MYRICITRIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H20O12
Molecular Weight	464.3763
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1O[C@@H](OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C4=CC(O)=C(O)C(O)=C4)[C@H](O)[C@H](O)[C@H]1O

InChI

InChIKey=DCYOADKBABEMIQ-OWMUPTOHSA-N

InChI=1S/C21H20O12/c1-6-14(26)17(29)18(30)21(31-6)33-20-16(28)13-9(23)4-8(22)5-12(13)32-19(20)7-2-10(24)15(27)11(25)3-7/h2-6,14,17-18,21-27,29-30H,1H3/t6-,14-,17+,18+,21-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C21H20O12
Molecular Weight	464.3763
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28751937 | https://www.ncbi.nlm.nih.gov/pubmed/21689712 | https://www.ncbi.nlm.nih.gov/pubmed/17070780

Myricitrin is a naturally occurring polyphenol hydroxy flavonoid. Myricitrin has a variety of beneficial properties, such as antiviral, antimicrobial, antinociceptive, and anticarcinogenic activities. In particular, myricitrin possesses stronger oxidative resistance and free radical scavenging activity than other flavonol rhamnosides or quercetin. Myricitrin showed antipsychotic-like effects in animal models at doses that did not induce catalepsy or alter locomotor activity, suggesting that myricitrin may be a potential drug treatment for the positive symptoms of schizophrenia.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Catechol O-methyltransferase 21 Target ID: CHEMBL2023 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24716406	Inhibitor 8297	0.5 µM [Ki]
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12972054	Inhibitor 8297
Protein kinase C alpha 20 Target ID: CHEMBL2567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16260583 \| https://www.ncbi.nlm.nih.gov/pubmed/21689712	Inhibitor 8297
Protein kinase C epsilon 4 Target ID: CHEMBL4366 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21689712 \| https://www.ncbi.nlm.nih.gov/pubmed/16260583	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17467689 https://www.ncbi.nlm.nih.gov/pubmed/17070780	Primary	Preclinical	Unknown Approved Use Unknown
Schizophrenia 298 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21689712	Palliative	Preclinical	Unknown Approved Use Unknown
Anxiety 267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19387830	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibition of HIV infection by flavanoids.	1993 Oct	8279812
Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds.	1994 Aug 3	7520698
Application of the electrotopological state index to QSAR analysis of flavone derivatives as HIV-1 integrase inhibitors.	1996 Dec	8987091
Inhibitory activity of flavonoids and tannins against HIV-1 protease.	2000 Sep	10993207
Anti-human immunodeficiency virus-type 1 activity of constituents from Juglans mandshurica.	2002 Aug	12214852
An unusual C6-C6" linked flavonoid from Miconia cabucu (Melastomataceae).	2007 Jul	17540417
Constituents and antiulcer effect of Alchornea glandulosa: activation of cell proliferation in gastric mucosa during the healing process.	2007 Mar	17329837
[A new flavonol glycoside from Baeckea Frutescens L].	2008 Oct	19127867
Isolated flavonoids against mammary tumour cells LM2.	2009 Jan-Feb	19323263
Hexaoxygenated flavonoids from Pteroxygonum giraldii.	2010 Feb	20334131
Gmelinoside I, a new flavonol glycoside from Limonium gmelinii.	2010 Jul	20734940
[Chemical constituents from Parthenocissus quinquefolia].	2010 Jun	20815210
[Studies on the chemical constituents of the root tube from Pteroxygonum giraldii].	2010 Nov	21434433
Assessment of DNA damage induced by extracts, fractions and isolated compounds of Davilla nitida and Davilla elliptica (Dilleniaceae).	2010 Sep 30	20692361
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.	2011 Dec 15	21872416
Inhibitory effects of myricitrin on oxidative stress-induced endothelial damage and early atherosclerosis in ApoE-/- mice.	2013 Aug 15	23639522
Protective effects of myricitrin against osteoporosis via reducing reactive oxygen species and bone-resorbing cytokines.	2014 Nov 1	25130202
Myricitrin exhibits antioxidant, anti-inflammatory and antifibrotic activity in carbon tetrachloride-intoxicated mice.	2015 Mar 25	25656916

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 5, 10, and 30 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

RAW264.7 cells were pretreated with 400 ug/ml myricitrin for 2 h or not and then were incubated with LPS (100 ng/ml) for 15 min. Noncytotoxic level of myricitrin inhibited p47phox which was transferred to the membrane and suppressed the interaction between p47phox and gp91phox.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:10:31 GMT 2023` Edited by `admin` on `Fri Dec 15 19:10:31 GMT 2023`
Record UNII	5Z0ZO61WPJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MYRICITRIN

Official Name

English

MYRICETIN 3-O-RHAMNOSIDE

Common Name

English

MYRICETIN 3-O-.ALPHA.-L-RHAMNOPYRANOSIDE

Common Name

English

3,3',4',5,5',7-HEXAHYDROXYFLAVONE, 3-RHAMNOSIDE

Common Name

English

MYRICITROSIDE

Common Name

English

MYRICETIN 3-O-.ALPHA.-L-RHAMNPYRONOSIDE

Common Name

English

MYRICITRINE

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-5,7-DIHYDROXY-2-(3,4,5-TRIHYDROXYPHENYL)-

Common Name

English

MYRICITRIN [INCI]

Common Name

English

NSC-19803

Code

English

MYRICETIN 3-O-RHAMNOPYRANOSIDE

Common Name

English

FEMA NO. 4491

Code

English

Code System Code Type Description

CAS

17912-87-7