Showing Compound Dihydroresveratrol (FDB029989)

Record Information

Version

1.0

Creation date

2012-01-20 01:16:41 UTC

Update date

2020-09-17 15:30:07 UTC

Primary ID

FDB029989

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Dihydroresveratrol

Description

Dihydroresveratrol or 5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol is a stilbenol where hydroxy groups at positions 1, 3 and 4' are added to 1,1'-ethane-1,2-diyldibenzene. Dihydroresveratrol is an aromatic polyketide, which contains alternating carbonyl groups and methylene groups. Dihydroresveratrol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Dihydroresveratrol, a prominent polyphenol component of red wine (PMID: 20630177), has a profound proliferative effect on hormone-sensitive tumor cell lines at picomolar concentrations. Dihydroresveratol is a derivative of resveratol and one of the main metabolites of two stereoisomers of resveratol, trans resveratrol and cis resveratrol. Dihydroresveratrol is formed in the intestine by microbial hydrogenation of trans-resveratrol (PMID: 20509689). Trans-resveratrol is a common component of fruits and berries, particularly grapes (Vitis vinifera), where it is formed as a response to the stress of weather conditions, microbe infections, or direct sunlight. Cis resveratrol is as a minor component in some berries, grapes, and wines along with trans-resveratrol (PMID: 20813524). Resveratrol has received special attention due to its diverse and potentially beneficial biological properties. The compound is currently on the market as a popular dietary supplement and is under clinical trials for treatment of some types of cancers (PMID: 25446990), metabolic syndrome, Alzheimer‚Äôs disease, type 2 diabetes, obesity (PMID: 25790328), neurologic syndrome, and some symptoms of aging.

CAS Number

58436-28-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3,4',5-Trihydroxybibenzyl	ChEBI
Dihydro-resveratrol	HMDB
5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.081 g/L	ALOGPS
logP	2.45	ALOGPS
logP	3.6	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.3	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	66.34 m³·mol⁻¹	ChemAxon
Polarizability	24.87 Å³	ChemAxon
Number of Rings	2	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

C14H14O3

IUPAC name

5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol

InChI Identifier

InChI=1S/C14H14O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h3-9,15-17H,1-2H2

InChI Key

HITJFUSPLYBJPE-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1

Average Molecular Weight

230.2592

Monoisotopic Molecular Weight

230.094294314

Classification

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

stilbenol (CHEBI:4582 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (C10255 )
Bibenzyls (C10255 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (LMPK13090035 )

Ontology

Red wine

Fruits and vegetables:

Fruits:

Grapes

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
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	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Dihydroresveratrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0adi-3920000000-719fe242334d208b9ba6	Spectrum
Predicted GC-MS	Dihydroresveratrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-0019-0930000000-98789a2bfadb2e5294f9	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, positive	splash10-0a4i-3900000000-8401a4b05cec11937e91	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 50V, positive	splash10-0a4i-1900000000-63077beabbd74f9667da	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 6V, positive	splash10-0019-0930000000-d89311ce59a12d10e350	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, negative	splash10-00fr-0940000000-e764d7f7fec0ad95522d	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, negative	splash10-004i-0590000000-c0d04f560a51a3bb619d	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, negative	splash10-001i-9500000000-361c896f8255aa9a4a1d	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, negative	splash10-00di-3900000000-71299800417044263bbb	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 50V, negative	splash10-001i-9000000000-35af2f10fc300befdb21	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 50V, negative	splash10-003r-9100000000-ac6d40eae4eba92c915d	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 6V, negative	splash10-004i-0590000000-c0d04f560a51a3bb619d	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 6V, negative	splash10-00fr-0940000000-ef1a37528e823253c1b3	Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0019-0930000000-5350f748bb4caf143bc6	Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0490000000-ad670ae9686c694e73c1	Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a4i-3900000000-e4d975cfe5ed55a80b23	Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Negative	splash10-00ar-5930000000-21f41106079ae20bf096	Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a4i-3900000000-1d5073ba2d9174c455dd	Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-053i-0940000000-ac0deac644455c15b41c	Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0a4i-1900000000-6510d3485dd518836d05	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0190000000-dbff90b6a63d99897a08	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053r-0950000000-1f3064cc04762cbfb39f	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-5900000000-e5b4f11464b84f6190ef	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-3f1af4fc1138d28d1e8f	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0190000000-b3b2e29cac9a8f7c4f14	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0553-1920000000-bc1898e08955e5b6385a	Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

185914

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB08466

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

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

1008

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

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

Showing Compound Dihydroresveratrol (FDB029989)

Structure for FDB029989 (Dihydroresveratrol)