Genomic loci for this biosynthetic pathway

Cluster Type From To
The following clusters are from record BGC0001467.1:
Cluster 1NRP / Polyketide125782

BGC0001467, hapalosin biosynthetic gene cluster from Fischerella sp. PCC. Locus 1. Full MIBiG entry.

Chemical compounds

Compound: Hapalosin
PubChem ID: 133055
ChemSpider ID: 117421
SMILES string: Copy to clipboard
Molecular formula: C28H43NO6
Average molecular mass: 489.653 Da
Molecular activity: Cytotoxic, Other
Molecular target: P-glycoprotein

Class-specific details

Biosynthetic class(es):
NRP / Polyketide
Cyclic depsipeptide (cyclic)
Thioesterase type:
Type I
Release / cyclization type:
Hydrolysis

Nonribosomal peptide synthetases:
hapA (WP_026723805.1)
Module 0
A specificity: Unknown
Evidence for specificity: Unknown
C domain subtype: Starter
hapC (WP_081656241.1)
Module 2
A specificity: 2-Hydroxyisovalerate
Evidence for specificity: Structure-based inference
C domain subtype: LCL
hapD (WP_051206727.1)
Module 3
A specificity: Phenylalanine
Evidence for specificity: Structure-based inference
C domain subtype: LCL
Scaffold-modifying domain: Methylation
Polyketide subclass:
Other (cyclic)
Polyketide synthase subclass:
Modular type I
Starter unit:
Hexanoyl-ACP
Thioesterase type:
Type I
Release / cyclization type:
Hydrolysis

Modular polyketide synthases:
hapB (WP_035121546.1)
Module 1
AT specificity: Malonyl-CoA
Evidence for specificity: Structure-based inference
KR stereochemistry: Unknown
Scaffold-modifying domain: Methylation

hapE (WP_035122279.1)
Module 4
AT specificity: Malonyl-CoA
Evidence for specificity: Structure-based inference
KR stereochemistry: Unknown
Scaffold-modifying domain: None

Gene cluster description

hapalosin (BGC0001467). Gene Cluster 1. Biosynthetic class = NRP/Polyketide. GenBank Not derived from GenBank. 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:Heterologous expression, Sequence-based prediction
MIxS-compliance:Unknown
Contact for this cluster:Paul D'Agostino (Technical University of Munich)

Literature references

1. Klemens Stratmann, David L. Burgoyne, Richard E. Moore, Gregory M. L. Patterson, Charles D. Smith. (1994) Hapalosin, a Cyanobacterial Cyclic Depsipeptide with Multidrug-Resistance Reversing Activity. The Journal of Organic Chemistry, vol. 59, no. 24, pp. 7219-7226
2. Micallef ML et al. (2015) Genome mining for natural product biosynthetic gene clusters in the Subsection V cyanobacteria. BMC Genomics 16:669. doi: 10.1186/s12864-015-1855-z.
3. D'Agostino PM, Gulder TAM. (2018) Direct Pathway Cloning Combined with Sequence- and Ligation-Independent Cloning for Fast Biosynthetic Gene Cluster Refactoring and Heterologous Expression. ACS Synth Biol 7(7):1702-1708. doi: 10.1021/acssynbio.8b00151. Epub