arisugacin C

CHEBI:65437 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

An organic heterotetracyclic compound that is 4,4,6a,12b-tetramethyl-1,4a,5,6,6a,12,12a,12b-octahydro-2H,11H-benzo[f]pyrano[4,3-b]chromene-3,11(4H)-dione substituted at position 4a by a hydroxy and and at position 9 by 4-methoxyphenyl group (the 4aS,6aR,12aR,12bR stereoisomer). Isolated from the culture broth of Penicillium, it acts as a selective inhibitor of acetylcholinesterase. — 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:18946 CHEBI:18946
CHEBI:26878 CHEBI:26878
CHEBI:35618 CHEBI:35618
CHEBI:38163 CHEBI:38163
CHEBI:3992 CHEBI:3992

Chemical structure

Computed structure properties
Molecular formula	C27H32O6
Charge	0
Average mass	452.547 Da
Monoisotopic mass	452.21989 Da
Source	ChEBI
InChIKey	XKDGQMPLQPRTCS-HHPVDLARSA-N

SMILES

[H][C@]12Cc3c(cc(-c4ccc(OC)cc4)oc3=O)O[C@]1(C)CC[C@@]1(O)C(C)(C)C(=O)CC[C@]21C

InChI

InChI=1S/C27H32O6/c1-24(2)22(28)10-11-25(3)21-14-18-20(33-26(21,4)12-13-27(24,25)30)15-19(32-23(18)29)16-6-8-17(31-5)9-7-16/h6-9,15,21,30H,10-14H2,1-5H3/t21-,25-,26-,27-/m1/s1

Also called

(4aS,6aR,12aR,12bR)-4a-hydroxy-9-(4-methoxyphenyl)-4,4,6a,12b-tetramethyl-1,4a,5,6,6a,12,12a,12b-octahydro-2H,11H-benzo[f]pyrano[4,3-b]chromene-3,11(4H)-dione (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:8521391

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:65437`	arisugacin C	`antibioticmech:chebi-a577e78a51`	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.