(1R,9R,10S)-3,10-dihydroxy-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-13-one

• ChemBase ID: 170475
• Molecular Formular: C18H23NO4
• Molecular Mass: 317.37952
• Monoisotopic Mass: 317.16270822
• SMILES: c1(c(c2c(cc1)C[C@@H]1[C@]3([C@@]2(CC(=O)CC3)CCN1C)O)O)OC
• Canonical SMILES: COc1ccc2c(c1O)[C@@]13CCN([C@H](C2)[C@]3(O)CCC(=O)C1)C
• InChI: InChI=1S/C18H23NO4/c1-19-8-7-17-10-12(20)5-6-18(17,22)14(19)9-11-3-4-13(23-2)16(21)15(11)17/h3-4,14,21-22H,5-10H2,1-2H3/t14-,17-,18-/m1/s1
• InChIKey: MCSOAHVAIJXNDN-ZTFGCOKTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9R,10S)-3,10-dihydroxy-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-13-one
• IUPAC Traditional name: (1R,9R,10S)-3,10-dihydroxy-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-13-one
• Synonyms: 4,14-Dihydroxy-3-methoxy-N-methyl-6-oxo-morphinan; 14-Hydroxydihydrothebainone; 4,14-Dihydroxy-3-methoxy-17-methyl-morphinan-6-one; 14-Hydroxydihydro Thebainone

Database IDs

• CAS Number: 6199-38-8
• PubChem SID: 164226385
• PubChem CID: 5492895

CALCULATED PROPERTIES

• Acid pKa: 9.788745
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.5369192
• LogD (pH = 7.4): 0.23510407
• Log P: 0.9559409
• Molar Refractivity: 86.4826 cm^3
• Polarizability: 33.672897 Å^3
• Polar Surface Area: 70.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - H941390

Intermediate in the preparation of morphine alkaloids.

REFERENCES

• Nemoto, T., et al.: Bioorg. Med. Chem., 16, 4304 (2008)
• Li, F., et al.: Chem. Biol. Drug Des., 74, 335 (2008)