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

• ChemBase ID: 176140
• Molecular Formular: C17H21NO4
• Molecular Mass: 303.35294
• Monoisotopic Mass: 303.14705816
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H]([C@@H](CC4)O)O2)CCN1C)O)O
• Canonical SMILES: O[C@@H]1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1O)O
• InChI: InChI=1S/C17H21NO4/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/h2-3,11-12,15,19-21H,4-8H2,1H3/t11-,12-,15+,16+,17-/m1/s1
• InChIKey: AABLHGPVOULICI-LQPBRMSDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14R,17S)-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-triene-10,14,17-triol
• IUPAC Traditional name: (1S,5R,13R,14R,17S)-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-triene-10,14,17-triol
• Synonyms: (5α,6β)-4,5-Epoxy-17-methylmorphinan-3,6,14-triol; 14-Dihydroxy-6-deoxy-7,8-dihydro-6β-morphine; 14-Hydroxy-7,8-dihydroisomorphine; 14-Hydroxydihydroisomorphine; 6β-Oxymorphol

Database IDs

• CAS Number: 54934-75-7
• PubChem SID: 164232050
• PubChem CID: 21779240

CALCULATED PROPERTIES

• Acid pKa: 10.166495
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.6846979
• LogD (pH = 7.4): -1.059676
• Log P: 0.19665293
• Molar Refractivity: 80.4569 cm^3
• Polarizability: 31.582043 Å^3
• Polar Surface Area: 73.16 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - O876755

A metabolite of Oxymorphone.

REFERENCES

• Caraco, Y., et al.: Drug Metab. Dispos., 24, 761 (1996)
• Metzger, T., et al.: J. Med. Chem., 44, 857 (1996)
• Clark, D., et al.: Drug Discov. Today, 8, 927 (1996)
• Lalovic, B., et al.: Drug Metab. Dispos., 32, 447 (1996)