Showing Compound Vicenin 3 (FDB011642)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:45 UTC

Update date

2019-11-26 03:05:10 UTC

Primary ID

FDB011642

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Vicenin 3

Description

Apigenin 6-c-glucoside 8-c-riboside is a member of the class of compounds known as flavonoid 8-c-glycosides. Flavonoid 8-c-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Apigenin 6-c-glucoside 8-c-riboside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Apigenin 6-c-glucoside 8-c-riboside can be found in herbs and spices, which makes apigenin 6-c-glucoside 8-c-riboside a potential biomarker for the consumption of this food product.

CAS Number

59914-91-9

Structure

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

Synonyms

Show entries

Search:

Synonym	Source
2-(4-Hydroxyphenyl)-5,7-dihydroxy-6-b-D-glucopyranosyl-8-b-D-xylopyranosyl-4H-1-benzopyran-4-one	Generator
2-(4-Hydroxyphenyl)-5,7-dihydroxy-6-beta-D-glucopyranosyl-8-beta-D-xylopyranosyl-4H-1-benzopyran-4-one	ChEBI
2-(4-Hydroxyphenyl)-5,7-dihydroxy-6-β-D-glucopyranosyl-8-β-D-xylopyranosyl-4H-1-benzopyran-4-one	Generator
5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-8-[(2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]-4H-chromen-4-one	ChEBI
6-b-D-Glucopyranosyl-8-b-D-xylopyranosylapigenin	Generator
6-beta-D-Glucopyranosyl-8-beta-D-xylopyranosylapigenin	ChEBI
6-C-b-D-Glucosyl-8-C-b-D-xylosyl-4',5,7-trihydroxyflavone	Generator
6-C-beta-D-Glucosyl-8-C-beta-D-xylosyl-4',5,7-trihydroxyflavone	ChEBI
6-C-Glucopyranosyl-8-C-b-D-xylopyranosylapigenin	Generator
6-C-Glucopyranosyl-8-C-beta-D-xylopyranosylapigenin	ChEBI

Showing 1 to 10 of 17 entries

Predicted Properties

Property	Value	Source
logP	-2.2	ChemAxon
pKa (Strongest Acidic)	5.74	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	247.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	133.19 m³·mol⁻¹	ChemAxon
Polarizability	54.91 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C26H28O14

IUPAC name

5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]-4H-chromen-4-one

InChI Identifier

InChI=1S/C26H28O14/c27-6-13-18(32)21(35)23(37)26(40-13)15-19(33)14-10(29)5-12(8-1-3-9(28)4-2-8)39-24(14)16(20(15)34)25-22(36)17(31)11(30)7-38-25/h1-5,11,13,17-18,21-23,25-28,30-37H,6-7H2

InChI Key

MMDUKUSNQNWVET-UHFFFAOYSA-N

Isomeric SMILES

OCC1OC(C(O)C(O)C1O)C1=C(O)C(C2OCC(O)C(O)C2O)=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C=C1

Average Molecular Weight

564.4921

Monoisotopic Molecular Weight

564.147905604

Classification

Description

Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 8-C-glycosides

Alternative Parents

Substituents

Flavonoid-8-c-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
C-glycosyl compound
Chromone
Glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Monocyclic benzene moiety
Oxane
Monosaccharide
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Polyol
Oxacycle
Dialkyl ether
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Primary alcohol
Organic oxide
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 55.32%; H 5.00%; O 39.68%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

185958

Pubchem Substance ID

Not Available

ChEBI ID

35828

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

CLX66-B:GWY54-S

EAFUS ID

Not Available

Dr. Duke ID

VICENIN-3

BIGG ID

Not Available

KNApSAcK ID

C00006380

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

Show entries

Search:

Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Showing Compound Vicenin 3 (FDB011642)

Structure for FDB011642 (Vicenin 3)