Carboxyatractyloside | CAS# 35988-42-2 | inhibits the ADP/ATP translocase

MedKoo Cat#: 412322 | Name: Carboxyatractyloside

Description:

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

Carboxyatractyloside is a highly toxic diterpene glycoside that inhibits the ADP/ATP translocase. It's about 10 times more potent than atractyloside. While atractyloside is effective in the inhibition of oxidative phosphorylation, carboxyatractyloside is considered to be more effective.

Chemical Structure

Carboxyatractyloside

CAS#35988-42-2 (free acid)

Theoretical Analysis

MedKoo Cat#: 412322

Name: Carboxyatractyloside

CAS#: 35988-42-2 (free acid)

Chemical Formula: C31H46O18S2

Exact Mass: 770.2126

Molecular Weight: 770.81

Elemental Analysis: Chemical Formula: Exact Mass: Molecular Weight: Elemental Analysis: C, 48.31; H, 6.02; O, 37.36; S, 8.32

Price and Availability

Size	Price	Availability	Quantity

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

33286-30-5 (dipotassium) 35988-42-2 (free acid) 77228-71-8 (tripotassium)

Synonym

Carboxyatractyloside; Carboxyatractylate

IUPAC/Chemical Name

Kaur-16-ene-18,19-dioic acid, 15-hydroxy-2-((2-O-(3-methyl-1-oxobutyl)-3,4-di-O-sulfo-alpha-D-glucopyranosyl)oxy)-, (2beta,15alpha)-

InChi Key

AQFATIOBERWBDY-LIGJTEMZSA-N

InChi Code

InChI=1S/C31H46O18S2/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)/t16-,17+,18-,19+,20+,22-,23+,24-,25+,26+,29+,30-/m1/s1

SMILES Code

C=C([C@H](CC1)C2)[C@H](O)[C@@]32CC[C@]4([H])C(C(O)=O)(C(O)=O)C[C@@H](O[C@@H]5[C@@H]([C@H]([C@@H]([C@@H](CO)O5)OS(=O)(O)=O)OS(=O)(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

>3 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 770.81 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: Pan H, Yang F, Xiang D, Shi F. Simultaneous quantification of atractyloside and carboxyatractyloside in rat plasma by LC-MS/MS: Application to a pharmacokinetic study after oral administration of Xanthii Fructus extract. J Sep Sci. 2020 Feb;43(3):590-597. doi: 10.1002/jssc.201900888. Epub 2019 Dec 2. PMID: 31701660. 2: 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. doi: 10.1016/0005-2728(76)90051-7. PMID: 963047. 3: 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. doi: 10.1179/146532805X45728. PMID: 15949201. 4: 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. PMID: 26287695. 5: Luciani S, Varotto R. Difference between atractyloside and carboxyatractyloside on the binding to the mitochondrial membrane. FEBS Lett. 1975 Aug 15;56(2):194-7. doi: 10.1016/0014-5793(75)81089-1. PMID: 239866. 6: 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. PMID: 22425567. 7: 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. doi: 10.1016/s0014-5793(99)00128-3. PMID: 10069398. 8: 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. PMID: 21324322. 9: 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. doi: 10.1042/BJ20060706. PMID: 16831128; PMCID: PMC1615905. 10: 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. doi: 10.1038/nature02056. PMID: 14603310.