4α-Methylfecosterol - Misplaced Pages

Chemical compound

4α-Methylfecosterol
Names

IUPAC name 4α-Methyl-5α-campestane-8,24(24)-dien-3β-ol
Systematic IUPAC name (1R,3aR,5aS,6S,7S,9aS,11aR)-6,9a,11a-Trimethyl-1--2,3,3a,4,5,5a,6,7,8,9,9a,10,11,11a-tetradecahydro-1H-cyclopentaphenanthren-7-ol
Identifiers
CAS Number	17757-07-2
3D model (JSmol)	Interactive image
ChEBI	CHEBI:80094
ChemSpider	167937
KEGG	C15776
PubChem CID	193524
CompTox Dashboard (EPA)	DTXSID10938961
InChI 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/s1Key: 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/s1Key: QLDNWJOJCDIMKK-XLFBYWHPSA-N
SMILES C12CCC3=C(2(CC1O)C)CC4(3CC4(C)CCC(=C)C(C)C)C
Properties
Chemical formula	C₂₉H₄₈O
Molar mass	412.702 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

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.

References

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.
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.

to HMG-CoA	Acetyl-CoA Acetoacetyl-CoA HMB HMB-CoA HMG-CoA
Ketone bodies	Acetone Acetoacetic acid β-Hydroxybutyric acid
to DMAPP	Mevalonic acid Phosphomevalonic acid 5-Diphosphomevalonic acid Isopentenyl pyrophosphate Dimethylallyl pyrophosphate
Geranyl-	Geranyl pyrophosphate Geranylgeranyl pyrophosphate
Carotenoid	Prephytoene diphosphate Phytoene

Nonhuman

To Sitosterol	Cycloartenol Cycloeucalenol Obtusifoliol 4α-methylfecosterol Isofucosterol 24-Methylenelophenol Sitosterol More Phytosterols see here instead.
To Ergocalciferol	Fecosterol Episterol Ergostatrienol Ergostatetraenol Ergosterol Ergocalciferol

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