Genomic loci for this biosynthetic pathway

Cluster Type From To
The following clusters are from record BGC0000101.1:
Cluster 1Polyketide15712

BGC0000101, monodictyphenone biosynthetic gene cluster from Aspergillus nidulans. Locus 1. Full MIBiG entry.

Chemical compounds

Compound: emodin
PubChem ID: 3220
SMILES string: Copy to clipboard
Molecular formula: C15H10O5
Average molecular mass: 270.24 Da
Molecular activity: Inhibitor
Molecular target: STAT3

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:
Iterative PKS subtype:
Non-reducing
Number of iterations:
7
C6-C11 first
Thioesterase type:
Other
Release / cyclization type:
Hydrolysis

Modular polyketide synthases:
mdpG (CBF90097.1)
Module 1
AT specificity: Malonyl-CoA
Evidence for specificity: Structure-based inference
Scaffold-modifying domain: None
Module is iterated
Evidence for iteration: Unknown

Gene cluster description

monodictyphenone (BGC0000101). Gene Cluster 1. Biosynthetic class = Polyketide. GenBank BN001302, positions 441042-446753. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Knock-out studies, Enzymatic assays, Gene expression correlated with compound production, Sequence-based prediction
MIxS-compliance:Unknown
Contact for this cluster:Philipp Wiemann (University of Wisconsin-Madison)

Literature references

1. Bok JW et al. (2009) Chromatin-level regulation of biosynthetic gene clusters. Nat Chem Biol 5(7):462-4. doi: 10.1038/nchembio.177.
2. Chiang YM et al. (2010) Characterization of the Aspergillus nidulans monodictyphenone gene cluster. Appl Environ Microbiol 76(7):2067-74. doi: 10.1128/AEM.02187-09. Epub
3. Sanchez JF et al. (2011) Genome-based deletion analysis reveals the prenyl xanthone biosynthesis pathway in Aspergillus nidulans. J Am Chem Soc 133(11):4010-7. doi: 10.1021/ja1096682. Epub 2011 Feb
4. Simpson TJ. (2012) Genetic and biosynthetic studies of the fungal prenylated xanthone shamixanthone and related metabolites in Aspergillus spp. revisited. Chembiochem 13(11):1680-8. doi: 10.1002/cbic.201200014. Epub 2012
5. Schatzle MA et al. (2012) Tautomers of anthrahydroquinones: enzymatic reduction and implications for chrysophanol, monodictyphenone, and related xanthone biosyntheses. J Am Chem Soc 134(36):14742-5. doi: 10.1021/ja307151x. Epub 2012 Aug
6. Subramaniam A et al. (2013) Emodin inhibits growth and induces apoptosis in an orthotopic hepatocellular carcinoma model by blocking activation of STAT3. Br J Pharmacol 170(4):807-21. doi: 10.1111/bph.12302.