ContaminantDB: 6,7-Dihydroxybergamottin

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 21:35:56 UTC

Update Date

2016-11-09 01:08:21 UTC

Accession Number

CHEM000736

Identification

Common Name

6,7-Dihydroxybergamottin

Class

Small Molecule

Description

6,7-Dihydroxybergamottin is a furocoumarin. Furocoumarins, are phototoxic and photocarcinogenic. They intercalate DNA and photochemically induce mutations. Furocoumarins are botanical phytoalexins found to varying extents in a variety of vegetables and fruits, notably citrus fruits. The levels of furocoumarins present in our diets, while normally well below that causing evident acute phototoxicity, do cause pharmacologically relevant drug interactions. Some are particularly active against cytochrome P450s. For example, in humans, bergamottin and dihydroxybergamottin are responsible for the 'grapefruit juice effect', in which these furanocoumarins affect the metabolism of certain drugs.

Contaminant Sources

T3DB toxins

Contaminant Type

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

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₃H₂₈O₅

Average Molecular Mass

384.465 g/mol

Monoisotopic Mass

384.194 g/mol

CAS Registry Number

145414-76-2

IUPAC Name

5-{[(2E)-6-hydroxy-3,7,7-trimethyloct-2-en-1-yl]oxy}-2H,8H-pyrano[3,2-g]chromen-2-one

Traditional Name

5-{[(2E)-6-hydroxy-3,7,7-trimethyloct-2-en-1-yl]oxy}-8H-pyrano[3,2-g]chromen-2-one

SMILES

C\C(CCC(O)C(C)(C)C)=C/COC1=C2C=CC(=O)OC2=CC2=C1C=CCO2

InChI Identifier

InChI=1S/C23H28O5/c1-15(7-9-20(24)23(2,3)4)11-13-27-22-16-6-5-12-26-18(16)14-19-17(22)8-10-21(25)28-19/h5-6,8,10-11,14,20,24H,7,9,12-13H2,1-4H3/b15-11+

InChI Key

VDZZXXJFQJNSPL-RVDMUPIBSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Linear pyranocoumarins

Alternative Parents

Substituents

Linear pyranocoumarin
Pyranochromene
1-benzopyran
Benzopyran
Fatty alcohol
Pyranone
Alkyl aryl ether
Fatty acyl
Benzenoid
Pyran
Heteroaromatic compound
Secondary alcohol
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.002 g/L	ALOGPS
logP	4.77	ALOGPS
logP	4.32	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	19.47	ChemAxon
pKa (Strongest Basic)	-0.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	111.41 m³·mol⁻¹	ChemAxon
Polarizability	42.81 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	splash10-014r-0219000000-1498ef8db3d2db7bc9e6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0673-3629000000-d0583d110a54a732909b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05n0-9221000000-2869fdf5a2de7a8b7104	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00lr-0029000000-6b9e77345783f4987185	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0495000000-f69cb3867e6cc8632564	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00y1-0910000000-b2ca85b9fc6d28fd1cb1	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

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). 6,7-Dihydroxybergamottin also acts as a CYP3A4 inhibitor (1).

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

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

71684593

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

6,7-Dihydroxybergamottin (CHEM000736)

Structure for CHEM000736: 6,7-Dihydroxybergamottin