(2S,3S,4S,5R,6S)-6-({2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 170666
• Molecular Formular: C25H32N2O7
• Molecular Mass: 472.53078
• Monoisotopic Mass: 472.22095137
• SMILES: O1[C@H]([C@@H](O)[C@H]([C@@H]([C@@H]1C(=O)O)O)O)Oc1ccc2N(c3c(CCc2c1)cccc3)CCCN(C)C
• Canonical SMILES: CN(CCCN1c2ccc(cc2CCc2c1cccc2)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C25H32N2O7/c1-26(2)12-5-13-27-18-7-4-3-6-15(18)8-9-16-14-17(10-11-19(16)27)33-25-22(30)20(28)21(29)23(34-25)24(31)32/h3-4,6-7,10-11,14,20-23,25,28-30H,5,8-9,12-13H2,1-2H3,(H,31,32)/t20-,21-,22+,23-,25+/m0/s1
• InChIKey: CBEJFHYWZSCYSD-LYVDORBWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-({2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-({2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 5-[3-(Dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepin-2-yl β-D-Glucopyranosiduronic Acid; 2-Hydroxyimipramine Glucuronide; 2-Hydroxy Imipramine β-D-Glucuronide

Database IDs

• CAS Number: 54190-76-0
• PubChem SID: 164226576
• PubChem CID: 10874382

CALCULATED PROPERTIES

• Acid pKa: 2.994587
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -0.7047053
• LogD (pH = 7.4): -0.7093026
• Log P: -0.70409447
• Molar Refractivity: 124.5983 cm^3
• Polarizability: 48.70338 Å^3
• Polar Surface Area: 122.93 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Pale Yellow Solid
• Melting Point: 177-179°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H943410

A metabolite of Imipramine.

REFERENCES

• Gram, L.F., et al.: Clin. Pharmacol. Therap., 17, 555 (1975)
• Hackett, A.M., et al.: Xenobiotica, 14, 491 (1975)
• Chiba, M., et al.: Biochem. Pharmacol., 39, 367 (1975)