Chebulagic acid | CAS# 23094-71-5 | inhibits COX-2

MedKoo Cat#: 412803 | Name: Chebulagic acid

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Chebulagic acid also inhibits COX-2.

Chemical Structure

Chebulagic acid

CAS#23094-71-5

Theoretical Analysis

MedKoo Cat#: 412803

Name: Chebulagic acid

CAS#: 23094-71-5

Chemical Formula: C41H30O27

Exact Mass: 954.0974

Molecular Weight: 954.66

Elemental Analysis: C, 51.58; H, 3.17; O, 45.25

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 550.00	2 Weeks
10mg	USD 950.00	2 Weeks

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Related CAS #

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Synonym

Chebulagic acid; NSC 342674; NSC 342674; NSC 342674

IUPAC/Chemical Name

2-((53S,53aS,54S,57R,58R,510S,511R,517S)-14,15,16,24,25,26,53,515,516-nonahydroxy-52,55,513,3,8-pentaoxo-510-((3,4,5-trihydroxybenzoyl)oxy)-52,53,53a,54,55,57,58,510,511,513-decahydro-4,7-dioxa-5(17,8)-7,11-methano[1,4,7]trioxacyclotridecino[11,10,9-de]chromena-1,2(1,2)-dibenzenacyclooctaphane-54-yl)acetic acid

InChi Key

HGJXAVROWQLCTP-YABCKIEDSA-N

InChi Code

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

SMILES Code

O=C(C1=CC(O)=C(O)C(O)=C1)O[C@H]2[C@H](OC(C3=C([C@@]([C@@H]4CC(O)=O)([H])[C@H](O)C5=O)C(O5)=C(O)C(O)=C3)=O)[C@@H](OC(C6=CC(O)=C(O)C(O)=C67)=O)[C@H](OC4=O)[C@@H](COC(C8=C7C(O)=C(O)C(O)=C8)=O)O2

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 954.66 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Yang L, Liu Y, Zhang W, Hua Y, Chen B, Wu Q, Chen D, Liu S, Li X. Ferroptosis-Inhibitory Difference between Chebulagic Acid and Chebulinic Acid Indicates Beneficial Role of HHDP. Molecules. 2021 Jul 15;26(14):4300. doi: 10.3390/molecules26144300. PMID: 34299576; PMCID: PMC8303713. 2: Vasu G, Sundaram R, Muthu K. Chebulagic acid attenuates HFD/streptozotocin induced impaired glucose metabolism and insulin resistance via up regulations of PPAR γ and GLUT 4 in type 2 diabetic rats. Toxicol Mech Methods. 2022 Mar;32(3):159-170. doi: 10.1080/15376516.2021.1976333. Epub 2021 Sep 22. PMID: 34470562. 3: Zhao J, Shi Y, Ma Y, Pan L, Wang Y, Yuan L, Dong J, Ying J. Chebulagic acid suppresses gastric cancer by inhibiting the AURKA/β-catenin/Wnt pathway. Front Pharmacol. 2023 Mar 1;14:1143427. doi: 10.3389/fphar.2023.1143427. PMID: 36937887; PMCID: PMC10014572. 4: Duncan MC, Onguéné PA, Kihara I, Nebangwa DN, Naidu ME, Williams DE, Balgi AD, Andrae-Marobela K, Roberge M, Andersen RJ, Niikura M, Ntie-Kang F, Tietjen I. Virtual Screening Identifies Chebulagic Acid as an Inhibitor of the M2(S31N) Viral Ion Channel and Influenza A Virus. Molecules. 2020 Jun 24;25(12):2903. doi: 10.3390/molecules25122903. PMID: 32599753; PMCID: PMC7356874. 5: Gao H, Huang YN, Gao B, Kawabata J. Chebulagic acid is a potent alpha- glucosidase inhibitor. Biosci Biotechnol Biochem. 2008 Feb;72(2):601-3. doi: 10.1271/bbb.70591. Epub 2008 Feb 7. PMID: 18256469. 6: Li P, Du R, Wang Y, Hou X, Wang L, Zhao X, Zhan P, Liu X, Rong L, Cui Q. Identification of Chebulinic Acid and Chebulagic Acid as Novel Influenza Viral Neuraminidase Inhibitors. Front Microbiol. 2020 Feb 28;11:182. doi: 10.3389/fmicb.2020.00182. PMID: 32256457; PMCID: PMC7093024. 7: Huang YN, Zhao DD, Gao B, Zhong K, Zhu RX, Zhang Y, Xie WJ, Jia LR, Gao H. Anti-hyperglycemic effect of chebulagic acid from the fruits of Terminalia chebula Retz. Int J Mol Sci. 2012;13(5):6320-6333. doi: 10.3390/ijms13056320. Epub 2012 May 22. PMID: 22754367; PMCID: PMC3382786. 8: Kim HJ, Kim J, Kang KS, Lee KT, Yang HO. Neuroprotective Effect of Chebulagic Acid via Autophagy Induction in SH-SY5Y Cells. Biomol Ther (Seoul). 2014 Jul;22(4):275-81. doi: 10.4062/biomolther.2014.068. PMID: 25143804; PMCID: PMC4131520. 9: Shanmuganathan S, Angayarkanni N. Chebulagic acid and Chebulinic acid inhibit TGF-β1 induced fibrotic changes in the chorio-retinal endothelial cells by inhibiting ERK phosphorylation. Microvasc Res. 2019 Jan;121:14-23. doi: 10.1016/j.mvr.2018.09.001. Epub 2018 Sep 4. PMID: 30189210. 10: Bopardikar M, Koti Ainavarapu SR, Hosur RV. Pyrogallol, Corilagin and Chebulagic acid target the "fuzzy coat" of alpha-synuclein to inhibit the fibrillization of the protein. RSC Adv. 2022 Dec 14;12(55):35770-35777. doi: 10.1039/d2ra04358k. PMID: 36545068; PMCID: PMC9749937. 11: Du R, Cooper L, Chen Z, Lee H, Rong L, Cui Q. Discovery of chebulagic acid and punicalagin as novel allosteric inhibitors of SARS-CoV-2 3CLpro. Antiviral Res. 2021 Jun;190:105075. doi: 10.1016/j.antiviral.2021.105075. Epub 2021 Apr 17. PMID: 33872675; PMCID: PMC8052511. 12: Shanmuganathan S, Angayarkanni N. Chebulagic acid Chebulinic acid and Gallic acid, the active principles of Triphala, inhibit TNFα induced pro-angiogenic and pro-inflammatory activities in retinal capillary endothelial cells by inhibiting p38, ERK and NFkB phosphorylation. Vascul Pharmacol. 2018 Sep;108:23-35. doi: 10.1016/j.vph.2018.04.005. Epub 2018 Apr 17. PMID: 29678603. 13: Reddy DB, Reddy TC, Jyotsna G, Sharan S, Priya N, Lakshmipathi V, Reddanna P. Chebulagic acid, a COX-LOX dual inhibitor isolated from the fruits of Terminalia chebula Retz., induces apoptosis in COLO-205 cell line. J Ethnopharmacol. 2009 Jul 30;124(3):506-12. doi: 10.1016/j.jep.2009.05.022. Epub 2009 May 28. PMID: 19481594. 14: Yang Y, Xiu J, Liu J, Zhang L, Li X, Xu Y, Qin C, Zhang L. Chebulagic acid, a hydrolyzable tannin, exhibited antiviral activity in vitro and in vivo against human enterovirus 71. Int J Mol Sci. 2013 May 3;14(5):9618-27. doi: 10.3390/ijms14059618. Erratum in: Int J Mol Sci. 2021 Aug 06;22(16): PMID: 23644889; PMCID: PMC3676802. 15: Yeggoni DP, Meti M, Subramanyam R. Chebulinic and chebulagic acid binding with serum proteins: biophysical and molecular docking approach. J Biomol Struct Dyn. 2023 Jun;41(9):4024-4039. doi: 10.1080/07391102.2022.2060862. Epub 2022 Apr 9. PMID: 35403561. 16: Athira AP, Abhinand CS, Saja K, Helen A, Reddanna P, Sudhakaran PR. Anti- angiogenic effect of chebulagic acid involves inhibition of the VEGFR2- and GSK-3β-dependent signaling pathways. Biochem Cell Biol. 2017 Oct;95(5):563-570. doi: 10.1139/bcb-2016-0132. Epub 2017 May 3. PMID: 28467858. 17: Lu Y, Yan H, Teng S, Yang X. A liquid chromatography-tandem mass spectrometry method for preclinical pharmacokinetics and tissue distribution of hydrolyzable tannins chebulinic acid and chebulagic acid in rats. Biomed Chromatogr. 2019 Mar;33(3):e4425. doi: 10.1002/bmc.4425. Epub 2018 Dec 12. PMID: 30397912. 18: Shyni GL, Kavitha S, Indu S, Arya AD, Anusree SS, Vineetha VP, Vandana S, Sundaresan A, Raghu KG. Chebulagic acid from Terminalia chebula enhances insulin mediated glucose uptake in 3T3-L1 adipocytes via PPARγ signaling pathway. Biofactors. 2014 Nov-Dec;40(6):646-57. doi: 10.1002/biof.1193. Epub 2014 Dec 20. PMID: 25529897. 19: Hassan Bulbul MR, Uddin Chowdhury MN, Naima TA, Sami SA, Imtiaj MS, Huda N, Uddin MG. A comprehensive review on the diverse pharmacological perspectives of Terminalia chebula Retz. Heliyon. 2022 Aug 14;8(8):e10220. doi: 10.1016/j.heliyon.2022.e10220. PMID: 36051270; PMCID: PMC9424961. 20: Athira AP, Helen A, Saja K, Reddanna P, Sudhakaran PR. Inhibition of Angiogenesis In Vitro by Chebulagic Acid: A COX-LOX Dual Inhibitor. Int J Vasc Med. 2013;2013:843897. doi: 10.1155/2013/843897. Epub 2013 Oct 31. PMID: 24288615; PMCID: PMC3833124.