AntibioticMech

TMC-52C

CHEBI:66240 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

An epoxide which is a carboxamide obtained by the formal condensation of one of the carboxy groups of oxirane-2,3-dicarboxylic acid with N-{3-[(4-aminobutyl)amino]propyl}-L-phenylalaninamide. It is a natural product, isolated from Gliocladium sp. F-2665. TMC-52C acts as an inhibitor of cysteine proteinases, particularly cathepsin B (EC 3.4.22.1), cathepsin L (EC 3.4.22.15), and papain (EC 3.4.22.2), with IC50 values of 460 nM, 10 nM, and 88 nM, respectively. The epoxide group has trans configuration but its exact stereochemistry is uncertain: it is either (2R,3R) or (2S,3S). — 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
• CHEBI:50995 CHEBI:50995

Chemical structure

Computed structure properties

Molecular formula	C20H30N4O5
Charge	0
Average mass	406.483 Da
Monoisotopic mass	406.22162 Da
Source	ChEBI
InChIKey	LYAOVDVXUUARTK-GTPINHCMSA-N

SMILES

NCCCCNCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)C1OC1C(=O)O

InChI

InChI=1S/C20H30N4O5/c21-9-4-5-10-22-11-6-12-23-18(25)15(13-14-7-2-1-3-8-14)24-19(26)16-17(29-16)20(27)28/h1-3,7-8,15-17,22H,4-6,9-13,21H2,(H,23,25)(H,24,26)(H,27,28)/t15-,16?,17?/m0/s1

Also called

• (2R*,3R*)-3-{[(2S)-1-({3-[(4-aminobutyl)amino]propyl}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.

• reaxys:8169550

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:66240	TMC-52C	antibioticmech:chebi-9e61579646	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.