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

• ChemBase ID: 175702
• Molecular Formular: C16H17NO4
• Molecular Mass: 287.31048
• Monoisotopic Mass: 287.11575803
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H](C(=O)CC4)O2)CCN1)O)O
• Canonical SMILES: O=C1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2NCC3)ccc1O)O
• InChI: InChI=1S/C16H17NO4/c18-9-2-1-8-7-11-16(20)4-3-10(19)14-15(16,5-6-17-11)12(8)13(9)21-14/h1-2,11,14,17-18,20H,3-7H2/t11-,14+,15+,16-/m1/s1
• InChIKey: HLMSIZPQBSYUNL-IPOQPSJVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17S)-10,17-dihydroxy-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,5R,13R,17S)-10,17-dihydroxy-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-morphinan-6-one; 7,8-Dihydro-14-hydroxy- normorphinone; 4-Hydroxydihydronormorphinone; EN 3169; 7,8-Dihydro-14-hydroxynormorphinone; Nor Oxymorphone

Database IDs

• CAS Number: 33522-95-1
• PubChem SID: 164231612
• PubChem CID: 5497189

CALCULATED PROPERTIES

• Acid pKa: 10.1861725
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.6624272
• LogD (pH = 7.4): -1.5449784
• Log P: 0.120955616
• Molar Refractivity: 74.2648 cm^3
• Polarizability: 29.281761 Å^3
• Polar Surface Area: 78.79 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (sparingly)
• Apperance: Off-White to Light Brown Solid
• Melting Point: >265°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - N825300

A metabolite of Naloxone and Naltrexone.

REFERENCES

• Cone, E., et al.: Drug Metab. Dispos., 6, 488 (1978)
• Leow, K., et al.: Ther. Drug Monit., 14, 479 (1978)
• Kassahun, K., et al.: Drug Metab. Dispos., 25, 81 (1978)