16-Hydroxytabersonine

16-Hydroxytabersonine
Names
	IUPAC name Methyl 16-hydroxy-2,3,6,7-tetradehydro-5α,12β,19α-aspidospermidine-3-carboxylate
	Systematic IUPAC name Methyl (3aR,3a1S,10bR)-3a-ethyl-8-hydroxy-3a,3a1,4,6,11,12-hexahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate
	Other names 11-Hydroxytabersonine
Identifiers
CAS Number	22149-28-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	391562;
PubChem CID	443326;
UNII	GV2G76UPD2 ;
CompTox Dashboard (EPA)	DTXSID601032123 ;
	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

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]

References

^ 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.

Names

IUPAC name Methyl 16-hydroxy-2,3,6,7-tetradehydro-5α,12β,19α-aspidospermidine-3-carboxylate
Systematic IUPAC name Methyl (3aR,3a¹S,10bR)-3a-ethyl-8-hydroxy-3a,3a¹,4,6,11,12-hexahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate
Other names 11-Hydroxytabersonine
Identifiers
CAS Number	22149-28-6^Y
3D model (JSmol)	Interactive image
ChemSpider	391562
PubChem CID	443326
UNII	GV2G76UPD2^Y
CompTox Dashboard (EPA)	DTXSID601032123
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