Secologanin is a secoiridoid monoterpene synthesized from geranyl pyrophosphate in the mevalonate pathway. Secologanin then proceeds with dopamine or tryptamine to form ipecac and terpene indole alkaloids, respectively.
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IUPAC name
Methyl (2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate
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Systematic IUPAC name
Methyl (4S,5R,6S)-3-ethenyl-4-(2-oxoethyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate | |
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3D model (JSmol)
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ChEBI |
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PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |
C17H24O10 | |
Molar mass | 388.369 g·mol−1 |
Density | 1.42 g/mL |
Boiling point | 595.5 °C (1,103.9 °F; 868.6 K) |
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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Secologanin biosynthesis begins from geranyl pyrophosphate (GPP) taken from the mevalonate pathway used to make terpenoids. Recent efforts have characterized the entire secologanin biosynthetic pathway.[1] Secologanin is formed from loganin through the action of the enzyme secologanin synthase. Secologanin is then able to proceed onto produce ipecac and terpene indole alkaloids.[2]