N-p-Tosyl-L-phenylalanine chloromethyl ketone(TPCK) - Moligand™, ≥97% , CAS No.402-71-1

CAS: 402-71-1 Cat. No.: T123226 Molecular Weight: 351.85 Beilstein Registry Number: 2895215 EC Number: 206-954-6

GRADE & PURITY Moligand™, ≥97%

Synonyms

TPCK | C02088 | NCGC00016020-01 | O-tert-Butylhydroxylamine hydrochloride, >=99% | N-P-tosyl-L-phenylalanyl chloromethyl ketone | NSC 727365 | l-N-(alpha-(Chloroacetyl)phenethyl)-p-toluenesulfonamide | NCGC00094419-03 | Tosyl-L-phenylalanylchloromethane |

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

N-p-Tosyl-L-phenylalanine chloromethyl ketone has been used: to investigate whether transcription factor NFκB is involved in renalase expression to test the role of NF-κB activation to study its inhibitory effect on chymotrypsin

Specifications

Synonyms

TPCK | C02088 | NCGC00016020-01 | O-tert-Butylhydroxylamine hydrochloride, >=99% | N-P-tosyl-L-phenylalanyl chloromethyl ketone | NSC 727365 | l-N-(alpha-(Chloroacetyl)phenethyl)-p-toluenesulfonamide | NCGC00094419-03 | Tosyl-L-phenylalanylchloromethane |

Specifications & Purity

Moligand™, ≥97%

Biochemical and Physiological Mechanisms

Blocks the LPS- or cytokine-induced activation of nuclear factor κB (NFκB), which, in turn, blocks the induction of iNOS and COX-2 transcription. Blocks activation of pp70s6k by all mitogens. Blocks apoptosis cell lines by inhibiting the processing of cas

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

ACTIVATOR

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 month. 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

≥97%

Names and Identifiers

• Pubchem Sid: 488189751
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488189751
• Canonical Smiles: CC1=CC=C(C=C1)S(=O)(=O)NC(CC2=CC=CC=C2)C(=O)CCl
• IUPAC Name: N-[(2S)-4-chloro-3-oxo-1-phenylbutan-2-yl]-4-methylbenzenesulfonamide
• InChIKey: MQUQNUAYKLCRME-INIZCTEOSA-N
• INCHI: 1S/C17H18ClNO3S/c1-13-7-9-15(10-8-13)23(21,22)19-16(17(20)12-18)11-14-5-3-2-4-6-14/h2-10,16,19H,11-12H2,1H3/t16-/m0/s1
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)N[C@@H](CC2=CC=CC=C2)C(=O)CCl
• RTECS: XT5613500
• Molecular Weight: 351.85
• Beilstein: 2895215
• Reaxy-Rn: 2895215
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2895215&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Toluenes
        • Level5 Tosyl compounds
          • Level6 P-toluenesulfonamides

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Toluenes
• Intermediate Tree Nodes: Tosyl compounds
• Direct Parent: P-toluenesulfonamides
• Alternative Parents: Benzenesulfonamides Amphetamines and derivatives Benzenesulfonyl compounds Organosulfonamides Aminosulfonyl compounds Alpha-chloroketones Organopnictogen compounds Organonitrogen compounds Organochlorides Organic oxides Hydrocarbon derivatives Alkyl chlorides
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: P-toluenesulfonamide - Amphetamine or derivatives - Benzenesulfonamide - Benzenesulfonyl group - Organosulfonic acid amide - Alpha-haloketone - Alpha-chloroketone - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Aminosulfonyl compound - Sulfonyl - Ketone - Organic oxide - Organopnictogen compound - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Alkyl chloride - Carbonyl group - Organic oxygen compound - Organic nitrogen compound - Alkyl halide - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as p-toluenesulfonamides. These are aromatic heterocyclic compounds containing a toluene that is p-substituted with a sulfonamide group.
• External Descriptors: sulfonamide - alpha-chloroketone

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)

VDR Tclin Vitamin D receptor (26531 Activities)

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TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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PTH1R Tclin Parathyroid hormone receptor (47172 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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CMA1 Tchem Chymase (726 Activities)

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CTSG Tchem Cathepsin G (2304 Activities)

Discover Target: CTSG

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APP Tclin Amyloid-beta A4 protein (8510 Activities)

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PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

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MTOR Tclin Serine/threonine-protein kinase mTOR (13850 Activities)

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NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)

Discover Target: NFKB1

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CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

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CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

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CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

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A498 (42825 Activities)

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ACHN (49357 Activities)

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CCRF-CEM (65223 Activities)

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COLO 205 (50209 Activities)

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DU-145 (51482 Activities)

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HL-60 (67320 Activities)

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HT-29 (80576 Activities)

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K562 (73714 Activities)

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M14 (47487 Activities)

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MCF7 (126967 Activities)

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OVCAR-3 (48710 Activities)

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OVCAR-4 (44535 Activities)

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OVCAR-5 (45555 Activities)

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OVCAR-8 (47708 Activities)

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PC-3 (62116 Activities)

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RXF 393 (41971 Activities)

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SF-295 (48000 Activities)

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SH-SY5Y (11521 Activities)

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SK-MEL-2 (46422 Activities)

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SK-MEL-28 (48833 Activities)

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SK-MEL-5 (47095 Activities)

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SK-OV-3 (52876 Activities)

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SN12C (47755 Activities)

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SNB-19 (46794 Activities)

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TK-10 (45540 Activities)

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U-251 (51189 Activities)

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UACC-257 (46019 Activities)

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UACC-62 (47335 Activities)

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UO-31 (46270 Activities)

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786-0 (47912 Activities)

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A549 (127892 Activities)

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NCI/ADR-RES (33767 Activities)

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Associated Targets(non-human)

Alpha-chymotrypsin (819 Activities)

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Papain (844 Activities)

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Trypsin (394 Activities)

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Cruzipain (33337 Activities)

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Mapk1 MAP kinase ERK2 (650 Activities)

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CELA2A Elastase 2A (403 Activities)

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Saccharomyces cerevisiae (19171 Activities)

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Plasmodium falciparum (966862 Activities)

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Mus musculus (284745 Activities)

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RAW264.7 (28094 Activities)

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Ehrlich (1318 Activities)

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dnaB Replicative DNA helicase (15 Activities)

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lef Anthrax lethal factor (7585 Activities)

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Npsr1 Neuropeptide S receptor (260 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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pfk 6-phospho-1-fructokinase (7870 Activities)

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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

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TGR Thioredoxin glutathione reductase (28579 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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Impa1 Inositol monophosphatase 1 (16203 Activities)

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nfo Endonuclease 4 (425 Activities)

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NS1 Nonstructural protein 1 (33327 Activities)

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recA Protein RecA (2211 Activities)

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TIM23 Mitochondrial import inner membrane translocase subunit TIM23 (781 Activities)

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TIM10 Mitochondrial import inner membrane translocase subunit TIM10 (1435 Activities)

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hsp60 Chaperonin GroEL (Thermosome, HSP60 family) (16 Activities)

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Parl Presenilins-associated rhomboid-like protein, mitochondrial (3 Activities)

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groL GroEL/GroES (1042 Activities)

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glpG Rhomboid protease GlpG (20 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO: >10 mg/mL (stable for several months at 4°C.) ethanol: 20 mg/mL (stable for several months at 4°C. Stock solutions (10 mM in methanol or ethanol) are stable for several months at 4°C.)
• Sensitivity: heat sensitive
• Specific Rotation[α]: -87.0 to -91.0 deg(C=1, EtOH)
• Melt Point(°C): 106.0 to 110.0 °C
• Molecular Weight: 351.800 g/mol
• XLogP3: 3.600
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 351.07 Da
• Monoisotopic Mass: 351.07 Da
• Topological Polar Surface Area: 71.600 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 475.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• 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

1. Yi-ni Lu, Xiao-han Wang, Bo-cheng Xu, Yufen Zheng, Xiong Zhang, Yi Liu, Tian-yin Wang, Feng Yu.  (2025)  Urinary Trypsin Inhibitor Exerts Multifaceted Regulation of Angiopoietin 2 in Septic Cardiomyopathy.  EUROPEAN JOURNAL OF PHARMACOLOGY,      [PMID:40651788] [10.1016/j.ejphar.2025.177944]