(9S)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2(7),3,5,13,15-hexaene

• ChemBase ID: 112389
• Molecular Formular: C21H25NO4
• Molecular Mass: 355.4275
• Monoisotopic Mass: 355.17835829
• SMILES: CN1CCc2cc(c(c3c2[C@@H]1Cc1c3cc(c(c1)OC)OC)OC)OC
• Canonical SMILES: COc1cc2c(cc1OC)C[C@H]1c3c2c(OC)c(OC)cc3CCN1C
• InChI: InChI=1S/C21H25NO4/c1-22-7-6-12-9-18(25-4)21(26-5)20-14-11-17(24-3)16(23-2)10-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3/t15-/m0/s1
• InChIKey: RUZIUYOSRDWYQF-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9S)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2(7),3,5,13,15-hexaene; (9S)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadeca-1(17),2(7),3,5,13,15-hexaene; (9S)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadeca-1(17),2,4,6,13,15-hexaene
• IUPAC Traditional name: glaucine; (9S)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadeca-1(17),2,4,6,13,15-hexaene
• Synonyms: GLAUCINE; 1,2,9,10-Tetramethoxyaporphine; Glaucine; (S)-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline

Database IDs

• CAS Number: 475-81-0
• EC Number: 207-501-5
• PubChem SID: 162097337
• PubChem CID: 16754

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 1.4678636
• LogD (pH = 7.4): 2.8952234
• Log P: 3.0707269
• Molar Refractivity: 101.8791 cm^3
• Polarizability: 40.46764 Å^3
• Polar Surface Area: 40.16 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder
• Melting Point: 118°C

Safety Information

• RTECS: CE0925000
• European Hazard Symbols: Harmful (Xn)
• Risk Statements: R:22
• Safety Statements: S:36/37/39

Pharmacology Properties

• Mechanism of Action: PDE4 inhibitor

Product Information

• Purity: 98.5
• Biological Source: Alkaloid from a wide variety of genera in the Annonaceae ( Alphonsea, Annona, Polyalthia, Schefferomitra, Uvaria ), Berberidaceae ( Berberis, Mahonia ), Euphorbiaceae ( Croton ), Fumariaceae ( Corydalis, Dicentra ), Lauraceae ( Beilschmiedia, Ocotea, Litsea ), Magnoliaceae ( Liriodendron, Magnolia ), Menispermaceae ( Chasmanthera ), Papaveraceae ( Glaucium, Papaver ), Ranunculaceae ( Thalictrum, Aconitum ), Rhamnaceae ( Colubrina ) and Monimiaceae ( Hedycaria )
• Application(s): Antifungal agent; Antitussive agent with similar potency to Codeine.; Shows antithrombotic, analgesic and antiinflammatory activity

DETAILS

MP Biomedicals - 05223708

MP Biomedicals Rare Chemical collection

InterBioScreen - BB_NC-0833

GNC

REFERENCES

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