Compounds > sinococuline
Page last updated: 2024-12-11

sinococuline

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

Description

sinococuline: isolated from Stephania sutchuenensis; RN given for (6beta,7beta,9alpha,13alpha)-isomer; structure 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 CID5489400
CHEMBL ID524026
SCHEMBL ID166476
MeSH IDM0260247

Synonyms (19)

Synonym
sinococuline
bdbm50260779
CHEMBL524026 ,
j5624pb437 ,
109351-36-2
unii-j5624pb437
(6beta,7beta,9alpha,13alpha)-8,14-didehydro-3,8-dimethoxymorphinan-4,6,7-triol
morphinan-4,6,7-triol, 8,14-didehydro-3,8-dimethoxy-, (6beta,7beta,9alpha,13alpha)-
SCHEMBL166476
DTXSID00911127
(1s,9s,12s,13s)-4,11-dimethoxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,10-tetraene-3,12,13-triol
Q15427859
morphinan-4,6,7-triol, 8,14-didehydro-3,8-dimethoxy-, (6.beta.,7.beta.,9.alpha.,13.alpha.)-
alkaloid fk1000
fk-1000
(1s,9s,12s,13s)-4,11-dimethoxy-17-azatetracyclo(7.5.3.0^(1,10).0^(2,7))heptadeca-2(7),3,5,10-tetraene-3,12,13-triol
(6.beta.,7.beta.,9.alpha.,13.alpha.)-8,14-didehydro-3,8-dimethoxymorphinan-4,6,7-triol
AKOS040763319
F92832

Research Excerpts

Overview

Sinococuline is an effective tumor cell growth inhibitor. The toxicity of aknadinine and 1-nitroaknadinine towards all tested cells is low.

ExcerptReferenceRelevance
"Sinococuline is an effective tumor cell growth inhibitor whereas the toxicity of aknadinine and 1-nitroaknadinine towards all tested cells is low."( Cytotoxic effects of sinococuline.
Che, CT; Liu, WK; Wang, XK, 1996)		1.33

Treatment

ExcerptReferenceRelevance
"The treatment with Sinococuline at 2.0 mg/kg/day; BID (twice a day), was the most effective in protecting the severely DENV-infected AG129 mice."( Sinococuline, a bioactive compound of Cocculus hirsutus has potent anti-dengue activity.
Aggarwal, C; Ahuja, R; Arora, U; Beesetti, H; Chaturvedi, S; Garg, A; Khanna, N; Lal, AA; Nayyar, K; Shukla, R, 2023)		2.67
[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)
Delta-type opioid receptorHomo sapiens (human)IC50 (µMol)37.00000.00020.75218.0140AID480387
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (19)

Processvia Protein(s)Taxonomy
immune responseDelta-type opioid receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerDelta-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
adult locomotory behaviorDelta-type opioid receptorHomo sapiens (human)
negative regulation of gene expressionDelta-type opioid receptorHomo sapiens (human)
negative regulation of protein-containing complex assemblyDelta-type opioid receptorHomo sapiens (human)
positive regulation of CREB transcription factor activityDelta-type opioid receptorHomo sapiens (human)
positive regulation of peptidyl-serine phosphorylationDelta-type opioid receptorHomo sapiens (human)
response to nicotineDelta-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
eating behaviorDelta-type opioid receptorHomo sapiens (human)
regulation of mitochondrial membrane potentialDelta-type opioid receptorHomo sapiens (human)
regulation of calcium ion transportDelta-type opioid receptorHomo sapiens (human)
cellular response to growth factor stimulusDelta-type opioid receptorHomo sapiens (human)
cellular response to hypoxiaDelta-type opioid receptorHomo sapiens (human)
cellular response to toxic substanceDelta-type opioid receptorHomo sapiens (human)
neuropeptide signaling pathwayDelta-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
G protein-coupled opioid receptor activityDelta-type opioid receptorHomo sapiens (human)
protein bindingDelta-type opioid receptorHomo sapiens (human)
receptor serine/threonine kinase bindingDelta-type opioid receptorHomo sapiens (human)
G protein-coupled enkephalin receptor activityDelta-type opioid receptorHomo sapiens (human)
neuropeptide bindingDelta-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
plasma membraneDelta-type opioid receptorHomo sapiens (human)
synaptic vesicle membraneDelta-type opioid receptorHomo sapiens (human)
dendrite membraneDelta-type opioid receptorHomo sapiens (human)
presynaptic membraneDelta-type opioid receptorHomo sapiens (human)
axon terminusDelta-type opioid receptorHomo sapiens (human)
spine apparatusDelta-type opioid receptorHomo sapiens (human)
postsynaptic density membraneDelta-type opioid receptorHomo sapiens (human)
neuronal dense core vesicleDelta-type opioid receptorHomo sapiens (human)
plasma membraneDelta-type opioid receptorHomo sapiens (human)
neuron projectionDelta-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID480389Displacement of [3H]naloxone from kappa opioid receptor expressed in HEK293 cell membrane at 10 uM2010Journal of natural products, May-28, Volume: 73, Issue:5
Hasubanan alkaloids with delta-opioid binding affinity from the aerial parts of Stephania japonica.
AID480388Displacement of [3H]naloxone from mu opioid receptor expressed in CHO cell membrane at 10 uM2010Journal of natural products, May-28, Volume: 73, Issue:5
Hasubanan alkaloids with delta-opioid binding affinity from the aerial parts of Stephania japonica.
AID408670Selectivity index, ratio of TC50 for primary mice (Mus musculus) hepatocytes to IC50 for Plasmodium yoelii yoelii 265 BY liver stage sporozoites2008Bioorganic & medicinal chemistry, Jun-01, Volume: 16, Issue:11
Isolation and antimalarial activity of new morphinan alkaloids on Plasmodium yoelii liver stage.
AID480387Displacement of [3H]deltorphin-2 from human delta opioid receptor expressed in HEK293 cell membrane2010Journal of natural products, May-28, Volume: 73, Issue:5
Hasubanan alkaloids with delta-opioid binding affinity from the aerial parts of Stephania japonica.
AID408668Antimalarial activity against Plasmodium yoelii 265 sporozoites in primary mice (Mus musculus) hepatocytes after 48 hrs2008Bioorganic & medicinal chemistry, Jun-01, Volume: 16, Issue:11
Isolation and antimalarial activity of new morphinan alkaloids on Plasmodium yoelii liver stage.
AID408669Cytotoxicity against primary mouse hepatocytes after 48 hrs by neutral red assay2008Bioorganic & medicinal chemistry, Jun-01, Volume: 16, Issue:11
Isolation and antimalarial activity of new morphinan alkaloids on Plasmodium yoelii liver stage.
[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's1 (16.67)18.2507
2000's2 (33.33)29.6817
2010's1 (16.67)24.3611
2020's2 (33.33)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%
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]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
primaquine
Primaquine: An aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404). primaquine : An N-substituted diamine that is pentane-1,4-diamine substituted by a 6-methoxyquinolin-8-yl group at the N(4) position. It is a drug used in the treatment of malaria and Pneumocystis pneumonia.		2.0410aminoquinoline;
aromatic ether;
N-substituted diamine		antimalarial
thymidine
[no description available]		1.9910pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
uridine
[no description available]		1.9910uridinesdrug metabolite;
fundamental metabolite;
human metabolite
leucine
Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.		1.9910amino acid zwitterion;
L-alpha-amino acid;
leucine;
proteinogenic amino acid;
pyruvate family amino acid		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
u 69593
U 69593: selective ligand for opioid K-receptor. U69593 : A monocarboxylic acid amide obtained by formal condensation between the carboxy group of phenylacetic acid and the secodary amino group of (5R,7S,8S)-N-methyl-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]decan-8-amine.		2.0510monocarboxylic acid amide;
N-alkylpyrrolidine;
organic heterobicyclic compound;
oxaspiro compound		anti-inflammatory agent;
diuretic;
kappa-opioid receptor agonist
protoberberine
protoberberine: a benzyltetrahydroisoquinoline derivative that appears as an isoquinoline annelated (adjoined) with a naphthylene; the nitrogen is typically quarternary; nitidine is annelated differently; RN given refers to parent cpd		2.0210
enkephalin, ala(2)-mephe(4)-gly(5)-
[no description available]		2.0510peptide
morphinans
Morphinans: Compounds based on a partially saturated iminoethanophenanthrene, which can be described as ethylimino-bridged benzo-decahydronaphthalenes. They include some of the OPIOIDS found in PAPAVER that are used as ANALGESICS.		3.1650isoquinoline alkaloid fundamental parent;
morphinane alkaloid
ConditionIndicatedRelationship StrengthStudiesTrials
Liver Diseases, Parasitic
Liver diseases caused by infections with PARASITES, such as tapeworms (CESTODA) and flukes (TREMATODA).		02.0410
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.610
Viremia
The presence of viruses in the blood.		02.610