VERBENALIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H24O10
Molecular Weight	388.3665
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12[C@@H](C)CC(=O)[C@]1([H])C(=CO[C@H]2O[C@]3([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(=O)OC

InChI

InChIKey=HLXRWTJXGMHOFN-XJSNKYLASA-N

InChI=1S/C17H24O10/c1-6-3-8(19)11-7(15(23)24-2)5-25-16(10(6)11)27-17-14(22)13(21)12(20)9(4-18)26-17/h5-6,9-14,16-18,20-22H,3-4H2,1-2H3/t6-,9+,10+,11-,12+,13-,14+,16-,17-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C17H24O10
Molecular Weight	388.3665
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26871971
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19904996

Verbenalin is an iridoid glycoside, and an alkaloid as well, found in Verbena officinalis. Verbenalin has demonstrated cardioprotection against experimental myocardial ischemic injury. It attenuated hypoxia-induced cytotoxicity significantly in H9c2 cells in a concentration-dependent manner. Treatment of H9c2 cells with Verbenalin blocked the reduction of expression of phospho-CREB and phospho-Akt in a hypoxic condition. Verbenalin can protect myocardial function in rats during myocardial I/R injury, suggesting the therapeutic potential of Verbenalin against myocardial I/R injury. Verbenalin also exhibited significant anti-HCV entry and anti-infectivity activities.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Hepatitis C virus 22 Target ID: CHEMBL379 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19904996	Inhibitor 8297
Hypoxia-induced cytotoxicity, H9c2 cells 1 Target ID: Hypoxia-induced cytotoxicity, H9c2 cells Sources: https://www.ncbi.nlm.nih.gov/pubmed/26871971	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Prostatitis 25 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26858560	Primary	Preclinical	Unknown Approved Use Unknown
Myocardial ischemia 15 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26871971	Primary	Preclinical	Unknown Approved Use Unknown
Hepatitis C 42 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19904996	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

Rats: Treatment of rats with Verbenalin (30 mg/kg, iv) protected them from myocardial I/R injury

Route of Administration: Intravenous

In Vitro Use Guide

Verbenalin gave 21.9% inhibition against HCVpp infection at a concentration of 20 ug/mL. Inhibition activity against HCVpp infection was further improved to 43.4%, respectively, after 4h enzyme incubation process.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:50:55 UTC 2023` Edited by `admin` on `Sat Dec 16 08:50:55 UTC 2023`
Record UNII	71B68181Z6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VERBENALIN

Common Name

English

VERBENALIN [MI]

Common Name

English

CORNIN

Common Name

English

NSC-118055

Code

English

CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-7-METHYL-5-OXO-, METHYL ESTER, (1S,4AS,7S,7AR)-

Systematic Name

English

VERBENALOSIDE

Common Name

English

Code System Code Type Description

CAS

548-37-8