(-)-secologanin

Also known as methyl (2S,3R,4S)-4-(formylmethyl)-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate, 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.

Chemical data

Formula: C17H24O10
Molecular weight: 388.4 g/mol
IUPAC name: methyl (2S,3R,4S)-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
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
InChIKey: CSKKDSFETGLMSB-NRZPKYKESA-N
XLogP: -1.6
Polar surface area: 152 Å²
H-bond donors: 4
H-bond acceptors: 10
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Has part: hydrogen
Mass: 388.137

Show 5 more facts

chemical formula: C₁₇H₂₄O₁₀
found in taxon: Pterocephalus perennis
isomeric 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
canonical SMILES: COC(=O)C1=COC(C(C1CC=O)C=C)OC2C(C(C(C(O2)CO)O)O)O
Commons category: Secologanin

Sources (2)

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Encyclopedic overview

2 sections

Contents

Biosynthesis
References

{{Chembox | ImageFile = Secologanin.svg | ImageSize = 200px | IUPACName = Methyl (2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate | SystematicName = 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 | OtherNames = |Section1= |Section2= }}

Excerpted from Wikipedia’s “(-)-secologanin” article, available under the CC BY-SA 4.0 licence.

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