Record Information
Version1.0
Creation date2010-04-08 22:05:25 UTC
Update date2019-11-26 02:57:35 UTC
Primary IDFDB002543
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBergaptol
DescriptionBergaptol, also known as 5-hydroxypsoralen, belongs to the class of organic compounds known as 5-hydroxypsoralens. These are psoralens containing a hydroxyl group attached at the C5 position of the psoralen group. Bergaptol is an extremely weak basic (essentially neutral) compound (based on its pKa). Bergaptol has been detected, but not quantified in, several different foods, such as small-leaf lindens, strawberry guava, gingers, java plums, and purple mangosteens. This could make bergaptol a potential biomarker for the consumption of these foods. Bergaptol is a potentially toxic compound.
CAS Number486-60-2
Structure
Thumb
Synonyms
SynonymSource
5-HydroxyfuranocoumarinChEBI
5-HydroxypsoralenChEBI
4-Hydroxy-7H-furo[3,2-g]chromen-7-oneHMDB
4-Hydroxy-7H-furo[3,2-g]chromen-7-one (acd/name 4.0)HMDB
5-HYDROXY-psoralinHMDB
BergaptolsHMDB
4-Hydroxy-7H-furo(3,2-g)chromen-7-oneMeSH
4-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-one, 9CIdb_source
4-hydroxy-7H-furo[3,2-g]chromen-7-onebiospider
4-Hydroxypsoralendb_source
7H-Furo(3,2-g)(1)benzopyran-7-one, 4-hydroxy- (8CI)(9CI)biospider
7H-Furo[3,2-g][1]benzopyran-7-one, 4-hydroxy-biospider
PSORALIN, 5-HYDROXY-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.89 g/LALOGPS
logP1.86ALOGPS
logP1.64ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.45ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.67 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity52.37 m³·mol⁻¹ChemAxon
Polarizability18.94 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC11H6O4
IUPAC name4-hydroxy-7H-furo[3,2-g]chromen-7-one
InChI IdentifierInChI=1S/C11H6O4/c12-10-2-1-6-9(15-10)5-8-7(11(6)13)3-4-14-8/h1-5,13H
InChI KeyGIJHDGJRTUSBJR-UHFFFAOYSA-N
Isomeric SMILESOC1=C2C=CC(=O)OC2=CC2=C1C=CO2
Average Molecular Weight202.165
Monoisotopic Molecular Weight202.026608673
Classification
Description belongs to the class of organic compounds known as 5-hydroxypsoralens. These are psoralens containing a hydroxyl group attached at the C5 position of the psoralen group.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct Parent5-hydroxypsoralens
Alternative Parents
Substituents
  • 5-hydroxypsoralen
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Pyran
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Foods

Fruits and vegetables:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 65.35%; H 2.99%; O 31.66%DFC
Melting PointMp 277-278°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, Positivesplash10-05fr-1910000000-e6a47789c6cb25ff3a46JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-4090000000-566be005cc2959d86652JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-0910000000-cc054eaed6fc83b4a27aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0910000000-cc054eaed6fc83b4a27aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0190000000-ac460f53d5cb80eb5044JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0490000000-b86689b17be620c214e6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-1900000000-6193deca8502dc532307JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0190000000-f8c060c4143f0fd9068cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0490000000-f83b2cbc9d5dea16671fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-1900000000-6a70dde5da85af79bd84JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC00758
Pubchem Compound ID5280371
Pubchem Substance IDNot Available
ChEBI ID17377
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCMH82-I:CMH82-I
EAFUS IDNot Available
Dr. Duke IDBERGAPTOL
BIGG IDNot Available
KNApSAcK IDC00000581
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.