CYANIDIN CATION

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H11O6
Molecular Weight	287.2442
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC2=[O+]C(C3=CC=C(O)C(O)=C3)=C(O)C=C2C(O)=C1

InChI

InChIKey=VEVZSMAEJFVWIL-UHFFFAOYSA-O

InChI=1S/C15H10O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-6H,(H4-,16,17,18,19,20)/p+1

HIDE SMILES / InChI

Molecular Formula	C15H10O6
Molecular Weight	286.2363
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/28788070 | https://www.ncbi.nlm.nih.gov/pubmed/28771720 | https://www.ncbi.nlm.nih.gov/pubmed/28722162

Cyanidin is a natural anthocyanidin present in fruits and vegetables, attenuates the development of several diseases, including asthma, diabetes, atherosclerosis, and cancer, through its anti-inflammatory effects. Its mechanism of action is still undefined, but it was revealed that cyanidin specifically recognizes an IL-17A binding site in the IL-17A receptor subunit (IL-17RA) and inhibits the IL-17A/IL-17RA interaction and thus can be used as a drug for the treatment of IL-17A-dependent inflammatory diseases and cancer. In addition, cyanidin was capable of inhibiting osteoclast formation and thus might have therapeutic potential for osteolytic diseases.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Interleukin-17 receptor A 2 Target ID: Q96F46 Gene ID: 23765.0 Gene Symbol: IL17RA Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28223414	Binding Agent 1064		3.0 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Osteolytic diseases 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28771720	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Cyanidin Stimulates Insulin Secretion and Pancreatic β-Cell Gene Expression through Activation of l-type Voltage-Dependent Ca(2+) Channels.	2017 Jul 28	28788070
Cyanidin Chloride inhibits ovariectomy-induced osteoporosis by suppressing RANKL-mediated osteoclastogenesis and associated signaling pathways.	2018 Mar	28771720

Patents

Sample Use Guides

In Vivo Use Guide

in mice: To examine the effect of A18 (also called cyanidin) on IL-17A–induced epidermal cell proliferation, it was intradermally injected the ears of female WT C57BL/6 mice with PBS or with IL-17A alone or together with A18 for six consecutive days. After the injections, the mice treated with IL-17 alone exhibited IL-17A–dependent epidermal hyperplasia, whereas the mice treated with both IL-17 and A18 exhibited reduced hyperplasia.

Route of Administration: Other

In Vitro Use Guide

It was studied the mechanisms of cyanidin for stimulatory insulin secretion from pancreatic β-cells. Cyanidin (1–300 µM) stimulated insulin secretion and cyanidin (80 to 300 µM) increased intracellular Ca2+ signals in a concentration-dependent manner. The Ca2+ signals were abolished by nimodipine, an l-type voltage-dependent Ca2+ channel (VDCC) blocker or under extracellular Ca2+ free conditions. Stimulation of cells with cyanidin activated currents typical for VDCCs and up-regulated the expression of glucose transporter 2 (GLUT2), Kir6.2, and Cav1.2 genes.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:06:44 GMT 2023` Edited by `admin` on `Sat Dec 16 10:06:44 GMT 2023`
Record UNII	7732ZHU564
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CYANIDIN CATION

Common Name

English

3,5,7,3',4'-PENTAHYDROXYFLAVYLIUM

Systematic Name

English

CYANIDIN

Common Name

English

FLAVYLIUM, 3,3',4',5,7-PENTAHYDROXY-

Systematic Name

English

CYANIDINE

Common Name

English

CYANIDIN ION

Common Name

English

2-(3,4-DIHYDROXYPHENYL) CHROMENYLIUM-3,5,7-TRIOL

Systematic Name

English

1-BENZOPYRYLIUM, 2-(3,4-DIHYDROXYPHENYL)-3,5,7-TRIHYDROXY-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C68444