Showing Compound Pterostilbene (FDB012375)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:08 UTC

Update date

2019-11-26 03:06:39 UTC

Primary ID

FDB012375

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Pterostilbene

Description

Pterostilbene 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. Pterostilbene is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Pterostilbene can be found in common grape and grape wine, which makes pterostilbene a potential biomarker for the consumption of these food products. Pterostilbene is a stilbenoid chemically related to resveratrol. In plants, it serves a defensive phytoalexin role .

CAS Number

537-42-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(E)-4-(3,5-dimethoxystyryl)phenol	biospider
3',5'-Dimethoxy-4-stilbenol	biospider
3',5'-dimethoxy-4E-stilbenol	biospider
3',5'-dimethoxy-4trans-stilbenol	biospider
3',5'-dimethoxy-resveratrol	biospider
3,5-Dimethoxy-4'-hydroxy-trans-stilbene	biospider
3,5-Dimethoxy-4'-hydroxystilbene	biospider
4'-Hydroxy-3,5-dimethoxystilbene	db_source
4-((E)-2-(3,5-dimethoxyphenyl)ethenyl)phenol	biospider
4-(2-(3,5-Dimethoxyphenyl)ethenyl)phenol	biospider

Showing 1 to 10 of 24 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	3.48	ALOGPS
logP	3.69	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.42 m³·mol⁻¹	ChemAxon
Polarizability	27.7 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C16H16O3

IUPAC name

4-[(Z)-2-(3,5-dimethoxyphenyl)ethenyl]phenol

InChI Identifier

InChI=1S/C16H16O3/c1-18-15-9-13(10-16(11-15)19-2)4-3-12-5-7-14(17)8-6-12/h3-11,17H,1-2H3/b4-3-

InChI Key

VLEUZFDZJKSGMX-ARJAWSKDSA-N

Isomeric SMILES

COC1=CC(\C=C/C2=CC=C(O)C=C2)=CC(OC)=C1

Average Molecular Weight

256.2964

Monoisotopic Molecular Weight

256.109944378

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
Dimethoxybenzene
M-dimethoxybenzene
Anisole
Phenol ether
Phenoxy compound
Styrene
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

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 74.98%; H 6.29%; O 18.73%	DFC
Melting Point	Mp 85-86°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-3a2fab1dd228c459973f	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0390000000-b2e9352c3040f6ff3d27	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02td-3940000000-b2538ca0173aeb0463fe	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-05f710a9426addead5af	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0190000000-d66fb7d2d9cfbdd45416	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-3690000000-308cf11c76a28c844c2a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-1764cfa47ef5606fd849	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0790000000-ebf83e0eca3bf6a8379a	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002g-2960000000-8ec7e5cbccb6e8a32e77	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-e382f8a0b4d1e3b6f408	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0090000000-625eff2e5e4c3d4e88e0	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0673-0940000000-c1a3200bf94e6cbace94	2021-10-21	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C10287

Pubchem Compound ID

5281727

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

585

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

GZM37-C:HGQ93-S

EAFUS ID

Not Available

Dr. Duke ID

PTEROSTILBENE

BIGG ID

Not Available

KNApSAcK ID

C00002902

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

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti diabetic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti melanomic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti radicular			DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
chemopreventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cyclooxygenase inhibitor	35544	A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.	DUKE
cyclooxygenase-1 inhibitor	50630	A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.	DUKE
cyclooxygenase-2 inhibitor	50629	A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.	DUKE
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE