Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:25 UTC |
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Update date | 2019-11-26 02:57:35 UTC |
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Primary ID | FDB002542 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Bergapten |
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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. |
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CAS Number | 484-20-8 |
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Structure | |
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Synonyms | Synonym | Source |
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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 | 4-Methoxyfuro[3,2-g]benzopyrane-7-one | biospider | 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-methylbergaptol | biospider |
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Predicted Properties | |
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Chemical Formula | C12H8O4 |
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IUPAC name | 4-methoxy-7H-furo[3,2-g]chromen-7-one |
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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 |
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InChI Key | BGEBZHIAGXMEMV-UHFFFAOYSA-N |
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Isomeric SMILES | COC1=C2C=CC(=O)OC2=CC2=C1C=CO2 |
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Average Molecular Weight | 216.192 |
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Monoisotopic Molecular Weight | 216.042258738 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Coumarins and derivatives |
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Sub Class | Furanocoumarins |
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Direct Parent | 5-methoxypsoralens |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 66.67%; H 3.73%; O 29.60% | DFC |
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Melting Point | Mp 188° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | 310 (e 9100) (EtOH) (Berdy) | DFC |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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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 |
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MS/MS | Type | Description | Splash Key | View |
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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 |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 2265 |
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ChEMBL ID | CHEMBL24171 |
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KEGG Compound ID | C01557 |
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Pubchem Compound ID | 2355 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 18293 |
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Phenol-Explorer ID | 717 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB30637 |
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CRC / DFC (Dictionary of Food Compounds) ID | CMH82-I:CMH78-L |
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EAFUS ID | Not Available |
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Dr. Duke ID | BERGAPTEN|TRANS-BETA-BERGAPTENE|5-METHOXY-PSORALEN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000575 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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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 | anti psoriac | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti spasmodic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti vitiligic | | | DUKE | calcium antagonist | 48706 | Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances. | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | carcinogenic | 50903 | 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 | clastogenic | | | DUKE | central nervous system depressant | 35470 | A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. | DUKE | diabetic-macular-edema inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | hypotensive | | | DUKE | insecticide | 24852 | 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 | lipolytic | | | DUKE | melaninogenic | | | DUKE | melatoninogenic | | | DUKE | molluscicide | 33904 | A substance used to destroy pests of the phylum Mollusca. | DUKE | mutagenic | | | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | photodermatitigenic | | | DUKE | phototoxic | | | DUKE | piscicide | | | DUKE | hepatoprotective | 62868 | Any compound that is able to prevent damage to the liver. | CHEBI |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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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.
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