Genomic loci for this biosynthetic pathway

Cluster Type From To
The following clusters are from record BGC0000168.1:
Cluster 1Polyketide151400

BGC0000168, viridicatumtoxin biosynthetic gene cluster from Penicillium aethiopicum. Locus 1. Full MIBiG entry.

Chemical compounds

Compound: viridicatumtoxin
PubChem ID: 54679209
SMILES string: Copy to clipboard
Molecular formula: C30H31NO10
Average molecular mass: 565.575 Da
Molecular activity: Antibacterial
Molecular target: undecaprenyl diphosphate synthase

Class-specific details

Biosynthetic class(es):
Polyketide
Polyketide subclass:
Tetracycline (cyclic)
Polyketide synthase subclass:
Iterative type I
Starter unit:
Malonamyl-CoA
Polyketide synthase / ketosynthase-encoding genes:
ADI24926
Iterative PKS subtype:
Non-reducing
Number of iterations:
8
C6-C11 first
Thioesterase type:
other
Release / cyclization type:
Claisen condensation

Gene cluster description

viridicatumtoxin (BGC0000168). Gene Cluster 1. Biosynthetic class = Polyketide. GenBank GU574477, positions 6230-40800. 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, Enzymatic assays, Proven expression in natural host
MIxS-compliance:Unknown
Contact for this cluster:Yit-Heng Chooi (The Australian National University)

Literature references

1. Chooi YH et al. (2010) Identification of the viridicatumtoxin and griseofulvin gene clusters from Penicillium aethiopicum. Chem Biol 17(5):483-94. doi: 10.1016/j.chembiol.2010.03.015.
2. Chooi YH et al. (2012) Discovery and characterization of a group of fungal polycyclic polyketide prenyltransferases. J Am Chem Soc 134(22):9428-37. doi: 10.1021/ja3028636. Epub 2012 May
3. Chooi YH et al. (2013) A cytochrome P450 serves as an unexpected terpene cyclase during fungal meroterpenoid biosynthesis. J Am Chem Soc 135(45):16805-8. doi: 10.1021/ja408966t. Epub 2013 Nov
4. Zheng CJ et al. (2008) Viridicatumtoxin B, a new anti-MRSA agent from Penicillium sp. FR11. J Antibiot (Tokyo) 61(10):633-7. doi: 10.1038/ja.2008.84.
5. Inokoshi J et al. (2013) Spirohexalines, new inhibitors of bacterial undecaprenyl pyrophosphate synthase, produced by Penicillium brasilianum FKI-3368. J Antibiot (Tokyo) 66(1):37-41. doi: 10.1038/ja.2012.83. Epub 2012 Nov
6. Nicolaou KC et al. (2013) Total synthesis and structural revision of viridicatumtoxin B. Angew Chem Int Ed Engl 52(33):8736-41. doi: 10.1002/anie.201304691.
7. Nicolaou KC et al. (2014) Total synthesis of viridicatumtoxin B and analogues thereof: strategy evolution, structural revision, and biological evaluation. J Am Chem Soc 136(34):12137-60. doi: 10.1021/ja506472u. Epub 2014