isoprothiolane

CHEBI:6047 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A malonate ester that is diisopropyl malonate in which the two methylene hydrogens at position 2 are replaced by a 1,3-dithiolan-2-ylidene group. An insecticide and fungicide used to control a range of diseases including Pyricularia oryzae, Helminthosporium sigmoideum and Fusarium nivale. — 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:35725 CHEBI:35725
CHEBI:38083 CHEBI:38083
CHEBI:39192 CHEBI:39192

Chemical structure

Computed structure properties
Molecular formula	C12H18O4S2
Charge	0
Average mass	290.406 Da
Monoisotopic mass	290.06465 Da
Source	ChEBI
InChIKey	UFHLMYOGRXOCSL-UHFFFAOYSA-N

SMILES

CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1

InChI

InChI=1S/C12H18O4S2/c1-7(2)15-10(13)9(11(14)16-8(3)4)12-17-5-6-18-12/h7-8H,5-6H2,1-4H3

Also called

di(propan-2-yl) 1,3-dithiolan-2-ylidenemalonate (EXACT_SYNONYM)— chebi
Isoprothiolane (EXACT_SYNONYM)— chebi
bis(1-methylethyl) 1,3-dithiolan-2-ylidenepropanedioate (EXACT_SYNONYM)— chebi
di-isopropyl 1,3-dithiolane-2-ylidenemalonate (EXACT_SYNONYM)— chebi
diisopropyl 1,3-dithiolan-2-ylidenemalonate (EXACT_SYNONYM)— chebi
diisopropyl 2-(1,3-dithiolan-2-ylidene)malonate (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:50512-35-1
hmdb:HMDB0031779
kegg.compound:C11111
pesticides:isoprothiolane
ppdb:408
reaxys:2128528

Activity roles

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

CHEBI:86328 CHEBI:86328

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:6047`	isoprothiolane	`antibioticmech:chebi-f16b1280b1`	2026-08-30

Mechanism summary

Mode of action: CELL_MEMBRANE_SYNTHESIS_INHIBITION host shared target — Assigned from ChEBI role CHEBI:83741 (phospholipid biosynthesis inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — 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

Provenance

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