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
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
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 |
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/10383482Curator's Comment:: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/3896964
Sources: http://www.ncbi.nlm.nih.gov/pubmed/10383482
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
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL230 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11858749 |
93.3 µM [IC50] | ||
Target ID: CHEMBL221 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11858749 |
36.7 µM [IC50] | ||
Target ID: GO:0042554 Sources: http://www.ncbi.nlm.nih.gov/pubmed/10425115 |
13.1 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Cianidanol Approved UseCianidanol was introduced in 1976 as an adjunct in the treatment of liver disorders Launch Date1.89215998E11 |
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Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Biological evaluation of proanthocyanidin dimers and related polyphenols. | 1999 Jul |
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Suppression by flavonoids of cyclooxygenase-2 promoter-dependent transcriptional activity in colon cancer cells: structure-activity relationship. | 2000 Jul |
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Inhibitory activity of flavonoids and tannins against HIV-1 protease. | 2000 Sep |
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Estimation of procyanidin chain length. | 2001 |
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Biological actions of oligomeric procyanidins: proliferation of epithelial cells and hair follicle growth. | 2001 |
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Inhibition of in vitro low-density lipoprotein oxidation by oligomeric procyanidins present in chocolate and cocoas. | 2001 |
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Characterization of antioxidant effect of procyanidins. | 2001 |
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Mechanism of antioxidant effect of catechins. | 2001 |
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Catechins in tea: chemistry and analysis. | 2001 |
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Specific antioxidant activity of caffeoyl derivatives and other natural phenolic compounds: LDL protection against oxidation and decrease in the proinflammatory lysophosphatidylcholine production. | 2001 Apr |
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Separation of apple procyanidins into different degrees of polymerization by high-speed counter-current chromatography. | 2001 Apr 27 |
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Effects of de-alcoholated red wine and its phenolic fractions on platelet aggregation. | 2001 Feb |
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Nutrient distribution and phenolic antioxidants in air-classified fractions of beach pea (Lathyrus maritimus L.). | 2001 Feb |
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Tea catechins inhibit cholesterol oxidation accompanying oxidation of low density lipoprotein in vitro. | 2001 Feb |
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Green tea polyphenol (-)-epigallocatechin-3-gallate treatment of human skin inhibits ultraviolet radiation-induced oxidative stress. | 2001 Feb |
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Detrimental effect of cancer preventive phytochemicals silymarin, genistein and epigallocatechin 3-gallate on epigenetic events in human prostate carcinoma DU145 cells. | 2001 Feb 1 |
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Studies in polyphenol chemistry and bioactivity. 3.(1,2) stereocontrolled synthesis of epicatechin-4alpha,8-epicatechin, an unnatural isomer of the B-type procyanidins. | 2001 Feb 23 |
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Pharmacokinetics and system linearity of tea catechins in rat. | 2001 Jan |
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Antioxidant benzoylated flavan-3-ol glycoside from Celastrus orbiculatus. | 2001 Jan |
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Degradation of green tea catechins in tea drinks. | 2001 Jan |
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Quantitative analysis of polymeric procyanidins (Tannins) from grape (Vitis vinifera) seeds by reverse phase high-performance liquid chromatography. | 2001 Jan |
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Influence of metal ions on flavonoid protection against asbestos-induced cell injury. | 2001 Jan 1 |
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Comparative efficacy as antioxidants between ascorbic acid and epigallocatechin gallate on cells of two human lymphoblastoid lines. | 2001 Jan 15 |
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Is the cancer protective effect correlated with growth inhibitions by green tea (-)-epigallocatechin gallate mediated through an antioxidant mechanism? | 2001 Jan 26 |
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Protective effects of (-)-epigallocatechin-3-gallate on UVA- and UVB-induced skin damage. | 2001 Jan-Feb |
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Green tea catechins enhance tumor development in the colon without effects in the lung or thyroid after pretreatment with 1,2-Dimethylhydrazine or 2,2'-dihydroxy-di-n-propylnitrosamine in male F344 rats. | 2001 Jul 10 |
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Black tea extract, thearubigin fraction, counteracts the effect of tetanus toxin in mice. | 2001 Jun |
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Atmospheric carbon dioxide, irrigation, and fertilization effects on phenolic and nitrogen concentrations in loblolly pine (Pinus taeda) needles. | 2001 Jun |
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Formation and identification of 4'-O-methyl-(-)-epigallocatechin in humans. | 2001 Jun |
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The role of inducible-nitric oxide in cocaine-induced kindling. | 2001 Mar |
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Antioxidant effects of water extracts from barley (Hordeum vulgare L.) prepared under different roasting temperatures. | 2001 Mar |
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Polyphenols from Eucalyptus ovata. | 2001 Mar |
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Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. | 2001 Mar |
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The effects of phenolic components of tea on the production of pro- and anti-inflammatory cytokines by human leukocytes in vitro. | 2001 Mar 7 |
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Enantioselective synthesis of epigallocatechin-3-gallate (EGCG), the active polyphenol component from green tea. | 2001 Mar 8 |
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Combination effect of lignin F and natural products. | 2001 Mar-Apr |
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Furanocoumarins from the aerial parts of Dorstenia contrajerva. | 2001 May |
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Fast determination of procyanidins and other phenolic compounds in food samples by micellar electrokinetic chromatography using acidic buffers. | 2001 May |
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[Polyphenol constituents from Salacia species: quantitative analysis of mangiferin with alpha-glucosidase and aldose reductase inhibitory activities]. | 2001 May |
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The in vitro inhibitory effect of tannin derivatives on 3-hydroxy-3-methylglutaryl-coenzyme a reductase on vero cells. | 2001 May |
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Green tea polyphenol (-)-epigallocatechin-3-gallate treatment to mouse skin prevents UVB-induced infiltration of leukocytes, depletion of antigen-presenting cells, and oxidative stress. | 2001 May |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/otc/110166/label.jpg
Take 1~3 packet daily
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/3596873
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
Edited
Sat Jun 26 05:57:50 UTC 2021
by
admin
on
Sat Jun 26 05:57:50 UTC 2021
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Record UNII |
8R1V1STN48
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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LIVERTOX |
414
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DSLD |
119 (Number of products:75)
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Code System | Code | Type | Description | ||
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154-23-4
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PRIMARY | |||
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CATECHIN
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C63654
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1096790
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1367177
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8R1V1STN48
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CHEMBL311498
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SUB06226MIG
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D002392
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154-23-4
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9064
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205-825-1
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DB14086
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4804
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629
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M3172
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
The compound was screened for it's antioxidant capacity in the DPPH assay, and displayed a high antioxidant activity, with an IC50 value of 49.0 uM.
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TARGET -> INHIBITOR | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Secondary metabolite detected in developing cacao seeds.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT |
IN-VITRO
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METABOLITE -> PARENT |
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ACTIVE MOIETY |