ContaminantDB: 8-Methoxycirsilineol

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

Record Information

Version

1.0

Creation Date

2016-05-25 22:56:34 UTC

Update Date

2016-11-09 01:18:15 UTC

Accession Number

CHEM026357

Identification

Common Name

8-Methoxycirsilineol

Class

Small Molecule

Description

8-methoxycirsilineol, also known as 4',5-dihydroxy-3',6,7,8-tetramethoxyflavone, is a member of the class of compounds known as 8-o-methylated flavonoids. 8-o-methylated flavonoids are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, 8-methoxycirsilineol is considered to be a flavonoid lipid molecule. 8-methoxycirsilineol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 8-methoxycirsilineol can be found in common thyme and mandarin orange (clementine, tangerine), which makes 8-methoxycirsilineol 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
4',5-Dihydroxy-3',6,7,8-tetramethoxyflavone	MeSH

Chemical Formula

C₁₉H₁₈O₈

Average Molecular Mass

374.341 g/mol

Monoisotopic Mass

374.100 g/mol

CAS Registry Number

Not Available

IUPAC Name

5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7,8-trimethoxy-4H-chromen-4-one

Traditional Name

8-methoxycirsilineol

SMILES

COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2O

InChI Identifier

InChI=1S/C19H18O8/c1-23-13-7-9(5-6-10(13)20)12-8-11(21)14-15(22)17(24-2)19(26-4)18(25-3)16(14)27-12/h5-8,20,22H,1-4H3

InChI Key

UBZBPKARIHPOEC-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

8-O-methylated flavonoids

Alternative Parents

Substituents

7-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
3p-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
Flavone
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Methoxyphenol
Methoxybenzene
Anisole
Phenoxy compound
Phenol ether
Alkyl aryl ether
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Pyran
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Vinylogous acid
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 (LMPK12111475 )

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	0.049 g/L	ALOGPS
logP	2.5	ALOGPS
logP	2.38	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	8.39	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.79 m³·mol⁻¹	ChemAxon
Polarizability	37.65 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	splash10-0a4m-0119000000-4d729ed5b40be87c837e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0009000000-88eeaa041c0341fda922	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0009000000-1208521393a6520d9fe9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0249000000-5cd254dd993868fece6e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-47561a80cd759f3faddb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0009000000-9748404246f3879610a1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-0194000000-cf977e9fd970b2a297f4	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

HMDB0154068

FooDB ID

FDB007325

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

181092

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

8-Methoxycirsilineol (CHEM026357)

Structure for CHEM026357: 8-Methoxycirsilineol