Compounds > n-methylactinodaphnine
Page last updated: 2024-12-08

n-methylactinodaphnine

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Description

N-methylactinodaphnine: isolated from Illigera luzonensis; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
Illigeragenus[no description available]HernandiaceaeA plant family of the order Laurales, subclass Magnoliidae, class Magnoliopsida. Members contain cytotoxic furofuran LIGNANS and isoquinoline ALKALOIDS.[MeSH]

Cross-References

ID SourceID
PubMed CID442194
CHEMBL ID464528
CHEBI ID17
MeSH IDM0253044

Synonyms (13)

Synonym
5890-28-8
C09389 ,
(+)-cassythicine
chebi:17 ,
n-methylactinodaphnine
CHEMBL464528 ,
cassythicine
DTXSID20331767
AKOS032948670
Q27105193
(12s)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaen-16-ol
nsc785178
nsc-785178
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
aporphine alkaloidAny benzylisoquinoline alkaloid that has a structure based on 4H-dibenzo[de,g]quinoline or its 3-methyl derivative.
[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]

Bioassays (38)

Assay IDTitleYearJournalArticle
AID376467Cytotoxicity against african green monkey Vero cells1998Journal of natural products, Apr, Volume: 61, Issue:4
Antipoliovirus structure-activity relationships of some aporphine alkaloids.
AID401402Inhibition of arachidonic acid-induced platelet aggregation in rabbit platelet at 100 uM relative to control1998Journal of natural products, Jul, Volume: 61, Issue:7
Chemical constituents from Cassytha filiformis II.
AID398846Antiplatelet activity against arachidonic acid-induced rabbit platelet aggregation assessed as platelet aggregation at 2 ug/ml preincubated for 3 mins by turbidimetric method relative to control1997Journal of natural products, Jun, Volume: 60, Issue:6
Bioactive alkaloids from Illigera luzonensis.
AID403983Antiplatelet activity against collagen-induced rabbit platelet aggregation assessed as platelet aggregation at 100 ug/ml preincubated for 3 mins by turbidimetric method relative to control1997Journal of natural products, Jun, Volume: 60, Issue:6
Bioactive alkaloids from Illigera luzonensis.
AID335143Cytotoxicity against human Col1 cells after 3 days by SRB assay1993Journal of natural products, Sep, Volume: 56, Issue:9
Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.
AID398837Antiplatelet activity against arachidonic acid-induced rabbit platelet aggregation assessed as platelet aggregation at 10 ug/ml preincubated for 3 mins by turbidimetric method relative to control1997Journal of natural products, Jun, Volume: 60, Issue:6
Bioactive alkaloids from Illigera luzonensis.
AID335140Cytotoxicity against human HT1080 cells after 3 days by SRB assay1993Journal of natural products, Sep, Volume: 56, Issue:9
Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.
AID335144Cytotoxicity against human KB cells after 3 days by SRB assay1993Journal of natural products, Sep, Volume: 56, Issue:9
Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.
AID398847Antiplatelet activity against arachidonic acid-induced rabbit platelet aggregation assessed as platelet aggregation at 1 ug/ml preincubated for 3 mins by turbidimetric method relative to control1997Journal of natural products, Jun, Volume: 60, Issue:6
Bioactive alkaloids from Illigera luzonensis.
AID398830Antiplatelet activity against PAF-induced rabbit platelet aggregation assessed as platelet aggregation at 100 ug/ml preincubated for 3 mins by turbidimetric method relative to control1997Journal of natural products, Jun, Volume: 60, Issue:6
Bioactive alkaloids from Illigera luzonensis.
AID335147Cytotoxicity against human A431 cells after 3 days by SRB assay1993Journal of natural products, Sep, Volume: 56, Issue:9
Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.
AID335154Selectivity index, ED50 for human KB cells to ED50 for chloroquine-resistant Plasmodium falciparum W21993Journal of natural products, Sep, Volume: 56, Issue:9
Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.
AID398843Vasorelaxant activity against 3 uM norepinephrine -induced tonic contractions in rat thoracic aorta assessed as muscle contractions at 100 ug/mL pretreated for 15 mins before norepinephrine administration relative to control1997Journal of natural products, Jun, Volume: 60, Issue:6
Bioactive alkaloids from Illigera luzonensis.
AID376475Antiviral activity against Poliovirus 2 Sabin 2 in african green monkey Vero cells assessed as log reduction in virus titers after at 0.001 multiple round of replication at their respective maximum tolerated concentration after 32 hrs1998Journal of natural products, Apr, Volume: 61, Issue:4
Antipoliovirus structure-activity relationships of some aporphine alkaloids.
AID398839Vasorelaxant activity against 80 mM potassium-induced contractions in rat thoracic aorta assessed as muscle contractions at 100 ug/mL pretreated for 15 mins before potassium administration relative to control1997Journal of natural products, Jun, Volume: 60, Issue:6
Bioactive alkaloids from Illigera luzonensis.
AID376471Cytotoxicity against african green monkey Vero cells assessed as drug concentration at which no cellular alteration was microscopically detected1998Journal of natural products, Apr, Volume: 61, Issue:4
Antipoliovirus structure-activity relationships of some aporphine alkaloids.
AID398841Vasorelaxant activity against 3 uM norepinephrine -induced phasic contractions in rat thoracic aorta assessed as muscle contractions at 100 ug/mL pretreated for 15 mins before norepinephrine administration relative to control1997Journal of natural products, Jun, Volume: 60, Issue:6
Bioactive alkaloids from Illigera luzonensis.
AID401413Inhibition of arachidonic acid-induced platelet aggregation in rabbit platelet at 20 uM relative to control1998Journal of natural products, Jul, Volume: 61, Issue:7
Chemical constituents from Cassytha filiformis II.
AID335142Cytotoxicity against human SK-MEL-2 cells after 3 days by SRB assay1993Journal of natural products, Sep, Volume: 56, Issue:9
Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.
AID403982Antiplatelet activity against arachidonic acid-induced rabbit platelet aggregation assessed as platelet aggregation at 100 ug/ml preincubated for 3 mins by turbidimetric method relative to control1997Journal of natural products, Jun, Volume: 60, Issue:6
Bioactive alkaloids from Illigera luzonensis.
AID335139Cytotoxicity against human BCA1 cells after 3 days by SRB assay1993Journal of natural products, Sep, Volume: 56, Issue:9
Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.
AID376473Antiviral activity against Poliovirus 2 Sabin 2 in african green monkey Vero cells assessed as log reduction in virus titers after at 0.01 multiple round of replication at their respective maximum tolerated concentration after 32 hrs1998Journal of natural products, Apr, Volume: 61, Issue:4
Antipoliovirus structure-activity relationships of some aporphine alkaloids.
AID403981Antiplatelet activity against ADP-induced rabbit platelet aggregation assessed as platelet aggregation at 100 ug/ml preincubated for 3 mins by turbidimetric method relative to control1997Journal of natural products, Jun, Volume: 60, Issue:6
Bioactive alkaloids from Illigera luzonensis.
AID335146Cytotoxicity against mouse P388 cells after 3 days by SRB assay1993Journal of natural products, Sep, Volume: 56, Issue:9
Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.
AID335153Selectivity index, ED50 for human KB cells to ED50 for chloroquine-sensitive Plasmodium falciparum D61993Journal of natural products, Sep, Volume: 56, Issue:9
Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.
AID376470Antiviral activity against Poliovirus 2 Sabin 2 in african green monkey Vero cells assessed as log reduction in virus titers after at 0.1 multiple round of replication at their respective maximum tolerated concentration after 32 hrs1998Journal of natural products, Apr, Volume: 61, Issue:4
Antipoliovirus structure-activity relationships of some aporphine alkaloids.
AID401401Inhibition of ADP-induced platelet aggregation in rabbit platelet at 100 uM relative to control1998Journal of natural products, Jul, Volume: 61, Issue:7
Chemical constituents from Cassytha filiformis II.
AID335141Cytotoxicity against human LUC1 cells after 3 days by SRB assay1993Journal of natural products, Sep, Volume: 56, Issue:9
Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.
AID335149Cytotoxicity against human ZR-75-1 cells after 3 days by SRB assay1993Journal of natural products, Sep, Volume: 56, Issue:9
Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.
AID401404Inhibition of PAF-induced platelet aggregation in rabbit platelet at 100 uM relative to control1998Journal of natural products, Jul, Volume: 61, Issue:7
Chemical constituents from Cassytha filiformis II.
AID335150Cytotoxicity against human U373 cells after 3 days by SRB assay1993Journal of natural products, Sep, Volume: 56, Issue:9
Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.
AID335151Antimalarial activity after 24 hrs against chloroquine-sensitive Plasmodium falciparum D6 infected type A+ human erythrocytes by [3H]hypoxanthine uptake1993Journal of natural products, Sep, Volume: 56, Issue:9
Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.
AID335145Cytotoxicity against vinblastine-resistant human KBV1 cells after 3 days by SRB assay1993Journal of natural products, Sep, Volume: 56, Issue:9
Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.
AID398836Antiplatelet activity against arachidonic acid-induced rabbit platelet aggregation assessed as platelet aggregation at 20 ug/ml preincubated for 3 mins by turbidimetric method relative to control1997Journal of natural products, Jun, Volume: 60, Issue:6
Bioactive alkaloids from Illigera luzonensis.
AID398838Antiplatelet activity against arachidonic acid-induced rabbit platelet aggregation assessed as platelet aggregation at 5 ug/ml preincubated for 3 mins by turbidimetric method relative to control1997Journal of natural products, Jun, Volume: 60, Issue:6
Bioactive alkaloids from Illigera luzonensis.
AID335152Antimalarial activity after 24 hrs against chloroquine-resistant Plasmodium falciparum W2 infected type A+ human erythrocytes by [3H]hypoxanthine uptake1993Journal of natural products, Sep, Volume: 56, Issue:9
Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.
AID401403Inhibition of collagen-induced platelet aggregation in rabbit platelet at 100 uM relative to control1998Journal of natural products, Jul, Volume: 61, Issue:7
Chemical constituents from Cassytha filiformis II.
AID335148Cytotoxicity against human LNCAP cells after 3 days by SRB assay1993Journal of natural products, Sep, Volume: 56, Issue:9
Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.
[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's5 (83.33)18.2507
2000's0 (0.00)29.6817
2010's1 (16.67)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: 12.24

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.24 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.18 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.24)

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]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
aspirin
Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.		2.420benzoic acids;
phenyl acetates;
salicylates		anticoagulant;
antipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
drug allergen;
EC 1.1.1.188 (prostaglandin-F synthase) inhibitor;
geroprotector;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
plant activator;
platelet aggregation inhibitor;
prostaglandin antagonist;
teratogenic agent
chloroquine
Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.		1.9810aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug
mefloquine hydrochloride
[2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanol : An organofluorine compound that consists of quinoline bearing trifluoromethyl substituents at positions 2 and 8 as well as a (2-piperidinyl)hydroxymethyl substituent at position 4.		1.9810organofluorine compound;
piperidines;
quinolines;
secondary alcohol
nifedipine
Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.		1.9910C-nitro compound;
dihydropyridine;
methyl ester		calcium channel blocker;
human metabolite;
tocolytic agent;
vasodilator agent
prazosin
Prazosin: A selective adrenergic alpha-1 antagonist used in the treatment of HEART FAILURE; HYPERTENSION; PHEOCHROMOCYTOMA; RAYNAUD DISEASE; PROSTATIC HYPERTROPHY; and URINARY RETENTION.. prazosin : A member of the class of piperazines that is piperazine substituted by a furan-2-ylcarbonyl group and a 4-amino-6,7-dimethoxyquinazolin-2-yl group at positions 1 and 4 respectively.		2.3920aromatic ether;
furans;
monocarboxylic acid amide;
piperazines;
quinazolines		alpha-adrenergic antagonist;
antihypertensive agent;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
5-methylurapidil
[no description available]		1.9810
liriodenine
liriodenine: structure given in first source. liriodenine : An oxoaporphine alkaloid that is 4,5,6,6a-tetradehydronoraporphin-7-one substituted by a methylenedioxy group across positions 1 and 2. It is isolated from Annona glabra and has been shown to exhibit antimicrobial and cytotoxic activities.		2.420alkaloid antibiotic;
cyclic ketone;
organic heteropentacyclic compound;
oxacycle;
oxoaporphine alkaloid		antifungal agent;
antimicrobial agent;
antineoplastic agent;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
metabolite
corydine
corydine: structure given in first source; RN given refers to (S)-isomer		1.9810
boldine
[no description available]		1.9910aporphine alkaloid
bicuculline
Bicuculline: An isoquinoline alkaloid obtained from Dicentra cucullaria and other plants. It is a competitive antagonist for GABA-A receptors.. bicuculline : A benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline which is substituted at the 5-pro-S position by a (6R)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species.		2.0510benzylisoquinoline alkaloid;
isoquinoline alkaloid;
isoquinolines		agrochemical;
central nervous system stimulant;
GABA-gated chloride channel antagonist;
GABAA receptor antagonist;
neurotoxin
bulbocapnine
bulbocapnine: was heading 1975-94 (Prov 1975-90); use APORPHINES to search BULBOCAPNINE 1975-94 (as Prov 1975-94); alkaloid from Corydalis cava and other plants; induces catalepsy probably due to its antagonism of DOPAMINE. bulbocapnine : An aporphine alkaloid that has been isolated from Corydalis and exhibits inhibitory activity against enzymes such as tyrosine 3-monooxygenase and diamine oxidase.		1.9910aporphine alkaloid;
aromatic ether;
oxacycle;
phenols		EC 1.14.16.2 (tyrosine 3-monooxygenase) inhibitor;
EC 1.4.3.22 (diamine oxidase) inhibitor;
plant metabolite
n-methyllaurotetanine
N-methyllaurotetanine: structure in first source		1.9910
laurolitsine
laurolitsine: RN given for (S)-isomer; structure in first source. laurolistine : An aporphine alkaloid that is noraporphine substituted by hydroxy groups at positions 2 and 9 and methoxy groups at positions 1 and 10. Isolated from Litsea glutinosa and Lindera chunii, exhibits inhibitory activity against HIV-1 integrase.		1.9910aporphine alkaloid;
aromatic ether;
phenols		HIV-1 integrase inhibitor;
metabolite
laurotetanine
laurotetanine: isolated from Tetranthera & Lindera benzoin L. from family Lauraceae; structure		1.9910isoquinoline alkaloid
tetrahydropalmatine
[no description available]		1.9810an (S)-7,8,13,14-tetrahydroprotoberberine;
berberine alkaloid;
organic heterotetracyclic compound		adrenergic agent;
dopaminergic antagonist;
non-narcotic analgesic
magnoflorine
magnoflorine: opium alkaloid having the aporphine configuration; RN given refers to parent cpd(S)-isomer; structure. (S)-magnoflorine : An aporphine alkaloid that is (S)-corytuberine in which the nitrogen has been quaternised by an additional methyl group.		1.9810aporphine alkaloid;
quaternary ammonium ion		plant metabolite
dicentrine
dicentrine: structure given in first source; RN refers to (S)-isomer		1.9910aporphine alkaloid
lysicamine
lysicamine: oxoaporphine alkaloid; structure in first source		1.9910alkaloid antibiotic;
oxoaporphine alkaloid		metabolite
actinodaphine
actinodaphine: structure given in first source; isolated from Illigera SP. actinodaphnine : An organic heteropentacyclic compound 6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinoline bering additional hydroxy and methoxy substituents at positions 10 and 11 respectively.		2.6930aporphine alkaloid;
aromatic ether;
organic heteropentacyclic compound;
phenols;
secondary amino compound		antibacterial agent;
antifungal agent;
antineoplastic agent;
apoptosis inducer;
plant metabolite;
platelet aggregation inhibitor;
topoisomerase inhibitor
xylopine
xylopine: RN given refers to (R)-isomer; RN for cpd without isomeric designation not available 3/90; structure given in first source		1.9810aporphine alkaloid
anonaine
anonaine: smooth muscle relaxant; aporphine alkaloid isolated from roots of Annona cherimolia; structure in first source. (-)-annonaine : An aporphine alkaloid that exhibits anti-cancer, trypanocidal and antiplasmodial activites.		1.9810aporphine alkaloid;
organic heteropentacyclic compound;
oxacycle		antineoplastic agent;
antiplasmodial drug;
trypanocidal drug
asimilobine
asimilobine: from Nelumbro nucifera; RN given refers to (R)-isomer		1.9810aporphine alkaloidmetabolite
corydalmine
corydalmine: antagonizes dopamine receptors; structure given in first source; RN given refers to (S)-isomer		1.9810
dicentrinone
dicentrinone: from Ocotea leucoxylon; structure in first source		1.9910
norcoralydine
norcoralydine: neuromuscular blocking agent; RN given refers to (S)-isomer; structure		1.9810alkaloid
dicentrine
[no description available]		1.9810
reticuline
reticuline: opium alkaloid; dopamine receptor blocker; RN given refers to (S)-isomer; structure. (S)-reticuline : The (S)-enantiomer of reticuline.		1.9810reticulineEC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor
quinine
[no description available]		1.9810cinchona alkaloidantimalarial;
muscle relaxant;
non-narcotic analgesic
ConditionIndicatedRelationship StrengthStudiesTrials
Muscle Contraction
A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.		02.3920