RHAPONTIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H24O9
Molecular Weight	420.4099
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(\C=C\C2=CC(O)=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C2)C=C1O

InChI

InChIKey=GKAJCVFOJGXVIA-DXKBKAGUSA-N

InChI=1S/C21H24O9/c1-28-16-5-4-11(8-15(16)24)2-3-12-6-13(23)9-14(7-12)29-21-20(27)19(26)18(25)17(10-22)30-21/h2-9,17-27H,10H2,1H3/b3-2+/t17-,18-,19+,20-,21-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C21H24O9
Molecular Weight	420.4099
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27930969 | https://www.ncbi.nlm.nih.gov/pubmed/28364627

Rhapontin (3, 3', 5-trihydroxy-4'-methoxystilbene-3-O-glucoside), a natural stilbenoid glycoside widely distributed in the medicinal plants of Rheum genus in China, has anti-thrombotic, anti-allergic and anti-diabetic activity and can be used as the potent antihyperlipidemic agent. In addition was shown, that rhapontin possessed anti-fibrotic activities and could prevent pulmonary fibrosis in vivo by modulating AMPK activation and suppressing the TGF-β/Smad pathway.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
TGF-β/Smad pathway 1 Target ID: TGF-β/Smad pathway Sources: https://www.ncbi.nlm.nih.gov/pubmed/28364627	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Protective role of rhapontin in experimental pulmonary fibrosis in vitro and in vivo.	2017-06	28364627
Rhapontin ameliorates colonic epithelial dysfunction in experimental colitis through SIRT1 signaling.	2017-01	27930969
Antihyperlipidemic effects of rhapontin and rhapontigenin from rheum undulatum in rats fed a high-cholesterol diet.	2014-08	25127020

Patents

Sample Use Guides

In Vivo Use Guide

In a dextran sodium sulfate (DSS)-induced mouse model: oral administration of rhapontin (100mg/kg) significantly attenuated colonic pathological damage and remarkably inhibited infiltration by inflammatory cells, myeloperoxidase (MPO) activity, NLRP3 inflammasome activation and SIRT1 expression in the colon.

Route of Administration: Oral

In Vitro Use Guide

It was studied the effect of rhapontin alone at difference dosages (0.1–5 μM) on TGF-β1-mediated extracellular matrix (ECM) deposition in primary lung fibroblast (PLF) cells, on TGF-β1 secretion in LPS -stimulated human THP-1, derived macrophages in vitro. Rhapontin suppressed myoﬁbroblast differentiation in a dose-dependent manner, the signiﬁcant reduction was observed at the concentration of 5 μM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:58:09 GMT 2025` Edited by `admin` on `Mon Mar 31 19:58:09 GMT 2025`
Record UNII	K691M2Z08V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-43321

Preferred Name

English

RHAPONTIN

Common Name

English

PONTICIN

Common Name

English

3-HYDROXY-5-((1E)-2-(3-HYDROXY-4-METHOXYPHENYL)ETHENYL)PHENYL .BETA.-D-GLUCOPYRANOSIDE

Common Name

English

RHAPONTIN [MI]

Common Name

English

RHAPONTICIN

Common Name

English

Classification Tree Code System Code

DSLD

3897 (Number of products:9)