Bongkrek acid

Bongkrek acid (also known as bongkrekic acid) is a respiratory toxin produced in fermented coconut or corn contaminated by the bacterium Burkholderia gladioli pathovar cocovenenans. It is a highly toxic, heat-stable, colorless, odorless, and highly unsaturated tricarboxylic acid that inhibits the ADP/ATP translocase, also called the mitochondrial ADP/ATP carrier, preventing ATP from leaving the mitochondria to provide metabolic energy to the rest of the cell. Bongkrek acid, when consumed through contaminated foods, mainly targets the liver, brain, and kidneys along with symptoms that include vomiting, diarrhea, urinary retention, abdominal pain, and excessive sweating. Most of the outbreaks are found in Indonesia and China where fermented coconut and corn-based foods are consumed.

Bongkrek acid
Names
Preferred IUPAC name
(2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)-20-(Carboxymethyl)-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid
Other names
Bongkrekic acid
Bongkrekik acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
MeSH Bongkrekic+acid
PubChem CID
UNII
  • 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) N
    Key: SHCXABJSXUACKU-UHFFFAOYSA-N N
  • InChI=1/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
    Key: SHCXABJSXUACKU-WUTQZGRKBG
  • 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
    Key: SHCXABJSXUACKU-WUTQZGRKSA-N
SMILES
  • COC(CC=CC=CCCC=CCC(C)C=CC(CC(O)=O)=CC(O)=O)C(C)=CC=C(C)C(O)=O
  • O=C(O)\C(=C\C=C(\C)[C@H](OC)C/C=C\C=C\CC/C=C/C[C@@H](/C=C/C(=C\C(=O)O)CC(=O)O)C)C
Properties
C28H38O7
Molar mass 486.605 g·mol−1
Appearance Odorless and colorless
Melting point 50 to 60 °C (122 to 140 °F; 323 to 333 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references
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