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CHEBI:77742 - bongkrekic acid

ChEBI IDCHEBI:77742
ChEBI Namebongkrekic acid
Stars
DefinitionA tricarboxylic acid that is docosa-2,4,8,10,14,18,20-heptaenedioic acid substituted at positions 2 ,5 and 17 by methyl groups, at positions 6 by a methoxy group and at position 20 by a carboxymethyl group. It is produced by the bacterium Burkholderia gladioli and implicated in outbreaks of food-borne illness involving coconut and corn-based products in Indonesia and China.
Last Modified7 September 2021
SubmitterSteve
DownloadsMolfile
FormulaC28H38O7
Net Charge0
Average Mass486.605
Monoisotopic Mass486.26175
SMILESCO[C@H](C/C=C\C=C\CC/C=C/C[C@H](C)/C=C/C(=C\C(=O)O)CC(=O)O)/C(C)=C\C=C(/C)C(=O)O
InChIInChI=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
InChIKeySHCXABJSXUACKU-WUTQZGRKSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Burkholderia gladioli (ncbitaxon:28095) - PubMed (28105575) Species also known as Pseudomonas cocovenenans.
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
toxin  Poisonous substance produced by a biological organism such as a microbe, animal or plant.
ATP/ADP translocase inhibitor  Any inhibitor of the trasporter protein ATP/ADP translocase.
apoptosis inhibitor  Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
EC 2.5.1.18 (glutathione transferase) inhibitor  An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of a glutathione transferase (EC 2.5.1.18).
ChEBI Ontology
Outgoing Relation(s)
bongkrekic acid (CHEBI:77742) has role apoptosis inhibitor (CHEBI:68494)
bongkrekic acid (CHEBI:77742) has role ATP/ADP translocase inhibitor (CHEBI:77750)
bongkrekic acid (CHEBI:77742) has role bacterial metabolite (CHEBI:76969)
bongkrekic acid (CHEBI:77742) has role EC 2.5.1.18 (glutathione transferase) inhibitor (CHEBI:76797)
bongkrekic acid (CHEBI:77742) has role toxin (CHEBI:27026)
bongkrekic acid (CHEBI:77742) is a ether (CHEBI:25698)
bongkrekic acid (CHEBI:77742) is a olefinic compound (CHEBI:78840)
bongkrekic acid (CHEBI:77742) is a tricarboxylic acid (CHEBI:27093)
bongkrekic acid (CHEBI:77742) is conjugate acid of bongkrekate(3−) (CHEBI:178020)
Incoming Relation(s)
bongkrekate(3−) (CHEBI:178020) is conjugate base of bongkrekic acid (CHEBI:77742)
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
Synonyms  Source
(2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)-20-(carboxymethyl)-6-methoxy-2,5,17-trimethyl-2,4,8,10,14,18,20-docosaheptaenedioic acidChEBI
bongkrek acidPDBeChem
(−)-bongkrekic acidChEBI
Manual XrefsDatabases
4938689ChemSpider
BKCPDBeChem
Bongkrek_acidWikipedia
JP2005068064Patent
Registry NumbersSources
Reaxys:1717902Reaxys
CAS:11076-19-0ChemIDplus
Citations