ContaminantDB: Eupafolin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 21:46:28 UTC

Update Date

2016-11-09 01:17:54 UTC

Accession Number

CHEM024543

Identification

Common Name

Eupafolin

Class

Small Molecule

Description

Eupafolin, also known as 6-methoxy 5 or 73'4'-tetrahydroxyflavone, is a member of the class of compounds known as 6-o-methylated flavonoids. 6-o-methylated flavonoids are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, eupafolin is considered to be a flavonoid lipid molecule. Eupafolin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Eupafolin can be found in common sage, lemon verbena, rosemary, and sesame, which makes eupafolin a potential biomarker for the consumption of these food products.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

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

Synonyms

Value	Source
Nepetin	MeSH
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one	MeSH
6-Methoxy 5	ChEMBL
73'4'-Tetrahydroxyflavone	ChEMBL
6-Methoxyluteolin	ChEMBL
Pedaltin	ChEMBL

Chemical Formula

C₁₆H₁₂O₇

Average Molecular Mass

316.262 g/mol

Monoisotopic Mass

316.058 g/mol

CAS Registry Number

520-11-6

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one

Traditional Name

nepetin

SMILES

COC1=C(O)C2=C(OC(=CC2=O)C2=CC=C(O)C(O)=C2)C=C1O

InChI Identifier

InChI=1S/C16H12O7/c1-22-16-11(20)6-13-14(15(16)21)10(19)5-12(23-13)7-2-3-8(17)9(18)4-7/h2-6,17-18,20-21H,1H3

InChI Key

FHHSEFRSDKWJKJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

6-O-methylated flavonoids

Alternative Parents

Substituents

6-methoxyflavonoid-skeleton
7-hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Anisole
Catechol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Benzenoid
Pyran
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111230 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

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

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	2.75	ALOGPS
logP	2.25	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.09	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.36 m³·mol⁻¹	ChemAxon
Polarizability	30.8 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	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ks-0593000000-d04df03ef923f105cbb2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-0ug0-0792000000-b0493b07c4cff8abe96d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0ug0-0792000000-b0493b07c4cff8abe96d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0ug0-0792000000-b0493b07c4cff8abe96d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-001r-0940000000-5baa8bd5a625567f08dd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 22V, positive	splash10-0udi-0009000000-f37db28495a264cf9503	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT 22V, positive	splash10-0udi-0009000000-6cb654a8d44da14a1c4b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0029000000-48a42a678280a96feb08	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0169000000-c3695b331b8399faf052	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4m-3960000000-b179e1b189656ec5854b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-d1eea835c66835196377	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0169000000-5a4afa1d2dc63c754c00	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-5950000000-10104b78aa48595ecdf7	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0150804

FooDB ID

FDB002422

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

5317284

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

Eupafolin (CHEM024543)

Structure for CHEM024543: Eupafolin