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

• ChemBase ID: 170942
• Molecular Formular: C17H21NO3
• Molecular Mass: 287.35354
• Monoisotopic Mass: 287.15214354
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@H]4[C@@]3([C@H]([C@@H](CC4)O)O2)CCN1C)O
• Canonical SMILES: O[C@@H]1CC[C@@H]2[C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1O
• InChI: InChI=1S/C17H21NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,13,16,19-20H,3,5-8H2,1H3/t10-,11+,13+,16-,17-/m0/s1
• InChIKey: IJVCSMSMFSCRME-NOSXKOESSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14R,17R)-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-diol
• IUPAC Traditional name: (1S,5R,13R,14R,17R)-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-diol
• Synonyms: (5α,6β)-4,5-Epoxy-17-methyl-morphinan-3,6-diol; Dihydro-α-isomorphine; Dihydroisomorphine; 6β-Hydromorphol

Database IDs

• CAS Number: 26626-12-0
• PubChem SID: 164226852
• PubChem CID: 9814448

CALCULATED PROPERTIES

• Acid pKa: 10.288932
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.9329233
• LogD (pH = 7.4): -0.52666694
• Log P: 1.0786494
• Molar Refractivity: 79.1598 cm^3
• Polarizability: 30.942667 Å^3
• Polar Surface Area: 52.93 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H948470

6β-Hydromorphol is a metabolite of Hydromorphone (H714650).

REFERENCES

• Zheng, M., et al.: Xenobiotica, 32, 427 (2002)
• Zheng, M., et al.: Life Sci., 75, 3129 (2002)