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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H14O6
Molecular Weight 290.2686
Optical Activity ( + )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIANIDANOL

SMILES

c1cc(c(cc1[C@]2([H])[C@]([H])(Cc3c(cc(cc3O2)O)O)O)O)O

InChI

InChIKey=PFTAWBLQPZVEMU-DZGCQCFKSA-N
InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1

HIDE SMILES / InChI

Molecular Formula C15H14O6
Molecular Weight 290.2686
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/3896964

Cianidanol is an antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. One of the polyphenols present in green tea, (+)-catechin (Cianidanol), has been studied for its effects on animal models of hepatitis, as well as in human clinical studies. Pure (+)-catechin (also known as (+)- cyanidanol-3 – trade name Catergen) has been used to treat hepatitis since 1976. This compound has been shown to be an efficient immune stimulator, promoting activation of macrophages, cytotoxic-T-lymphocytes, and natural killer cells in mice. Several clinical studies demonstrate the effectiveness of (+)-catechin in the treatment of viral hepatitis. Pure (+)-catechin has been found to cause hemolysis in some patients, possibly by the promotion of antibody formation against (+)-catechin, which might cross-react with red blood cells. However, there are no reports in the literature of green tea, green tea extracts, or green tea polyphenols causing this side-effect.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
93.2999999999999972 µM [IC50]
36.7000000000000028 µM [IC50]
13.0999999999999996 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Cianidanol

Approved Use

Cianidanol was introduced in 1976 as an adjunct in the treatment of liver disorders

Launch Date

189216000000
Preventing
Primary
Preventing
PubMed

PubMed

TitleDatePubMed
Biological evaluation of proanthocyanidin dimers and related polyphenols.
1999 Jul
Suppression by flavonoids of cyclooxygenase-2 promoter-dependent transcriptional activity in colon cancer cells: structure-activity relationship.
2000 Jul
Inhibitory activity of flavonoids and tannins against HIV-1 protease.
2000 Sep
Estimation of procyanidin chain length.
2001
Characterization of antioxidant effect of procyanidins.
2001
Green tea: biochemical and biological basis for health benefits.
2001
Protective effect of phenolic compounds isolated from the hooks and stems of Uncaria sinensis on glutamate-induced neuronal death.
2001
Phenolics and physico-chemical characteristics of persimmon during post-harvest storage.
2001 Apr
Hydroxylations and methylations of quercetin, fisetin, and catechin by Streptomyces griseus.
2001 Apr
Ester bond-containing tea polyphenols potently inhibit proteasome activity in vitro and in vivo.
2001 Apr 20
Separation of apple procyanidins into different degrees of polymerization by high-speed counter-current chromatography.
2001 Apr 27
Structural features of procyanidin interactions with salivary proteins.
2001 Feb
Nutrient distribution and phenolic antioxidants in air-classified fractions of beach pea (Lathyrus maritimus L.).
2001 Feb
Polyphyenolics increase t-PA and u-PA gene transcription in cultured human endothelial cells.
2001 Feb
Green tea polyphenol (-)-epigallocatechin-3-gallate treatment of human skin inhibits ultraviolet radiation-induced oxidative stress.
2001 Feb
Modulation of the biosynthesis of some phenolic compounds in Olea europaea L. fruits: their influence on olive oil quality.
2001 Jan
Thiolysis-HPLC characterization of apple procyanidins covering a large range of polymerization states.
2001 Jan
Influence of metal ions on flavonoid protection against asbestos-induced cell injury.
2001 Jan 1
Protective effects of (-)-epigallocatechin-3-gallate on UVA- and UVB-induced skin damage.
2001 Jan-Feb
Atmospheric carbon dioxide, irrigation, and fertilization effects on phenolic and nitrogen concentrations in loblolly pine (Pinus taeda) needles.
2001 Jun
The role of inducible-nitric oxide in cocaine-induced kindling.
2001 Mar
Color and stability of pigments derived from the acetaldehyde-mediated condensation between malvidin 3-O-glucoside and (+)-catechin.
2001 Mar
Flavonoids and phenylpropanoid derivatives from Campanula barbata.
2001 Mar
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.
2001 Mar
Antimutagenic activity of green tea and black tea extracts studied in a dynamic in vitro gastrointestinal model.
2001 Mar 1
Synthesis of a 3,4,5-trimethoxybenzoyl ester analogue of epigallocatechin-3-gallate (EGCG): a potential route to the natural product green tea catechin, EGCG.
2001 Mar 22
Enantioselective synthesis of epigallocatechin-3-gallate (EGCG), the active polyphenol component from green tea.
2001 Mar 8
Water-soluble antioxidants inhibit macrophage recognition of oxidized erythrocytes.
2001 May
Anti-interferon gamma action of epigallocatechin-3-gallate mediated by specific inhibition of STAT1 activation.
2001 May
Patents

Sample Use Guides

In Vivo Use Guide
Take 1~3 packet daily
Route of Administration: Oral
In Vitro Use Guide
The in vitro effect of the drug was assessed using cianidanol at 10(-6), 10(-5) and 10(-4) M concentrations.
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:57:50 UTC 2021
Edited
by admin
on Sat Jun 26 05:57:50 UTC 2021
Record UNII
8R1V1STN48
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIANIDANOL
INN   JAN   MART.   WHO-DD  
INN  
Official Name English
(+)-CATECHIN [USP-RS]
Common Name English
CATECHIN
MI   VANDF  
Common Name English
D-CATECHOL
Common Name English
(+)-CATECHOL
Systematic Name English
(+)-CATECHIN (CONSTITUENT OF MARITIME PINE) [DSC]
Common Name English
CIANIDANOL [INN]
Common Name English
2H-1-BENZOPYRAN-3,5,7-TRIOL, 2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-, (2R,3S)-
Systematic Name English
(+)-CATECHIN
Common Name English
CATECHIN, D-
Common Name English
(+)-CATECHIN (CONSTITUENT OF GRAPE SEEDS OLIGOMERIC PROANTHOCYANIDINS) [DSC]
Common Name English
CIANIDANOL [WHO-DD]
Common Name English
CIANIDANOL [MART.]
Common Name English
CIANIDOL
Common Name English
CATECHIN [VANDF]
Common Name English
(+)-CATECHIN (CONSTITUENT OF POWDERED DECAFFEINATED GREEN TEA EXTRACT) [DSC]
Common Name English
CATECHIN [MI]
Common Name English
NSC-2819
Code English
CATECHUIC ACID
Common Name English
CIANIDANOL [JAN]
Common Name English
CATERGEN
Common Name English
CATECHINIC ACID
Common Name English
Classification Tree Code System Code
LIVERTOX 414
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
DSLD 119 (Number of products:75)
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
Code System Code Type Description
CAS
154-23-4
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
WIKIPEDIA
CATECHIN
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
NCI_THESAURUS
C63654
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
USP_CATALOG
1096790
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY USP-RS
RXCUI
1367177
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY RxNorm
FDA UNII
8R1V1STN48
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
ChEMBL
CHEMBL311498
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
EVMPD
SUB06226MIG
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
MESH
D002392
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
EPA CompTox
154-23-4
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
PUBCHEM
9064
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-825-1
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
DRUG BANK
DB14086
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
INN
4804
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
DRUG CENTRAL
629
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
MERCK INDEX
M3172
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY Merck Index
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