Carboxyatractyloside

Carboxyatractyloside
Names
	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

Carboxyatractyloside (CATR) is a highly toxic diterpene glycoside that inhibits the ADP/ATP translocase. It's about 10 times more potent than atractyloside.[1] While atractyloside is effective in the inhibition of oxidative phosphorylation, carboxyatractyloside is considered to be more effective. As well when carboxyatractyloside is inhibited, it is not reversed by increasing the concentration of adenine nucleotides unlike its counterpart atractyloside. Carboxyatractyloside behavior resembles bongkrekic acid while in the mitochondria.[2]

References

Kedrov A, Hellawell AM, Klosin A, Broadhurst RB, Kunji ER, Müller DJ (January 2010). "Probing the interactions of carboxy-atractyloside and atractyloside with the yeast mitochondrial ADP/ATP carrier". Structure. 18 (1): 39–46. doi:10.1016/j.str.2009.11.009. PMID 20152151.
Luciani S, Martini N, Santi R (September 1971). "Effects of carboxyatractyloside a structural analogue of atractyloside on mitochondrial oxidative phosphorylation". Life Sciences. 10 (17, Pt 2): 961–8. doi:10.1016/0024-3205(71)90099-3. PMID 4255019.

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[1] Kedrov A, Hellawell AM, Klosin A, Broadhurst RB, Kunji ER, Müller DJ (January 2010). "Probing the interactions of carboxy-atractyloside and atractyloside with the yeast mitochondrial ADP/ATP carrier". Structure. 18 (1): 39–46. doi:10.1016/j.str.2009.11.009. PMID 20152151.

[2] Luciani S, Martini N, Santi R (September 1971). "Effects of carboxyatractyloside a structural analogue of atractyloside on mitochondrial oxidative phosphorylation". Life Sciences. 10 (17, Pt 2): 961–8. doi:10.1016/0024-3205(71)90099-3. PMID 4255019.