Secologanin

Secologanin
IUPAC name Methyl (2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate
Identifiers
CAS number	19351-63-4
PubChem	161276
ChemSpider	141670
Jmol-3D images	Image 1
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
InChI 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
Properties
Molecular formula	C17H24O10
Molar mass	388.37 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Secologanin is a monoterpene synthesized from geranyl pyrophosphate in the mevalonate pathway. Secologanin then proceedes with dopamine to form ipecac alkaloids.

Biosynthesis

Secologanin biosynthesis begins from geranyl pyrophosphate (GPP) taken from the mevalonate pathway used to make terpenoids. The formation of secologanin begins when GPP forms either 7-deoxyloganate or 7-deoxyloganin from some currently uncharacterized enzymes. 7-Deoxyloganate and 7-deoxyloganin can then be enzymatically reacted with NADPH to form loganate and loganin respectively. Loganate can revert to loganin by the use of an S-adenosyl methionine (SAM). Loganate and loganin can then undergo a further enzyme-catalyzed reaction to form secologanate and secologanin. Another SAM can react with secologanate to form secologanin. Secologanin is then able to proceed onto produce ipecac alkaloids.

Secologanin biosynthesis