Names | |
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IUPAC name
15α-Hydroxy-2β-[2-O-(3-methylbutanoyl)-3,4-di-O-sulfono-β-D-glucopyranosyloxy]-5β,8α,9β,10α,13α-kaur-16-ene-18,19-dioic acid
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Systematic IUPAC name
(2S,4aS,6aR,7S,9R,11aS,11bS)-7-Hydroxy-2-({(2R,3R,4R,5R,6R)-6-(hydroxymethyl)-3-[(3-methylbutanoyl)oxy]oxan-2-yl}oxy)-11b-methyl-8-methylidenedodecahydro-6a,9-methanocyclohepta[a]naphthalene-4,4(1H)-dicarboxylic acid | |
Other names
CATR
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
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EC Number |
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PubChem CID
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UNII | |
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Properties | |
C31H46O18S2 | |
Molar mass | 770.81 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Carboxyatractyloside (CATR) is a highly toxic diterpene glycoside that inhibits the ADP/ATP translocase. It is about 10 times more potent than its analog atractyloside.[1] While atractyloside is effective in the inhibition of oxidative phosphorylation, carboxyatractyloside is considered to be more effective.[2] The effects of carboxyatractyloside on the ADP/ATP translocase are not reversed by increasing the concentration of adenine nucleotides, unlike its counterpart atractyloside.[2] Carboxyatractyloside behavior resembles bongkrekic acid while in the mitochondria.[2] Carboxyatractyloside is poisonous to humans as well as livestock, including cows[3] and horses.[4]
Symptoms of carboxyatractyloside poisoning may include abdominal pain, nausea and vomiting, drowsiness, palpitations, sweating and trouble breathing.[5] In severe cases, convulsions, liver failure and loss of consciousness may develop, which can lead to death.[5]
Carboxyatractyloside can be found in Xanthium species plants, including Xanthium strumarium.[6] Consumption of Xanthium containing the toxin led to the deaths of at least 19 people in Sylhet, Bangladesh during a period of food scarcity.[7] Along with atractyloside, it is also one of the main poisonous substances in the Atractylis gummifera thistle.[8]