Record Information
Version1.0
Creation date2010-04-08 22:09:54 UTC
Update date2019-11-26 03:05:47 UTC
Primary IDFDB011939
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBergamottin
DescriptionConstituent of bergamot oiland is also from lemon oil and oils of other Citrus subspecies and carrot (Daucus carota) Bergamottin is a natural furanocoumarin found principally in grapefruit juice. It is also found in the oil of bergamot, from which it was first isolated and from which its name is derived. To a lesser extent, bergamottin is also present in the essential oils of other citrus fruits. Along with the chemically related compound 6?,7?-dihydroxybergamottin, it is believed to be responsible for the grapefruit juice effect in which the consumption of the juice affects the metabolism of a variety of pharmaceutical drugs.
CAS Number7380-40-7
Structure
Thumb
Synonyms
SynonymSource
4-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one, 9ciHMDB
5-GeranoxypsoralenHMDB
5-GeranyloxypsoralenHMDB
BergamotinHMDB
BergamotineHMDB
BergaptinHMDB
Bergaptol geranyl etherHMDB
4-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP5.3ALOGPS
logP4.81ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area48.67 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity99.77 m³·mol⁻¹ChemAxon
Polarizability37.47 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H22O4
IUPAC name4-{[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one
InChI IdentifierInChI=1S/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-16-7-8-20(22)25-19(16)13-18-17(21)10-12-23-18/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9-
InChI KeyDBMJZOMNXBSRED-DHDCSXOGSA-N
Isomeric SMILESCC(C)=CCC\C(C)=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O2
Average Molecular Weight338.403
Monoisotopic Molecular Weight338.151809188
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
  • Linear furanocoumarin
  • Furanocoumarin
  • Psoralen
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Monoterpenoid
  • Aromatic monoterpenoid
  • Benzofuran
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 74.54%; H 6.55%; O 18.91%DFC
Melting PointMp 59-61° (54°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gi0-9563000000-1489fb332877b9483715JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1449000000-f1cb80e88623323efd78JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-7974000000-8dc8885c8ce63b6b8f05JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9420000000-d4a732b567f78ee66d36JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0059000000-6c5381fc4c44ea7b815bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0392000000-aef5d498f581369a1495JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0910000000-f3479b11ac7337bdd5d4JSpectraViewer
ChemSpider ID5584831
ChEMBL IDCHEMBL1571785
KEGG Compound IDNot Available
Pubchem Compound ID7251175
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33782
CRC / DFC (Dictionary of Food Compounds) IDHBX86-S:HBX86-S
EAFUS IDNot Available
Dr. Duke ID5-GERANYL-OXYPSORALEN|BERGAMOTTIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDBergamottin
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
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
cytochrome-P450 inhibitor50183 An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.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).