CHEBI:80830 - (E,E)-germacrone

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ChEBI Name (E,E)-germacrone
ChEBI ID CHEBI:80830
ChEBI ASCII Name (E,E)-germacrone
Definition A germacrane sesquiterpenoid that has formula C15H22O. It is a natural product found in traditional medicinal plants of the family Zingiberaceae. The compound exhibits a range of pharmacological activities including anti-inflammatory, anticancer, antiviral, anti-androgenic, antioxidant, antimicrobial, antifungal, neuroprotective and insecticidal activities.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H22O
Net Charge 0
Average Mass 218.340
Monoisotopic Mass 218.16707
InChI InChI=1S/C15H22O/c1-11(2)14-9-8-12(3)6-5-7-13(4)10-15(14)16/h7-8H,5-6,9-10H2,1-4H3/b12-8+,13-7+
InChIKey CAULGCQHVOVVRN-SWZPTJTJSA-N
SMILES CC(C)=C1C\C=C(C)\CC\C=C(C)\CC1=O
Metabolite of Species Details
Rhododendron thymifolium (IPNI:333480-1) See: PubMed
Curcuma aeruginosa (NCBI:txid136205) See: PubMed
Curcuma longa (NCBI:txid136217) See: DOI
Curcuma phaeocaulis (NCBI:txid136218) Found in rhizome (BTO:0001181). See: PubMed
Curcuma wenyujin (NCBI:txid136221) See: PubMed
Geranium macrorrhizum (NCBI:txid28963) See: DOI
Myrica gale (NCBI:txid29739) Found in leaf (BTO:0000713). See: DOI
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): volatile oil component
Any plant metabolite that is found naturally as a component of a volatile oil.
antiviral agent
A substance that destroys or inhibits replication of viruses.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
autophagy inducer
Any compound that induces the process of autophagy (the self-digestion of one or more components of a cell through the action of enzymes originating within the same cell).
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
androgen antagonist
A compound which inhibits or antagonises the biosynthesis or actions of androgens.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
Application(s): insecticide
Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
androgen antagonist
A compound which inhibits or antagonises the biosynthesis or actions of androgens.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
antitussive
An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.
antifeedant
A substance that prevents pests from feeding.
hepatoprotective agent
Any compound that is able to prevent damage to the liver.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (E,E)-germacrone (CHEBI:80830) has role androgen antagonist (CHEBI:35497)
(E,E)-germacrone (CHEBI:80830) has role anti-inflammatory agent (CHEBI:67079)
(E,E)-germacrone (CHEBI:80830) has role antifeedant (CHEBI:22583)
(E,E)-germacrone (CHEBI:80830) has role antifungal agent (CHEBI:35718)
(E,E)-germacrone (CHEBI:80830) has role antimicrobial agent (CHEBI:33281)
(E,E)-germacrone (CHEBI:80830) has role antineoplastic agent (CHEBI:35610)
(E,E)-germacrone (CHEBI:80830) has role antioxidant (CHEBI:22586)
(E,E)-germacrone (CHEBI:80830) has role antitussive (CHEBI:51177)
(E,E)-germacrone (CHEBI:80830) has role antiviral agent (CHEBI:22587)
(E,E)-germacrone (CHEBI:80830) has role apoptosis inducer (CHEBI:68495)
(E,E)-germacrone (CHEBI:80830) has role autophagy inducer (CHEBI:138880)
(E,E)-germacrone (CHEBI:80830) has role hepatoprotective agent (CHEBI:62868)
(E,E)-germacrone (CHEBI:80830) has role insecticide (CHEBI:24852)
(E,E)-germacrone (CHEBI:80830) has role neuroprotective agent (CHEBI:63726)
(E,E)-germacrone (CHEBI:80830) has role plant metabolite (CHEBI:76924)
(E,E)-germacrone (CHEBI:80830) has role volatile oil component (CHEBI:27311)
(E,E)-germacrone (CHEBI:80830) is a germacrane sesquiterpenoid (CHEBI:68588)
(E,E)-germacrone (CHEBI:80830) is a olefinic compound (CHEBI:78840)
IUPAC Name
(3E,7E)-3,7-dimethyl-10-(propan-2-ylidene)cyclodeca-3,7-dien-1-one
Synonyms Sources
(3E,7E)-3,7-dimethyl-10-(1-methylethylidene)-3,7-cyclodecadien-1-one ChEBI
(E,E)-germacrone KNApSAcK
germacron ChemIDplus
germacrone ChemIDplus
trans,trans-3,7-dimethyl-10-isopropylidene-3,7-cyclodecadien-1-one ChEBI
Manual Xrefs Databases
4940991 ChemSpider
C00011728 KNApSAcK
C16966 KEGG COMPOUND
FDB005347 FooDB
Germacrone Wikipedia
View more database links
Registry Numbers Types Sources
2047453 Reaxys Registry Number Reaxys
6902-91-6 CAS Registry Number ChemIDplus
6902-91-6 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
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Last Modified
21 April 2021