1.0 2011-09-21 01:53:50 UTC 2015-07-21 06:59:41 UTC FDB029314 1beta,3alpha,7beta-Trihydroxy-5beta-cholanoic acid 1b,3a,7b-Trihydroxy-5b-cholanoic 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 1, 3, and 7. 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 holesterol. 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. (PMID: 11316487, 16037564, 12576301, 11907135) [HMDB] 1b,3a,7b-Trihydroxy-5b-cholanate 1b,3a,7b-Trihydroxy-5b-cholanic acid 1b,3a,7b-Trihydroxy-5b-cholanoate 1b,3a,7b-Trihydroxy-5b-cholanoic acid C24H40O6 424.5708 424.282489012 (5R)-5-hydroxy-5-[(2S,3R,5S,9S,15S)-3,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid (5R)-5-hydroxy-5-[(2S,3R,5S,9S,15S)-3,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(O)=O)[C@@H](O)CC1C[C@H](O)C[C@@H](O)[C@]31C InChI=1S/C24H40O6/c1-23-9-8-17-22(16(23)7-6-15(23)18(26)4-3-5-21(29)30)19(27)11-13-10-14(25)12-20(28)24(13,17)2/h13-20,22,25-28H,3-12H2,1-2H3,(H,29,30)/t13?,14-,15?,16?,17?,18+,19-,20+,22?,23+,24-/m0/s1 TVLHFFLEOSSHFT-QVLZICSDSA-N belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Androgens and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Androstane steroids Aliphatic homopolycyclic compounds 1-hydroxysteroids 3-alpha-hydroxysteroids 7-alpha-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 1-hydroxysteroid 20-hydroxysteroid 3-alpha-hydroxysteroid 3-hydroxysteroid 7-alpha-hydroxysteroid 7-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Androgen-skeleton 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 Solid logp 1.42 ALOGPS logs -3.25 ALOGPS solubility 2.41e-01 g/l ALOGPS logp 1.26 ChemAxon pka_strongest_acidic 4.61 ChemAxon pka_strongest_basic -0.3 ChemAxon iupac (5R)-5-hydroxy-5-[(2S,3R,5S,9S,15S)-3,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid ChemAxon average_mass 424.5708 ChemAxon mono_mass 424.282489012 ChemAxon smiles C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(O)=O)[C@@H](O)CC1C[C@H](O)C[C@@H](O)[C@]31C ChemAxon formula C24H40O6 ChemAxon inchi InChI=1S/C24H40O6/c1-23-9-8-17-22(16(23)7-6-15(23)18(26)4-3-5-21(29)30)19(27)11-13-10-14(25)12-20(28)24(13,17)2/h13-20,22,25-28H,3-12H2,1-2H3,(H,29,30)/t13?,14-,15?,16?,17?,18+,19-,20+,22?,23+,24-/m0/s1 ChemAxon inchikey TVLHFFLEOSSHFT-QVLZICSDSA-N ChemAxon polar_surface_area 118.22 ChemAxon refractivity 112.39 ChemAxon polarizability 48.69 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 24088 Specdb::CMs 40072 Specdb::CMs 160569 Specdb::MsMs 319366 Specdb::MsMs 319367 Specdb::MsMs 319368 Specdb::MsMs 366460 Specdb::MsMs 366461 Specdb::MsMs 366462 Specdb::MsMs 2666335 Specdb::MsMs 2666336 Specdb::MsMs 2666337 Specdb::MsMs 3013013 Specdb::MsMs 3013014 Specdb::MsMs 3013015 HMDB13158 #<Reference:0x000055ce3238b0e8> #<Reference:0x000055ce3238af30> #<Reference:0x000055ce3238ad78> #<Reference:0x000055ce3238abc0>