KERACYANIN

Possibly Marketed Outside US

First approved in 2015

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H31O15.Cl
Molecular Weight	630.979
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Cl-].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=ADZHXBNWNZIHIX-XYGAWYNKSA-N

InChI=1S/C27H30O15.ClH/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);1H/t9-,18+,19-,20+,21+,22-,23+,24+,26+,27+;/m0./s1

HIDE SMILES / InChI

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
Oral flavonoids, chromocarb diethylamine salt and cyaninosides chloride, to eliminate lipoperoxidation postvitrectomy.	2002 Jan	11878815
Black raspberry components inhibit proliferation, induce apoptosis, and modulate gene expression in rat esophageal epithelial cells.	2009	20155622
Inhibition of host- and bacteria-derived proteinases by natural anthocyanins.	2011 Oct	21517858
Separation and identification of anthocyanin extracted from mulberry fruit and the pigment binding properties toward human serum albumin.	2014 Jul 16	24930424

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

Name

Type

Language

KERACYANIN

Official Name

English

MERALOP

Brand Name

English

keracyanin [INN]

Common Name

English

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

Common Name

English

KERACYANIN [MART.]

Common Name

English

ANTHOCYANIN A2

Common Name

English

CYANIDIN 3-RHAMNOGLUCOSIDE

Common Name

English

SAMBUCIN

Common Name

English

MERALOPS

Brand Name

English

KERACYANIN CHLORIDE

Common Name

English

Keracyanin [WHO-DD]

Common Name

English

CYANIDIN CHLORIDE 3-RHAMNOGLUCOSIDE [MI]

Common Name

English

ANTIRRHININ

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C275