Genomic loci for this biosynthetic pathway

Cluster Type From To
The following clusters are from record BGC0001105.1:
Cluster 1NRP / Polyketide136513

BGC0001105, onnamide biosynthetic gene cluster from Candidatus Entotheonella sp.. Locus 1. Full MIBiG entry.

Chemical compounds

Compound: Onnamide A
PubChem ID: 10373128
SMILES string: Copy to clipboard
Molecular formula: C39H63N5O12
Average molecular mass: 793.956 Da
Molecular activity: Cytotoxic
Molecular target: inhibition of protein biosynthesis caused by binding to the ribosome. This mechanism causes a ribotoxic stress response and ultimately apoptosis.

Class-specific details

Biosynthetic class(es):
NRP / Polyketide
Other (linear)
Thioesterase type:
None
Release / cyclization type:
Hydrolysis

Nonribosomal peptide synthetases:
onnI (AAV97877.1)
Module 5
A specificity: Glycine
Evidence for specificity: Sequence-based prediction
C domain subtype: LCL
n.a.
Module 14
A specificity: Arginine
Evidence for specificity: Sequence-based prediction
C domain subtype: LCL
Polyketide subclass:
Other (linear)
Polyketide synthase subclass:
Trans-AT type I
Starter unit:
Acetyl-CoA
NONE
Thioesterase type:
Type I
Release / cyclization type:
Hydrolysis

Modular polyketide synthases:
onnB (AAV97870.1)
Module 0
Scaffold-modifying domain: GNAT
Module 1
KR stereochemistry: D-OH
Scaffold-modifying domain: Methylation
Module 2
Scaffold-modifying domain: 2x Crotonase / Enoyl-CoA dehydratase
Module 3
Scaffold-modifying domain: None

onnI (AAV97877.1)
Module 10
KR stereochemistry: D-OH
Scaffold-modifying domain: None
Module 11
Scaffold-modifying domain: None
Module is non-elongating
Evidence for non-elongation: Unknown
Module 4
Scaffold-modifying domain: None
Module is non-elongating
Evidence for non-elongation: Unknown
Module 6
KR stereochemistry: D-OH
Scaffold-modifying domain: None
Module 7
KR stereochemistry: D-OH
Scaffold-modifying domain: Methylation
Module 8
KR stereochemistry: D-OH
Scaffold-modifying domain: Pyran synthase
Module 9
KR stereochemistry: L-OH
Scaffold-modifying domain: None

no accession available
Module 11
Scaffold-modifying domain: None
Module is non-elongating
Evidence for non-elongation: Unknown
Module 12
Scaffold-modifying domain: None
Module 13
KR stereochemistry: D-OH
Scaffold-modifying domain: None

Gene cluster description

onnamide (BGC0001105). Gene Cluster 1. Biosynthetic class = NRP/Polyketide. GenBank AY688304. 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?incomplete
Evidence for cluster-compound connection:Sequence-based prediction
MIxS-compliance:Unknown
Comments:The gene cluster encodes for all onnamides, theopederins and pseudoonnamides.
Contact for this cluster:Eric J. N. Helfrich (Institute of Microbiology, Eidgenoessische Technische Hochschule (ETH) Zurich, Piel lab)

Literature references

1. Piel J et al. (2004) Antitumor polyketide biosynthesis by an uncultivated bacterial symbiont of the marine sponge Theonella swinhoei. Proc Natl Acad Sci U S A 101(46):16222-7. doi:
2. Wilson MC et al. (2014) An environmental bacterial taxon with a large and distinct metabolic repertoire. Nature 506(7486):58-62. doi: 10.1038/nature12959. Epub 2014 Jan 29.
3. Piel J. (2010) Biosynthesis of polyketides by trans-AT polyketide synthases. Nat Prod Rep 27(7):996-1047. doi: 10.1039/b816430b. Epub 2010 May 12.
4. Lee KH et al. (2005) Inhibition of protein synthesis and activation of stress-activated protein kinases by onnamide A and theopederin B, antitumor marine natural products. Cancer Sci 96(6):357-64. doi: 10.1111/j.1349-7006.2005.00055.x.
5. Shigeki Matsunaga, Nobuhiro Fusetani, Youichi Nakao. (1992) Eight new cytotoxic metabolites closely related to onnamide A from two marine sponges of the genus Theonella. Tetrahedron, vol. 48, no. 39, pp. 8369-8376
6. Sachiko Tsukamoto, Shigeki Matsunaga, Nobuhiro Fusetani, Akio Toh-e. (1999) Theopederins F-J: Five new antifungal and cytotoxic metabolites from the marine sponge, theonella swinhoei. Tetrahedron, vol. 55, no. 48, pp. 13697-13702
7. Shinichi. Sakemi, Toshio. Ichiba, Shigeo. Kohmoto, Gabriel. Saucy, Tatsuo. Higa. (1988) Isolation and structure elucidation of onnamide A, a new bioactive metabolite of a marine sponge, Theonella sp. Journal of the American Chemical Society, vol. 110, no. 14, pp. 4851-4853