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16-Hydroxytabersonine

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16-Hydroxytabersonine
Names
IUPAC name Methyl 16-hydroxy-2,3,6,7-tetradehydro-5α,12β,19α-aspidospermidine-3-carboxylate
Systematic IUPAC name Methyl (3aR,3aS,10bR)-3a-ethyl-8-hydroxy-3a,3a,4,6,11,12-hexahydro-1H-indolizinocarbazole-5-carboxylate
Other names 11-Hydroxytabersonine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C21H24N2O3/c1-3-20-7-4-9-23-10-8-21(19(20)23)15-6-5-13(24)11-16(15)22-17(21)14(12-20)18(25)26-2/h4-7,11,19,22,24H,3,8-10,12H2,1-2H3/t19-,20-,21-/m0/s1Key: FXUFRJQCBVSCRZ-ACRUOGEOSA-N
  • InChI=1/C21H24N2O3/c1-3-20-7-4-9-23-10-8-21(19(20)23)15-6-5-13(24)11-16(15)22-17(21)14(12-20)18(25)26-2/h4-7,11,19,22,24H,3,8-10,12H2,1-2H3/t19-,20-,21-/m0/s1Key: FXUFRJQCBVSCRZ-ACRUOGEOBW
SMILES
  • CC12CC(=C34(1N(CC4)CC=C2)c5ccc(cc5N3)O)C(=O)OC
Properties
Chemical formula C21H24N2O3
Molar mass 352.434 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

16-Hydroxytabersonine is a terpene indole alkaloid produced by the plant Catharanthus roseus. The metabolite is an intermediate in the formation of vindoline, a precursor needed for formation of the pharmaceutically valuable vinblastine and vincristine. 16-hydroxytabersonine is formed from the hydroxylation of tabersonine by tabersonine 16-hydroxylase (T16H). Tabersonine 16-O-methyltransferase (16OMT) methylates the hydroxylated 16 position to form 16-methoxytabersonine.

References

  1. Levac, Dylan; Murata, Jun; Kim, Won S.; De Luca, Vincenzo (2008). "Application of carborundum abrasion for investigating the leaf epidermis: Molecular cloning of Catharanthus roseus 16-hydroxytabersonine-16-O-methyltransferase". The Plant Journal. 53 (2): 225–236. doi:10.1111/j.1365-313X.2007.03337.x. PMID 18053006.
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