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
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
Identifiers
CAS Number	19351-63-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18002
ChemSpider	141670
KEGG	C01852 Y
PubChem CID	161276
UNII	NK7B26K93T Y
CompTox Dashboard (EPA)	DTXSID30941033
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 InChI Key = CSKKDSFETGLMSB-NRZPKYKESA-N
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
Chemical formula	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

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[edit]

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[edit]