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Showing Compound Pterostilbene (FDB012375)

Record Information
Version1.0
Creation date2010-04-08 22:10:08 UTC
Update date2019-11-26 03:06:39 UTC
Primary IDFDB012375
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePterostilbene
DescriptionPterostilbene 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 Number537-42-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(E)-4-(3,5-dimethoxystyryl)phenolbiospider
3,5-Dimethoxy-4'-hydroxy-trans-stilbenebiospider
3,5-Dimethoxy-4'-hydroxystilbenebiospider
3',5'-Dimethoxy-4-stilbenolbiospider
3',5'-dimethoxy-4E-stilbenolbiospider
3',5'-dimethoxy-4trans-stilbenolbiospider
3',5'-dimethoxy-resveratrolbiospider
4-((E)-2-(3,5-dimethoxyphenyl)ethenyl)phenolbiospider
4-(2-(3,5-Dimethoxyphenyl)ethenyl)phenolbiospider
4-[(1E)-2-(3,5-Dimethoxyphenyl)ethenyl]phenolbiospider
4-[(3,5-Dimethoxyphenyl)ethenyl]phenoldb_source
4-[(E)-2-(3,5-Dimethoxy-phenyl)-vinyl]-phenolbiospider
4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenolbiospider
4-[2-(3,5-Dimethoxy-phenyl)-vinyl]-phenolbiospider
4-Stilbenol, 3',5'-dimethoxy-, (E)-biospider
4'-Hydroxy-3,5-dimethoxystilbenedb_source
4E-(2-(3,5-dimethoxyphenyl)ethenyl)phenolbiospider
4trans-(2-(3,5-dimethoxyphenyl)ethenyl)phenolbiospider
E 4-[2-(3,5-Dimethoxy-phenyl)-vinyl]-phenolbiospider
Phenol, 4-(2-(3,5-dimethoxyphenyl)ethenyl)-, (E)-biospider
Pterocarpus marsupiumbiospider
Pterostilbenbiospider
Pterostilbenedb_source
Pterostilbene, pterocarpus marsupiumbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP3.48ALOGPS
logP3.69ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.5ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity76.42 m³·mol⁻¹ChemAxon
Polarizability27.7 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H16O3
IUPAC name4-[(Z)-2-(3,5-dimethoxyphenyl)ethenyl]phenol
InChI IdentifierInChI=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 KeyVLEUZFDZJKSGMX-ARJAWSKDSA-N
Isomeric SMILESCOC1=CC(\C=C/C2=CC=C(O)C=C2)=CC(OC)=C1
Average Molecular Weight256.2964
Monoisotopic Molecular Weight256.109944378
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
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 FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 74.98%; H 6.29%; O 18.73%DFC
Melting PointMp 85-86°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data315 (e 22500) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-3a2fab1dd228c459973f2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0390000000-b2e9352c3040f6ff3d272016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02td-3940000000-b2538ca0173aeb0463fe2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-05f710a9426addead5af2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0190000000-d66fb7d2d9cfbdd454162016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-3690000000-308cf11c76a28c844c2a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-1764cfa47ef5606fd8492021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0790000000-ebf83e0eca3bf6a8379a2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002g-2960000000-8ec7e5cbccb6e8a32e772021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-e382f8a0b4d1e3b6f4082021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0090000000-625eff2e5e4c3d4e88e02021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0673-0940000000-c1a3200bf94e6cbace942021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC10287
Pubchem Compound ID5281727
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID585
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDGZM37-C:HGQ93-S
EAFUS IDNot Available
Dr. Duke IDPTEROSTILBENE
BIGG IDNot Available
KNApSAcK IDC00002902
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti diabetic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antioxidant22586 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
anti radicularDUKE
chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cyclooxygenase-1 inhibitor50630 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.DUKE
cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
cyclooxygenase inhibitor35544 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
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hyperglycemic76916 A drug which increases the blood glucose level.DUKE
hypocholesterolemicDUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
hypolipidemicDUKE
hypotensiveDUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phytoalexin26115 A toxin made by a plant that acts against an organism attacking it.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.