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Details

Stereochemistry ACHIRAL
Molecular Formula C15H11O6.Cl
Molecular Weight 322.697
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYANIDIN CHLORIDE

SMILES

[Cl-].OC1=CC(O)=C2C=C(O)C(=[O+]C2=C1)C3=CC(O)=C(O)C=C3

InChI

InChIKey=COAWNPJQKJEHPG-UHFFFAOYSA-N
InChI=1S/C15H10O6.ClH/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);1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C15H10O6
Molecular Weight 286.2363
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency
3.0 µM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

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
Record UNII
2G4283G96U
Record Status Validated (UNII)
Record Version