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Bergapten (FDB002542)

Record Information
Version1.0
Creation date2010-04-08 22:05:25 UTC
Update date2019-11-26 02:57:35 UTC
Primary IDFDB002542
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 (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 Number484-20-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot 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
Chemical FormulaC12H8O4
IUPAC name4-methoxy-7H-furo[3,2-g]chromen-7-one
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
Isomeric SMILESCOC1=C2C=CC(=O)OC2=CC2=C1C=CO2
Average Molecular Weight216.192
Monoisotopic Molecular Weight216.042258738
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.
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 66.67%; H 3.73%; O 29.60%DFC
Melting PointMp 188°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data310 (e 9100) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-01b9-7950000000-e77dc647c2fa0ccbb1772014-09-20View Spectrum
GC-MSBergapten, non-derivatized, GC-MS Spectrumsplash10-01b9-3890000000-a8341e87fa6830843ef7Spectrum
GC-MSBergapten, non-derivatized, GC-MS Spectrumsplash10-00y1-3940000000-1492cacf3f4395e9f66cSpectrum
GC-MSBergapten, non-derivatized, GC-MS Spectrumsplash10-01b9-3890000000-a8341e87fa6830843ef7Spectrum
GC-MSBergapten, non-derivatized, GC-MS Spectrumsplash10-00y1-3940000000-1492cacf3f4395e9f66cSpectrum
Predicted GC-MSBergapten, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-1920000000-1f376a338d3e06136886Spectrum
Predicted GC-MSBergapten, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-0950000000-b19407bde306a78efe772017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0090000000-927b1385246a4f40d60d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0uxr-0090000000-53c9077581fc1617f7892017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0290000000-d6eb013ef1071457a5b12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0gb9-0090000000-c9f12dbc22ea5656f07c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0uxr-0190000000-7a948782b86b2057690c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0190000000-e8c8dc33e2d74b5af54a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0190000000-8bc360c878c7ddfb21352017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0090000000-d0dd8082e47d3cdf89c82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0390000000-b51bcbe48eab7eb99e0f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01b9-0900000000-187f429d7e359302ca692017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0950000000-b19407bde306a78efe772017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0fk9-0940000000-ed0fbde1052e8b0f1c182021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-014i-0090000000-14415175bf4ef6e8bb112021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0090000000-c2bae143550125771dd52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0uxr-0090000000-5079706ec92060f274b62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-01b9-3910000000-423ea775a61b5cb66f7c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00dj-0900000000-54e8728fd97629535c762021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0uxr-0090000000-f2a40783e7a2f31ee25e2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-af65171e5fbd0d0f2f8d2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0190000000-f11609a8b07550b0255d2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pic-1930000000-6fadbe89a5a3974a8f952015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0190000000-7d80d6ed97043f207cf42015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0590000000-1f47d1bdb75386655f1f2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-0900000000-38a514b1687da9023de82015-04-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Spectrum
ChemSpider ID2265
ChEMBL IDCHEMBL24171
KEGG Compound IDC01557
Pubchem Compound ID2355
Pubchem Substance IDNot Available
ChEBI ID18293
Phenol-Explorer ID717
DrugBank IDNot Available
HMDB IDHMDB30637
CRC / DFC (Dictionary of Food Compounds) IDCMH82-I:CMH78-L
EAFUS IDNot Available
Dr. Duke IDBERGAPTEN|TRANS-BETA-BERGAPTENE|5-METHOXY-PSORALEN
BIGG IDNot Available
KNApSAcK IDC00000575
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti aggregantDUKE
anti apertif52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti convulsant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti histaminic37956 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 inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti jet-lag52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti leukodermicDUKE
anti mitoticDUKE
anti mutagenicDUKE
anti plateletDUKE
anti psoriac52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti vitiligicDUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
clastogenicDUKE
central nervous system depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
diabetic-macular-edema inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hypotensiveDUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
lipolyticDUKE
melaninogenicDUKE
melatoninogenicDUKE
molluscicide33904 A substance used to destroy pests of the phylum Mollusca.DUKE
mutagenicDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
photodermatitigenicDUKE
phototoxicDUKE
piscicideDUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot 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.