Showing Compound Malvidin 3-glucoside-4-vinylphenol (FDB008660)

Record Information

Version

1.0

Creation date

2010-04-08 22:08:11 UTC

Update date

2020-02-24 19:10:56 UTC

Primary ID

FDB008660

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Malvidin 3-glucoside-4-vinylphenol

Description

Malvidin 3-glucoside-4-vinylphenol belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Malvidin 3-glucoside-4-vinylphenol is found, on average, in the highest concentration within grape wine. Malvidin 3-glucoside-4-vinylphenol has also been detected, but not quantified in, alcoholic beverages and common grapes (Vitis vinifera). This could make malvidin 3-glucoside-4-vinylphenol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Malvidin 3-glucoside-4-vinylphenol.

CAS Number

388089-39-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	0.078 g/L	ALOGPS
logP	2.93	ALOGPS
logP	1.27	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.72	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	200.9 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	162.75 m³·mol⁻¹	ChemAxon
Polarizability	61.11 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C31H29O13

IUPAC name

11-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-7-(4-hydroxyphenyl)-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2lambda4,8-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(13),2,4,6,9,11-hexaen-2-ylium

InChI Identifier

InChI=1S/C31H28O13/c1-39-21-7-14(8-22(40-2)25(21)35)29-30(44-31-28(38)27(37)26(36)23(12-32)43-31)17-11-18(13-3-5-15(33)6-4-13)41-19-9-16(34)10-20(42-29)24(17)19/h3-11,23,26-28,31-32,36-38H,12H2,1-2H3,(H2-,33,34,35)/p+1/t23-,26-,27+,28-,31+/m1/s1

InChI Key

QVDUZUIZMDYJSK-BGXVWEPQSA-O

Isomeric SMILES

COC1=CC(=CC(OC)=C1O)C1=[O+]C2=C3C(OC(=CC3=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C1=CC=C(O)C=C1)=CC(O)=C2

Average Molecular Weight

609.5542

Monoisotopic Molecular Weight

609.160816014

Classification

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

Bi- and polyflavonoid skeleton
Proanthocyanidin
Anthocyanin
Anthocyanidin-3-o-glycoside
Flavonoid o-glycoside
Flavonoid-3-o-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Dimethoxybenzene
1-benzopyran
M-dimethoxybenzene
Benzopyran
Methoxyphenol
Phenoxy compound
Methoxybenzene
Anisole
Phenol ether
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Heteroaromatic compound
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Acetal
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Plant

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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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 61.08%; H 4.80%; O 34.12%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0abc-9300080000-22cf15a97266f89c2379	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0c00-9200018000-3053735797f43e5447eb	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_2_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Malvidin 3-glucoside-4-vinylphenol, TMS_2_17, 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-0100009000-801f36a3a56a8b97162d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02ta-2400049000-b0aa469f9a38e691cd25	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9710200000-992992465bc73e4fbe14	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-2300009000-f3d89ac07104ef32e7a6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-6800009000-b9c1a62bb92d192249e6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9200000000-57c3846255b7b9e7a1bb	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000933000-6345ed787bf21c394ab3	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0000910000-fa59503587828c2e626a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-4300910000-0f6c707b37e30e47e8d1	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

30776925

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

DrugBank ID

Not Available

HMDB ID

HMDB31968

CRC / DFC (Dictionary of Food Compounds) ID

OJL40-V:DOT28-D

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00011187

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

DOT28-D:DOT28-D

Associated Foods

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Food	Content Range	Average	Reference

Common grape	Expected but not quantified	Not Available	KNAPSACK
Grape wine	0.08114 - 0.08114 mg/100 g	0.08114 mg/100 g	PHENOL EXPLORER

Showing 1 to 2 of 2 entries

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

de Villiers A, Vanhoenacker G, Majek P, Sandra P: Determination of anthocyanins in wine by direct injection liquid chromatography-diode array detection-mass spectrometry and classification of wines using discriminant analysis. J Chromatogr A. 2004 Oct 29;1054(1-2):195-204. Pubmed [Structure]

Content Reference

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.

Showing Compound Malvidin 3-glucoside-4-vinylphenol (FDB008660)

Structure for FDB008660 (Malvidin 3-glucoside-4-vinylphenol)