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Hamayne

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Hamayne
Names
Systematic IUPAC name (3α,11R,13β)-1,2-Didehydrocrinan-3,11-diol
Other names Bulbispermine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C16H17NO4/c18-10-1-2-16-11-5-13-12(20-8-21-13)3-9(11)6-17(7-15(16)19)14(16)4-10/h1-3,5,10,14-15,18-19H,4,6-8H2/t10-,14-,15-,16+/m0/s1Key: KWAOMPWGIIXDPH-BLQKSXIESA-N
  • InChI=1/C16H17NO4/c18-10-1-2-16-11-5-13-12(20-8-21-13)3-9(11)6-17(7-15(16)19)14(16)4-10/h1-3,5,10,14-15,18-19H,4,6-8H2/t10-,14-,15-,16+/m0/s1Key: KWAOMPWGIIXDPH-BLQKSXIEBO
SMILES
  • C1(C=C231N(C2O)CC4=CC5=C(C=C34)OCO5)O
Properties
Chemical formula C16H17NO4
Molar mass 287.315 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Hamayne is an alkaloid present in plants of the family Amaryllidaceae, including Iberian Narcissus species and two Nigerian Crinum species, reported to have acetylcholinesterase inhibitory activity. The product has been made via total synthesis as well.

References

  1. López, Susana; Bastida, Jaume; Viladomat, Francesc; Codina, Carles (2002). "Acetylcholinesterase inhibitory activity of some Amaryllidaceae alkaloids and Narcissus extracts". Life Sciences. 71 (21): 2521–2529. doi:10.1016/S0024-3205(02)02034-9. PMID 12270757.
  2. Petit, Laurent; Banwell, Martin G.; Willis, Anthony C. (2011). "The Total Synthesis of the Crinine Alkaloid Hamayne via a Pd-Catalyzed Intramolecular Alder-Ene Reaction". Organic Letters. 13 (21): 5800–5803. doi:10.1021/ol2023938. PMID 21970722.


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