ContaminantDB: Bergapten

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-09-11 02:06:26 UTC

Update Date

2026-04-14 18:39:24 UTC

Accession Number

CHEM003680

Identification

Common Name

Bergapten

Class

Small 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one	ChEBI
5-Methoxyfuranocoumarin	ChEBI
5-Methoxypsoralene	ChEBI
Bergaptene	ChEBI
Heraclin	ChEBI
Majudin	ChEBI
O-Methylbergaptol	ChEBI
5-Methoxypsoralen	Kegg
Pentaderm	Kegg
4-Methoxy-7H-furo(3,2-g)(1)benzopyran-7-one	HMDB
4-Methoxy-7H-furo[3,2-g]benzopyran-7-one	HMDB
4-Methoxy-7H-furo[3,2-g]chromen-7-one	HMDB
4-Methoxy-furo[3,2-g]chromen-7-one	HMDB
4-methoxyfuro[3,2-g]Benzopyrane-7-one	HMDB
5-Methoxy psoralen	HMDB, MeSH
5-Methoxy-6,7-furanocoumarin	HMDB
5-Methoxypsoralen (obsol.)	HMDB
5-MOP	HMDB
6-Hydroxy-4-methoxy-5-benzofuranacrylic acid, gamma-lactone	HMDB
Bergaptan	HMDB
Psoraderm	HMDB
Bergapten	ChEBI
5 Methoxypsoralen	MeSH
5 Methoxy psoralen	MeSH

Chemical Formula

C₁₂H₈O₄

Average Molecular Mass

216.192 g/mol

Monoisotopic Mass

216.042 g/mol

CAS Registry Number

484-20-8

IUPAC Name

4-methoxy-7H-furo[3,2-g]chromen-7-one

Traditional Name

bergapten

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 Key

BGEBZHIAGXMEMV-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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

5-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:18293 )
psoralens (CHEBI:18293 )
5-methoxyfurocoumarin (CHEBI:18293 )
Furanocoumarins (C01557 )
a coumarin (5-METHOXYFURANOCOUMARIN )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	188 °C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	2.12	ALOGPS
logP	1.78	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	48.67 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	56.85 m³·mol⁻¹	ChemAxon
Polarizability	20.87 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01b9-3890000000-a8341e87fa6830843ef7	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00y1-3940000000-1492cacf3f4395e9f66c	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01b9-3890000000-a8341e87fa6830843ef7	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00y1-3940000000-1492cacf3f4395e9f66c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-1920000000-1f376a338d3e06136886	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0udi-0950000000-b19407bde306a78efe77	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0090000000-927b1385246a4f40d60d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0uxr-0090000000-53c9077581fc1617f789	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0290000000-d6eb013ef1071457a5b1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0gb9-0090000000-c9f12dbc22ea5656f07c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0uxr-0190000000-7a948782b86b2057690c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0190000000-e8c8dc33e2d74b5af54a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0190000000-8bc360c878c7ddfb2135	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0090000000-d0dd8082e47d3cdf89c8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0390000000-b51bcbe48eab7eb99e0f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-01b9-0900000000-187f429d7e359302ca69	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0udi-0950000000-b19407bde306a78efe77	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0fk9-0940000000-ed0fbde1052e8b0f1c18	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-014i-0090000000-14415175bf4ef6e8bb11	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0090000000-c2bae143550125771dd5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0uxr-0090000000-5079706ec92060f274b6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-01b9-3910000000-423ea775a61b5cb66f7c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-00dj-0900000000-54e8728fd97629535c76	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0uxr-0090000000-f2a40783e7a2f31ee25e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0090000000-af65171e5fbd0d0f2f8d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0190000000-f11609a8b07550b0255d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pic-1930000000-6fadbe89a5a3974a8f95	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0190000000-7d80d6ed97043f207cf4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0590000000-1f47d1bdb75386655f1f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4j-0900000000-38a514b1687da9023de8	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01b9-7950000000-e77dc647c2fa0ccbb177	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum