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

• ChemBase ID: 167732
• Molecular Formular: C18H23NO3
• Molecular Mass: 301.38012
• Monoisotopic Mass: 301.1677936
• SMILES: c1(c(c2c(cc1)C[C@@H]1[C@H]3[C@@]2(CC(=O)CC3)CCN1C)O)OC
• Canonical SMILES: COc1ccc2c(c1O)[C@@]13CCN([C@H](C2)[C@@H]3CCC(=O)C1)C
• InChI: InChI=1S/C18H23NO3/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,4-5,7-10H2,1-2H3/t13-,14+,18-/m0/s1
• InChIKey: CDGFTOARGCEWKI-IYOUNJFTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,9R,10R)-3-hydroxy-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: (1S,9R,10R)-3-hydroxy-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: 1,9,10,10a-Tetrahydro-5-hydroxy-6-methoxy-11-methyl-2H-10,4a-iminoethanophenanthren-3(4H)-one; 4-Hydroxy-3-methoxy-17-methyl-morphinan-6-one; 7,8-Dihydrothebainone; 7,8-Dihydrothebainone A; Dihydrothebainone; Dihydrothebainone A; NSC 134598; NSC 35545; (-)-Dihydrothebainone

Database IDs

• CAS Number: 847-86-9
• PubChem SID: 162261865
• PubChem CID: 5355412

CALCULATED PROPERTIES

• Acid pKa: 9.863936
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.9257409
• LogD (pH = 7.4): 0.80663604
• Log P: 1.7879466
• Molar Refractivity: 85.1855 cm^3
• Polarizability: 33.039627 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Pink Solid

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D449820

Morphinan derivative. Used in the preparation of ABC drug transporter inhibitors.