aculeacin A

CHEBI:2450 ·resolve ·ANTIFUNGAL ·EXACT REVIEWED

A lipopeptide that is isolated from Aspergillus aculeatus and exhibits antifungal activity. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• Label unavailable CHEBI:24533
• Label unavailable CHEBI:46895

Chemical structure

SMILES

CCCCCCCCCCCCCCCC(=O)N[C@H]1C[C@@H](O)[C@@H](O)NC(=O)[C@@H]2[C@@H](O)[C@@H](C)CN2C(=O)[C@H]([C@H](O)CC(N)=O)NC(=O)[C@H]([C@H](O)[C@@H](O)c2ccc(O)cc2)NC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@H]([C@@H](C)O)NC1=O

InChI

InChI=1S/C51H82N8O17/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-37(66)53-32-23-35(64)47(72)57-49(74)41-42(67)27(2)25-59(41)51(76)39(34(63)24-36(52)65)55-48(73)40(44(69)43(68)29-18-20-30(61)21-19-29)56-46(71)33-22-31(62)26-58(33)50(75)38(28(3)60)54-45(32)70/h18-21,27-28,31-35,38-44,47,60-64,67-69,72H,4-17,22-26H2,1-3H3,(H2,52,65)(H,53,66)(H,54,70)(H,55,73)(H,56,71)(H,57,74)/t27-,28+,31+,32-,33-,34+,35+,38-,39-,40-,41-,42-,43-,44-,47+/m0/s1

Also called

• Aculeacin A (EXACT_SYNONYM)— chebi
• Aculeacins (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.

• cas:58814-86-1
• kegg.compound:C01776
• knapsack:C00016077
• metacyc.compound:CPD-13365
• reaxys:26317172

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.

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

beta-1,3-glucan synthase reaction BIOLOGICAL_PROCESS MEASURED_TARGET_ASSOCIATION

Whole-cell and cell-free experiments in Saccharomyces cerevisiae and Candida albicans measured reduced cell-wall glucan synthesis. No direct binding to a molecularly defined glucan-synthase subunit was established. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 1977-04; 1982-02 (retrieved 2026-09-02).

• PMID:324960 (Primary whole-cell mechanism study in S. cerevisiae.)
• PMID:7042671 (Primary whole-cell and cell-free mechanism study in C. albicans and S. cerevisiae.)

Mechanism summary

Mode of action

CELL_WALL_SYNTHESIS_INHIBITION microbial target — CURATOR: PMID:324960 showed reduced incorporation of glucose into Saccharomyces cerevisiae cell-wall glucan, and PMID:7042671 showed preferential inhibition of alkali-insoluble glucan and beta-1,3-glucan synthesis from UDP-glucose in Candida albicans and S. cerevisiae extracts. These experiments support fungal cell-wall synthesis inhibition without establishing direct binding to a defined synthase subunit.

Resistance mechanisms

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

Producer organisms

Organisms that biosynthesize this compound. Cluster link evidence is how the upstream source graded the gene cluster, so it is populated only for a source that grades it. An empty cell is not weaker support: a curator-authored producer carries its support in Evidence instead. Where the source entry named several compounds, the evidence is marked inherited, meaning it covers this compound together with the cluster's other products rather than singling it out. Those products need not be related to each other: a cluster can list an intermediate, a precursor and a finished antibiotic side by side.

Record-level evidence

• PMID:324959 (Primary isolation, chemical characterization, producer, and antifungal-spectrum report.)
• PMID:324960 (Primary fungal cell-wall mode-of-action study.)
• PMID:7042671 (Primary beta-glucan-synthesis mechanism study.)

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. REVIEWED 2026-09-02 · codex · LLM-assisted

   Verified exact ChEBI identity, structure, and antifungal class; added primary-evidence fungal cell-wall/beta-glucan mechanism, the reported Aspergillus aculeatus M-4214 producer, and record evidence.

5. CURATED_RESISTANCE_EVIDENCE 2026-10-13 · codex · LLM-assisted

   Added compound-specific historical ACR locus associations from primary results. Kept the molecular route unknown, rejected unsupported modern alias/protein joins, and retained species-only taxonomy. Existing claims are unchanged; no allele, 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).

Explore across X-Mech: MediaIngredientMech (aculeacin A) · CultureMech · NaturalProductMech · PathwayMech · TraitMech · TaxonMech (Aspergillus aculeatus)