N-[(2S)-1-{4-[(2S)-2-(2,4-dichlorobenzenesulfonamido)-3-hydroxypropanoyl]piperazin-1-yl}-4-methyl-1-oxopentan-2-yl]-1-benzothiophene-2-carboxamide

• ChemBase ID: 154220
• Molecular Formular: C28H32Cl2N4O6S2
• Molecular Mass: 655.61288
• Monoisotopic Mass: 654.11403212
• SMILES: CC(C)C[C@@H](C(=O)N1CCN(CC1)C(=O)[C@H](CO)NS(=O)(=O)c1ccc(cc1Cl)Cl)NC(=O)c1cc2ccccc2s1
• Canonical SMILES: OC[C@@H](C(=O)N1CCN(CC1)C(=O)[C@@H](NC(=O)c1cc2c(s1)cccc2)CC(C)C)NS(=O)(=O)c1ccc(cc1Cl)Cl
• InChI: InChI=1S/C28H32Cl2N4O6S2/c1-17(2)13-21(31-26(36)24-14-18-5-3-4-6-23(18)41-24)27(37)33-9-11-34(12-10-33)28(38)22(16-35)32-42(39,40)25-8-7-19(29)15-20(25)30/h3-8,14-15,17,21-22,32,35H,9-13,16H2,1-2H3,(H,31,36)/t21-,22-/m0/s1
• InChIKey: IVYQPSHHYIAUFO-VXKWHMMOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S)-1-{4-[(2S)-2-(2,4-dichlorobenzenesulfonamido)-3-hydroxypropanoyl]piperazin-1-yl}-4-methyl-1-oxopentan-2-yl]-1-benzothiophene-2-carboxamide
• IUPAC Traditional name: N-[(2S)-1-{4-[(2S)-2-(2,4-dichlorobenzenesulfonamido)-3-hydroxypropanoyl]piperazin-1-yl}-4-methyl-1-oxopentan-2-yl]-1-benzothiophene-2-carboxamide
• Synonyms: (N-((1S)-1-{[4-((2S)-2-{[(2,4-Dichlorophenyl)sulfonyl]amino}-3-hydroxypropanoyl)-1-piperazinyl]carbonyl}-3-methylbutyl)-1-benzothiophene-2-carboxamide; GSK1016790A

Database IDs

• CAS Number: 942206-85-1
• MDL Number: MFCD12912413
• PubChem SID: 162248359
• PubChem CID: 23630211

CALCULATED PROPERTIES

• Acid pKa: 9.0038185
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 3.3054123
• LogD (pH = 7.4): 3.2960832
• Log P: 3.305533
• Molar Refractivity: 161.547 cm^3
• Polarizability: 64.37221 Å^3
• Polar Surface Area: 136.12 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white solid

Safety Information

• German water hazard class: 1
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C28H32Cl2N4O6S2

DETAILS

Sigma Aldrich - G0798

Biochem/physiol Actions
GSK1016790A is a novel and potent TRPV4 channel agonist. The TRPV4 (transient receptor potential vanilloid 4) member of the TRP superfamily has been implicated in numerous physiological processes. GSK1016790A elicited Ca2+ influx in mouse and human TRPV4 expressing HEK cells (EC50 values of 18 and 2.1 nM, respectively), and evoked a dose-dependent activation of TRPV4 whole-cell currents at concentrations above 1 nM. It is 300 fold more potent than 4a-PDD (Cat. No. P8014).