Page last updated: 2024-11-11

(8R)-7-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,13,14-triol

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

Cross-References

ID SourceID
PubMed CID6603798
CHEMBL ID288096
CHEBI ID92298
SCHEMBL ID1325960

Synonyms (33)

Synonym
BRD-K16604360-001-01-8
(r)-6-propyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-2,10,11-triol
LOPAC0_000455
NCGC00015295-01 ,
lopac-d-030
smr000326921
MLS000860063 ,
BIOMOL-NT_000074
BPBIO1_001392
NCGC00162160-04
CHEMBL288096 ,
NCGC00162160-03
SCHEMBL1325960
CCG-204547
2-oh-npa
77630-02-5
r( )-2,10,11-trihydroxy-n-propyl-noraporphine hydrobromide hydrate
bdbm52987
(6ar)-6-propyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-2,10,11-triol;hydrate;hydrobromide
cid_23640911
r-(-)-2,10,11-trihydroxy-n-propylnorapomorphine
DTXSID00435151
CHEBI:92298
(6ar)-6-propyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-2,10,11-triol
Q4596911
(8r)-7-propyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-2,13,14-triol
unii-9xdt3xv7jx
SDCCGSBI-0050440.P002
2,10,11-trihydroxy-n-propylnoraporphine, (-)
4h-dibenzo(de,g)quinoline-2,10,11-triol, 5,6,6a,7-tetrahydro-6-propyl-, (6ar)-
(6ar)-5,6,6a,7-tetrahydro-6-propyl-4h-dibenzo(de,g)quinoline-2,10,11-triol
9XDT3XV7JX ,
PD052816
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
aporphine alkaloidAny benzylisoquinoline alkaloid that has a structure based on 4H-dibenzo[de,g]quinoline or its 3-methyl derivative.
[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 (41)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, HADH2 proteinHomo sapiens (human)Potency14.14060.025120.237639.8107AID886; AID893
Chain B, HADH2 proteinHomo sapiens (human)Potency14.14060.025120.237639.8107AID886; AID893
dopamine D1 receptorHomo sapiens (human)Potency0.06510.00521.30228.1995AID624455
thioredoxin reductaseRattus norvegicus (Norway rat)Potency14.66290.100020.879379.4328AID488773; AID588453; AID588456
RGS12Homo sapiens (human)Potency31.62280.794310.991425.1189AID879
ClpPBacillus subtilisPotency25.11891.995322.673039.8107AID651965
NFKB1 protein, partialHomo sapiens (human)Potency5.62340.02827.055915.8489AID895; AID928
GLS proteinHomo sapiens (human)Potency1.41250.35487.935539.8107AID624146
TDP1 proteinHomo sapiens (human)Potency8.42790.000811.382244.6684AID686978; AID686979
ThrombopoietinHomo sapiens (human)Potency10.00000.02517.304831.6228AID917; AID918
hypoxia-inducible factor 1, alpha subunit (basic helix-loop-helix transcription factor)Homo sapiens (human)Potency2.51190.00137.762544.6684AID914; AID915
regulator of G-protein signaling 4Homo sapiens (human)Potency0.53180.531815.435837.6858AID504845
arylsulfatase AHomo sapiens (human)Potency7.56861.069113.955137.9330AID720538
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency1.12200.035520.977089.1251AID504332
heat shock 70kDa protein 5 (glucose-regulated protein, 78kDa)Homo sapiens (human)Potency58.47890.016525.307841.3999AID602332
cytochrome P450 2D6 isoform 1Homo sapiens (human)Potency15.84890.00207.533739.8107AID891
cellular tumor antigen p53 isoform aHomo sapiens (human)Potency25.11890.316212.443531.6228AID902
cytochrome P450 2C9 precursorHomo sapiens (human)Potency39.81070.00636.904339.8107AID883
D(1A) dopamine receptorHomo sapiens (human)Potency0.63100.02245.944922.3872AID488983
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency5.01190.354828.065989.1251AID504847
chromobox protein homolog 1Homo sapiens (human)Potency1.33710.006026.168889.1251AID488953
guanine nucleotide-binding protein G(i) subunit alpha-1 isoform 1Homo sapiens (human)Potency31.62280.794312.126325.1189AID879
mitogen-activated protein kinase 1Homo sapiens (human)Potency3.98110.039816.784239.8107AID995
flap endonuclease 1Homo sapiens (human)Potency20.52330.133725.412989.1251AID488816; AID588795
serine/threonine-protein kinase mTOR isoform 1Homo sapiens (human)Potency18.98500.00378.618923.2809AID2660; AID2666; AID2667; AID2668
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency35.48130.050127.073689.1251AID588590
M-phase phosphoprotein 8Homo sapiens (human)Potency11.91730.177824.735279.4328AID488949
muscarinic acetylcholine receptor M1Rattus norvegicus (Norway rat)Potency7.06580.00106.000935.4813AID943; AID944
lethal factor (plasmid)Bacillus anthracis str. A2012Potency7.94330.020010.786931.6228AID912
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency39.81070.00638.235039.8107AID883
D(1A) dopamine receptorSus scrofa (pig)Potency23.28090.00378.108123.2809AID2667
Ataxin-2Homo sapiens (human)Potency25.11890.011912.222168.7989AID588378
2,3-bisphosphoglycerate-independent phosphoglycerate mutaseLeishmania major strain FriedlinPotency37.93307.568615.230621.3313AID504548
ATP-dependent phosphofructokinaseTrypanosoma brucei brucei TREU927Potency3.01310.060110.745337.9330AID485368
[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)
DRattus norvegicus (Norway rat)IC50 (µMol)1.01630.00030.50267.7625AID313111; AID45982; AID45983; AID61026
DRattus norvegicus (Norway rat)Ki0.91750.00010.610010.0000AID313111; AID61497
D(3) dopamine receptorRattus norvegicus (Norway rat)IC50 (µMol)0.31250.00030.39075.4000AID45982; AID45983
D(2) dopamine receptorBos taurus (cattle)Ki0.00120.00000.58366.1000AID62464
D(1B) dopamine receptorRattus norvegicus (Norway rat)IC50 (µMol)0.31250.00030.35635.4000AID45982; AID45983
D(4) dopamine receptorRattus norvegicus (Norway rat)IC50 (µMol)0.31250.00030.38715.4000AID45982; AID45983
D(2) dopamine receptorRattus norvegicus (Norway rat)IC50 (µMol)0.15630.00010.54948.4000AID313112; AID45982; AID45983; AID61403
D(2) dopamine receptorRattus norvegicus (Norway rat)Ki0.00010.00000.437510.0000AID313112; AID65113
DBos taurus (cattle)Ki0.00120.00012.367610.0000AID62464
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (12)

Processvia Protein(s)Taxonomy
synaptic transmission, dopaminergicD(2) dopamine receptorBos taurus (cattle)
negative regulation of prolactin secretionD(2) dopamine receptorBos taurus (cattle)
negative regulation of lactationD(2) dopamine receptorBos taurus (cattle)
positive regulation of mammary gland involutionD(2) dopamine receptorBos taurus (cattle)
hyaloid vascular plexus regressionD(2) dopamine receptorBos taurus (cattle)
synaptic transmission, dopaminergicDBos taurus (cattle)
vasodilationDBos taurus (cattle)
negative regulation of receptor internalizationAtaxin-2Homo sapiens (human)
regulation of translationAtaxin-2Homo sapiens (human)
RNA metabolic processAtaxin-2Homo sapiens (human)
P-body assemblyAtaxin-2Homo sapiens (human)
stress granule assemblyAtaxin-2Homo sapiens (human)
RNA transportAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
RNA bindingAtaxin-2Homo sapiens (human)
epidermal growth factor receptor bindingAtaxin-2Homo sapiens (human)
protein bindingAtaxin-2Homo sapiens (human)
mRNA bindingAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
Golgi membraneD(2) dopamine receptorBos taurus (cattle)
endoplasmic reticulum membraneDBos taurus (cattle)
dendritic spineDBos taurus (cattle)
ciliary membraneDBos taurus (cattle)
cytoplasmAtaxin-2Homo sapiens (human)
Golgi apparatusAtaxin-2Homo sapiens (human)
trans-Golgi networkAtaxin-2Homo sapiens (human)
cytosolAtaxin-2Homo sapiens (human)
cytoplasmic stress granuleAtaxin-2Homo sapiens (human)
membraneAtaxin-2Homo sapiens (human)
perinuclear region of cytoplasmAtaxin-2Homo sapiens (human)
ribonucleoprotein complexAtaxin-2Homo sapiens (human)
cytoplasmic stress granuleAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (39)

Assay IDTitleYearJournalArticle
AID1508627Counterscreen qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: GLuc-NoTag assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1508628Confirmatory qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347049Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot screen2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID588349qHTS for Inhibitors of ATXN expression: Validation of Cytotoxic Assay
AID1347045Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot counterscreen GloSensor control cell line2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID504836Inducers of the Endoplasmic Reticulum Stress Response (ERSR) in human glioma: Validation2002The Journal of biological chemistry, Apr-19, Volume: 277, Issue:16
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.
AID1347405qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS LOPAC collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347410qHTS for inhibitors of adenylyl cyclases using a fission yeast platform: a pilot screen against the NCATS LOPAC library2019Cellular signalling, 08, Volume: 60A fission yeast platform for heterologous expression of mammalian adenylyl cyclases and high throughput screening.
AID588378qHTS for Inhibitors of ATXN expression: Validation
AID1347057CD47-SIRPalpha protein protein interaction - LANCE assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction 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.
AID1347050Natriuretic polypeptide receptor (hNpr2) antagonism - Pilot subtype selectivity assay2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347058CD47-SIRPalpha protein protein interaction - HTRF assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347151Optimization of GU AMC qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347059CD47-SIRPalpha protein protein interaction - Alpha assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
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.
AID1508629Cell Viability qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID61403Binding affinity against Dopamine receptor D2 from rat brain corpus striatum membrane1990Journal of medicinal chemistry, Dec, Volume: 33, Issue:12
Synthesis and dopamine receptor affinity of (R)-(-)-2-fluoro-N-n-propylnorapomorphine: a highly potent and selective dopamine D2 agonist.
AID313112Displacement of [3H]raclopride from rat dopamine D2 receptor2007Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2
Advances in development of dopaminergic aporphinoids.
AID34288Compound was evaluated for the elicited effect on adenylate cyclase activity in homogenates of carp retina at 100 uM1981Journal of medicinal chemistry, Jul, Volume: 24, Issue:7
Aporphines. 34. (-)-2,10,11-Trihydroxy-N-n-propylnoraporphine, a novel dopaminergic aporphine alkaloid with anticonvulsant activity.
AID61497Binding affinity at rat striatal Dopamine receptor D1 using [3H]- SCH-23390 radioligand1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Synthesis and dopamine receptor affinities of enantiomers of 2-substituted apomorphines and their N-n-propyl analogues.
AID62464Agonistic activity against calf striatal Dopamine receptor using [3H]- ADTN radioligand1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Synthesis and dopamine receptor affinities of enantiomers of 2-substituted apomorphines and their N-n-propyl analogues.
AID521220Inhibition of neurosphere proliferation of mouse neural precursor cells by MTT assay2007Nature chemical biology, May, Volume: 3, Issue:5
Chemical genetics reveals a complex functional ground state of neural stem cells.
AID65113Binding affinity at rat striatal Dopamine receptor D2 using [3H]- piperone radioligand1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Synthesis and dopamine receptor affinities of enantiomers of 2-substituted apomorphines and their N-n-propyl analogues.
AID34169Compound was evaluated for the elicited effect on adenylate cyclase activity in homogenates of carp retina at 10 uM1981Journal of medicinal chemistry, Jul, Volume: 24, Issue:7
Aporphines. 34. (-)-2,10,11-Trihydroxy-N-n-propylnoraporphine, a novel dopaminergic aporphine alkaloid with anticonvulsant activity.
AID226917Ratio of binding affinity of D2 to binding affinity of D11990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Synthesis and dopamine receptor affinities of enantiomers of 2-substituted apomorphines and their N-n-propyl analogues.
AID226901Potency ratio as ratio of IC50 of D2 receptor to that of D1 receptor1990Journal of medicinal chemistry, Dec, Volume: 33, Issue:12
Synthesis and dopamine receptor affinity of (R)-(-)-2-fluoro-N-n-propylnorapomorphine: a highly potent and selective dopamine D2 agonist.
AID313111Displacement of [3H]SCH-23390 from rat dopamine D1 receptor2007Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2
Advances in development of dopaminergic aporphinoids.
AID61026Binding affinity against Dopamine receptor D1 from rat brain corpus striatum membrane1990Journal of medicinal chemistry, Dec, Volume: 33, Issue:12
Synthesis and dopamine receptor affinity of (R)-(-)-2-fluoro-N-n-propylnorapomorphine: a highly potent and selective dopamine D2 agonist.
AID155432Duration of protection for abolition of myoclonic responses to photic stimulation in the baboon (Papio papio) at 0.2 mg/kg; Duration of protection ranges from 180-300 min1981Journal of medicinal chemistry, Jul, Volume: 24, Issue:7
Aporphines. 34. (-)-2,10,11-Trihydroxy-N-n-propylnoraporphine, a novel dopaminergic aporphine alkaloid with anticonvulsant activity.
AID45982Inhibition of [3H]apomorphine binding to calf caudate membrane preparation (p4)1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Aporphines, 36. Dopamine receptor interactions of trihydroxyaporphines. Synthesis, radioreceptor binding, and striatal adenylate cyclase stimulation of 2,10,11-trihydroxyaporphines in comparison with other hydroxylated aporphines.
AID45983Inhibition of [3H]spiroperidol binding to calf caudate membrane preparation (p4)1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Aporphines, 36. Dopamine receptor interactions of trihydroxyaporphines. Synthesis, radioreceptor binding, and striatal adenylate cyclase stimulation of 2,10,11-trihydroxyaporphines in comparison with other hydroxylated aporphines.
AID112341Evaluated for audiogenic seizures in DBA/ 2 mice, in the protection against paroxysimal EEG at an interval of 30 minutes1981Journal of medicinal chemistry, Jul, Volume: 24, Issue:7
Aporphines. 34. (-)-2,10,11-Trihydroxy-N-n-propylnoraporphine, a novel dopaminergic aporphine alkaloid with anticonvulsant activity.
AID34458Dopamine sensitive adenylate cyclase activity (stimulation) in homogenates of rat brain striatal tissue was assessed at 50 uM; + = <40% increase of cAMP above basal activity1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Aporphines, 36. Dopamine receptor interactions of trihydroxyaporphines. Synthesis, radioreceptor binding, and striatal adenylate cyclase stimulation of 2,10,11-trihydroxyaporphines in comparison with other hydroxylated aporphines.
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 (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (11.76)18.7374
1990's2 (11.76)18.2507
2000's3 (17.65)29.6817
2010's5 (29.41)24.3611
2020's5 (29.41)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.96

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.

MetricThis Compound (vs All)
Research Demand Index11.96 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index4.85 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.96)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (5.88%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other16 (94.12%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]