Stemmadenine

Stemmadenine is a terpene indole alkaloid. Stemmadenine is believed to be formed from preakuammicine by a carbon-carbon bond cleavage. Cleavage of a second carbon-carbon bond is thought to form dehydrosecodine.^[1] The enzymes forming stemmadenine and using it as a substrate remain unknown to date. It is thought to be intermediate compound in many different biosynthetic pathways^[2][3][4] such as in Aspidosperma species.^[5] Many alkaloids are proposed to be produced through intermediate stemmadenine. Some of them are:

• Catharanthine and Tabersonine in Catharanthus roseus^[4][2]
• Subincanadines D-F in Aspidosperma subincanum^[3]

Quick facts Names, Identifiers ...

Stemmadenine

Names
IUPAC name Methyl (19E)-17-hydroxy-2,7,19,20-tetradehydro-3,7-seco-15β-curan-16-carboxylate
Systematic IUPAC name Methyl (5E,6R,7S)-5-ethylidene-7-(hydroxymethyl)-1,4,5,6,7,8-hexahydro-2H-3,6-ethanoazonino[5,4-b]indole-7-carboxylate
Identifiers
CAS Number	10012-73-4 N[KEGG]
3D model (JSmol)	Interactive image
ChEBI	CHEBI:9260
ChEMBL	ChEMBL486212
ChemSpider	8242264
KEGG	C11691
PubChem CID	10066724
UNII	7RBX39D6AB Y
InChI InChI=1S/C21H26N2O3/c1-3-14-12-23-10-8-16-15-6-4-5-7-18(15)22-19(16)21(13-24,20(25)26-2)17(14)9-11-23/h3-7,17,22,24H,8-13H2,1-2H3/b14-3-/t17-,21+/m1/s1 Key: MBXJCHZRHROMQA-YVDMJPQFSA-N InChI=1/C21H26N2O3/c1-3-14-12-23-10-8-16-15-6-4-5-7-18(15)22-19(16)21(13-24,20(25)26-2)17(14)9-11-23/h3-7,17,22,24H,8-13H2,1-2H3/b14-3-/t17-,21+/m1/s1 Key: MBXJCHZRHROMQA-YVDMJPQFBN
SMILES C/C=C\1/CN2CC[C@H]1[C@](C3=C(CC2)C4=CC=CC=C4N3)(CO)C(=O)OC
Properties
Chemical formula	C21H26N2O3
Molar mass	354.450 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

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It is also present as product in plant like in Tabernaemontana dichotoma seeds.^[6]