Showing Compound 8-Methoxycirsilineol (FDB007325)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:33 UTC

Update date

2019-11-26 03:01:37 UTC

Primary ID

FDB007325

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

8-Methoxycirsilineol

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.

CAS Number

Not Available

Structure

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

Synonyms

Synonym	Source
4',5-Dihydroxy-3',6,7,8-tetramethoxyflavone	MeSH

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C19H18O8

IUPAC name

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

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

Isomeric SMILES

COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C(OC)=C(OC)C(OC)=C2O1

Average Molecular Weight

374.3414

Monoisotopic Molecular Weight

374.100167552

Classification

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 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
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	8-Methoxycirsilineol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4m-0119000000-4d729ed5b40be87c837e	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0009000000-88eeaa041c0341fda922	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0009000000-1208521393a6520d9fe9	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0249000000-5cd254dd993868fece6e	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-47561a80cd759f3faddb	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0009000000-9748404246f3879610a1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-0194000000-cf977e9fd970b2a297f4	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

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

Not Available

EAFUS ID

Not Available

Dr. Duke ID

8-METHOXY-CIRSILINEOL

BIGG ID

Not Available

KNApSAcK ID

Not Available

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

Descriptor	ID	Definition	Reference
aldose reductase inhibitor	48550	An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE