(2E)-2-[3-(methylamino)propylidene]tricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-9-ol; (2Z)-but-2-enedioic acid

• ChemBase ID: 171009
• Molecular Formular: C23H25NO5
• Molecular Mass: 395.4483
• Monoisotopic Mass: 395.17327291
• SMILES: C1C(c2c(/C(=C/CCNC)/c3c1cccc3)cccc2)O.C(=C\C(=O)O)\C(=O)O
• Canonical SMILES: OC(=O)/C=C\C(=O)O.CNCC/C=C/1\c2ccccc2CC(c2c1cccc2)O
• InChI: InChI=1S/C19H21NO.C4H4O4/c1-20-12-6-11-16-15-8-3-2-7-14(15)13-19(21)18-10-5-4-9-17(16)18;5-3(6)1-2-4(7)8/h2-5,7-11,19-21H,6,12-13H2,1H3;1-2H,(H,5,6)(H,7,8)/b16-11+;2-1-
• InChIKey: ZAXFXQSLHWIUSS-FDVMRUETSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-2-[3-(methylamino)propylidene]tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-9-ol; (2Z)-but-2-enedioic acid
• IUPAC Traditional name: (2E)-2-[3-(methylamino)propylidene]tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-9-ol; maleic acid
• Synonyms: (5E)-10,11-Dihydro-5-[3-(methylamino)propylidene]-5H-dibenzo[a,d]cyclohepten-10-ol (2Z)-2-Butenedioate; (E)-10-Hydroxynortriptyline Maleate; 10-Hydroxy-(E)-nortriptyline Maleate; trans-10-Hydroxynortriptyline Maleate; trans-10-Hydroxy Nortriptyline Maleate

Database IDs

• CAS Number: 74853-74-0
• PubChem SID: 164226919
• PubChem CID: 6440566

CALCULATED PROPERTIES

• Acid pKa: 14.257345
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.038330104
• LogD (pH = 7.4): 0.34782842
• Log P: 3.1956758
• Molar Refractivity: 97.728 cm^3
• Polarizability: 34.036633 Å^3
• Polar Surface Area: 32.26 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H948820

A metabolite of Nortriptyline (N837000).

REFERENCES

• Callaghan, R., et al.: J. Biol. Chem., 268, 16059 (1993)
• Dagenais, C., et al.: Biochem. Pharmacol., 67, 269 (1993)
• Doran, A., et al.: Drug Metab. Dispos., 33, 165 (1993)