CHEBI:65646 - cochinchinone A

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ChEBI Name cochinchinone A
ChEBI ID CHEBI:65646
Definition A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1, 3 and 7, a prenyl group at position 2 and a geranyl group at position 4. Isolated from Cratoxylum cochinchinense, it exhibits cytotoxic and antioxidant activities.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:67550
Supplier Information
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Formula C28H32O5
Net Charge 0
Average Mass 448.55070
Monoisotopic Mass 448.22497
InChI InChI=1S/C28H32O5/c1-16(2)7-6-8-18(5)10-13-21-25(30)20(12-9-17(3)4)26(31)24-27(32)22-15-19(29)11-14-23(22)33-28(21)24/h7,9-11,14-15,29-31H,6,8,12-13H2,1-5H3/b18-10+
InChIKey ZHJQVNDLFGICFY-VCHYOVAHSA-N
SMILES CC(C)=CCC\C(C)=C\Cc1c(O)c(CC=C(C)C)c(O)c2c1oc1ccc(O)cc1c2=O
Metabolite of Species Details
Cratoxylum cochinchinense (NCBI:txid271749) Found in root (BTO:0001188). See: PubMed
Cratoxylum cochinchinense (NCBI:txid271749) Found in stem (BTO:0001300). Methanolic extract of dried and ground stems 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): NF-kappaB inhibitor
An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
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 cochinchinone A (CHEBI:65646) has role antineoplastic agent (CHEBI:35610)
cochinchinone A (CHEBI:65646) has role antioxidant (CHEBI:22586)
cochinchinone A (CHEBI:65646) has role NF-κB inhibitor (CHEBI:73240)
cochinchinone A (CHEBI:65646) has role plant metabolite (CHEBI:76924)
cochinchinone A (CHEBI:65646) is a polyphenol (CHEBI:26195)
cochinchinone A (CHEBI:65646) is a xanthones (CHEBI:51149)
IUPAC Name
4-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-1,3,7-trihydroxy-2-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one
Synonym Source
1,3,7-trihydroxy-2-(3-methyl-2-butenyl)-4-(3,7-dimethyl-2,6-octadienyl)xanthone ChEBI
Registry Number Type Source
10399739 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
16310231 PubMed citation Europe PMC
21428375 PubMed citation Europe PMC
Last Modified
09 January 2014