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Hippuristanol

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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-Hexamethyloctadecahydrospiroindenofuran-8,2′-oxolane]-2,5,7-triol
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: HPHXKNOXVBFETI-SHCCRYCOSA-N
  • 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
SMILES
  • 23CC1()C(O)CC(C)1()2(O)C4(C)(C5()()4(O)(C)6(C(C)C(C)(C)O6)O5)3
  • OC(C(=O)NNCNC(=O)c1ccccc1)(c2ccccc2)c3ccccc3
Properties
Chemical formula C28H46O5
Molar mass 462.66 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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

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. 4 (1). Informa UK Limited: e1137381. doi:10.1080/21690731.2015.1137381. ISSN 2169-0731. PMC 4909409. PMID 27335721.
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