ChemFOnt: Showing chemical card for Axillarin (CFc000333084)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:12:50 UTC

Chemfont ID

CFc000333084

Molecule Identification

Common Name

Axillarin

Definition

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,6-dimethoxy-4h-chromen-4-one, also known as 3',4',5,7-tetrahydroxy-3,6-dimethoxyflavone or 3,6-dimethoxyquercetagetin, is a member of the class of compounds known as 6-o-methylated flavonoids. 6-o-methylated flavonoids are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,6-dimethoxy-4h-chromen-4-one is considered to be a flavonoid lipid molecule. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,6-dimethoxy-4h-chromen-4-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,6-dimethoxy-4h-chromen-4-one can be found in german camomile, which makes 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,6-dimethoxy-4h-chromen-4-one a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3',4',5,7-Tetrahydroxy-3,6-dimethoxyflavone	ChEBI
3,6-Dimethoxyquercetagetin	ChEBI
Quercetagetin 3,6-dimethyl ether	ChEBI
DMQT	MeSH

Chemical Formula

C₁₇H₁₄O₈

Average Molecular Weight

346.2883

Monoisotopic Molecular Weight

346.068867424

IUPAC Name

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

Traditional Name

axillarin

CAS Registry Number

5188-73-8

SMILES

COC1=C(O)C2=C(OC(=C(OC)C2=O)C2=CC(O)=C(O)C=C2)C=C1O

InChI Identifier

InChI=1S/C17H14O8/c1-23-16-10(20)6-11-12(13(16)21)14(22)17(24-2)15(25-11)7-3-4-8(18)9(19)5-7/h3-6,18-21H,1-2H3

InChI Key

KIGVXRGRNLQNNI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

6-O-methylated flavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydroxyflavone (CHEBI:2941 )
dimethoxyflavone (CHEBI:2941 )
flavonols (C10021 )
Flavones and Flavonols (C10021 )
Flavones and Flavonols (LMPK12112990 )

Functional Ontology

Not Available

Endogenous (FooDB: )

Plant

Plant (FooDB: )

German camomile (FooDB: FOOD00107)

Not Available

EC 1.1.1.21 (aldehyde reductase) inhibitor (FooDB: )

Anti-inflammatory (FooDB: )
Anti rhinoviral (FooDB: )

Industrial application

Antiviral agent (FooDB: )

Pharmaceutical industry

Antineoplastic agent

Cancer preventive (FooDB: )

Agriculture

Pesticide (FooDB: )

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	2.66	ALOGPS
logP	2.11	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	6.9	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	88.08 m³·mol⁻¹	ChemAxon
Polarizability	33.54 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