AFCDB: Bergapten (FDB002542)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:25 UTC

Update date

2019-11-26 02:57:35 UTC

Primary ID

FDB002542

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Bergapten

Description

Bergapten, 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 (Pimpinella anisum), figs (Ficus carica), and parsnips (Pastinaca sativa) and in a lower concentration in grapefruits (Citrus X paradisi), carrots (Daucus carota ssp. sativus), and fennels (Foeniculum vulgare). Bergapten has also been detected, but not quantified in, several different foods, such as spelts (Triticum spelta), mountain yams (Dioscorea pentaphylla), strawberry guavas (Psidium cattleianum), common buckwheats (Fagopyrum esculentum), and passion fruits (Passiflora edulis). This could make bergapten a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Bergapten.

CAS Number

484-20-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C12H8O4

IUPAC name

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

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

Isomeric SMILES

COC1=C2C=CC(=O)OC2=CC2=C1C=CO2

Average Molecular Weight

216.192

Monoisotopic Molecular Weight

216.042258738

Classification

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Animal

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Pharmaceutical industry:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 66.67%; H 3.73%; O 29.60%	DFC
Melting Point	Mp 188°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-01b9-7950000000-e77dc647c2fa0ccbb177	2014-09-20	View Spectrum
GC-MS	Bergapten, non-derivatized, GC-MS Spectrum	splash10-01b9-3890000000-a8341e87fa6830843ef7	Spectrum
GC-MS	Bergapten, non-derivatized, GC-MS Spectrum	splash10-00y1-3940000000-1492cacf3f4395e9f66c	Spectrum
GC-MS	Bergapten, non-derivatized, GC-MS Spectrum	splash10-01b9-3890000000-a8341e87fa6830843ef7	Spectrum
GC-MS	Bergapten, non-derivatized, GC-MS Spectrum	splash10-00y1-3940000000-1492cacf3f4395e9f66c	Spectrum
Predicted GC-MS	Bergapten, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-1920000000-1f376a338d3e06136886	Spectrum
Predicted GC-MS	Bergapten, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0udi-0950000000-b19407bde306a78efe77	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0090000000-927b1385246a4f40d60d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0uxr-0090000000-53c9077581fc1617f789	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0290000000-d6eb013ef1071457a5b1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0gb9-0090000000-c9f12dbc22ea5656f07c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0uxr-0190000000-7a948782b86b2057690c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0190000000-e8c8dc33e2d74b5af54a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0190000000-8bc360c878c7ddfb2135	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0090000000-d0dd8082e47d3cdf89c8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0390000000-b51bcbe48eab7eb99e0f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-01b9-0900000000-187f429d7e359302ca69	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0udi-0950000000-b19407bde306a78efe77	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0fk9-0940000000-ed0fbde1052e8b0f1c18	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-014i-0090000000-14415175bf4ef6e8bb11	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0090000000-c2bae143550125771dd5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0uxr-0090000000-5079706ec92060f274b6	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-01b9-3910000000-423ea775a61b5cb66f7c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-00dj-0900000000-54e8728fd97629535c76	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0uxr-0090000000-f2a40783e7a2f31ee25e	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0090000000-af65171e5fbd0d0f2f8d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0190000000-f11609a8b07550b0255d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pic-1930000000-6fadbe89a5a3974a8f95	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0190000000-7d80d6ed97043f207cf4	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0590000000-1f47d1bdb75386655f1f	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4j-0900000000-38a514b1687da9023de8	2015-04-25	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

18293

Phenol-Explorer ID

717

DrugBank ID

Not Available

HMDB ID

HMDB30637

CRC / DFC (Dictionary of Food Compounds) ID

CMH82-I:CMH78-L

EAFUS ID

Not Available

Dr. Duke ID

BERGAPTEN|TRANS-BETA-BERGAPTENE|5-METHOXY-PSORALEN

BIGG ID

Not Available

KNApSAcK ID

C00000575

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Carrot	0.03000 - 17.00000	8.515	DUKE
Dill	Expected but not quantified	Not Available	DUKE
Parsnip	190.160 - 190.160 mg/100 g	190.160 mg/100 g	DUKE, PHYTOHUB
Barley	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Broccoli	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Common pea	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Cucumber	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Eggplant	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Garden onion	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Garden tomato	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis

Showing 1 to 10 of 37 entries

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
anti aggregant			DUKE
anti apertif	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti convulsant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti histaminic	37956	Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti jet-lag	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti leukodermic			DUKE
anti mitotic			DUKE
anti mutagenic			DUKE
anti platelet			DUKE

Showing 1 to 10 of 33 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.

Bergapten (FDB002542)

Structure for FDB002542 (Bergapten)