Chebulagic acid

Name: Chebulagic acid
Brand: BOC Sciences
Rating: 5 (1 reviews)

Category	Influenza Virus
CAS	23094-71-5
Description	Chebulagic acid is a polyphenol and tannin that has been found in T. chebula and has diverse biological activities. It is an inhibitor of COX-1, COX-2, and 5-lipoxygenase (5-LO; IC50s = 15, 0.92, and 2.1 μM, respectively) as well as α-glucosidase and 15-LO (IC50s = 0.05 and 24.9 μM, respectively). Chebulagic acid inhibit the LPS-induced upregulation of TNF-α and IL-1β in a dose- and time-dependent manner. And it can also inhibit the production of NO, prostaglandin E2 (PGE2), and reactive oxygen species (ROS), and nuclear translocation of NF-κB in RAW 264.7 macrophages in a concentration-dependent manner. Chebulagic acid also show a protective effect against 1-methyl-4-phenylpyridinium (MPP+) - induce cytotoxicity which mimics the pathological symptom of Parkinson's disease.

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Product Information

Synonyms	β-D-glucopyranose; Cyclic 3,6-[(1R)-4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate] 1-(3,4,5-trihydroxybenzoate); Cyclic 2→2:4→1-ester with (2S)-2-[(3S,4S)-5-carboxy-3,4-dihydro-3,7,8-trihydroxy-2-oxo-2H-1-benzopyran-4-yl]butanedioic acid
IUPAC Name	2-[13,14,15,18,19,20,31,35,36-nonahydroxy-2,10,23,28,32-pentaoxo-5-(3,4,5-trihydroxybenzoyl)oxy-3,6,9,24,27,33-hexaoxaheptacyclo[28.7.1.04,25.07,26.011,16.017,22.034,38]octatriaconta-1(37),11,13,15,17,19,21,34(38),35-nonaen-29-yl]acetic acid
Molecular Weight	954.66
Molecular Formula	C41H30O27
Canonical SMILES	C1C2C3C(C(C(O2)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C6=C5C(C(C(=O)O3)CC(=O)O)C(C(=O)O6)O)O)O)OC(=O)C7=CC(=C(C(=C7C8=C(C(=C(C=C8C(=O)O1)O)O)O)O)O)O
InChI	InChI=1S/C41H30O27/c42-13-1-8(2-14(43)24(13)49)35(56)68-41-34-33-31(64-39(60)12(6-19(47)48)22-23-11(38(59)67-34)5-17(46)27(52)32(23)65-40(61)30(22)55)18(63-41)7-62-36(57)9-3-15(44)25(50)28(53)20(9)21-10(37(58)66-33)4-16(45)26(51)29(21)54/h1-5,12,18,22,30-31,33-34,41-46,49-55H,6-7H2,(H,47,48)/t12-,18+,22-,30-,31+,33-,34+,41-/m0/s1
InChIKey	HGJXAVROWQLCTP-YABCKIEDSA-N
Boiling Point	1610.6±65.0 °C at 760 mmHg
Melting Point	>300°C
Flash Point	480.0±27.8 °C
Purity	95%
Density	2.1±0.1 g/cm3
Solubility	~0.25 mg/ml in a 1:3 solution of DMSO:PBS (pH 7.2); ~5 ng/ml in EtOH; ~20 mg/ml in DMSO & DMF.
Appearance	White to Light Yellow Solid
Application	Topoisomerase I Inhibitors
Storage	Store at -20 °C
Complexity	1970
Exact Mass	954.09744568
Index Of Refraction	1.876
In Vitro	Chebulagic acid can enhance the Autophagy. Chebulagic acid exert anti-inflammatory and anti-infective effects. Chebulagic acid also shows a protective effect against 1-methyl-4-phenylpyridinium (MPP+)-induce cytotoxicity which mimics the pathological symptom of Parkinson's disease. Chebulagic acid inhibits the LPS-induced upregulation of TNF-α and IL-1β in a dose- and time-dependent manner. Furthermore, LPS-activated MAPK signaling is inhibited by Chebulagic acid treatment in the EA.hy926 cells.
PSA	447.09000
Target	COX; Lipoxygenase; SARS-CoV; Influenza Virus
Vapor Pressure	0.0±0.3 mmHg at 25°C
XLogP3-AA	0.4