(1R)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,10-trien-5-one

• ChemBase ID: 170236
• Molecular Formular: C15H18N2O
• Molecular Mass: 242.31622
• Monoisotopic Mass: 242.14191321
• SMILES: [nH]1c2c(ccc1=O)[C@@]1(/C(=C/C)/C(C2)C=C(C1)C)N
• Canonical SMILES: C/C=C/1\C2C=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)-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)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0^2,^7]trideca-2(7),3,10-trien-5-one
• Synonyms: HUP; [5R-(5α,9β-11E)]-5-Amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2-(1H)-one; Selagine,; (-)-Huperzine A

Database IDs

• CAS Number: 102518-79-6
• PubChem SID: 164226146
• PubChem CID: 59922556

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

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: 223-226°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H826000

Reversible alkaloid inhibitor of AChE which crosses the blood-brain barrier. A potential therapeutic agent for Alzheimer’s disease. It reduces cell death induced by glutamate in primary cultures derived from forebrain, hippocampus, cortex and cerebellum

REFERENCES

• Wang, Y.-E., et al.: Acta Pharmacol. Sin., 7, 110 (1986)
• Ved, H.S., et al.: Neuroreport, 8, 963 (1997)