ContaminantDB: Bergamottin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-06-08 18:13:20 UTC

Update Date

2026-04-06 10:54:39 UTC

Accession Number

CHEM000733

Identification

Common Name

Bergamottin

Class

Small Molecule

Description

Bergamottin is found in citrus. Bergamottin is a constituent of bergamot oil. Also from lemon oil and oils of other Citrus species and carrot (Daucus carota) Bergamottin is a natural furanocoumarin found principally in grapefruit juice. It is also found in the oil of bergamot, from which it was first isolated and from which its name is derived. To a lesser extent, bergamottin is also present in the essential oils of other citrus fruits. Along with the chemically related compound 6 ,7 -dihydroxybergamottin, it is believed to be responsible for the grapefruit juice effect in which the consumption of the juice affects the metabolism of a variety of pharmaceutical drugs. Bergamottin has been shown to exhibit anti-tumor function (1).

Contaminant Sources

FooDB Chemicals
T3DB toxins

Contaminant Type

Aromatic Hydrocarbon
Ester
Ether
Food Toxin
Furocoumarin
Metabolite
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Bergomottin	ChEMBL
5-Geranoxypsoralen	MeSH
8-Geranyloxypsoralen	MeSH

Chemical Formula

C₂₁H₂₂O₄

Average Molecular Mass

338.397 g/mol

Monoisotopic Mass

338.152 g/mol

CAS Registry Number

7380-40-7

IUPAC Name

4-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one

Traditional Name

bergamottin

SMILES

[H]\C(COC1=C2C=COC2=CC2=C1C=CC(=O)O2)=C(\C)CCC=C(C)C

InChI Identifier

InChI=1S/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-16-7-8-20(22)25-19(16)13-18-17(21)10-12-23-18/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9+

InChI Key

DBMJZOMNXBSRED-OQLLNIDSSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Linear furanocoumarin
Furanocoumarin
Psoralen
Coumarin
Benzopyran
1-benzopyran
Monoterpenoid
Aromatic monoterpenoid
Benzofuran
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Furan
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

furanocoumarin (CHEBI:70476 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	59 - 61°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.01 g/L	ALOGPS
logP	5.3	ALOGPS
logP	4.81	ChemAxon
logS	-4.5	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	6	ChemAxon
Refractivity	99.77 m³·mol⁻¹	ChemAxon
Polarizability	37.74 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1449000000-f1cb80e88623323efd78	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-7974000000-8dc8885c8ce63b6b8f05	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxr-9420000000-d4a732b567f78ee66d36	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0059000000-6c5381fc4c44ea7b815b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0392000000-aef5d498f581369a1495	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0910000000-f3479b11ac7337bdd5d4	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Bergamottin is a potent chemopreventive agent against aflatoxin B1-inducible cyotoxicity in H4IIE cells with a bifunctional effects on glutathione S-transferase and CYP1A. Potent inhibitor and inactivator of cytochrome P450 1A1-mediated monooxygenase in both murine hepatic microsomes and in a reconstituted system using purified human P450 1A1 (6). The mechanism of action many furocoumarins is based on their ability to form photoadducts with DNA and other cellular components such as RNA, proteins, and several proteins found in the membrane such as phospholipases A2 and C, Ca-dependent and cAMPdependent protein-kinase and epidermal growth factor. Furocoumarins intercalate between base pairs of DNA and after ultraviolet-A irradiation, giving cycloadducts. (6)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not listed by IARC. IARC has assessed other furocoumarins, classifying 8-methoxypsoralen as carcinogenic to humans (Group 1), 5-methoxypsoralen as possibly carcinogenic to humans (Group 2A), and certain other furocoumarins as not being classifiable as to their carcinogenicity to humans (Group 3). (5)

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

The furocoumarin 8-methoxypsoralen is carcinogenic to humans, and possibly 5-methoxypsoralen as well (5). There is some evidence from mouse studies that other furocoumarins are carcinogenic when combined with exposure to UVA radiation (2). The SKLM regards the additional risk of skin cancer arising from the consumption of typical quantities of furocoumarin-containing foods, which remain significantly below the range of phototoxic doses, as insignificant. However, the consumption of phototoxic quantities cannot be ruled out for certain foods, particularly celery and parsnips, that may lead to significant increases in furocoumarin concentrations, depending on the storage, processing and production conditions. (7) Furocoumarin photochemotherapy is known to induce a number of side-effects including erythema, edema, hyperpigmentation, and premature aging of skin. All photobiological effects of furocoumarins result from their photochemical reactions. Because many dietary or water soluble furocoumarins are strong inhibitors of cytochrome P450s, they will also cause adverse drug reactions when taken with other drugs.

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Bergamottin

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

5471349

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Bergamottin (CHEM000733)

Structure for CHEM000733: Bergamottin