3-Hydroxy-16-methoxy-2,3-dihydrotabersonine

3-Hydroxy-16-methoxy-2,3-dihydrotabersonine
Names
	IUPAC name Methyl 3β-hydroxy-16-methoxy-6,7-didehydro-2β,5α,12β,19α-aspidospermidine-3α-carboxylate
	Systematic IUPAC name Methyl (3aR,3a1S,5R,5aR,10bS)-3a-ethyl-5-hydroxy-8-methoxy-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate
Identifiers
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18430;
ChemSpider	389344;
KEGG	C04578;
PubChem CID	440391;
CompTox Dashboard (EPA)	DTXSID801032200 ;
	InChI InChI=1S/C22H28N2O4/c1-4-20-8-5-10-24-11-9-21(18(20)24)15-7-6-14(27-2)12-16(15)23-17(21)22(26,13-20)19(25)28-3/h5-8,12,17-18,23,26H,4,9-11,13H2,1-3H3/t17-,18+,20+,21+,22-/m1/s1 Key: MLIQIRKAHMVCDD-MMGCJVFTSA-N; InChI=1/C22H28N2O4/c1-4-20-8-5-10-24-11-9-21(18(20)24)15-7-6-14(27-2)12-16(15)23-17(21)22(26,13-20)19(25)28-3/h5-8,12,17-18,23,26H,4,9-11,13H2,1-3H3/t17-,18+,20+,21+,22-/m1/s1 Key: MLIQIRKAHMVCDD-MMGCJVFTBW;
	SMILES CC[C@]12C[C@@]([C@H]3[C@@]4([C@H]1N(CC4)CC=C2)c5ccc(cc5N3)OC)(C(=O)OC)O;
Properties
Chemical formula	C22H28N2O4
Molar mass	384.476 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

3-Hydroxy-16-methoxy-2,3-dihydrotabersonine is a terpene indole alkaloid produced by Catharanthus roseus. The metabolite is a substrate for 3-hydroxy-16-methoxy-2,3-dihydrotabersonine N-methyltransferase (NMT) which transfers a methyl group to the nitrogen of the indole ring forming desacetoxyvindoline.^[1] The enzyme catalyzing the formation of 3-hydroxy-16-methoxy-2,3-dihydrotabersonine from 16-methoxytabersonine is currently unknown, but is a result of hydration of the double bond connecting the 6 and 13 position carbons.^[2]^[3]

References

↑ Dethier, Monique; De Luca, Vincenzo (1993). "Partial purification of an N-methyltransferase involved in vindoline biosynthesis in Catharanthus roseus". Phytochemistry. 32 (3): 673–678. doi:10.1016/S0031-9422(00)95153-7.
↑ Liscombe, DK; Usera, AR; O'Connor, SE (2 November 2010). "Homolog of tocopherol C methyltransferases catalyzes N methylation in anticancer alkaloid biosynthesis". Proceedings of the National Academy of Sciences of the United States of America. 107 (44): 18793–8. Bibcode:2010PNAS..10718793L. doi:10.1073/pnas.1009003107. PMC 2973921. PMID 20956330.
↑ O'Connor, Sarah E.; Maresh, Justin J. (2006). "Chemistry and biology of monoterpene indole alkaloid biosynthesis". Natural Product Reports. 23 (4): 532–547. doi:10.1039/B512615K. PMID 16874388.