Names | |
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IUPAC name
Methyl 3β-hydroxy-16-methoxy-6,7-didehydro-2β,5α,12β,19α-aspidospermidine-3α-carboxylate
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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)
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ChEBI | |
ChemSpider | |
KEGG | |
PubChem
CID
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CompTox Dashboard (
EPA)
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Properties | |
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).
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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]
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)
|
|
ChEBI | |
ChemSpider | |
KEGG | |
PubChem
CID
|
|
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
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).
|
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]