ContaminantDB: Methysticin

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

Record Information

Version

1.0

Creation Date

2016-05-22 04:18:33 UTC

Update Date

2016-11-09 01:15:35 UTC

Accession Number

CHEM017399

Identification

Common Name

Methysticin

Class

Small Molecule

Description

Methysticin is one of the six major kavalactones found in the kava plant. Research suggests that methysticin and the related compound dihydromethysticin have CYP1A1 inducing effects which may be responsible for their toxicity.

Contaminant Sources

FooDB Chemicals
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

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

Synonyms

Value	Source
Methysticin, ((e)-(+-))-isomer	MeSH
(+)-Methysticin	ChEMBL
Methylsticin	ChEMBL
Methysticin	MeSH

Chemical Formula

C₁₅H₁₄O₅

Average Molecular Mass

274.272 g/mol

Monoisotopic Mass

274.084 g/mol

CAS Registry Number

495-85-2

IUPAC Name

(6R)-6-[(E)-2-(2H-1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one

Traditional Name

methysticin

SMILES

[H]\C(=C(\[H])[C@@]1([H])CC(OC)=CC(=O)O1)C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C15H14O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h2-6,8,11H,7,9H2,1H3/b4-2+/t11-/m0/s1

InChI Key

GTEXBOVBADJOQH-FWEMWIAWSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Kavalactones

Sub Class

Not Available

Direct Parent

Kavalactones

Alternative Parents

Substituents

Kavalactone
Benzodioxole
Styrene
Dihydropyranone
Pyran
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:6895 )
2-pyranones (CHEBI:6895 )
alpha-Pyrones (C09952 )

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	0.091 g/L	ALOGPS
logP	2.06	ALOGPS
logP	2.06	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	16.54	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	73.12 m³·mol⁻¹	ChemAxon
Polarizability	28.28 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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0290000000-b893e68600777a620698	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00fr-2960000000-c71a5758ea62256eed8f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00b9-4910000000-a7e33e4ceb645f930f85	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-492ca740b14ef97551d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0596-9180000000-676d0a9f6165bd752d97	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9520000000-903fb25f0486cbf0c91c	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

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

C00003005

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Methysticin

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

5281567

Kegg Compound ID

C09952

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Methysticin (CHEM017399)

Structure for CHEM017399: Methysticin