ChemFOnt: Showing chemical card for delta-Viniferin (CFc000281251)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:27 UTC

Chemfont ID

CFc000281251

Molecule Identification

Common Name

delta-Viniferin

Definition

Delta-viniferin, also known as resveratrol (E)-dehydrodimer or delta-viniferin, is a member of the class of compounds known as 2-arylbenzofuran flavonoids. 2-arylbenzofuran flavonoids are phenylpropanoids containing the 2-phenylbenzofuran moiety. Delta-viniferin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Delta-viniferin can be found in grape wine, which makes delta-viniferin a potential biomarker for the consumption of this food product. Delta-viniferin is a resveratrol dehydrodimer. It is an isomer of epsilon-viniferin. It can be isolated from stressed grapevine (Vitis vinifera) leaves. It is also found in plant cell cultures. or in wine. It can also be found in Rheum maximowiczii .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,3S)-trans-Δ-viniferin	Generator
Resveratrol (e)-dehydrodimer	ChEMBL
Resveratrol trans-dehydrodimer	ChEMBL
Δ-viniferin	Generator

Chemical Formula

C₂₈H₂₂O₆

Average Molecular Weight

454.478

Monoisotopic Molecular Weight

454.141638428

IUPAC Name

5-[(2S,3S)-5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol

Traditional Name

5-[(2S,3S)-5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol

CAS Registry Number

62218-13-7

SMILES

[H][C@@]1(OC2=C(C=C(\C=C\C3=CC(O)=CC(O)=C3)C=C2)[C@]1([H])C1=CC(O)=CC(O)=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C28H22O6/c29-20-6-4-18(5-7-20)28-27(19-12-23(32)15-24(33)13-19)25-11-16(3-8-26(25)34-28)1-2-17-9-21(30)14-22(31)10-17/h1-15,27-33H/b2-1+/t27-,28+/m0/s1

InChI Key

LILPTCHQLRKZNG-LPGNHZEISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Linear 1,7-diphenylheptane skeleton
Neolignan skeleton
1-phenylcoumaran
Stilbene
Benzofuran
Coumaran
Resorcinol
Styrene
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Oxacycle
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

1-benzofurans (CHEBI:76141 )
polyphenol (CHEBI:76141 )
stilbenoid (CHEBI:76141 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301735)

Food

Vegetable

Stalk vegetable

Garden rhubarb (FooDB: FOOD00154)

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)
Red wine (FooDB: FOOD00911)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0021 g/L	ALOGPS
logP	4.56	ALOGPS
logP	5.96	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	130.04 m³·mol⁻¹	ChemAxon
Polarizability	48.73 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0301735

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000319

KNApSAcK ID

Not Available

Chemspider ID

8271010

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10095474

PDB ID

Not Available

ChEBI ID

76141

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for delta-Viniferin (CFc000281251)

MOL for CFc000281251 (delta-Viniferin)

3D MOL for CFc000281251 (delta-Viniferin)

3D SDF for CFc000281251 (delta-Viniferin)

3D-SDF for CFc000281251 (delta-Viniferin)

PDB for CFc000281251 (delta-Viniferin)

3D PDB for CFc000281251 (delta-Viniferin)

SMILES for CFc000281251 (delta-Viniferin)

INCHI for CFc000281251 (delta-Viniferin)

Structure for CFc000281251 (delta-Viniferin)

3D Structure for CFc000281251 (delta-Viniferin)