Showing Compound Cirsiliol (FDB016700)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:35 UTC

Update date

2019-11-26 03:13:38 UTC

Primary ID

FDB016700

Secondary Accession Numbers

FDB006924

Chemical Information

FooDB Name

Cirsiliol

Description

Cirsiliol, also known as 3',4',5-trihydroxy-6,7-dimethoxyflavone or 6,7-dimethoxy-5,3',4'-trihydroxyflavone, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, cirsiliol is considered to be a flavonoid lipid molecule. Cirsiliol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cirsiliol can be found in common sage and lemon verbena, which makes cirsiliol a potential biomarker for the consumption of these food products.

CAS Number

34334-69-5

Structure

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

Synonyms

Synonym	Source
3',4',5-Trihydroxy-6,7-dimethoxyflavone	ChEBI
6,7-Dimethoxy-5,3',4'-trihydroxyflavone	ChEBI
3',4',5-Trihydroxy-6,7-dimethoxy-flavone	MeSH
Cirsiliol	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.062 g/L	ALOGPS
logP	3.05	ALOGPS
logP	2.39	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.57	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	85.84 m³·mol⁻¹	ChemAxon
Polarizability	32.84 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

C17H14O7

IUPAC name

2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one

InChI Identifier

InChI=1S/C17H14O7/c1-22-14-7-13-15(16(21)17(14)23-2)11(20)6-12(24-13)8-3-4-9(18)10(19)5-8/h3-7,18-19,21H,1-2H3

InChI Key

IMEYGBIXGJLUIS-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC2=C(C(=O)C=C(O2)C2=CC(O)=C(O)C=C2)C(O)=C1OC

Average Molecular Weight

330.2889

Monoisotopic Molecular Weight

330.073952802

Classification

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

7-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
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

trihydroxyflavone (CHEBI:3719 )
dimethoxyflavone (CHEBI:3719 )
flavones (C10033 )
Flavones and Flavonols (C10033 )
Flavones and Flavonols (LMPK12111227 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 61.82%; H 4.27%; O 33.91%	DFC
Melting Point	Mp 285-287° (280°)	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	348 () (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Cirsilion, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0w29-0529000000-657bcbdce3c33c05fa19	Spectrum
Predicted GC-MS	Cirsilion, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsilion, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsilion, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsilion, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsilion, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsilion, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsilion, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsilion, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsilion, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsilion, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsilion, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsilion, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsilion, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsilion, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsilion, TBDMS_3_1, 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	splash10-001i-0009000000-6fdb0b39524682572668	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0029000000-e2443fa738a37a6c94c8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-2591000000-273c2d09d171c9c377a9	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-180fc64ac4527a869911	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0039000000-e18384ff2ececeea4c40	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-7591000000-cff288ef73ebd280eb74	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0009000000-6e7c1f722f7f2751ab68	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0009000000-974e87f7b29a2112831c	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0294000000-8a78f0a808bb3fa6abe8	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-3ed9b5835e6e53d95cde	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ti-0049000000-97f6ef43a008bb11d3f9	2021-10-12	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C10033

Pubchem Compound ID

160237

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

KDD85-Q:KSN13-S

EAFUS ID

Not Available

Dr. Duke ID

CIRSILIOL

BIGG ID

Not Available

KNApSAcK ID

C00001033

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 agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.	DUKE
Anti leukotriene	35222	An agent that blocks the action of leukotrienes, reducing inflammation and bronchoconstriction. Therapeutically, it is used to treat asthma, allergic rhinitis, and other respiratory disorders by inhibiting the biological role of leukotrienes in mediating inflammatory responses.	DUKE
Lipoxygenase inhibitor	35856	An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases.	DUKE