nucleocidin

CHEBI:166872 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:20706 CHEBI:20706
CHEBI:22260 CHEBI:22260
CHEBI:23824 CHEBI:23824
CHEBI:37143 CHEBI:37143
CHEBI:48199 CHEBI:48199

Chemical structure

Computed structure properties
Molecular formula	C10H13FN6O6S
Charge	0
Average mass	364.315 Da
Monoisotopic mass	364.06013 Da
Source	ChEBI
InChIKey	LTBCQBSAWAZBDF-MLTZYSBQSA-N

SMILES

Nc1ncnc2c1ncn2[C@@H]1O[C@](F)(COS(N)(=O)=O)[C@@H](O)[C@H]1O

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

Also called

[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-fluoro-3,4-dihydroxyoxolan-2-yl]methyl sulfamate (EXACT_SYNONYM)— chebi
4'-C-fluoroadenosine 5'-sulfamate (EXACT_SYNONYM)— chebi
4'-fluoro-5'-O-sulfamoyladenosine (EXACT_SYNONYM)— chebi
4'-fluoro-5'-O-sulphamoyladenosine (EXACT_SYNONYM)— chebi
T-3018 (EXACT_SYNONYM)— chebi
[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-fluoro-3,4-dihydroxytetrahydrofuran-2-yl]methyl sulfamate (EXACT_SYNONYM)— chebi
[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-fluoro-3,4-dihydroxyoxolan-2-yl]methyl sulfamate (EXACT_SYNONYM)— chebi
antibiotic T-3018 (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:24751-69-7
chemspider:65250
metacyc.compound:CPD-12712
wikipedia.en:Nucleocidin

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:25605 CHEBI:25605
CHEBI:33282 CHEBI:33282
CHEBI:36335 CHEBI:36335

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:166872`	nucleocidin	`antibioticmech:chebi-fce556dccd`	2026-08-30

Mechanism summary

Mode of action: PROTEIN_SYNTHESIS_INHIBITION host shared target — Assigned from ChEBI role CHEBI:48001 (protein synthesis inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.