Polydatin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Polydatin
DrugBank Accession Number
DB11263
Background

Polydatin, or Piceid, is a natural precursor and glycoside form of resveratrol with a monocrystalline structure. While it is isolated from the bark of Picea sitchensis or Polygonum cuspidatum, polydatin may be detected in grape, peanut, hop cones, red wines, hop pellets, cocoa-containing products, chocolate products and many daily diets 1. Polydatin possesses anti-inflammatory, immunoregulatory, anti-oxidative and anti-tumor activities. It is shown to mediate a cytotoxic action on colorectal cancer cells by inducing cell arrest and apoptosis 4.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 390.388
Monoisotopic: 390.131467668
Chemical Formula
C20H22O8
Synonyms
  • 3,4,5-Trihydroxystilbene-3-beta-monoglucoside
  • 3,4',5-trihydroxystilbene-3-β-d-glucoside
  • Piceid
  • Polydatin (E)-isomer
  • Resveratrol 3-O-beta-glucopyranoside
  • resveratrol-3-O-b-mono-D-glucoside
  • trans-piceid
  • trans-resveratrol 3-O-β-D-glucoside
  • trans-resveratrol 3-β-D-glucoside
  • trans-resveratrol 3-β-glucoside

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Products

Products2
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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Sooryehan Pure Whitening Spot TreatmentCream0.21 mL/100mLTopicalLg Household & Health Care Ltd.2010-04-26Not applicableUS flag
Sooryehan Pure-WhiteningCream0.22 mL/100mLTopicalLg Household & Health Care Ltd.2010-04-26Not applicableUS flag
Sooryehan Pure-Whitening EssenceCream0.22 1/100mLTopicalLg Household & Health Care Ltd.2010-05-14Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Sooryehan Bichaek Pure Whitening AmplePolydatin (0.001 mL/100mL) + Atractylodes lancea root oil (0.053 mL/100mL)CreamTopicalLg Household & Health Care Ltd.2011-12-142012-06-14US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Sooryehan Bichaek Pure Whitening AmplePolydatin (0.001 mL/100mL) + Atractylodes lancea root oil (0.053 mL/100mL)CreamTopicalLg Household & Health Care Ltd.2011-12-142012-06-14US flag
Sooryehan Pure-WhiteningPolydatin (0.22 mL/100mL)CreamTopicalLg Household & Health Care Ltd.2010-04-26Not applicableUS flag
Sooryehan Pure-Whitening EssencePolydatin (0.22 1/100mL)CreamTopicalLg Household & Health Care Ltd.2010-05-14Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as stilbene glycosides. These are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Stilbenes
Sub Class
Stilbene glycosides
Direct Parent
Stilbene glycosides
Alternative Parents
Phenolic glycosides / Hexoses / O-glycosyl compounds / Styrenes / Phenoxy compounds / Phenol ethers / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Oxanes / Secondary alcohols
show 5 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Acetal / Alcohol / Aromatic heteromonocyclic compound / Benzenoid / Glycosyl compound / Hexose monosaccharide / Hydrocarbon derivative / Monocyclic benzene moiety
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
beta-D-glucoside, monosaccharide derivative, polyphenol, stilbenoid (CHEBI:8198) / Diphenyl ethers, biphenyls, dibenzyls and stilbenes, Stilbenes (C10275) / Diphenyl ethers, biphenyls, dibenzyls and stilbenes (LMPK13090012)
Affected organisms
Not Available

Chemical Identifiers

UNII
XM261C37CQ
CAS number
27208-80-6
InChI Key
HSTZMXCBWJGKHG-CUYWLFDKSA-N
InChI
InChI=1S/C20H22O8/c21-10-16-17(24)18(25)19(26)20(28-16)27-15-8-12(7-14(23)9-15)2-1-11-3-5-13(22)6-4-11/h1-9,16-26H,10H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1
IUPAC Name
(2S,3R,4S,5S,6R)-2-{3-hydroxy-5-[(1E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES
OC[C@H]1O[C@@H](OC2=CC(\C=C\C3=CC=C(O)C=C3)=CC(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

References

General References
  1. Du QH, Peng C, Zhang H: Polydatin: a review of pharmacology and pharmacokinetics. Pharm Biol. 2013 Nov;51(11):1347-54. doi: 10.3109/13880209.2013.792849. Epub 2013 Jul 18. [Article]
  2. Ravagnan G, De Filippis A, Carteni M, De Maria S, Cozza V, Petrazzuolo M, Tufano MA, Donnarumma G: Polydatin, a natural precursor of resveratrol, induces beta-defensin production and reduces inflammatory response. Inflammation. 2013 Feb;36(1):26-34. doi: 10.1007/s10753-012-9516-8. [Article]
  3. Lanzilli G, Cottarelli A, Nicotera G, Guida S, Ravagnan G, Fuggetta MP: Anti-inflammatory effect of resveratrol and polydatin by in vitro IL-17 modulation. Inflammation. 2012 Feb;35(1):240-8. doi: 10.1007/s10753-011-9310-z. [Article]
  4. De Maria S, Scognamiglio I, Lombardi A, Amodio N, Caraglia M, Carteni M, Ravagnan G, Stiuso P: Polydatin, a natural precursor of resveratrol, induces cell cycle arrest and differentiation of human colorectal Caco-2 cell. J Transl Med. 2013 Oct 20;11:264. doi: 10.1186/1479-5876-11-264. [Article]
Human Metabolome Database
HMDB0030564
KEGG Compound
C10275
PubChem Compound
5281718
PubChem Substance
347827958
ChemSpider
4445034
BindingDB
60919
RxNav
1364277
ChEBI
8198
ChEMBL
CHEMBL142652
ZINC
ZINC000004098633
Wikipedia
Piceid

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Unknown StatusTreatmentSeptic Shock / Shock, Hemorrhagic / Traumatic Shock1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
CreamTopical
CreamTopical0.21 mL/100mL
CreamTopical0.22 mL/100mL
CreamTopical0.22 1/100mL
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.766 mg/mLALOGPS
logP0.65ALOGPS
logP1.13ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)8.6ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area139.84 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity99.6 m3·mol-1ChemAxon
Polarizability40.19 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-1491000000-fc0e407ffe35757fc820

Drug created on December 03, 2015 16:51 / Updated on June 12, 2020 16:53