1.0 2011-09-21 00:26:47 UTC 2018-05-28 18:36:18 UTC FDB023241 3a,7a,12a-Trihydroxy-5b-cholestanoic acid 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoic acid is a bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. [HMDB] (25R)-3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestan-26-oate (25R)-3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestan-26-oic acid (3a,5b,7a,12a,25R)-3,7,12-Trihydroxycholestan-26-Oate (3a,5b,7a,12a,25R)-3,7,12-Trihydroxycholestan-26-Oic acid (3alpha,5beta,7alpha,12alpha,25R)-3,7,12-Trihydroxycholestan-26-Oate (3alpha,5beta,7alpha,12alpha,25R)-3,7,12-Trihydroxycholestan-26-Oic acid (3α,5β,7α,12α,25R)-3,7,12-trihydroxycholestan-26-Oate (3α,5β,7α,12α,25R)-3,7,12-trihydroxycholestan-26-Oic acid 3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestanate 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoate 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoic acid C27H46O5 450.6511 450.334524582 (2R,6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoic acid (2R,6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoic acid 547-98-8 [H][C@@]12CC[C@H]([C@H](C)CCC[C@@H](C)C(O)=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/C27H46O5/c1-15(6-5-7-16(2)25(31)32)19-8-9-20-24-21(14-23(30)27(19,20)4)26(3)11-10-18(28)12-17(26)13-22(24)29/h15-24,28-30H,5-14H2,1-4H3,(H,31,32)/t15-,16-,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1 CNWPIIOQKZNXBB-WBYPBBSPSA-N belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. Trihydroxy bile acids, alcohols and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Bile acids, alcohols and derivatives Aliphatic homopolycyclic compounds 12-hydroxysteroids 3-alpha-hydroxysteroids 7-hydroxysteroids Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Hydrocarbon derivatives Hydroxy fatty acids Medium-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Polyols Secondary alcohols Steroid acids 12-hydroxysteroid 3-alpha-hydroxysteroid 3-hydroxysteroid 7-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Fatty acid Fatty acyl Hydrocarbon derivative Hydroxy fatty acid Hydroxysteroid Medium-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Polyol Secondary alcohol Steroid acid Trihydroxy bile acid, alcohol, or derivatives 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oic acid C27 bile acids, alcohols, and derivatives Solid logp 3.12 ALOGPS logs -4.30 ALOGPS solubility 2.25e-02 g/l ALOGPS logp 3.91 ChemAxon pka_strongest_acidic 4.62 ChemAxon pka_strongest_basic -0.16 ChemAxon iupac (2R,6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoic acid ChemAxon average_mass 450.6511 ChemAxon mono_mass 450.334524582 ChemAxon smiles [H][C@@]12CC[C@H]([C@H](C)CCC[C@@H](C)C(O)=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 C27H46O5 ChemAxon inchi InChI=1S/C27H46O5/c1-15(6-5-7-16(2)25(31)32)19-8-9-20-24-21(14-23(30)27(19,20)4)26(3)11-10-18(28)12-17(26)13-22(24)29/h15-24,28-30H,5-14H2,1-4H3,(H,31,32)/t15-,16-,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1 ChemAxon inchikey CNWPIIOQKZNXBB-WBYPBBSPSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 124.57 ChemAxon polarizability 53.21 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Bile Acid Biosynthesis SMP00035 map00120 Specdb::CMs 14550 Specdb::CMs 38666 Specdb::MsMs 77148 Specdb::MsMs 77149 Specdb::MsMs 77150 Specdb::MsMs 137202 Specdb::MsMs 137203 Specdb::MsMs 137204 HMDB03873 18402 #<Reference:0x000055ce2d046f90> Bile acyl-CoA synthetase Q9Y2P5 SLC27A5