GENTIOPICRIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H20O9
Molecular Weight	356.3246
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]3(O[C@@H]1OC=C2C(=O)OCC=C2[C@H]1C=C)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O

InChI

InChIKey=DUAGQYUORDTXOR-GPQRQXLASA-N

InChI=1S/C16H20O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2-3,6-7,10-13,15-20H,1,4-5H2/t7-,10-,11-,12+,13-,15+,16+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C16H20O9
Molecular Weight	356.3246
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23419353 | https://www.ncbi.nlm.nih.gov/pubmed/15537172 | https://www.ncbi.nlm.nih.gov/pubmed/27394986 | https://www.ncbi.nlm.nih.gov/pubmed/22521634 | https://www.ncbi.nlm.nih.gov/pubmed/24584520

Gentiopicrin is a naturally occurring iridoid glycoside. It is a bioactive component of gentian species of medical plants. It has proved to be the strongest inhibitor of myeloperoxidase. It could be absorbed rapidly in mice, but with a low bioavailability, and could distribute to tissues extensively. Gentiopicrin has been reported to be effective against inflammatory conditions such as rheumatoid arthritis, liver illness, fever, digestive and intestinal disorders. Gentiopicrin treatment can exert anti-inflammatory effects on experimental acute colitis through attenuating the expression levels of TNF-α, IL-1β, IL-6, iNOS and COX-2, and it may present the therapeutic potential in the treatment of colitis. The drug inhibits reserpine-induced pain/depression dyad by downregulating GluN2B receptors in the amygdala. Gentiopicrin injection was approved by SFDA for the treatment of acute jaundice and chronic active hepatitis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 2A6 16 Target ID: CHEMBL5282 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23419353	Inhibitor 8297
Cytochrome P450 2E1 25 Target ID: P05181 Gene ID: 1571.0 Gene Symbol: CYP2E1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23419353	Inhibitor 8297
Myeloperoxidase 6 Target ID: CHEMBL2439 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22521634	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Acute hepatitis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23419353	Primary	Approved 8429	Unknown Approved Use Unknown
Colitis 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27394986	Primary	Preclinical	Unknown Approved Use Unknown
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27175624 https://www.ncbi.nlm.nih.gov/pubmed/24584520	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Determination gentiopicrin in biyanqingdu granulae by SPE-HPLC].	2005 Jun	16209272
[Inhibition of extracts from 17 Chinese herbs on periodontal pathogenic microbes].	2006 Aug	16955176
[Determination of ginsenoside rd in human plasma by LC/MS/MS].	2006 Sep	17212051
[Preparative separation of gentiopicrin from Radix Gentianae by high-speed counter-current chromatography with macroporous resin].	2007 Dec	18338594
Gentiopicrin-producing endophytic fungus isolated from Gentiana macrophylla.	2009 Aug	19200701
Antimicrobial activity of Gentiana lutea L. extracts.	2009 May-Jun	19678535
Anti-apoptotic activity of gentiopicroside in D-galactosamine/lipopolysaccharide-induced murine fulminant hepatic failure.	2010 Oct 6	20558151

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 200, 100, and 50mg/kg once a day for 7days

Route of Administration: Oral

In Vitro Use Guide

50, 500, and 1,500 ug/mL of gentiopicrin exhibited no significant toxicity to chondrocytes (P>0.05) after 24h.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:41:06 UTC 2023` Edited by `admin` on `Fri Dec 15 19:41:06 UTC 2023`
Record UNII	0WE09Z21RC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GENTIOPICRIN

Common Name

English

NSC-606402

Code

English

GENTIOPICRIN [MI]

Common Name

English

GENTIOPICROSIDE

Common Name

English

(5R,6S)-5-ETHENYL-6-(.BETA.-D-GLUCOPYRANOSYLOXY)-5,6-DIHYDRO-1H,3H-PYRANO(3,4-C)PYRAN-1-ONE

Common Name

English

Code System Code Type Description

MERCK INDEX

m5702