1.0 2011-09-21 00:36:09 UTC 2015-07-21 06:57:55 UTC FDB023874 7alpha,25-Dihydroxycholesterol 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) [HMDB] 3b,7a,25-Trihydroxycholest-5-ene 3beta,7alpha,25-Trihydroxycholest-5-ene 3β,7α,25-trihydroxycholest-5-ene 5-Cholesten-3b,7a,25-triol 5-Cholesten-3beta,7alpha,25-triol 5-Cholesten-3β,7α,25-triol 7-a,25-Dihydroxycholesterol 7-alpha,25-Dihydroxycholesterol 7a,25-Dihydroxycholesterol 7alpha,25-Dihydroxycholesterol 7α,25-dihydroxycholesterol Cholest-5-ene-3-b,7-a,25-triol Cholest-5-ene-3-beta,7-alpha,25-triol Cholest-5-ene-3b,7a,25-triol Cholest-5-ene-3beta,7alpha,25-triol Cholest-5-ene-3β,7α,25-triol C27H46O3 418.6523 418.344695338 (1S,2R,5S,9S,10S,11S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol 7α,25-dihydroxycholesterol 64907-22-8 [H][C@@]12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C InChI=1S/C27H46O3/c1-17(7-6-12-25(2,3)30)20-8-9-21-24-22(11-14-27(20,21)5)26(4)13-10-19(28)15-18(26)16-23(24)29/h16-17,19-24,28-30H,6-15H2,1-5H3/t17-,19+,20-,21+,22+,23-,24+,26+,27-/m1/s1 BQMSKLCEWBSPPY-IKVTXIKFSA-N belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Cholesterols and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Cholestane steroids Aliphatic homopolycyclic compounds 3-beta-hydroxy delta-5-steroids 3-beta-hydroxysteroids 7-hydroxysteroids Cyclic alcohols and derivatives Delta-5-steroids Hydrocarbon derivatives Secondary alcohols Tertiary alcohols 25-hydroxysteroid 3-beta-hydroxy-delta-5-steroid 3-beta-hydroxysteroid 3-hydroxy-delta-5-steroid 3-hydroxysteroid 7-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Cholesterol Cholesterol-skeleton Cyclic alcohol Delta-5-steroid Hydrocarbon derivative Hydroxysteroid Organic oxygen compound Organooxygen compound Secondary alcohol Tertiary alcohol 25-hydroxy steroid 7alpha-hydroxy steroid oxysterol Solid logp 4.54 ALOGPS logs -4.91 ALOGPS solubility 5.10e-03 g/l ALOGPS logp 4.49 ChemAxon pka_strongest_acidic 18.2 ChemAxon pka_strongest_basic -0.69 ChemAxon iupac (1S,2R,5S,9S,10S,11S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol ChemAxon average_mass 418.6523 ChemAxon mono_mass 418.344695338 ChemAxon smiles [H][C@@]12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C ChemAxon formula C27H46O3 ChemAxon inchi InChI=1S/C27H46O3/c1-17(7-6-12-25(2,3)30)20-8-9-21-24-22(11-14-27(20,21)5)26(4)13-10-19(28)15-18(26)16-23(24)29/h16-17,19-24,28-30H,6-15H2,1-5H3/t17-,19+,20-,21+,22+,23-,24+,26+,27-/m1/s1 ChemAxon inchikey BQMSKLCEWBSPPY-IKVTXIKFSA-N ChemAxon polar_surface_area 60.69 ChemAxon refractivity 123.89 ChemAxon polarizability 52.17 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Bile Acid Biosynthesis SMP00035 map00120 Specdb::MsMs 297670 Specdb::MsMs 297671 Specdb::MsMs 297672 Specdb::MsMs 339247 Specdb::MsMs 339248 Specdb::MsMs 339249 Specdb::MsMs 2382653 Specdb::MsMs 2382654 Specdb::MsMs 2382655 Specdb::MsMs 2580045 Specdb::MsMs 2580046 Specdb::MsMs 2580047 Specdb::CMs 14355 Specdb::CMs 38990 Specdb::CMs 173555 HMDB06280 37623 #<Reference:0x000055ce305783f8> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823