(2E,9R,10S)-2-[3-(methylamino)propylidene]tricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene-9,10-diol

• ChemBase ID: 167855
• Molecular Formular: C19H21NO2
• Molecular Mass: 295.37554
• Monoisotopic Mass: 295.15722892
• SMILES: c12[C@@H]([C@@H](c3c(/C(=C/CCNC)/c1cccc2)cccc3)O)O
• Canonical SMILES: CNCC/C=C/1\c2ccccc2[C@@H]([C@@H](c2c1cccc2)O)O
• InChI: InChI=1S/C19H21NO2/c1-20-12-6-11-13-14-7-2-4-9-16(14)18(21)19(22)17-10-5-3-8-15(13)17/h2-5,7-11,18-22H,6,12H2,1H3/b13-11-/t18-,19+/m1/s1
• InChIKey: GKBCRWFSVWNWQQ-GUYRZELWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,9R,10S)-2-[3-(methylamino)propylidene]tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene-9,10-diol
• IUPAC Traditional name: (2E,9R,10S)-2-[3-(methylamino)propylidene]tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene-9,10-diol
• Synonyms: cis-10,11-Dihydro-5-[3-(methylamino)propylidene]-5H-dibenzo[a,d]cycloheptene-10,11-diol; cis-10,11-Dihydroxy Nortriptyline

Database IDs

• CAS Number: 1562-52-3
• PubChem SID: 162261988
• PubChem CID: 29978805

CALCULATED PROPERTIES

• Acid pKa: 12.976436
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.957326
• LogD (pH = 7.4): -0.57115996
• Log P: 2.2766798
• Molar Refractivity: 98.9355 cm^3
• Polarizability: 34.688694 Å^3
• Polar Surface Area: 52.49 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D454100

A metabolite of Nortriptyline.

REFERENCES

• Prox, A., et al.: Drug Metab. Dispos., 15, 890 (1987)