tubercidin

CHEBI:48267 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

An N-glycosylpyrrolopyrimidine that is adenosine in which the in the 5-membered ring that is not attached to the ribose moiety is replaced by a carbon. Tubercidin is produced in the culture broth of Streptomyces tubericidus. — 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.

Label unavailable CHEBI:18254
Label unavailable CHEBI:48036
antibiotic antifungal agent CHEBI:86478

Chemical structure

Computed structure properties
Molecular formula	C11H14N4O4
Charge	0
Average mass	266.257 Da
Monoisotopic mass	266.1015 Da
Source	ChEBI
InChIKey	HDZZVAMISRMYHH-KCGFPETGSA-N

SMILES

Nc1ncnc2c1ccn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

InChI

InChI=1S/C11H14N4O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2,(H2,12,13,14)/t6-,7-,8-,11-/m1/s1

Also called

7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (EXACT_SYNONYM)— chebi
7-Deazaadenosine (EXACT_SYNONYM)— chebi
Sparsomycin A (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

drugbank:DB03172

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

patent:US4316957

Activity roles

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

antifungal agent CHEBI:35718

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:48267`	tubercidin	`antibioticmech:chebi-2bded3e66e`	2026-08-30

Resistance mechanisms

2 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

UNKNOWN 2

UNKNOWN
Determinant	ARO ID	Organism	Gene families	Evidence
Laboratory NUPM1-associated tubercidin resistance Qualified association in Friedlin laboratory derivatives, not a species-wide or clinical phenotype. Molecular route unresolved; reference proteins are not experimental allele or genome assignments.	—	Leishmania major `NCBITaxon:5664` LmjF.31.1940	—	PMID:27606425 (DOI:10.1371/journal.pntd.0004972; Results and native S1 Figure and rendered S1 Table. Qualitative association only; no numerical AST imported.) https://www.uniprot.org/uniprotkb/Q4Q668/entry (Reference-only UniProtKB:Q4Q668, unreviewed entry 71, sequence version 1, release 2026_03; exact source-reported RefSeq cross-reference. Species context only, not an exact tested derivative.) Comparative growth inhibition (IC50-based)
Laboratory TRP-associated tubercidin resistance Qualified association in Friedlin laboratory derivatives, not a species-wide or clinical phenotype. Molecular route unresolved; reference proteins are not experimental allele or genome assignments.	—	Leishmania major `NCBITaxon:5664` LmjF.31.2010	—	PMID:27606425 (DOI:10.1371/journal.pntd.0004972; Results and native Table 1 and Figures 2-3. Qualitative association only; no numerical AST imported.) https://www.uniprot.org/uniprotkb/Q4Q661/entry (Reference-only UniProtKB:Q4Q661, unreviewed entry 78, sequence version 1, release 2026_03; exact source-reported RefSeq cross-reference. Species context only, not an exact tested derivative.) Comparative growth inhibition (IC50-based)

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
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
CURATED_RESISTANCE_EVIDENCE 2026-10-13 · codex · LLM-assisted
Added two qualified laboratory gene associations from primary results and native table/figure review. Molecular routes remain UNKNOWN; UniProt proteins remain reference-only. No experimental allele, sample, genome or numeric AST assigned; existing owners preserved and whole-record review left open.

Provenance

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

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