1.0 2016-09-30 23:21:13 UTC 2020-04-22 15:17:11 UTC BMDB0006283 BMDB06283 20α-Hydroxycholesterol 20alpha-Hydroxycholesterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 20alpha-hydroxycholesterol is considered to be a sterol lipid molecule. 20alpha-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 20alpha-Hydroxycholesterol participates in a number of enzymatic reactions, within cattle. In particular, 20alpha-Hydroxycholesterol can be converted into 20a,22b-dihydroxycholesterol; which is mediated by the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In addition, 20alpha-Hydroxycholesterol can be biosynthesized from cholesterol through the action of the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In cattle, 20alpha-hydroxycholesterol is involved in the metabolic pathway called the steroidogenesis pathway. 20a-Hydroxycholesterol 20Α-hydroxycholesterol (20S)-20-Hydroxycholesterol (20S)-Cholest-5-ene-3 beta,20-diol 20 alpha-Hydroxycholesterol 20-Hydroxycholesterol 20-Hydroxycholesterol, (3beta,20 xi)-isomer 20-Hydroxycholesterol, 3H-labeled, (3beta,20 xi)-isomer 20R-Hydroxycholesterol (3beta,20R)-Cholest-5-ene-3,20-diol 20alpha-Hydroxy cholesterol C27H46O2 402.6529 402.349780716 (1S,2R,5S,10S,11S,14S,15S)-14-[(2R)-2-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol 20a-hydroxy cholesterol 516-72-3 CC(C)CCC[C@@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C InChI=1S/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27+/m0/s1 MCKLJFJEQRYRQT-MGNSQDQZSA-N belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Cholestane steroids Cholesterols and derivatives 3-beta-hydroxy delta-5-steroids 3-beta-hydroxysteroids Cyclic alcohols and derivatives Delta-5-steroids Hydrocarbon derivatives Secondary alcohols Tertiary alcohols 20-hydroxysteroid 3-beta-hydroxy-delta-5-steroid 3-beta-hydroxysteroid 3-hydroxy-delta-5-steroid 3-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 Aliphatic homopolycyclic compounds Cholesterol and derivatives Solid logp 6.06 ALOGPS logs -5.85 ALOGPS logp 5.8 ChemAxon pka_strongest_acidic 18.2 ChemAxon pka_strongest_basic -0.26 ChemAxon iupac (1S,2R,5S,10S,11S,14S,15S)-14-[(2R)-2-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 CC(C)CCC[C@@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C ChemAxon formula C27H46O2 ChemAxon inchi InChI=1S/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27+/m0/s1 ChemAxon inchikey MCKLJFJEQRYRQT-MGNSQDQZSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 122.3 ChemAxon polarizability 51.1 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Steroidogenesis SMP0087238 Specdb::CMs 22723 Specdb::CMs 38992 Specdb::CMs 130505 Specdb::CMs 138239 Specdb::MsMs 254844 Specdb::MsMs 254845 Specdb::MsMs 254846 Specdb::MsMs 274785 Specdb::MsMs 274786 Specdb::MsMs 274787 Specdb::MsMs 2805750 Specdb::MsMs 2805751 Specdb::MsMs 2805752 Specdb::MsMs 2876846 Specdb::MsMs 2876847 Specdb::MsMs 2876848 FDB023876 440711 DB04704 389586 1296 C05500 HC2 20A-HYDROXY-CHOLESTEROL 1443018 Mijares, A.; Cargill, David I.; Glasel, Jay A.; Lieberman, Seymour. C-20 epimers of 20-hydroxycholesterol. Journal of Organic Chemistry (1967), 32(3), 810-12.