From Wikipedia, the free encyclopedia
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
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
C 21 H 27 N O 6
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).
Chemical compound
Epolactaene is a neuritogenic fungal isolate.
[1]
[2]
[3]
References
^ 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 .
^ 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 .
^ 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 .