Compounds > 3',4'-didemethylnobiletin
Page last updated: 2024-08-01 15:52:16

3',4'-didemethylnobiletin

Description

3',4'-didemethylnobiletin: a urinary metabolite derived from nobiletin; has anti-inflammatory and antitumor activities; structure in first source [MeSH]

Cross-References

ID SourceID
PubMed CID5318041
CHEMBL ID438292
SCHEMBL ID1764426
MeSH IDM0528914

Synonyms (12)

Synonym
3',4'-didemethylnobiletin
sideritiflavone 5-methyl ether
CHEMBL438292 ,
2-(3,4-dihydroxyphenyl)-5,6,7,8-tetramethoxychromen-4-one
80140-31-4
bdbm50412303
3',4'-dihydroxy-5,6,7,8-tetramethoxyflavone
ZDLYNMZEAFURQY-UHFFFAOYSA-N
SCHEMBL1764426
DTXSID60415732
3',4'-dihydroxy-5,6,7,8-tetramethoxy flavone
2-(3,4-dihydroxyphenyl)-5,6,7,8-tetramethoxy-4h-chromen-4-one

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Aldo-keto reductase family 1 member B1Rattus norvegicus (Norway rat)IC500.0324AID342547

Bioassays (20)

Assay IDTitleYearJournalArticle
AID288087Apoptotic activity in HL60 cells after 24 hrs2007Bioorganic & medicinal chemistry, May-15, Volume: 15, Issue:10
ISSN: 0968-0896		Isolation and syntheses of polymethoxyflavones and hydroxylated polymethoxyflavones as inhibitors of HL-60 cell lines.
AID309062Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide production at 30 uM after 24 hrs2007Bioorganic & medicinal chemistry letters, Sep-15, Volume: 17, Issue:18
ISSN: 0960-894X		Anti-inflammatory property of the urinary metabolites of nobiletin in mouse.
AID288086Antiproliferative activity against HL60 after 24 hrs2007Bioorganic & medicinal chemistry, May-15, Volume: 15, Issue:10
ISSN: 0968-0896		Isolation and syntheses of polymethoxyflavones and hydroxylated polymethoxyflavones as inhibitors of HL-60 cell lines.
AID724431Growth inhibition of human SRA 01/04 cells at 32 uM after 4 days by Alamar blue assay2013Bioorganic & medicinal chemistry letters, Jan-01, Volume: 23, Issue:1
ISSN: 1464-3405		Polymethoxyflavones as agents that prevent formation of cataract: nobiletin congeners show potent growth inhibitory effects in human lens epithelial cells.
AID309064Inhibition of LPS-induced iNOS protein expression in mouse RAW264.7 cells at 5 uM after 24 hrs by Western blotting2007Bioorganic & medicinal chemistry letters, Sep-15, Volume: 17, Issue:18
ISSN: 0960-894X		Anti-inflammatory property of the urinary metabolites of nobiletin in mouse.
AID342547Inhibition of rat lens aldose reductase2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
ISSN: 1464-3391		QSAR prediction of inhibition of aldose reductase for flavonoids.
AID356483Cytotoxicity against rat RBL2H3 cells at 500 uM by optical microscope2003Journal of natural products, Sep, Volume: 66, Issue:9
ISSN: 0163-3864		Tricin from a malagasy connaraceous plant with potent antihistaminic activity.
AID356482Antihistaminic activity in rat RBL2H3 cells assessed as inhibition of DNP-BSA-induced beta-hexosaminidase release preincubated for 10 mins before DNP-BSA challenge2003Journal of natural products, Sep, Volume: 66, Issue:9
ISSN: 0163-3864		Tricin from a malagasy connaraceous plant with potent antihistaminic activity.
AID309068Inhibition of LPS-induced iNOS gene expression in mouse RAW264.7 cells at 20 uM after 24 hrs by RT-PCR2007Bioorganic & medicinal chemistry letters, Sep-15, Volume: 17, Issue:18
ISSN: 0960-894X		Anti-inflammatory property of the urinary metabolites of nobiletin in mouse.
AID309063Cytotoxicity against mouse RAW264.7 cells at 30 uM by MTT assay2007Bioorganic & medicinal chemistry letters, Sep-15, Volume: 17, Issue:18
ISSN: 0960-894X		Anti-inflammatory property of the urinary metabolites of nobiletin in mouse.
AID635945Inhibition of TNFalpha-stimulated pro MMP9 production in human SRA 01/04 cells after 24 hrs by SDS-PAGE based gelatin zymography assay2011Bioorganic & medicinal chemistry, Dec-01, Volume: 19, Issue:23
ISSN: 1464-3391		B-Ring-modified and/or 5-demethylated nobiletin congeners: inhibitory activity against pro-MMP-9 production.
AID309066Inhibition of LPS-induced COX2 protein expression in mouse RAW264.7 cells at 5 uM after 24 hrs by Western blotting2007Bioorganic & medicinal chemistry letters, Sep-15, Volume: 17, Issue:18
ISSN: 0960-894X		Anti-inflammatory property of the urinary metabolites of nobiletin in mouse.
AID309065Inhibition of LPS-induced iNOS protein expression in mouse RAW264.7 cells at 20 uM after 24 hrs by Western blotting2007Bioorganic & medicinal chemistry letters, Sep-15, Volume: 17, Issue:18
ISSN: 0960-894X		Anti-inflammatory property of the urinary metabolites of nobiletin in mouse.
AID635947Inhibition of PMA-stimulated pro MMP9 production in human SRA 01/04 cells after 24 hrs by SDS-PAGE based gelatin zymography assay2011Bioorganic & medicinal chemistry, Dec-01, Volume: 19, Issue:23
ISSN: 1464-3391		B-Ring-modified and/or 5-demethylated nobiletin congeners: inhibitory activity against pro-MMP-9 production.
AID609402Inhibition of PMA-induced proMMP9 production in human SRA 01/04 cells after 24 hrs by SDS-PAGE analysis2011Bioorganic & medicinal chemistry letters, Aug-01, Volume: 21, Issue:15
ISSN: 1464-3405		Nobiletin metabolites: synthesis and inhibitory activity against matrix metalloproteinase-9 production.
AID309061Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide production at 10 uM after 24 hrs2007Bioorganic & medicinal chemistry letters, Sep-15, Volume: 17, Issue:18
ISSN: 0960-894X		Anti-inflammatory property of the urinary metabolites of nobiletin in mouse.
AID609403Inhibition of TNF-alpha-induced proMMP9 production in human SRA 01/04 cells after 24 hrs by SDS-PAGE analysis2011Bioorganic & medicinal chemistry letters, Aug-01, Volume: 21, Issue:15
ISSN: 1464-3405		Nobiletin metabolites: synthesis and inhibitory activity against matrix metalloproteinase-9 production.
AID309067Inhibition of LPS-induced COX2 protein expression in mouse RAW264.7 cells at 20 uM after 24 hrs by Western blotting2007Bioorganic & medicinal chemistry letters, Sep-15, Volume: 17, Issue:18
ISSN: 0960-894X		Anti-inflammatory property of the urinary metabolites of nobiletin in mouse.
AID309069Inhibition of LPS-induced COX2 gene expression in mouse RAW264.7 cells at 20 uM after 24 hrs by RT-PCR2007Bioorganic & medicinal chemistry letters, Sep-15, Volume: 17, Issue:18
ISSN: 0960-894X		Anti-inflammatory property of the urinary metabolites of nobiletin in mouse.
AID288088Cytotoxicity against human PMN cells at 100 uM2007Bioorganic & medicinal chemistry, May-15, Volume: 15, Issue:10
ISSN: 0968-0896		Isolation and syntheses of polymethoxyflavones and hydroxylated polymethoxyflavones as inhibitors of HL-60 cell lines.

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (41.67)29.6817
2010's6 (50.00)24.3611
2020's1 (8.33)2.80

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%
Other12 (100.00%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
cromolyn sodium
1
organic sodium saltanti-asthmatic drug;
drug allergen		2003200321.0low000100
pedalitin
1
monomethoxyflavone;
tetrahydroxyflavone		EC 1.17.3.2 (xanthine oxidase) inhibitor;
metabolite		2008200816.0low000100
tangeretin
4
pentamethoxyflavoneantineoplastic agent;
plant metabolite		2003201315.5low000220
nobiletin
5
methoxyflavoneantineoplastic agent;
plant metabolite		2007201314.2low000230
xanthomicrol
3
dihydroxyflavone;
trimethoxyflavone		antineoplastic agent;
plant metabolite		2008201313.3medium000120
gardenin b
1
monohydroxyflavone;
tetramethoxyflavone		plant metabolite2007200717.0low000100
5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone
1
ether;
flavonoids		2007200717.0low000100
sinensetin
1
pentamethoxyflavoneplant metabolite2007200717.0low000100
3,3',4',5,6,7,8-heptamethoxyflavone
1
ether;
flavonoids		2007200717.0low000100
5-hydroxy-3',4',6,7-tetramethoxyflavone
1
2007200717.0low000100
sideritoflavone
2
ether;
flavonoids		2003200818.5high000200
cirsiliol
1
dimethoxyflavone;
trihydroxyflavone		plant metabolite2008200816.0low000100
nevadensin
1
dihydroxyflavone;
trimethoxyflavone		plant metabolite2008200816.0low000100
cirsilineol
1
dihydroxyflavone;
trimethoxyflavone		antineoplastic agent;
plant metabolite		2008200816.0low000100
4',5-dihydroxy-3',6,7,8-tetramethoxyflavone
3
2008201313.3high000120
4',6-dihydroxyflavone
1
dihydroxyflavone2008200816.0medium000100
3'-demethylnobiletin
4
ether;
flavonoids		2007201115.0high000220
cirsimaritin
2
dihydroxyflavone;
dimethoxyflavone		2003200818.5low000200
gardenin a
1
2007200717.0low000100
5-demethylnobiletin
3
ether;
flavonoids		2007201313.7medium000120
3',4'-dimethoxyflavone
1
2003200321.0low000100
demethoxysudachitin
1
ether;
flavonoids		2008200816.0medium000100
natsudaidain
1
hydroxyflavan2007200717.0medium000100
apigenin
1
trihydroxyflavoneantineoplastic agent;
metabolite		2003200321.0low000100
luteolin
1
3'-hydroxyflavonoid;
tetrahydroxyflavone		angiogenesis inhibitor;
anti-inflammatory agent;
antineoplastic agent;
apoptosis inducer;
c-Jun N-terminal kinase inhibitor;
EC 2.3.1.85 (fatty acid synthase) inhibitor;
immunomodulator;
nephroprotective agent;
plant metabolite;
radical scavenger;
vascular endothelial growth factor receptor antagonist		2003200321.0low000100
dexmedetomidine
1
trihydroxyflavone;
trimethoxyflavone		antineoplastic agent;
metabolite		2008200816.0low000100
axillarin
1
dimethoxyflavone;
tetrahydroxyflavone		plant metabolite2008200816.0medium000100
baicalein
1
trihydroxyflavoneangiogenesis inhibitor;
anti-inflammatory agent;
antibacterial agent;
anticoronaviral agent;
antifungal agent;
antineoplastic agent;
antioxidant;
apoptosis inducer;
EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor;
EC 4.1.1.17 (ornithine decarboxylase) inhibitor;
ferroptosis inhibitor;
geroprotector;
hormone antagonist;
plant metabolite;
prostaglandin antagonist;
radical scavenger		2003200321.0low000100
chrysin
1
7-hydroxyflavonol;
dihydroxyflavone		anti-inflammatory agent;
antineoplastic agent;
antioxidant;
EC 2.7.11.18 (myosin-light-chain kinase) inhibitor;
hepatoprotective agent;
plant metabolite		2003200321.0low000100
6-hydroxyluteolin
1
pentahydroxyflavone2008200816.0medium000100
scutellarein
1
tetrahydroxyflavonemetabolite2003200321.0low000100
tricin
1
3'-methoxyflavones;
dimethoxyflavone;
trihydroxyflavone		EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
metabolite		2003200321.0low000100
artemetin
1
ether;
flavonoids		2007200717.0low000100
3',4',5'-O-trimethyltricetin
1
3',5'-dimethoxyflavone;
dihydroxyflavone;
trimethoxyflavone		2003200321.0medium000100
sudachitin
1
ether;
flavonoids		2008200816.0low000100
4'-hydroxy-5,6,7,8,3'-pentamethoxyflavone
6
ether;
flavonoids		2007201314.5high000330
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
7,12-dihydroxymethylbenz(a)anthracene
1
2008200816.0low000100
tetradecanoylphorbol acetate
1
acetate ester;
diester;
phorbol ester;
tertiary alpha-hydroxy ketone;
tetradecanoate ester		antineoplastic agent;
apoptosis inducer;
carcinogenic agent;
mitogen;
plant metabolite;
protein kinase C agonist;
reactive oxygen species generator		2010201014.0low000100
nobiletin
5
methoxyflavoneantineoplastic agent;
plant metabolite		2008202011.0low000230
3'-demethylnobiletin
1
ether;
flavonoids		201520159.0medium000010
curcumin
1
aromatic ether;
beta-diketone;
diarylheptanoid;
enone;
polyphenol		anti-inflammatory agent;
antifungal agent;
antineoplastic agent;
biological pigment;
contraceptive drug;
dye;
EC 1.1.1.205 (IMP dehydrogenase) inhibitor;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor;
EC 1.8.1.9 (thioredoxin reductase) inhibitor;
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor;
EC 3.5.1.98 (histone deacetylase) inhibitor;
flavouring agent;
food colouring;
geroprotector;
hepatoprotective agent;
immunomodulator;
iron chelator;
ligand;
lipoxygenase inhibitor;
metabolite;
neuroprotective agent;
nutraceutical;
radical scavenger		202020204.0low000010
4'-hydroxy-5,6,7,8,3'-pentamethoxyflavone
1
ether;
flavonoids		201520159.0low000010
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Cancer of Colon0
2
201520206.5medium000020
Cancer of Skin0
1
2008200816.0low000100
Cataract0
1
2013201311.0low000010
Cataract, Membranous0
1
2013201311.0low000010
Colitis0
1
201520159.0low000010
Colonic Neoplasms0
2
201520206.5medium000020
Experimental Neoplasms0
1
201520159.0low000010
Leucocythaemia0
1
2003200321.0low000100
Leukemia0
1
2003200321.0low000100
Skin Neoplasms0
1
2008200816.0low000100