EPIPINORESINOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H22O6
Molecular Weight	358.3851
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CO[C@H](C3=CC(OC)=C(O)C=C3)[C@@]1([H])CO[C@H]2C4=CC(OC)=C(O)C=C4

InChI

InChIKey=HGXBRUKMWQGOIE-WZBLMQSHSA-N

InChI=1S/C20H22O6/c1-23-17-7-11(3-5-15(17)21)19-13-9-26-20(14(13)10-25-19)12-4-6-16(22)18(8-12)24-2/h3-8,13-14,19-22H,9-10H2,1-2H3/t13-,14-,19-,20+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C20H22O6
Molecular Weight	358.3851
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25555357 | https://www.ncbi.nlm.nih.gov/pubmed/24963714 | https://books.google.ru/books?id=7eVUAQAAQBAJ&pg=PA325&lpg=PA325&dq=EPIPINORESINOL retrieved from Medicinal Plants in Australia Volume 4: An Antipodean Apothecary By Cheryll Williams, p. 325 | https://www.ncbi.nlm.nih.gov/pubmed/28384606

Epipinoresinol is an important component of the medicinal herb Eucommia ulmoides, which has a substantial reputation as an effective antihypertensive remedy. Epipinoresinol (EPR) belongs to the group of furofuran-type lignans consisting of two phenylpropane units. (+)-epipinoresinol exhibited antiplatelet aggregation activity. It also exhibited inhibitory effects on nitric oxide production. Epipinoresinol possess antiproliferative activity.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
nitric oxide biosynthetic process 17 Target ID: GO:0006809 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24963714	Inhibitor 8297	39.5 µM [IC50]
Peroxisome proliferator-activated receptor delta 29 Target ID: CHEMBL3979 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22381047	Agonist 2678	49.5 µM [EC50]
Peroxisome proliferator-activated receptor gamma 111 Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22381047	Agonist 2678	58.6 µM [EC50]
Peroxisome proliferator-activated receptor 5 Target ID: CHEMBL3559683 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22381047	Agonist 2678	10.3 µM [EC50]
platelet aggregation 76 Target ID: GO:0070527 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25555357	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: Williams, C. (2013) Medicinal Plants in Australia, v.4, page 325, retrieved from: https://books.google.ru/books?id=7eVUAQAAQBAJ	Primary		Not Provided 504	Unknown Approved Use Unknown
Colon cancer 62 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28384606	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Phenolic constituents from Parakmeria yunnanensis and their anti-HIV-1 activity.	2013 Oct	23444043
Lignans and aromatic glycosides from Piper wallichii and their antithrombotic activities.	2015 Mar 13	25555357
Optimized conversion of antiproliferative lignans pinoresinol and epipinoresinol: Their simultaneous isolation and identification by centrifugal partition chromatography and high performance liquid chromatography.	2017 May 1	28384606

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Epipinoresinol inhibited LPS-induced NO production in macrophage RAW 264.7 cells with IC50 value of 39.5 uM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 14:04:47 GMT 2023` Edited by `admin` on `Sat Dec 16 14:04:47 GMT 2023`
Record UNII	6YKG9JJC1S
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPIPINORESINOL

Common Name

English

(+)-EPIPINORESINOL

Common Name

English

PHENOL, 4,4'-(TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS(2-METHOXY-, (1S-(1.ALPHA.,3A.ALPHA.,4.BETA.,6A.ALPHA.))-

Systematic Name

English

PHENOL, 4,4'-(3A.BETA.,4,6,6A.BETA.-TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1.ALPHA.,4.BETA.-DIYL)BIS(2-METHOXY-

Systematic Name

English

PHENOL, 4,4'-((1R,3AR,4S,6AR)-TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS(2-METHOXY-

Systematic Name

English

4,4'-((1R,3AR,4S,6AR)-TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS(2-METHOXYPHENOL)

Systematic Name

English

EPI-PINORESINOL

Common Name

English

Code System Code Type Description

PUBCHEM

637584

Created by admin on Sat Dec 16 14:04:47 GMT 2023 , Edited by admin on Sat Dec 16 14:04:47 GMT 2023

PRIMARY

FDA UNII

6YKG9JJC1S

Created by admin on Sat Dec 16 14:04:47 GMT 2023 , Edited by admin on Sat Dec 16 14:04:47 GMT 2023

PRIMARY

CAS

24404-50-0

Created by admin on Sat Dec 16 14:04:47 GMT 2023 , Edited by admin on Sat Dec 16 14:04:47 GMT 2023

PRIMARY

CHEBI

132821

Created by admin on Sat Dec 16 14:04:47 GMT 2023 , Edited by admin on Sat Dec 16 14:04:47 GMT 2023

PRIMARY

Details

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

PubMed

Patents

Sample Use Guides