(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-yl]oxy}oxane-2-carboxylic acid dihydrate

• ChemBase ID: 130918
• Molecular Formular: C23H31NO11
• Molecular Mass: 497.49234
• Monoisotopic Mass: 497.18971082
• SMILES: CN1CC[C@]23c4c5ccc(c4O[C@H]2[C@H](C=C[C@H]3[C@@H]1C5)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C(=O)O)O)O)O)O.O.O
• Canonical SMILES: O[C@@H]1[C@@H](O)[C@@H](O[C@@H]([C@H]1O)C(=O)O)O[C@H]1C=C[C@@H]2[C@@]34[C@H]1Oc1c4c(C[C@@H]2N(CC3)C)ccc1O.O.O
• InChI: InChI=1S/C23H27NO9.2H2O/c1-24-7-6-23-10-3-5-13(31-22-17(28)15(26)16(27)19(33-22)21(29)30)20(23)32-18-12(25)4-2-9(14(18)23)8-11(10)24;;/h2-5,10-11,13,15-17,19-20,22,25-28H,6-8H2,1H3,(H,29,30);2*1H2/t10-,11+,13-,15-,16-,17+,19-,20-,22+,23-;;/m0../s1
• InChIKey: NRBQUVXMCUQJPZ-WFLHAITMSA-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-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,15-tetraen-14-yl]oxy}oxane-2-carboxylic acid dihydrate
• IUPAC Traditional name: morphine-6-glucuronide dihydrate
• Synonyms: M6G; Morphine 6-β-D-glucuronide hydrate

Database IDs

• CAS Number: 20290-10-2
• MDL Number: MFCD00167238
• PubChem SID: 162225196; 24896850
• PubChem CID: 71308353

CALCULATED PROPERTIES

• Acid pKa: 2.874723
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -2.9851973
• LogD (pH = 7.4): -2.9913528
• Log P: -2.9848087
• Molar Refractivity: 112.4031 cm^3
• Polarizability: 44.34656 Å^3
• Polar Surface Area: 149.15 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: LZ6500700
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-43
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H317-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Drug Control: USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC)

DETAILS

Sigma Aldrich - M3528

Biochem/physiol Actions
Major metabolite of morphine that is a potent μ-opioid receptor agonist.