Basic Description

Synonyms	cccp \| 555-60-2 \| Carbonyl cyanide 3-chlorophenylhydrazone \| (3-Chlorophenyl)hydrazonomalononitrile \| Carbonyl cyanide m-chlorophenylhydrazone \| Carbonylcyanide-3-chlorophenylhydrazone \| Carbonyl cyanide m-chlorophenyl hydrazone \| m-Chlorophenyl carbonylcyanide hydrazo
Specifications & Purity	10mM in DMSO
Biochemical and Physiological Mechanisms	Potent mitochondrial oxidative phosphorylation uncoupler. Renders mitochondrial inner membrane permeable to protons. Induces apoptosis in vitro .
Storage Temp	Store at -80°C
Shipped In	Ice chest + Ice pads

Associated Targets(Human)

CYP3A4 Tclin Cytochrome P450 3A4 (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

RORC Tchem Nuclear receptor ROR-gamma (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

FTL Tbio Ferritin light chain (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

HSD17B10 Tchem 3-hydroxyacyl-CoA dehydrogenase type-2 (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

KMT2A Tchem Histone-lysine N-methyltransferase 2A (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SMN1 Tchem Survival motor neuron protein (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TSHR Tclin Thyrotropin receptor (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PINK1 Tbio Serine/threonine-protein kinase PINK1, mitochondrial (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ALOX15B Tchem Arachidonate 15-lipoxygenase B (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ALOX15 Tchem Arachidonate 15-lipoxygenase (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MAPT Tclin Microtubule-associated protein tau (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CISD1 Tchem CDGSH iron-sulfur domain-containing protein 1 (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

IMPA1 Tclin Inositol monophosphatase 1 (0 Activities)

Discover Target: IMPA1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

Discover Target: TSHR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX15B Tchem Arachidonate 15-lipoxygenase, type II (7244 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

A2780cisR (133 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CCRF-CEM (65223 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HL-60 (67320 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HT-29 (80576 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

J82 (505 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MCF7 (126967 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NB-4 (999 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PC-3 (62116 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RT-112 (346 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SGC-7901 (2773 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

U-87 MG (3946 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

A549 (127892 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FaDu (1726 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HCT-116 (91556 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HEK293 (82097 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HepG2 (196354 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NCI-H460 (60772 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

A2780 (11979 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HeLa (62764 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MDA-MB-231 (73002 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HSD17B10 Tchem Endoplasmic reticulum-associated amyloid beta-peptide-binding protein (20669 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Liver (3974 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SMN1 Tchem Survival motor neuron protein (34246 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CISD1 Tchem CDGSH iron-sulfur domain-containing protein 1 (222 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PINK1 Tbio Serine/threonine-protein kinase PINK1, mitochondrial (21 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HEK-293T (167025 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HepG2-CD81 (19978 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

blaZ Beta-lactamase (285 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Papain (844 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cruzipain (33337 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Pseudomonas aeruginosa (123386 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Klebsiella pneumoniae (43867 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Bacteroides fragilis (1445 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Bacteroides thetaiotaomicron (562 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Staphylococcus aureus (210822 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Staphylococcus epidermidis (22802 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Klebsiella aerogenes (4963 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Escherichia coli (133304 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Streptococcus mutans (2687 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Bacillus subtilis (32866 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Clostridioides difficile (2968 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Clostridium perfringens (1165 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mycobacterium tuberculosis (203094 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Saccharomyces cerevisiae (19171 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Enterococcus faecalis (29875 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Bacillus cereus (7522 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Lacticaseibacillus casei (578 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mycobacterium tuberculosis variant bovis (1746 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mycolicibacterium smegmatis (8003 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trypanosoma brucei brucei (13300 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Plasmodium falciparum (966862 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Leishmania donovani (89745 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trypanosoma cruzi (99888 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Plasmodium berghei (192651 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Caenorhabditis elegans (1055 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Onchocerca volvulus (56 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

C2C12 (756 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

lef Anthrax lethal factor (7585 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

norA Quinolone resistance protein norA (2171 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

pef Plasmid efflux fluoroquinolone (1 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Bifidobacterium longum (298 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mycobacterium tuberculosis variant bovis BCG (1626 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mapt Microtubule-associated protein tau (6 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rorc Nuclear receptor ROR-gamma (89407 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Impa1 Inositol monophosphatase 1 (16203 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FTL Ferritin light chain (43324 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

qacEdelta1 QacEdelta1 SMR family efflux pump (1 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

mdtK Multidrug resistance protein mdtK (13 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cell membrane (1233 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Acinetobacter pittii (585 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

lfrA Multidrug efflux pump LfrA (106 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Limosilactobacillus reuteri (118 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Names and Identifiers

IUPAC Name	2-[(3-chlorophenyl)hydrazinylidene]propanedinitrile
INCHI	InChI=1S/C9H5ClN4/c10-7-2-1-3-8(4-7)13-14-9(5-11)6-12/h1-4,13H
InChi Key	UGTJLJZQQFGTJD-UHFFFAOYSA-N
Canonical SMILES	C1=CC(=CC(=C1)Cl)NN=C(C#N)C#N
Isomeric SMILES	C1=CC(=CC(=C1)Cl)NN=C(C#N)C#N
PubChem CID	2603
Molecular Weight	204.62

Certificates

Certificate of Analysis(COA)

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Chemical and Physical Properties

Sensitivity	Air Sensitive

Safety and Hazards(GHS)

Pictogram(s)	GHS06, GHS07
Signal	Danger
Hazard Statements	H315:Causes skin irritation H319:Causes serious eye irritation H335:May cause respiratory irritation H301:Toxic if swallowed H311:Toxic in contact with skin H331:Toxic if inhaled
Precautionary Statements	P261:Avoid breathing dust/fume/gas/mist/vapors/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do - continue rinsing. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of water. P321:Specific treatment (see ... on this label). P405:Store locked up. P501:Dispose of contents/container to ... P264:Wash hands [and …] thoroughly after handling. P271:Use only outdoors or in a well-ventilated area. P270:Do not eat, drink or smoke when using this product. P304+P340:IF INHALED: Remove person to fresh air and keep comfortable for breathing. P403+P233:Store in a well-ventilated place. Keep container tightly closed. P362+P364:Take off contaminated clothing and wash it before reuse. P330:Rinse mouth. P361+P364:Take off immediately all contaminated clothing and wash it before reuse. P264+P265:Wash hands [and …] thoroughly after handling. Do not touch eyes. P301+P316:IF SWALLOWED: Get emergency medical help immediately. P337+P317:If eye irritation persists: Get medical help. P332+P317:If skin irritation occurs: Get medical help. P316:Get emergency medical help immediately. P319:Get medical help if you feel unwell.

Citations of This Product

1. Xijuan Chao, Dezhi Yao, Chuxuan Chen, Zhiguo Sheng, Benzhan Zhu. (2024) Tetrabromobisphenol A induces neuronal cytotoxicity by inhibiting PINK1-Parkin-mediated mitophagy via upregulating ATF3 expression. SCIENCE OF THE TOTAL ENVIRONMENT, 912 (169175). [PMID:38065503]
2. Wei Liu, Tengfei Wang, Liwen Wang, Yan Wang, Sheng Hu, Dating Tian. (2024) A novel near-infrared fluorescent probe for ultrasensitive and visual detection of mitochondrial viscosity. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 304 (123329). [PMID:37683438]
3. Zhang Hongzhen, Zhang Chenghua, Xiang Xiaolong, Zhang Qilun, Zhao Wei, Wei Guoyu, Hu Anlong. (2022) Uptake and transport of antibiotic kasugamycin in castor bean (Ricinus communis L.) seedlings. Frontiers in Microbiology, 13 [PMID:36033898]

References

1. Xijuan Chao, Dezhi Yao, Chuxuan Chen, Zhiguo Sheng, Benzhan Zhu. (2024) Tetrabromobisphenol A induces neuronal cytotoxicity by inhibiting PINK1-Parkin-mediated mitophagy via upregulating ATF3 expression. SCIENCE OF THE TOTAL ENVIRONMENT, 912 (169175). [PMID:38065503]
2. Wei Liu, Tengfei Wang, Liwen Wang, Yan Wang, Sheng Hu, Dating Tian. (2024) A novel near-infrared fluorescent probe for ultrasensitive and visual detection of mitochondrial viscosity. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 304 (123329). [PMID:37683438]
3. Zhang Hongzhen, Zhang Chenghua, Xiang Xiaolong, Zhang Qilun, Zhao Wei, Wei Guoyu, Hu Anlong. (2022) Uptake and transport of antibiotic kasugamycin in castor bean (Ricinus communis L.) seedlings. Frontiers in Microbiology, 13 [PMID:36033898]

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Carbonyl cyanide 3-chlorophenylhydrazone - 10mM in DMSO, high purity , CAS No.555-60-2