1.0 2010-04-08 22:10:07 UTC 2015-10-09 22:33:14 UTC FDB012335 Taurocholic acid Emulsifier in foods Taurocholic acid is a bile acid and is the product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. 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); Taurocholic acid, as with all bile acids, acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic (a bile purging agent). Hydrolysis of taurocholic acid yields taurine, a nonessential amino acid.; Taurocholic acid is one of the main components of urinary nonsulfated bile acids in biliary atresia. Raised levels of the bile acid taurocholate in the fetal serum in obstetric cholestasis may result in the development of a fetal dysrhythmia and in sudden intra-uterine death. (PMID: 3944741, 11256973); Taurocholic acid, known also as cholaic acid, cholyltaurine, or acidum cholatauricum, is a deliquescent yellowish crystalline bile acid involved in the emulsification of fats. It occurs as a sodium salt in the bile of mammals. It is a conjugate of cholic acid with taurine. In medical use, it is administered as a cholagogue and choleretic. 3a,7a,12a-Trihydroxy-5b-cholanic acid-24-taurine Bile acid Cholaic acid Cholic acid taurine conjugate Cholyltaurine N-(3,7,12-Trihydroxycholan-24-oyl)taurine N-choloyl-taurine N-choloyltaurine Taurine, n-choloyl- Taurocholate C26H45NO7S 515.703 515.291673489 N-(2-sulfoethyl)-4-{5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanimidic acid N-(2-sulfoethyl)-4-{5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanimidic acid 81-24-3 CC(CCC(=O)NCCS(O)(=O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C InChI=1S/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34) WBWWGRHZICKQGZ-UHFFFAOYSA-N belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety. Taurinated bile acids and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Bile acids, alcohols and derivatives Aliphatic homopolycyclic compounds 12-hydroxysteroids 3-hydroxysteroids 7-hydroxysteroids Alkanesulfonic acids Carbonyl compounds Cyclic alcohols and derivatives Hydrocarbon derivatives N-acyl amines Organic oxides Organonitrogen compounds Organopnictogen compounds Organosulfonic acids Polyols Secondary alcohols Secondary carboxylic acid amides Sulfonyls Trihydroxy bile acids, alcohols and derivatives 12-hydroxysteroid 3-hydroxysteroid 7-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Alkanesulfonic acid Carbonyl group Carboxamide group Carboxylic acid derivative Cyclic alcohol Fatty acyl Fatty amide Hydrocarbon derivative Hydroxy bile acid, alcohol, or derivatives Hydroxysteroid N-acyl-amine Organic nitrogen compound Organic oxide Organic oxygen compound Organic sulfonic acid or derivatives Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfonic acid Organosulfonic acid or derivatives Organosulfur compound Polyol Secondary alcohol Secondary carboxylic acid amide Sulfonyl Taurinated bile acid Trihydroxy bile acid, alcohol, or derivatives Solid logp 1.27 ALOGPS logs -3.66 ALOGPS solubility 1.13e-01 g/l ALOGPS melting_point Mp 125° dec. logp 0.34 ChemAxon pka_strongest_acidic -1.2 ChemAxon pka_strongest_basic 6.05 ChemAxon iupac N-(2-sulfoethyl)-4-{5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanimidic acid ChemAxon average_mass 515.703 ChemAxon mono_mass 515.291673489 ChemAxon smiles CC(CCC(=O)NCCS(O)(=O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C ChemAxon formula C26H45NO7S ChemAxon inchi InChI=1S/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34) ChemAxon inchikey WBWWGRHZICKQGZ-UHFFFAOYSA-N ChemAxon polar_surface_area 147.65 ChemAxon refractivity 132.72 ChemAxon polarizability 57.87 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 8 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Bile Acid Biosynthesis SMP00035 map00120 Specdb::CMs 974499 Specdb::CMs 974500 Specdb::CMs 974501 Specdb::CMs 974502 Specdb::CMs 974503 Specdb::CMs 974504 Specdb::CMs 974505 Specdb::CMs 974506 Specdb::CMs 974507 Specdb::CMs 974508 Specdb::CMs 974509 Specdb::CMs 974510 Specdb::CMs 974511 Specdb::CMs 974512 Specdb::CMs 974513 Specdb::CMs 974514 Specdb::CMs 974515 Specdb::CMs 974516 Specdb::CMs 974517 Specdb::CMs 974518 Specdb::CMs 974519 Specdb::CMs 974520 Specdb::CMs 974521 Specdb::CMs 974522 Specdb::CMs 974523 HMDB00036 28865 1AQL #<Reference:0x000055ce3309ba30> #<Reference:0x000055ce3309b878> #<Reference:0x000055ce3309b698> #<Reference:0x000055ce3309b490> #<Reference:0x000055ce3309b288> #<Reference:0x000055ce3309b0d0> #<Reference:0x000055ce3309af18> #<Reference:0x000055ce3309ad60> #<Reference:0x000055ce3309aba8> #<Reference:0x000055ce3309a9f0> #<Reference:0x000055ce3309a798> #<Reference:0x000055ce3309a590> #<Reference:0x000055ce3309a2e8> #<Reference:0x000055ce3309a090> #<Reference:0x000055ce33099e60> #<Reference:0x000055ce33099ca8> #<Reference:0x000055ce330998c0> #<Reference:0x000055ce330996b8> #<Reference:0x000055ce33099500> #<Reference:0x000055ce33099320> #<Reference:0x000055ce33099118> #<Reference:0x000055ce33098f60> #<Reference:0x000055ce33098d08> #<Reference:0x000055ce33098a10> 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 Bile acid-CoA:amino acid N-acyltransferase Q14032 BAAT