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Chebulinic acid structure, CAS 18942-26-2

Chebulinic acid

CAS Number18942-26-2

SynonymsEutannin

Molecular FormulaC41H32O27

Molecular Weight956.677

Purity

Density2.0±0.1 g/cm3

Boiling Point1460.0±65.0 °C at 760 mmHg

Melting Point

Flash Point

Appearance

EINECS

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Cat. No.: 2A-0202584 Purity:
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Quality Control of [ 18942-26-2 ] SDS Specification MoL

COA NMR CNMR HPLC LC-MS
Chemical & Physical Properties
CAS Number18942-26-2
Catalog No.2A-0202584
Chinese Name诃子林鞣酸
SynonymsEutannin
Molecular FormulaC41H32O27
Molecular Weight956.677
Density2.0±0.1 g/cm3
Boiling Point1460.0±65.0 °C at 760 mmHg
Storage Condition2-8℃
ApplicationChebulinic acid is a natural M. tuberculosis DNA gyrase inhibitor and can also inhibit SMAD-3 phosphorylation and H+ K+-ATPase activity.
SMILESO=C(O)CC1C(=O)OC2C(COC(=O)c3cc(O)c(O)c(O)c3)OC(OC(=O)c3cc(O)c(O)c(O)c3)C(OC(=O)c3cc(O)c(O)c4c3C1C(O)C(=O)O4)C2OC(=O)c1cc(O)c(O)c(O)c1
InChIInChI=1S/C41H32O27/c42-15-1-10(2-16(43)26(15)51)35(56)62-9-22-31-33(66-36(57)11-3-17(44)27(52)18(45)4-11)34(41(63-22)68-37(58)12-5-19(46)28(53)20(47)6-12)67-38(59)13-7-21(48)29(54)32-25(13)24(30(55)40(61)65-32)14(8-23(49)50)39(60)64-31/h1-7,14,22,24,30-31,33-34,41-48,51-55H,8-9H2,(H,49,50)/t14-,22+,24-,30-,31+,33-,34+,41-/m0/s1
InChI KeyYGVHOSGNOYKRIH-REKMSKHASA-N
Hazard Symbolstransportation
MSDSmsds/203383_2_18942_26_2.pdf
BioactivityChebulinic acid is a potent natural inhibitor of M. tuberculosis DNA gyrase, also can inhibit SMAD-3 phosphorylation, inhibit H+ K+-ATPase activity. Related Catalog Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis Signaling Pathways >> Membrane Transporter/Ion Channel >> Proton Pump Signaling Pathways >> Stem Cell/Wnt >> TGF-beta/Smad Signaling Pathways >> TGF-beta/Smad >> TGF-beta/Smad Research Areas >> Infection Natural Products >> Phenols 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. Chemical & Physical Properties 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 InChIKey YGVHOSGNOYKRIH-REKMSKHASA-N SMILES O=C(O)CC1C(=O)OC2C(COC(=O)c3cc(O)c(O)c(O)c3)OC(OC(=O)c3cc(O)c(O)c(O)c3)C(OC(=O)c3cc(O)c(O)c4c3C1C(O)C(=O)O4)C2OC(=O)c1cc(O)c(O)c(O)c1 Storage condition 2-8℃
Use ofChebulinic acid is a potent natural inhibitor of M. tuberculosis DNA gyrase, also can inhibit SMAD-3 phosphorylation, inhibit H+ K+-ATPase activity. Properties Articles17 Name chebulinic acid Synonym More Synonyms Chebulinic acid Biological Activity 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 Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis Signaling Pathways >> Membrane Transporter/Ion Channel >> Proton Pump Signaling Pathways >> Stem Cell/Wnt >> TGF-beta/Smad Signaling Pathways >> TGF-beta/Smad >> TGF-beta/Smad Research Areas >> Infection Natural Products >> Phenols target: M. tuberculosis DNA gyrase[1], SMAD-3 phosphorylation[2], H+ K+-ATPase activity.[3]IC50: 65.01 μg/ml ( H+ K+-ATPase ) [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. Chemical & Physical Properties Molecular Formula C41H32O27 Exact Mass 956.113098 PSA 447.09000 Index of Refraction 1.837 InChIKey YGVHOSGNOYKRIH-REKMSKHASA-N Storage condition 2-8℃
Transport InfoShipping Name: UN
MSDS Transport InfoModule 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available
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