Epolactaene

Epolactaene is a neuritogenic fungal isolate.[1][2][3]

Epolactaene
Names
IUPAC name
Methyl (2E,3E,5E,9E)-2-ethylidene-11-[(1R,5R)-4-hydroxy-4-methyl-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexan-1-yl]-4,10-dimethyl-11-oxoundeca-3,5,9-trienoate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C21H27NO6/c1-6-15(17(24)27-5)12-13(2)10-8-7-9-11-14(3)16(23)21-18(28-21)20(4,26)22-19(21)25/h6,8,10-12,18,26H,7,9H2,1-5H3,(H,22,25)/b10-8+,13-12+,14-11+,15-6+/t18-,20?,21-/m0/s1
    Key: GFRNQYUCUNYIEN-ZLXMTJSISA-N
  • C/C=C(\C=C(/C)\C=C\CC/C=C(\C)/C(=O)[C@@]12[C@@H](O1)C(NC2=O)(C)O)/C(=O)OC
Properties
C21H27NO6
Molar mass 389.448 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Kakeya, H; Takahashi, I; Okada, G; Isono, K; Osada, H (1995). "Epolactaene, a novel neuritogenic compound in human neuroblastoma cells, produced by a marine fungus". The Journal of Antibiotics. 48 (7): 733–5. doi:10.7164/antibiotics.48.733. PMID 7649877.
  2. Nagumo Y, Kakeya H, Shoji M, Hayashi Y, Dohmae N, Osada H (2005). "Epolactaene binds human Hsp60 Cys442 resulting in the inhibition of chaperone activity". Biochem J. 387 (Pt 3): 835–40. doi:10.1042/BJ20041355. PMC 1135015. PMID 15603555.
  3. Mizushina Y, Kuramochi K, Ikawa H, Kuriyama I, Shimazaki N, Takemura M, et al. (2005). "Structural analysis of epolactaene derivatives as DNA polymerase inhibitors and anti-inflammatory compounds". Int J Mol Med. 15 (5): 785–93. doi:10.3892/ijmm.15.5.785. PMID 15806299.


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