TMC-86A

CHEBI:66242 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

An epoxide that is oxiran-2-ylmethanol which is acylated at position 2 by N-butanoyl-L-seryl-4-methylidenenorvalinyl group. It is a proteasome inhibitor isolated from Streptomyces. — 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.

CHEBI:15734 CHEBI:15734
CHEBI:17087 CHEBI:17087
CHEBI:23824 CHEBI:23824
CHEBI:29347 CHEBI:29347
CHEBI:32955 CHEBI:32955
CHEBI:35681 CHEBI:35681

Chemical structure

Computed structure properties
Molecular formula	C16H26N2O6
Charge	0
Average mass	342.392 Da
Monoisotopic mass	342.17909 Da
Source	ChEBI
InChIKey	JVPIPRZCKOLWKU-BGMSHATGSA-N

SMILES

C=C(C)CC(NC(=O)[C@H](CO)NC(=O)CCC)C(=O)C1(CO)CO1

InChI

InChI=1S/C16H26N2O6/c1-4-5-13(21)17-12(7-19)15(23)18-11(6-10(2)3)14(22)16(8-20)9-24-16/h11-12,19-20H,2,4-9H2,1,3H3,(H,17,21)(H,18,23)/t11?,12-,16?/m0/s1

Also called

N-[(2S)-3-hydroxy-1-[[1-[2-(hydroxymethyl)oxiran-2-yl]-4-methyl-1-oxopentan-2-yl]amino]-1-oxobutan-2-yl]-3-methylbutanamide (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:8510499

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:66242`	TMC-86A	`antibioticmech:chebi-990c280655`	2026-08-30

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

Provenance

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