vamidothion

CHEBI:38990 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

An organic thiophosphate that is N-methyl-2-[(2-sulfanylethyl)sulfanyl]propanamide in which the thiol group has been converted into the corresponding O,O-dimethyl thiophoshate. Formerly used as an insecticide and acaricide, it is no longer approved for use within the European Union. — 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:25715 CHEBI:25715
CHEBI:37512 CHEBI:37512

Chemical structure

Computed structure properties
Molecular formula	C8H18NO4PS2
Charge	0
Average mass	287.343 Da
Monoisotopic mass	287.04149 Da
Source	ChEBI
InChIKey	LESVOLZBIFDZGS-UHFFFAOYSA-N

SMILES

CNC(=O)C(C)SCCSP(=O)(OC)OC

InChI

InChI=1S/C8H18NO4PS2/c1-7(8(10)9-2)15-5-6-16-14(11,12-3)13-4/h7H,5-6H2,1-4H3,(H,9,10)

Also called

O,O-dimethyl S-(2-{[1-methyl-2-(methylamino)-2-oxoethyl]sulfanyl}ethyl) phosphorothioate (EXACT_SYNONYM)— chebi
Dimethyl S-(2-(1-methylcarbamoylethylthio)ethyl) phosphorothiolate (EXACT_SYNONYM)— chebi
O,O-Dimethyl S-(2-(1-methylcarbamoylethylthio)ethyl) phosphorothioate (EXACT_SYNONYM)— chebi
O,O-dimethyl S-(2-{[1-methyl-2-(methylamino)-2-oxoethyl]sulfanyl}ethyl) thiophosphate (EXACT_SYNONYM)— chebi
Vamidoate (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:2275-23-2
kegg.compound:C18666
pesticides:vamidothion
ppdb:678
reaxys:2651123

Activity roles

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

CHEBI:33282 CHEBI:33282
CHEBI:35718 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:38990`	vamidothion	`antibioticmech:chebi-8772976f7c`	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.