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CHEBI:140651 - rhabduscin

ChEBI IDCHEBI:140651
ChEBI Namerhabduscin
Stars
DefinitionAn 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.
Last Modified5 September 2019
SubmitterKristian Axelsen
DownloadsMolfile
FormulaC17H20N2O5
Net Charge0
Average Mass332.356
Monoisotopic Mass332.13722
SMILES[C-]#[N+]/C=C/c1ccc(O[C@H]2O[C@@H](C)[C@@H](NC(C)=O)[C@@H](O)[C@@H]2O)cc1
InChIInChI=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
InChIKeyWQBVZBBQNNMLLX-YFFNFLMJSA-N
Species of MetaboliteComponentSourceComments
Xenorhabdus nematophila (ncbitaxon:628) - PubMed (22711807)
Photorhabdus luminescens (ncbitaxon:29488) - PubMed (22711807)
Roles Classification
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
EC 1.14.18.1 (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 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.
ChEBI Ontology
Outgoing Relation(s)
rhabduscin (CHEBI:140651) has role bacterial metabolite (CHEBI:76969)
rhabduscin (CHEBI:140651) has role EC 1.14.18.1 (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)
IUPAC Name 
4-[(E)-2-isocyanovinyl]phenyl 4-acetamido-4,6-dideoxy-β-L-galactopyranoside
Manual XrefsDatabases
CPD-20771MetaCyc
Citations