7-a,25-Dihydroxycholesterol
From DrugPedia: A Wikipedia for Drug discovery
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[edit] Description
7 alpha-hydroxylation is not directly involved, positively or negatively, in the action of 25- or 27-hydroxycholesterol as suppressors of HMG-CoA reductase activity. Human diploid fibroblasts (HDF) and the human melanoma cell line SK-MEL-2 converted 25-hydroxycholesterol into 7 alpha,25-dihydroxycholesterol and 7 alpha,25-dihydroxy-4-cholesten-3-one while the virus-transformed fibroblast line 90VA-VI, the colon carcinoma cell line WiDr and the breast cancer cell line MDA-231 did not express 7 alpha-hydroxylase activity. The 7 alpha-hydroxylation of 25-hydroxycholesterol in HDF could be stimulated by dexamethasone and cortisol and inhibited by metyrapone. An unidentified, possibly 4-hydroxylated, metabolite was formed by 90VA-VI cells and a polar, probably conjugated, metabolite was formed by WiDr cells. The 7 alpha-hydroxylated metabolites of 25-hydroxycholesterol suppressed the activity of HMG-CoA reductase to a similar extent as 25-hydroxycholesterol in HDF but not in 90VA-VI cells, while the 7 alpha-hydroxylated metabolites of 27-hydroxycholesterol suppressed the activity of HMG-CoA reductase also in 90VA-VI cells. (PMID: 9059514)
[edit] General Properties
*Molecular Weight
418.65
*Molecular Formula
C27H46O3
*IUPAC NAME
cholest-5-ene-3beta,7alpha,25-triol
*Canonical Smiles
CC(CCCC(C)(C)O)C1CCC2C3C(O)C=C4CC(O)CCC4(C)C3CCC12C
*Isomeric Smiles
C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
[edit] PhysioChemical Properties
*Melting Point
*LogP
*Water Solubility
