2-[(1S,2R,6S,14R,15R,16R)-11,15-dimethoxy-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11-trien-16-yl]-3,3-dimethylbutan-2-ol

• ChemBase ID: 174115
• Molecular Formular: C26H37NO4
• Molecular Mass: 427.57628
• Monoisotopic Mass: 427.27225867
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]45[C@@]3([C@H]([C@]([C@H](C4)C(C(C)(C)C)(C)O)(CC5)OC)O2)CCN1)OC
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@@]43CCN[C@H](C2)[C@@]24CC[C@@]1(OC)[C@H](C2)C(C(C)(C)C)(O)C
• InChI: InChI=1S/C26H37NO4/c1-22(2,3)23(4,28)17-14-24-9-10-26(17,30-6)21-25(24)11-12-27-18(24)13-15-7-8-16(29-5)20(31-21)19(15)25/h7-8,17-18,21,27-28H,9-14H2,1-6H3/t17-,18-,21-,23?,24-,25+,26-/m1/s1
• InChIKey: GUFHEIAUPRGDNQ-ALONWEKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2R,6S,14R,15R,16R)-11,15-dimethoxy-13-oxa-3-azahexacyclo[13.2.2.1^2,^8.0^1,^6.0^6,^1^4.0^7,^1^2]icosa-7,9,11-trien-16-yl]-3,3-dimethylbutan-2-ol
• IUPAC Traditional name: 2-[(1S,2R,6S,14R,15R,16R)-11,15-dimethoxy-13-oxa-3-azahexacyclo[13.2.2.1^2,^8.0^1,^6.0^6,^1^4.0^7,^1^2]icosa-7,9,11-trien-16-yl]-3,3-dimethylbutan-2-ol
• Synonyms: 17-Demethyl-7α-(1-hydroxy-1,2,2-trimethylpropyl)-6,14-endo-ethanotetrahydrothebaine; 3-O-Methyl Norbuprenorphine

Database IDs

• CAS Number: 16614-59-8
• PubChem SID: 164230025
• PubChem CID: 46193340

CALCULATED PROPERTIES

• Acid pKa: 14.297996
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.20929752
• LogD (pH = 7.4): 0.4183799
• Log P: 3.014348
• Molar Refractivity: 119.0079 cm^3
• Polarizability: 47.547874 Å^3
• Polar Surface Area: 59.95 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M325685

Intermediate in the preparation of Morphinan analogs.

REFERENCES

• Abel, A., et al.: Biotechnol. Lett., 24, 1741 (2002)
• Abel, A., et al.: Enz. Microb. Technol., 33, 743 (2002)