Page last updated: 2024-12-11

dihydroouabain

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

Description

dihydroouabain: RN given refers to (1beta,3beta,5beta,11alpha,20xi)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

dihydroouabain : A cardenolide glycoside that is ouabain in which the double bond in the lactone ring has been reduced to a single bond. It is a cardiac glycoside and a derivative of ouabain which is used as a sodium pump antagonist and exhibits ionotropic effects. [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]

Cross-References

ID SourceID
PubMed CID6852401
CHEMBL ID1581197
CHEBI ID131146
PubMed CID11957513
MeSH IDM0040991

Synonyms (32)

Synonym
MLS002153278 ,
smr000058659
MLS000069775 ,
4-[(1r,3s,5s,8r,9s,10r,11r,13r,14s,17r)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyl-2-oxanyl]oxy]-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-oxolanone
CHEBI:131146
4-[(1r,3s,5s,8r,9s,10r,11r,13r,14s,17r)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]oxolan-2-one
HMS2233P07
dihydro-ouabain
CHEMBL1581197
OPERA_ID_1180
mfcd00049227
cardanolide,3-[(6-deoxy-a-l-mannopyranosyl)oxy]-1,5,11,14,19-pentahydroxy-,(1b,3b,5b,11a,20x)-
REGID_FOR_CID_6852401
Q27224932
MLS001148144 ,
smr000653457
dihydroouabain
EU-0100355
LOPAC0_000355
1183-35-3
NCGC00162131-02
D 0670
3-[(6-deoxyhexopyranosyl)oxy]-1,5,11,14,19-pentahydroxycardanolide
HMS3261G11
CCG-204450
HMS2233D06
LP00355
J-003737
SR-01000075801-1
sr-01000075801
SDCCGSBI-0050343.P002 ,
4-[(1r,3s,5s,9s,10r,11r,13r,14s,17r)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]oxolan-2-one

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" The dose-response relation for the cardiotonic steroid dihydroouabain (DHO) was obtained by measuring the change in membrane current caused by application of concentrations of 1-100 microM."( Properties of an electrogenic sodium-potassium pump in isolated canine Purkinje myocytes.
Cohen, IS; Datyner, NB; Gintant, GA; Mulrine, NK; Pennefather, P, 1987
)
0.27
" From dose-response curves of the drug-induced current change (ID) the equilibrium dissociation constant of the binding of DHO to the Na-K pump (KD) and the electrogenic pump current flowing in the steady state (Ip) were inferred (Daut & RĂ¼del, 1982b)."( Inhibition of the sodium pump in guinea-pig ventricular muscle by dihydro-ouabain: effects of external potassium and sodium.
Daut, J, 1983
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
radiosensitizing agentA drug that makes increases the sensitivity of tumour cells to radiation therapy.
EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitorAn EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of Na(+)/K(+)-transporting ATPase (EC 3.6.3.9).
[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 (1)

ClassDescription
cardenolide glycosideAny member of the class of cardenolides with glycosyl residues attached to position 3.
[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 (23)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
ATAD5 protein, partialHomo sapiens (human)Potency2.13380.004110.890331.5287AID504466; AID504467; AID624247; AID624248; AID624249; AID624250; AID624251; AID624252
TDP1 proteinHomo sapiens (human)Potency29.09290.000811.382244.6684AID686978
Smad3Homo sapiens (human)Potency14.12540.00527.809829.0929AID588855
67.9K proteinVaccinia virusPotency1.12200.00018.4406100.0000AID720579; AID720580
IDH1Homo sapiens (human)Potency1.83560.005210.865235.4813AID686970
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency0.89130.035520.977089.1251AID504332
NPC intracellular cholesterol transporter 1 precursorHomo sapiens (human)Potency2.81840.01262.451825.0177AID485313
chromobox protein homolog 1Homo sapiens (human)Potency100.00000.006026.168889.1251AID540317
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency0.41090.00419.984825.9290AID504444
transcriptional regulator ERG isoform 3Homo sapiens (human)Potency8.91250.794321.275750.1187AID624246
importin subunit beta-1 isoform 1Homo sapiens (human)Potency29.09295.804836.130665.1308AID540253
ras-related protein Rab-9AHomo sapiens (human)Potency1.41250.00022.621531.4954AID485297
snurportin-1Homo sapiens (human)Potency29.09295.804836.130665.1308AID540253
GTP-binding nuclear protein Ran isoform 1Homo sapiens (human)Potency29.09295.804816.996225.9290AID540253
gemininHomo sapiens (human)Potency3.31410.004611.374133.4983AID624296; AID624297
survival motor neuron protein isoform dHomo sapiens (human)Potency16.20860.125912.234435.4813AID1458; AID1740
lamin isoform A-delta10Homo sapiens (human)Potency3.98110.891312.067628.1838AID1487
glp-1 receptor, partialHomo sapiens (human)Potency1.00000.01846.806014.1254AID624417
ATAD5 protein, partialHomo sapiens (human)Potency1.25440.004110.890331.5287AID504466; AID504467
TDP1 proteinHomo sapiens (human)Potency29.09290.000811.382244.6684AID686978
Smad3Homo sapiens (human)Potency15.84890.00527.809829.0929AID588855
67.9K proteinVaccinia virusPotency1.77830.00018.4406100.0000AID720579; AID720580
IDH1Homo sapiens (human)Potency5.17350.005210.865235.4813AID686970
NPC intracellular cholesterol transporter 1 precursorHomo sapiens (human)Potency3.98110.01262.451825.0177AID485313
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency0.68210.00419.984825.9290AID504444; AID720524
parathyroid hormone/parathyroid hormone-related peptide receptor precursorHomo sapiens (human)Potency89.12513.548119.542744.6684AID743266
ras-related protein Rab-9AHomo sapiens (human)Potency3.54810.00022.621531.4954AID485297
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency89.12510.050127.073689.1251AID588590
gemininHomo sapiens (human)Potency1.89630.004611.374133.4983AID624296; AID624297
[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)
Kruppel-like factor 5Homo sapiens (human)IC50 (µMol)3.85400.02970.88853.8540AID1973
Muscarinic acetylcholine receptor M1Rattus norvegicus (Norway rat)IC50 (µMol)3.85400.00052.773925.1700AID1973
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
PAX8Homo sapiens (human)AC505.38000.04885.435469.1700AID687027
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (39)

Assay IDTitleYearJournalArticle
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation Compound Set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation 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.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation 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.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation 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.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation 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.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation 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.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation 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.
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.
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.
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.
AID651635Viability Counterscreen for Primary 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.
AID1745845Primary qHTS 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.
AID1224864HCS microscopy assay (F508del-CFTR)2016PloS one, , Volume: 11, Issue:10
Increasing the Endoplasmic Reticulum Pool of the F508del Allele of the Cystic Fibrosis Transmembrane Conductance Regulator Leads to Greater Folding Correction by Small Molecule Therapeutics.
AID651635Viability Counterscreen for Primary qHTS 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.
AID1745845Primary 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.
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.
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.
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.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
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 (107)

TimeframeStudies, This Drug (%)All Drugs %
pre-199043 (40.19)18.7374
1990's36 (33.64)18.2507
2000's17 (15.89)29.6817
2010's9 (8.41)24.3611
2020's2 (1.87)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.53

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 Index17.53 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.30 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.53)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews3 (2.80%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
Other104 (97.20%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]