MALVIDIN 3-GLUCOSIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H25O12.Cl
Molecular Weight	528.89
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
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@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(O)=CC(O)=C3

InChI

InChIKey=YDIKCZBMBPOGFT-DIONPBRTSA-N

InChI=1S/C23H24O12.ClH/c1-31-14-3-9(4-15(32-2)18(14)27)22-16(7-11-12(26)5-10(25)6-13(11)33-22)34-23-21(30)20(29)19(28)17(8-24)35-23;/h3-7,17,19-21,23-24,28-30H,8H2,1-2H3,(H2-,25,26,27);1H/t17-,19-,20+,21-,23-;/m1./s1

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	C23H24O12
Molecular Weight	492.4295
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.nexira.com/ru/ViNitrox%E2%84%A2-Healthy-sports-nutrition_16.html | https://www.ncbi.nlm.nih.gov/pubmed/28829368 | https://www.ncbi.nlm.nih.gov/pubmed/27935050 | https://www.ncbi.nlm.nih.gov/pubmed/25153881 | https://www.ncbi.nlm.nih.gov/pubmed/23796750

Malvidin-3-O-glucoside is a polyphenolic anthocyanin. Anthocyanins are flavonoids widely distributed in fruits and vegetables that exhibit antioxidative and anti-inflammatory bioactivities. Among other polyphenolic components, malvidin-3-glucoside is present in ViNitrox™ a natural dietary supplement from apple and grape, it offers a number of exceptional sports nutrition properties including enhanced and lasting performance.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Oxidative Stress 162 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27935050	Inhibitor 8504
inflammatory response 47 Target ID: GO:0006954 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25153881 \| https://www.ncbi.nlm.nih.gov/pubmed/23796750	Inhibitor 8504
Phosphodiesterase 5A 31 Target ID: CHEMBL1827 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15769121	Inhibitor 8504	35.4 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Fatigue 46 Sources: http://www.nexira.com/ru/ViNitrox%E2%84%A2-Healthy-sports-nutrition_16.html https://www.ncbi.nlm.nih.gov/pubmed/28829368	Primary		Approved 8583	ViNitrox Approved Use ViNitrox™ is a natural dietary supplement containing apple and grape polyphenols including proanthocyanidins (as catechins, B2 dimer), phenolic acids (as chlorogenic acids, gallic acids) and anthocyanins (as malvidin-3-glucoside). It offers a number of exceptional sports nutrition properties including enhanced and lasting performance.
Arthritis 87 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23796750	Primary		Preclinical	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
1.38 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11697443/	68.6 mg single, oral dose: 68.6 mg route of administration: Oral experiment type: SINGLE co-administered:		MALVIDIN 3-GLUCOSIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
288 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11697443/	68.6 mg single, oral dose: 68.6 mg route of administration: Oral experiment type: SINGLE co-administered:		MALVIDIN 3-GLUCOSIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

Doses

Dose	Population	Adverse events
117 mg 1 times / week multiple, oral Highest studied dose Dose: 117 mg, 1 times / week Route: oral Route: multiple Dose: 117 mg, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/11697443/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/11697443/	Sources: https://pubmed.ncbi.nlm.nih.gov/11697443/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	inhibitor 2507 substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 BCRP 910	CYP1A2 1197 CYP2C19 1119

Drug as perpetrator

Target	Modality	Activity
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/34959345/	no
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/19922539/	yes [IC50 43 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/19357792/ \| https://www.zora.uzh.ch/id/eprint/32529/9/manuscript.pdf	yes [IC50 70 uM]

Drug as victim

Target	Modality	Activity
CYP1A2 1197	substrate 4014 Sources: http://thesciencepublishers.com/science_letters/v10i1abstract6.html	no
CYP2C19 1119	substrate 4014 Sources: http://thesciencepublishers.com/science_letters/v10i1abstract6.html	no
CYP2C9 1193	substrate 4014 Sources: http://thesciencepublishers.com/science_letters/v10i1abstract6.html	no
CYP2D6 1388	substrate 4014 Sources: http://thesciencepublishers.com/science_letters/v10i1abstract6.html	no
CYP3A4 1946	substrate 4014 Sources: http://thesciencepublishers.com/science_letters/v10i1abstract6.html	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: http://thesciencepublishers.com/science_letters/v10i1abstract6.html

PubMed

Title	Date	PubMed
Stilbenes and anthocyanins reduce stress signaling in BV-2 mouse microglia.	2013-06-26	23731018
Malvidin-3-glucoside protects endothelial cells up-regulating endothelial NO synthase and inhibiting peroxynitrite-induced NF-kB activation.	2012-09-30	22959858
Bioassay-guided separation of an alpha-amylase inhibitor anthocyanin from Vaccinium arctostaphylos berries.	2010-12-09	21138057
Antioxidant activity of wine pigments derived from anthocyanins: hydrogen transfer reactions to the dpph radical and inhibition of the heme-induced peroxidation of linoleic acid.	2009-07-08	19566083
Anthocyanins in aged blueberry-fed rats are found centrally and may enhance memory.	2005-04	16053243
In vitro inhibition of human cGMP-specific phosphodiesterase-5 by polyphenols from red grapes.	2005-03-23	15769121
The anthocyanidins cyanidin and delphinidin are potent inhibitors of the epidermal growth-factor receptor.	2001-02	11262056

Patents

Sample Use Guides

In Vivo Use Guide

Vinitrox™, supplied by Nexira (France) is a combination of specific profile polyphenols from grape and apple. Vinitrox™ is a purified extract with low lipids, fibers and proteins content (respectively 0.5%, 1.4% and 5.5%) and more than 60% of total polyphenols (Folin method—expressed as gallic acid equivalent) with antioxidant properties demonstrated by ORAC value (12,000 μMtrolox equivalent per gram of ingredient). The main polyphenol classes are proanthocyanidins (as catechins, B2 dimer), phenolic acids (as chlorogenic acids, gallic acids) and anthocyanins (as malvidin-3-glucoside). Nexira’s latest clinical study on 50 athletes, 25-45 years old, demonstrated that under intensive effort, 500 mg/day of ViNitrox™ improves physical capabilities: increases physical training time by 10%, delays the fatigue barrier by 13%.

Route of Administration: Oral

In Vitro Use Guide

1 mg/mL blueberry extract significantly reduced LPS-induced nitric oxide release in BV-2 mouse microglia; this concentration of blueberry extract contains 2.6 μM malvidin-3-O-glucoside, but when malvidin-3-O-glucoside was tested individually, 20 μM was necessary to observe a significant reduction in nitric oxide release.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:25:25 GMT 2025` Edited by `admin` on `Mon Mar 31 20:25:25 GMT 2025`
Record UNII	B34F52D7NB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-70532

Preferred Name

English

MALVIDIN 3-GLUCOSIDE

Common Name

English

1-BENZOPYRYLIUM, 3-(.BETA.-D-GLUCOPYRANOSYLOXY)-5,7-DIHYDROXY-2-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-, CHLORIDE (1:1)

Common Name

English

ENIN

Common Name

English

OENIN

Common Name

English

MALVIDIN-3-O-GLUCOSIDE

Common Name

English

MALVINIDIN 3-GLUCOSIDE

Common Name

English

Code System Code Type Description

WIKIPEDIA

OENIN