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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 of KERACYANIN CATION

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

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

Willstatter, R.|Zollinger, F.H.
2
Sources: Willstiitter and Zollinger (1916). Liebig's Ann. 412, 164.
Curator's Comment: refrence retrieved from https://www.ncbi.nlm.nih.gov/pubmed/16744416

Approval Year

2015
471
Targets

Targets

Primary TargetPharmacologyConditionPotency
Binding Agent
1064
Inhibitor
8297
Activator
1430
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Not Provided
504
Unknown

Approved Use

Unknown
Primary
Not Provided
504
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Studies on anthocyanins. XXIV. Keracyanin, a pigment in the fire-red blooms of Canna generalis].
1954 Mar
Dose-modifying effect of a cyanidine chloride derivative, keracyanin, for uv irradiation of murine L fibroblasts cultured in vitro.
1979 Mar
[Experimental study of the effects of cyaninoside chloride on collagen, and its potential value in ophthalmology].
1984
[Effects of cyaninoside chloride and Heleniene on mesopic and scotopic vision in myopia and night blindness].
1984
Oral flavonoids, chromocarb diethylamine salt and cyaninosides chloride, to eliminate lipoperoxidation postvitrectomy.
2002 Jan
Inhibition of malonaldehyde formation in oxidized calf thymus DNA with synthetic and natural antioxidants.
2004 Sep 8
Formation and inhibition of genotoxic malonaldehyde from DNA oxidation controlled with EDTA.
2006 Feb
Black raspberry components inhibit proliferation, induce apoptosis, and modulate gene expression in rat esophageal epithelial cells.
2009
Interaction between gliadins and anthocyan derivatives.
2011 Dec 1
Inhibition of host- and bacteria-derived proteinases by natural anthocyanins.
2011 Oct
Separation and identification of anthocyanin extracted from mulberry fruit and the pigment binding properties toward human serum albumin.
2014 Jul 16
Patents

Patents

20050002865
228
20090098268
2

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 UTC 2023
Edited
by admin
on Sat Dec 16 11:04:45 UTC 2023
Record UNII
OR49FC491X
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Sat Dec 16 11:04:45 UTC 2023 , Edited by admin on Sat Dec 16 11:04:45 UTC 2023
SUPERSEDED
EPA CompTox
DTXSID401313656
Created by admin on Sat Dec 16 11:04:45 UTC 2023 , Edited by admin on Sat Dec 16 11:04:45 UTC 2023
PRIMARY
CHEBI
58546
Created by admin on Sat Dec 16 11:04:45 UTC 2023 , Edited by admin on Sat Dec 16 11:04:45 UTC 2023
PRIMARY
CHEBI
28064
Created by admin on Sat Dec 16 11:04:45 UTC 2023 , Edited by admin on Sat Dec 16 11:04:45 UTC 2023
PRIMARY
CAS
28338-59-2
Created by admin on Sat Dec 16 11:04:45 UTC 2023 , Edited by admin on Sat Dec 16 11:04:45 UTC 2023
PRIMARY
PUBCHEM
441674
Created by admin on Sat Dec 16 11:04:45 UTC 2023 , Edited by admin on Sat Dec 16 11:04:45 UTC 2023
PRIMARY
FDA UNII
OR49FC491X
Created by admin on Sat Dec 16 11:04:45 UTC 2023 , Edited by admin on Sat Dec 16 11:04:45 UTC 2023
PRIMARY
WIKIPEDIA
Cyanidin 3-rutinoside
Created by admin on Sat Dec 16 11:04:45 UTC 2023 , Edited by admin on Sat Dec 16 11:04:45 UTC 2023
PRIMARY
Related Record Type Details
HIBISCUS SABDARIFFA FLOWER
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
Structure of KERACYANIN CATION
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