CHEBI:134355 - auraptene

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ChEBI Name auraptene
ChEBI ID CHEBI:134355
Definition A member of the class of coumarins that is umbelliferone in which the phenolic hydrogen has been replaced by a geranyl group. Ii is isolated from several edible fruits and vegetables and exhibits a variety of therapeutic properties.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information
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Formula C19H22O3
Net Charge 0
Average Mass 298.377
Monoisotopic Mass 298.15689
InChI InChI=1S/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+
InChIKey RSDDHGSKLOSQFK-RVDMUPIBSA-N
SMILES C12=CC(=CC=C1C=CC(O2)=O)OC/C=C(/CCC=C(C)C)\C
Metabolite of Species Details
Citrus junos (NCBI:txid135197) Found in fruit (BTO:0000486). See: PubMed
Rutaceae (NCBI:txid23513) Found in fruit (BTO:0000486). See: PubMed
Citrus trifoliata (NCBI:txid37690) Found in fruit (BTO:0000486). 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): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
dopaminergic agent
A drug used for its effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.
gamma-secretase modulator
A modulator of gamma-secretase, one of the three endopeptidases that are specific for amyloid protein precursor and which have been identified based upon the region of the amyloid protein precursor which they cleave.
EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor
An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of mitogen-activated protein kinase (EC 2.7.11.24).
PPARalpha agonist
A PPAR modulator which activates the peroxisome proliferator-activated receptor-alpha.
matrix metalloproteinase inhibitor

Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
dopaminergic agent
A drug used for its effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
vulnerary
A drug used in treating and healing of wounds.
gastrointestinal drug
A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.
hepatoprotective agent
Any compound that is able to prevent damage to the liver.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing auraptene (CHEBI:134355) has functional parent umbelliferone (CHEBI:27510)
auraptene (CHEBI:134355) has role γ-secretase modulator (CHEBI:48668)
auraptene (CHEBI:134355) has role antihypertensive agent (CHEBI:35674)
auraptene (CHEBI:134355) has role antineoplastic agent (CHEBI:35610)
auraptene (CHEBI:134355) has role antioxidant (CHEBI:22586)
auraptene (CHEBI:134355) has role apoptosis inducer (CHEBI:68495)
auraptene (CHEBI:134355) has role dopaminergic agent (CHEBI:48560)
auraptene (CHEBI:134355) has role EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor (CHEBI:79091)
auraptene (CHEBI:134355) has role gastrointestinal drug (CHEBI:55324)
auraptene (CHEBI:134355) has role hepatoprotective agent (CHEBI:62868)
auraptene (CHEBI:134355) has role matrix metalloproteinase inhibitor (CHEBI:50664)
auraptene (CHEBI:134355) has role neuroprotective agent (CHEBI:63726)
auraptene (CHEBI:134355) has role plant metabolite (CHEBI:76924)
auraptene (CHEBI:134355) has role PPARα agonist (CHEBI:70782)
auraptene (CHEBI:134355) has role vulnerary (CHEBI:73336)
auraptene (CHEBI:134355) is a coumarins (CHEBI:23403)
auraptene (CHEBI:134355) is a monoterpenoid (CHEBI:25409)
IUPAC Name
7-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-2H-1-benzopyran-2-one
Synonyms Sources
(E)-7-((3,7-Dimethylocta-2,6-dien-1-yl)oxy)-2H-chromen-2-one NIST Chemistry WebBook
7-geranyloxycoumarin SUBMITTER
7-O-geranylumbelliferone SUBMITTER
Manual Xrefs Databases
1267148 ChemSpider
Auraptene Wikipedia
C00029763 KNApSAcK
HMDB0034054 HMDB
View more database links
Registry Numbers Types Sources
1291239 Reaxys Registry Number Reaxys
495-02-3 CAS Registry Number ChemIDplus
495-02-3 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
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Last Modified
19 April 2017