Hippuristanol

Hippuristanol is a small molecule found in the coral Isis hippuris[1] which was discovered by Jerry Pelletier and others of McGill University in Montreal, Quebec, Canada.[2] It appears to have anti-viral activity and may hold promise as a cancer therapy.[3] Binds to and inhibits the eukaryotic translation initiation factor protein eIF4A.[4]

Hippuristanol
Names
IUPAC name
(24S)-24-Methyl-22β,25-epoxy-5α,22α-furostan-3α,11β,20β-triol
Systematic IUPAC name
(2R,2′R,4′S,4aS,4bS,5S,6aS,6bR,7R,9aS,10aS,10bS,12aS)-4′,4a,5′,5′,6a,7-Hexamethyloctadecahydrospiro[naphtho[2′,1′:4,5]indeno[2,1-b]furan-8,2′-oxolane]-2,5,7-triol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C28H46O5/c1-15-13-28(33-24(15,2)3)27(6,31)23-21(32-28)12-19-18-8-7-16-11-17(29)9-10-25(16,4)22(18)20(30)14-26(19,23)5/h15-23,29-31H,7-14H2,1-6H3/t15-,16-,17+,18-,19-,20-,21-,22+,23-,25-,26-,27+,28+/m0/s1 checkY
    Key: HPHXKNOXVBFETI-SHCCRYCOSA-N checkY
  • InChI=1S/C28H46O5/c1-15-13-28(33-24(15,2)3)27(6,31)23-21(32-28)12-19-18-8-7-16-11-17(29)9-10-25(16,4)22(18)20(30)14-26(19,23)5/h15-23,29-31H,7-14H2,1-6H3/t15-,16-,17+,18-,19-,20-,21-,22+,23-,25-,26-,27+,28+/m0/s1
  • Key: HPHXKNOXVBFETI-SHCCRYCOSA-N
  • [H][C@@]23CC[C@@]1([H])C[C@H](O)CC[C@@](C)1[C@]([H])2[C@@H](O)C[C@@]4(C)[C@@](C[C@@]5([H])[C@@]([H])4[C@](O)(C)[C@]6(C[C@H](C)C(C)(C)O6)O5)3[H]
  • OC(C(=O)NNCNC(=O)c1ccccc1)(c2ccccc2)c3ccccc3
Properties
C28H46O5
Molar mass 462.66 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

See also

References
  1. Bordeleau, Marie-Eve; Mori, Ayaka; Oberer, Monika; Lindqvist, Lisa; Chard, Louisa S; Higa, Tatsuo; Belsham, Graham J; Wagner, Gerhard; Tanaka, Junichi; Pelletier, Jerry (2006). "Functional characterization of IRESes by an inhibitor of the RNA helicase eIF4A". Nature Chemical Biology. 2 (4): 213–220. doi:10.1038/nchembio776. PMID 16532013. S2CID 15635690.
  2. Killer Coral Compound, sciencebase 12 March 2006
  3. Compound from Coral Could Combat Cancer Scientific American March 13, 2006
  4. Cencic, Regina; Pelletier, Jerry (2016-01-02). "Hippuristanol - A potent steroid inhibitor of eukaryotic initiation factor 4A". Translation. Informa UK Limited. 4 (1): e1137381. doi:10.1080/21690731.2015.1137381. ISSN 2169-0731. PMC 4909409. PMID 27335721.
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