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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:06 UTC
Update Date2022-03-07 02:52:38 UTC
HMDB IDHMDB0030637
Secondary Accession Numbers
  • HMDB30637
Metabolite Identification
Common NameBergapten
DescriptionBergapten, also known as O-methylbergaptol or heraclin, 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. Bergapten is found, on average, in the highest concentration within a few different foods, such as anises, figs, and parsnips and in a lower concentration in carrots, fennels, and celery stalks. Bergapten has also been detected, but not quantified, in several different foods, such as coconuts, pepper (c. frutescens), corianders, sesbania flowers, and cardamoms. This could make bergapten a potential biomarker for the consumption of these foods. It is also found in rose hip, sweet marjoram, greenthread tea, and tartary buckwheat. Bergapten is a potentially toxic compound. Bergapten is a major constituent of bergamot oil (Citrus bergamia). Present in celery, especially the outer leaves, and other common grocery vegetables. Implicated in photodermatitis among grocery workers. Bergapten was under investigation in clinical trial NCT00533195 "Comparison of UVA1 Phototherapy Versus Photochemotherapy for Patients With Severe Generalized Atopic Dermatitis".
Structure
Data?1563862015
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 Weight216.192
Monoisotopic Molecular Weight216.042258738
IUPAC Name4-methoxy-7H-furo[3,2-g]chromen-7-one
Traditional Namebergapten
CAS Registry Number484-20-8
SMILES
COC1=C2C=CC(=O)OC2=CC2=C1C=CO2
InChI Identifier
InChI=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
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point188 °CNot Available
Boiling Point412.00 to 413.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility810.5 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.035 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+148.66431661259
DarkChem[M-H]-148.08731661259
DeepCCS[M+H]+145.70730932474
DeepCCS[M-H]-143.31130932474
DeepCCS[M-2H]-177.05530932474
DeepCCS[M+Na]+151.67430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BergaptenCOC1=C2C=CC(=O)OC2=CC2=C1C=CO22929.6Standard polar33892256
BergaptenCOC1=C2C=CC(=O)OC2=CC2=C1C=CO22004.0Standard non polar33892256
BergaptenCOC1=C2C=CC(=O)OC2=CC2=C1C=CO22056.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Bergapten EI-B (Non-derivatized)splash10-01b9-3890000000-a8341e87fa6830843ef72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Bergapten GC-EI-TOF (Non-derivatized)splash10-00y1-3940000000-1492cacf3f4395e9f66c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Bergapten EI-B (Non-derivatized)splash10-01b9-3890000000-a8341e87fa6830843ef72018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Bergapten GC-EI-TOF (Non-derivatized)splash10-00y1-3940000000-1492cacf3f4395e9f66c2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bergapten GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1920000000-1f376a338d3e061368862017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bergapten GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-01b9-7950000000-e77dc647c2fa0ccbb1772014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-qTof , Positive-QTOFsplash10-0udi-0950000000-b19407bde306a78efe772017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-QTOF , positive-QTOFsplash10-014i-0090000000-927b1385246a4f40d60d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-QTOF , positive-QTOFsplash10-0uxr-0090000000-53c9077581fc1617f7892017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-QTOF , positive-QTOFsplash10-0udi-0290000000-d6eb013ef1071457a5b12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-ITFT , positive-QTOFsplash10-0gb9-0090000000-c9f12dbc22ea5656f07c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-ITFT , positive-QTOFsplash10-0uxr-0190000000-7a948782b86b2057690c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-ITFT , positive-QTOFsplash10-0udi-0190000000-e8c8dc33e2d74b5af54a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-ITFT , positive-QTOFsplash10-0udi-0190000000-8bc360c878c7ddfb21352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-QTOF , positive-QTOFsplash10-014i-0090000000-d0dd8082e47d3cdf89c82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-QTOF , positive-QTOFsplash10-0udi-0390000000-b51bcbe48eab7eb99e0f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-QTOF , positive-QTOFsplash10-01b9-0900000000-187f429d7e359302ca692017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten , positive-QTOFsplash10-0udi-0950000000-b19407bde306a78efe772017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten 75V, Positive-QTOFsplash10-0fk9-0940000000-ed0fbde1052e8b0f1c182021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten 15V, Positive-QTOFsplash10-014i-0090000000-14415175bf4ef6e8bb112021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten 30V, Positive-QTOFsplash10-014i-0090000000-c2bae143550125771dd52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten 15V, Positive-QTOFsplash10-0uxr-0090000000-5079706ec92060f274b62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten 90V, Positive-QTOFsplash10-01b9-3910000000-423ea775a61b5cb66f7c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten 50V, Positive-QTOFsplash10-00dj-0900000000-54e8728fd97629535c762021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten 45V, Positive-QTOFsplash10-0uxr-0090000000-f2a40783e7a2f31ee25e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergapten 10V, Positive-QTOFsplash10-014i-0090000000-af65171e5fbd0d0f2f8d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergapten 20V, Positive-QTOFsplash10-014i-0190000000-f11609a8b07550b0255d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergapten 40V, Positive-QTOFsplash10-0pic-1930000000-6fadbe89a5a3974a8f952015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergapten 10V, Negative-QTOFsplash10-014i-0190000000-7d80d6ed97043f207cf42015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergapten 20V, Negative-QTOFsplash10-014i-0590000000-1f47d1bdb75386655f1f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergapten 40V, Negative-QTOFsplash10-0a4j-0900000000-38a514b1687da9023de82015-04-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDDB12216
Phenol Explorer Compound ID717
FooDB IDFDB002542
KNApSAcK IDC00000575
Chemspider ID2265
KEGG Compound IDC01557
BioCyc ID5-METHOXYFURANOCOUMARIN
BiGG IDNot Available
Wikipedia LinkBergapten
METLIN IDNot Available
PubChem Compound2355
PDB IDNot Available
ChEBI ID18293
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1012251
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:21273683 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .