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Showing Compound Auraptene (FDB012300)

Record Information
Version1.0
Creation date2010-04-08 22:10:06 UTC
Update date2019-11-26 03:06:32 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
MOLSDFPDBSMILESInChI
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAuraptene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02u0-8890000000-e171be9caec4d2a11ee5Spectrum
Predicted GC-MSAuraptene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0040-0951000000-79a592191716b8a00de82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-29a7bac9e8f94ca0d09c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-08fr-1900000000-b149439e3218a537d0ac2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0490000000-32af6826fbefdf3a35ac2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07br-5960000000-d750ef85cd2d4a24a6462016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9500000000-d8284943e9e7d046ea7e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0390000000-50c66a59f956b01fdb9a2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0930000000-1a7ac827ff79742e805c2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1900000000-7a051e8b339080b6467d2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-1940000000-dc613a802ac0979064692021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-ebcff9e2f7b33fef04292021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0159-0900000000-833c0e8e483ddb0387a62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0970000000-509fac58feb4fa7615132021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-9500000000-190906af7b5b2a65c2f42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0929-9700000000-4aeadfc84ff6db8dd0152021-09-22View Spectrum
NMRNot Available
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
Food Biomarker OntologyNot Available
VMH 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-aggregantAn agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots.DUKE
Anti peroxidantAn agent that prevents oxygen atom and peroxide formation, reducing oxidative stress and cell damage. It plays a biological role in protecting cells from free radicals. Therapeutically, it's used to manage conditions like cancer, Alzheimer's, and atherosclerosis, with key medical applications in neuroprotection, cardiovascular health, and anti-aging.DUKE
Anti-spasmodic52217 An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.DUKE
Anti superoxidogenicAn agent that inhibits the production of superoxides, reducing oxidative stress and inflammation. It plays a biological role in protecting cells from damage. Therapeutically, it has applications in managing neurodegenerative and inflammatory diseases, with key medical uses in treating conditions such as Alzheimer's, Parkinson's, and arthritis.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Chemopreventive inhibitor35222 An agent that blocks or suppresses the development of cancer, reducing tumor growth and progression. Therapeutically, it is used to prevent cancer in high-risk individuals, and medically, it is applied to manage conditions such as colon, breast, and prostate cancers, by inhibiting carcinogenesis.DUKE
Quinone-reductase inducerAn agent that stimulates quinone reductase enzymatic activity, enhancing cellular antioxidant defenses and protecting against carcinogens, with therapeutic applications in cancer chemoprevention and potential uses in managing oxidative stress-related diseases.DUKE
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).