KERACYANIN CATION

Possibly Marketed Outside US

First approved in 2015

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H31O15
Molecular Weight	595.526
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C([O+]=C4C=C(O)C=C(O)C4=C3)C5=CC=C(O)C(O)=C5)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

InChI

InChIKey=USNPULRDBDVJAO-FXCAAIILSA-O

InChI=1S/C27H30O15/c1-9-19(32)21(34)23(36)26(39-9)38-8-18-20(33)22(35)24(37)27(42-18)41-17-7-12-14(30)5-11(28)6-16(12)40-25(17)10-2-3-13(29)15(31)4-10/h2-7,9,18-24,26-27,32-37H,8H2,1H3,(H3-,28,29,30,31)/p+1/t9-,18+,19-,20+,21+,22-,23+,24+,26+,27+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C27H30O15
Molecular Weight	594.5181
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16744416 | https://www.ncbi.nlm.nih.gov/pubmed/11878815 | https://www.ncbi.nlm.nih.gov/pubmed/23364751 | https://www.ncbi.nlm.nih.gov/pubmed/16122862 | https://www.ncbi.nlm.nih.gov/pubmed/15373421 | https://www.ncbi.nlm.nih.gov/pubmed/21517858 | https://www.ncbi.nlm.nih.gov/pubmed/23768383

Keracyanin (antirrhinin) is the pigment originally isolated from the fruit of the cherry. The compound exerts potent antioxidant properties. It is able to inhibit host- and bacteria-derived proteinases. Dietary supplementation with purified keracyanin suppresses body weight gain in high-fat diet fed mice.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serum albumin 18 Target ID: CHEMBL3253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24930424	Binding Agent 1064
cell proliferation 28 Target ID: GO:0008283 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20155622	Inhibitor 8297
apoptotic process 48 Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20155622	Activator 1430
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11878815 \| https://www.ncbi.nlm.nih.gov/pubmed/23364751 \| https://www.ncbi.nlm.nih.gov/pubmed/16122862 \| https://www.ncbi.nlm.nih.gov/pubmed/15373421	Inhibitor 8297
Matrix metalloproteinase-1 8 Target ID: CHEMBL332 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21517858	Inhibitor 8297
Matrix metalloproteinase 9 20 Target ID: CHEMBL321 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21517858	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23768383	Primary	Preclinical	Unknown Approved Use Unknown
Night blindness 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6381579	Primary	Not Provided 504	Unknown Approved Use Unknown
Myopia 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6381579	Primary	Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Studies on anthocyanins. XXIV. Keracyanin, a pigment in the fire-red blooms of Canna generalis].	1954 Mar	13177118
Dose-modifying effect of a cyanidine chloride derivative, keracyanin, for uv irradiation of murine L fibroblasts cultured in vitro.	1979 Mar	441258
[Experimental study of the effects of cyaninoside chloride on collagen, and its potential value in ophthalmology].	1984	6085333

Patents

Sample Use Guides

In Vivo Use Guide

The results from a 12-week experiment show that consumption of purified mulberry anthocyanin cyanidin-3-O-rutinoside (keracyanin) of 40 or 200mg/kg can significantly inhibit body weight gain, reduce the resistance to insulin, lower the size of adipocytes, attenuate lipid accumulation and decrease the leptin secretion.

Route of Administration: Oral

In Vitro Use Guide

The effects of cyanidin-3-O-rutinoside (keracyanin), on the growth of RE-149 and RE-149 DHD cells were determined at concentrations ranging from 10–50 µg/ ml

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:04:45 GMT 2023` Edited by `admin` on `Sat Dec 16 11:04:45 GMT 2023`
Record UNII	OR49FC491X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

KERACYANIN CATION

Common Name

English

CYANIDIN-3-RUTINOSIDE

Common Name

English

CYANIDIN 3-.BETA.-D-O-RUTINOSIDE

Systematic Name

English

1-BENZOPYRYLIUM, 3-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-

Systematic Name

English

CYANIDIN 3-O-RUTINOSIDE

Systematic Name

English

KERACYANIN ION

Common Name

English

FLAVYLIUM, 3-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-3',4',5,7-TETRAHYDROXY-

Systematic Name

English

Code System Code Type Description

CAS

259813-55-3