Products for Research Use Only
RegisterLogin

CCCP

CAT: 0804-HY-100941-02Size: 50 mgDry Ice: NoHazardous: No
Product image 1
1 / 1
CAT#:0804-HY-100941-02Size:50 mg
Selected
24/48H Stock Items & 2 to 6 Weeks non Stock Items.
Quick Request Actions
Description
CCCP is an oxidative phosphorylation (OXPHOS) uncoupler. CCCP induces activation of PINK1 leading to Parkin Ser65 phosphorylation[1].
CAS Number
555-60-2
Product Name Alternative
Carbonyl cyanide 3-chlorophenylhydrazone; Carbonyl Cyanide m-Chlorophenylhydrazone
UNSPSC
12352005
Hazard Statement
H301+H311+H331
Target
Apoptosis; Bacterial; IFNAR; Mitochondrial Metabolism; Oxidative Phosphorylation; PINK1/Parkin; STING
Type
Reference compound
Related Pathways
Anti-infection; Apoptosis; Autophagy; Immunology/Inflammation; Metabolic Enzyme/Protease; Neuronal Signaling
Applications
Cancer-Kinase/protease
Field of Research
Cancer; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/CCCP.html
Purity
99.83
Solubility
DMSO : 50 mg/mL (ultrasonic) |H2O : < 0.1 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
N#C/C(C#N)=N/NC1=CC=CC(Cl)=C1
Molecular Formula
C9H5ClN4
Molecular Weight
204.62
Precautions
H301+H311+H331
References & Citations
[1]Kwon D, et al. Carbonyl cyanide 3-chlorophenylhydrazone (CCCP) suppresses STING-mediated DNA sensing pathway through inducing mitochondrial fission. Biochem Biophys Res Commun. 2017 Aug 30. pii: S0006-291X (17) 31704-7.|[2]Sinha D, et al. Synergistic efficacy of Bisbenzimidazole and Carbonyl Cyanide 3-Chlorophenylhydrazonecombination against MDR bacterial strains. Sci Rep. 2017 Mar 17;7:44419.|[3]Kawamoto A, et al. Measurement of technetium-99m sestamibi signals in rats administered a mitochondrial uncoupler and in a rat model of heart failure. PLoS One. 2015 Jan 16;10 (1) :e0117091.|[4]Kondapalli C, et al. PINK1 is activated by mitochondrial membrane potential depolarization and stimulates Parkin E3 ligase activity by phosphorylating Serine 65. Open Biol. 2012 May;2 (5) :120080.|[5]Haifeng Jiao, et al. Mitocytosis, a migrasome-mediated mitochondrial quality-control process. Cell. 2021 May 27;184 (11) :2896-2910.e13.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

Carbonyl cyanide (m-chlorophenyl)hydrazone

CCCP is 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. It has a role as a geroprotector, an ionophore and an antibacterial agent. It is a nitrile, a hydrazone and a member of monochlorobenzenes. It is functionally related to a hydrazonomalononitrile.

CAS Number555-60-2
PubChem CID2603
IUPAC Name2-[(3-chlorophenyl)hydrazinylidene]propanedinitrile
Molecular FormulaC9H5ClN4
Molecular Weight204.61
XLogP3.4
Topological Polar Surface Area72
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Heavy Atom Count14
Formal Charge0
Complexity300
SMILES
C1=CC(=CC(=C1)Cl)NN=C(C#N)C#N
InChI
InChI=1S/C9H5ClN4/c10-7-2-1-3-8(4-7)13-14-9(5-11)6-12/h1-4,13H
InChIKey
UGTJLJZQQFGTJD-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Carbonyl cyanide (m-chlorophenyl)hydrazone
CAS: 555-60-2
CID: 2603
Formula: C9H5ClN4
MW: 204.61
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight204.61
XLogP33.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass204.0202739
Monoisotopic Mass204.0202739
Topological Polar Surface Area72 Ų
Heavy Atom Count14
Formal Charge0
Complexity300
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Related Products

CatalogName
HY-120284-01CCCI-01
HY-149158-01CCC-0975

Alternative Products

CatalogName
254895CCCP
A20342-500CCCP 500mg
A20342-200CCCP 200mg
A20342-100CCCP 100mg
A20342-50CCCP 50mg
A20342-10CCCP 10mg
A20342-10mM-DCCCP 10mM * 1mL in DMSO
BAL431CCCP Cell Apoptosis Inducer, 1 pack = 50 µL
MBS8579575-01JC-1 Mitochondrial Membrane Potential Kit (JC-1/CCCP)

Popular Products