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CHEBI:166872 - nucleocidin

ChEBI IDCHEBI:166872
ChEBI Namenucleocidin
Stars
DefinitionA nucleoside antibiotic that is 5'-O-sulfamoyladenosine in which the hydrogen atom at position 4' is replaced by a fluorine atom. It is a natural product synthesized by several Streptomyces species. It exhibits broad spectrum antibacterial activity, and also has a strong effect against Trypanosoma brucei, the protozoan parasite responsible for the African sleeping sickness.
Last Modified29 January 2021
SubmitterMartin Larralde
DownloadsMolfile
FormulaC10H13FN6O6S
Net Charge0
Average Mass364.315
Monoisotopic Mass364.06013
SMILESNc1ncnc2c1ncn2[C@@H]1O[C@](F)(COS(N)(=O)=O)[C@@H](O)[C@H]1O
InChIInChI=1S/C10H13FN6O6S/c11-10(1-22-24(13,20)21)6(19)5(18)9(23-10)17-3-16-4-7(12)14-2-15-8(4)17/h2-3,5-6,9,18-19H,1H2,(H2,12,14,15)(H2,13,20,21)/t5-,6+,9-,10-/m1/s1
InChIKeyLTBCQBSAWAZBDF-MLTZYSBQSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Streptomyces asterosporus (ncbitaxon:285570) - PubMed (30641108) Strain: DSM 41452
Streptomyces calvus (ncbitaxon:67282)
- PubMed (26374477) Strain: ATCC 13382
- PubMed (32110306) Strain: T-3018
Roles Classification
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
protein synthesis inhibitor  A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
trypanocidal drug  A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
Application:
trypanocidal drug  A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.
ChEBI Ontology
Outgoing Relation(s)
nucleocidin (CHEBI:166872) has functional parent adenosine (CHEBI:16335)
nucleocidin (CHEBI:166872) has role antibacterial agent (CHEBI:33282)
nucleocidin (CHEBI:166872) has role bacterial metabolite (CHEBI:76969)
nucleocidin (CHEBI:166872) has role nucleoside antibiotic (CHEBI:25605)
nucleocidin (CHEBI:166872) has role protein synthesis inhibitor (CHEBI:48001)
nucleocidin (CHEBI:166872) has role trypanocidal drug (CHEBI:36335)
nucleocidin (CHEBI:166872) is a 6-aminopurines (CHEBI:20706)
nucleocidin (CHEBI:166872) is a adenosines (CHEBI:22260)
nucleocidin (CHEBI:166872) is a diol (CHEBI:23824)
nucleocidin (CHEBI:166872) is a organofluorine compound (CHEBI:37143)
nucleocidin (CHEBI:166872) is a sulfamate ester (CHEBI:48199)
IUPAC Name 
[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-fluoro-3,4-dihydroxyoxolan-2-yl]methyl sulfamate
Synonyms  Source
[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-fluoro-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamateChEBI
[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-fluoro-3,4-dihydroxyoxolan-2-yl]methyl sulfamateChEBI
4'-C-fluoroadenosine 5'-sulfamateChemIDplus
4'-fluoro-5'-O-sulfamoyladenosineChemIDplus
4'-fluoro-5'-O-sulphamoyladenosineMetaCyc
antibiotic T-3018ChemIDplus
Manual XrefsDatabases
65250ChemSpider
CPD-12712MetaCyc
NucleocidinWikipedia
Registry NumbersSources
CAS:24751-69-7ChemIDplus
Citations