Carboxyatractyloside potassium
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MedKoo CAT#: 558144

CAS#: 33286-30-5 (potassium)

Description: Carboxyatractyloside is a highly selective inhibitor of cytosolic side-specific mitochondrial ADP/ATP carrier; i.e. adenine nucleotide translocase (ANT).


Chemical Structure

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Carboxyatractyloside potassium
CAS# 33286-30-5 (potassium)

Theoretical Analysis

MedKoo Cat#: 558144
Name: Carboxyatractyloside potassium
CAS#: 33286-30-5 (potassium)
Chemical Formula: C31H44K2O18S2
Exact Mass:
Molecular Weight: 846.1243
Elemental Analysis: C, 43.96; H, 5.24; K, 9.23; O, 34.00; S, 7.57

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Related CAS #: 33286-30-5 (potassium)   35988-42-2 (free acid)    

Synonym: Gummiferin; Carboxyatractyloside potassium

IUPAC/Chemical Name: potassium (2S,4aS,6aR,7S,9R,11aS,11bS)-7-hydroxy-2-(((2R,3R,4R,5R,6R)-6-(hydroxymethyl)-3-((3-methylbutanoyl)oxy)-4,5-bis(sulfooxy)tetrahydro-2H-pyran-2-yl)oxy)-11b-methyl-8-methylenedodecahydro-6a,9-methanocyclohepta[a]naphthalene-4,4(1H)-dicarboxylate

InChi Key: FPJGZZYAZUKPAD-WWJHHVHBSA-L

InChi Code: InChI=1S/C31H46O18S2.2K/c1-14(2)9-21(33)47-24-23(49-51(42,43)44)22(48-50(39,40)41)18(13-32)46-26(24)45-17-11-29(4)19-6-5-16-10-30(19,25(34)15(16)3)8-7-20(29)31(12-17,27(35)36)28(37)38;;/h14,16-20,22-26,32,34H,3,5-13H2,1-2,4H3,(H,35,36)(H,37,38)(H,39,40,41)(H,42,43,44);;/q;2*+1/p-2/t16-,17+,18-,19+,20+,22-,23+,24-,25+,26-,29+,30-;;/m1../s1

SMILES Code: CC(CC(O[C@H]1[C@@H](O[C@@H]([C@H]([C@@H]1OS(=O)(O)=O)OS(=O)(O)=O)CO)O[C@H]2C[C@]3([C@@H]4CC[C@@H]5C[C@]4([C@H](C5=C)O)CC[C@@H]3C(C([O-])=O)(C([O-])=O)C2)C)=O)C.[K+].[K+](O)=O)OC(CC(C)C)=O)C[C@@]4(C)[C@@]31[H]

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

Preparing Stock Solutions

The following data is based on the product molecular weight 846.1243 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.

Recalculate based on batch purity %
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

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1: Nikles S, Heuberger H, Hilsdorf E, Schmücker R, Seidenberger R, Bauer R. Influence of Processing on the Content of Toxic Carboxyatractyloside and Atractyloside and the Microbiological Status of Xanthium sibiricum Fruits (Cang'erzi). Planta Med. 2015 Aug;81(12-13):1213-20. doi: 10.1055/s-0035-1546207. Epub 2015 Aug 19. PubMed PMID: 26287695.

2: Duo R, Chen Y, Liu Y, Huang Z, Liu Y, Yi J. [Determination of carboxyatractyloside and atractyloside in Xanthii Fructus by HPLC]. Zhongguo Zhong Yao Za Zhi. 2012 Aug;37(15):2313-6. Chinese. PubMed PMID: 23189741.

3: Pebay-Peyroula E, Dahout-Gonzalez C, Kahn R, Trézéguet V, Lauquin GJ, Brandolin G. Structure of mitochondrial ADP/ATP carrier in complex with carboxyatractyloside. Nature. 2003 Nov 6;426(6962):39-44. PubMed PMID: 14603310.

4: Carlier J, Romeuf L, Guitton J, Priez-Barallon C, Bévalot F, Fanton L, Gaillard Y. A validated method for quantifying atractyloside and carboxyatractyloside in blood by HPLC-HRMS/MS, a non-fatal case of intoxication with Atractylis gummifera L. J Anal Toxicol. 2014 Nov-Dec;38(9):619-27. doi: 10.1093/jat/bku078. Epub 2014 Jul 2. PubMed PMID: 24990875.

5: Sanchez JF, Kauffmann B, Grélard A, Sanchez C, Trézéguet V, Huc I, Lauquin GJ. Unambiguous structure of atractyloside and carboxyatractyloside. Bioorg Med Chem

Lett. 2012 Apr 15;22(8):2973-5. doi: 10.1016/j.bmcl.2012.02.040. Epub 2012 Feb 22. PubMed PMID: 22425567.

6: Hernández-Esquivel L, Natalia-Pavón, Zazueta C, García N, Correa F, Chávez E.

Protective action of tamoxifen on carboxyatractyloside-induced mitochondrial permeability transition. Life Sci. 2011 Apr 11;88(15-16):681-7. doi: 10.1016/j.lfs.2011.02.006. Epub 2011 Feb 12. PubMed PMID: 21324322.

7: Turgut M, Alhan CC, Gürgöze M, Kurt A, Doğan Y, Tekatli M, Akpolat N, Aygün AD. Carboxyatractyloside poisoning in humans. Ann Trop Paediatr. 2005 Jun;25(2):125-34. PubMed PMID: 15949201.

8: Vignais PV, Douce R, Lauquin GJ, Vignais PM. Binding of radioactively labeled
carboxyatractyloside, atractyloside and bongkrekic acid to the ADP translocator of potato mitochondria. Biochim Biophys Acta. 1976 Sep 13;440(3):688-96. PubMed PMID: 963047.

9: García N, Pavón N, Chávez E. The effect of N-ethylmaleimide on permeability transition as induced by carboxyatractyloside, agaric acid, and oleate. Cell Biochem Biophys. 2008;51(2-3):81-7. doi: 10.1007/s12013-008-9016-5. Epub 2008 Jul 23. PubMed PMID: 18649145.

10: Chávez E, Zazueta C, García N. Carboxyatractyloside increases the effect of oleate on mitochondrial permeability transition. FEBS Lett. 1999 Feb 19;445(1):189-91. PubMed PMID: 10069398.

11: García N, Zazueta C, Martínez-Abundis E, Pavón N, Chávez E. Cyclosporin A is

unable to inhibit carboxyatractyloside-induced permeability transition in aged mitochondria. Comp Biochem Physiol C Toxicol Pharmacol. 2009 Apr;149(3):374-81. doi: 10.1016/j.cbpc.2008.09.006. Epub 2008 Sep 18. PubMed PMID: 18835371.

12: Chávez E, Moreno-Sánchez R, Zazueta C, Reyes-Vivas H, Arteaga D. Intramitochondrial K+ as activator of carboxyatractyloside-induced Ca2+ release.

Biochim Biophys Acta. 1991 Dec 9;1070(2):461-6. PubMed PMID: 1764458.

13: Ishiyama S, Hiraga K, Tuboi S. An improved method for labeling carboxyatractyloside by [3H]KBH4. Biochem Int. 1984 Feb;8(2):305-11. PubMed PMID: 6477602.

14: Krejci ME, Koechel DA. Acute effects of carboxyatractyloside and stevioside,

inhibitors of mitochondrial ADP/ATP translocation, on renal function and ultrastructure in pentobarbital-anesthetized dogs. Toxicology. 1992;72(3):299-313. PubMed PMID: 1585384.

15: García N, Zazueta C, El-Hafidi M, Pavón N, Martínez-Abundis E, Hernández-Esquivel L, Chávez E. Cyclosporin A inhibits UV-radiation-induced membrane damage but is unable to inhibit carboxyatractyloside-induced permeability transition. Radiat Res. 2009 Nov;172(5):575-83. doi: 10.1667/RR1799.1. PubMed PMID: 19883225.

16: Block MR, Pougeois R, Vignais PV. Chemical radiolabeling of carboxyatractyloside by [14C]acetic anhydride: binding properties of [14C]acetylcarboxyatractyloside to the mitochondrial ADP/ATP carrier. FEBS Lett.

1980 Aug 11;117(1):335-40. PubMed PMID: 6250898.

17: Novgorodov SA, Gudz TI, Jung DW, Brierley GP. The nonspecific inner membrane

pore of liver mitochondria: modulation of cyclosporin sensitivity by ADP at carboxyatractyloside-sensitive and insensitive sites. Biochem Biophys Res Commun. 1991 Oct 15;180(1):33-8. PubMed PMID: 1930231.

18: Shabalina IG, Kramarova TV, Nedergaard J, Cannon B. Carboxyatractyloside effects on brown-fat mitochondria imply that the adenine nucleotide translocator

isoforms ANT1 and ANT2 may be responsible for basal and fatty-acid-induced uncoupling respectively. Biochem J. 2006 Nov 1;399(3):405-14. PubMed PMID: 16831128; PubMed Central PMCID: PMC1615905.

19: Hatch RC, Jain AV, Weiss R, Clark JD. Toxicologic study of carboxyatractyloside (active principle in cocklebur--Xanthium strumarium) in rats treated with enzyme inducers and inhibitors and glutathione precursor and depletor. Am J Vet Res. 1982 Jan;43(1):111-6. PubMed PMID: 7091806.

20: Austin J, Aprille JR. Carboxyatractyloside-insensitive influx and efflux of adenine nucleotides in rat liver mitochondria. J Biol Chem. 1984 Jan 10;259(1):154-60. PubMed PMID: 6706925.