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

• ChemBase ID: 167260
• Molecular Formular: C21H32ClNO8
• Molecular Mass: 461.93368
• Monoisotopic Mass: 461.18164467
• SMILES: c1cc(ccc1C(C1(CCCCC1)O)CNC)O[C@@H]1O[C@H]([C@H]([C@H](O)[C@@H]1O)O)C(=O)O.Cl
• Canonical SMILES: CNCC(C1(O)CCCCC1)c1ccc(cc1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O.Cl
• InChI: InChI=1S/C21H31NO8.ClH/c1-22-11-14(21(28)9-3-2-4-10-21)12-5-7-13(8-6-12)29-20-17(25)15(23)16(24)18(30-20)19(26)27;/h5-8,14-18,20,22-25,28H,2-4,9-11H2,1H3,(H,26,27);1H/t14?,15-,16-,17+,18-,20+;/m0./s1
• InChIKey: KXBUKYNISZGJHO-MSULPLJGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[1-(1-hydroxycyclohexyl)-2-(methylamino)ethyl]phenoxy}oxane-2-carboxylic acid hydrochloride
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[1-(1-hydroxycyclohexyl)-2-(methylamino)ethyl]phenoxy}oxane-2-carboxylic acid hydrochloride
• Synonyms: 4-[1-(1-Hydroxycyclohexyl)-2-(methylamino)ethyl]phenyl β-D-Glucopyranosiduronic Acid Hydrochloride; rac N,O-Didesmethyl Venlafaxine β-D-Glucuronide Hydrochloride

Database IDs

• CAS Number: 1021933-99-2
• PubChem SID: 162261393
• PubChem CID: 71316035

CALCULATED PROPERTIES

• Acid pKa: 2.9559805
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -2.2107325
• LogD (pH = 7.4): -2.2113812
• Log P: -2.2100754
• Molar Refractivity: 105.259 cm^3
• Polarizability: 42.417686 Å^3
• Polar Surface Area: 148.71 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: >180°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - D441585

A metabolite of Venlafaxine, a selective serotonin noradrenaline reuptake inhibitor.

REFERENCES

• Kelsey, J., et al.: J. Clin. Psychopharmacol., 16, 21 (1996)
• Long, C., et al.: J. Anal. Toxicol., 21, 166 (1996)
• Deecher, D., et al.: J. Pharmacol. Exp. Ther., 318, 657 (2006)