CHEBI:15864 - luteolin

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ChEBI Name luteolin
ChEBI ID CHEBI:15864
Definition A tetrahydroxyflavone in which the four hydroxy groups are located at positions 3', 4' 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an inflammatory agent and an immune system modulator as well as being active against several cancers.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:12082, CHEBI:14536, CHEBI:6578, CHEBI:25086
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Formula C15H10O6
Net Charge 0
Average Mass 286.23630
Monoisotopic Mass 286.048
InChI InChI=1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H
InChIKey IQPNAANSBPBGFQ-UHFFFAOYSA-N
SMILES Oc1cc(O)c2c(c1)oc(cc2=O)-c1ccc(O)c(O)c1
Metabolite of Species Details
Olea europaea (NCBI:4146) Found in leaf (BTO:0000713). Methanolic extract of dried olive leaves See: PubMed
Mimosa diplotricha (NCBI:512270) Found in aerial part (BTO:0001658). Ethanolic extract of aerial part See: PubMed
Cirsium japonicum (NCBI:516546) Found in whole plant (BTO:0001461). Hot methanolic extract of dried whole plant See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): vascular endothelial growth factor receptor antagonist
An antagonist at the vascular endothelial growth factor receptor.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
c-Jun N-terminal kinase inhibitor
A EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor that inhibits the action of c-Jun N-terminal kinase
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
EC 2.3.1.85 (fatty acid synthase) inhibitor
An EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor that interferes with the action of fatty acid synthase (EC 2.3.1.85), a multi-enzyme protein involved in fatty acid synthesis.
Application(s): nephroprotective agent
Any protective agent that is able to prevent damage to the kidney.
angiogenesis inhibitor
An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing luteolin (CHEBI:15864) has role angiogenesis inhibitor (CHEBI:48422)
luteolin (CHEBI:15864) has role anti-inflammatory agent (CHEBI:67079)
luteolin (CHEBI:15864) has role antineoplastic agent (CHEBI:35610)
luteolin (CHEBI:15864) has role antioxidant (CHEBI:22586)
luteolin (CHEBI:15864) has role apoptosis inducer (CHEBI:68495)
luteolin (CHEBI:15864) has role c-Jun N-terminal kinase inhibitor (CHEBI:90172)
luteolin (CHEBI:15864) has role EC 2.3.1.85 (fatty acid synthase) inhibitor (CHEBI:71476)
luteolin (CHEBI:15864) has role nephroprotective agent (CHEBI:76595)
luteolin (CHEBI:15864) has role plant metabolite (CHEBI:76924)
luteolin (CHEBI:15864) has role vascular endothelial growth factor receptor antagonist (CHEBI:65207)
luteolin (CHEBI:15864) is a 3'-hydroxyflavonoid (CHEBI:27741)
luteolin (CHEBI:15864) is a tetrahydroxyflavone (CHEBI:38684)
luteolin (CHEBI:15864) is conjugate acid of 2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-olate luteolin-7-olate(1−) (CHEBI:57545)
Incoming 4',5,7-trihydroxy-3'-methoxyflavone (CHEBI:16514) has functional parent luteolin (CHEBI:15864)
5,3'-di-O-methylluteolin (CHEBI:69455) has functional parent luteolin (CHEBI:15864)
6-C-α-L-arabinopyranosyl-8-C-β-D-glucosylluteolin (CHEBI:75566) has functional parent luteolin (CHEBI:15864)
6-C-[2'-O-α-L-rhamnopyranosyl-(1''→2')]-α-L-arabinopyranosylluteolin (CHEBI:70201) has functional parent luteolin (CHEBI:15864)
6-C-[2-O-α-L-rhamnopyranosyl-(1''→2')]-β-D-xylopyranosylluteolin (CHEBI:70202) has functional parent luteolin (CHEBI:15864)
6-hydroxyluteolin (CHEBI:2197) has functional parent luteolin (CHEBI:15864)
6-hydroxyluteolin 7-O-laminaribioside (CHEBI:66046) has functional parent luteolin (CHEBI:15864)
6-methoxyluteolin 7-α-L-rhamnoside (CHEBI:28314) has functional parent luteolin (CHEBI:15864)
7-O-[β-D-arabinopyranosyl-(1→6)-β-D-glucosyl]luteolin (CHEBI:75532) has functional parent luteolin (CHEBI:15864)
carlinoside (CHEBI:3421) has functional parent luteolin (CHEBI:15864)
cassiaoccidentalin B (CHEBI:70205) has functional parent luteolin (CHEBI:15864)
diosmetin (CHEBI:4630) has functional parent luteolin (CHEBI:15864)
hypolaetin (CHEBI:5837) has functional parent luteolin (CHEBI:15864)
isoorientin (CHEBI:17965) has functional parent luteolin (CHEBI:15864)
lucenin-2 (CHEBI:6553) has functional parent luteolin (CHEBI:15864)
luteolin 6-C-[β-D-glucosyl-(1→2)-α-L-arabinoside] (CHEBI:131834) has functional parent luteolin (CHEBI:15864)
luteolin 7-O-β-D-glucoside (CHEBI:27994) has functional parent luteolin (CHEBI:15864)
luteolin 7-O-(6-O-malonyl-β-D-glucoside) (CHEBI:6579) has functional parent luteolin (CHEBI:15864)
luteolin 7-O-neohesperidoside (CHEBI:31788) has functional parent luteolin (CHEBI:15864)
luteolin O-glucuronoside (CHEBI:25091) has functional parent luteolin (CHEBI:15864)
luteolin-4'-O-β-D-glucopyranoside (CHEBI:68986) has functional parent luteolin (CHEBI:15864)
luteolin-7-O-α-L-rhamnoside (CHEBI:70030) has functional parent luteolin (CHEBI:15864)
maysin (CHEBI:70206) has functional parent luteolin (CHEBI:15864)
orientin (CHEBI:7781) has functional parent luteolin (CHEBI:15864)
2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-olate luteolin-7-olate(1−) (CHEBI:57545) is conjugate base of luteolin (CHEBI:15864)
IUPAC Name
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
Synonyms Sources
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-benzopyrone ChemIDplus
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one ChemIDplus
3',4',5,7-Tetrahydroxyflavone KEGG COMPOUND
5,7,3',4'-Tetrahydroxyflavone KEGG COMPOUND
digitoflavone ChEBI
flacitran ChEBI
Luteolin KEGG COMPOUND
Luteolol ChemIDplus
Salifazide ChemIDplus
Database Links Databases
5734-TETRAHYDROXYFLAVONE MetaCyc
C00000674 KNApSAcK
C01514 KEGG COMPOUND
HMDB0005800 HMDB
LMPK12110006 LIPID MAPS
LSM-5229 LINCS
Luteolin Wikipedia
View more database links
Registry Numbers Types Sources
292084 Reaxys Registry Number Reaxys
491-70-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
19 June 2017