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Showing Compound Isobergapten (FDB006431)

Record Information
Version1.0
Creation date2010-04-08 22:07:08 UTC
Update date2019-11-26 03:01:09 UTC
Primary IDFDB006431
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsobergapten
DescriptionIsobergapten is a member of the class of compounds known as angular furanocoumarins. Angular furanocoumarins are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. Isobergapten is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Isobergapten can be found in parsnip, which makes isobergapten a potential biomarker for the consumption of this food product. Isobergapten is a non-carcinogenic (not listed by IARC) potentially toxic compound. Furocoumarin toxins can cause stomach ache and may also cause a painful skin reaction when contact with the parsnip plant is combined with UV rays from sunlight (L579) (T3DB).
CAS Number482-48-4
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP2.06ALOGPS
logP1.78ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area48.67 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity56.85 m³·mol⁻¹ChemAxon
Polarizability20.9 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H8O4
IUPAC name5-methoxy-2H-furo[2,3-h]chromen-2-one
InChI IdentifierInChI=1S/C12H8O4/c1-14-9-6-10-8(4-5-15-10)12-7(9)2-3-11(13)16-12/h2-6H,1H3
InChI KeyAJSPSRWWZBBIOR-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC2=C(C=CO2)C2=C1C=CC(=O)O2
Average Molecular Weight216.192
Monoisotopic Molecular Weight216.042258738
Classification
Description Belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct ParentAngular furanocoumarins
Alternative Parents
Substituents
  • Angular furanocoumarin
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-014i-2590000000-6d348f243bcb82176e412014-09-20View Spectrum
Predicted GC-MSIsobergapten, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ri-1920000000-05de33e02a65284633bdSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-a7aa4880d1b5f24edee22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-dde9ea19a79896e90ce22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rl-0910000000-979b64da744749c2c0c32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0190000000-a2793a15ec787ff5f1992016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0390000000-ff6e00dbfe68e7c3197f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-0910000000-20d69a4c35b8a7c99b712016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-7891ec2b2bad4a52dc5c2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-7891ec2b2bad4a52dc5c2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0300-1910000000-4d4d65f0f318e9f59f8c2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-f3b1b7cd2b3d93168c5f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-f3b1b7cd2b3d93168c5f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-0900000000-b64840080256c470ec902021-10-21View Spectrum
NMR
TypeDescriptionView
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID68082
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDISOBERGAPTEN
BIGG IDNot Available
KNApSAcK IDC00037321
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
Processing...
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).