Showing Compound Fraxidin (FDB012577)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:15 UTC

Update date

2020-02-24 19:11:08 UTC

Primary ID

FDB012577

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Fraxidin

Description

Fraxidin, also known as 8-hydroxy-6,7-dimethoxy-2h-1-benzopyran-2-one, is a member of the class of compounds known as hydroxycoumarins. Hydroxycoumarins are coumarins that contain one or more hydroxyl groups attached to the coumarin skeleton. Fraxidin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Fraxidin can be found in durian and watermelon, which makes fraxidin a potential biomarker for the consumption of these food products.

CAS Number

525-21-3

Structure

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

Synonyms

Synonym	Source
8-Hydroxy-6,7-dimethoxy-2H-1-benzopyran-2-one	Kegg
Fraxiden	MeSH
2H-1-Benzopyran-2-one, 8-hydroxy-6,7-dimethoxy-	biospider
8-Hydroxy-6,7-dimethoxy-2-benzopyrone	biospider
8-Hydroxy-6,7-dimethoxycoumarin	db_source
Fraxidin	db_source

Predicted Properties

Property	Value	Source
Water Solubility	1.58 g/L	ALOGPS
logP	1.83	ALOGPS
logP	1.81	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	10.73	ChemAxon
pKa (Strongest Basic)	-3.3	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	2	ChemAxon
Refractivity	56.46 m³·mol⁻¹	ChemAxon
Polarizability	21.2 Å³	ChemAxon
Number of Rings	2	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

C11H10O5

IUPAC name

8-hydroxy-6,7-dimethoxy-2H-chromen-2-one

InChI Identifier

InChI=1S/C11H10O5/c1-14-7-5-6-3-4-8(12)16-10(6)9(13)11(7)15-2/h3-5,13H,1-2H3

InChI Key

QNFBKOHHLAWWTC-UHFFFAOYSA-N

Isomeric SMILES

COC1=C(OC)C(O)=C2OC(=O)C=CC2=C1

Average Molecular Weight

222.1941

Monoisotopic Molecular Weight

222.05282343

Classification

Description

Belongs to the class of organic compounds known as hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

Hydroxycoumarins

Alternative Parents

Substituents

Hydroxycoumarin
Benzopyran
1-benzopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxycoumarin (CHEBI:81120 )

Ontology

Disposition

Source:

Endogenous

Biological:

Plant

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 59.46%; H 4.54%; O 36.00%	DFC
Melting Point	Mp 196-197°	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	Fraxidin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fmi-1090000000-57a4b8a1ffc02d3ff38c	Spectrum
Predicted GC-MS	Fraxidin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-0920000000-0789ab666a899a6ee191	Spectrum
Predicted GC-MS	Fraxidin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-d072371fa1a0d12b8a30	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0190000000-6a957c893a8bc14e1b83	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06tf-1920000000-4e0154f5381d381b3766	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0290000000-130b68560aefb7723b5f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0490000000-12c022694af4770c20c8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052e-3900000000-7b9037a7fee819198824	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-b3900c5041b4d10c4c65	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0290000000-668671f6655792921d73	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000b-3900000000-e8ea2de535bfedabeb30	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-cf583f8087451ddaae0f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0190000000-684c8c34647b0cdb11a3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-2900000000-c927504b30b3573647e4	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C17479

Pubchem Compound ID

3083616

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

BFQ13-Z:HJC23-A

EAFUS ID

Not Available

Dr. Duke ID

FRAXIDIN

BIGG ID

Not Available

KNApSAcK ID

C00019875

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 Fraxidin (FDB012577)

Structure for FDB012577 (Fraxidin)