CHEBI:77742 - bongkrekic acid

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ChEBI Name bongkrekic acid
ChEBI ID CHEBI:77742
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C28H38O7
Net Charge 0
Average Mass 486.605
Monoisotopic Mass 486.26175
InChI 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
InChIKey SHCXABJSXUACKU-WUTQZGRKSA-N
SMILES CO[C@H](C\C=C/C=C/CC\C=C\C[C@H](C)\C=C\C(\CC(O)=O)=C/C(O)=O)C(\C)=C/C=C(\C)C(O)=O
Metabolite of Species Details
Burkholderia gladioli (NCBI:txid28095) Species also known as Pseudomonas cocovenenans. See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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).
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.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
(−)-bongkrekic acid ChEBI
(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 acid ChEBI
bongkrek acid PDBeChem
Manual Xrefs Databases
4938689 ChemSpider
BKC PDBeChem
Bongkrek_acid Wikipedia
JP2005068064 Patent
View more database links
Registry Numbers Types Sources
11076-19-0 CAS Registry Number ChemIDplus
1717902 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
07 September 2021