Compounds > Methyl nigakinone
Page last updated: 2024-12-09

Methyl nigakinone

Description

4,5-dimethoxycanthin-6-one: an active metabolite of Picrasma quassiodes; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID638215
CHEMBL ID2386324
CHEBI ID80849

Synonyms (20)

Synonym
6h-indolo(3,2,1-de)(1,5)naphthyridin-6-one, 4,5-dimethoxy-
methyl nigakinone
6h-indolo[3,2,1-de][1,5]naphthyridin-6-one, 4,5-dimethoxy-
inchi=1/c16h12n2o3/c1-20-14-12-13-10(7-8-17-12)9-5-3-4-6-11(9)18(13)16(19)15(14)21-2/h3-8h,1-2h
C16996
18110-87-7
4,5-dimethoxycanthin-6-one
chebi:80849 ,
CHEMBL2386324
DTXSID90171076
AKOS032948585
3,4-dimethoxy-1,6-diazatetracyclo[7.6.1.0^{5,16.0^{10,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one
Q27151344
3,4-dimethoxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one
MS-23973
B0005-171424
E80581
CS-0017767
HY-N1882
PD196219
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
beta-carbolinesAny pyridoindole containing a beta-carboline skeleton and their hydrogenated derivatives
[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 (18)

Assay IDTitleYearJournalArticle
AID751085Antiviral activity against Coxsackievirus B3 infected in african green monkey Vero cells assessed as inhibition of virus-induced cytopathic effect2013Journal of natural products, Jun-28, Volume: 76, Issue:6
Sesquiterpenes and alkaloids from the roots of Alangium chinense.
AID751079Cytotoxicity against human A2780 cells by MTT assay2013Journal of natural products, Jun-28, Volume: 76, Issue:6
Sesquiterpenes and alkaloids from the roots of Alangium chinense.
AID751080Cytotoxicity against human Bel7402 cells by MTT assay2013Journal of natural products, Jun-28, Volume: 76, Issue:6
Sesquiterpenes and alkaloids from the roots of Alangium chinense.
AID1080741Antiviral activity against Tobacco mosaic virus U1 (TMV) infected Nicotiana glutinosa leaves assessed as inhibition of viral replication at 50 ug/mL in presence of 25 ug/mL quassinoid nigakilactone B measured 48 hr after compound exposure by half leaf met2009Journal of agricultural and food chemistry, Aug-12, Volume: 57, Issue:15
Tobacco mosaic virus (TMV) inhibitors from Picrasma quassioides Benn.
AID751081Cytotoxicity against human BGC823 cells by MTT assay2013Journal of natural products, Jun-28, Volume: 76, Issue:6
Sesquiterpenes and alkaloids from the roots of Alangium chinense.
AID751078Cytotoxicity against human HCT8 cells by MTT assay2013Journal of natural products, Jun-28, Volume: 76, Issue:6
Sesquiterpenes and alkaloids from the roots of Alangium chinense.
AID1320173Cerebral protective activity in cerebral ischemia-induced Mongolian gerbil assessed as passive avoidance test value at 100 mg/kg, po pretreated for 30 mins followed by bilateral ligation-induced ischemia for 5 mins measured on day 1 post 3 days ischemia i2016Bioorganic & medicinal chemistry letters, 10-15, Volume: 26, Issue:20
Evaluation of canthinone alkaloids as cerebral protective agents.
AID751082Cytotoxicity against human A549 cells by MTT assay2013Journal of natural products, Jun-28, Volume: 76, Issue:6
Sesquiterpenes and alkaloids from the roots of Alangium chinense.
AID1320174Cerebral protective activity in anesthetized cerebral ischemia-induced Mongolian gerbil hippocampus assessed as protective values on density of surviving neurons in CA1 subfields of hippocampus at 100 mg/kg, po pretreated for 30 mins followed by bilateral2016Bioorganic & medicinal chemistry letters, 10-15, Volume: 26, Issue:20
Evaluation of canthinone alkaloids as cerebral protective agents.
AID1080735Antiviral activity against Tobacco mosaic virus U1 (TMV) infected Nicotiana tabacum cv. K326 leaves assessed as inhibition of viral replication in presence of 25 ug/mL quassinoid nigakilactone B measured 48 hr after compound exposure by leaf-disk method2009Journal of agricultural and food chemistry, Aug-12, Volume: 57, Issue:15
Tobacco mosaic virus (TMV) inhibitors from Picrasma quassioides Benn.
AID751084Antioxidant activity in rat liver microsome assessed as inhibition of Fe2+-cysteine-induced lipid peroxidation after 15 mins2013Journal of natural products, Jun-28, Volume: 76, Issue:6
Sesquiterpenes and alkaloids from the roots of Alangium chinense.
AID1194597Inhibition of PTP1B (unknown origin) assessed as inhibition rate at 100 uM2015Bioorganic & medicinal chemistry letters, May-01, Volume: 25, Issue:9
Canthinone alkaloids are novel protein tyrosine phosphatase 1B inhibitors.
AID1080739Antiviral activity against Tobacco mosaic virus U1 (TMV) infected Nicotiana tabacum cv. K326 leaves assessed as inhibition of viral replication at 50 ug/mL in presence of 25 ug/mL quassinoid nigakilactone B measured 48 hr after compound exposure by leaf-d2009Journal of agricultural and food chemistry, Aug-12, Volume: 57, Issue:15
Tobacco mosaic virus (TMV) inhibitors from Picrasma quassioides Benn.
AID1080738Antiviral activity against Tobacco mosaic virus U1 (TMV) infected Nicotiana glutinosa leaves assessed as inhibition of viral infection at 50 ug/mL using compound pre-treated virus suspension in presence of 25 ug/mL quassinoid nigakilactone B measured 5 to2009Journal of agricultural and food chemistry, Aug-12, Volume: 57, Issue:15
Tobacco mosaic virus (TMV) inhibitors from Picrasma quassioides Benn.
AID1080740Antiviral activity against Tobacco mosaic virus U1 (TMV) infected Nicotiana tabacum cv. K326 leaves assessed as inhibition of viral replication at 50 ug/mL measured 48 hr after compound exposure by leaf-disk method2009Journal of agricultural and food chemistry, Aug-12, Volume: 57, Issue:15
Tobacco mosaic virus (TMV) inhibitors from Picrasma quassioides Benn.
AID1080736Antiviral activity against Tobacco mosaic virus U1 (TMV) infected Nicotiana tabacum cv. K326 leaves assessed as inhibition of viral replication measured 48 hr after compound exposure by leaf-disk method2009Journal of agricultural and food chemistry, Aug-12, Volume: 57, Issue:15
Tobacco mosaic virus (TMV) inhibitors from Picrasma quassioides Benn.
AID1080737Antiviral activity against Tobacco mosaic virus U1 (TMV) infected Nicotiana glutinosa leaves assessed as inhibition of viral infection at 50 ug/mL using compound pre-treated virus suspension measured 5 to 6 days after compound exposure2009Journal of agricultural and food chemistry, Aug-12, Volume: 57, Issue:15
Tobacco mosaic virus (TMV) inhibitors from Picrasma quassioides Benn.
AID1080742Antiviral activity against Tobacco mosaic virus U1 (TMV) infected Nicotiana glutinosa leaves assessed as inhibition of viral replication at 50 ug/mL measured 48 hr after compound exposure by half leaf method2009Journal of agricultural and food chemistry, Aug-12, Volume: 57, Issue:15
Tobacco mosaic virus (TMV) inhibitors from Picrasma quassioides Benn.
[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's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's4 (80.00)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: 13.28

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 Index13.28 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index5.08 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.28)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
d-alpha tocopherol
Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.		2.0810alpha-tocopherolalgal metabolite;
antiatherogenic agent;
anticoagulant;
antioxidant;
antiviral agent;
EC 2.7.11.13 (protein kinase C) inhibitor;
immunomodulator;
micronutrient;
nutraceutical;
plant metabolite
mansonone c
mansonone C: structure in first source		2.08101,2-naphthoquinones;
sesquiterpenoid
ribavirin
Rebetron: Rebetron is tradename		2.08101-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide		anticoronaviral agent;
antiinfective agent;
antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid
1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid: precursor of mutagenic nitroso cpd in soy sauce; structure given in first source		2.1110harmala alkaloid
mansonone e
mansonone E: a potent anti-bacterial sesquiterpenoid isolated from the dried root bark of Ulmus pumila; structure in first source		2.0810
canthin-6-one
canthin-6-one: from Zanthoxylum usambarense; structure in first source. canthin-6-one : An indole alkaloid that is 6H-indolo[3,2,1-de][1,5]naphthyridine substituted by an oxo group at position 6.		2.1110enone;
indole alkaloid;
organic heterotetracyclic compound		antimycobacterial drug;
metabolite
1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid
1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid: structure given in first source; RN given refers to cpd without isomeric designation. 1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid : A member of the class of beta-carbolines that is 1,2,3,4-tetrahydro-beta-carboline substituted at position 3 by a carboxy group.		2.1110alpha-amino acid;
aromatic amino acid;
beta-carboline alkaloid		human urinary metabolite;
human xenobiotic metabolite;
plant metabolite;
rat metabolite
vinpocetine
[no description available]		2.1310
beta-carboline-3-carboxylic acid methyl ester
beta-carboline-3-carboxylic acid methyl ester: structure given in first source		2.1110beta-carbolines
5-methoxycanthin-6-one
5-methoxycanthin-6-one: isolated from Zanthoxylum chiloperone; structure in first source		2.4820alkaloid;
organic heterotetracyclic compound
Amalorin
[no description available]		2.1110alkaloid;
organic heterotetracyclic compound
7-hydroxycadalin
7-hydroxycadalin: isolated from Heterotheca inuloides; structure in first source		2.0810sesquiterpenoid
1-acetyl-beta-carboline
1-acetyl-beta-carboline: structure in first source		2.1110harmala alkaloidmetabolite
harman
harman: a beta-carboline; RN given refers to parent cpd; structure. harman : An indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, Passiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A.		2.1110harmala alkaloid;
indole alkaloid fundamental parent;
indole alkaloid		anti-HIV agent;
EC 1.4.3.4 (monoamine oxidase) inhibitor;
plant metabolite
dehydrocrenatidine
dehydrocrenatidine: a janus kinase inhibitor; structure in first source		2.1110
nigakinone
nigakinone: an NSAID that may be useful in treating ulcerative colitis; structure in first source		2.5220beta-carbolines
1-Ethyl-9H-pyrido[3,4-b]indole
[no description available]		2.1110harmala alkaloid
beta-carboline-1-propionic acid
[no description available]		2.1110harmala alkaloid
1-methyl-beta-carboline-3-carboxylic acid
1-methyl-beta-carboline-3-carboxylic acid: metabolite from cows fed with corn silage; structure in first source		2.1110
9-methoxycanthin-6-one
9-methoxycanthin-6-one: from roots of Eurycoma longifolia (Simaroubaceae). 9-methoxycanthin-6-one : An indole alkaloid that is the 9-methoxy derivative of canthin-6-one. Isolated from Eurycoma longifolia and Simaba multiflora, it exhibits cytotoxic activity towards human cancer cell lines.		2.1110aromatic ether;
indole alkaloid;
organic heterotetracyclic compound		antineoplastic agent;
antiplasmodial drug;
metabolite
ningnanmycin
ningnanmycin: isolated from Strepcomces noursei		2.0510
rk 682
[no description available]		2.1110
ConditionIndicatedRelationship StrengthStudiesTrials
Cerebral Ischemia
[description not available]		02.1310
Brain Ischemia
Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.		02.1310
chemdatabank.com