1.02011-09-21 00:17:30 UTC2015-07-21 06:57:17 UTCFDB0226557a-Hydroxycholesterol7alpha-hydroxycholesterol is an oxysterol and can serve as a biomarker for lipid peroxidation. (PMID: 17386651) Products of cholesterol oxidation accumulate within atherosclerotic plaque and have been proposed to contribute to inflammatory signalling in the diseased artery. (PMID: 17364953)
7alpha-hydroxycholesterol is a cholesterol oxide that has been described as biomarker of oxidative stress in subjects with impaired glucose tolerance and diabetes. (PMID: 16634125) [HMDB]7 alpha-Hydroxycholesterol7-a-Hydroxycholesterol7-alpha-hydroxycholesterol7alpha-HydroxycholesterolCholest-5-ene-3beta,7alpha-diolC27H46O2402.6529402.349780716(1S,2R,5S,9S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol(1S,2R,5S,9S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diolCC(C)CCC[C@@H](C)[C@H]1CC[C@@H]2C3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12CInChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22-,23+,24-,25?,26+,27-/m1/s1OYXZMSRRJOYLLO-AWBHSAGMSA-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 alcohols3-beta-hydroxy-delta-5-steroid3-beta-hydroxysteroid3-hydroxy-delta-5-steroid3-hydroxysteroid7-hydroxysteroidAlcoholAliphatic homopolycyclic compoundCholesterolCholesterol-skeletonCyclic alcoholDelta-5-steroidHydrocarbon derivativeHydroxysteroidOrganic oxygen compoundOrganooxygen compoundSecondary alcoholSolidlogp5.61logs-5.93solubility4.76e-04 g/llogp5.96pka_strongest_acidic18.2pka_strongest_basic-0.83iupac(1S,2R,5S,9S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diolaverage_mass402.6529mono_mass402.349780716smilesCC(C)CCC[C@@H](C)[C@H]1CC[C@@H]2C3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12CformulaC27H46O2inchiInChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22-,23+,24-,25?,26+,27-/m1/s1inchikeyOYXZMSRRJOYLLO-AWBHSAGMSA-Npolar_surface_area40.46refractivity122.06polarizability50.32rotatable_bond_count5acceptor_count2donor_count2physiological_charge0formal_charge0Bile Acid BiosynthesisSMP00035map00120Specdb::CMs23177Specdb::CMs38097Specdb::MsMs317422Specdb::MsMs317423Specdb::MsMs317424Specdb::MsMs363886Specdb::MsMs363887Specdb::MsMs363888HMDB0149617500#<Reference:0x00005556761eb5a0>#<Reference:0x00005556761eb320>#<Reference:0x00005556761eb028>