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5-Dehydroepisterol

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5-Dehydroepisterol
Names
IUPAC name
(3S,10R,13R)-17-[(1R)-1,5-dimethyl-4-methylenehexyl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
Other names
24-Methylcholesta-5,7,24(28)-trienol, ergosta-5,7,24(28)-trien-3β-ol, campesta-7,24(28)-dien-3β-ol
Identifiers
3D model (JSmol)
ChemSpider
KEGG
Properties
C28H44O
Molar mass 396.648 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

5-Dehydroepisterol is a sterol and an intermediate in steroid biosynthesis, particularly synthesis of brassinosteroids.[1] It is formed from episterol through action of ERG3, the C-5 sterol desaturase in the yeast[2] and is then converted into 24-methylenecholesterol by 7-dehydrocholesterol reductase.[3]

Episterol and 5-dehydroepisterol are found in Leishmania.[4][5]

References

  1. ^ Pathway ko00100 at KEGG Pathway Database.
  2. ^ Reaction R07491 at KEGG Pathway Database.
  3. ^ Reaction R07492 at KEGG Pathway Database.
  4. ^ Goad LJ, Holz GG, Beach DH (June 1985). "Sterols of ketoconazole-inhibited Leishmania mexicana mexicana promastigotes". Mol Biochem Parasitol. 15 (3): 257–79. doi:10.1016/0166-6851(85)90089-1. PMID 4033689.
  5. ^ Rodrigues JC, Attias M, Rodriguez C, Urbina JA, Souza W (February 2002). "Ultrastructural and Biochemical Alterations Induced by 22,26-Azasterol, a Δ24(25)-Sterol Methyltransferase Inhibitor, on Promastigote and Amastigote Forms of Leishmania amazonensis". Antimicrob Agents Chemother. 46 (2): 487–99. doi:10.1128/AAC.46.2.487-499.2002. PMC 127026. PMID 11796362.
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5-Dehydroepisterol
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