bongkrekic acid
CHEBI:77742 EXACT SEEDED
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.
Structure
| Standard InChIKey | SHCXABJSXUACKU-WUTQZGRKSA-N |
|---|---|
| SMILES | C[C@@H](C/C=C/CC/C=C/C=C\C[C@H](/C(=C\C=C(/C)\C(=O)O)/C)OC)/C=C/C(=C\C(=O)O)/CC(=O)O |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA017560 |
Filing pathway
Fatty acids — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is pks, from MIBiG.
Producer organisms 1
A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.
| Taxon | Basis | Cluster | Evidence |
|---|---|---|---|
| Burkholderia gladioli NCBITaxon:28095 |
BGC_CHARACTERIZED | mibig:BGC0000173 | PMID:22999884 |
Occurrences 4
Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.
| Taxon | Source | Reference |
|---|---|---|
| Burkholderia gladioli NCBITaxon:28095 |
LOTUS | DOI:10.1002/RECL.19570760103 |
| Burkholderia gladioli NCBITaxon:28095 |
LOTUS | DOI:10.1016/J.CHEMBIOL.2012.07.022 |
| Burkholderia gladioli NCBITaxon:28095 |
LOTUS | DOI:10.1021/BI00656A012 |
| Burkholderia gladioli NCBITaxon:28095 |
CHEBI | PMID:28105575 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000173 | Burkholderia gladioli NCBITaxon:28095 |
CLUSTER_DEMONSTRATED | genbank:JX173632.1 |
A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.
Open questions 1
name-disagreement — ChEBI calls this structure 'bongkrekic acid' and MIBiG calls it 'isobongkrekic acid'. They share a Standard InChIKey, so if the names denote different compounds then one upstream record has the wrong structure. Check which.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000173 | MIBIG | 5 |
| CHEBI:77742 | CHEBI | 3-star |
This page is generated from data/natural_products/fatty_acids/bongkrekic-acid.yaml, which is generated from the committed inventories. Neither is edited by hand.