TMC-89A

CHEBI:66281 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

An epoxide that is oxiran-2-ylmethanol which is acylated at position 2 by an N-[(2R)-3-amino-2-methyl-3-oxopropanoyl]-L-threonyl-L-threonylleucinyl group. It is a proteasome inhibitor isolated from Streptomyces sp. TC 1087. — 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:32955 CHEBI:32955
CHEBI:35681 CHEBI:35681
CHEBI:35779 CHEBI:35779

Chemical structure

Computed structure properties
Molecular formula	C21H36N4O9
Charge	0
Average mass	488.538 Da
Monoisotopic mass	488.24823 Da
Source	ChEBI
InChIKey	SCVCWUHUBWSKHS-CRHDNEEASA-N

SMILES

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

InChI

InChI=1S/C21H36N4O9/c1-9(2)6-13(16(29)21(7-26)8-34-21)23-19(32)14(11(4)27)25-20(33)15(12(5)28)24-18(31)10(3)17(22)30/h9-15,26-28H,6-8H2,1-5H3,(H2,22,30)(H,23,32)(H,24,31)(H,25,33)/t10-,11-,12-,13?,14+,15+,21?/m1/s1

Also called

N-[(2R)-3-amino-2-methyl-3-oxopropanoyl]-L-threonyl-N-{1-[2-(hydroxymethyl)oxiran-2-yl]-4-methyl-1-oxopentan-2-yl}-L-threoninamide (EXACT_SYNONYM)— chebi

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:66281`	TMC-89A	`antibioticmech:chebi-191b44b726`	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.