Apicidin

Apicidin
Names
Preferred IUPAC name
(3S,6S,9S,15aR)-9-[(2S)-Butan-2-yl]-6-[(1-methoxy-1H-indol-3-yl)methyl]-3-(6-oxooctyl)octahydro-2H-pyrido[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10(3H,12H)-tetrone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.163.614 Edit this at Wikidata
UNII
  • InChI=1S/C34H49N5O6/c1-5-22(3)30-34(44)38-19-13-12-18-29(38)33(43)35-26(16-9-7-8-14-24(40)6-2)31(41)36-27(32(42)37-30)20-23-21-39(45-4)28-17-11-10-15-25(23)28/h10-11,15,17,21-22,26-27,29-30H,5-9,12-14,16,18-20H2,1-4H3,(H,35,43)(H,36,41)(H,37,42)/t22-,26-,27-,29+,30-/m0/s1
    Key: JWOGUUIOCYMBPV-GMFLJSBRSA-N
  • InChI=1/C34H49N5O6/c1-5-22(3)30-34(44)38-19-13-12-18-29(38)33(43)35-26(16-9-7-8-14-24(40)6-2)31(41)36-27(32(42)37-30)20-23-21-39(45-4)28-17-11-10-15-25(23)28/h10-11,15,17,21-22,26-27,29-30H,5-9,12-14,16,18-20H2,1-4H3,(H,35,43)(H,36,41)(H,37,42)/t22-,26-,27-,29+,30-/m0/s1
    Key: JWOGUUIOCYMBPV-GMFLJSBRBJ
  • CC[C@H](C)[C@H]1C(=O)N2CCCC[C@@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CC3=CN(C4=CC=CC=C43)OC)CCCCCC(=O)CC
Properties
C34H49N5O6
Molar mass 623.795 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Apicidin is a fungal metabolite, as well as a histone deacetylase inhibitor.[1]

References

  1. ^ Han, J. W.; Ahn, S. H.; Park, S. H.; Wang, S. Y.; Bae, G. U.; Seo, D. W.; Kwon, H. K.; Hong, S.; Lee, H. Y.; Lee, Y. W.; Lee, H. W. (November 2000). "Apicidin, a histone deacetylase inhibitor, inhibits proliferation of tumor cells via induction of p21WAF1/Cip1 and gelsolin". Cancer Res. 60 (21): 6068–74. PMID 11085529.



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