1.02011-09-21 00:36:09 UTC2015-07-21 06:57:55 UTCFDB0238747alpha,25-Dihydroxycholesterol7 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-ene3beta,7alpha,25-Trihydroxycholest-5-ene3β,7α,25-trihydroxycholest-5-ene5-Cholesten-3b,7a,25-triol5-Cholesten-3beta,7alpha,25-triol5-Cholesten-3β,7α,25-triol7-a,25-Dihydroxycholesterol7-alpha,25-Dihydroxycholesterol7a,25-Dihydroxycholesterol7alpha,25-Dihydroxycholesterol7α,25-dihydroxycholesterolCholest-5-ene-3-b,7-a,25-triolCholest-5-ene-3-beta,7-alpha,25-triolCholest-5-ene-3b,7a,25-triolCholest-5-ene-3beta,7alpha,25-triolCholest-5-ene-3β,7α,25-triolC27H46O3418.6523418.344695338(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-diol7α,25-dihydroxycholesterol64907-22-8[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@]12CInChI=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/s1BQMSKLCEWBSPPY-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 derivativesOrganic compoundsLipids and lipid-like moleculesSteroids and steroid derivativesCholestane steroidsAliphatic homopolycyclic compounds3-beta-hydroxy delta-5-steroids3-beta-hydroxysteroids7-hydroxysteroidsCyclic alcohols and derivativesDelta-5-steroidsHydrocarbon derivativesSecondary alcoholsTertiary alcohols25-hydroxysteroid3-beta-hydroxy-delta-5-steroid3-beta-hydroxysteroid3-hydroxy-delta-5-steroid3-hydroxysteroid7-hydroxysteroidAlcoholAliphatic homopolycyclic compoundCholesterolCholesterol-skeletonCyclic alcoholDelta-5-steroidHydrocarbon derivativeHydroxysteroidOrganic oxygen compoundOrganooxygen compoundSecondary alcoholTertiary alcohol25-hydroxy steroid7alpha-hydroxy steroidoxysterolSolidlogp4.54logs-4.91solubility5.10e-03 g/llogp4.49pka_strongest_acidic18.2pka_strongest_basic-0.69iupac(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-diolaverage_mass418.6523mono_mass418.344695338smiles[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@]12CformulaC27H46O3inchiInChI=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/s1inchikeyBQMSKLCEWBSPPY-IKVTXIKFSA-Npolar_surface_area60.69refractivity123.89polarizability52.17rotatable_bond_count5acceptor_count3donor_count3physiological_charge0formal_charge0Bile Acid BiosynthesisSMP00035map00120Specdb::CMs14355Specdb::CMs38990Specdb::CMs173555Specdb::MsMs297670Specdb::MsMs297671Specdb::MsMs297672Specdb::MsMs339247Specdb::MsMs339248Specdb::MsMs339249Specdb::MsMs2382653Specdb::MsMs2382654Specdb::MsMs2382655Specdb::MsMs2580045Specdb::MsMs2580046Specdb::MsMs2580047HMDB0628037623#<Reference:0x00005556758a1f80>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823