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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H22O8
Molecular Weight 390.3839
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of POLYDATIN

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

InChI

InChIKey=HSTZMXCBWJGKHG-CUYWLFDKSA-N
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

HIDE SMILES / InChI

Molecular Formula C20H22O8
Molecular Weight 390.3839
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.webmedcentral.com/article_view/5000

Polydatin (PD, also named pieceid, (E)-piceid, (E)-polydatin, trans-polydatin, 3,40 ,5-trihydroxystilbene-3-b-D-glucoside) is a monocrystalline compound originally isolated from the root and rhizome of Polygonum cuspidatum Sieb. et Zucc. (Polygonaceae), a traditional Chinese medicine that has long been used in China as an analgesic, anti-pyretic, diuretic and expectorant. It is a glucoside of resveratrol (3,40 ,5-trihydroxystilbene) in which the glucoside group bound to the position C-3 substitutes a hydroxyl group, belonging to stilbene phytoalexins. Polydatin can also be detected in grape, peanut, hop cones, red wines, hop pellets, cocoa-containing products, chocolate products and many daily diets. Polydatin is the most abundant form of resveratrol in nature. Polydatin shows many pharmacological effects confirmed by numerous investigations, including cardiovascular protection, neuroprotection, anti-inflammation, immunoregulation, anti-oxidation, anti-tumour and liver and lung protective effects. Polydatin has found its way into clinical trials for the treatment of hemorrhagic shock and irritable bowel syndrome.

CNS Activity

Curator's Comment: It has shown that PD can cross the blood–brain barrier to protect brain tissues from ischemia–reperfusion injury or cerebral ischemia

Approval Year

PubMed

PubMed

TitleDatePubMed
Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures.
2001
In vitro inhibition of human cGMP-specific phosphodiesterase-5 by polyphenols from red grapes.
2005 Mar 23
Role of peptide primary sequence in polyphenol-protein recognition: an example with neurotensin.
2005 Nov 30
Anti-HIV activities of the compounds isolated from Polygonum cuspidatum and Polygonum multiflorum.
2010 Jun
Polydatin attenuated food allergy via store-operated calcium channels in mast cell.
2013 Jul 7
The stilbenes resveratrol, pterostilbene and piceid affect growth and stress resistance in mammalian cells via a mechanism requiring estrogen receptor beta and the induction of Mn-superoxide dismutase.
2014 Feb
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: can also be used as oral tablets; 200 mg PEA+20 mg polydatin; 2 tablets/day; 12 weeks https://clinicaltrials.gov/ct2/show/NCT01370720
Shock treatment: dilute two 100mg/5mL vials of HW6 (Polydatin) into 500mL 0.9% NaCl injection and administer as i.v. infusion over 2 hours. The drug should be given as early as possible right after the IC Form is signed on Day 1, and once every 24 hours for additional 4 doses.
Route of Administration: Intravenous
Polydatin attenuated phenylephrine-induced inhibition of hypertrophy of murine cardiomyocytes in a concentration-dependent manner with a complete inhibition of hypertrophy at the concentration of 50 uM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:36:56 GMT 2023
Edited
by admin
on Fri Dec 15 17:36:56 GMT 2023
Record UNII
XM261C37CQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
POLYDATIN
INCI  
INCI  
Official Name English
3,4'-5-TRIHYDROXYSTILBENE-3-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
5-((1E)-2-(4-HYDROXYPHENYL)ETHENYL)-1,3-BENZENEDIOL-3-.BETA.-MONO-D-GLUCOSIDE
Common Name English
PICEID
Common Name English
TRANS-POLYDATIN
Common Name English
3-Hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenyl β-D-glucopyranoside
Common Name English
GLUCOPYRANOSIDE, 3-HYDROXY-5-(P-HYDROXYSTYRYL)PHENYL, .BETA.-D-
Common Name English
RESVERATROL 3-.BETA.-MONO-D-GLUCOSIDE [MI]
Common Name English
.BETA.-D-GLUCOPYRANOSIDE, 3-HYDROXY-5-((1E)-2-(4-HYDROXYPHENYL)ETHENYL)PHENYL
Common Name English
POLYDATIN [INCI]
Common Name English
Polydatin [WHO-DD]
Common Name English
POLYDATIN [USP-RS]
Common Name English
.BETA.-D-GLUCOPYRANOSIDE, 3-HYDROXY-5-(2-(4-HYDROXYPHENYL)ETHENYL)PHENYL
Common Name English
Classification Tree Code System Code
DSLD 4329 (Number of products:1)
Created by admin on Fri Dec 15 17:36:57 GMT 2023 , Edited by admin on Fri Dec 15 17:36:57 GMT 2023
Code System Code Type Description
RXCUI
1364277
Created by admin on Fri Dec 15 17:36:57 GMT 2023 , Edited by admin on Fri Dec 15 17:36:57 GMT 2023
PRIMARY RxNorm
DAILYMED
XM261C37CQ
Created by admin on Fri Dec 15 17:36:57 GMT 2023 , Edited by admin on Fri Dec 15 17:36:57 GMT 2023
PRIMARY
FDA UNII
XM261C37CQ
Created by admin on Fri Dec 15 17:36:57 GMT 2023 , Edited by admin on Fri Dec 15 17:36:57 GMT 2023
PRIMARY
CAS
27208-80-6
Created by admin on Fri Dec 15 17:36:57 GMT 2023 , Edited by admin on Fri Dec 15 17:36:57 GMT 2023
PRIMARY
MERCK INDEX
m9549
Created by admin on Fri Dec 15 17:36:57 GMT 2023 , Edited by admin on Fri Dec 15 17:36:57 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
PICEID
Created by admin on Fri Dec 15 17:36:57 GMT 2023 , Edited by admin on Fri Dec 15 17:36:57 GMT 2023
PRIMARY
EVMPD
SUB34035
Created by admin on Fri Dec 15 17:36:57 GMT 2023 , Edited by admin on Fri Dec 15 17:36:57 GMT 2023
PRIMARY
PUBCHEM
5281718
Created by admin on Fri Dec 15 17:36:57 GMT 2023 , Edited by admin on Fri Dec 15 17:36:57 GMT 2023
PRIMARY
DRUG BANK
DB11263
Created by admin on Fri Dec 15 17:36:57 GMT 2023 , Edited by admin on Fri Dec 15 17:36:57 GMT 2023
PRIMARY
EPA CompTox
DTXSID001030555
Created by admin on Fri Dec 15 17:36:57 GMT 2023 , Edited by admin on Fri Dec 15 17:36:57 GMT 2023
PRIMARY
RS_ITEM_NUM
1546194
Created by admin on Fri Dec 15 17:36:57 GMT 2023 , Edited by admin on Fri Dec 15 17:36:57 GMT 2023
PRIMARY
MESH
C058229
Created by admin on Fri Dec 15 17:36:57 GMT 2023 , Edited by admin on Fri Dec 15 17:36:57 GMT 2023
PRIMARY
CHEBI
8198
Created by admin on Fri Dec 15 17:36:57 GMT 2023 , Edited by admin on Fri Dec 15 17:36:57 GMT 2023
PRIMARY
DRUG CENTRAL
4613
Created by admin on Fri Dec 15 17:36:57 GMT 2023 , Edited by admin on Fri Dec 15 17:36:57 GMT 2023
PRIMARY
SMS_ID
100000127888
Created by admin on Fri Dec 15 17:36:57 GMT 2023 , Edited by admin on Fri Dec 15 17:36:57 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY