Record Information
Version1.0
Creation date2010-04-08 22:05:25 UTC
Update date2018-05-29 18:26:51 UTC
Primary IDFDB002542
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBergapten
DescriptionBergapten is a major constituent of bergamot oil (Citrus bergamia). Present in celery, esp. the outer leaves, and other common grocery vegetables. Implicated in photodermatitis among grocery workers. It is also found in rose hip, sweet marjoram, greenthread tea, and tartary buckwheat.
CAS Number484-20-8
Structure
Thumb
Synonyms
SynonymSource
4-Methoxy-7H-furo[3,2-g][1]benzopyran-7-oneChEBI
5-MethoxyfuranocoumarinChEBI
5-MethoxypsoraleneChEBI
BergapteneChEBI
HeraclinChEBI
MajudinChEBI
O-MethylbergaptolChEBI
PentadermKegg
5-MethoxypsoralenKegg
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
5-Methoxy-6,7-furanocoumarinHMDB
5-Methoxypsoralen (obsol.)HMDB
5-MOPHMDB
6-Hydroxy-4-methoxy-5-benzofuranacrylic acid, gamma-lactoneHMDB
BergaptanHMDB
PsoradermHMDB
BergaptenChEBI
7H-Furo(3,2-g)(1)benzopyran-7-one, 4-methoxy-biospider
7H-Furo[3,2-g][1]benzopyran-7-one, 4-methoxy-biospider
O-methylbergaptolbiospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Physico-Chemical Properties - Experimental
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01b9-3890000000-a8341e87fa6830843ef7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00y1-3940000000-1492cacf3f4395e9f66cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01b9-3890000000-a8341e87fa6830843ef7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00y1-3940000000-1492cacf3f4395e9f66cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1920000000-1f376a338d3e06136886View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-0950000000-b19407bde306a78efe77View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0090000000-927b1385246a4f40d60dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0uxr-0090000000-53c9077581fc1617f789View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0290000000-d6eb013ef1071457a5b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0gb9-0090000000-c9f12dbc22ea5656f07cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0uxr-0190000000-7a948782b86b2057690cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0190000000-e8c8dc33e2d74b5af54aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0190000000-8bc360c878c7ddfb2135View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0090000000-d0dd8082e47d3cdf89c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0390000000-b51bcbe48eab7eb99e0fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01b9-0900000000-187f429d7e359302ca69View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0950000000-b19407bde306a78efe77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-af65171e5fbd0d0f2f8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0190000000-f11609a8b07550b0255dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pic-1930000000-6fadbe89a5a3974a8f95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0190000000-7d80d6ed97043f207cf4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0590000000-1f47d1bdb75386655f1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-0900000000-38a514b1687da9023de8View in MoNA
MSMass Spectrum (Electron Ionization)splash10-01b9-7950000000-e77dc647c2fa0ccbb177View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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
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.