4α-Methylfecosterol

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4α-Methylfecosterol
4alpha-methylfecosterol.svg
Names
Preferred IUPAC name
(1R,3aR,5aS,6S,7S,9aS,11aR)-6,9a,11a-Trimethyl-1-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,3a,4,5,5a,6,7,8,9,9a,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C29H48O/c1-18(2)19(3)8-9-20(4)23-12-13-25-22-10-11-24-21(5)27(30)15-17-29(24,7)26(22)14-16-28(23,25)6/h18,20-21,23-25,27,30H,3,8-17H2,1-2,4-7H3/t20-,21+,23-,24+,25+,27+,28-,29+/m1/s1
    Key: QLDNWJOJCDIMKK-XLFBYWHPSA-N
  • InChI=1S/C29H48O/c1-18(2)19(3)8-9-20(4)23-12-13-25-22-10-11-24-21(5)27(30)15-17-29(24,7)26(22)14-16-28(23,25)6/h18,20-21,23-25,27,30H,3,8-17H2,1-2,4-7H3/t20-,21+,23-,24+,25+,27+,28-,29+/m1/s1
    Key: QLDNWJOJCDIMKK-XLFBYWHPSA-N
  • C[C@H]1[C@@H]2CCC3=C([C@]2(CC[C@@H]1O)C)CC[C@]4([C@H]3CC[C@@H]4[C@H](C)CCC(=C)C(C)C)C
Properties
C29H48O
Molar mass 412.702 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4α-Methylfecosterol is a metabolic intermediate of sterols made by certain fungis, can be converted to 24-Methylenelophenol by enzyme HYD1, or undergo 4-demethylation to fecosterol.[1][2]

References[edit]

  1. ^ Kuchta, T; Bartková, K; Kubinec, R (30 November 1992). "Ergosterol depletion and 4-methyl sterols accumulation in the yeast Saccharomyces cerevisiae treated with an antifungal, 6-amino-2-n-pentylthiobenzothiazole". Biochemical and Biophysical Research Communications. 189 (1): 85–91. doi:10.1016/0006-291x(92)91529-y. PMID 1449509.
  2. ^ Kuchta, T; Léka, C; Farkas, P; Bujdáková, H; Belajová, E; Russell, NJ (July 1995). "Inhibition of sterol 4-demethylation in Candida albicans by 6-amino-2-n-pentylthiobenzothiazole, a novel mechanism of action for an antifungal agent". Antimicrobial Agents and Chemotherapy. 39 (7): 1538–41. doi:10.1128/aac.39.7.1538. PMC 162777. PMID 7492100.