1.0 2011-09-21 00:16:51 UTC 2015-07-21 06:57:16 UTC FDB022611 24-Hydroxycholesterol 24-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-diol 24-Hydroxycholesterol 24(S)-Hydroxycholesterol 24S-Cholest-5-ene-3b,24-diol 24S-Hydroxy-cholesterol 24S-hydroxycholesterol Cerebrosterin Cerebrosterol Cholest-5-en-3b,24S-diol Cholest-5-en-3beta,24S-diol Cholest-5-en-3β,24S-diol Cholest-5-ene-3,24-diol Cholest-5-ene-3b,24b-diol C27H46O2 402.6529 402.349780716 (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-ol 24(S)-hydroxycholesterol 474-73-7 [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)C InChI=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/s1 IOWMKBFJCNLRTC-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 derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Bile acids, alcohols and derivatives Aliphatic homopolycyclic compounds 3-beta-hydroxy delta-5-steroids 3-beta-hydroxysteroids Cyclic alcohols and derivatives Delta-5-steroids Hydrocarbon derivatives Secondary alcohols 24-hydroxysteroid 3-beta-hydroxy-delta-5-steroid 3-beta-hydroxysteroid 3-hydroxy-delta-5-steroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Cyclic alcohol Delta-5-steroid Dihydroxy bile acid, alcohol, or derivatives Hydrocarbon derivative Hydroxysteroid Organic oxygen compound Organooxygen compound Secondary alcohol 24-hydroxycholesterol Cholesterol and derivatives oxysterol Solid logp 5.70 ALOGPS logs -6.00 ALOGPS solubility 4.03e-04 g/l ALOGPS logp 5.8 ChemAxon pka_strongest_acidic 18.2 ChemAxon pka_strongest_basic -0.95 ChemAxon iupac (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-ol ChemAxon average_mass 402.6529 ChemAxon mono_mass 402.349780716 ChemAxon smiles [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)C ChemAxon formula C27H46O2 ChemAxon inchi InChI=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/s1 ChemAxon inchikey IOWMKBFJCNLRTC-XWXSNNQWSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 122.21 ChemAxon polarizability 51.14 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Bile Acid Biosynthesis SMP00035 map00120 Specdb::CMs 15449 Specdb::CMs 38064 Specdb::CMs 166221 Specdb::MsMs 300223 Specdb::MsMs 300224 Specdb::MsMs 300225 Specdb::MsMs 342439 Specdb::MsMs 342440 Specdb::MsMs 342441 Specdb::MsMs 2743585 Specdb::MsMs 2743586 Specdb::MsMs 2743587 Specdb::MsMs 2935958 Specdb::MsMs 2935959 Specdb::MsMs 2935960 HMDB01419 34310 #<Reference:0x000055ce32c69f70> #<Reference:0x000055ce32c69d68> 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