butene: RN given refers to cpd without isomeric designation		2.1110but-2-ene
cedrol
cedrol: a cyclic terpenoid from cedarwood oil; 8-epicedrol is an epimer		2.5220cedrane sesquiterpenoid;
tertiary alcohol
alpha-lapachone
alpha-lapachone: structure in first source		2.1510organic heterotricyclic compound;
organooxygen compound
xyloidone
[no description available]		2.1510
halleridone
halleridone: from Cornus Controversa, Mimulus glabratus and M. luteus; structure in first source		2.5220
1-hydroxy-2-methylanthraquinone
1-hydroxy-2-methylanthraquinone: from root of Prismatomeris tetrandra. 1-hydroxy-2-methyl-9,10-anthraquinone : A member of the class of hydroxyanthraquinones that is anthracene-9,10-dione substituted by a hydroxy group at position 1 and a methyl group at position 2. It has been isolated from the roots of Rubia yunnanensis.		2.0610monohydroxyanthraquinoneplant metabolite
phenazopyridine
lapachenole: photoaffinity label		2.5220benzochromene
benzofurans
Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.		2.5220
naphthoquinones
Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.		9.07130
nor-beta-lapachone
nor-beta-lapachone: has antineoplastic activity; structure in first source		2.5320
calceolarioside a
calceolarioside A: structure given in first source; isolated from Calceolaria hypericina; induces platelet aggregation		2.610hydroxycinnamic acid
dinoprostone
prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.		2.1510prostaglandins Ehuman metabolite;
mouse metabolite;
oxytocic
nad
NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.		3.0840organophosphate oxoanioncofactor;
human metabolite;
hydrogen acceptor;
Saccharomyces cerevisiae metabolite
thromboplastin
Thromboplastin: Constituent composed of protein and phospholipid that is widely distributed in many tissues. It serves as a cofactor with factor VIIa to activate factor X in the extrinsic pathway of blood coagulation.		2.3110
ConditionIndicatedRelationship StrengthStudiesTrials
Hypercoagulability
[description not available]		02.3110
Breast Cancer
[description not available]		02.3110
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.8930
Blood Clot
[description not available]		02.3110
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.3110
Thrombosis
Formation and development of a thrombus or blood clot in the blood vessel.		02.3110
Thrombophilia
A disorder of HEMOSTASIS in which there is a tendency for the occurrence of THROMBOSIS.		02.3110
Anasarca
[description not available]		02.1510
Allodynia
[description not available]		02.1510
Edema
Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.		02.1510
Innate Inflammatory Response
[description not available]		02.1710
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.		02.1710
Kidney Diseases
Pathological processes of the KIDNEY or its component tissues.		02.1710
Deafness, Transitory
[description not available]		02.1310
Hearing Loss
A general term for the complete or partial loss of the ability to hear from one or both ears.		02.1310
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		02.1110