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

• ChemBase ID: 175668
• Molecular Formular: C16H17NO3
• Molecular Mass: 271.31108
• Monoisotopic Mass: 271.12084341
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@H]4[C@@]3([C@H](C(=O)CC4)O2)CCN1)O
• Canonical SMILES: O=C1CC[C@@H]2[C@@]34[C@H]1Oc1c4c(C[C@H]2NCC3)ccc1O
• InChI: InChI=1S/C16H17NO3/c18-11-3-1-8-7-10-9-2-4-12(19)15-16(9,5-6-17-10)13(8)14(11)20-15/h1,3,9-10,15,17-18H,2,4-7H2/t9-,10+,15-,16-/m0/s1
• InChIKey: SWIRXSKBBSJXGY-UIHHKEIPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17R)-10-hydroxy-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,17R)-10-hydroxy-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-hydroxymorphinan-6-one; 4,5α-Epoxy-3-hydroxymorphinan-6-one; N-Demethylhydromorphone; Nordihydromorphone; Norhydromorphone; Nor Hydromorphone

Database IDs

• CAS Number: 14696-23-2
• PubChem SID: 164231578
• PubChem CID: 10355824

CALCULATED PROPERTIES

• Acid pKa: 9.71578
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.7881651
• LogD (pH = 7.4): -1.0944352
• Log P: 0.8542291
• Molar Refractivity: 72.9677 cm^3
• Polarizability: 28.635921 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N705750

Norhydromorphone is a novel metabolite of Hydromorphone (H714650).

REFERENCES

• Cone, E., et al.: J. Pharmaceut. Sci., 66, 1709 (1977)
• Konishi, M., et al.: Xenobiotica, 24, 591 (1977)
• Vaccarino, A., et al.: Brain Res., 666, 104 (1977)
• Bartlett, S., et al.: Life Sci., 57, 609 (1977)