Page last updated: 2024-12-08

aromoline

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Description

aromoline: from roots of Stephania cepharantha; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
StephaniagenusA plant genus of the family MENISPERMACEAE. Members contain cycleanine.[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]
StephaniagenusA plant genus of the family MENISPERMACEAE. Members contain cycleanine.[MeSH]MenispermaceaeA plant family of the order Ranunculales, subclass Magnoliidae, class Magnoliopsida. Members are mostly vines and shrubs and they contain isoquinoline alkaloids, some of which have been used as arrow poisons.[MeSH]

Cross-References

ID SourceID
PubMed CID362574
CHEMBL ID508781
MeSH IDM0182082

Synonyms (22)

Synonym
nsc-93674
nsc-626657
oxyacanthan-7, 6,6'-dimethoxy-2,2'-dimethyl-
brn 4649148
nsc 93674
n-methyldaphnoline
oxyacanthan-7,12'-diol, 6,6'-dimethoxy-2,2'-dimethyl-
promoline
thalicrine
nsc 626657
NSC626657 ,
519-53-9
aromoline
(+)-aromoline
CHEMBL508781 ,
dhu37v4q3q ,
unii-dhu37v4q3q
2h-1,24:12,15-dietheno-6,10-metheno-16h-pyrido(2',3':17,18)(1,10)dioxacycloeicosino(2,3,4-ij)isoquinoline-9,22-diol, 3,4,4a,5,16a,17,18,19-octahydro-21,26-dimethoxy-4,17-dimethyl-, (4ar-(4ar*,16as*))-
2h-1,24:12,15-dietheno-6,10-metheno-16h-pyrido(2',3':17,18)(1,10)dioxacycloeicosino(2,3,4-ij)isoquinoline-9,22-diol, 3,4,4a,5,16a,17,18,19-octahydro-21,26-dimethoxy-4,17-dimethyl-, (4ar,16as)-
aromoline, (+)-
bdbm50508727
(1r,14s)-20,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.29,12.13,7.114,18.027,31.022,33]hexatriaconta-3(36),4,6,9(35),10,12(34),18,20,22(33),24,26,31-dodecaene-6,21-diol
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
CholinesteraseHomo sapiens (human)IC50 (µMol)0.80000.00001.559910.0000AID1537270
CholinesteraseHomo sapiens (human)Ki23.05500.00001.51739.7300AID1537272; AID1537273
AcetylcholinesteraseHomo sapiens (human)IC50 (µMol)100.00000.00000.933210.0000AID1537269
Prolyl endopeptidaseHomo sapiens (human)IC50 (µMol)189.00000.00111.98969.7500AID1537274
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (26)

Processvia Protein(s)Taxonomy
xenobiotic metabolic processCholinesteraseHomo sapiens (human)
learningCholinesteraseHomo sapiens (human)
negative regulation of cell population proliferationCholinesteraseHomo sapiens (human)
neuroblast differentiationCholinesteraseHomo sapiens (human)
peptide hormone processingCholinesteraseHomo sapiens (human)
response to alkaloidCholinesteraseHomo sapiens (human)
cocaine metabolic processCholinesteraseHomo sapiens (human)
negative regulation of synaptic transmissionCholinesteraseHomo sapiens (human)
response to glucocorticoidCholinesteraseHomo sapiens (human)
response to folic acidCholinesteraseHomo sapiens (human)
choline metabolic processCholinesteraseHomo sapiens (human)
acetylcholine catabolic processCholinesteraseHomo sapiens (human)
acetylcholine catabolic process in synaptic cleftAcetylcholinesteraseHomo sapiens (human)
regulation of receptor recyclingAcetylcholinesteraseHomo sapiens (human)
osteoblast developmentAcetylcholinesteraseHomo sapiens (human)
acetylcholine catabolic processAcetylcholinesteraseHomo sapiens (human)
cell adhesionAcetylcholinesteraseHomo sapiens (human)
nervous system developmentAcetylcholinesteraseHomo sapiens (human)
synapse assemblyAcetylcholinesteraseHomo sapiens (human)
receptor internalizationAcetylcholinesteraseHomo sapiens (human)
negative regulation of synaptic transmission, cholinergicAcetylcholinesteraseHomo sapiens (human)
amyloid precursor protein metabolic processAcetylcholinesteraseHomo sapiens (human)
positive regulation of protein secretionAcetylcholinesteraseHomo sapiens (human)
retina development in camera-type eyeAcetylcholinesteraseHomo sapiens (human)
acetylcholine receptor signaling pathwayAcetylcholinesteraseHomo sapiens (human)
positive regulation of cold-induced thermogenesisAcetylcholinesteraseHomo sapiens (human)
proteolysisProlyl endopeptidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (18)

Processvia Protein(s)Taxonomy
amyloid-beta bindingCholinesteraseHomo sapiens (human)
catalytic activityCholinesteraseHomo sapiens (human)
acetylcholinesterase activityCholinesteraseHomo sapiens (human)
cholinesterase activityCholinesteraseHomo sapiens (human)
protein bindingCholinesteraseHomo sapiens (human)
hydrolase activity, acting on ester bondsCholinesteraseHomo sapiens (human)
enzyme bindingCholinesteraseHomo sapiens (human)
choline bindingCholinesteraseHomo sapiens (human)
identical protein bindingCholinesteraseHomo sapiens (human)
amyloid-beta bindingAcetylcholinesteraseHomo sapiens (human)
acetylcholinesterase activityAcetylcholinesteraseHomo sapiens (human)
cholinesterase activityAcetylcholinesteraseHomo sapiens (human)
protein bindingAcetylcholinesteraseHomo sapiens (human)
collagen bindingAcetylcholinesteraseHomo sapiens (human)
hydrolase activityAcetylcholinesteraseHomo sapiens (human)
serine hydrolase activityAcetylcholinesteraseHomo sapiens (human)
acetylcholine bindingAcetylcholinesteraseHomo sapiens (human)
protein homodimerization activityAcetylcholinesteraseHomo sapiens (human)
laminin bindingAcetylcholinesteraseHomo sapiens (human)
serine-type endopeptidase activityProlyl endopeptidaseHomo sapiens (human)
protein bindingProlyl endopeptidaseHomo sapiens (human)
serine-type peptidase activityProlyl endopeptidaseHomo sapiens (human)
oligopeptidase activityProlyl endopeptidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (18)

Processvia Protein(s)Taxonomy
extracellular regionCholinesteraseHomo sapiens (human)
nuclear envelope lumenCholinesteraseHomo sapiens (human)
endoplasmic reticulum lumenCholinesteraseHomo sapiens (human)
blood microparticleCholinesteraseHomo sapiens (human)
plasma membraneCholinesteraseHomo sapiens (human)
extracellular spaceCholinesteraseHomo sapiens (human)
extracellular regionAcetylcholinesteraseHomo sapiens (human)
basement membraneAcetylcholinesteraseHomo sapiens (human)
extracellular spaceAcetylcholinesteraseHomo sapiens (human)
nucleusAcetylcholinesteraseHomo sapiens (human)
Golgi apparatusAcetylcholinesteraseHomo sapiens (human)
plasma membraneAcetylcholinesteraseHomo sapiens (human)
cell surfaceAcetylcholinesteraseHomo sapiens (human)
membraneAcetylcholinesteraseHomo sapiens (human)
neuromuscular junctionAcetylcholinesteraseHomo sapiens (human)
synaptic cleftAcetylcholinesteraseHomo sapiens (human)
synapseAcetylcholinesteraseHomo sapiens (human)
perinuclear region of cytoplasmAcetylcholinesteraseHomo sapiens (human)
side of membraneAcetylcholinesteraseHomo sapiens (human)
nucleusProlyl endopeptidaseHomo sapiens (human)
cytoplasmProlyl endopeptidaseHomo sapiens (human)
cytosolProlyl endopeptidaseHomo sapiens (human)
membraneProlyl endopeptidaseHomo sapiens (human)
cytosolProlyl endopeptidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID377945Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum D6 infected human erythrocytes as [3H]hypoxanthine uptake after 24 hrs1999Journal of natural products, Jan, Volume: 62, Issue:1
Antiplasmodial and cytotoxic activity of natural bisbenzylisoquinoline alkaloids.
AID1537272Mixed-type inhibition of human BuChE assessed as enzyme-inhibitor complex using butyrylthiocholine iodide as substrate by Lineweaver-Burk plot analysis2019Journal of natural products, 02-22, Volume: 82, Issue:2
Isoquinoline Alkaloids from Berberis vulgaris as Potential Lead Compounds for the Treatment of Alzheimer's Disease.
AID1537277Permeability of the compound after 2.45 hrs by PAMPA2019Journal of natural products, 02-22, Volume: 82, Issue:2
Isoquinoline Alkaloids from Berberis vulgaris as Potential Lead Compounds for the Treatment of Alzheimer's Disease.
AID1537273Mixed-type inhibition of human BuChE assessed as enzyme-substrate-inhibitor complex using butyrylthiocholine iodide as substrate by Lineweaver-Burk plot analysis2019Journal of natural products, 02-22, Volume: 82, Issue:2
Isoquinoline Alkaloids from Berberis vulgaris as Potential Lead Compounds for the Treatment of Alzheimer's Disease.
AID377944Cytotoxicity against human KB cells after 72 hrs by SRB assay1999Journal of natural products, Jan, Volume: 62, Issue:1
Antiplasmodial and cytotoxic activity of natural bisbenzylisoquinoline alkaloids.
AID1537276Inhibition of GSK3B (unknown origin) at 10 uM relative to control2019Journal of natural products, 02-22, Volume: 82, Issue:2
Isoquinoline Alkaloids from Berberis vulgaris as Potential Lead Compounds for the Treatment of Alzheimer's Disease.
AID1537269Inhibition of human AChE using acetylthiocholine iodide as substrate measured for 1 min by Ellman's method2019Journal of natural products, 02-22, Volume: 82, Issue:2
Isoquinoline Alkaloids from Berberis vulgaris as Potential Lead Compounds for the Treatment of Alzheimer's Disease.
AID377946Selectivity index, ratio of ED50 for human KB cells to IC50 for chloroquine-sensitive Plasmodium falciparum D61999Journal of natural products, Jan, Volume: 62, Issue:1
Antiplasmodial and cytotoxic activity of natural bisbenzylisoquinoline alkaloids.
AID1537271Selectivity index, ratio of IC50 for human BuChE to IC50 for human AChE2019Journal of natural products, 02-22, Volume: 82, Issue:2
Isoquinoline Alkaloids from Berberis vulgaris as Potential Lead Compounds for the Treatment of Alzheimer's Disease.
AID377947Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2 infected human erythrocytes as [3H]hypoxanthine uptake after 24 hrs1999Journal of natural products, Jan, Volume: 62, Issue:1
Antiplasmodial and cytotoxic activity of natural bisbenzylisoquinoline alkaloids.
AID377948Selectivity index, ratio of ED50 for human KB cells to IC50 for chloroquine-sensitive Plasmodium falciparum W21999Journal of natural products, Jan, Volume: 62, Issue:1
Antiplasmodial and cytotoxic activity of natural bisbenzylisoquinoline alkaloids.
AID1537274Inhibition of POP (unknown origin) using (Z)-Gly-Pro-p-nitroanilide as substrate preincubated for 5 mins followed by substrate addition and measured after 30 mins by spectrophotometric method2019Journal of natural products, 02-22, Volume: 82, Issue:2
Isoquinoline Alkaloids from Berberis vulgaris as Potential Lead Compounds for the Treatment of Alzheimer's Disease.
AID1537270Inhibition of human BuChE using butyrylthiocholine iodide as substrate measured for 1 min by Ellman's method2019Journal of natural products, 02-22, Volume: 82, Issue:2
Isoquinoline Alkaloids from Berberis vulgaris as Potential Lead Compounds for the Treatment of Alzheimer's Disease.
AID1224817Assays to identify small molecules inhibitory for eIF4E expression2015Chemistry & biology, Jul-23, Volume: 22, Issue:7
Internal Ribosome Entry Site-Based Bicistronic In Situ Reporter Assays for Discovery of Transcription-Targeted Lead Compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (33.33)18.2507
2000's2 (33.33)29.6817
2010's2 (33.33)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: 17.74

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 Index17.74 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.74)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]