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Macrocarpamine

From Wikipedia, the free encyclopedia
Macrocarpamine
Names
IUPAC name
Methyl (8R,13E,14S,16S,17S,18S)-17-[(E)-2-[(1S,12S,13R,18R)-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4,6,8,16-pentaen-17-yl]ethenyl]-13-ethylidene-1,11-diazapentacyclo[12.3.1.02,7.08,17.011,16]octadeca-2,4,6-triene-18-carboxylate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C41H46N4O3/c1-5-24-21-44-17-15-32-27-11-7-9-13-34(27)45-39(40(46)47-4)29(24)20-37(44)41(32,45)16-14-25-22-48-23-31-28(25)18-36-38-30(19-35(31)42(36)2)26-10-6-8-12-33(26)43(38)3/h5-14,16,22,28-29,31-32,35-37,39H,15,17-21,23H2,1-4H3/b16-14+,24-5-/t28-,29-,31+,32+,35-,36-,37-,39-,41-/m0/s1
    Key: NOKYQXVIWFQLED-HXCLOJFDSA-N
  • C/C=C\1/CN2CC[C@@H]3C4=CC=CC=C4N5[C@@]3([C@@H]2C[C@@H]1[C@H]5C(=O)OC)/C=C/C6=COC[C@@H]7[C@H]6C[C@H]8C9=C(C[C@@H]7N8C)C1=CC=CC=C1N9C
Properties
C41H46N4O3
Molar mass 642.844 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Macrocarpamine is an Alstonia alkaloid with antiplasmodial activity.[1]

References

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  1. ^ Keawpradub, N.; Kirby, G. C.; Steele, J. C.; Houghton, P. J. (1999). "Antiplasmodial activity of extracts and alkaloids of three Alstonia species from Thailand". Planta Medica. 65 (8): 690–694. doi:10.1055/s-1999-14043. PMID 10630106.