(3S)-7-amino-1-chloro-S-(4-methylphenyl)-2-oxoheptane-3-sulfonamido hydrochloride

• ChemBase ID: 103568
• Molecular Formular: C14H22Cl2N2O3S
• Molecular Mass: 369.30708
• Monoisotopic Mass: 368.07281893
• SMILES: Cl.Cc1ccc(cc1)S(=O)(=O)N[C@@H](CCCCN)C(=O)CCl
• Canonical SMILES: NCCCC[C@@H](C(=O)CCl)NS(=O)(=O)c1ccc(cc1)C.Cl
• InChI: InChI=1S/C14H21ClN2O3S.ClH/c1-11-5-7-12(8-6-11)21(19,20)17-13(14(18)10-15)4-2-3-9-16;/h5-8,13,17H,2-4,9-10,16H2,1H3;1H/t13-;/m0./s1
• InChIKey: YFCUZWYIPBUQBD-ZOWNYOTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-7-amino-1-chloro-S-(4-methylphenyl)-2-oxoheptane-3-sulfonamido hydrochloride
• IUPAC Traditional name: C14H21ClN2O3S hydrochloride
• Synonyms: (3S)-1-Chloro-3-tosylamido-7-amino-2-heptanone hydrochloride; (3S)-7-Amino-1-chloro-3-tosylamino-2-heptanone hydrochloride; Tosyl-L-lysyl-chloromethane hydrochloride; Nα-Tosyl-L-lysine chloromethyl ketone hydrochloride; TLCK; 1-Chloro-3-tosylamido-7-amino-L-2-heptanone; Tos-Lys-chloromethylketone hydrochloride; N-α-p-TOSYL-L-LYSINE CHLOROMETHYL KETONE

Database IDs

• CAS Number: 4238-41-9; 4272-74-6
• EC Number: 224-266-4; 224-199-0
• MDL Number: MFCD00065395
• Beilstein Number: 7106867
• PubChem SID: 24889312; 24278752; 162103011
• PubChem CID: 73093

CALCULATED PROPERTIES

• Acid pKa: 10.396283
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.9192657
• LogD (pH = 7.4): -0.34327915
• Log P: 1.6378839
• Molar Refractivity: 84.3488 cm^3
• Polarizability: 33.71932 Å^3
• Polar Surface Area: 89.26 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL
• Apperance: powder
• Melting Point: 155°C (dec.)
• Optical Rotation: [α]20/D -7.8±0.5°, c = 2% in H2O

Safety Information

• Storage Condition: 0°C, Desiccate
• RTECS: XT5160000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; R:36
• Safety Statements: 26-36; S:26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... NFKB1(4790), NFKB2(4791)

Product Information

• Purity: ≥96% (TLC); ≥99.0% (AT)
• Potency: 10-100 μM effective concentration
• Empirical Formula (Hill Notation): C14H21ClN2O3S · HCl

DETAILS

MP Biomedicals - 02152152

Hydrochloride
Crystalline Inhibitor of papain and trypsin. Also a specific reagent for essential histidine site in trypsin.

Sigma Aldrich - T7254

Biochem/physiol Actions
Blocks the LPS- or cytokine-induced activation of nuclear factor κB (NF-κB), which, in turn, blocks the induction of iNOS and COX-2 transcription. Blocks activation of pp70s6k by all mitogens. Blocks apoptosis in cell lines by inhibiting the processing of caspases in some cell lines and to some stimuli.
Caution
Stable at least two years when stored desiccated at -20°C.

Sigma Aldrich - 90182

Other Notes
An alkylating reagent that may react with histidine or cysteine residues at the active site of enzymes. Inactivates serine proteases such as trypsin 1,2,3 and clostripain 4. Chymotrypsin is not affected. To prevent proteolytic degradation, a combination of TLCK and TPCK can be used throughout the isolation of proteins, as in the isolation of histones.5