Z-WEHD-FMK - ≥98% , CAS No.210345-00-9

CAS: 210345-00-9 Cat. No.: Z646640 Molecular Weight: 763.77 PubChem CID: 25108687

GRADE & PURITY ≥98%

Synonyms

benzyloxycarbonyl-Trp-Glu(OMe)-His-Asp(OMe)-fluoromethylketone | HY-P0111 | Caspase-1/ICE Inhibitor Z-WEHD-FMK | Z-WEHD-FMK | L-Histidinamide, N-[(phenylmethoxy)carbonyl]-L-tryptophyl-L- | DTXSID80648727 | methyl (4S)-5-[[(2S)-1-[[(3S)-5-fluoro-1-methoxy-

Storage

Desiccated,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Z-WEHD-FMK is a potent, cell-permeable and irreversible caspase-1/5 inhibitor. Z-WEHD-FMK also exhibits a robust inhibitory effect on cathepsin B activity ( IC 50 =6 μM). Z-WEHD-FMK can be used to investigate cells for evidence of apoptosis.

In Vitro

Z-WEHD-FMK (80 μM; 9 hours) elicits a near-complete blockage of C. trachomatis -induced cleavage of golgin-84 and increases GM130 expression in cells. Z-WEHD-FMK (30 min before being exposed to E. piscicida ) effectively inhibits 0909I E. piscicida induced ZF4 cells cytotoxicity and pyroptotic morphology. And in addition, it also inhibits the cytotoxicity induced by cytosolic LPS delivery. Z-WEHD-FMK (20 μM;18-24 hours following Cr 3+ ,Ni 2+ , and Co 2+ ) significantly induces a decrease of 76% to 86% in IL-1β release with 200 to 400 ppm Cr 3+ , it also induces a decrease of 35% to 45% with 48 ppm Ni 2+ or higher, Finally, this caspase-1 inhibitor induced a decrease with 6 ppm Co 2+ , down to a level below the detection threshold, and a decrease of 40% to 48% with 12 to 24 ppm Co 2+ in bone marrow-derived macrophages (BMDM). MCE has not independently confirmed the accuracy of these methods. They are for reference only. Western Blot AnalysisCell Line: C. trachomatis - or mock-infected HeLa cells Concentration: 80 μM Incubation Time: 9 hours Result: Increased golgin-84 and GM130 expression. Cell Viability AssayCell Line: Mycoplasma free-ZF4 cells Concentration: Incubation Time: 30 min before being exposed to E. piscicida Result: Inhibited ZF4 cells cytotoxicity and pyroptotic morphology.

Form:Solid

IC50& Target:Cathepsin B|Caspase-1

Specifications

Synonyms

benzyloxycarbonyl-Trp-Glu(OMe)-His-Asp(OMe)-fluoromethylketone | HY-P0111 | Caspase-1/ICE Inhibitor Z-WEHD-FMK | Z-WEHD-FMK | L-Histidinamide, N-[(phenylmethoxy)carbonyl]-L-tryptophyl-L- | DTXSID80648727 | methyl (4S)-5-[[(2S)-1-[[(3S)-5-fluoro-1-methoxy-

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Z-WEHD-FMK is a potent, cell-permeable and irreversible caspase-1/5 inhibitor. Z-WEHD-FMK also exhibits a robust inhibitory effect on cathepsin B activity ( IC 50 =6 μM). Z-WEHD-FMK can be used to investigate cells for evidence of apoptosis.

Storage

Desiccated, Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Purity

≥98%

Names and Identifiers

• Canonical Smiles: COC(=O)CCC(C(=O)NC(CC1=CN=CN1)C(=O)NC(CC(=O)OC)C(=O)CF)NC(=O)C(CC2=CNC3=CC=CC=C32)NC(=O)OCC4=CC=CC=C4
• IUPAC Name: methyl (4S)-5-[[(2S)-1-[[(3S)-5-fluoro-1-methoxy-1,4-dioxopentan-3-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-4-[[(2S)-3-(1H-indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoyl]amino]-5-oxopentanoate
• InChIKey: NLZNSSWGRVBWIX-KRCBVYEFSA-N
• INCHI: 1S/C37H42FN7O10/c1-53-32(47)13-12-27(34(49)44-30(15-24-19-39-21-41-24)36(51)43-28(31(46)17-38)16-33(48)54-2)42-35(50)29(14-23-18-40-26-11-7-6-10-25(23)26)45-37(52)55-20-22-8-4-3-5-9-22/h3-11,18-19,21,27-30,40H,12-17,20H2,1-2H3,(H,39,41)(H,42,50)(H,43,51)(H,44,49)(H,45,52)/t27-,28-,29-,30-/m0/s1
• Isomeric SMILES: COC(=O)CC[C@@H](C(=O)N[C@@H](CC1=CN=CN1)C(=O)N[C@@H](CC(=O)OC)C(=O)CF)NC(=O)[C@H](CC2=CNC3=CC=CC=C32)NC(=O)OCC4=CC=CC=C4
• Alternate CAS: 210345-00-9
• PubChem CID: 25108687
• Molecular Weight: 763.77

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: Histidine and derivatives Glutamic acid and derivatives N-acyl-alpha amino acids and derivatives Tryptamines and derivatives Alpha amino acid amides Beta amino acids and derivatives Benzyloxycarbonyls 3-alkylindoles Gamma-keto acids and derivatives Imidazolyl carboxylic acids and derivatives Fatty acid methyl esters N-acyl amines Substituted pyrroles Dicarboxylic acids and derivatives Methyl esters Alpha-haloketones Carbamate esters Heteroaromatic compounds Organic carbonic acids and derivatives Secondary carboxylic acid amides Azacyclic compounds Hydrocarbon derivatives Alkyl fluorides Organic oxides Organopnictogen compounds Organofluorides Organonitrogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Hybrid peptide - Histidine or derivatives - Glutamic acid or derivatives - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - Triptan - Beta amino acid or derivatives - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Benzyloxycarbonyl - 3-alkylindole - Indole - Indole or derivatives - Gamma-keto acid - Imidazolyl carboxylic acid derivative - Fatty acid ester - Fatty acid methyl ester - Dicarboxylic acid or derivatives - Fatty amide - Benzenoid - Keto acid - N-acyl-amine - Monocyclic benzene moiety - Fatty acyl - Substituted pyrrole - Carbamic acid ester - Methyl ester - Alpha-haloketone - Azole - Imidazole - Pyrrole - Heteroaromatic compound - Carbonic acid derivative - Carboxamide group - Ketone - Carboxylic acid ester - Secondary carboxylic acid amide - Organoheterocyclic compound - Carboxylic acid derivative - Azacycle - Hydrocarbon derivative - Organic oxygen compound - Organopnictogen compound - Carbonyl group - Organic nitrogen compound - Organohalogen compound - Organofluoride - Organonitrogen compound - Alkyl halide - Organooxygen compound - Organic oxide - Alkyl fluoride - Aromatic heteropolycyclic 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

Chemical and Physical Properties

• Solubility: DMSO : 100 mg/mL (130.93 mM; Need ultrasonic)
• Molecular Weight: 763.800 g/mol
• XLogP3: 2.000
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 23
• Exact Mass: 763.298 Da
• Monoisotopic Mass: 763.298 Da
• Topological Polar Surface Area: 240.000 Ų
• Heavy Atom Count: 55
• Formal Charge: 0
• Complexity: 1330.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• 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