Page last updated: 2024-12-08

obamegine

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

Description

obamegine: RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID441064
CHEMBL ID452895
CHEBI ID7714
MeSH IDM0106974

Synonyms (23)

Synonym
obamegin
nsc-123123
15,30-diaza-20,25-dimethoxy-15,30-dimethyl-7,23-dioxaheptacyclo[22.6.2.2<3,6>.1<8,12>.1<14,18>.0<22,36>.0<27,31>]hexatriaconta-3(33),4,6(34),8,10,12(35),18(36),19,21,24,26,31-dodecaene-9,21-diol
stepholine
C06513
(+)-obamegine
479-37-8
obamegine
nsc-251534
CHEMBL452895
chebi:7714 ,
nsc 123123
unii-75k1ei2hdp
berbaman-7,12-diol, 6,6'-dimethoxy-2,2'-dimethyl-
75k1ei2hdp ,
16h-1,24:6,9-dietheno-11,15-metheno-2h-pyrido(2',3':17,18)(1,11)dioxacycloeicosino(2,3,4-ij)isoquinoline-12,22-diol, 3,4,4a,5,16a,17,18,19-octahydro-21,26-dimethoxy-4,17-dimethyl-, (4as-(4ar*,16as*))-
obamegine, (+)-
16h-1,24:6,9-dietheno-11,15-metheno-2h-pyrido(2',3':17,18)(1,11)dioxacycloeicosino(2,3,4-ij)isoquinoline-12,22-diol, 3,4,4a,5,16a,17,18,19-octahydro-21,26-dimethoxy-4,17-dimethyl-, (4as,16ar)-
bdbm50508726
obamogenine
Q27107564
DTXSID301098623
(4as,16ar)-3,4,4a,5,16a,17,18,19-octahydro-21,26-dimethoxy-4,17-dimethyl-16h-1,24:6,9-dietheno-11,15-metheno-2h-pyrido[2',3':17,18][1,11]dioxacycloeicosino[2,3,4-ij]isoquinoline-12,22-diol

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Increasing concentrations of thalistyline produced parallel shifts to the right in the dose-response curves of phenylephrine."( A pharmacological study of two bisbenzylisoquinoline alkaloids, thalistyline and obamegine.
Banning, JW; Patil, PN; Salman, KN,
)
0.36
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
isoquinolinesA class of organic heteropolycyclic compound consisting of isoquinoline and its substitution derivatives.
bisbenzylisoquinoline alkaloidA type of benzylisoquinoline alkaloid whose structures are built up of two benzylisoquinoline units linked by ether bridges. Various structural patterns resulting from additional bridging between the two units by direct carbon-carbon bridging or by methylenedioxy groups are common.
[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 (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
CholinesteraseHomo sapiens (human)IC50 (µMol)100.00000.00001.559910.0000AID1537270
AcetylcholinesteraseHomo sapiens (human)IC50 (µMol)97.00000.00000.933210.0000AID1537269
Prolyl endopeptidaseHomo sapiens (human)IC50 (µMol)200.00000.00111.98969.7500AID1537274
[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 (26)

Assay IDTitleYearJournalArticle
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.
AID399500Toxicity in dog at 0.5 to 4 mg/kg, iv
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.
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.
AID399502Cardiovascular effect in anesthetized normotensive iv dosed dog assessed as decrease in heart rate
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.
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.
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.
AID399497Antagonist activity at alpha adrenergic receptor in rabbit aortic strips assessed as decrease in of phenylephrine-induced contraction at 3 X 10'-4 M
AID399501Cardiovascular effect in anesthetized normotensive iv dosed dog assessed as decrease in mean arterial pressure
AID674584Cytotoxicity against human U937 cells assessed as cell growth at 12 uM after 24 hrs by alamar blue assay2012Bioorganic & medicinal chemistry, Aug-01, Volume: 20, Issue:15
Discovery and preliminary SAR of bisbenzylisoquinoline alkaloids as inducers of C/EBPα.
AID674579Cytotoxicity against human U937 cells after 24 hrs by alamar blue assay2012Bioorganic & medicinal chemistry, Aug-01, Volume: 20, Issue:15
Discovery and preliminary SAR of bisbenzylisoquinoline alkaloids as inducers of C/EBPα.
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.
AID399498Antagonist activity at alpha adrenergic receptor in rabbit aortic strips assessed as inhibition of phenylephrine-induced contraction
AID399505Cardiovascular effect in anesthetized normotensive dog assessed as reduction in mean arterial pressure at 2 mg/kg, iv dosed twice with second dose being administered 2.5 hrs interval after the first dose
AID674577Induction of rat C/EBPalpha expression transfected in human U937 cells at 12 uM after 24 hrs by luciferase reporter gene assay relative to ATRA2012Bioorganic & medicinal chemistry, Aug-01, Volume: 20, Issue:15
Discovery and preliminary SAR of bisbenzylisoquinoline alkaloids as inducers of C/EBPα.
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.
AID399496Antagonist activity at alpha adrenergic receptor in rabbit aortic strips assessed as decrease in of phenylephrine-induced contraction at 10'-4 M
AID399799Blockade of neuromuscular transmission activity in albino Sprague-Dawley rat hemidiaphragm assessed as inhibition of electrically-stimulated phrenic nerve contraction at 1 to 30 X 10'-6 M
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.
AID399503Toxicity in iv dosed dog assessed as inhibition of respiration
AID397125Antimalarial activity against Plasmodium falciparum
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.
AID674572Induction of rat C/EBPalpha expression transfected in human U937 cells after 24 hrs by luciferase reporter gene assay relative to ATRA2012Bioorganic & medicinal chemistry, Aug-01, Volume: 20, Issue:15
Discovery and preliminary SAR of bisbenzylisoquinoline alkaloids as inducers of C/EBPα.
AID399504Cardiovascular effect in anesthetized normotensive dog assessed as decrease in mean arterial pressure at 2 mg/kg, iv upto 22 mins
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (20.00)18.2507
2000's1 (20.00)29.6817
2010's2 (40.00)24.3611
2020's1 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (14.29%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]