MALVIDIN CHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H15O7.Cl
Molecular Weight	366.75
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Cl-].COC1=CC(=CC(OC)=C1O)C2=[O+]C3=C(C=C2O)C(O)=CC(O)=C3

InChI

InChIKey=KQIKOUUKQBTQBE-UHFFFAOYSA-N

InChI=1S/C17H14O7.ClH/c1-22-14-3-8(4-15(23-2)16(14)21)17-12(20)7-10-11(19)5-9(18)6-13(10)24-17;/h3-7H,1-2H3,(H3-,18,19,20,21);1H

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27051647 | https://www.ncbi.nlm.nih.gov/pubmed/24333549 | https://www.ncbi.nlm.nih.gov/pubmed/19922539 | https://www.ncbi.nlm.nih.gov/pubmed/12537433 | https://www.ncbi.nlm.nih.gov/pubmed/15964118 | https://www.ncbi.nlm.nih.gov/pubmed/15769121

Malvidin is a polyphenolic anthocyanin. Anthocyanins are flavonoids widely distributed in fruits and vegetables. Malvidin exhibits antiproliferative, antioxidant and anti-inflammatory bioactivities. It is able to inhibit cGMP-specific phosphodiesterase-5. Malvidin exhibited bimodal activities serving as breast cancer resistance protein (BCRP) substrate at low concentrations and, at higher concentrations, as BCRP inhibitor.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Oxidative Stress 162 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27051647 \| https://www.ncbi.nlm.nih.gov/pubmed/27445688 \| https://www.ncbi.nlm.nih.gov/pubmed/12537433	Inhibitor 8504
inflammatory response 47 Target ID: GO:0006954 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24333549	Inhibitor 8504
Phosphodiesterase 5A 31 Target ID: CHEMBL1827 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15769121	Inhibitor 8504	24.9 µM [IC50]
apoptotic process 51 Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15964118	Activator 1447
cell proliferation 28 Target ID: GO:0008283 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15964118	Inhibitor 8504
ATP-binding cassette sub-family G member 2 16 Target ID: CHEMBL5393 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19922539	Modulator 846

Conditions

Condition	Modality	Targets	Highest Phase	Product
Stroke 144 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27445688	Primary		Preclinical	Unknown Approved Use Unknown
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15964118	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Malvidin Protects WI-38 Human Fibroblast Cells Against Stress-induced Premature Senescence.	2016-03	27051647
Malvidin's Effects on Rat Pial Microvascular Permeability Changes Due to Hypoperfusion and Reperfusion Injury.	2016	27445688
Inhibitory effect of Malvidin on TNF-α-induced inflammatory response in endothelial cells.	2014-01-15	24333549
Berry anthocyanins and anthocyanidins exhibit distinct affinities for the efflux transporters BCRP and MDR1.	2009-12	19922539
In vitro inhibition of human cGMP-specific phosphodiesterase-5 by polyphenols from red grapes.	2005-03-23	15769121
Antioxidant activity of anthocyanins and their aglycons.	2003-01-29	12537433

Patents

Sample Use Guides

In Vivo Use Guide

rats: i.v. malvidin, 9 or 18 mg/kg b.w.

Route of Administration: Intravenous

In Vitro Use Guide

At a concentration of 5 microM of malvidin a significant decrease of phosphorylated ERK1 and ERK2 (ERK, extracellular regulated kinase) in HT29 cells was observed. The release of cells, synchronised in the G(2)/M-phase of the cell cycle by nocodazole treatment, was effectively blocked in the presence of 1 microM malvidin.

Name

Type

Language

MALVIDIN CHLORIDE

Common Name

English

NSC-94526

Preferred Name

English

PRIMULIDIN

Common Name

English

3,4',5,7-TETRAHYDROXY-3',5'-DIMETHOXY-2-PHENYLBENZOPYRYLIUM CHLORIDE

Common Name

English

MALVIDIN

Common Name

English

3,4',5,7-TETRAHYDROXY-3',5'-DIMETHOXYFLAVYLIUM CHLORIDE

Systematic Name

English

MALVIDIN CHLORIDE [MI]

Common Name

English

SYRINGIDIN

Common Name

English

ENIDIN

Common Name

English

3,5,7-TRIHYDROXY-2-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-1-BENZOPYRYLIUM CHLORIDE (1:1)

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C68444