ChemFOnt: Showing chemical card for Cirsilineol (CFc000283128)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:36:06 UTC

Chemfont ID

CFc000283128

Molecule Identification

Common Name

Cirsilineol

Definition

Cirsilineol, also known as 4',5-dihydroxy-3',6,7-trimethoxy-flavone or anisomelin, 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, cirsilineol is considered to be a flavonoid lipid molecule. Cirsilineol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cirsilineol can be found in a number of food items such as common thyme, tarragon, common sage, and hyssop, which makes cirsilineol a potential biomarker for the consumption of these food products. Cirsilineol is a bioactive flavone isolated from Artemisia and from Teucrium gnaphalodes .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Anisomelin	MetaCyc
5,4'-Dihydroxy-6,7,3'-trimethoxyflavone	MetaCyc
Eupatrin	MetaCyc
Fastigenin	MetaCyc
5-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one	MetaCyc
4',5-Dihydroxy-3',6,7-trimethoxyflavone	MeSH
4',5-Dihydroxy-3',6,7-trimethoxy-flavone	MeSH

Chemical Formula

C₁₈H₁₆O₇

Average Molecular Weight

344.3154

Monoisotopic Molecular Weight

344.089602866

IUPAC Name

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

Traditional Name

cirsilineol

CAS Registry Number

41365-32-6

SMILES

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

InChI Identifier

InChI=1S/C18H16O7/c1-22-13-6-9(4-5-10(13)19)12-7-11(20)16-14(25-12)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3

InChI Key

VKOSQMWSWLZQPA-UHFFFAOYSA-N

Chemical Taxonomy

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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavone (CHEBI:3718 )
trimethoxyflavone (CHEBI:3718 )
flavones (C10032 )
Flavones and Flavonols (C10032 )
Flavones and Flavonols (LMPK12111249 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303612)

Not Available

EC 1.1.1.21 (aldehyde reductase) inhibitor (HMDB: HMDB0303612)
Cyclooxygenase 1 inhibitor (HMDB: HMDB0303612)
Cyclooxygenase 2 inhibitor (HMDB: HMDB0303612)

Industrial application

Pharmaceutical industry

Antineoplastic agent

Cancer preventive (HMDB: HMDB0303612)

Agriculture

Pesticide

Parasiticide (HMDB: HMDB0303612)

Pesticide (HMDB: HMDB0303612)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.048 g/L	ALOGPS
logP	2.93	ALOGPS
logP	2.54	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	8.87	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	90.32 m³·mol⁻¹	ChemAxon
Polarizability	34.94 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