CHEBI:15864 - luteolin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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 anti-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
Supplier Information
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C15H10O6
Net Charge 0
Average Mass 286.239
Monoisotopic Mass 286.04774
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 OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C(O)=C1
Metabolite of Species Details
Arabidopsis thaliana (NCBI:txid3702) Found in cell suspension culture (BTO:0000221). From MetaboLights See: MetaboLights Study
Arabidopsis thaliana (NCBI:txid3702) From MetaboLights See: MetaboLights Study
Brassica napus (NCBI:txid3708) Found in leaf lamina (BTO:0000719). From MetaboLights See: MetaboLights Study
Brassica napus (NCBI:txid3708) From MetaboLights See: MetaboLights Study
Brassica napus (NCBI:txid3708) From MetaboLights See: MetaboLights Study
Olea europaea (NCBI:txid4146) Found in leaf (BTO:0000713). Methanolic extract of dried olive leaves See: PubMed
Sorghum bicolor (NCBI:txid4558) From MetaboLights See: MetaboLights Study
Mimosa diplotricha (NCBI:txid512270) Found in aerial part (BTO:0001658). Ethanolic extract of aerial part See: PubMed
Cirsium japonicum (NCBI:txid516546) Found in whole plant (BTO:0001461). Hot methanolic extract of dried whole plant See: PubMed
Lepisorus ussuriensis (NCBI:txid699700) Found in whole plant (BTO:0001461). See: PubMed
Roles Classification
Chemical Role(s): radical scavenger
A role played by a substance that can react readily with, and thereby eliminate, radicals.
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
An 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.
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
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.
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
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 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 immunomodulator (CHEBI:50846)
luteolin (CHEBI:15864) has role nephroprotective agent (CHEBI:76595)
luteolin (CHEBI:15864) has role plant metabolite (CHEBI:76924)
luteolin (CHEBI:15864) has role radical scavenger (CHEBI:48578)
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
Manual Xrefs Databases
4444102 ChemSpider
5734-TETRAHYDROXYFLAVONE MetaCyc
C00000674 KNApSAcK
C01514 KEGG COMPOUND
DB15584 DrugBank
FDB013255 FooDB
HMDB0005800 HMDB
LMPK12110006 LIPID MAPS
LSM-5229 LINCS
LU2 PDBeChem
Luteolin Wikipedia
View more database links
Registry Numbers Types Sources
292084 Reaxys Registry Number Reaxys
491-70-3 CAS Registry Number ChemIDplus
491-70-3 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
11478688 PubMed citation Europe PMC
11897650 PubMed citation Europe PMC
14574115 PubMed citation Europe PMC
18720166 PubMed citation Europe PMC
18946424 PubMed citation Europe PMC
18991571 PubMed citation Europe PMC
19263826 PubMed citation Europe PMC
19509250 PubMed citation Europe PMC
19854181 PubMed citation Europe PMC
21899269 PubMed citation Europe PMC
22391103 PubMed citation Europe PMC
22749133 PubMed citation Europe PMC
22794353 PubMed citation Europe PMC
22842046 PubMed citation Europe PMC
23035972 PubMed citation Europe PMC
23229294 PubMed citation Europe PMC
23574272 PubMed citation Europe PMC
26020516 PubMed citation Europe PMC
26322379 PubMed citation Europe PMC
27595800 PubMed citation Europe PMC
27764981 PubMed citation Europe PMC
27853236 PubMed citation Europe PMC
27878246 PubMed citation Europe PMC
27879665 PubMed citation Europe PMC
27886116 PubMed citation Europe PMC
27919958 PubMed citation Europe PMC
27927066 PubMed citation Europe PMC
27959422 PubMed citation Europe PMC
28004344 PubMed citation Europe PMC
28029146 PubMed citation Europe PMC
28031430 PubMed citation Europe PMC
28035396 PubMed citation Europe PMC
28067377 PubMed citation Europe PMC
28069121 PubMed citation Europe PMC
28071803 PubMed citation Europe PMC
28090531 PubMed citation Europe PMC
28096694 PubMed citation Europe PMC
28101184 PubMed citation Europe PMC
28101223 PubMed citation Europe PMC
28110189 PubMed citation Europe PMC
28111945 PubMed citation Europe PMC
28112209 PubMed citation Europe PMC
28113103 PubMed citation Europe PMC
28166217 PubMed citation Europe PMC
29423013 PubMed citation Europe PMC
30624931 PubMed citation Europe PMC
32883638 PubMed citation Europe PMC
Last Modified
02 June 2021