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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:06 UTC
Update Date2021-09-07 17:05:29 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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point188 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available148.66431661259
DarkChem[M-H]-PredictedNot Available148.08731661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01b9-3890000000-a8341e87fa6830843ef72017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00y1-3940000000-1492cacf3f4395e9f66c2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01b9-3890000000-a8341e87fa6830843ef72018-05-18View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00y1-3940000000-1492cacf3f4395e9f66c2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1920000000-1f376a338d3e061368862017-07-27View Spectrum
MSMass Spectrum (Electron Ionization)splash10-01b9-7950000000-e77dc647c2fa0ccbb1772014-09-20View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-0950000000-b19407bde306a78efe772017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0090000000-927b1385246a4f40d60d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0uxr-0090000000-53c9077581fc1617f7892017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0290000000-d6eb013ef1071457a5b12017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0gb9-0090000000-c9f12dbc22ea5656f07c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0uxr-0190000000-7a948782b86b2057690c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0190000000-e8c8dc33e2d74b5af54a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0190000000-8bc360c878c7ddfb21352017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0090000000-d0dd8082e47d3cdf89c82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0390000000-b51bcbe48eab7eb99e0f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01b9-0900000000-187f429d7e359302ca692017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0950000000-b19407bde306a78efe772017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0fk9-0940000000-ed0fbde1052e8b0f1c182021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-014i-0090000000-14415175bf4ef6e8bb112021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-af65171e5fbd0d0f2f8d2015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0190000000-f11609a8b07550b0255d2015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pic-1930000000-6fadbe89a5a3974a8f952015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0190000000-7d80d6ed97043f207cf42015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0590000000-1f47d1bdb75386655f1f2015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-0900000000-38a514b1687da9023de82015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-f3b1b7cd2b3d93168c5f2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0910000000-b87dfd372f7638b20dfe2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-7891ec2b2bad4a52dc5c2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0980000000-f4756448f6e7831acbf52021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-f3b1b7cd2b3d93168c5f2021-09-09View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)2014-09-20View Spectrum
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
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.. .