(1R,9R)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,10-trien-5-one

• ChemBase ID: 72912
• Molecular Formular: C15H18N2O
• Molecular Mass: 242.31622
• Monoisotopic Mass: 242.14191321
• SMILES: C1(=C[C@H]2Cc3c([C@@](C1)(/C/2=C/C)N)ccc(=O)[nH]3)C
• Canonical SMILES: C/C=C/1\[C@H]2C=C(C[C@]1(N)c1c(C2)[nH]c(=O)cc1)C
• InChI: InChI=1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/b11-3+/t10?,15-/m1/s1
• InChIKey: ZRJBHWIHUMBLCN-JYXJEATCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9R)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,10-trien-5-one
• IUPAC Traditional name: (1R,9R)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,10-trien-5-one
• Synonyms: (-)-Huperzine A

Database IDs

• CAS Number: 102518-79-6
• PubChem SID: 162037832
• PubChem CID: 907504

CALCULATED PROPERTIES

• Acid pKa: 11.107823
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -2.3114355
• LogD (pH = 7.4): -1.0717244
• Log P: 0.6177158
• Molar Refractivity: 75.795 cm^3
• Polarizability: 27.949518 Å^3
• Polar Surface Area: 55.12 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2251

Research Area: Neurological Disease
Biological Activity:
(-)-Huperzine A is an Acetylcholinesterase inhibitor and NMDA receptor antagonist with an IC50 of 126 μM for NMDA-induced current. Huperzine A, is a naturally occurring sesquiterpene alkaloid compound found in the plant firmoss Huperzia serrata. The IC(50) values of huperzine A were neither altered by changing the concentrations of glycine (2-0.2 μM) and pH (7.4-6.7) in the external solution, nor by addition of Zn(2+) (5 μM) and dithiothreitol (5 mM) to the external solution. [1][2]References on (-)-Huperzine A[1] http://en.wikipedia.org/wiki/Huperzine_A, , [2] Neuroscience., 2001, 105(3):663-9.

REFERENCES

• Zhang JM et al. Neuroscience. 2001;105(3):663-9.