(2S)-4-chloro-S-(4-methylphenyl)-3-oxo-1-phenylbutane-2-sulfonamido

• ChemBase ID: 137300
• Molecular Formular: C17H18ClNO3S
• Molecular Mass: 351.84772
• Monoisotopic Mass: 351.06959212
• SMILES: Cc1ccc(cc1)S(=O)(=O)N[C@@H](Cc1ccccc1)C(=O)CCl
• Canonical SMILES: ClCC(=O)[C@@H](NS(=O)(=O)c1ccc(cc1)C)Cc1ccccc1
• InChI: 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
• InChIKey: MQUQNUAYKLCRME-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-4-chloro-S-(4-methylphenyl)-3-oxo-1-phenylbutane-2-sulfonamido
• IUPAC Traditional name: TPCK
• Synonyms: (S)-1-Chloro-3-tosylamido-4-phenyl-2-butanone; (S)-1-Chloro-4-phenyl-3-tosylamido-2-butanone; N-p-Tosyl-L-phenylalanine chloromethyl ketone; TPCK; Tosyl-L-phenylalanyl-chloromethane; L-1-p-Tosylamino-2-phenylethyl chloromethyl ketone; N-p-Tosyl-L-phenylalanine chloromethyl ketone

Database IDs

• CAS Number: 402-71-1
• EC Number: 206-954-6
• MDL Number: MFCD00000935
• Beilstein Number: 2895215
• PubChem SID: 162231564; 24278737
• PubChem CID: 439647

CALCULATED PROPERTIES

• Acid pKa: 10.168556
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.886409
• LogD (pH = 7.4): 3.8857622
• Log P: 3.8864174
• Molar Refractivity: 91.6556 cm^3
• Polarizability: 36.23309 Å^3
• Polar Surface Area: 63.24 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL (stable for several months at 4°C.); ethanol: soluble20 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.)
• Apperance: white powder
• Melting Point: 106-108 °C(lit.)

Safety Information

• RTECS: XT5613500
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 37/38-41
• Safety Statements: 26-36
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... NFKB1(4790), NKAP(79576), NKRF(55922), NOS2(4843), PTGS2(5743)

Product Information

• Purity: ≥97% (TLC); ≥99%
• Potency: 10-100 μM effective concentration
• Linear Formula: C6H5CH2CH(NHSO2C6H4CH3)COCH2Cl
• Empirical Formula (Hill Notation): C17H18ClNO3S

DETAILS

Sigma Aldrich - T4376

Application
Irreversible inhibitor of certain serine proteases; used to inhibit chymotrypsin in preparations of trypsin.
Caution
Shelf-life is at least two years when stored desiccated at -20 °C.
Biochem/physiol Actions
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 caspases in some cell lines and to some stimuli. Also blocks apoptosis initiated by Taxol (in MCF-7 human breast carcinoma cells).1

Sigma Aldrich - 857254

Application
Protease inhibitor.