rhabduscin
CHEBI:140651 EXACT SEEDED
An isocyanide that is the 4-acetamido-4,6-dideoxy-β-L-galactopyranoside of p-[(E)-2-isocyanovinyl]phenol. Produced by the gram-negative insect pathogens, Xenorhabdus nematophila and Photorhabdus luminescens, it is a potent nanomolar-level inhibitor of phenoloxidase, a key component of the insect's innate immune system.
Structure
| Standard InChIKey | WQBVZBBQNNMLLX-YFFNFLMJSA-N |
|---|---|
| SMILES | C[C@H]1[C@H]([C@H]([C@@H]([C@H](O1)OC2=CC=C(C=C2)/C=C/[N+]#[C-])O)O)NC(=O)C |
| Stereochemistry | fully defined |
| Cross-references | pubchem:102453304 |
Filing pathway
Unclassified — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is other, from MIBiG.
Producer organisms 1
A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.
| Taxon | Basis | Cluster | Evidence |
|---|---|---|---|
| Xenorhabdus nematophila ATCC 19061 NCBITaxon:406817 |
SOURCE_ASSERTION | mibig:BGC0001757 | PMID:20022247 |
Occurrences 2
Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.
| Taxon | Source | Reference |
|---|---|---|
| Photorhabdus luminescens NCBITaxon:29488 |
CHEBI | PMID:22711807 |
| Xenorhabdus nematophila NCBITaxon:628 |
CHEBI | PMID:22711807 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0001757 | Xenorhabdus nematophila ATCC 19061 NCBITaxon:406817 |
CLUSTER_UNSTATED | genbank:FN667742.1 |
A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0001757 | MIBIG | 3 |
| CHEBI:140651 | CHEBI | 3-star |
This page is generated from data/natural_products/unclassified/rhabduscin.yaml, which is generated from the committed inventories. Neither is edited by hand.