Bergapten (CHEM003680)

Record Information
Version1.0
Creation Date2014-09-11 02:06:26 UTC
Update Date2026-08-18 21:53:20 UTC
Accession NumberCHEM003680
Identification
Common NameBergapten
ClassSmall Molecule
Description
Bergapten is found in anise. Bergapten is a major constituent of bergamot oil (Citrus bergamia). Bergapten is present in celery, especially the outer leaves, and other common grocery vegetables. Implicated in photodermatitis among grocery workers Bergapten has been shown to exhibit anti-convulsant function (1). Bergapten belongs to the family of Furanocoumarins. These are polycyclic aromatic compounds containing a furan ring fused to a coumarin moeity.
Contaminant Sources
  • FooDB Chemicals
  • IARC Carcinogens Group 2A
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Ether
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-Methoxy-7H-furo[3,2-g][1]benzopyran-7-oneChEBI
5-MethoxyfuranocoumarinChEBI
5-MethoxypsoraleneChEBI
BergapteneChEBI
HeraclinChEBI
MajudinChEBI
O-MethylbergaptolChEBI
5-MethoxypsoralenKegg
PentadermKegg
4-Methoxy-7H-furo(3,2-g)(1)benzopyran-7-oneHMDB
4-Methoxy-7H-furo[3,2-g]benzopyran-7-oneHMDB
4-Methoxy-7H-furo[3,2-g]chromen-7-oneHMDB
4-Methoxy-furo[3,2-g]chromen-7-oneHMDB
4-methoxyfuro[3,2-g]Benzopyrane-7-oneHMDB
5-Methoxy psoralenHMDB, MeSH
5-Methoxy-6,7-furanocoumarinHMDB
5-Methoxypsoralen (obsol.)HMDB
5-MOPHMDB
6-Hydroxy-4-methoxy-5-benzofuranacrylic acid, gamma-lactoneHMDB
BergaptanHMDB
PsoradermHMDB
BergaptenChEBI
5 MethoxypsoralenMeSH
5 Methoxy psoralenMeSH
Chemical FormulaC12H8O4
Average Molecular Mass216.192 g/mol
Monoisotopic Mass216.042 g/mol
CAS Registry Number484-20-8
IUPAC Name4-methoxy-7H-furo[3,2-g]chromen-7-one
Traditional Namebergapten
SMILESCOC1=C2C=CC(=O)OC2=CC2=C1C=CO2
InChI IdentifierInChI=1S/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H3
InChI KeyBGEBZHIAGXMEMV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 5-methoxypsoralens. These are psoralens containing a methoxy group attached at the C5 position of the psoralen group.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct Parent5-methoxypsoralens
Alternative Parents
Substituents
  • 5-methoxypsoralen
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point188 °C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP2.12ALOGPS
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
Polarizability20.87 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2A, probably carcinogenic to humans. (2)
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB12216
HMDB IDHMDB0030637
FooDB IDFDB002542
Phenol Explorer ID717
KNApSAcK IDC00000575
BiGG IDNot Available
BioCyc ID5-METHOXYFURANOCOUMARIN
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBergapten
Chemspider ID2265
ChEBI ID18293
PubChem Compound ID2355
Kegg Compound IDC01557
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20433072
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22611312
3. Luszczki JJ, Andres-Mach M, Glensk M, Skalicka-Wozniak K: Anticonvulsant effects of four linear furanocoumarins, bergapten, imperatorin, oxypeucedanin, and xanthotoxin, in the mouse maximal electroshock-induced seizure model: a comparative study. Pharmacol Rep. 2010 Nov-Dec;62(6):1231-6.
4. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.