PHILLYRIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H34O11
Molecular Weight	534.5523
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C=C1OC)[C@@H]2OC[C@H]3[C@@H]2CO[C@@H]3C4=CC=C(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C(OC)=C4

InChI

InChIKey=KFFCKOBAHMGTMW-LGQRSHAYSA-N

InChI=1S/C27H34O11/c1-32-17-6-4-13(8-19(17)33-2)25-15-11-36-26(16(15)12-35-25)14-5-7-18(20(9-14)34-3)37-27-24(31)23(30)22(29)21(10-28)38-27/h4-9,15-16,21-31H,10-12H2,1-3H3/t15-,16-,21+,22+,23-,24+,25-,26+,27+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C27H34O11
Molecular Weight	534.5523
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23122079 | https://www.ncbi.nlm.nih.gov/pubmed/23751215
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27323762 https://www.ncbi.nlm.nih.gov/pubmed/24995500

Phillyrin, an active ingredient found in many medicinal plants and certain functional foods, elicits anti-obesity and anti-inflammatory properties in vivo. Phillyrin is one of the main chemical constituents of Forsythia suspensa (Thunb.), which has shown to be an important traditional Chinese medicine. Phillyrin, has being shown to possess various bioactivities, including anti-inflammatory, anti-oxidant, and antiviral activities. It has being reported that Phillyrin attenuates high glucose-induced lipid accumulation in human HepG2 hepatocytes through the activation of LKB1/AMP-activated protein kinase-dependent signalling.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Influenza A virus 9 Target ID: CHEMBL613740 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27323762	Inhibitor 8504
inflammatory response 47 Target ID: GO:0006954 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23751215 \| https://www.ncbi.nlm.nih.gov/pubmed/22210027	Inhibitor 8504	18.9 µM [IC50]
AMP-activated protein kinase, AMPK 17 Target ID: CHEMBL2096907 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23122079	Activator 1447
Cyclooxygenase 89 Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11345691	Inhibitor 8504	45.6 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Influenza A virus infection 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27323762	Primary	Preclinical	Unknown Approved Use Unknown
Acute lung injury 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23751215	Primary	Preclinical	Unknown Approved Use Unknown
Obesity 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23122079 https://www.ncbi.nlm.nih.gov/pubmed/15981888	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Phillyrin, a natural lignan, attenuates tumor necrosis factor α-mediated insulin resistance and lipolytic acceleration in 3T3-L1 adipocytes.	2014-07	24995500
Phillyrin attenuates LPS-induced pulmonary inflammation via suppression of MAPK and NF-κB activation in acute lung injury mice.	2013-10	23751215

Patents

Sample Use Guides

In Vivo Use Guide

i.p., 10 or 20 mg/kg/day for 3 days

Route of Administration: Intraperitoneal

In Vitro Use Guide

Phillyrin inhibits release of the cyclo-oxygenase metabolites prostaglandin E2 (IC50 value 45.6 uM) and to a lesser extent reducing thromboxane B2 levels (IC50 value 168 uM) in human platelets

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:19:30 GMT 2025` Edited by `admin` on `Mon Mar 31 22:19:30 GMT 2025`
Record UNII	VE9P4964MG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FORSYTHIN

Preferred Name

English

PHILLYRIN

Common Name

English

PHYLLYRIN

Common Name

English

4-((1S,3AR,4R,6AR))-4-(4-(3,4-DIMETHOXYPHENYL)TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1-YL)-2-METHOXYPHENYL-.BETA.-D-GLUCOPYRANOSIDE

Systematic Name

English

.BETA.-D-GLUCOPYRANOSIDE, 4-((1S,3AR,4R,6AR)-4-(3,4-DIMETHOXYPHENYL)TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1-YL)-2-METHOXYPHENYL

Systematic Name

English

PHILLYROSIDE, (+)-

Common Name

English

PHILLYRIN [MI]

Common Name

English

Code System Code Type Description

MERCK INDEX

m8704