AntibioticMech

cathestatin A

CHEBI:65599 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

A dicarboxylic acid monoamide obtained by the formal condensation of the carboxylic group of oxirane-2,3-dicarboxylic acid with the amino group of N-(4-aminobutyl)-L-phenylalaninamide (the 2S,3S stereoisomer). An antibiotic isolated from the fermentation broth of Penicillium citrinum, it acts as a potent inhibitor of cysteine protease. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:25384 CHEBI:25384
• CHEBI:32955 CHEBI:32955
• CHEBI:35735 CHEBI:35735
• CHEBI:50994 CHEBI:50994

Chemical structure

Computed structure properties

Molecular formula	C17H23N3O5
Charge	0
Average mass	349.387 Da
Monoisotopic mass	349.16377 Da
Source	ChEBI
InChIKey	ZERGYHMBBZCBJM-IHRRRGAJSA-N

SMILES

NCCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H]1O[C@@H]1C(=O)O

InChI

InChI=1S/C17H23N3O5/c18-8-4-5-9-19-15(21)12(10-11-6-2-1-3-7-11)20-16(22)13-14(25-13)17(23)24/h1-3,6-7,12-14H,4-5,8-10,18H2,(H,19,21)(H,20,22)(H,23,24)/t12-,13-,14-/m0/s1

Also called

• (2S,3S)-3-({(2S)-1-[(4-aminobutyl)amino]-1-oxo-3-phenylpropan-2-yl}carbamoyl)oxirane-2-carboxylic acid (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• chemspider:8103948
• reaxys:7229726

Activity roles

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

• CHEBI:33281 CHEBI:33281

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:65599	cathestatin A	antibioticmech:chebi-5556ece49e	2026-08-30

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

Provenance

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