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=CC(O)=CC(O)=C3C=C2O

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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

Molecular Formula	C17H14O7
Molecular Weight	330.2889
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/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 160 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 8297
inflammatory response 47 Target ID: GO:0006954 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24333549	Inhibitor 8297
Phosphodiesterase 5A 30 Target ID: CHEMBL1827 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15769121	Inhibitor 8297	24.9 µM [IC50]
apoptotic process 48 Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15964118	Activator 1430
cell proliferation 28 Target ID: GO:0008283 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15964118	Inhibitor 8297
ATP-binding cassette sub-family G member 2 16 Target ID: CHEMBL5393 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19922539	Modulator 828

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 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15964118	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antioxidant activity of anthocyanins and their aglycons.	2003 Jan 29	12537433
In vitro inhibition of human cGMP-specific phosphodiesterase-5 by polyphenols from red grapes.	2005 Mar 23	15769121
Berry anthocyanins and anthocyanidins exhibit distinct affinities for the efflux transporters BCRP and MDR1.	2009 Dec	19922539
Inhibitory effect of Malvidin on TNF-α-induced inflammatory response in endothelial cells.	2014 Jan 15	24333549
Malvidin Protects WI-38 Human Fibroblast Cells Against Stress-induced Premature Senescence.	2016 Mar	27051647

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:50:29 GMT 2023` Edited by `admin` on `Fri Dec 15 17:50:29 GMT 2023`
Record UNII	GL5KGZ4D8U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MALVIDIN CHLORIDE

Common 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

NSC-94526

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C68444