CHEBI:69356 - centaureidin

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ChEBI Name centaureidin
ChEBI ID CHEBI:69356
Definition A trihydroxyflavone that consists of quercetagetin in which the hydroxy groups at positions 3, 6 and 4' have been replaced by methoxy groups. It has been isolated from Eremophila mitchellii and Athroisma proteiforme.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H16O8
Net Charge 0
Average Mass 360.31480
Monoisotopic Mass 360.085
InChI InChI=1S/C18H16O8/c1-23-11-5-4-8(6-9(11)19)16-18(25-3)15(22)13-12(26-16)7-10(20)17(24-2)14(13)21/h4-7,19-21H,1-3H3
InChIKey BZXULYMZYPRZOG-UHFFFAOYSA-N
SMILES COc1ccc(cc1O)-c1oc2cc(O)c(OC)c(O)c2c(=O)c1OC
Metabolite of Species Details
Athroisma proteiforme (IPNI:182889-1) Found in aerial part (BTO:0001658). Ethyl alcohol extract of dried, ground aerial parts. See: PubMed
Eremophila mitchellii (IPNI:585196-1) Found in leaf (BTO:0000713). n-Hexane,Methylene dichloride and methanolic extarct of airdried and ground leaves See: PubMed
Roles Classification
Biological Role(s): cyclooxygenase 1 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing centaureidin (CHEBI:69356) has role antineoplastic agent (CHEBI:35610)
centaureidin (CHEBI:69356) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
centaureidin (CHEBI:69356) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
centaureidin (CHEBI:69356) has role plant metabolite (CHEBI:76924)
centaureidin (CHEBI:69356) is a trihydroxyflavone (CHEBI:27116)
centaureidin (CHEBI:69356) is a trimethoxyflavone (CHEBI:27124)
IUPAC Name
5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6-dimethoxy-4H-chromen-4-one
Synonyms Sources
5,7,3'-trihydroxy-3,6,4'-trimethoxyflavone LIPID MAPS
5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6-dimethoxy-4H-1-benzopyran-4-one ChemIDplus
desmethoxycentaureidine LIPID MAPS
quercetagetin 3,6,4'-trimethyl ether ChEBI
Database Links Databases
Centaureidin Wikipedia
LMPK12113000 LIPID MAPS
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Registry Numbers Types Sources
17313-52-9 CAS Registry Number ChemIDplus
347389 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11730880 PubMed citation Europe PMC
19107850 PubMed citation Europe PMC
19639540 PubMed citation Europe PMC
20804828 PubMed citation Europe PMC
21877688 PubMed citation Europe PMC
21995542 PubMed citation Europe PMC
22537643 PubMed citation Europe PMC
Last Modified
15 January 2014