(1S,5R,13R,17S)-17-hydroxy-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-one

• ChemBase ID: 170369
• Molecular Formular: C18H19NO4
• Molecular Mass: 313.34776
• Monoisotopic Mass: 313.13140809
• SMILES: [C@H]12C(=O)C=C[C@@]3([C@]41c1c(C[C@H]3N(CC4)C)ccc(c1O2)OC)O
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@]4(O)C=CC1=O)C
• InChI: InChI=1S/C18H19NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-6,13,16,21H,7-9H2,1-2H3/t13-,16+,17+,18-/m1/s1
• InChIKey: YYCRAERBSFHMPL-XFKAJCMBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17S)-17-hydroxy-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,15-tetraen-14-one
• IUPAC Traditional name: (1S,5R,13R,17S)-17-hydroxy-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,15-tetraen-14-one
• Synonyms: (5α)-7,8-Didehydro-4,5-epoxy-14-hydroxy-3-methoxy-17-methyl-morphinan-6-one; 7,8-Didehydro-4,5.alpha.-epoxy-14-hydroxy-3-methoxy-17-methyl-morphinan-6-one; 14-Hydroxy Codeinone

Database IDs

• CAS Number: 508-54-3
• PubChem SID: 164226279
• PubChem CID: 9926820

CALCULATED PROPERTIES

• Acid pKa: 13.153089
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -1.3291483
• LogD (pH = 7.4): 0.43997902
• Log P: 1.1885964
• Molar Refractivity: 84.9811 cm^3
• Polarizability: 32.775665 Å^3
• Polar Surface Area: 59.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H922200

An intermediate in the preparation of Oxycodone and other alkaloid based opiate antagonists.

REFERENCES

• Brogle, K., et al.: J. Pharm. Biomed. Anal., 19, 669 (1999)
• Szentesi, A., et al.: Anal. Bioanal. Chem., 374, 427 (1999)
• Lattanzi, R., et al.: J. Med. Chem., 48, 3372 (1999)