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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 of KERACYANIN

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
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
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Inhibition of host- and bacteria-derived proteinases by natural anthocyanins.
2011 Oct
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 17:02:36 GMT 2023
Edited
by admin
on Sat Dec 16 17:02:36 GMT 2023
Record UNII
V0N2VMB4FV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
KERACYANIN
INN   MART.   WHO-DD  
INN  
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
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
NCI_THESAURUS C1745
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
242-528-6
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
PRIMARY
INN
3580
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
PRIMARY
WIKIPEDIA
ANTIRRHININ
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
PRIMARY
ChEMBL
CHEMBL505251
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
PRIMARY
MERCK INDEX
m3947
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
PRIMARY Merck Index
RXCUI
28165
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
ALTERNATIVE
EVMPD
SUB77256
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
PRIMARY
NCI_THESAURUS
C81330
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
PRIMARY
SMS_ID
100000082847
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
PRIMARY
CHEBI
16726
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
PRIMARY
RXCUI
236274
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
PRIMARY
FDA UNII
V0N2VMB4FV
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
PRIMARY
DAILYMED
V0N2VMB4FV
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
PRIMARY
CAS
18719-76-1
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
PRIMARY
DRUG CENTRAL
3975
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID00927864
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
PRIMARY
CHEBI
28064
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
PRIMARY
PUBCHEM
29231
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
PRIMARY
EVMPD
SUB08364MIG
Created by admin on Sat Dec 16 17:02:36 GMT 2023 , Edited by admin on Sat Dec 16 17:02:36 GMT 2023
PRIMARY
Related Record Type Details
ASPARAGUS
PARENT -> CONSTITUENT ALWAYS PRESENT
Oxygen radical absorbance capacity (ORAC) assays proved high antioxidant activity.
Related Record Type Details
Structure of KERACYANIN CATION
ACTIVE MOIETY
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
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