Showing Compound Axillarin (FDB002414)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:22 UTC

Update date

2025-11-18 22:37:18 UTC

Primary ID

FDB002414

Secondary Accession Numbers

FDB005976

Chemical Information

FooDB Name

Axillarin

Description

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.

CAS Number

5188-73-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3',4',5,7-Tetrahydroxy-3,6-dimethoxyflavone	ChEBI
3,6-Dimethoxyquercetagetin	ChEBI
Quercetagetin 3,6-dimethyl ether	ChEBI
DMQT	MeSH
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3,6-dimethoxy-4H-1-benzopyran-4-one, 9CI	db_source
Axillarin	db_source

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

Chemical Formula

C17H14O8

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

346.2883

Monoisotopic Molecular Weight

346.068867424

Classification

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 )

Ontology

Disposition

Source:

Endogenous

Biological:

Plant

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 58.96%; H 4.07%; O 36.96%	DFC
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	369 (e 17800) (EtOH/NaOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Axillarin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-044j-1143195000-ef6e852b0fb445b85f27	Spectrum
Predicted GC-MS	Axillarin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-0439000000-ac8c8e40c24b0ad21627	Spectrum
Predicted GC-MS	Axillarin, non-derivatized, 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	splash10-0002-0009000000-931bc81dc6845ae8bdb0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0109000000-ea22d6d990c5fcd68157	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ar0-4922000000-60666c5d32df8f444ba7	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-7ba67991d6c4bb1b57fc	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0029000000-fb517d3332ab3b037f6c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-4941000000-fce546a0c270c82fc38f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-ec61fcb5ea3f5c984d69	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0419000000-37136757256ca6a2b424	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01c0-1921000000-2ac43aecd3dfed3082e0	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0009000000-24b80c82c41a998b9ea5	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0009000000-6bb94117a9648af67e8c	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ls-1914000000-844cac53e0c6a48fb19b	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

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

CLR22-H:CLR22-H

EAFUS ID

Not Available

Dr. Duke ID

AXILLARIN

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

Axillarin

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-inflammatory	35472	An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.	DUKE
Anti-rhinoviral	22587	An agent that inhibits the replication of rhinoviruses, reducing symptoms of the common cold. Therapeutically, it is used to treat and prevent rhinoviral infections, commonly used in managing respiratory illnesses such as bronchiolitis and asthma exacerbations.	DUKE
Anti-viral	22587	An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.	DUKE
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE