Compounds > crispine a
Page last updated: 2024-11-12

crispine a

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

Description

crispine A: pyrrolo(2,1-a)isoquinoline alkaloid from Carduus crispus; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
CarduusgenusA plant genus of the family ASTERACEAE. Members contain arctiin and onopordopicrin.[MeSH]AsteraceaeA large plant family of the order Asterales, subclass Asteridae, class Magnoliopsida. The family is also known as Compositae. Flower petals are joined near the base and stamens alternate with the corolla lobes. The common name of daisy refers to several genera of this family including Aster; CHRYSANTHEMUM; RUDBECKIA; TANACETUM.[MeSH]

Cross-References

ID SourceID
PubMed CID10263398
CHEMBL ID3235509
MeSH IDM0514756

Synonyms (8)

Synonym
inchi=1/c14h19no2/c1-16-13-8-10-5-7-15-6-3-4-12(15)11(10)9-14(13)17-2/h8-9,12h,3-7h2,1-2h
8,9-dimethoxy-2,3,4,5,6,10b-hexahydro-1h-pyrrolo[2,1-a]isoquinoline
8,9-DIMETHOXY-1,2,3,5,6,10B-HEXAHYDROPYRROLO[2,1-A]ISOQUINOLINE ,
15889-93-7
1,2,3,5,6,10b-hexahydro-8,9-dimethoxypyrrolo[2,1-a]isoquinoline
crispine a
CHEMBL3235509 ,
bdbm50006633
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (7)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Neuronal acetylcholine receptor subunit alpha-3Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00300.77706.0000AID1127788; AID1489907
Neuronal acetylcholine receptor subunit alpha-3Rattus norvegicus (Norway rat)Ki200.00000.00000.352210.0000AID1127785; AID1489903
Neuronal acetylcholine receptor subunit alpha-4Rattus norvegicus (Norway rat)Ki52.52500.00000.12345.5000AID1127783; AID1127784; AID1489901; AID1489902
Neuronal acetylcholine receptor subunit beta-2Rattus norvegicus (Norway rat)Ki5.05000.00000.10825.5000AID1127783; AID1489901
Neuronal acetylcholine receptor subunit beta-4Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00300.88696.0000AID1127788; AID1489907
Neuronal acetylcholine receptor subunit beta-4Rattus norvegicus (Norway rat)Ki150.00000.00000.296310.0000AID1127784; AID1127785; AID1489902; AID1489903
Neuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)IC50 (µMol)100.00000.00204.15279.9000AID1489909
Neuronal acetylcholine receptor subunit beta-4Mus musculus (house mouse)IC50 (µMol)30.50000.00400.60201.2000AID1127787; AID1489908
Neuronal acetylcholine receptor subunit beta-2Mus musculus (house mouse)IC50 (µMol)30.50000.00400.60201.2000AID1127787; AID1489908
[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)
Neuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)EC50 (µMol)100.00000.12802.80188.9000AID1489910
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (38)

Processvia Protein(s)Taxonomy
negative regulation of tumor necrosis factor productionNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
response to hypoxiaNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of protein phosphorylationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
monoatomic ion transportNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
calcium ion transportNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
intracellular calcium ion homeostasisNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
signal transductionNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
synaptic transmission, cholinergicNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
learning or memoryNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
memoryNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
short-term memoryNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of cell population proliferationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
negative regulation of tumor necrosis factor productionNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
monoatomic ion transmembrane transportNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
response to nicotineNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of MAPK cascadeNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of angiogenesisNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
synapse organizationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
cognitionNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
sensory processingNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of protein metabolic processNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
excitatory postsynaptic potentialNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
calcium ion transmembrane transportNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
acetylcholine receptor signaling pathwayNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
dendritic spine organizationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
modulation of excitatory postsynaptic potentialNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
dendrite arborizationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of long-term synaptic potentiationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of amyloid-beta formationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
negative regulation of amyloid-beta formationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
regulation of amyloid precursor protein catabolic processNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
response to amyloid-betaNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
response to acetylcholineNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
regulation of amyloid fibril formationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of CoA-transferase activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of excitatory postsynaptic potentialNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
regulation of membrane potentialNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
chemical synaptic transmissionNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
amyloid-beta bindingNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
monoatomic ion channel activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
calcium channel activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
protein bindingNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
acetylcholine receptor activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
toxic substance bindingNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
chloride channel regulator activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
acetylcholine-gated monoatomic cation-selective channel activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
acetylcholine bindingNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
protein homodimerization activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
plasma membraneNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
membraneNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
plasma membrane raftNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
postsynaptic membraneNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
postsynapseNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
acetylcholine-gated channel complexNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
plasma membraneNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
neuron projectionNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
synapseNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID1489903Displacement of [3H]epibatidine from rat alpha3beta4 nAChR expressed in HEK293 cell membranes after 4 hrs by scintillation counting method2018Journal of medicinal chemistry, 02-22, Volume: 61, Issue:4
Dual Nicotinic Acetylcholine Receptor α4β2 Antagonists/α7 Agonists: Synthesis, Docking Studies, and Pharmacological Evaluation of Tetrahydroisoquinolines and Tetrahydroisoquinolinium Salts.
AID1489909Antagonist activity at human alpha7 nAChR expressed in HEK293 cells co-expressing Ric-3/NACHO assessed as inhibition of ACh-induced calcium mobilization measured up to 90 secs in presence of PNU-120596 by FLIPR assay2018Journal of medicinal chemistry, 02-22, Volume: 61, Issue:4
Dual Nicotinic Acetylcholine Receptor α4β2 Antagonists/α7 Agonists: Synthesis, Docking Studies, and Pharmacological Evaluation of Tetrahydroisoquinolines and Tetrahydroisoquinolinium Salts.
AID1127783Displacement of [3H]epibatidine from rat alpha4/beta2 nAChR expressed in HEK293 cells2013Journal of medicinal chemistry, Dec-12, Volume: 56, Issue:23
Design, synthesis, and biological evaluation of Erythrina alkaloid analogues as neuronal nicotinic acetylcholine receptor antagonists.
AID1127784Displacement of [3H]epibatidine from rat alpha4/beta4 nAChR expressed in HEK293 cells2013Journal of medicinal chemistry, Dec-12, Volume: 56, Issue:23
Design, synthesis, and biological evaluation of Erythrina alkaloid analogues as neuronal nicotinic acetylcholine receptor antagonists.
AID1127787Antagonist activity at mouse alpha4/beta2 nAChR expressed in HEK293 cells assessed as inhibition of (S)-nicotine-induced activity by FLIPR membrane potential blue assay2013Journal of medicinal chemistry, Dec-12, Volume: 56, Issue:23
Design, synthesis, and biological evaluation of Erythrina alkaloid analogues as neuronal nicotinic acetylcholine receptor antagonists.
AID1127788Antagonist activity at rat alpha3/beta4 nAChR expressed in HEK293 cells assessed as inhibition of (S)-nicotine-induced activity by FLIPR membrane potential blue assay2013Journal of medicinal chemistry, Dec-12, Volume: 56, Issue:23
Design, synthesis, and biological evaluation of Erythrina alkaloid analogues as neuronal nicotinic acetylcholine receptor antagonists.
AID1489908Antagonist activity at mouse alpha4beta2 nAChR expressed in HEK293 cells assessed as inhibition of (S)-nicotine-induced current response measured up to 90 secs by FMP assay2018Journal of medicinal chemistry, 02-22, Volume: 61, Issue:4
Dual Nicotinic Acetylcholine Receptor α4β2 Antagonists/α7 Agonists: Synthesis, Docking Studies, and Pharmacological Evaluation of Tetrahydroisoquinolines and Tetrahydroisoquinolinium Salts.
AID1489910Agonist activity at human alpha7 nAChR expressed in HEK293 cells co-expressing Ric-3/NACHO assessed as induction of calcium mobilization measured up to 90 secs in presence of PNU-120596 by FLIPR assay2018Journal of medicinal chemistry, 02-22, Volume: 61, Issue:4
Dual Nicotinic Acetylcholine Receptor α4β2 Antagonists/α7 Agonists: Synthesis, Docking Studies, and Pharmacological Evaluation of Tetrahydroisoquinolines and Tetrahydroisoquinolinium Salts.
AID1489902Displacement of [3H]epibatidine from rat alpha4beta4 nAChR expressed in HEK293 cell membranes after 4 hrs by scintillation counting method2018Journal of medicinal chemistry, 02-22, Volume: 61, Issue:4
Dual Nicotinic Acetylcholine Receptor α4β2 Antagonists/α7 Agonists: Synthesis, Docking Studies, and Pharmacological Evaluation of Tetrahydroisoquinolines and Tetrahydroisoquinolinium Salts.
AID1127785Displacement of [3H]epibatidine from rat alpha3/beta4 nAChR expressed in HEK293 cells2013Journal of medicinal chemistry, Dec-12, Volume: 56, Issue:23
Design, synthesis, and biological evaluation of Erythrina alkaloid analogues as neuronal nicotinic acetylcholine receptor antagonists.
AID1127786Displacement of [3H]MLA from rat/mouse alpha7 nAChR/5HT3A expressed in tsA201 cells2013Journal of medicinal chemistry, Dec-12, Volume: 56, Issue:23
Design, synthesis, and biological evaluation of Erythrina alkaloid analogues as neuronal nicotinic acetylcholine receptor antagonists.
AID1489901Displacement of [3H]epibatidine from rat alpha4beta2 nAChR expressed in HEK293 cell membranes after 4 hrs by scintillation counting method2018Journal of medicinal chemistry, 02-22, Volume: 61, Issue:4
Dual Nicotinic Acetylcholine Receptor α4β2 Antagonists/α7 Agonists: Synthesis, Docking Studies, and Pharmacological Evaluation of Tetrahydroisoquinolines and Tetrahydroisoquinolinium Salts.
AID1489907Antagonist activity at rat alpha3beta4 nAChR expressed in HEK293 cells assessed as inhibition of (S)-nicotine-induced current response measured up to 90 secs by FMP assay2018Journal of medicinal chemistry, 02-22, Volume: 61, Issue:4
Dual Nicotinic Acetylcholine Receptor α4β2 Antagonists/α7 Agonists: Synthesis, Docking Studies, and Pharmacological Evaluation of Tetrahydroisoquinolines and Tetrahydroisoquinolinium Salts.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (23.08)29.6817
2010's10 (76.92)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.33

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 Index17.33 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.78 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.33)

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%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
tyrosine
Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.		2.0610amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
proteinogenic amino acid;
tyrosine		EC 1.3.1.43 (arogenate dehydrogenase) inhibitor;
fundamental metabolite;
micronutrient;
nutraceutical
2-naphthol
2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.		2.110naphtholantinematodal drug;
genotoxin;
human urinary metabolite;
human xenobiotic metabolite;
mouse metabolite;
radical scavenger
laudanosine
laudanosine: opium alkaloid		2.1710isoquinolines
palladium
Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.		2.0610metal allergen;
nickel group element atom;
platinum group metal atom
dihydro-beta-erythroidine
Dihydro-beta-Erythroidine: Dihydro analog of beta-erythroidine, which is isolated from the seeds and other plant parts of Erythrina sp. Leguminosae. It is an alkaloid with curarimimetic properties.. dihydro-beta-erythroidine : An organic heterotetracyclic compound resulting from the partial hydrogenation of the 1,3-diene moiety of beta-erythroidine to give the corresponding 2-ene.		2.0810delta-lactone;
organic heterotetracyclic compound;
tertiary amino compound		nicotinic antagonist
erysodine
erysodine: structure given in first source. erysodine : An erythrina alkaloid with formula C18H21NO3 isolated from several erythrina plant species. It is a competitive antagonist of nicotinic acetylcholine receptors and exhibits antiparasitic and insecticidal activities.		2.5220aromatic ether;
diether;
Erythrina alkaloid;
organic heterotetracyclic compound;
phenols		antiparasitic agent;
nicotinic antagonist;
phytogenic insecticide
n-boc-pyrrolidine
N-Boc-pyrrolidine: structure in first source		2.0610
altinicline maleate
altinicline maleate: binds to neuronal nicotinic acetylcholine receptors		2.0610
almorexant
almorexant: a dual orexin receptor antagonist for treatment of insomnia		2.110isoquinolines
ConditionIndicatedRelationship StrengthStudiesTrials