Z-VAD(OMe)-FMK - Moligand™,≥98% , CAS No.187389-52-2

CAS: 187389-52-2 Cat. No.: V275259 Molecular Weight: 467.49 PubChem CID: 5497174

GRADE & PURITY Moligand™, ≥98%

Synonyms

(5-aminobenzo[a]phenoxazin-9-ylidene)-diethylazanium;chloride | Bio2_000951 | NCGC00163487-02 | 2-(N(omega)-L-arginine)succinic acid | benzyloxycarbonyl-Val-Ala-Asp(OMe) fluoromethyl ketone | benzyloxycarbonyl-Val-Ala-Asp(O-Me) fluoromethyl ketone | Benzy

Storage

Store at -20°C,Argon charged,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Product Application：
Z-VAD-FMK has been used: to induce mixed-lineage kinase domain-like (MLKL) phosphorylation (p-MLKL) in L929 cells to induce autophagy in Jurkat and K562 cells to revert killing effects of oxaliplatin or oxaliplatin combination with chloroquine (CQ) on HCT116 and SW620 cell lines as a caspase inhibitor to inhibit apoptosis and assess nuclear factor-kB, heat shock protein 70 (Hsp 70), proto-oncogene (cmyc) and tumor suppressor protein p53

Specifications

Synonyms

(5-aminobenzo[a]phenoxazin-9-ylidene)-diethylazanium;chloride | Bio2_000951 | NCGC00163487-02 | 2-(N(omega)-L-arginine)succinic acid | benzyloxycarbonyl-Val-Ala-Asp(OMe) fluoromethyl ketone | benzyloxycarbonyl-Val-Ala-Asp(O-Me) fluoromethyl ketone | Benzy

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

A cell-permeable, irreversible, pan-caspase inhibitor. Inhibits caspase processing and apoptosis induction in tumor cells in vitro . Once in the cell, endogenous esterase activity hydrolyzes the methyl groups to form the biologically active form.Non-selec

Storage

Store at -20°C, Argon charged, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one week. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504763901
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763901
• Canonical Smiles: CC(C)C(C(=O)NC(C)C(=O)NC(CC(=O)OC)C(=O)CF)NC(=O)OCC1=CC=CC=C1
• IUPAC Name: methyl (3S)-5-fluoro-3-[[(2S)-2-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]propanoyl]amino]-4-oxopentanoate
• InChIKey: MIFGOLAMNLSLGH-QOKNQOGYSA-N
• INCHI: 1S/C22H30FN3O7/c1-13(2)19(26-22(31)33-12-15-8-6-5-7-9-15)21(30)24-14(3)20(29)25-16(17(27)11-23)10-18(28)32-4/h5-9,13-14,16,19H,10-12H2,1-4H3,(H,24,30)(H,25,29)(H,26,31)/t14-,16-,19-/m0/s1
• Isomeric SMILES: C[C@@H](C(=O)N[C@@H](CC(=O)OC)C(=O)CF)NC(=O)[C@H](C(C)C)NC(=O)OCC1=CC=CC=C1
• PubChem CID: 5497174
• Molecular Weight: 467.49

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Peptidomimetics
      • Subclass Hybrid peptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Peptidomimetics
• Subclass: Hybrid peptides
• Intermediate Tree Nodes: Not available
• Direct Parent: Hybrid peptides
• Alternative Parents: Dipeptides Valine and derivatives N-acyl-alpha amino acids and derivatives Alpha amino acid amides Alanine and derivatives Beta amino acids and derivatives Benzyloxycarbonyls Gamma-keto acids and derivatives Fatty acid methyl esters N-acyl amines Alpha-haloketones Carbamate esters Methyl esters Organic carbonic acids and derivatives Secondary carboxylic acid amides Monocarboxylic acids and derivatives Organic oxides Alkyl fluorides Organofluorides Organonitrogen compounds Hydrocarbon derivatives Organopnictogen compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Hybrid peptide - Alpha-dipeptide - Valine or derivatives - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - Beta amino acid or derivatives - Alanine or derivatives - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Benzyloxycarbonyl - Gamma-keto acid - Fatty acid ester - Fatty acid methyl ester - Monocyclic benzene moiety - Fatty amide - Fatty acyl - Benzenoid - Keto acid - N-acyl-amine - Methyl ester - Carbamic acid ester - Alpha-haloketone - Carbonic acid derivative - Ketone - Secondary carboxylic acid amide - Carboxamide group - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Hydrocarbon derivative - Alkyl halide - Organic nitrogen compound - Carbonyl group - Organic oxide - Organopnictogen compound - Alkyl fluoride - Organohalogen compound - Organofluoride - Organonitrogen compound - Organooxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

MAOA Tclin Monoamine oxidase A (11911 Activities)

Discover Target: MAOA

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

MAOB Tclin Monoamine oxidase B (8835 Activities)

Discover Target: MAOB

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

CASP3 Tchem Caspase-3 (3632 Activities)

Discover Target: CASP3

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

Jurkat (10389 Activities)

Explore this target

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

HeLa (62764 Activities)

Explore this target

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO to 20 mM
• Molecular Weight: 467.500 g/mol
• XLogP3: 1.900
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 14
• Exact Mass: 467.207 Da
• Monoisotopic Mass: 467.207 Da
• Topological Polar Surface Area: 140.000 Ų
• Heavy Atom Count: 33
• Formal Charge: 0
• Complexity: 695.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

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2. Chen Yuxing, Tao Yong, Huang Qiu, Xu Jingtao, Wang Zhenxin, Zhang Ye, Fu Guangxu, Tan Fuqiang, Feng Keyi, Ou Yunsheng.  (2025)  Hino-Fe Chelate Suppresses Osteosarcoma Progression through Dual Induction of Ferroptosis and NLRC4-mediated Pyroptosis: Mechanisms and Therapeutic Implications.  International Journal of Biological Sciences,  21  (11): (4872-4894).  [PMID:40860199] [10.7150/ijbs.113785]

3. Liyun Zheng, Zhongwei Zhao, Li Chen, Wenjing Yang, Giorgio Ercolani, Pan Qin, Bin Lin, Mengzhu Han, Qiaoyou Weng, Yeyu Zhang, Bin Wu, Minjiang Chen, Zouying Yao, Shiji Fang, Jiansong Ji.  (2025)  Astragalin Induces Immunogenic Cell Death in Liver Cancer by Targeting NQO2 to Promote ROS-Mediated Endoplasmic Reticulum Stress Pathway.  FREE RADICAL BIOLOGY AND MEDICINE,      [PMID:40749898] [10.1016/j.freeradbiomed.2025.07.047]

4. Lei Shu, Peili Luo, Chuanyu Ren, Ziwei Lai, Xuejuan Zhang, Chuanbin Wu, Xin Pan, Zhengwei Huang.  (2025)  Inhalable Fibroin Hybrid Liposomes for the Targeted Treatment of Lung Adenocarcinoma via Autophagy-Enhanced Ferroptosis.  ACS Nano,      [PMID:40878028] [10.1021/acsnano.5c09493]

5. Shichen Zhang, Lei Guo, Yixin Tang, Yixing Wang, Heshi Liu, Chang Liu, Xiuzhang Yan, Congcong Duan, Huanyan Dai, Bing Han, Caina Xu.  (2025)  Self-reinforced nanoreactor for apoptosis/ferroptosis synergistic therapy of head and neck squamous cell carcinoma.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.166941]

6. Bo Xu, Zezhu Zhou, Jiaqi Fang, Jianguang Wang, Kun Tao, Junjian Liu, Shuhao Liu.  (2023)  Exosomes derived from schwann cells alleviate mitochondrial dysfunction and necroptosis after spinal cord injury via AMPK signaling pathway-mediated mitophagy.  FREE RADICAL BIOLOGY AND MEDICINE,      [PMID:37640169] [10.1016/j.freeradbiomed.2023.08.026]

7. Bo Xu, Jiaqi Fang, Jianguang Wang, Xuehan Jin, Shengfu Liu, Kaihang Song, Ping Wang, Junjian Liu, Shuhao Liu.  (2023)  Inhibition of autophagy and RIP1/RIP3/MLKL-mediated necroptosis by edaravone attenuates blood spinal cord barrier disruption following spinal cord injury.  BIOMEDICINE & PHARMACOTHERAPY,      [PMID:37459660] [10.1016/j.biopha.2023.115165]

8. Ju Yang, Ping Liu, Dan Ma, Peng Zhao, Yan Zhang, Yinghao Lu, Yanju Li, Yi Huang, Ying Chen, Jishi Wang.  (2020)  Glucocorticoid resistance induced by ANXA5 overexpression in B-cell acute lymphoblastic leukemia.  PEDIATRIC HEMATOLOGY AND ONCOLOGY,      [PMID:33231128] [10.1080/08880018.2020.1810182]

9. Wu Chuanhong, Zhao Wenwen, Yu Jie, Li Shaojing, Lin Ligen, Chen Xiuping.  (2018)  Induction of ferroptosis and mitochondrial dysfunction by oxidative stress in PC12 cells.  Scientific Reports,  8  (1): (1-11).  [PMID:29330409] [10.1038/s41598-017-18935-1]

10. Fang Liu, Yaru Li, Yao Li, Zheng Wang, Xin Li, Yancheng Liu, Yanjun Zhao.  (2024)  Triggering multiple modalities of cell death via dual-responsive nanomedicines to address the narrow therapeutic window of β-lapachone.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:39270391] [10.1016/j.jcis.2024.09.063]

11. Yu-Zhang Wang, Wei-Hai Chen, Zi-Yi Han, Shi-Man Zhang, Ping Ji, Cheng Zhang, Jun-Long Liang, Xian-Zheng Zhang.  (2025)  Targeted tumor therapy with L-cyst(e)ine-addicted bacteria-nanodrug biohybrids.  Cell Metabolism,      [PMID:40215982] [10.1016/j.cmet.2025.03.012]