Showing Compound Sideritiflavone (FDB017693)

Record Information

Version

1.0

Creation date

2010-04-08 22:13:15 UTC

Update date

2019-11-26 03:15:03 UTC

Primary ID

FDB017693

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Sideritiflavone

Description

Sideritiflavone 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. Thus, sideritiflavone is considered to be a flavonoid. Sideritiflavone has been detected, but not quantified in, a few different foods, such as herbs and spices, peppermints (Mentha X piperita), and spearmints (Mentha spicata). This could make sideritiflavone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Sideritiflavone.

CAS Number

70360-12-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-(3,4-Dihydroxyphenyl)-5-hydroxy-6,7,8-trimethoxy-4H-1-benzopyran-4-one	HMDB
3',4',5-Trihydroxy-6,7,8-trimethoxyflavone	HMDB
5,3',4'-Trihydroxy-6,7,8-trimethoxyflavone	HMDB
Sideritoflavone	HMDB
Sideritiflavone	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.067 g/L	ALOGPS
logP	2.65	ALOGPS
logP	2.23	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.66	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92.3 m³·mol⁻¹	ChemAxon
Polarizability	35.59 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

C18H16O8

IUPAC name

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

InChI Identifier

InChI=1S/C18H16O8/c1-23-16-14(22)13-11(21)7-12(8-4-5-9(19)10(20)6-8)26-15(13)17(24-2)18(16)25-3/h4-7,19-20,22H,1-3H3

InChI Key

UWNUJPINKMRKKR-UHFFFAOYSA-N

Isomeric SMILES

COC1=C(OC)C(OC)=C2OC(=CC(=O)C2=C1O)C1=CC(O)=C(O)C=C1

Average Molecular Weight

360.3148

Monoisotopic Molecular Weight

360.084517488

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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111471 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 60.00%; H 4.48%; O 35.52%	DFC
Melting Point	Mp 197-198°	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 (e 77624) (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Sideritiflavone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-0119000000-d661f929d6e7c6e1e2a6	Spectrum
Predicted GC-MS	Sideritiflavone, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03di-1030190000-da25a150ef664eff6f06	Spectrum
Predicted GC-MS	Sideritiflavone, 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	splash10-03di-0009000000-341009b391d78207b8af	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0009000000-0f73369acc39d5f93764	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0cfr-2977000000-3274aff2824af897c04a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0009000000-9bdb314df607331460dc	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-0019000000-4a242a4a1e57df1b5552	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9271000000-f83431b833cacf2df46e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0009000000-1b2458f70b43c2827ff8	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aou-0009000000-3415977c64a46461f5ee	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0009000000-ef0e36da9abfe27aa076	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0009000000-c383b2e8879413a775be	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ks-0249000000-439492fde1587ad3646e	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

136978

ChEMBL ID

CHEMBL312790

KEGG Compound ID

Not Available

Pubchem Compound ID

155493

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB38356

CRC / DFC (Dictionary of Food Compounds) ID

HBZ77-A:KZB66-Z

EAFUS ID

Not Available

Dr. Duke ID

SIDERITOFLAVONE

BIGG ID

Not Available

KNApSAcK ID

C00003927

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-arthritic	52217	An agent that reduces joint inflammation and alleviates symptoms of arthritis, commonly used in managing rheumatoid arthritis, osteoarthritis, and other inflammatory joint disorders, to improve mobility and quality of life.	DUKE
Anti-cataract	52217	An agent that prevents or slows the formation of cataracts, reducing oxidative stress and inflammation in the lens of the eye, commonly used to manage age-related cataracts and other ocular disorders.	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