CHEBI:166872 - nucleocidin

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ChEBI Name nucleocidin
ChEBI ID CHEBI:166872
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Martin Larralde
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Formula C10H13FN6O6S
Net Charge 0
Average Mass 364.310
Monoisotopic Mass 364.06013
InChI InChI=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
InChIKey LTBCQBSAWAZBDF-MLTZYSBQSA-N
SMILES NC1=C2N=CN([C@@H]3O[C@](F)(COS(N)(=O)=O)[C@@H](O)[C@H]3O)C2=NC=N1
Metabolite of Species Details
Streptomyces asterosporus (NCBI:txid285570) of strain DSM 41452 See: PubMed
Streptomyces calvus (NCBI:txid67282) of strain ATCC 13382 See: PubMed
Streptomyces calvus (NCBI:txid67282) of strain T-3018 See: PubMed
Roles Classification
Biological Role(s): trypanocidal drug
A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.
protein synthesis inhibitor
A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
nucleoside antibiotic

bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
Application(s): trypanocidal drug
A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.
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ChEBI Ontology
Outgoing 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 Sources
4'-C-fluoroadenosine 5'-sulfamate ChemIDplus
4'-fluoro-5'-O-sulfamoyladenosine ChemIDplus
4'-fluoro-5'-O-sulphamoyladenosine MetaCyc
[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-fluoro-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate ChEBI
[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-fluoro-3,4-dihydroxyoxolan-2-yl]methyl sulfamate ChEBI
antibiotic T-3018 ChemIDplus
T-3018 ChemIDplus
Manual Xrefs Databases
65250 ChemSpider
CPD-12712 MetaCyc
Nucleocidin Wikipedia
View more database links
Registry Number Type Source
24751-69-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
1085509 PubMed citation Europe PMC
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Last Modified
29 January 2021