1.0 2011-09-21 00:08:23 UTC 2015-07-21 06:56:58 UTC FDB022092 5b-Cholestane-3a,7a,12a,25-tetrol 5b-Cholestane-3a,7a,12a,25-tetrol is an intermediates in the bile acid synthetic pathway, and is secreted into the bile and urine following glucuronidation and does not undergo enterohepatic circulation. In cerebrotendinous xanthomatosis (CTX), a bile acid synthesis disorder caused by sterol 27-hydroxylase (CYP27) deficiency, early intermediates and cholestanol accumulate in a variety of tissues, and glucuronides of 25-hydroxylated bile alcohols are released in bile, blood, and urine. Bile acid synthesis from cholesterol is tightly regulated via a feedback mechanism mediated by the farnesoid X receptor (FXR), a nuclear receptor activated by bile acids. Synthesis via the classic pathway is initiated by a series of cholesterol ring modifications and followed by the side chain cleavage. The enhanced cholesterol 7a-hydroxylase (CYP7A1) expression in CYP27 deficiency may be the result of decreased flux of bile acids and bile alcohols into the liver, while production of FXR-activating 5b-Cholestane-3a,7a,12a,25-tetrol is increased. (PMID 15145977) [HMDB] 5b-Cholestan-3a,7a,12a,25-tetrol C27H48O4 436.6676 436.355260024 (1S,2S,5R,7S,9R,10R,11S,15R,16S)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol (1S,2S,5R,7S,9R,10R,11S,15R,16S)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol 18866-87-0 [H][C@@]12CCC([C@H](C)CCCC(C)(C)O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C InChI=1S/C27H48O4/c1-16(7-6-11-25(2,3)31)19-8-9-20-24-21(15-23(30)27(19,20)5)26(4)12-10-18(28)13-17(26)14-22(24)29/h16-24,28-31H,6-15H2,1-5H3/t16-,17+,18-,19?,20+,21+,22-,23+,24+,26+,27-/m1/s1 NTIXPPFPXLYJCT-RUYUEJGQSA-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 derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Cholestane steroids Aliphatic homopolycyclic compounds 12-hydroxysteroids 3-alpha-hydroxysteroids 7-hydroxysteroids Cyclic alcohols and derivatives Hydrocarbon derivatives Polyols Secondary alcohols Tertiary alcohols 12-hydroxysteroid 25-hydroxysteroid 3-alpha-hydroxysteroid 3-hydroxysteroid 7-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Cholesterol Cholesterol-skeleton Cyclic alcohol Hydrocarbon derivative Hydroxysteroid Organic oxygen compound Organooxygen compound Polyol Secondary alcohol Tertiary alcohol Solid logp 3.64 ALOGPS logs -4.33 ALOGPS solubility 2.06e-02 g/l ALOGPS logp 3.51 ChemAxon pka_strongest_acidic 18.3 ChemAxon pka_strongest_basic -0.13 ChemAxon iupac (1S,2S,5R,7S,9R,10R,11S,15R,16S)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol ChemAxon average_mass 436.6676 ChemAxon mono_mass 436.355260024 ChemAxon smiles [H][C@@]12CCC([C@H](C)CCCC(C)(C)O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C ChemAxon formula C27H48O4 ChemAxon inchi InChI=1S/C27H48O4/c1-16(7-6-11-25(2,3)31)19-8-9-20-24-21(15-23(30)27(19,20)5)26(4)12-10-18(28)13-17(26)14-22(24)29/h16-24,28-31H,6-15H2,1-5H3/t16-,17+,18-,19?,20+,21+,22-,23+,24+,26+,27-/m1/s1 ChemAxon inchikey NTIXPPFPXLYJCT-RUYUEJGQSA-N ChemAxon polar_surface_area 80.92 ChemAxon refractivity 124.71 ChemAxon polarizability 52.52 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 21767 Specdb::CMs 37594 Specdb::MsMs 314383 Specdb::MsMs 314384 Specdb::MsMs 314385 Specdb::MsMs 360118 Specdb::MsMs 360119 Specdb::MsMs 360120 HMDB00524 #<Reference:0x000055ce31dc7c10>