Record Information
Version1.0
Creation date2010-04-08 22:05:25 UTC
Update date2025-11-18 22:38:12 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
Synonyms
SynonymSource
4-Methoxy-7H-furo[3,2-g][1]benzopyran-7-oneChEBI
5-MethoxyfuranocoumarinChEBI
5-MethoxypsoraleneChEBI
BergapteneChEBI
HeraclinChEBI
MajudinChEBI
O-MethylbergaptolChEBI
5-MethoxypsoralenKegg
PentadermKegg
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, MeSH
5-Methoxy-6,7-furanocoumarinHMDB
5-Methoxypsoralen (obsol.)HMDB
5-MOPHMDB
6-Hydroxy-4-methoxy-5-benzofuranacrylic acid, gamma-lactoneHMDB
BergaptanHMDB
PsoradermHMDB
BergaptenChEBI
5 MethoxypsoralenMeSH
5 Methoxy psoralenMeSH
4-Methoxyfuro[3,2-g]benzopyrane-7-onebiospider
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
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 IDBergapten
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-aggregantAn agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots.DUKE
Anti-apertif52217 An agent that suppresses appetite, reducing hunger and increasing feelings of fullness. Its biological role involves regulating hunger hormones, and it has therapeutic applications in managing obesity, weight loss, and related metabolic disorders, with key medical uses including treatment of hyperphagia and Prader-Willi syndrome.DUKE
Anti convulsant52217 An agent that reduces or prevents seizures, commonly used in managing epilepsy, neuropathic pain, and mood disorders, by stabilizing abnormal electrical activity in the brain.DUKE
Anti histaminic37956 An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti jet-lag52217 An agent that regulates the body's internal clock, reducing symptoms of jet lag, such as fatigue and insomnia, by synchronizing the circadian rhythm with new time zones, commonly used by travelers crossing multiple time zones.DUKE
Anti leukodermicAn agent that treats leucoderma (vitiligo), characterized by white skin patches or total loss of pigmentation, promoting skin repigmentation and reducing disease progression, commonly used in dermatology to manage vitiligo and other skin pigmentation disorders.DUKE
Anti mitoticAn agent that inhibits mitosis, or cell division, playing a crucial role in regulating cell growth. Therapeutically, it is used to treat cancer by blocking tumor cell proliferation. Key medical uses include chemotherapy for various cancers, such as breast, lung, and colon cancer, to prevent cancer cell division and growth.DUKE
Anti-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.DUKE
Anti plateletAn agent that prevents blood clot formation by inhibiting platelet aggregation, used to treat and prevent heart disease, stroke, and other cardiovascular conditions.DUKE
Anti-psoriac52217 An agent that reduces psoriasis symptoms, commonly used in managing plaque psoriasis, scalp psoriasis, and other inflammatory skin conditions, by inhibiting cell growth, reducing inflammation, and modulating the immune system.DUKE
Anti-spasmodic52217 An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Anti-vitiligicAn agent that prevents loss of skin pigmentation, characteristic of vitiligo, promoting melanocyte preservation and repigmentation, used therapeutically to manage vitiligo and other hypopigmentation disorders.DUKE
Calcium antagonist48706 A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
Carcinogenic50903 An agent that causes cancer, damaging cellular DNA and disrupting normal cell growth. It has no therapeutic applications, but understanding its biological role informs cancer prevention and treatment strategies, with key medical uses in oncology research and risk assessment.DUKE
ClastogenicAn agent inducing chromosomal breakages, leading to genetic mutations and rearrangements, with potential therapeutic applications in cancer treatment and research, and medical uses in genetic toxicology and mutagenesis studies.DUKE
Central nervous system depressant35470 An agent that slows brain activity, reducing anxiety, stress, and excitability. Therapeutically, it's used to manage insomnia, seizures, and anxiety disorders, promoting relaxation and sedation. Key medical uses include treating insomnia, epilepsy, and panic disorders, as well as inducing anesthesia.DUKE
Diabetic-macular-edema inhibitor35222 An agent that reduces fluid accumulation in the macula, alleviating vision impairment in diabetic patients. It blocks vascular endothelial growth factor (VEGF) activity, decreasing inflammation and edema, commonly used to treat diabetic macular edema and other retinal disorders.DUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
Insecticide24852 An agent that kills or repels insects, used to control pests and prevent disease transmission. Therapeutically, insecticides have applications in public health and veterinary medicine, key medical uses include controlling insect-borne diseases such as malaria, typhus, and Lyme disease.DUKE
LipolyticAn agent that stimulates hydrolysis of fats into fatty acids and glycerol, playing a key biological role in fat metabolism. Therapeutically, lipolytics have applications in managing obesity and hypertriglyceridemia, with medical uses including weight loss and improving lipid profiles.DUKE
MelaninogenicAn agent that stimulates melanin production, determining skin and hair color. It has therapeutic applications in treating hypopigmentation disorders, such as vitiligo, and key medical uses include skin pigmentation and protection against UV radiation.DUKE
MelatoninogenicAn agent that stimulates melatonin production, regulating sleep-wake cycles. It has therapeutic applications in managing sleep disorders, jet lag, and insomnia, and is also used to alleviate anxiety and depression symptoms.DUKE
Molluscicide33904 An agent that kills mollusks, particularly snails and slugs, playing a key role in controlling vectors of parasitic diseases. Therapeutically, it is used to prevent the spread of schistosomiasis and other snail-borne diseases, with medical applications in public health and epidemiology.DUKE
MutagenicAn agent that induces genetic mutations, altering DNA sequences. It plays a biological role in evolution and adaptation. Therapeutically, mutagenic agents are used in cancer treatment, such as chemotherapy, and in gene therapy to introduce beneficial traits. Key medical uses include oncology and genetic research.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
PhotodermatitigenicAn agent that, when activated by light, triggers an allergic response, causing a rash or systemic effects, used to study skin sensitivity and photosensitivity disorders, with applications in dermatology and allergy testing.DUKE
PhototoxicAn agent that causes skin damage, such as sunburn or blisters, upon exposure to light, especially ultraviolet light, with no therapeutic applications but key medical uses in diagnosing photosensitivity disorders.DUKE
PiscicideA substance poisonous to fish, used to eliminate dominant or invasive fish species, and combat parasitic fish, allowing for population control and management of aquatic ecosystems.DUKE
Hepatoprotective62868 An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.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.