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

• ChemBase ID: 167768
• 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)O2)CCN1)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@@H](O[C@H]([C@H]1O)C(=O)O)Oc1ccc2c3c1O[C@@H]1[C@@]43CCN[C@H](C2)[C@@H]4CC[C@@H]1O
• InChI: InChI=1S/C22H27NO9/c24-11-3-2-9-10-7-8-1-4-12(17-13(8)22(9,5-6-23-10)19(11)31-17)30-21-16(27)14(25)15(26)18(32-21)20(28)29/h1,4,9-11,14-16,18-19,21,23-27H,2-3,5-7H2,(H,28,29)/t9-,10+,11-,14-,15-,16+,18-,19-,21+,22-/m0/s1
• InChIKey: LHSVWZWNZALPMV-DYMQYMLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-14-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-10-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-14-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-10-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (5α,6α)-4,5-Epoxy-6-hydroxymorphinan-3-yl β-D-Glucopyranosiduronic Acid; Dihydronormorphine 3-β-D-Glucuronide; Dihydro Normorphine 3-O-β-D-Glucuronide

Database IDs

• CAS Number: 491847-30-4
• PubChem SID: 162261901
• PubChem CID: 71316218

CALCULATED PROPERTIES

• Acid pKa: 2.6758034
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -3.3998039
• LogD (pH = 7.4): -3.3999598
• Log P: -3.3994536
• Molar Refractivity: 105.8769 cm^3
• Polarizability: 42.772564 Å^3
• Polar Surface Area: 157.94 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D450355

Dihydro Normorphine 3-O-β-D-Glucuronide is a glucuronide derivative of Dihydro Normorphine (D450350).