3alpha(S)-strictosidine

Also known as C27H34N2O9, Isovincoside

Strictosidine is a natural chemical compound and is classified as a glucoalkaloid and a vinca alkaloid. It is formed by the Pictet–Spengler condensation reaction of tryptamine with secologanin, catalyzed by the enzyme strictosidine synthase. Thousands of strictosidine derivatives are sometimes referred to by the broad phrase of monoterpene indole alkaloids. Strictosidine is an intermediate in the biosynthesis of numerous pharmaceutically valuable metabolites including quinine, camptothecin, ajmalicine, serpentine, vinblastine, vincristine and mitragynine.

Wikidata facts

Has part: hydrogen
Mass: 530.226431

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found in taxon: Palicourea padifolia
chemical formula: C₂₇H₃₄N₂O₉
canonical SMILES: COC(=O)C1=COC(C(C1CC2C3=C(CCN2)C4=CC=CC=C4N3)C=C)OC5C(C(C(C(O5)CO)O)O)O
Commons category: Strictosidine
isomeric SMILES: COC(=O)C1=CO[C@H]([C@@H]([C@@H]1C[C@H]2C3=C(CCN2)C4=CC=CC=C4N3)C=C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O

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Encyclopedic overview

3 sections

Contents

Distribution
Research
References

{{Chembox | ImageFile = Strictosidine skeletal.svg | ImageClass = skin-invert-image | ImageAlt = Structure of strictosidine | IUPACName = Methyl (19S,20R)-19-(β-D-glucopyranosyloxy)-16,17,21,21a-tetradehydro-18-oxa-21a-homo-20,21-secoyohimban-16-carboxylate | SystematicName = Methyl (4S,5R,6S)-5-ethenyl-4-{[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl}-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylate | OtherNames = Isovincoside |Section1= |Section2= }}

Excerpted from Wikipedia’s “3alpha(S)-strictosidine” article, available under the CC BY-SA 4.0 licence.