(1R,2R,9S,17S)-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-en-6-one

• ChemBase ID: 73024
• Molecular Formular: C15H22N2O
• Molecular Mass: 246.34798
• Monoisotopic Mass: 246.17321333
• SMILES: C1=CC(=O)N2[C@H](C1)[C@@H]1[C@@H]3[C@H](C2)CCCN3CCC1
• Canonical SMILES: O=C1C=CC[C@H]2N1C[C@@H]1CCCN3[C@@H]1[C@@H]2CCC3
• InChI: InChI=1S/C15H22N2O/c18-14-7-1-6-13-12-5-3-9-16-8-2-4-11(15(12)16)10-17(13)14/h1,7,11-13,15H,2-6,8-10H2/t11-,12+,13+,15-/m0/s1
• InChIKey: AAGFPTSOPGCENQ-JLNYLFASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,9S,17S)-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-en-6-one; (1R,2R,9S,17S)-7,13-diazatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadec-4-en-6-one
• IUPAC Traditional name: (1R,2R,9S,17S)-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-en-6-one; (1R,2R,9S,17S)-7,13-diazatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadec-4-en-6-one
• Synonyms: Sophocarpine; 13,14-Didehydromatridin-15-one; Sophocarpine

Database IDs

• CAS Number: 6483-15-4
• PubChem SID: 162037944
• PubChem CID: 115269

CALCULATED PROPERTIES

• Acid pKa: 17.835543
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -2.366152
• LogD (pH = 7.4): -1.3124717
• Log P: 1.0737509
• Molar Refractivity: 72.5418 cm^3
• Polarizability: 27.934605 Å^3
• Polar Surface Area: 23.55 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2405

Research Area: Cardiovascular Disease
Biological Activity:
Sophocarpine is a human ether-à-go-go-related gene (HERG) inhibitor with an IC(50) of about 0.2 mM. Sophocarpine (SC) were examined on stably expressed HERG channels in human embryonic kidney (HEK293) cells using a whole-cell patch clamp technique, Western blot analysis and immunofluorescence experiments. Sophocarpine inhibited HERG channels in a concentration-dependent manner. Sophocarpine significantly accelerated channel inactivation, recovery from inactivation and onset of inactivation. In addition, it had no effect on channel activation and deactivation. Based on Western blot and immunofluorescence results, SC had no significant effect on the expression of HERG protein. [1][2]

REFERENCES

• Zhao XL et al. Biol Pharm Bull. 2008 Apr;31(4):627-32.