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CHEBI:65646 - cochinchinone A

Default Structure
ChEBI IDCHEBI:65646
ChEBI Namecochinchinone A
Stars
DefinitionA 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.
Secondary ChEBI IDCHEBI:67550
Last Modified9 January 2014
DownloadsMolfile
FormulaC28H32O5
Net Charge0
Average Mass448.559
Monoisotopic Mass448.22497
SMILESCC(C)=CCC/C(C)=C/Cc1c(O)c(CC=C(C)C)c(O)c2c(=O)c3cc(O)ccc3oc12
InChIInChI=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+
InChIKeyZHJQVNDLFGICFY-VCHYOVAHSA-N
Species of MetaboliteComponentSourceComments
Cratoxylum cochinchinense (ncbitaxon:271749)
root (BTO:0001188) PubMed (16310231)
stem (BTO:0001300) PubMed (21428375) Methanolic extract of dried and ground stems
Roles Classification
Chemical Role:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
NF-kappaB inhibitor  An inhibitor of NF-κB (nuclear factor κ-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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)xanthoneChEBI
Registry NumbersSources
Reaxys:10399739Reaxys
Citations