(2S,3S,4S,5R,6S)-6-{4-[2-amino-1-(1-hydroxycyclohexyl)ethyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 167231
• Molecular Formular: C20H29NO8
• Molecular Mass: 411.44616
• Monoisotopic Mass: 411.18931689
• SMILES: c1cc(ccc1C(C1(CCCCC1)O)CN)O[C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@@H]1O)C(=O)O
• Canonical SMILES: NCC(C1(O)CCCCC1)c1ccc(cc1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C20H29NO8/c21-10-13(20(27)8-2-1-3-9-20)11-4-6-12(7-5-11)28-19-16(24)14(22)15(23)17(29-19)18(25)26/h4-7,13-17,19,22-24,27H,1-3,8-10,21H2,(H,25,26)/t13?,14-,15-,16+,17-,19+/m0/s1
• InChIKey: VNRFTNKWISCOMJ-KUIQUDTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{4-[2-amino-1-(1-hydroxycyclohexyl)ethyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{4-[2-amino-1-(1-hydroxycyclohexyl)ethyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: rac N,N-Didesmethyl-O-desmethyl Venlafaxine Glucuronide

Database IDs

• PubChem SID: 162261364
• PubChem CID: 71316024

CALCULATED PROPERTIES

• Acid pKa: 2.956088
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -2.434429
• LogD (pH = 7.4): -2.43722
• Log P: -2.4338312
• Molar Refractivity: 100.4844 cm^3
• Polarizability: 40.590706 Å^3
• Polar Surface Area: 162.7 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 200-202°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D440975

A metabolite of Venlafaxine.