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=C(O)C=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=C1

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 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

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

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 `Fri Dec 15 19:49:58 GMT 2023` Edited by `admin` on `Fri Dec 15 19:49:58 GMT 2023`
Record UNII	K691M2Z08V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RHAPONTIN

Common Name

English

PONTICIN

Common Name

English

NSC-43321

Code

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)