16-Hydroxytabersonine

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.[1]

16-Hydroxytabersonine

Names
IUPAC name Methyl (5α,12β,19α)-16-hydroxy-2,3,6,7-tetradehydroaspidospermidine-3-carboxylate
Other names 11-Hydroxytabersonine
Identifiers
CAS Number	22149-28-6
3D model (JSmol)	Interactive image
ChemSpider	391562
PubChem CID	443326
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/s1 Key: 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/s1 Key: FXUFRJQCBVSCRZ-ACRUOGEOBW
SMILES CC[C@]12CC(=C3[C@@]4([C@H]1N(CC4)CC=C2)c5ccc(cc5N3)O)C(=O)OC
Properties
Chemical formula	C21H24N2O3
Molar mass	352.434 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References

1. Levac, Murata, Kim and De Luca (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