(1S,5R,13R,14S,17R)-10,14-dihydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-6-one

• ChemBase ID: 176088
• Molecular Formular: C17H17NO4
• Molecular Mass: 299.32118
• Monoisotopic Mass: 299.11575803
• SMILES: c1(c2c3c(cc1)C(=O)[C@H]1[C@H]4[C@@]3([C@H]([C@H](C=C4)O)O2)CCN1C)O
• Canonical SMILES: O[C@H]1C=C[C@@H]2[C@@]34[C@H]1Oc1c4c(C(=O)[C@@H]2N(CC3)C)ccc1O
• InChI: InChI=1S/C17H17NO4/c1-18-7-6-17-9-3-5-11(20)16(17)22-15-10(19)4-2-8(12(15)17)14(21)13(9)18/h2-5,9,11,13,16,19-20H,6-7H2,1H3/t9-,11-,13+,16-,17-/m0/s1
• InChIKey: HNJBQZPKNKFLFM-KWEAMAEZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14S,17R)-10,14-dihydroxy-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-6-one
• IUPAC Traditional name: (1S,5R,13R,14S,17R)-10,14-dihydroxy-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-6-one
• Synonyms: (5α,6α)-7,8-Didehydro-4,5-epoxy-3,6-dihydroxy-17-methylmorphinan-10-one; 10-Oxomorphine; ZINC 22065588; 10-Oxo Morphine

Database IDs

• CAS Number: 68254-48-8
• PubChem SID: 164231998
• PubChem CID: 155023

CALCULATED PROPERTIES

• Acid pKa: 8.186117
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.2697564
• LogD (pH = 7.4): 0.20774995
• Log P: 0.21986207
• Molar Refractivity: 80.7316 cm^3
• Polarizability: 30.925102 Å^3
• Polar Surface Area: 70.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO (Sparingly); Methanol (Sparingly)
• Apperance: Brown Solid
• Melting Point: >200°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - O870010

10-Oxo Morphine is a decomposition product of Morphine (M652290). Morphine impurity. Controlled substance.

REFERENCES

• Proksa, B., et al.: Pharmazie, 39, 687 (1984)
• Farsam, H., et al.: Pharm. Res., 7, 1205 (1984)
• Shalaev, E., et al.: Pharm. Res.,17, 366 ( 2000), Kelly, S.S., et al.: J. Pharm. Sci., 92, 485 (1984)