Genomic loci for this biosynthetic pathway

Cluster Type From To
The following clusters are from record BGC0000173.1:
Cluster 1Polyketide167546

BGC0000173, bongkrekic acid biosynthetic gene cluster from Burkholderia gladioli. Locus 1. Full MIBiG entry.

Chemical compounds

Compound: bongkrekic acid
PubChem ID: 5381207
ChemSpider ID: 4938689
SMILES string: Copy to clipboard
Molecular formula: C28H38O7
Average molecular mass: 486.605 Da
Molecular activity: Cytotoxic, Inhibitor
Molecular target: adenine nucleotide translocase

Class-specific details

Biosynthetic class(es):
Polyketide
Polyketide subclass:
Polyene (linear)
Polyketide synthase subclass:
Modular type I
Starter unit:
Acetyl-CoA
Thioesterase type:
None
Release / cyclization type:
Unknown

Modular polyketide synthases:
bonA (AFN27480.1)
Module 0
AT specificity: Malonyl-CoA
Evidence for specificity: Sequence-based prediction
Module 1
Scaffold-modifying domain: Beta-branching
Module 2
KR stereochemistry: A-group
Scaffold-modifying domain: Methylation
Module 3
KR stereochemistry: A-group
Module 4
KR stereochemistry: B-group
Module 5
KR stereochemistry: A-group
Module 6
Module is skipped
Evidence for skipping: Sequence-based prediction

bonB (AFN27481.1)
Module 6
Module 7
KR stereochemistry: B-group
Module 8
KR stereochemistry: B-group

bonC (AFN27482.1)
Module 8
Module 9
KR stereochemistry: B-group
Scaffold-modifying domain: Methylation

bonD (AFN27483.1)
Module 9
Scaffold-modifying domain: Methylation
Module 10
KR stereochemistry: B-group
Module 11
Scaffold-modifying domain: Beta-branching

Gene cluster description

bongkrekic acid (BGC0000173). Gene Cluster 1. Biosynthetic class = Polyketide. GenBank JX173632. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

Domain annotation

Homologous known gene clusters

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Knock-out studies, Gene expression correlated with compound production, Sequence-based prediction
MIxS-compliance:Unknown
Contact for this cluster:Keishi Ishida (Leipniz Institute for Natural Product Research and Infection Biology)

Literature references

1. Moebius N et al. (2012) Biosynthesis of the respiratory toxin bongkrekic acid in the pathogenic bacterium Burkholderia gladioli. Chem Biol 19(9):1164-74. doi: 10.1016/j.chembiol.2012.07.022.
2. Rohm B et al. (2010) Biosynthesis of the mitochondrial adenine nucleotide translocase (ATPase) inhibitor bongkrekic acid in Burkholderia gladioli. Org Biomol Chem 8(7):1520-2. doi: 10.1039/b925483h. Epub 2010 Feb 5.
3. Zylber J et al. (1973) [The absolute configuration of bongkrekic acid]. Experientia 29(6):648-9.
4. Klingenberg M. (2008) The ADP and ATP transport in mitochondria and its carrier. Biochim Biophys Acta 1778(10):1978-2021. doi:
5. Coenye T et al. (1999) Burkholderia cocovenenans (van Damme et al. 1960) Gillis et al. 1995 and Burkholderia vandii Urakami et al. 1994 are junior synonyms of Burkholderia gladioli (Severini 1913) Yabuuchi et al. 1993 and Burkholderia plantarii (Azegami et al. 1987) Urakami et al. 1994, respectively. Int J Syst Bacteriol 49 Pt 1:37-42. doi: 10.1099/00207713-49-1-37.
6. Lauquin GJ et al. (1976) Isobongkrekic acid, a new inhibitor of mitochondrial ADP-ATP transport: radioactive labeling and chemical and biological properties. Biochemistry 15(11):2323-7.