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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:49:57 UTC
Update Date2022-03-07 02:53:58 UTC
HMDB IDHMDB0034054
Secondary Accession Numbers
  • HMDB34054
Metabolite Identification
Common NameAuraptene
DescriptionAuraptene is found in citrus. Auraptene is isolated 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
Structure
Data?1563862502
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 Weight298.3762
Monoisotopic Molecular Weight298.15689457
IUPAC Name7-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-2H-chromen-2-one
Traditional Nameauraptene
CAS Registry Number495-02-3
SMILES
CC(C)=CCC\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C1
InChI Identifier
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+
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
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point68 °CNot Available
Boiling Point455.50 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.17 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.690 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available158.294http://allccs.zhulab.cn/database/detail?ID=AllCCS00001254
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+174.0831661259
DarkChem[M-H]-173.70231661259
DeepCCS[M+H]+177.44630932474
DeepCCS[M-H]-175.08830932474
DeepCCS[M-2H]-208.21630932474
DeepCCS[M+Na]+183.93430932474
AllCCS[M+H]+172.332859911
AllCCS[M+H-H2O]+169.032859911
AllCCS[M+NH4]+175.332859911
AllCCS[M+Na]+176.132859911
AllCCS[M-H]-177.632859911
AllCCS[M+Na-2H]-177.132859911
AllCCS[M+HCOO]-176.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AurapteneCC(C)=CCC\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C13361.4Standard polar33892256
AurapteneCC(C)=CCC\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C12501.8Standard non polar33892256
AurapteneCC(C)=CCC\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C12628.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Auraptene GC-MS (Non-derivatized) - 70eV, Positivesplash10-02u0-8890000000-e171be9caec4d2a11ee52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Auraptene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Auraptene LC-ESI-qTof , Positive-QTOFsplash10-0040-0951000000-79a592191716b8a00de82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Auraptene , positive-QTOFsplash10-03di-0900000000-29a7bac9e8f94ca0d09c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Auraptene , positive-QTOFsplash10-08fr-1900000000-b149439e3218a537d0ac2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auraptene 10V, Positive-QTOFsplash10-0002-0490000000-32af6826fbefdf3a35ac2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auraptene 20V, Positive-QTOFsplash10-07br-5960000000-d750ef85cd2d4a24a6462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auraptene 40V, Positive-QTOFsplash10-0gb9-9500000000-d8284943e9e7d046ea7e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auraptene 10V, Negative-QTOFsplash10-0002-0390000000-50c66a59f956b01fdb9a2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auraptene 20V, Negative-QTOFsplash10-03di-0930000000-1a7ac827ff79742e805c2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auraptene 40V, Negative-QTOFsplash10-014i-1900000000-7a051e8b339080b6467d2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auraptene 10V, Negative-QTOFsplash10-03dj-1940000000-dc613a802ac0979064692021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auraptene 20V, Negative-QTOFsplash10-03di-0900000000-ebcff9e2f7b33fef04292021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auraptene 40V, Negative-QTOFsplash10-0159-0900000000-833c0e8e483ddb0387a62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auraptene 10V, Positive-QTOFsplash10-03dj-0970000000-509fac58feb4fa7615132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auraptene 20V, Positive-QTOFsplash10-03ea-9500000000-190906af7b5b2a65c2f42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auraptene 40V, Positive-QTOFsplash10-0929-9700000000-4aeadfc84ff6db8dd0152021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012300
KNApSAcK IDC00029763
Chemspider ID1267148
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAuraptene
METLIN IDNot Available
PubChem Compound1550607
PDB IDNot Available
ChEBI ID134355
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1011441
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. de Medina P, Genovese S, Paillasse MR, Mazaheri M, Caze-Subra S, Bystricky K, Curini M, Silvente-Poirot S, Epifano F, Poirot M: Auraptene is an inhibitor of cholesterol esterification and a modulator of estrogen receptors. Mol Pharmacol. 2010 Nov;78(5):827-36. doi: 10.1124/mol.110.065250. Epub 2010 Aug 11. [PubMed:20702762 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.