Secologanin

Secologanin

Names
IUPAC name Methyl (2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate
Identifiers
CAS Registry Number	19351-63-4
ChemSpider	141670
InChI InChI=1S/C17H24O10/c1-3-8-9(4-5-18)10(15(23)24-2)7-25-16(8)27-17-14(22)13(21)12(20)11(6-19)26-17/h3,5,7-9,11-14,16-17,19-22H,1,4,6H2,2H3/t8-,9+,11-,12-,13+,14-,16+,17+/m1/s1
Jmol-3D images	Image
PubChem	161276
SMILES COC(=O)C1=CO[C@H]([C@@H]([C@@H]1CC=O)C=C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
Properties
Molecular formula	C17H24O10
Molar mass	388.37 g·mol−1
Density	1.42 g/mL
Boiling point	595.5 °C (1,103.9 °F; 868.6 K)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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.

Biosynthesis

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]

References