methyl (2S,3S,4S,5R,6S)-6-({[(1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl](methyl)carbamoyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 177752
• Molecular Formular: C25H27Cl2NO8
• Molecular Mass: 540.38978
• Monoisotopic Mass: 539.11137219
• SMILES: c1cccc2c1[C@H](CC[C@H]2c1ccc(c(c1)Cl)Cl)N(C)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)OC
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](OC(=O)N([C@H]2CC[C@H](c3c2cccc3)c2ccc(c(c2)Cl)Cl)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C25H27Cl2NO8/c1-28(25(33)36-24-21(31)19(29)20(30)22(35-24)23(32)34-2)18-10-8-13(14-5-3-4-6-15(14)18)12-7-9-16(26)17(27)11-12/h3-7,9,11,13,18-22,24,29-31H,8,10H2,1-2H3/t13-,18-,19-,20-,21+,22-,24-/m0/s1
• InChIKey: OICRHAMFPCCLSL-JQADKIMNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-6-({[(1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl](methyl)carbamoyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-6-({[(1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl](methyl)carbamoyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: (1S-cis)-1-[[4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenyl]methycarbamate]-β-D-glucopyranuronic Acid Methyl Ester; Sertraline Carbamoyl-O-glucuronide Methyl Ester; Sertraline Carbamoyl Glucuronide Methyl Ester

Database IDs

• PubChem SID: 164233662
• PubChem CID: 71752188

CALCULATED PROPERTIES

• Acid pKa: 12.160342
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 3.4307396
• LogD (pH = 7.4): 3.4307323
• Log P: 3.4307399
• Molar Refractivity: 129.2291 cm^3
• Polarizability: 51.501846 Å^3
• Polar Surface Area: 125.76 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate; Metanol

DETAILS

Toronto Research Chemicals - S279995

Protected metabolite of the antidepressant Sertraline.