(1R,9R)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,10-trien-5-one

• ChemBase ID: 1695
• Molecular Formular: C15H18N2O
• Molecular Mass: 242.31622
• Monoisotopic Mass: 242.14191321
• SMILES: c1(=O)[nH]c2c(cc1)[C@@]1(/C(=C/C)/[C@H](C2)C=C(C1)C)N
• 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+/m0/s1
• InChIKey: ZRJBHWIHUMBLCN-YQEJDHNASA-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; (1R,9R,13E)-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; (1R,9R,13E)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,10-trien-5-one
• Synonyms: HupA; Huperzine A; Huperaine A

Database IDs

• CAS Number: 102518-79-6
• PubChem SID: 160965152; 46507021
• PubChem CID: 854026
• CHEMBL: 395280
• Chemspider ID: 16736021
• DrugBank ID: DB01928
• Wikipedia Title: Huperzine_A

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 1.78
• LOG S: -3.16
• Solubility (Water): 1.66e-01 g/l

PROPERTIES

Physical Property

• Melting Point: 217–219 °C

DETAILS

DrugBank - DB01928

Drug information: experimental