Compounds > vobasine
Page last updated: 2024-11-13

vobasine

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Description

vobasine: structure given in first source; RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

vobasine : An indole alkaloid that is vobasan in which the bridgehead methyl group is substituted by a methoxycarbonyl group and an additional oxo substituent is present in the 3-position. [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 CID26195301
CHEMBL ID1628271
MeSH IDM0160247

Synonyms (4)

Synonym
vobasine
CHEMBL1628271
bdbm50378856
methyl (1s,14s,15e,18s)-15-ethylidene-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraene-18-carboxylate
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AcetylcholinesteraseElectrophorus electricus (electric eel)IC50 (µMol)1,000.00000.00000.94539.9400AID526489
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID432709Induction of apoptosis in human HuH7 cells assessed as change in nuclear morphology after 72 hrs using Hoechst staining2009Bioorganic & medicinal chemistry letters, Aug-01, Volume: 19, Issue:15
Induction of apoptosis in HuH-7 cancer cells by monoterpene and beta-carboline indole alkaloids isolated from the leaves of Tabernaemontana elegans.
AID432710Induction of apoptosis in human HuH7 cells assessed as change in nuclear morphology after 24 hrs using Hoechst staining2009Bioorganic & medicinal chemistry letters, Aug-01, Volume: 19, Issue:15
Induction of apoptosis in HuH-7 cancer cells by monoterpene and beta-carboline indole alkaloids isolated from the leaves of Tabernaemontana elegans.
AID432708Induction of apoptosis in human HuH7 cells assessed as change in nuclear morphology after 48 hrs using Hoechst staining2009Bioorganic & medicinal chemistry letters, Aug-01, Volume: 19, Issue:15
Induction of apoptosis in HuH-7 cancer cells by monoterpene and beta-carboline indole alkaloids isolated from the leaves of Tabernaemontana elegans.
AID526489Inhibition of electric eel AChE by Ellman's method2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Indole alkaloids from Ervatamia hainanensis with potent acetylcholinesterase inhibition activities.
AID432712Induction of necrosis in human HuH7 cells2009Bioorganic & medicinal chemistry letters, Aug-01, Volume: 19, Issue:15
Induction of apoptosis in HuH-7 cancer cells by monoterpene and beta-carboline indole alkaloids isolated from the leaves of Tabernaemontana elegans.
AID432711Induction of apoptosis in human HuH7 cells assessed as increase in caspase-3 activity after 12 hrs2009Bioorganic & medicinal chemistry letters, Aug-01, Volume: 19, Issue:15
Induction of apoptosis in HuH-7 cancer cells by monoterpene and beta-carboline indole alkaloids isolated from the leaves of Tabernaemontana elegans.
AID1169800Cytotoxicity against vincristine-resistant human KB/VJ300 cells in presence of vincristine2014Journal of natural products, Nov-26, Volume: 77, Issue:11
Cytotoxic vobasine, tacaman, and corynanthe-tryptamine bisindole alkaloids from Tabernaemontana and structure revision of tronoharine.
AID1169798Cytotoxicity against vincristine-sensitive human KB cells2014Journal of natural products, Nov-26, Volume: 77, Issue:11
Cytotoxic vobasine, tacaman, and corynanthe-tryptamine bisindole alkaloids from Tabernaemontana and structure revision of tronoharine.
AID1169799Cytotoxicity against vincristine-resistant human KB/VJ300 cells2014Journal of natural products, Nov-26, Volume: 77, Issue:11
Cytotoxic vobasine, tacaman, and corynanthe-tryptamine bisindole alkaloids from Tabernaemontana and structure revision of tronoharine.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (15)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (13.33)18.7374
1990's0 (0.00)18.2507
2000's3 (20.00)29.6817
2010's6 (40.00)24.3611
2020's4 (26.67)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 (6.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (93.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
tryptamine
[no description available]		7.110aminoalkylindole;
aralkylamino compound;
indole alkaloid;
tryptamines		human metabolite;
mouse metabolite;
plant metabolite
vincristine
[no description available]		2.110acetate ester;
formamides;
methyl ester;
organic heteropentacyclic compound;
organic heterotetracyclic compound;
tertiary alcohol;
tertiary amino compound;
vinca alkaloid		antineoplastic agent;
drug;
microtubule-destabilising agent;
plant metabolite;
tubulin modulator
galantamine
Galantamine: A benzazepine derived from norbelladine. It is found in GALANTHUS and other AMARYLLIDACEAE. It is a cholinesterase inhibitor that has been used to reverse the muscular effects of GALLAMINE TRIETHIODIDE and TUBOCURARINE and has been studied as a treatment for ALZHEIMER DISEASE and other central nervous system disorders.. galanthamine : A benzazepine alkaloid isolated from certain species of daffodils.		2.0510benzazepine alkaloid fundamental parent;
benzazepine alkaloid;
organic heterotetracyclic compound;
tertiary amino compound		antidote to curare poisoning;
cholinergic drug;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
plant metabolite
vincamine
Vincamine: A major alkaloid of Vinca minor L., Apocynaceae. It has been used therapeutically as a vasodilator and antihypertensive agent, particularly in cerebrovascular disorders.		7.4110alkaloid ester;
hemiaminal;
methyl ester;
organic heteropentacyclic compound;
vinca alkaloid		antihypertensive agent;
metabolite;
vasodilator agent
voacamine
[no description available]		2.0510alkaloid ester;
methyl ester;
monoterpenoid indole alkaloid;
organic heteropentacyclic compound;
tertiary amino compound		angiogenesis inhibitor;
antineoplastic agent;
plant metabolite
gelsedine
gelsedine: isolated from Gelsemium sp.; structure in first source		2.3110
voacamine
voacangine: cleavage product of voacamine		2.1310
ibogaine
Ibogaine: One of several indole alkaloids extracted from Tabernanthe iboga, Baill. It has a complex pharmacological profile, and interacts with multiple systems of neurotransmission. Ibogaine has psychoactive properties and appears to modulate tolerance to opiates.. ibogaine : An organic heteropentacyclic compound that is ibogamine in which the indole hydrogen para to the indole nitrogen has been replaced by a methoxy group.		2.940
catharanthine
[no description available]		2.0810alkaloid ester;
bridged compound;
methyl ester;
monoterpenoid indole alkaloid;
organic heteropentacyclic compound;
tertiary amino compound
coronardine
coronardine: RN given refers to parent cpd without isomeric designation; structure		2.0810alkaloid ester;
methyl ester;
monoterpenoid indole alkaloid;
organic heteropentacyclic compound		antileishmanial agent;
antineoplastic agent;
apoptosis inducer;
plant metabolite
sarpagine
sarpagine: structure in first source. sarpagine : An indole alkaloid that is sarpagan bearing hydroxy groups at positions 10 and 17.		2.3110indole alkaloid;
phenols;
primary alcohol;
secondary amino compound;
tertiary amino compound
voacristine
voacristine: indole alkaloid from leaves of Ervatamia coronaria; RN given for 20(S)-isomer; structure given in first source		2.4920
ibogamine
ibogamine: structure in first source. ibogamine : A monoterpenoid indole alkaloid with formula C19H24N2. It is isolated from the flowering plant genus, Tabernaemontana and exhibits anti-addictive properties.		2.1310
voacamine
voacamine: structure		2.1310
ConditionIndicatedRelationship StrengthStudiesTrials