Page last updated: 2024-12-06

agroclavine

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

Description

agroclavine: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

agroclavine : An ergot alkaloid that is ergoline which contains a double bond between positions 8 and 9, and which is substituted by methyl groups at positions 6 and 8. [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 CID73484
CHEMBL ID449081
CHEBI ID2519
SCHEMBL ID183368
MeSH IDM0045530

Synonyms (41)

Synonym
6,8-dimethyl-8,9-didehydroergoline
EU-0100128
brn 0024966
einecs 208-947-3
nsc 93132
ccris 2099
8,9-didehydro-6,8-dimethylergoline
ergoline, 8,9-didehydro-6,8-dimethyl-
NCGC00015018-01
lopac-a-206
LOPAC0_000128
BPBIO1_001357
BIOMOL-NT_000066
C09023
agroclavine
NCGC00163164-01
MLS001216424
smr000544202
8,9-didehydro-6,8-dimethyl-ergoline
CHEMBL449081 ,
chebi:2519 ,
bdbm50016490
7,9-dimethyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinoline
(6ar,10ar)-7,9-dimethyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinoline
7,9-dimethyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinoline (agroclavine)
cid_73484
CCG-204223
(6ar,10ar)-7,9-dimethyl-4,6,6a,7,8,10a-hexahydroindolo[4,3-fg]quinoline
(-)-agroclavine
(5r,10r)-agroclavine
4-23-00-01623 (beilstein handbook reference)
unii-a8sw57go7t
a8sw57go7t ,
agroclavine [mi]
SCHEMBL183368
XJOOMMHNYOJWCZ-UKRRQHHQSA-N
SR-01000075354-1
sr-01000075354
(6ar,10ar)-7,9-dimethyl-6,6a,8,10a-tetrahydro-4h-indolo[4,3-fg]quinoline
Q4694226
(2r,7r)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0?,?.0??,??]hexadeca-1(15),3,9,12(16),13-pentaene

Research Excerpts

Overview

Agroclavine is a natural, clavine type of ergot alkaloid with D1 dopamine and a-adrenoceptor agonistic properties.

ExcerptReferenceRelevance
"Agroclavine is a natural, clavine type of ergot alkaloid with D1 dopamine and a-adrenoceptor agonistic properties. "( Effect of agroclavine on NK activity in vivo under normal and stress conditions in rats.
Fiserová, A; Krsiak, M; Malek, J; Rosina, J; Starec, M, 2001
)
2.16

Treatment

ExcerptReferenceRelevance
"Agroclavine treatment did not affect the ability of mice to learn and retain a new skill."( [Disruption of spatial memory in mice exposed to agroclavine].
Arinbasarov, MU; Bobkova, NV; Medvinskaia, NI; Nesterova, IV,
)
1.11
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
ergot alkaloid
[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 (35)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency3.54810.003245.467312,589.2998AID2517
Chain A, Beta-lactamaseEscherichia coli K-12Potency39.81070.044717.8581100.0000AID485294
thioredoxin reductaseRattus norvegicus (Norway rat)Potency3.62810.100020.879379.4328AID588453; AID652023
USP1 protein, partialHomo sapiens (human)Potency35.48130.031637.5844354.8130AID743255
GLS proteinHomo sapiens (human)Potency17.78280.35487.935539.8107AID624170
TDP1 proteinHomo sapiens (human)Potency28.28160.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency15.84890.180013.557439.8107AID1460
thioredoxin glutathione reductaseSchistosoma mansoniPotency2.23870.100022.9075100.0000AID485364
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency25.11890.011212.4002100.0000AID1030
67.9K proteinVaccinia virusPotency11.22020.00018.4406100.0000AID720579
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency24.10820.035520.977089.1251AID504332
cytochrome P450 2D6 isoform 1Homo sapiens (human)Potency1.99530.00207.533739.8107AID891
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency50.11870.354828.065989.1251AID504847
importin subunit beta-1 isoform 1Homo sapiens (human)Potency78.11715.804836.130665.1308AID540253; AID540263
flap endonuclease 1Homo sapiens (human)Potency50.11870.133725.412989.1251AID588795
serine/threonine-protein kinase PLK1Homo sapiens (human)Potency26.67950.168316.404067.0158AID720504
snurportin-1Homo sapiens (human)Potency78.11715.804836.130665.1308AID540253; AID540263
histone-lysine N-methyltransferase 2A isoform 2 precursorHomo sapiens (human)Potency31.62280.010323.856763.0957AID2662
peptidyl-prolyl cis-trans isomerase NIMA-interacting 1Homo sapiens (human)Potency67.45550.425612.059128.1838AID504891
tumor susceptibility gene 101 proteinHomo sapiens (human)Potency39.59070.129810.833132.6090AID493005; AID651600
GTP-binding nuclear protein Ran isoform 1Homo sapiens (human)Potency56.23415.804816.996225.9290AID540253
muscleblind-like protein 1 isoform 1Homo sapiens (human)Potency11.22020.00419.962528.1838AID2675
D(3) dopamine receptor isoform eHomo sapiens (human)Potency0.08910.02009.148539.8107AID720506
DNA dC->dU-editing enzyme APOBEC-3F isoform aHomo sapiens (human)Potency15.84890.025911.239831.6228AID602313
Inositol monophosphatase 1Rattus norvegicus (Norway rat)Potency31.62281.000010.475628.1838AID1457
[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)
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)IC50 (µMol)0.14000.00031.38338.4000AID3674
D(2) dopamine receptorBos taurus (cattle)IC50 (µMol)0.89000.00100.79948.0000AID62164
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)IC50 (µMol)0.14000.00051.48357.8000AID3674
5-hydroxytryptamine receptor 1DRattus norvegicus (Norway rat)IC50 (µMol)0.14000.00311.73607.8000AID3674
5-hydroxytryptamine receptor 1FRattus norvegicus (Norway rat)IC50 (µMol)0.14000.00501.79627.8000AID3674
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
POsterior SegregationCaenorhabditis elegansEC50 (µMol)11.17402.201047.1808186.6810AID1964
Sodium-dependent noradrenaline transporter Homo sapiens (human)EC50 (µMol)8.67200.082031.0243168.9080AID1960
Zinc finger protein mex-5Caenorhabditis elegansEC50 (µMol)8.67200.082033.5679168.9080AID1960
[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)
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)AC5038.41001.67009.266943.4100AID588683
kelch-like ECH-associated protein 1Homo sapiens (human)AC5038.41001.67009.266943.4100AID588683
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

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)
monoamine transportSodium-dependent noradrenaline transporter Homo sapiens (human)
neurotransmitter transportSodium-dependent noradrenaline transporter Homo sapiens (human)
chemical synaptic transmissionSodium-dependent noradrenaline transporter Homo sapiens (human)
response to xenobiotic stimulusSodium-dependent noradrenaline transporter Homo sapiens (human)
response to painSodium-dependent noradrenaline transporter Homo sapiens (human)
norepinephrine uptakeSodium-dependent noradrenaline transporter Homo sapiens (human)
neuron cellular homeostasisSodium-dependent noradrenaline transporter Homo sapiens (human)
amino acid transportSodium-dependent noradrenaline transporter Homo sapiens (human)
norepinephrine transportSodium-dependent noradrenaline transporter Homo sapiens (human)
dopamine uptake involved in synaptic transmissionSodium-dependent noradrenaline transporter Homo sapiens (human)
sodium ion transmembrane transportSodium-dependent noradrenaline transporter Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
actin bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
neurotransmitter transmembrane transporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
neurotransmitter:sodium symporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
dopamine:sodium symporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
norepinephrine:sodium symporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
protein bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
monoamine transmembrane transporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
alpha-tubulin bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
metal ion bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
beta-tubulin bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
Golgi membraneD(2) dopamine receptorBos taurus (cattle)
plasma membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
cell surfaceSodium-dependent noradrenaline transporter Homo sapiens (human)
membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
neuronal cell body membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
presynaptic membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
plasma membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
axonSodium-dependent noradrenaline transporter Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (32)

Assay IDTitleYearJournalArticle
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.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings 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.
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.
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.
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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
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.
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.
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.
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.
AID224447Inhibition of p74 Blk tyrosine kinase autophosphorylation (Inactive)1998Bioorganic & medicinal chemistry letters, Mar-17, Volume: 8, Issue:6
1-Methoxy-agroclavine from Penicillium sp. WC75209, a novel inhibitor of the Lck tyrosine kinase.
AID190397Evaluated for the Average turns per first 15 minutes after administration of 1 mg/kg intraperitoneally1980Journal of medicinal chemistry, Jul, Volume: 23, Issue:7
Conversion of ergolines to hexahydro- and octahydrobenzo[f]quinolines (depyrroloergolines).
AID3674Tested for its binding affinity towards 5-hydroxytryptamine 1 receptor in rat cortical membrane homogenates using radioligand ([3H]5-HT) binding assay.1988Journal of medicinal chemistry, Aug, Volume: 31, Issue:8
Ergolines as selective 5-HT1 agonists.
AID233089Ratio of affinity towards 5-HT1 to 5-HT2 receptor1988Journal of medicinal chemistry, Aug, Volume: 31, Issue:8
Ergolines as selective 5-HT1 agonists.
AID189493Evaluated for the rat turning after administration of 1 mg/kg intraperitoneally1980Journal of medicinal chemistry, Jul, Volume: 23, Issue:7
Conversion of ergolines to hexahydro- and octahydrobenzo[f]quinolines (depyrroloergolines).
AID4788Binding affinity at 5-hydroxytryptamine 2 receptor from rat frontal cortex homogenates by [3H]-spiperone displacement.1988Journal of medicinal chemistry, Aug, Volume: 31, Issue:8
Ergolines as selective 5-HT1 agonists.
AID224446Inhibition of p72 syk autophosphorylation (Inactive)1998Bioorganic & medicinal chemistry letters, Mar-17, Volume: 8, Issue:6
1-Methoxy-agroclavine from Penicillium sp. WC75209, a novel inhibitor of the Lck tyrosine kinase.
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.
AID162620Evaluated for the prolactin inhibition at the dose 50 ug/kg administered intraperitoneally1980Journal of medicinal chemistry, Jul, Volume: 23, Issue:7
Conversion of ergolines to hexahydro- and octahydrobenzo[f]quinolines (depyrroloergolines).
AID162621Evaluated for the prolactin inhibition at the dose 50 ug/kg administered intraperitoneally (treatment)1980Journal of medicinal chemistry, Jul, Volume: 23, Issue:7
Conversion of ergolines to hexahydro- and octahydrobenzo[f]quinolines (depyrroloergolines).
AID227700Anticonvulsant activity2003Bioorganic & medicinal chemistry letters, Aug-18, Volume: 13, Issue:16
Topological virtual screening: a way to find new anticonvulsant drugs from chemical diversity.
AID224286Inhibition of p56 lck autophosphorylation, gamma-[33P]ATP incorporation (Inactive)1998Bioorganic & medicinal chemistry letters, Mar-17, Volume: 8, Issue:6
1-Methoxy-agroclavine from Penicillium sp. WC75209, a novel inhibitor of the Lck tyrosine kinase.
AID62164Competition in vitro with the dopamine receptor D2 antagonist [3H]spiperone, for binding sites on calf caudate membranes.1993Journal of medicinal chemistry, Apr-02, Volume: 36, Issue:7
Synthesis and dopamine antagonist activity of 2-thioether derivatives of the ergoline ring system.
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 (37)

TimeframeStudies, This Drug (%)All Drugs %
pre-199010 (27.03)18.7374
1990's5 (13.51)18.2507
2000's12 (32.43)29.6817
2010's6 (16.22)24.3611
2020's4 (10.81)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.11

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 Index24.11 (24.57)
Research Supply Index3.87 (2.92)
Research Growth Index4.65 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.11)

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%
Other47 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]