5-[(2R,3S)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
PubChem CID
5315234
Structure
Molecular Formula
Synonyms
- (2R,3S)-trans-epsilon-viniferin
- 5-[(2R,3S)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
- 5-{(2R,3S)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl}benzene-1,3-diol
- CHEBI:76143
- AKOS040736044
Molecular Weight
454.5 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
- Create:2006-01-18
- Modify:2025-01-10
Description
(2R,3S)-trans-epsilon-viniferin is a stilbenoid that is the (2R,3S)-trans-stereoisomer of epsilon-viniferin, obtained by cyclodimerisation of trans-resveratrol. It is a member of 1-benzofurans, a polyphenol and a stilbenoid. It is functionally related to a trans-resveratrol. It is an enantiomer of a (2S,3R)-trans-epsilon-viniferin.
(2R,3S)-trans-epsilon-viniferin has been reported in Vatica affinis, Vitis vinifera, and other organisms with data available.
Chemical Structure Depiction
5-[(2R,3S)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)
InChI=1S/C28H22O6/c29-20-7-2-16(3-8-20)1-4-18-11-24(33)15-25-26(18)27(19-12-22(31)14-23(32)13-19)28(34-25)17-5-9-21(30)10-6-17/h1-15,27-33H/b4-1+/t27-,28-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.05.07)
FQWLMRXWKZGLFI-PAKBJIOWSA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)
C1=CC(=CC=C1/C=C/C2=C3[C@@H]([C@@H](OC3=CC(=C2)O)C4=CC=C(C=C4)O)C5=CC(=CC(=C5)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C28H22O6
Computed by PubChem 2.1 (PubChem release 2021.05.07)
- (2R,3S)-trans-epsilon-viniferin
- 5-[(2R,3S)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
- 5-{(2R,3S)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl}benzene-1,3-diol
- CHEBI:76143
- AKOS040736044
- NS00097268
- Q27145781
- 1307823-52-4
- 5-((2R,3S)-6-Hydroxy-2-(4-hydroxyphenyl)-4-((E)-4-hydroxystyryl)-2,3-dihydrobenzofuran-3-yl)benzene-1,3-diol
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
454.5 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
5.4
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
454.14163842 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
454.14163842 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
110 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
34
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
672
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
2
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.05.07)
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
455.148
Instrument
Agilent 6530 Q-TOF
Instrument Type
LC-ESI-QTOF
Ionization Mode
positive
Collision Energy
40 V
Retention Time
3.896
Top 5 Peaks
107.0481 100
199.0740 25.11
197.0554 20.47
239.0715 15.19
181.0603 11.69
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
455.148
Instrument
Agilent 6530 Q-TOF
Instrument Type
LC-ESI-QTOF
Ionization Mode
positive
Collision Energy
20 V
Retention Time
3.896
Top 5 Peaks
107.0483 100
215.0679 67.18
199.0751 40.40
349.1028 38.33
361.1077 37.52
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Similar Compounds (2D)
Similar Conformers (3D)
Same Count
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
- ChEBI(2R,3S)-trans-epsilon-viniferinhttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:76143
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/(2R,3S)-trans-epsilon-viniferinhttps://www.wikidata.org/wiki/Q27145781LOTUS Treehttps://lotus.naturalproducts.net/
- Natural Product Activity and Species Source (NPASS)
- MassBank of North America (MoNA)LICENSEThe content of the MoNA database is licensed under CC BY 4.0.https://mona.fiehnlab.ucdavis.edu/documentation/license5-[(2R,3S)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diolhttps://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(compound.metaData.name:%27InChIKey%27%20and%20compound.metaData.value:%27FQWLMRXWKZGLFI-PAKBJIOWSA-N%27)
- Wikidata(2R,3S)-trans-epsilon-viniferinhttps://www.wikidata.org/wiki/Q27145781
- PubChem
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/NORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
CONTENTS