(2S,3S)-2,3-bis(4-methylbenzoyloxy)butanedioic acid; 1-[(1R)-2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol

• ChemBase ID: 179479
• Molecular Formular: C37H45NO10
• Molecular Mass: 663.7539
• Monoisotopic Mass: 663.30434665
• SMILES: c1cc(ccc1[C@@H](C1(CCCCC1)O)CN(C)C)OC.OC(=O)[C@H]([C@@H](C(=O)O)OC(=O)c1ccc(cc1)C)OC(=O)c1ccc(cc1)C
• Canonical SMILES: OC(=O)[C@H]([C@@H](C(=O)O)OC(=O)c1ccc(cc1)C)OC(=O)c1ccc(cc1)C.COc1ccc(cc1)[C@@H](C1(O)CCCCC1)CN(C)C
• InChI: InChI=1S/C20H18O8.C17H27NO2/c1-11-3-7-13(8-4-11)19(25)27-15(17(21)22)16(18(23)24)28-20(26)14-9-5-12(2)6-10-14;1-18(2)13-16(17(19)11-5-4-6-12-17)14-7-9-15(20-3)10-8-14/h3-10,15-16H,1-2H3,(H,21,22)(H,23,24);7-10,16,19H,4-6,11-13H2,1-3H3/t15-,16-;16-/m00/s1
• InChIKey: JFYLKWUYWDBONP-VNMAQVTLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2,3-bis(4-methylbenzoyloxy)butanedioic acid; 1-[(1R)-2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol
• IUPAC Traditional name: (2S,3S)-2,3-bis(4-methylbenzoyloxy)butanedioic acid; venlafaxina [inn-spanish]
• Synonyms: 1-[(1R)-2-(Dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol (2S,3S)-2,3-Bis[(4-methylbenzoyl)oxy]butanedioate Salt; 1-[(1R)-2-(Dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol(2S,3S)-2,3-Bis[(4-methylbenzoyl)oxy]butanedioic Acid Salt; R-Venlafaxine Di-p-toluoyl-D-tartrate Salt

Database IDs

• CAS Number: 272788-00-8
• PubChem SID: 164235389
• PubChem CID: 12050192

CALCULATED PROPERTIES

• Acid pKa: 2.8210018
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.7829022
• LogD (pH = 7.4): -1.8656341
• Log P: 4.1886425
• Molar Refractivity: 95.9398 cm^3
• Polarizability: 37.12853 Å^3
• Polar Surface Area: 127.2 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 120-122°C

DETAILS

Toronto Research Chemicals - V120005

(-)-Venlafaxine derivative as inhibitor of neuronal monoamine reuptake.

REFERENCES

• Yardley, J., et al.: J. Med. Chem., 33(10)
• 2899(10)
• Muth, E., et al.: Drug Dev. Res., 23(10)
• 191 (10)
• Klamerus, K., et al.: J. Clin. Pharmacol., 32, 716 (10)
• Howell, S., et al.: Xenobiotica, 24, 315 (10)
• Muth, E., et al.: Drug Dev. Res., 23(2