(1S,9S)-3-hydroxy-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one

• ChemBase ID: 178492
• Molecular Formular: C18H21NO3
• Molecular Mass: 299.36424
• Monoisotopic Mass: 299.15214354
• SMILES: c1(c(c2c(cc1)C[C@H]1C3[C@@]2(CC(=O)C=C3)CCN1C)O)OC
• Canonical SMILES: COc1ccc2c(c1O)[C@@]13CCN([C@@H](C2)C3C=CC(=O)C1)C
• InChI: InChI=1S/C18H21NO3/c1-19-8-7-18-10-12(20)4-5-13(18)14(19)9-11-3-6-15(22-2)17(21)16(11)18/h3-6,13-14,21H,7-10H2,1-2H3/t13?,14-,18-/m0/s1
• InChIKey: SLJDAVMWFVYEFI-NOBWMKPMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,9S)-3-hydroxy-4-methoxy-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: (1S,9S)-3-hydroxy-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5,11-tetraen-13-one
• Synonyms: 7,8-Didehydro-4-hydroxy-3-methoxy-17-methylmorphinan-6-one; Thebainone A; Thebainone

Database IDs

• CAS Number: 467-98-1
• PubChem SID: 164234402
• PubChem CID: 71752501

CALCULATED PROPERTIES

• Acid pKa: 9.845709
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.82531446
• LogD (pH = 7.4): 0.9297009
• Log P: 1.822452
• Molar Refractivity: 86.2788 cm^3
• Polarizability: 32.797363 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Beige to Brown Solid
• Melting Point: >128°C (dec.)

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

Toronto Research Chemicals - T342500

A new metabolite of Thebaine.Controlled substance.

REFERENCES

• Mikus, G., et al.: Xenobiotica, 21, 1501 (1991)
• French, C., et al.: Biochem. J., 312, 671 (1991)
• Lenz, R., et al.: J. Biol. Chem., 270, 31091 (1991)