Auraptene (CHEM028166)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:15:51 UTC
Update Date2016-11-09 01:18:37 UTC
Accession NumberCHEM028166
Identification
Common NameAuraptene
ClassSmall Molecule
DescriptionA member of the class of coumarins that is umbelliferone in which the phenolic hydrogen has been replaced by a geranyl group.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.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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
Chemical FormulaC19H22O3
Average Molecular Mass298.376 g/mol
Monoisotopic Mass298.157 g/mol
CAS Registry Number495-02-3
IUPAC Name7-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-2H-chromen-2-one
Traditional Nameauraptene
SMILESCC(C)=CCC\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C1
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02u0-8890000000-e171be9caec4d2a11ee5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0040-0951000000-79a592191716b8a00de8Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-29a7bac9e8f94ca0d09cSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-08fr-1900000000-b149439e3218a537d0acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0490000000-32af6826fbefdf3a35acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07br-5960000000-d750ef85cd2d4a24a646Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9500000000-d8284943e9e7d046ea7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0390000000-50c66a59f956b01fdb9aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0930000000-1a7ac827ff79742e805cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1900000000-7a051e8b339080b6467dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-1940000000-dc613a802ac097906469Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-ebcff9e2f7b33fef0429Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0159-0900000000-833c0e8e483ddb0387a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0970000000-509fac58feb4fa761513Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-9500000000-190906af7b5b2a65c2f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0929-9700000000-4aeadfc84ff6db8dd015Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0034054
FooDB IDFDB012300
Phenol Explorer IDNot Available
KNApSAcK IDC00029763
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAuraptene
Chemspider ID1267148
ChEBI ID134355
PubChem Compound ID1550607
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
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