Tabersonine

Chemical compound From Wikipedia, the free encyclopedia

Tabersonine is a terpene indole alkaloid found in the medicinal plant Catharanthus roseus and also plants in the genus Voacanga[1]: 8  (both taxa belonging to the alkaloid-rich family Apocynaceae). Tabersonine is hydroxylated at the 16 position by the enzyme tabersonine 16-hydroxylase (T16H) to form 16-hydroxytabersonine.[2] The enzyme leading to its formation is currently unknown. Tabersonine is the first intermediate leading to the formation of vindoline one of the two precursors required for vinblastine biosynthesis.

Quick facts Names, Identifiers ...
Tabersonine
Names
IUPAC name
Methyl 2,3,6,7-tetradehydro-5α,12β,19α-aspidospermidine-3-carboxylate
Systematic IUPAC name
Methyl (3aR,3a1S,10bR)-3a-ethyl-3a,3a1,4,6,11,12-hexahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate
Identifiers
3D model (JSmol)
ChemSpider
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UNII
  • 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
    Key: FNGGIPWAZSFKCN-ACRUOGEOSA-N
  • InChI=1/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
    Key: FNGGIPWAZSFKCN-ACRUOGEOBF
  • CC[C@]12CC(=C3[C@@]4([C@H]1N(CC4)CC=C2)c5ccccc5N3)C(=O)OC
Properties
C21H24N2O2
Molar mass 336.435 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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