ChemFOnt: Showing chemical card for Piceatannol (CFc000282893)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:35:40 UTC

Chemfont ID

CFc000282893

Molecule Identification

Common Name

Piceatannol

Definition

Piceatannol, also known as (Z)-3,5,3',4'-tetrahydroxystilbene, is a member of the class of compounds known as stilbenes. Stilbenes 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. Piceatannol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Piceatannol can be synthesized from cis-stilbene. Piceatannol can also be synthesized into cis-astringin. Piceatannol can be found in common grape and grape wine, which makes piceatannol a potential biomarker for the consumption of these food products. Piceatannol is a stilbenoid, a type of phenolic compound .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(Z)-3,5,3',4'-Tetrahydroxystilbene	ChEBI

Chemical Formula

C₁₄H₁₂O₄

Average Molecular Weight

244.246

Monoisotopic Molecular Weight

244.073558866

IUPAC Name

4-[(Z)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol

Traditional Name

4-[(Z)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol

CAS Registry Number

4339-71-3

SMILES

[H]\C(=C(/[H])C1=CC(O)=CC(O)=C1)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1-

InChI Key

CDRPUGZCRXZLFL-UPHRSURJSA-N

Chemical Taxonomy

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
Styrene
Resorcinol
Catechol
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

polyphenol (CHEBI:76156 )
stilbenol (CHEBI:76156 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303377)

Common grape (FooDB: FOOD00204)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.097 g/L	ALOGPS
logP	2.12	ALOGPS
logP	3.1	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.91	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.44 m³·mol⁻¹	ChemAxon
Polarizability	24.3 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

External Links

HMDB ID

HMDB0303377

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012295

KNApSAcK ID

Not Available

Chemspider ID

5036268

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

76156

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Piceatannol (CFc000282893)

MOL for CFc000282893 (Piceatannol)

3D MOL for CFc000282893 (Piceatannol)

3D SDF for CFc000282893 (Piceatannol)

3D-SDF for CFc000282893 (Piceatannol)

PDB for CFc000282893 (Piceatannol)

3D PDB for CFc000282893 (Piceatannol)

SMILES for CFc000282893 (Piceatannol)

INCHI for CFc000282893 (Piceatannol)

Structure for CFc000282893 (Piceatannol)

3D Structure for CFc000282893 (Piceatannol)