acrophiarin

CHEBI:167054 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A cyclic hexapeptide echinocandin antibiotic with a myristoyl side chain. It is produced by a specific strain of Penicillium arenicola and exhibits antimycotic activity. — 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.

Label unavailable CHEBI:24613
echinocandin CHEBI:57248
antibiotic antifungal agent CHEBI:86478

Chemical structure

Computed structure properties
Molecular formula	C49H78N8O17
Charge	0
Average mass	1051.202 Da
Monoisotopic mass	1050.54849 Da
Source	ChEBI
InChIKey	QZRPBFSNQQUAAB-QZXUYJGCSA-N

SMILES

[H][C@@]12C[C@@H](O)CN1C(=O)[C@H]([C@@H](C)O)NC(=O)[C@@]([H])(NC(=O)CCCCCCCCCCCCC)C[C@@H](O)[C@@H](O)NC(=O)[C@@H]1[C@@H](O)[C@@H](C)CN1C(=O)[C@H]([C@H](O)CC(N)=O)NC(=O)[C@H]([C@H](O)[C@@H](O)c1ccc(O)cc1)NC2=O

InChI

InChI=1S/C49H78N8O17/c1-4-5-6-7-8-9-10-11-12-13-14-15-35(64)51-30-21-33(62)45(70)55-47(72)39-40(65)25(2)23-57(39)49(74)37(32(61)22-34(50)63)53-46(71)38(42(67)41(66)27-16-18-28(59)19-17-27)54-44(69)31-20-29(60)24-56(31)48(73)36(26(3)58)52-43(30)68/h16-19,25-26,29-33,36-42,45,58-62,65-67,70H,4-15,20-24H2,1-3H3,(H2,50,63)(H,51,64)(H,52,68)(H,53,71)(H,54,69)(H,55,72)/t25-,26+,29+,30-,31-,32+,33+,36-,37-,38-,39-,40-,41-,42-,45+/m0/s1

Also called

N-{(2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-20-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,12,15-tetrahydroxy-6-[(1R)-1-hydroxyethyl]-16-methyl-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl}tetradecanamide (EXACT_SYNONYM)— chebi
S31794/F-1 (EXACT_SYNONYM)— chebi
antibiotic S31794/F-1 (EXACT_SYNONYM)— chebi

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

patent:US4173629

Activity roles

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

antifungal agent CHEBI:35718

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:167054`	acrophiarin	`antibioticmech:chebi-81b94b53ab`	2026-08-30

Mechanism summary

Mode of action: CELL_WALL_SYNTHESIS_INHIBITION microbial target — Assigned from ChEBI role CHEBI:230471 (EC 2.4.1.34 (1,3-β-glucan synthase) inhibitor). ChEBI asserts the role on the compound. The role names a target specific to the microbe or virus — see mode_of_action_target_scope. Not a curator's mechanistic review.

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
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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