sinefungin

CHEBI:45453 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

An adenosine that is the the δ-(5'-adenosyl) derivative of ornithine. — 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:22260
Label unavailable CHEBI:83925

Chemical structure

Computed structure properties
Molecular formula	C15H23N7O5
Charge	0
Average mass	381.393 Da
Monoisotopic mass	381.17607 Da
Source	ChEBI
InChIKey	LMXOHSDXUQEUSF-YECHIGJVSA-N

SMILES

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

InChI

InChI=1S/C15H23N7O5/c16-6(1-2-7(17)15(25)26)3-8-10(23)11(24)14(27-8)22-5-21-9-12(18)19-4-20-13(9)22/h4-8,10-11,14,23-24H,1-3,16-17H2,(H,25,26)(H2,18,19,20)/t6-,7-,8+,10+,11+,14+/m0/s1

Also called

sinefungina (INN)— chebi
sinefungine (INN)— chebi
sinefunginum (INN)— chebi
(5S)-5-amino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]-L-norleucine (EXACT_SYNONYM)— chebi
(2S,5S)-2,5-diamino-6-[(2R,3S,R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]hexanoic acid (EXACT_SYNONYM)— chebi
6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-beta-D-ribo-decofuranuronic acid (EXACT_SYNONYM)— chebi
6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxydecofuranuronic acid (EXACT_SYNONYM)— chebi
A 9145 (EXACT_SYNONYM)— chebi
ADENOSYL-ORNITHINE (EXACT_SYNONYM)— chebi
Antibiotic A 9145 (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.

kegg.drug:D05846

Patents and articles

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

Activity roles

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

antimicrobial agent CHEBI:33281
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:45453`	sinefungin	`antibioticmech:chebi-c266cf14d1`	2026-08-30

Resistance mechanisms

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

UNKNOWN 3

UNKNOWN
Determinant	ARO ID	Organism	Gene families	Evidence
Laboratory ABD1-associated sinefungin resistance Context-dependent association in W303 derivatives, not a species-wide phenotype. Experimental allele, protein and genome unresolved. The stronger combined-context effect is not assigned to this gene individually; a specific molecular resistance route is not asserted.	—	Saccharomyces cerevisiae `NCBITaxon:4932` ABD1	—	PMID:17932050 (Results and native Figures 7; DOI:10.1093/nar/gkm817. Comparative growth, not a standardized MIC.) https://www.uniprot.org/uniprotkb/P32783/entry (Reference-only UniProtKB:P32783, entry version 191, sequence version 1, release 2026_03; ABD1 in S288c (NCBITaxon:559292). Not the tested W303 derivative or an exact resistance allele.) Comparative growth susceptibility
Laboratory SAM1-associated sinefungin resistance Context-dependent association in W303 derivatives, not a species-wide phenotype. Experimental allele, protein and genome unresolved. The stronger combined-context effect is not assigned to this gene individually; a specific molecular resistance route is not asserted.	—	Saccharomyces cerevisiae `NCBITaxon:4932` SAM1	—	PMID:17932050 (Results and native Figures 7; DOI:10.1093/nar/gkm817. Comparative growth, not a standardized MIC.) https://www.uniprot.org/uniprotkb/P10659/entry (Reference-only UniProtKB:P10659, entry version 228, sequence version 2, release 2026_03; SAM1 in S288c (NCBITaxon:559292). Not the tested W303 derivative or an exact resistance allele.) Comparative growth susceptibility
Laboratory SAM2-associated sinefungin resistance Context-dependent association in W303 derivatives, not a species-wide phenotype. Experimental allele, protein and genome unresolved. The stronger combined-context effect is not assigned to this gene individually; a specific molecular resistance route is not asserted.	—	Saccharomyces cerevisiae `NCBITaxon:4932` SAM2	—	PMID:17932050 (Results and native Figures 7; DOI:10.1093/nar/gkm817. Comparative growth, not a standardized MIC.) https://www.uniprot.org/uniprotkb/P19358/entry (Reference-only UniProtKB:P19358, entry version 217, sequence version 3, release 2026_03; SAM2 in S288c (NCBITaxon:559292). Not the tested W303 derivative or an exact resistance allele.) Comparative growth susceptibility

ANTIBIOTIC_TARGET_ALTERATION 1

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Laboratory ABD1 target-alteration association with sinefungin resistance Distinct 2025 laboratory association, not the earlier expression-context finding or a species-wide phenotype. Reference-sequence identity does not identify experimental alleles, strains or genomes; none is assigned. K. lactis biochemical results and modeled orthologs are not organismal resistance evidence.	—	Saccharomyces cerevisiae `NCBITaxon:4932` ABD1	—	PMID:40682821 (Results and native Figures 3-4; DOI:10.1093/nar/gkaf538. Relative growth and enzyme inhibition are distinct endpoints, not standardized MICs.) https://www.uniprot.org/uniparc/UPI000005318F (Reference-only archive link, release 2026_03: historical UniProtKB:A6ZLH5 (YJM789, NCBITaxon:307796) is inactive; UniProtKB:P32783 (S288c, NCBITaxon:559292) remains active. Same archived reference sequence does not establish strain or experimental-allele equivalence.) https://www.uniprot.org/uniprotkb/P32783/entry (Current reference only: entry version 191, sequence version 1, release 2026_03. Not assigned as an experimental resistance protein accession.) Comparative yeast growth with corroborating biochemical inhibition assays

REDUCED_PERMEABILITY 1

REDUCED_PERMEABILITY
Determinant	ARO ID	Organism	Gene families	Evidence
Laboratory SAM3-associated sinefungin resistance Context-dependent association in W303 derivatives, not a species-wide phenotype. Experimental allele, protein and genome unresolved. Reduced uptake is the authors' genetic interpretation, not an efflux measurement; the opposite-direction control is retained in the dossier.	—	Saccharomyces cerevisiae `NCBITaxon:4932` SAM3	—	PMID:17932050 (Results and native Figures 3, 4 and 6; DOI:10.1093/nar/gkm817. Comparative growth, not a standardized MIC.) https://www.uniprot.org/uniprotkb/Q08986/entry (Reference-only UniProtKB:Q08986, entry version 170, sequence version 1, release 2026_03; SAM3 in S288c (NCBITaxon:559292). Not the tested W303 derivative or an exact resistance allele.) Comparative growth susceptibility

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 four qualified laboratory yeast gene associations from inspected primary results. UniProt identifiers remain reference-only; no experimental allele, protein, genome or numerical AST assigned. Preserved existing owners and left whole-record review open.
CURATED_RESISTANCE_EVIDENCE 2026-10-13 · codex · LLM-assisted
Added a distinct 2025 laboratory ABD1 target-alteration association from primary figures. Grounded historical/current reference correspondence through UniParc without transferring reference strain or protein IDs to tested alleles. Preserved four earlier claims; no genome or numerical AST assigned. Whole-record review remains open.

Provenance

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

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