Carboxyatractyloside

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]

Carboxyatractyloside

Names
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
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
Identifiers
CAS Number	33286-30-5
3D model (JSmol)	Interactive image
ChemSpider	16737649
DrugBank	DB02426
EC Number	251-444-9
PubChem CID	20055804
UNII	SNP1XL23E6
InChI 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 Key: AQFATIOBERWBDY-LNQSNDDKSA-N
SMILES CC(CC(=O)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@@]([C@@H]3[C@@](C2)([C@H]4[C@@]5([C@H](C(=C)[C@@H](C5)CC4)O)CC3)C)(C(=O)O)C(=O)O)C
Properties
Chemical formula	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). Infobox references

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]