Showing Compound Bergaptol (FDB002543)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:25 UTC

Update date

2019-11-26 02:57:35 UTC

Primary ID

FDB002543

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Bergaptol

Description

Bergaptol, also known as 5-hydroxypsoralen, belongs to the class of organic compounds known as 5-hydroxypsoralens. These are psoralens containing a hydroxyl group attached at the C5 position of the psoralen group. Bergaptol has been detected, but not quantified in, several different foods, such as tamarinds (Tamarindus indica), parsnips (Pastinaca sativa), bayberries (Myrica), chives (Allium schoenoprasum), and lovages (Levisticum officinale). This could make bergaptol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Bergaptol.

CAS Number

486-60-2

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
5-Hydroxyfuranocoumarin	ChEBI
5-Hydroxypsoralen	ChEBI
4-Hydroxy-7H-furo(3,2-g)chromen-7-one	MeSH
4-Hydroxy-7H-furo[3,2-g]chromen-7-one	HMDB
4-Hydroxy-7H-furo[3,2-g]chromen-7-one (acd/name 4.0)	HMDB
5-HYDROXY-psoralin	HMDB
Bergaptols	HMDB
4-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-one, 9CI	db_source
4-hydroxy-7H-furo[3,2-g]chromen-7-one	biospider
4-Hydroxypsoralen	db_source
7H-Furo(3,2-g)(1)benzopyran-7-one, 4-hydroxy- (8CI)(9CI)	biospider
7H-Furo[3,2-g][1]benzopyran-7-one, 4-hydroxy-	biospider
PSORALIN, 5-HYDROXY-	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.89 g/L	ALOGPS
logP	1.86	ALOGPS
logP	1.64	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	6.45	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.67 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	52.37 m³·mol⁻¹	ChemAxon
Polarizability	18.94 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C11H6O4

IUPAC name

4-hydroxy-7H-furo[3,2-g]chromen-7-one

InChI Identifier

InChI=1S/C11H6O4/c12-10-2-1-6-9(15-10)5-8-7(11(6)13)3-4-14-8/h1-5,13H

InChI Key

GIJHDGJRTUSBJR-UHFFFAOYSA-N

Isomeric SMILES

OC1=C2C=CC(=O)OC2=CC2=C1C=CO2

Average Molecular Weight

202.165

Monoisotopic Molecular Weight

202.026608673

Classification

Description

Belongs to the class of organic compounds known as 5-hydroxypsoralens. These are psoralens containing a hydroxyl group attached at the C5 position of the psoralen group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

5-hydroxypsoralens

Alternative Parents

Substituents

5-hydroxypsoralen
Benzopyran
1-benzopyran
Benzofuran
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Furan
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

psoralens (CHEBI:17377 )
5-hydroxyfurocoumarin (CHEBI:17377 )
Furanocoumarins (C00758 )
a coumarin (BERGAPTOL )

Ontology

Disposition

Source:

Endogenous

Biological:

Plant

Foods

Fruits and vegetables:

Fruits:

Citrus:

Grapefruit

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 65.35%; H 2.99%; O 31.66%	DFC
Melting Point	Mp 277-278°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Bergaptol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05fr-1910000000-e6a47789c6cb25ff3a46	Spectrum
Predicted GC-MS	Bergaptol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-4090000000-566be005cc2959d86652	Spectrum
Predicted GC-MS	Bergaptol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0002-0910000000-cc054eaed6fc83b4a27a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0002-0910000000-cc054eaed6fc83b4a27a	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0190000000-ac460f53d5cb80eb5044	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0490000000-b86689b17be620c214e6	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dr-1900000000-6193deca8502dc532307	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0190000000-f8c060c4143f0fd9068c	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0490000000-f83b2cbc9d5dea16671f	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053r-1900000000-6a70dde5da85af79bd84	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-6f70ceb2368baddf4f40	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090000000-6f70ceb2368baddf4f40	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-0920000000-3f79d1ece069a20ce05b	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-2e5a86e101fa40f235c9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0090000000-2e5a86e101fa40f235c9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-0910000000-3e2fa866225a62b55263	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C00758

Pubchem Compound ID

5280371

Pubchem Substance ID

Not Available

ChEBI ID

17377

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

CMH82-I:CMH82-I

EAFUS ID

Not Available

Dr. Duke ID

BERGAPTOL

BIGG ID

Not Available

KNApSAcK ID

C00000581

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not 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.

Showing Compound Bergaptol (FDB002543)

Structure for FDB002543 (Bergaptol)