(2S,3S,4S,5R,6R)-6-[(1R)-1-(3-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}phenyl)-2-(methylamino)ethoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 176547
• Molecular Formular: C21H29NO14
• Molecular Mass: 519.45326
• Monoisotopic Mass: 519.15880461
• SMILES: c1c(cccc1[C@H](CNC)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: CNC[C@@H](c1cccc(c1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H29NO14/c1-22-6-9(34-21-15(28)11(24)13(26)17(36-21)19(31)32)7-3-2-4-8(5-7)33-20-14(27)10(23)12(25)16(35-20)18(29)30/h2-5,9-17,20-28H,6H2,1H3,(H,29,30)(H,31,32)/t9-,10-,11-,12-,13-,14+,15+,16-,17-,20+,21+/m0/s1
• InChIKey: VDQQBBUYOKHAOY-GYSDEIIGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-[(1R)-1-(3-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}phenyl)-2-(methylamino)ethoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-[(1R)-1-(3-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}phenyl)-2-(methylamino)ethoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: Phenylephrine 2-O-3'-O-Diglucuronide

Database IDs

• PubChem SID: 164232457
• PubChem CID: 71751610

CALCULATED PROPERTIES

• Acid pKa: 2.6675127
• H Acceptors: 15
• H Donor: 9
• LogD (pH = 5.5): -7.460142
• LogD (pH = 7.4): -8.704464
• Log P: -5.53413
• Molar Refractivity: 111.5419 cm^3
• Polarizability: 46.05047 Å^3
• Polar Surface Area: 244.93 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Off-White Solid
• Melting Point: >189°C (dec.)

DETAILS

Toronto Research Chemicals - P320645

Metabolite of Phenylephrine (P320635).