1.0 2011-09-21 00:11:57 UTC 2015-10-09 22:30:52 UTC FDB022312 Sulfolithocholic acid 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. (PMID: 11316487, 16037564, 12576301, 11907135) [HMDB] (3a-alpha,5-beta)-3-(sulfooxy)-Cholan-24-oate (3a-alpha,5-beta)-3-(sulfooxy)-Cholan-24-oic acid 3a-Sulfate-5b-cholan-24-oate 3a-Sulfate-5b-cholan-24-oic acid Lithocholic acid 3-alpha-sulfate Lithocholic acid 3-alpha-sulphate Lithocholic acid 3-O-sulfate Lithocholic acid 3-O-sulphate Lithocholic acid 3-sulfate Lithocholic acid 3-sulphate Lithocholic acid 3a-sulfate Lithocholic acid 3a-sulphate Sulfolithocholate Sulfolithocholic acid C24H40O6S 456.636 456.254559702 (4R)-4-[(1S,2S,5R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid (4R)-4-[(1S,2S,5R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid 34669-57-3 [H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@@H](CC[C@]12C)OS(O)(=O)=O InChI=1S/C24H40O6S/c1-15(4-9-22(25)26)19-7-8-20-18-6-5-16-14-17(30-31(27,28)29)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21H,4-14H2,1-3H3,(H,25,26)(H,27,28,29)/t15-,16?,17-,18+,19-,20+,21+,23+,24-/m1/s1 AXDXVEYHEODSPN-YPLGJCPNSA-N belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid. Bile acids, alcohols and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Bile acids, alcohols and derivatives Aliphatic homopolycyclic compounds Alkyl sulfates Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Sulfated steroids Sulfuric acid monoesters Aliphatic homopolycyclic compound Alkyl sulfate Bile acid, alcohol, or derivatives Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organic sulfuric acid or derivatives Organooxygen compound Sulfate-ester Sulfated steroid skeleton Sulfuric acid ester Sulfuric acid monoester Solid logp 1.39 ALOGPS logs -5.94 ALOGPS solubility 5.20e-04 g/l ALOGPS logp 5.08 ChemAxon pka_strongest_acidic -1.3 ChemAxon iupac (4R)-4-[(1S,2S,5R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid ChemAxon average_mass 456.636 ChemAxon mono_mass 456.254559702 ChemAxon smiles [H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@@H](CC[C@]12C)OS(O)(=O)=O ChemAxon formula C24H40O6S ChemAxon inchi InChI=1S/C24H40O6S/c1-15(4-9-22(25)26)19-7-8-20-18-6-5-16-14-17(30-31(27,28)29)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21H,4-14H2,1-3H3,(H,25,26)(H,27,28,29)/t15-,16?,17-,18+,19-,20+,21+,23+,24-/m1/s1 ChemAxon inchikey AXDXVEYHEODSPN-YPLGJCPNSA-N ChemAxon polar_surface_area 100.9 ChemAxon refractivity 117.67 ChemAxon polarizability 51.26 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 1540 Specdb::NmrOneD 1599 Specdb::MsMs 98295 Specdb::MsMs 98296 Specdb::MsMs 98297 Specdb::MsMs 163191 Specdb::MsMs 163192 Specdb::MsMs 163193 Specdb::MsMs 2301726 Specdb::MsMs 2301727 Specdb::MsMs 2301728 Specdb::MsMs 3064203 Specdb::MsMs 3064204 Specdb::MsMs 3064205 Specdb::CMs 23510 Specdb::CMs 37836 Specdb::CMs 166780 Specdb::CMs 1081357 Specdb::CMs 1081359 Specdb::CMs 1081361 HMDB00907 35421 #<Reference:0x000055ce3229daf0> #<Reference:0x000055ce3229d938> #<Reference:0x000055ce3229d780> #<Reference:0x000055ce3229d5c8> #<Reference:0x000055ce3229d410> #<Reference:0x000055ce3229d258> #<Reference:0x000055ce3229d0a0> #<Reference:0x000055ce3229cee8> #<Reference:0x000055ce3229cd30> 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