(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-10-hydroxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 167769
• Molecular Formular: C22H27NO9
• Molecular Mass: 449.45108
• Monoisotopic Mass: 449.16858145
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@H]4[C@@]3([C@H]([C@H](CC4)O[C@@H]3O[C@H]([C@H]([C@@H]([C@@H]3O)O)O)C(=O)O)O2)CCN1)O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@@H](O[C@H]([C@H]1O)C(=O)O)O[C@H]1CC[C@@H]2[C@@]34[C@H]1Oc1c4c(C[C@H]2NCC3)ccc1O
• InChI: InChI=1S/C22H27NO9/c24-11-3-1-8-7-10-9-2-4-12(19-22(9,5-6-23-10)13(8)17(11)31-19)30-21-16(27)14(25)15(26)18(32-21)20(28)29/h1,3,9-10,12,14-16,18-19,21,23-27H,2,4-7H2,(H,28,29)/t9-,10+,12-,14-,15-,16+,18-,19-,21+,22-/m0/s1
• InChIKey: OEUSICUPLSEHPA-LHWQPMLGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,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-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,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-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (5α,6α)-4,5-Epoxy-3-hydroxymorphinan-6-yl β-D-Glucopyranosiduronic Acid; Dihydronormorphine 6-β-D-Glucuronide; Dihydro Normorphine 6-O-β-D-Glucuronide

Database IDs

• CAS Number: 561323-10-2
• PubChem SID: 162261902
• PubChem CID: 71316219

CALCULATED PROPERTIES

• Acid pKa: 2.9058163
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -2.9029555
• LogD (pH = 7.4): -2.9035919
• Log P: -2.9023714
• Molar Refractivity: 106.1458 cm^3
• Polarizability: 42.77501 Å^3
• Polar Surface Area: 157.94 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D450360

Dihydro Normorphine 6-O-β-D-Glucuronide is a glucuronide derivative of Dihydro Normorphine (D450350).

REFERENCES

• Stachulski, A.V. et al.: Bioorg. Med. Chem. Lett., 13, 1207 (2003)