13C28-Bongkrekic Acid

13C28-Bongkrekic Acid is intended for use as an internal standard for the quantification of bongkrekic acid (Cay-38230) by GC- or LC-MS. 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: (2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)-20-((carboxy-13C)methyl-13C)-6-(methoxy-13C)-2,5,17-tri(methyl-13C)docosa-2,4,8,10,14,18,20-heptaenedioic-1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22-13C22 acid. Synonyms: 13C28-Bongkrek Acid. Molecular Formula: [13C]28H38O7. Formula Weight: 514.4. Purity: >98%. Formulation: (Request formulation change), A 5 µg/ml solution in methanol. Solubility: Methanol: Soluble. SMILES: O[13C](/[13CH]=[13C]([13CH2][13C](O)=O)\[13CH]=[13CH]\[13C@@H]([13CH3])[13CH2]/[13CH]=[13CH]/[13CH2][13CH2]/[13CH]=[13CH]/[13CH]=[13CH]\[13CH2][13C@@H](O[13CH3])/[13C]([13CH3])=[13CH]\[13CH]=[13C]([13C](O)=O)/[13CH3])=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/i1+1,2+1,3+1,4+1,5+1,6+1,7+1,8+1,9+1,10+1,11+1,12+1,13+1,14+1,15+1,16+1,17+1,18+1,19+1,20+1,21+1,22+1,23+1,24+1,25+1,26+1,27+1,28+1. InChi Key: SHCXABJSXUACKU-LGIAGIHQSA-N. Origin: Synthetic.