N-[2-({[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl](methyl)amino}methyl)phenyl]-2-hydroxy-S'-(4-methoxyphenyl)ethane-1-sulfonamido; phosphoric acid

• ChemBase ID: 134253
• Molecular Formular: C26H32ClN2O8PS
• Molecular Mass: 599.032641
• Monoisotopic Mass: 598.1305513
• SMILES: CN(C/C=C/c1ccc(cc1)Cl)Cc1ccccc1N(CCO)S(=O)(=O)c1ccc(cc1)OC.OP(=O)(O)O
• Canonical SMILES: OP(=O)(O)O.OCCN(S(=O)(=O)c1ccc(cc1)OC)c1ccccc1CN(C/C=C/c1ccc(cc1)Cl)C
• InChI: InChI=1S/C26H29ClN2O4S.H3O4P/c1-28(17-5-6-21-9-11-23(27)12-10-21)20-22-7-3-4-8-26(22)29(18-19-30)34(31,32)25-15-13-24(33-2)14-16-25;1-5(2,3)4/h3-16,30H,17-20H2,1-2H3;(H3,1,2,3,4)/b6-5+
• InChIKey: NNKJTPOXLIILMB-IPZCTEOASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[2-({[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl](methyl)amino}methyl)phenyl]-2-hydroxy-S'-(4-methoxyphenyl)ethane-1-sulfonamido; phosphoric acid
• IUPAC Traditional name: N-[2-({[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl](methyl)amino}methyl)phenyl]-2-hydroxy-S'-(4-methoxyphenyl)ethanesulfonamido; phosphoric acid
• Synonyms: N-[2-[N-(4-Chlorocinnamyl)-N-methylaminomethyl]phenyl]-N-(2-hydroxyethyl)-4-methoxybenzenesulfonamide phosphate salt; N-[2-[[[3-(4′-Chlorophenyl)-2-propenyl]methylamino]methyl]phenyl]-N-(2-hydroxyethyl)-4′-methoxybenzenesulfonamide phosphate salt; KN-93

Database IDs

• CAS Number: 139298-40-1
• MDL Number: MFCD03788201
• PubChem SID: 162228530
• PubChem CID: 16760530

CALCULATED PROPERTIES

• Acid pKa: 15.527495
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.273763
• LogD (pH = 7.4): 4.034938
• Log P: 4.7166443
• Molar Refractivity: 138.8211 cm^3
• Polarizability: 54.022114 Å^3
• Polar Surface Area: 70.08 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble1 mg/mL; H2O: soluble
• Apperance: white

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - K1385

Frequently Asked Questions
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Caution
Photosensitive
Biochem/physiol Actions
KN-93 is a selective Ca2+/calmodulin-dependent protein kinase II inhibitor, which has been implicated in the regulation of smooth muscle contractility. CaM kinase II activation was inhibited by KN-93 pretreatment (IC50 ~1 μM). KN-93 inhibited histamine-induced tonic force maintenance, whereas early force development and MLC20 phosphorylation responses during the entire time course were unaffected. Both force development and maintenance in response to KCl were inhibited by KN-93. Rapid increases in KCl-induced MLC20 phosphorylation were also inhibited by KN-93, whereas steady-state MLC20 phosphorylation responses were unaffected. In contrast, phorbol 12,13-dibutyrate (PDBu) did not activate CaM kinase II and PDBu-stimulated force development was unaffected by KN-93. Thus KN-93 appears to target a step(s) essential for force maintenance in response to physiological stimuli, suggesting a role for CaM kinase II in regulating tonic contractile responses in arterial smooth muscle. Pharmacological activation of protein kinase C bypasses the KN-93 sensitive step.