Bongkrekic Acid

Bongkrekic acid is polyketide and bacterial toxin that has been found in B. gladioli. It is an inhibitor of ADP/ATP translocase (AAT), a carrier protein that imports ADP into the mitochondrial matrix and exports ATP into the intermembrane space. It prevents ADP import and inhibits mitochondrial respiration (Ki = 20 nM in isolated rat liver mitochondria). Bongkrekic acid induces cell death in MCF-7 human breast cancer cells deprived of estradiol for six months (EC50 = 2.58 µM). It is toxic to mice (LD50s = 0.68-6.84 mg/kg, p.o.).Formal Name: 20-(carboxymethyl)-6R-methoxy-2,5,17S-trimethyl-2E,4Z,8Z,10E,14E,18E,20Z-docosaheptaenedioic acid. CAS Number: 11076-19-0. Synonyms: Bongkrek Acid. Molecular Formula: C28H38O7. Formula Weight: 486.6. Purity: >98%. Formulation: (Request formulation change), A solution in 0.01M Tris buffer pH 7.5. Solubility: DMSO: Miscible. SMILES: OC(/C=C(CC(O)=O)\C=C\[C@@H](C)C/C=C/CC/C=C/C=C\C[C@@H](OC)/C(C)=C\C=C(C(O)=O)/C)=O. InChi Code: InChI=1S/C28H38O7/c1-21(15-18-24(19-26(29)30)20-27(31)32)13-11-9-7-5-6-8-10-12-14-25(35-4)22(2)16-17-23(3)28(33)34/h6,8-12,15-19,21,25H,5,7,13-14,20H2,1-4H3,(H,29,30)(H,31,32)(H,33,34)/b8-6+,11-9+,12-10-,18-15+,22-16-,23-17+,24-19+/t21-,25+/m0/s1. InChi Key: SHCXABJSXUACKU-WUTQZGRKSA-N. Origin: Bacterium/Pseudomonas gladioli.