CHEBI:140651 - rhabduscin

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ChEBI Name rhabduscin
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information
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Formula C17H20N2O5
Net Charge 0
Average Mass 332.356
Monoisotopic Mass 332.13722
InChI InChI=1S/C17H20N2O5/c1-10-14(19-11(2)20)15(21)16(22)17(23-10)24-13-6-4-12(5-7-13)8-9-18-3/h4-10,14-17,21-22H,1-2H3,(H,19,20)/b9-8+/t10-,14+,15+,16-,17+/m0/s1
SMILES C(\[N+]#[C-])=C/C1=CC=C(C=C1)O[C@@H]2[C@H]([C@@H]([C@@H]([C@@H](O2)C)NC(C)=O)O)O
Metabolite of Species Details
Photorhabdus luminescens (NCBI:txid29488) See: PubMed
Xenorhabdus nematophila (NCBI:txid628) See: PubMed
Roles Classification
Biological Role(s): EC (tyrosinase) inhibitor
Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
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ChEBI Ontology
Outgoing rhabduscin (CHEBI:140651) has role bacterial metabolite (CHEBI:76969)
rhabduscin (CHEBI:140651) has role EC (tyrosinase) inhibitor (CHEBI:59997)
rhabduscin (CHEBI:140651) is a acetamides (CHEBI:22160)
rhabduscin (CHEBI:140651) is a isocyanide (CHEBI:35353)
rhabduscin (CHEBI:140651) is a olefinic compound (CHEBI:78840)
4-[(E)-2-isocyanovinyl]phenyl 4-acetamido-4,6-dideoxy-β-L-galactopyranoside
Manual Xref Database
CPD-20771 MetaCyc
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Citations Waiting for Citations Types Sources
22711807 PubMed citation SUBMITTER
26681201 PubMed citation Europe PMC
30376630 PubMed citation Europe PMC
30794697 PubMed citation Europe PMC
Last Modified
05 September 2019