Secologanin

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.

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

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

1. Miettinen K, Dong L, Navrot N, Schneider T, Burlat V, Pollier J, et al. (April 2014). "The seco-iridoid pathway from Catharanthus roseus". Nature Communications. 5 (1): 3606. doi:10.1038/ncomms4606. PMC 3992524. PMID 24710322.
2. "Secologanin Biosynthesis". Nomenclature Committee of the International Union of Biochemistry and Molecular Biology (NC-IUBMB). Retrieved 31 May 2011 – via School of Physical and Chemical Sciences, Queen Mary University of London.