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

• ChemBase ID: 176142
• Molecular Formular: C17H19NO4
• Molecular Mass: 301.33706
• Monoisotopic Mass: 301.13140809
• SMILES: c1(c2c3c(cc1)C[C@H]1[C@]4([C@@]3([C@H](C(=O)CC4)O2)CCN1C)O)O
• Canonical SMILES: O=C1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@@H]2N(CC3)C)ccc1O)O
• InChI: InChI=1S/C17H19NO4/c1-18-7-6-16-13-9-2-3-10(19)14(13)22-15(16)11(20)4-5-17(16,21)12(18)8-9/h2-3,12,15,19,21H,4-8H2,1H3/t12-,15-,16-,17+/m0/s1
• InChIKey: UQCNKQCJZOAFTQ-OSMBCOQSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S,13R,17S)-10,17-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-trien-14-one
• IUPAC Traditional name: (1S,5S,13R,17S)-10,17-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-trien-14-one
• Synonyms: (5α)-4,5-Epoxy-3,14-dihydroxy-17-methyl-morphinan-6-one; 7,8-Dihydro-14-hydroxymorphinone; Dihydroxymorphinone; NIH 10323; NSC 19045; Oxymorphone

Database IDs

• CAS Number: 76-41-5
• PubChem SID: 164232052
• PubChem CID: 9646

CALCULATED PROPERTIES

• Acid pKa: 10.07158
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.7639712
• LogD (pH = 7.4): 0.008845229
• Log P: 0.78487325
• Molar Refractivity: 79.5595 cm^3
• Polarizability: 31.115646 Å^3
• Polar Surface Area: 70.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone (hot); Chloroform
• Apperance: Crystalline Solid
• Melting Point: >205°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - O876800

Controlled substance (opiate). Analgesic (narcotic).

REFERENCES

• Ananthan, S., et al.: J. Med. Chem., 47, 1400 (2004)
• Gimbel, J., et al.: Anesth. Analg., 99, 1472 (2004)
• Adams, M., et al.: J. Clin. Pharmacol., 45, 337 (2004)