(9S)-3,16-dihydroxy-4,15-dimethoxy-10,10-dimethyl-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,13,15-hexaen-10-ium iodide

• ChemBase ID: 164977
• Molecular Formular: C20H24INO4
• Molecular Mass: 469.31333
• Monoisotopic Mass: 469.07500625
• SMILES: c1(ccc2c(c1O)c1c3[C@H](C2)[N+](CCc3cc(c1O)OC)(C)C)OC.[I-]
• Canonical SMILES: COc1ccc2c(c1O)c1c(O)c(OC)cc3c1[C@H](C2)[N+](C)(C)CC3.[I-]
• InChI: InChI=1S/C20H23NO4.HI/c1-21(2)8-7-12-10-15(25-4)20(23)18-16(12)13(21)9-11-5-6-14(24-3)19(22)17(11)18;/h5-6,10,13H,7-9H2,1-4H3,(H-,22,23);1H/t13-;/m0./s1
• InChIKey: ODRHNGNRVVELAJ-ZOWNYOTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9S)-3,16-dihydroxy-4,15-dimethoxy-10,10-dimethyl-10-azatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadeca-1(17),2,4,6,13,15-hexaen-10-ium iodide
• IUPAC Traditional name: (9S)-3,16-dihydroxy-4,15-dimethoxy-10,10-dimethyl-10-azatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadeca-1(17),2,4,6,13,15-hexaen-10-ium iodide
• Synonyms: (6aS)-5,6,6a,7-Tetrahydro-1,11-dihydroxy-2,10-dimethoxy-6,6-dimethyl-4H-dibenzo[de,g]quinolinium Iodide; 1,11-Dihydroxy-2,10-dimethoxy-6-methyl-6aα-aporphinium Iodide; Magnoflorine Iodide (6CI,7CI); (+)-Magnoflorine Iodide; Escholine Iodide; NSC 150447; Thalictrine Iodide; Corytuberine Methiodide

Database IDs

• CAS Number: 4277-43-4
• PubChem SID: 162259111
• PubChem CID: 6451920

CALCULATED PROPERTIES

• Acid pKa: 9.111512
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.3686291
• LogD (pH = 7.4): -0.8156884
• Log P: -1.3833978
• Molar Refractivity: 108.8281 cm^3
• Polarizability: 38.408386 Å^3
• Polar Surface Area: 58.92 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Product Information

• Salt Data: I-
• Classification: Genuine Natural Compounds

DETAILS

Toronto Research Chemicals - C697520

A minor alkaloid from Stylophorum diphyllum as antimicrobial and antitumor agent.

REFERENCES

• Green, J., et al.: J. Pharm. Sci., 69, 936 (1980)
• Wu, W., et al.: J. Nat. Prod., 43, 567 (1980)
• Liu, Z., et al.: J. Pharm. Pharmacol., 55, 1531 (1980)