Page last updated: 2024-11-06

1',2'-dihydrorotenone

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

Description

1',2'-dihydrorotenone: RN given refers to (2R-(2alpha,6aalpha,12aalpha))-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID243725
CHEMBL ID267630
SCHEMBL ID19035536
MeSH IDM0131055

Synonyms (46)

Synonym
nsc53866
nsc-53866
wln: t g5 d6 b666 cv ho mo po du- l gu- ktttt&j iy1&u1 so1 to1
[1]benzopyrano[3,3-h][1]benzopyran-6(6a.alpha.h)-one, 1,2,12,12a.alpha.-tetrahydro-2.alpha.-isopropyl-8,9-dimethoxy-
[1]benzopyrano[3,3-h][1]benzopyran-6(6ah)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethyl)-, [2r-(2.alpha.,6a.alpha.,12a.alpha.)]-
s,s-dihydrorotenone
nsc-351138
6',7'-dihydrorotenone
rotenone, dihydro-
NSC351138 ,
6659-45-6
rotenone, dihydro- (van)
dihydrorotenone (van)
epa pesticide chemical code 071002
(1)benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aalphah)-one, 1,2,12,12aalpha-tetrahydro-2alpha-isopropyl-8,9-dimethoxy-
(1)benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6ah)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethyl)-, (2r-(2alpha,6aalpha,12aalpha))-
nsc 351138
caswell no. 353
(1)benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6a-alphah)-one, 1,2,12,12a-alpha-tetrahydro-2-alpha-isopropyl-8,9-dimethoxy-
nsc 53866
1',2'-dihydrorotenone
SR-01000642530-1
MLS000851173 ,
smr000457416
2-isopropyl-8,9-dimethoxy-1,2,6,6a,12,12a-hexahydrochromeno[3,4-b]furo[2,3-h]chromen-6-one
CHEMBL267630
sr-01000767777
SR-01000767777-2
CCG-53362
538cx0lppo ,
(1)benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6ah)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethyl)-, (2r,6as,12as)-
unii-538cx0lppo
cid_243725
bdbm97131
AKOS024419416
DTXSID5041227
sr-01000642530
SR-01000642530-2
SCHEMBL19035536
2-isopropyl-8,9-di-meo-1,2,12,12a-4h-6ah-chromeno(3,4-b)furo(2,3-h)chromen-6-one
(2r,6as,12as)-2-isopropyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6ah)-one
Q27261081
CS-0032420
HY-N4202
(1s,6r,13s)-16,17-dimethoxy-6-propan-2-yl-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
MS-26678

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" PYR was also highly toxic to midbrain organotypic slices."( Mechanism of toxicity of pesticides acting at complex I: relevance to environmental etiologies of Parkinson's disease.
Greenamyre, JT; Matsuno-Yagi, A; Miller, GW; Panov, AV; Richardson, JR; Seo, BB; Sherer, TB; Testa, CM; Yagi, T, 2007
)
0.34
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (18)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Beta-lactamaseEscherichia coli K-12Potency35.48130.044717.8581100.0000AID485341
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency44.66840.631035.7641100.0000AID504339
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency39.81070.177814.390939.8107AID2147
glp-1 receptor, partialHomo sapiens (human)Potency1.00000.01846.806014.1254AID624417
ATAD5 protein, partialHomo sapiens (human)Potency0.05800.004110.890331.5287AID504467
TDP1 proteinHomo sapiens (human)Potency0.21140.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency19.95260.180013.557439.8107AID1460
Smad3Homo sapiens (human)Potency1.99530.00527.809829.0929AID588855
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency44.66840.707936.904389.1251AID504333
NPC intracellular cholesterol transporter 1 precursorHomo sapiens (human)Potency1.12200.01262.451825.0177AID485313
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency0.26100.00419.984825.9290AID504444; AID720524
mitogen-activated protein kinase 1Homo sapiens (human)Potency35.48130.039816.784239.8107AID1454
ras-related protein Rab-9AHomo sapiens (human)Potency0.07080.00022.621531.4954AID485297
eyes absent homolog 2 isoform aHomo sapiens (human)Potency100.00001.199814.641950.1187AID488837
peptidyl-prolyl cis-trans isomerase NIMA-interacting 1Homo sapiens (human)Potency79.43280.425612.059128.1838AID504891
gemininHomo sapiens (human)Potency29.09290.004611.374133.4983AID624296; AID624297
Glycoprotein hormones alpha chainHomo sapiens (human)Potency4.46684.46688.344810.0000AID624291
[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)
galanin receptor type 3Homo sapiens (human)IC50 (µMol)0.01390.00661.54317.3650AID687013; AID743095
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (14)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell population proliferationGlycoprotein hormones alpha chainHomo sapiens (human)
hormone-mediated signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
regulation of signaling receptor activityGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of steroid biosynthetic processGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell migrationGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid gland developmentGlycoprotein hormones alpha chainHomo sapiens (human)
luteinizing hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIGlycoprotein hormones alpha chainHomo sapiens (human)
negative regulation of organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid hormone generationGlycoprotein hormones alpha chainHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
protein bindingGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
extracellular regionGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
Golgi lumenGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone complexGlycoprotein hormones alpha chainHomo sapiens (human)
pituitary gonadotropin complexGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. 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.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
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.
AID1745847CMV-Luciferase Counterscreen for Inhibitors of ATXN expression
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. 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.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1745846Firefly Luciferase Counterscreen for Inhibitors of ATXN expression
AID1745850Viability Counterscreen for Confirmatory qHTS for Inhibitors of ATXN expression
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. 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.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745848Confirmatory qHTS for Inhibitors of ATXN expression
AID1745849Viability Counterscreen for CMV-Luciferase Assay of Inhibitors of ATXN expression
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.
AID79366Compound was evaluated for the inhibitory activity against Acetylcholine in guinea pig ileum1980Journal of medicinal chemistry, Sep, Volume: 23, Issue:9
Evaluation of rotenone and related compounds as antagonists of slow-reacting substance of anaphylaxis.
AID79368Compound was evaluated for the inhibitory activity against Serotonin in guinea pig ileum1980Journal of medicinal chemistry, Sep, Volume: 23, Issue:9
Evaluation of rotenone and related compounds as antagonists of slow-reacting substance of anaphylaxis.
AID78106Compound was evaluated in vivo for collapse time in guinea pig anaphylaxis model at dose 10 mg/kg1980Journal of medicinal chemistry, Sep, Volume: 23, Issue:9
Evaluation of rotenone and related compounds as antagonists of slow-reacting substance of anaphylaxis.
AID78130Compound was evaluated for the inhibitory activity against slow reacting substance of anaphylaxis (SRS-A) of guinea pig ileum1980Journal of medicinal chemistry, Sep, Volume: 23, Issue:9
Evaluation of rotenone and related compounds as antagonists of slow-reacting substance of anaphylaxis.
AID79367Compound was evaluated for the inhibitory activity against Histamine in guinea pig ileum1980Journal of medicinal chemistry, Sep, Volume: 23, Issue:9
Evaluation of rotenone and related compounds as antagonists of slow-reacting substance of anaphylaxis.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (24)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (16.67)18.7374
1990's8 (33.33)18.2507
2000's3 (12.50)29.6817
2010's7 (29.17)24.3611
2020's2 (8.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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%
Other24 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]