promysalin

CHEBI:171658 ·resolve ·ANTIBACTERIAL ·EXACT REVIEWED

A carboxylic ester resulting from the formal condensation of the carboxy group of (2S)-1-(2-hydroxybenzoyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid with the hydroxy group of (2R,8R)-2,8-dihydroxytetradecanamide. It is a metabolite isolated from Pseudomonas putida, , which resides in the rhizosphere of rice plants. The compound selectively inhibits the growth of Pseudomonas aeruginosa at low-micromolar concentrations. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• Label unavailable CHEBI:140324
• Label unavailable CHEBI:140326
• Label unavailable CHEBI:22702
• Label unavailable CHEBI:23763
• Label unavailable CHEBI:33308
• Label unavailable CHEBI:33853
• Label unavailable CHEBI:35681

Chemical structure

SMILES

CCCCCC[C@H](CCCCC[C@@H](O)C(N)=O)OC(=O)[C@@H]1CC=CN1C(=O)c1ccccc1O

InChI

InChI=1S/C26H38N2O6/c1-2-3-4-6-12-19(13-7-5-8-17-23(30)24(27)31)34-26(33)21-15-11-18-28(21)25(32)20-14-9-10-16-22(20)29/h9-11,14,16,18-19,21,23,29-30H,2-8,12-13,15,17H2,1H3,(H2,27,31)/t19-,21+,23-/m1/s1

Also called

• (7R,13R)-14-amino-13-hydroxy-14-oxotetradecan-7-yl (2S)-1-(2-hydroxybenzoyl)-2,3-dihydro-1H-pyrrole-2-carboxylate (EXACT_SYNONYM)— chebi
• (−)-promysalin (EXACT_SYNONYM)— chebi

Activity roles

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

• antibacterial agent CHEBI:33282

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.

succinate dehydrogenase PROTEIN MEASURED_TARGET_ASSOCIATION

Affinity-based protein profiling followed by computational, biochemical, cellular, and resistant-mutant validation implicated Sdh; a compound-bound structure was not reported. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2018-01 (retrieved 2026-09-02).

Pseudomonas aeruginosa NCBITaxon:287

• PMID:29300464 (Primary P. aeruginosa target-identification and multi-method validation study (DOI:10.1021/jacs.7b11212).)

Gram-positive bacterial cell membrane MEMBRANE ATTACKED_COMPONENT

Leakage and membrane-damage assays supported membrane disruption in Gram-positive bacteria; the study did not generalize this mechanism to Gram-negative bacteria. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2017-08 (retrieved 2026-09-02).

• PMID:28821717 (Primary promysalin membrane-damage study with explicit Gram-positive scope (DOI:10.1038/s41598-017-07567-0).)

Mechanism summary

Mode of action

MULTIPLE microbial target — CURATOR: promysalin has context-dependent antibacterial mechanisms. PMID:29300464 identified Pseudomonas aeruginosa succinate dehydrogenase through affinity profiling and in-silico, in-vitro, in-vivo, and resistant-mutant validation. PMID:28821717 found membrane damage and leakage in Gram-positive bacteria but explicitly left the Gram-negative membrane mechanism unresolved.

Record-level evidence

• PMID:29300464 (Primary P. aeruginosa succinate-dehydrogenase target study.)
• PMID:28821717 (Primary Gram-positive membrane-disruption 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, role, and antibacterial class; added distinct P. aeruginosa succinate-dehydrogenase and Gram-positive membrane mechanisms, with the reported organism-context boundary preserved.

Provenance

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

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