Genomic loci for this biosynthetic pathway

Cluster Type From To
The following clusters are from record BGC0000070.1:
Cluster 1Polyketide155000

BGC0000070, griseofulvin biosynthetic gene cluster from Penicillium aethiopicum. Locus 1. Full MIBiG entry.

Chemical compounds

Compound: griseofulvin
PubChem ID: 441140
SMILES string: Copy to clipboard
Molecular formula: C17H17ClO6
Average molecular mass: 352.767 Da
Molecular activity: Antifungal, Cytotoxic
Molecular target: microtubule protein

Class-specific details

Biosynthetic class(es):
Polyketide
Polyketide subclass:
Polyphenol (cyclic)
Polyketide synthase subclass:
Iterative type I
Starter unit:
Acetyl-CoA
Polyketide synthase / ketosynthase-encoding genes:
ADI24953
Iterative PKS subtype:
Non-reducing
Number of iterations:
6
Other
Thioesterase type:
None
Release / cyclization type:
Claisen condensation

Gene cluster description

griseofulvin (BGC0000070). Gene Cluster 1. Biosynthetic class = Polyketide. GenBank GU574478, positions 9800-36750. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

Domain annotation

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Knock-out studies, Enzymatic assays, Heterologous expression, Proven expression in natural host
MIxS-compliance:Unknown
Contact for this cluster:Yit-Heng Chooi (The Australian National University)

Literature references

1. Cacho RA et al. (2013) Complexity generation in fungal polyketide biosynthesis: a spirocycle-forming P450 in the concise pathway to the antifungal drug griseofulvin. ACS Chem Biol 8(10):2322-30. doi: 10.1021/cb400541z. Epub 2013 Sep
2. Raab MS et al. (2012) GF-15, a novel inhibitor of centrosomal clustering, suppresses tumor cell growth in vitro and in vivo. Cancer Res 72(20):5374-85. doi: 10.1158/0008-5472.CAN-12-2026. Epub
3. Ronnest MH et al. (2012) Disparate SAR data of griseofulvin analogues for the dermatophytes Trichophyton mentagrophytes, T. rubrum, and MDA-MB-231 cancer cells. J Med Chem 55(2):652-60. doi: 10.1021/jm200835c. Epub 2012 Jan 17.
4. 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.
5. Panda D et al. (2005) Kinetic suppression of microtubule dynamic instability by griseofulvin: implications for its possible use in the treatment of cancer. Proc Natl Acad Sci U S A 102(28):9878-83. doi:
6. Roobol A et al. (1977) Griseofulvin-induced aggregation of microtubule protein. Biochem J 167(1):39-43.
7. Wehland J et al. (1977) Interaction of griseofulvin with microtubules, microtubule protein and tubulin. J Mol Biol 111(3):329-42.
8. Grisham LM et al. (1973) Antimitotic action of griseofulvin does not involve disruption of microtubules. Nature 244(5414):294-6.