SCHISANDRIN A

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H32O6
Molecular Weight	416.5073
Optical Activity	UNSPECIFIED
Additional Stereochemistry	Yes
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0
Stereo Comments	AXIAL, R

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(OC)C(OC)=C2C(C[C@H](C)[C@H](C)CC3=CC(OC)=C(OC)C(OC)=C23)=C1

InChI

InChIKey=JEJFTTRHGBKKEI-OKILXGFUSA-N

InChI=1S/C24H32O6/c1-13-9-15-11-17(25-3)21(27-5)23(29-7)19(15)20-16(10-14(13)2)12-18(26-4)22(28-6)24(20)30-8/h11-14H,9-10H2,1-8H3/t13-,14+

HIDE SMILES / InChI

Molecular Formula	C24H32O6
Molecular Weight	416.5073
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29115385 | https://www.ncbi.nlm.nih.gov/pubmed/28338050 | https://www.ncbi.nlm.nih.gov/pubmed/24992201

Schisandrin A is a bioactive lignan occurring in the fruits of plants of the Schisandra genus that have traditionally been used in Korea for treating various inflammatory diseases. Schisandrin A inhibits dengue viral replication via upregulating antiviral interferon responses through STAT signaling pathway. Schisandrin A represents a potential antiviral agent to block DENV replication in vitro and in vivo. Schisandrin A has been widely reported as being very effective for the treatment of liver disease. The hepatoprotective mechanisms of schisandrin A may include activation of autophagy flux and inhibition of apoptosis.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dengue virus 2 3 Target ID: CHEMBL613966 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28338050	Inhibitor 8297	28.1 µM [EC50]
UDP-glucuronosyltransferase 1-1 15 Target ID: CHEMBL1287617 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26084208	Inhibitor 8297
UDP-glucuronosyltransferase 1-3 6 Target ID: CHEMBL3542435 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26084208	Inhibitor 8297
Solute carrier organic anion transporter family member 1B1 32 Target ID: CHEMBL1697668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25975095	Activator 1430
Cytochrome P450 2C19 51 Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24855828	Inhibitor 8297	86.41 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Acne 98 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28875271	Primary	Basic research	Unknown Approved Use Unknown
Dengue fever 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28338050	Primary	Preclinical	Unknown Approved Use Unknown
Liver disease 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24992201	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibitory effects of continuous ingestion of Schisandrin A on CYP3A in the rat.	2012 Feb	21895978
The protective mechanism of schisandrin A in d-galactosamine-induced acute liver injury through activation of autophagy.	2014 Oct	24992201
Schisandrin A inhibits dengue viral replication via upregulating antiviral interferon responses through STAT signaling pathway.	2017 Mar 24	28338050
Schisandrin A suppresses lipopolysaccharide-induced inflammation and oxidative stress in RAW 264.7 macrophages by suppressing the NF-κB, MAPKs and PI3K/Akt pathways and activating Nrf2/HO-1 signaling.	2018 Jan	29115385

Patents

Sample Use Guides

In Vivo Use Guide

Male Sprague-Dawley rats were intragastrically administered with varied doses of Schisandrin A (8 mg/kg or 16 mg/kg or 32 mg/kg) or 75 mg/kg ketoconazole for three consecutive days.

Route of Administration: Intragastric

In Vitro Use Guide

The DENV-infected Huh-7 cells were treated with 30 or 40 uM of schisandrin A for 3 days. The RT-qPCR results revealed that schisandrin A can block the replication of the four serotypes of DENV in a concentration-dependent manner.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:09:10 UTC 2023` Edited by `admin` on `Sat Dec 16 11:09:10 UTC 2023`
Record UNII	74XQL5DO3S
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SCHISANDRIN A

Common Name

English

(+)-DEOXYSCHIZANDRIN

Common Name

English

DIBENZO(A,C)CYCLOOCTENE, 5,6,7,8-TETRAHYDRO-1,2,3,10,11,12-HEXAMETHOXY-6,7-DIMETHYL-, (6R,7S,12AR)-

Systematic Name

English

DEOXYSCHIZANDRIN

Common Name

English

SCHISANDRIN A (DEOXYSCHISANDRIN) (CONSTITUENT OF NORTHERN SCHISANDRA) [DSC]

Common Name

English

SCHIZANDRIN A

Common Name

English

WUWEIZISU A

Common Name

English

Schizandrin A [WHO-DD]

Common Name

English

DEOXYSCHISANDRIN

Common Name

English

Code System Code Type Description

EVMPD

SUB180108