methyl (1R,12R,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9,13-pentaene-10-carboxylate

• ChemBase ID: 178040
• Molecular Formular: C21H24N2O2
• Molecular Mass: 336.42746
• Monoisotopic Mass: 336.18377802
• SMILES: c1ccc2c(c1)[C@@]13C(=C(C[C@]4([C@@H]1N(CC=C4)CC3)CC)C(=O)OC)N2
• Canonical SMILES: COC(=O)C1=C2Nc3c([C@@]42[C@@H]2[C@@](C1)(CC)C=CCN2CC4)cccc3
• InChI: InChI=1S/C21H24N2O2/c1-3-20-9-6-11-23-12-10-21(19(20)23)15-7-4-5-8-16(15)22-17(21)14(13-20)18(24)25-2/h4-9,19,22H,3,10-13H2,1-2H3/t19-,20-,21-/m0/s1
• InChIKey: FNGGIPWAZSFKCN-ACRUOGEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1R,12R,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2,4,6,9,13-pentaene-10-carboxylate
• IUPAC Traditional name: tabersonine
• Synonyms: (5α,12R,19α)-2,3,6,7-Tetradehydroaspidospermidine-3-carboxylic Acid Methyl Ester; 3a-Ethyl-3a,4,6,11,12,13a-hexahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylic Acid Methyl Ester; Tabersonine; Tabersonin; (-)-Tabersonine; Tabersonine

Database IDs

• CAS Number: 4429-63-4
• PubChem SID: 164233950
• PubChem CID: 20485

CALCULATED PROPERTIES

• Acid pKa: 14.065459
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.6516018
• LogD (pH = 7.4): 0.9023332
• Log P: 2.5878174
• Molar Refractivity: 101.2478 cm^3
• Polarizability: 37.981846 Å^3
• Polar Surface Area: 41.57 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Yellow powder

Product Information

• Purity: 95.0

DETAILS

Toronto Research Chemicals - T003900

(-)-Tabersonine is one of the terpenoid indole alkaloids (TIAs) from Catharanthus roseus. (-)-Tabersonine shows hypotensive activity, anti-tumor activity, hypoglycemic, diuretic activity.

REFERENCES

• Vachnadze, V., et al.: Pharm. Chem. J., 44, 199 (2010)
• Ferreres, F., et al.: J. Pharm. Biomed. Anal., 51, 65 (2010)