1.02011-09-21 00:16:51 UTC2015-07-21 06:57:16 UTCFDB02261124-Hydroxycholesterol24-Hydroxycholesterol (24OHC) is almost exclusively formed in the brain. The enzymatic conversion of CNS cholesterol to 24OHC, which readily crosses the blood-brain barrier, is the major pathway for brain cholesterol elimination and brain cholesterol homeostasis maintenance. The enzyme mediating this conversion has been characterized at the molecular level as cholesterol 24-hydroxylase (EC 1.14.13.98, CYP46) and is mainly located in neurons. Like other oxysterols, 24OHC is efficiently converted into normal bile acids or excreted in bile in its sulfated and glucuronidated form. Levels of 24OHC in the circulation decrease with age in infants and children. In adults, however, the levels appear to be stable. There is accumulating evidence pointing toward a potentially important link between cholesterol, beta-amyloid, and Alzheimer's disease. Patients with active demyelinating diseases had increased levels of 24OHC in cerebrospinal fluid (CSF). Patients with Alzheimer's disease have slightly increased levels of 24OHC in CSF. Patients with multiple sclerosis have a tendency to have higher levels of 24OHC during active periods. (PMID: 15061359, 14574622) [HMDB](24S)-24-Hydroxycholesterol(24S)-cholest-5-ene-3b,24-diol(24S)-cholest-5-ene-3beta,24-diol24-Hydroxycholesterol24(S)-Hydroxycholesterol24S-Cholest-5-ene-3b,24-diol24S-Hydroxy-cholesterol24S-hydroxycholesterolCerebrosterinCerebrosterolCholest-5-en-3b,24S-diolCholest-5-en-3beta,24S-diolCholest-5-en-3β,24S-diolCholest-5-ene-3,24-diolCholest-5-ene-3b,24b-diolC27H46O2402.6529402.349780716(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol24(S)-hydroxycholesterol474-73-7[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@H](O)C(C)CInChI=1S/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26+,27-/m1/s1IOWMKBFJCNLRTC-XWXSNNQWSA-N belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.Dihydroxy bile acids, alcohols and derivativesOrganic compoundsLipids and lipid-like moleculesSteroids and steroid derivativesBile acids, alcohols and derivativesAliphatic homopolycyclic compounds3-beta-hydroxy delta-5-steroids3-beta-hydroxysteroidsCyclic alcohols and derivativesDelta-5-steroidsHydrocarbon derivativesSecondary alcohols24-hydroxysteroid3-beta-hydroxy-delta-5-steroid3-beta-hydroxysteroid3-hydroxy-delta-5-steroid3-hydroxysteroidAlcoholAliphatic homopolycyclic compoundCyclic alcoholDelta-5-steroidDihydroxy bile acid, alcohol, or derivativesHydrocarbon derivativeHydroxysteroidOrganic oxygen compoundOrganooxygen compoundSecondary alcohol24-hydroxycholesterolCholesterol and derivativesoxysterolSolidlogp5.70logs-6.00solubility4.03e-04 g/llogp5.8pka_strongest_acidic18.2pka_strongest_basic-0.95iupac(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-olaverage_mass402.6529mono_mass402.349780716smiles[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@H](O)C(C)CformulaC27H46O2inchiInChI=1S/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26+,27-/m1/s1inchikeyIOWMKBFJCNLRTC-XWXSNNQWSA-Npolar_surface_area40.46refractivity122.21polarizability51.14rotatable_bond_count5acceptor_count2donor_count2physiological_charge0formal_charge0Bile Acid BiosynthesisSMP00035map00120Specdb::CMs15449Specdb::CMs38064Specdb::CMs166221Specdb::MsMs300223Specdb::MsMs300224Specdb::MsMs300225Specdb::MsMs342439Specdb::MsMs342440Specdb::MsMs342441Specdb::MsMs2743585Specdb::MsMs2743586Specdb::MsMs2743587Specdb::MsMs2935958Specdb::MsMs2935959Specdb::MsMs2935960HMDB0141934310#<Reference:0x00005556748f0bb8>#<Reference:0x00005556748f09d8>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