CHEBI:80830 - (E,E)-germacrone

ChEBI IDCHEBI:80830
ChEBI Name(E,E)-germacrone
Stars
ASCII Name(E,E)-germacrone
DefinitionA 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.
Last Modified21 April 2021
DownloadsMolfile
FormulaC15H22O
Net Charge0
Average Mass218.340
Monoisotopic Mass218.16707
SMILESCC(C)=C1C/C=C(\C)CC/C=C(\C)CC1=O
InChIInChI=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+
InChIKeyCAULGCQHVOVVRN-SWZPTJTJSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Curcuma wenyujin (ncbitaxon:136221) - PubMed (2938786)
Curcuma aeruginosa (ncbitaxon:136205) - PubMed (29159692)
Curcuma phaeocaulis (ncbitaxon:136218) rhizome (BTO:0001181) PubMed (33688362)
Geranium macrorrhizum (ncbitaxon:28963) - DOI (10.1007/s00606-020-01649-9)
Rhododendron thymifolium (IPNI:333480-1) - PubMed (33678144)
Curcuma longa (ncbitaxon:136217) - DOI (10.1371/journal.pone.0194284)
Myrica gale (ncbitaxon:29739) leaf (BTO:0000713) DOI (10.1007/BF01261457)
Roles Classification
Chemical Role:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Roles:
androgen antagonist  A compound which inhibits or antagonises the biosynthesis or actions of androgens.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
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.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
volatile oil component  Any plant metabolite that is found naturally as a component of a volatile oil.
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).
Applications:
androgen antagonist  A compound which inhibits or antagonises the biosynthesis or actions of androgens.
antifeedant  A substance that prevents pests from feeding.
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.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
hepatoprotective agent  Any compound that is able to prevent damage to the liver.
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
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.
ChEBI Ontology
Outgoing Relation(s)
(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  Source
germacronChemIDplus
(E,E)-germacroneKNApSAcK
germacroneChemIDplus
(3E,7E)-3,7-dimethyl-10-(1-methylethylidene)-3,7-cyclodecadien-1-oneChEBI
trans,trans-3,7-dimethyl-10-isopropylidene-3,7-cyclodecadien-1-oneChEBI
Manual XrefsDatabases
C16966KEGG COMPOUND
FDB005347FooDB
C00011728KNApSAcK
GermacroneWikipedia
4940991ChemSpider
Registry NumbersSources
Reaxys:2047453Reaxys
CAS:6902-91-6ChemIDplus
CAS:6902-91-6NIST Chemistry WebBook
Citations