(3S,4S,6S)-3,4,5-trihydroxy-6-{2-hydroxy-4-[1-hydroxy-2-(methylamino)ethyl]phenoxy}oxane-2-carboxylic acid

• ChemBase ID: 168087
• Molecular Formular: C15H21NO9
• Molecular Mass: 359.32854
• Monoisotopic Mass: 359.12163126
• SMILES: c1(c(ccc(c1)C(CNC)O)O[C@@H]1OC([C@H]([C@@H](C1O)O)O)C(=O)O)O
• Canonical SMILES: CNCC(c1ccc(c(c1)O)O[C@@H]1OC(C(=O)O)[C@H]([C@@H](C1O)O)O)O
• InChI: InChI=1S/C15H21NO9/c1-16-5-8(18)6-2-3-9(7(17)4-6)24-15-12(21)10(19)11(20)13(25-15)14(22)23/h2-4,8,10-13,15-21H,5H2,1H3,(H,22,23)/t8?,10-,11-,12?,13?,15+/m0/s1
• InChIKey: BLTFFSZSAZRUSC-JGWCBDLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S,6S)-3,4,5-trihydroxy-6-{2-hydroxy-4-[1-hydroxy-2-(methylamino)ethyl]phenoxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (3S,4S,6S)-3,4,5-trihydroxy-6-{2-hydroxy-4-[1-hydroxy-2-(methylamino)ethyl]phenoxy}oxane-2-carboxylic acid
• Synonyms: 2-Hydroxy-4-[1-hydroxy-2-(methylamino)ethyl]phenyl β-D-Glucopyranosiduronic Acid; DL-Epinephrine β-D-Glucuronide

Database IDs

• PubChem SID: 162262219
• PubChem CID: 71316364

CALCULATED PROPERTIES

• Acid pKa: 2.726085
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -4.1258254
• LogD (pH = 7.4): -4.132654
• Log P: -4.125617
• Molar Refractivity: 81.2421 cm^3
• Polarizability: 32.931877 Å^3
• Polar Surface Area: 168.94 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E588590

A metabolite of Epinephrine.

REFERENCES

• Gaudin C., et al.: Life Sci., 37, 1469 (1985)