(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-{3-[(2H3)methylamino]propyl}-2-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-6-yl)oxy]oxane-2-carboxylic acid

• ChemBase ID: 170439
• Molecular Formular: C24H30N2O7
• Molecular Mass: 458.5042
• Monoisotopic Mass: 458.20530131
• SMILES: O1[C@H]([C@@H](O)[C@H]([C@@H]([C@@H]1C(=O)O)O)O)Oc1ccc2N(c3c(CCc2c1)cccc3)CCCNC
• Canonical SMILES: CNCCCN1c2ccc(cc2CCc2c1cccc2)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C24H30N2O7/c1-25-11-4-12-26-17-6-3-2-5-14(17)7-8-15-13-16(9-10-18(15)26)32-24-21(29)19(27)20(28)22(33-24)23(30)31/h2-3,5-6,9-10,13,19-22,24-25,27-29H,4,7-8,11-12H2,1H3,(H,30,31)/t19-,20-,21+,22-,24+/m0/s1
• InChIKey: XJHAOJJEVSPMBA-QMDPOKHVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-{3-[(^2H₃)methylamino]propyl}-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-6-yl)oxy]oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-{3-[(^2H₃)methylamino]propyl}-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-6-yl)oxy]oxane-2-carboxylic acid
• Synonyms: 10,11-Dihydro-5-[3-(methyl-d3-amino)propyl]-5H-dibenz[b,f]azepin-2-yl β-D-Glucopyranosiduronic Acid; 2-Hydroxydemethylimipramine-d3 Glucuronide; 2-Hydroxydesmethylimipramine-d3 Glucuronide; 2-Hydroxy Desipramine-d3 β-D-Glucuronide

Database IDs

• PubChem SID: 164226349
• PubChem CID: 71748974

CALCULATED PROPERTIES

• Acid pKa: 2.997017
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -0.8284609
• LogD (pH = 7.4): -0.8282882
• Log P: -0.827733
• Molar Refractivity: 119.3036 cm^3
• Polarizability: 46.870148 Å^3
• Polar Surface Area: 131.72 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H936512

A labelled metabolite of Desipramine.

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)