AntibioticMech

TMC-95A

CHEBI:40322 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

A 17-membered macrocyclic lactam that incorporates a phenol and a substituted indole moiety. It includes a R-hydroxy group at position 11 and a (3-methyl-2-oxopentanoyl)amino group at position at position 18 with a S-methyl group. It acts as a proteasome inhibitor and is obtained from Apiospora montagnei Sacc. TC 1093, isolated from a soil sample. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:24828 CHEBI:24828
• CHEBI:24995 CHEBI:24995
• CHEBI:26878 CHEBI:26878
• CHEBI:33853 CHEBI:33853
• CHEBI:35681 CHEBI:35681
• CHEBI:51026 CHEBI:51026

Chemical structure

Computed structure properties

Molecular formula	C33H38N6O10
Charge	0
Average mass	678.699 Da
Monoisotopic mass	678.26494 Da
Source	ChEBI
InChIKey	ZIAXNZCTODBCKW-BOYGTWLISA-N

SMILES

C/C=C\NC(=O)[C@H]1NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)C(=O)[C@@H](C)CC)Cc2ccc(O)c(c2)-c2cccc3c2NC(=O)[C@@]3(O)[C@@H]1O

InChI

InChI=1S/C33H38N6O10/c1-4-11-35-30(46)25-27(43)33(49)19-8-6-7-17(24(19)39-32(33)48)18-12-16(9-10-22(18)40)13-20(37-31(47)26(42)15(3)5-2)28(44)36-21(14-23(34)41)29(45)38-25/h4,6-12,15,20-21,25,27,40,43,49H,5,13-14H2,1-3H3,(H2,34,41)(H,35,46)(H,36,44)(H,37,47)(H,38,45)(H,39,48)/b11-4-/t15-,20-,21-,25-,27+,33-/m0/s1

Also called

• (10S,11R,12S,15S,18S)-15-(2-amino-2-oxoethyl)-10,11,23-trihydroxy-18-{[(3S)-3-methyl-2-oxopentanoyl]amino}-9,14,17-trioxo-N-[(1Z)-prop-1-en-1-yl]-8,13,16-triazatetracyclo[18.3.1.02,7.06,10]tetracosa-1(24),2,4,6,20,22-hexaene-12-carboxamide (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• reaxys:9110474

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:40322	TMC-95A	antibioticmech:chebi-60da8f9da7	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.