Record Information
Version1.0
Creation date2010-04-08 22:10:06 UTC
Update date2018-05-28 23:35:42 UTC
Primary IDFDB012300
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAuraptene
DescriptionIsolated from Citrus aurantium (Seville orange) and bael fruit (Aegle marmelos) Auraptene is a natural bioactive monoterpene coumarin ether. It was first isolated from members of the genus Citrus. Auraptene has shown a remarkable effect in the prevention of degenerative diseases. Many studies have reported the effect of auraptene as a chemopreventative agent against cancers of liver, skin, tongue, esophagus, and colon in rodent models. The effect in humans is not yet known. Auraptene is found in many foods, some of which are citrus, fruits, sweet orange, and lemon.
CAS Number495-02-3
Structure
Thumb
Synonyms
SynonymSource
(e)-7-((3,7-Dimethylocta-2,6-dien-1-yl)oxy)-2H-chromen-2-oneChEBI
7-GeranyloxycoumarinChEBI
7-O-GeranylumbelliferoneChEBI
7-(3,7-Dimethyl-2,6-octadienyl)oxy-2H-1-benzopyran-2-one, 9ciHMDB
7-([(2E)-3,7-Dimethyl-2,6-octadienyl]oxy)-2H-chromen-2-oneHMDB
7-[(3,7-Dimethyl-2,6-octadienyl)oxy]-(e)-coumarinHMDB
AuraptenHMDB
FeronialactoneHMDB
O-GeranylumbelliferoneHMDB
7-(Geranyloxy)coumarinMeSH
7-(3,7-Dimethyl-2,6-octadienyl)oxy-2H-1-benzopyran-2-one, 9CIdb_source
Coumarin, 7-[(3,7-dimethyl-2,6-octadienyl)oxy]-, (E)-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.0022 g/LALOGPS
logP5.85ALOGPS
logP4.65ChemAxon
logS-5.1ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity90.93 m³·mol⁻¹ChemAxon
Polarizability34.45 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC19H22O3
IUPAC name7-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-2H-chromen-2-one
InChI IdentifierInChI=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+
InChI KeyRSDDHGSKLOSQFK-RVDMUPIBSA-N
Isomeric SMILESCC(C)=CCC\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C1
Average Molecular Weight298.3762
Monoisotopic Molecular Weight298.15689457
Classification
Description belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Terpene lactone
  • Coumarin
  • Aromatic monoterpenoid
  • Benzopyran
  • Bicyclic monoterpenoid
  • Monoterpenoid
  • 1-benzopyran
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 76.48%; H 7.43%; O 16.09%DFC
Melting PointMp 68°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data329 () (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02u0-8890000000-e171be9caec4d2a11ee5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0040-0951000000-79a592191716b8a00de8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-29a7bac9e8f94ca0d09cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-08fr-1900000000-b149439e3218a537d0acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0490000000-32af6826fbefdf3a35acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07br-5960000000-d750ef85cd2d4a24a646View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9500000000-d8284943e9e7d046ea7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0390000000-50c66a59f956b01fdb9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0930000000-1a7ac827ff79742e805cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1900000000-7a051e8b339080b6467dView in MoNA
ChemSpider ID1267148
ChEMBL IDCHEMBL307341
KEGG Compound IDNot Available
Pubchem Compound ID1550607
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34054
CRC / DFC (Dictionary of Food Compounds) IDHFS51-H:HFS51-H
EAFUS IDNot Available
Dr. Duke IDAURAPTENE|AURAPTEN
BIGG IDNot Available
KNApSAcK IDC00029763
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAuraptene
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti aggregantDUKE
anti peroxidantDUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti superoxidogenicDUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
chemopreventive inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
quinone-reductase inducerDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).