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5-Dehydroepisterol

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5-Dehydroepisterol
Names
IUPAC name (3S,10R,13R)-17--10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopentaphenanthren-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
CAS Number
3D model (JSmol)
KEGG
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9-10,18,20,22,24-26,29H,3,7-8,11-17H2,1-2,4-6H3/t20-,22+,24-,25+,26+,27+,28-/m1/s1
SMILES
  • CC(C)C(=C)CCC(C)C1CCC2C1(CCC3C2=CC=C4C3(CCC(C4)O)C)C
Properties
Chemical formula C28H44O
Molar mass 396.648 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

5-Dehydroepisterol is a sterol and an intermediate in steroid biosynthesis, particularly synthesis of brassinosteroids. It is formed from episterol through action of the enzyme lathosterol oxidase, and is then converted into 24-methylenecholesterol by 7-dehydrocholesterol reductase.

Episterol and 5-dehydroepisterol are found in Leishmania.

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 (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  5. Rodrigues JC, Attias M, Rodriguez C, Urbina JA, Souza W (2002). "Ultrastructural and biochemical alterations induced by 22,26-azasterol, a delta(24(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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)


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