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

• ChemBase ID: 166616
• Molecular Formular: C22H33NO8
• Molecular Mass: 439.49932
• Monoisotopic Mass: 439.22061702
• SMILES: c1cc(ccc1C(C1(CCCCC1)O)CN(C)C)O[C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@@H]1O)C(=O)O
• Canonical SMILES: CN(CC(C1(O)CCCCC1)c1ccc(cc1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C22H33NO8/c1-23(2)12-15(22(29)10-4-3-5-11-22)13-6-8-14(9-7-13)30-21-18(26)16(24)17(25)19(31-21)20(27)28/h6-9,15-19,21,24-26,29H,3-5,10-12H2,1-2H3,(H,27,28)/t15?,16-,17-,18+,19-,21+/m0/s1
• InChIKey: GRDOISGIGBUYGA-NMXLZWJASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol Glucuronide; 4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenylβ-D-Glucopyranosiduronic Acid; rac O-Desmethyl Venlafaxine β-D-Glucuronide

Database IDs

• CAS Number: 1021933-98-1
• PubChem SID: 162260749
• PubChem CID: 71315801

CALCULATED PROPERTIES

• Acid pKa: 2.955853
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -2.0869334
• LogD (pH = 7.4): -2.0972083
• Log P: -2.0865471
• Molar Refractivity: 110.5537 cm^3
• Polarizability: 44.24603 Å^3
• Polar Surface Area: 139.92 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: >190°C (dec.)

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D296525

A metabolite of Venlafaxine, a selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant.

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)