VISNAGIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H10O4
Molecular Weight	230.2161
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C2C(=O)C=C(C)OC2=CC3=C1C=CO3

InChI

InChIKey=NZVQLVGOZRELTG-UHFFFAOYSA-N

InChI=1S/C13H10O4/c1-7-5-9(14)12-11(17-7)6-10-8(3-4-16-10)13(12)15-2/h3-6H,1-2H3

HIDE SMILES / InChI

Molecular Formula	C13H10O4
Molecular Weight	230.2161
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27936681
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25504881 | https://www.ncbi.nlm.nih.gov/pubmed/8691424 | https://www.ncbi.nlm.nih.gov/pubmed/21116788 | https://www.ncbi.nlm.nih.gov/pubmed/8202556

Visnagin is furanochromone and one of the main compounds of Ammi visnaga L. (syn. Khella) that can be frequently found in ethnomedical formulations in Asia and the Middle East. Visnagin possess analgesic properties due to its calcium channel blocking properties and act in an anti-inflammatory manner by inhibiting AP-1 and NF-κB signaling.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adenosine A3 receptor 24 Target ID: CHEMBL256 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8691424	Antagonist 2778		60.0 µM [Ki]
Voltage-gated L-type calcium channel 92 Target ID: CHEMBL2095229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8202556	Blocker 537

Conditions

Condition	Modality	Targets	Highest Phase	Product
Angina pectoris 106 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13287559	Primary		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Synthesis and biological activities of flavonoid derivatives as A3 adenosine receptor antagonists.	1996 Jun 7	8691424
Furanochromone radical cations: generation, characterization and interaction with DNA.	2001 Jul 2	11429200
Determination of khellin and visnagin in Ammi visnaga fruits by capillary electrophoresis.	2002 Apr 19	12058914
A new synthesis of oxadiazole, thiazolidinone, N-phthalimidoamino carbonyl and arylidene derivatives with potential antimicrobial activity.	2002 Jun	12210767
Epoxidation of some natural furocoumarins and furochromones using gamma-ray.	2002 May-Jun	12197416
Photosynthesis of furocoumarin- and furochromone-types potential intercalative alkylating and oxidizing agents of DNA through photooxidations using gamma-ray.	2002 Nov-Dec	12577512
Effect of psoralens on Fenton-like reaction generating reactive oxygen species.	2003	12400092
Stimulation of furanochromone accumulation in callus cultures of Ammi visnaga L. by addition of elicitors.	2003 Aug	12967041
Fluorometric determination of khellin in human urine and serum by high-performance liquid chromatography using postcolumn photoirradiation.	2003 Jul	12880095
The chemical investigations on the ripe fruits of Ammi visnaga (Lam.) Lamarck growing in Turkey.	2004 Apr	14984092
Nanosecond time-resolved infrared studies of visnagin and khellin triplets and radical ions.	2005 Oct 20	16833259
Ultraviolet photoionization of the photosensitizers khellin and visnagin in aqueous solution and in micelles: one-photon ionization is a minor process.	2006 Mar	16520866
A new steroid glycoside and furochromones from Cyperus rotundus L.	2007 Apr	17479423
Synthesis of 6- and 9-alkylaminomethyl furoflavones as gastroprotective agents.	2007 Aug	17346862
Determination of visnagin in rat plasma by liquid chromatography with tandem mass spectrometry and its application to in vivo pharmacokinetic studies.	2009 Mar 1	19188097
An aqueous extract of Ammi visnaga fruits and its constituents khellin and visnagin prevent cell damage caused by oxalate in renal epithelial cells.	2010 Jul	20036111
Anti-inflammatory effect of visnagin in lipopolysaccharide-stimulated BV-2 microglial cells.	2010 Nov	21116788
Neuroprotective Effect of Visnagin on Kainic Acid-induced Neuronal Cell Death in the Mice Hippocampus.	2010 Oct	21165322

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 25 mg/kg i.v. single dose.

Route of Administration: Intravenous

In Vitro Use Guide

Neonatal rat cardiomyocytes were used for activity evaluation. Neonatal rat cardiomyocytes and HL1 cells were stained with fluorescent Annexin V (Roche) and were live imaged after being treated with doxorubicin (1-50mkM), visnagin and diphenylurea for the indicated amounts of time. Apoptosis indices were quantified as percentage of AnnexinV positive cells.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:52:39 GMT 2023` Edited by `admin` on `Fri Dec 15 18:52:39 GMT 2023`
Record UNII	P64438MLBW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VISNAGIN

Common Name

English

VISNAGIN [MI]

Common Name

English

NSC-100593

Code

English

VISNAGIDIN

Common Name

English

DESMETHOXYKHELLIN

Common Name

English

5-METHOXY-2-METHYLFURANOCHROMONE

Common Name

English

4-METHOXY-7-METHYL-5H-FURO(3,2-G)(1)BENZOPYRAN-5-ONE

Systematic Name

English

Code System Code Type Description

CAS

82-57-5