Compound: Tabersonine
SMILES: O=C(OC)C1=C2Nc3ccccc3[C@]24[C@H]5N(CC=C[C@]5(C1)CC)CC4
InChIKey: FNGGIPWAZSFKCN-ACRUOGEOSA-N
Synonyms: Tabersonine, 4429-63-4, Tabersonin, MN955K48NB, Aspidospermidine-3-carboxylic acid, 2,3,6,7-tetradehydro-, methyl ester, (5alpha,12beta,19alpha)-, CHEBI:16776, DTXSID30196102, methyl 2,3,6,7-tetradehydro-5alpha,12beta,19alpha-aspidospermidine-3-carboxylate, 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, 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, RefChem:187087, DTXCID00118593, 224-615-0, (-)-Tabersonine, MFCD28140545, (5alpha,12beta,19alpha)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylic acid, methyl ester, methyl (5alpha,12beta,19alpha)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylate, Methyl (3aR,3a1S,10bR)-3a-ethyl-3a,3a1,4,6,11,12-hexahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate, EINECS 224-615-0, BRN 0050163, Vinpocetine Impurity 42, UNII-MN955K48NB, 4-25-00-00997 (Beilstein Handbook Reference), SCHEMBL829379, CHEMBL2011511, Tabersonine, >=95% (HPLC), FNGGIPWAZSFKCN-ACRUOGEOSA-N, GLXC-06267, HMS3887M03, HY-N1431, NSC815334, s9427, AKOS015896776, CCG-267873, EBC-461044, FT27985, NSC-815334, NCGC00488792-01, 3a-Ethyl-3a,4,6,11,12,13a-hexahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylic Acid Methyl Ester, AC-26458, Aspidospermidine-3-carboxylic acid, 2,3,6,7-tetradehydro-, methyl ester, (5.alpha.,12.beta.,19.alpha.)-, Aspidospermidine-3-carboxylic acid, 2,3,6,7-tetrahydro-, methyl ester, (5-alpha,12-beta,19-alpha)-, DA-58232, CS-0016859, NS00031405, C09244, Q21099578, (5?,12?,19?)-2,3,6,7-Tetradehydro-aspidospermidine-3-carboxylic acid methyl ester, Methyl 5alpha,12beta,19alpha-2,3,6,7-tetradehydroaspidospermidine-3-carboxylate, Methyl(5alpha,19alpha)-16-methoxy-8-oxo-2,3,6,7-tetradehydroaspidospermidine-3-carboxylate, (-)-Tabersonine; (5|A,12|A,19|A)-2,3,6,7-Tetrahydro-aspidospermidine-3-carboxylic acid methyl ester; Tabersonin, 1H-INDOLIZINO(8,1-CD)CARBAZOLE-5-CARBOXYLIC ACID, 3A-ETHYL-3A,4,6,11,12,13A-HEXAHYDRO-, METHYL ESTER, 21217-98-1, ASPIDOSPERMIDINE-3-CARBOXYLIC ACID, 2,3,6,7-TETRADEHYDRO-, METHYL ESTER, (5.ALPHA.,12R,19.ALPHA.)-, methyl (1R,12R,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,9,13-pentaene-10-carboxylate, 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
Theoretical properties:
molecular_formula: C21H24N2O2
molecular_weight: 336.4 g/mol
exact_mass: 336.183778013 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 3
heavy_atom_count: 25
topological_polar_surface_area: 41.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Tabersonine is a monoterpenoid indole alkaloid with cytotoxic activity. It has a role as a metabolite and an antineoplastic agent. It is a methyl ester, an organic heteropentacyclic compound, an alkaloid ester and a monoterpenoid indole alkaloid. It is a conjugate base of a tabersoninium(1+).
chebi: A monoterpenoid indole alkaloid with cytotoxic activity.
chembl: TABERSONINE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Tabersonine is a terpene indole alkaloid found in the medicinal plant Catharanthus roseus and also plants in the genus Voacanga (both taxa belonging to the alkaloid-rich family Apocynaceae).  Tabersonine is hydroxylated at the 16 position by the enzyme tabersonine 16-hydroxylase to form 16-hydroxytabersonine. Tabersonine is the first intermediate leading to the formation of vindoline one of the two precursors required for vinblastine biosynthesis.