(1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5,11-tetraen-13-one

• ChemBase ID: 72984
• Molecular Formular: C19H23NO4
• Molecular Mass: 329.39022
• Monoisotopic Mass: 329.16270822
• SMILES: c1(c(c2c(cc1)C[C@H]1[C@@H]3[C@]2(CC(=O)C(=C3)OC)CCN1C)O)OC
• Canonical SMILES: COC1=C[C@@H]2[C@@H]3Cc4c([C@@]2(CC1=O)CCN3C)c(O)c(cc4)OC
• InChI: InChI=1S/C19H23NO4/c1-20-7-6-19-10-14(21)16(24-3)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9,12-13,22H,6-8,10H2,1-3H3/t12-,13+,19-/m1/s1
• InChIKey: INYYVPJSBIVGPH-QHRIQVFBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5,11-tetraen-13-one; (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5,11-tetraen-13-one
• IUPAC Traditional name: sinomenine
• Synonyms: Cucoline; Kukoline; Coculine; Sabianine A; Sinomenine

Database IDs

• CAS Number: 115-53-7
• PubChem SID: 162037904
• PubChem CID: 5459308

CALCULATED PROPERTIES

• Acid pKa: 9.832212
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -1.1205362
• LogD (pH = 7.4): 0.6472067
• Log P: 1.4476779
• Molar Refractivity: 92.9974 cm^3
• Polarizability: 35.338394 Å^3
• Polar Surface Area: 59.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: CHCl3; Free Base
• Classification: Rare Genuine Natural Compounds

DETAILS

Selleck Chemicals - S2359

Research Area: Immunology , Inflammation
Biological Activity:
Sinomenine(Cucoline) is traditionally used in herbal medicine in these countries, as a treatment for rheumatism and arthritis. However its analgesic action against other kinds of pain is limited. Sinomenine is a morphinan derivative, related to opioids such as levorphanol and the non-opioid cough suppressant dextromethorphan. Its anti-rheumatic effects are thought to be primarily mediated via release of histamine, but other effects such as inhibition of prostaglandin, leukotriene and nitric oxide synthesis may also be involved. [1]

REFERENCES

• http://en.wikipedia.org/wiki/Sinomenine