(9S)-4,15-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,13,15-hexaene-3,5,16-triol

• ChemBase ID: 171609
• Molecular Formular: C19H21NO5
• Molecular Mass: 343.37374
• Monoisotopic Mass: 343.14197278
• SMILES: c1(c(cc2c(c1O)c1c3[C@H](C2)N(CCc3cc(c1O)OC)C)O)OC
• Canonical SMILES: COc1cc2CCN([C@@H]3c2c(c1O)c1c(C3)cc(c(c1O)OC)O)C
• InChI: InChI=1S/C19H21NO5/c1-20-5-4-9-8-13(24-2)17(22)16-14(9)11(20)6-10-7-12(21)19(25-3)18(23)15(10)16/h7-8,11,21-23H,4-6H2,1-3H3/t11-/m0/s1
• InChIKey: AFQNCKSXTUZMJD-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9S)-4,15-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadeca-1(17),2,4,6,13,15-hexaene-3,5,16-triol
• IUPAC Traditional name: (9S)-4,15-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadeca-1(17),2,4,6,13,15-hexaene-3,5,16-triol
• Synonyms: (6aS)-5,6,6a,7-Tetrahydro-2,10-dimethoxy-6-methyl-4H-dibenzo[de,g]quinoline-1,9-diol; 2,10-Dimethoxy-6aα-aporphine-1,9-diol; (+)-Isoboldine; (S)-(+)-Isoboldine; (S)-Isoboldine; N-Methyllaurelliptine; NSC 113983; d-Isoboldine; Isoboldine

Database IDs

• CAS Number: 3019-51-0
• PubChem SID: 164227519
• PubChem CID: 71749483

CALCULATED PROPERTIES

• Lipinski's Rule of Five: true
• Acid pKa: 9.253407
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 1.3284054
• LogD (pH = 7.4): 2.4025323
• Log P: 2.4753735
• Molar Refractivity: 94.8954 cm^3
• Polarizability: 37.241535 Å^3
• Polar Surface Area: 82.39 Å^2
• Rotatable Bonds: 2

DETAILS

Toronto Research Chemicals - I780050

A new isoquinoline alkaloid from Litsea cubeba as antibacterial agent.

REFERENCES

• Kimura, I., et al.: Planta Med., 48, 43 (1983)
• Montgomery, C., et al.: J. Nat. Prod., 48, 833 (1983)
• Lin, F., et al.: Chem. Pharm. Bull, 49, 1292 (1983)