CCCP

CHEBI:3259 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A member of the class of monochlorobenzenes that is benzene substituted by 2-(1,3-dinitrilopropan-2-ylidene)hydrazinyl and chloro groups at positions 1 and 3, respectively. It is a mitochondrial depolarizing agent that induces reactive oxygen species mediated cell death. — 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:18379 CHEBI:18379
CHEBI:38532 CHEBI:38532
CHEBI:83403 CHEBI:83403

Chemical structure

Computed structure properties
Molecular formula	C9H5ClN4
Charge	0
Average mass	204.62 Da
Monoisotopic mass	204.02027 Da
Source	ChEBI
InChIKey	UGTJLJZQQFGTJD-UHFFFAOYSA-N

SMILES

N#CC(C#N)=NNc1cccc(Cl)c1

InChI

InChI=1S/C9H5ClN4/c10-7-2-1-3-8(4-7)13-14-9(5-11)6-12/h1-4,13H

Also called

N'-(3-chlorophenyl)carbonohydrazonoyl dicyanide (EXACT_SYNONYM)— chebi
(3-chlorophenyl)hydrazonomalononitrile (EXACT_SYNONYM)— chebi
Carbonyl cyanide m-chlorophenyl hydrazone (EXACT_SYNONYM)— chebi
[(3-chlorophenyl)hydrazono]malononitrile (EXACT_SYNONYM)— chebi
[(3-chlorophenyl)hydrazono]propanedinitrile (EXACT_SYNONYM)— chebi
carbonylcyanide-3-chlorophenylhydrazone (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

beilstein:1842102
cas:555-60-2
chemspider:2504
kegg.compound:C11164
lincs.smallmolecule:LSM-2341
wikipedia.en:Carbonyl_cyanide_m-chlorophenyl_hydrazone

Activity roles

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

CHEBI:33282 CHEBI:33282

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:3259`	CCCP	`antibioticmech:chebi-113ef9695e`	2026-08-30

Mechanism summary

Mode of action: MEMBRANE_DISRUPTION host shared target — Assigned from ChEBI role CHEBI:24869 (ionophore). 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.