(1S,5S,13R,17R)-10-hydroxy-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: 174816
• Molecular Formular: C17H17NO3
• Molecular Mass: 283.32178
• Monoisotopic Mass: 283.12084341
• SMILES: c1(c2c3c(cc1)C[C@H]1[C@H]4[C@@]3([C@H](C(=O)C=C4)O2)CCN1C)O
• Canonical SMILES: O=C1C=C[C@@H]2[C@@]34[C@H]1Oc1c4c(C[C@@H]2N(CC3)C)ccc1O
• InChI: InChI=1S/C17H17NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,16,19H,6-8H2,1H3/t10-,11-,16-,17-/m0/s1
• InChIKey: PFBSOANQDDTNGJ-BHWMQLMCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S,13R,17R)-10-hydroxy-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,5S,13R,17R)-10-hydroxy-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-3-hydroxy-17-methylmorphinan-6-one; Morphinone

Database IDs

• CAS Number: 467-02-7
• PubChem SID: 164230726
• PubChem CID: 98518

CALCULATED PROPERTIES

• Acid pKa: 10.097182
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.0521158
• LogD (pH = 7.4): 0.69976026
• Log P: 1.6570323
• Molar Refractivity: 79.3557 cm^3
• Polarizability: 30.230232 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Light Yellow Solid
• Melting Point: 148-150°C

Safety Information

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

DETAILS

Toronto Research Chemicals - M652350

A toxic metabolite of Morphine.Controlled substance.

REFERENCES

• James, R., et al.: J. Pharmacol. Exp. Ther., 221, 708 (1982)
• Yamano, S., et al.: J. Biol. Chem., 260, 5259(1982)
• Ishida, T., et al.: Drug Metab. Dispos., 17, 77 (1982)
• Yamano, S., et al.: Xenobiotica, 27, 645 (1982)