(3R,5S,7s)-N-(2-benzamido-1,3-benzothiazol-6-yl)adamantane-1-carboxamide

• ChemBase ID: 154575
• Molecular Formular: C25H25N3O2S
• Molecular Mass: 431.5499
• Monoisotopic Mass: 431.16674806
• SMILES: c1ccc(cc1)C(=O)Nc1sc2c(n1)ccc(c2)NC(=O)[C@@]12C[C@H]3C[C@@H](C1)C[C@H](C2)C3
• Canonical SMILES: O=C(c1ccccc1)Nc1sc2c(n1)ccc(c2)NC(=O)[C@]12C[C@@H]3C[C@@H](C2)C[C@@H](C1)C3
• InChI: InChI=1S/C25H25N3O2S/c29-22(18-4-2-1-3-5-18)28-24-27-20-7-6-19(11-21(20)31-24)26-23(30)25-12-15-8-16(13-25)10-17(9-15)14-25/h1-7,11,15-17H,8-10,12-14H2,(H,26,30)(H,27,28,29)/t15-,16+,17-,25-
• InChIKey: MVSSJPGNLQPWSW-CIRRPZLZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,5S,7s)-N-(2-benzamido-1,3-benzothiazol-6-yl)adamantane-1-carboxamide
• IUPAC Traditional name: (3R,5S,7s)-N-(2-benzamido-1,3-benzothiazol-6-yl)adamantane-1-carboxamide
• Synonyms: N-[2-(benzoylamino)-6-benzothiazolyl]-Tricyclo[3.3.1.13,7]decane-1-carboxamide; adamantane-1-carboxylic acid (2-benzoylamino-benzothiazol-6-yl)amide; NVP-231

Database IDs

• CAS Number: 362003-83-6
• MDL Number: MFCD01988824
• PubChem SID: 162248713
• PubChem CID: 4096211

CALCULATED PROPERTIES

• Acid pKa: 9.394231
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.730386
• LogD (pH = 7.4): 5.7262793
• Log P: 5.7304387
• Molar Refractivity: 122.7431 cm^3
• Polarizability: 47.50711 Å^3
• Polar Surface Area: 71.09 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white to off-white powder

Safety Information

• German water hazard class: nwg
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C25H25N3O2S

DETAILS

Sigma Aldrich - N9289

Biochem/physiol Actions
Ceramide kinase presents an attractive target for drug development because of its involvement in cell growth and inflammation. CerK biology is still poorly understood thus discovery and availability of inhibitors will facilitate research at this area. NVP-231 is a newly discovered potent, specific and reversible CerK inhibitor that competitively inhibits binding of ceraminde to CerK.