(2S,3aS,7aS)-1-[(1R,2R)-2-phenylcyclopropanecarbonyl]-2-(1,3-thiazolidine-3-carbonyl)-octahydro-1H-indole

• ChemBase ID: 153297
• Molecular Formular: C22H28N2O2S
• Molecular Mass: 384.53492
• Monoisotopic Mass: 384.18714915
• SMILES: c1ccc(cc1)[C@@H]1C[C@H]1C(=O)N1[C@H]2CCCC[C@H]2C[C@H]1C(=O)N1CCSC1
• Canonical SMILES: O=C([C@@H]1C[C@H]1c1ccccc1)N1[C@H]2CCCC[C@H]2C[C@H]1C(=O)N1CSCC1
• InChI: InChI=1S/C22H28N2O2S/c25-21(18-13-17(18)15-6-2-1-3-7-15)24-19-9-5-4-8-16(19)12-20(24)22(26)23-10-11-27-14-23/h1-3,6-7,16-20H,4-5,8-14H2/t16-,17-,18+,19-,20-/m0/s1
• InChIKey: NXSXRIHXEQSYEZ-KNJMJIDISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3aS,7aS)-1-[(1R,2R)-2-phenylcyclopropanecarbonyl]-2-(1,3-thiazolidine-3-carbonyl)-octahydro-1H-indole
• IUPAC Traditional name: (2S,3aS,7aS)-1-[(1R,2R)-2-phenylcyclopropanecarbonyl]-2-(1,3-thiazolidine-3-carbonyl)-octahydroindole
• Synonyms: (2S,3aS,7aS)-1-(((R,R)-2-Phenylcyclopropyl)carbonyl)-2-((thiazolidin-3-yl)carbonyl)octahydro-1H-indole; [(2S,3aS,7aS)-Octahydro-1-[[(1R,2R)-2-phenylcyclopropyl]carbonyl]-1H-indol-2-yl]-3-thiazolidinyl--methanone; S 17092

Database IDs

• CAS Number: 176797-26-5
• MDL Number: MFCD00948255
• PubChem SID: 162247436
• PubChem CID: 9929984

CALCULATED PROPERTIES

• Acid pKa: 19.776373
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.9049432
• LogD (pH = 7.4): 2.904944
• Log P: 2.904944
• Molar Refractivity: 107.8026 cm^3
• Polarizability: 42.360676 Å^3
• Polar Surface Area: 40.62 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: white to tan powder
• Optical Rotation: [α]/D -140 to -170° in dichloromethane

Safety Information

• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H28N2O2S

DETAILS

Sigma Aldrich - SML0181

Biochem/physiol Actions
S-17092 is a potent, selective inhibitor of Prolyl oligopeptidase (POP), also known as prolyl endopeptidase (PEP or PE). Ki=1.5 nM. Nootropic. S-17092 inhibition of POP prevents breakdown and thus increases the activity of a number of neuropeptides, which is likely the basis for its nootropic activity. S 17092 has been shown to improve cognition. It improved cognitive task performance in chronic low dose MPTP-treated monkeys. S-17092 was recently used to inhibit the formation of AcSDKP from its precursor 43-mer thymosin ?4 (T?4). Ac-SDKP is involved in hemopoietic stem cell differentiation, is pro-angiogenic and antifibrogenic.