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18942-26-2

18942-26-2 structure
18942-26-2 structure

Name chebulinic acid
Synonyms 7,11-Methanopyrano[4,3,2-kl][2,5,8]benzotrioxacyclotridecin-4-acetic acid, 2,3,3a,4,5,7,8,10,11,13-decahydro-3,15,16-trihydroxy-2,5,13-trioxo-10,17-bis[(3,4,5-trihydroxybenzoyl)oxy]-8-[[(3,4,5-trihydroxybenzoyl)oxy]methyl]-, (3S,3aS,4S,7R,8R,10S,11R,17S)-
Eutannin
[(4R,5S,7R,8R,11S,12S,13S,21S)-13,17,18-Trihydroxy-2,10,14-trioxo-5,21-bis[(3,4,5-trihydroxybenzoyl)oxy]-7-{[(3,4,5-trihydroxybenzoyl)oxy]methyl}-3,6,9,15-tetraoxatetracyclo[10.7.1.1.0]hen icosa-1(20),16,18-trien-11-yl]acetic acid
Description Chebulinic acid is a potent natural inhibitor of M. tuberculosis DNA gyrase, also can inhibit SMAD-3 phosphorylation, inhibit H+ K+-ATPase activity.
Related Catalog
Target

target: M. tuberculosis DNA gyrase[1], SMAD-3 phosphorylation[2], H+ K+-ATPase activity.[3]IC50: 65.01 μg/ml ( H+ K+-ATPase ) [3]

In Vitro In vitro: binding of Chebulinic acid causes displacement of catalytic Tyr129 away from its target DNA-phosphate molecule. [1] Chebulinic acid reduce the expression and activity of MMP-2 at an ED50 value of 100 μM. EMT (Epithelial to Mesenchymal Transition) is found to be induced in ARPE-19 cells, through SMAD-3 phosphorylation and it is inhibited by CA. [2] chebulinic acid significantly inhibited H+ K+-ATPase activity in vitrowith IC50 of 65.01 μg/ml. [3]
References

[1]. Patel K et al. Identification of chebulinic acid as potent natural inhibitor of M. tuberculosis DNA gyrase and molecular insights into its binding mode of action. Comput Biol Chem. 2015 Dec;59 Pt A:37-47.

[2]. Sivasankar S et al. Aqueous and alcoholic extracts of Triphala and their active compounds chebulagic acid and chebulinic acidprevented epithelial to mesenchymal transition in retinal pigment epithelial cells, by inhibiting SMAD-3 phosphorylation. PLoS One. 2015 Mar 20

[3]. Mishra V et al. Anti-secretory and cyto-protective effects of chebulinic acid isolated from the fruits of Terminalia chebula on gastric ulcers. Phytomedicine. 2013 Apr 15;20(6):506-11.

Density 2.0±0.1 g/cm3
Boiling Point 1460.0±65.0 °C at 760 mmHg
Molecular Formula C41H32O27
Molecular Weight 956.677
Flash Point 437.2±27.8 °C
Exact Mass 956.113098
PSA 447.09000
LogP 4.14
Vapour Pressure 0.0±0.3 mmHg at 25°C
Index of Refraction 1.837
Storage condition 2-8℃
RIDADR NONH for all modes of transport
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