1.0 2011-09-21 00:23:18 UTC 2015-07-21 06:57:28 UTC FDB023016 Taurochenodeoxycholate-7-sulfate Taurochenodeoxycholate-7-sulfate is a sulfated bile acid. Under normal circumstances, bile acid sulfation is a minor pathway. However in the presence of cholestasis, the fraction of the bile acid pool which is sulfated increases. Sulfation of bile acids increases the aqueous solubility of the amphipathic compounds and results in more efficient renal clearance as well as in decreased reabsorption from the intestinal lumen. 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] 2-(((3alpha,5beta,7alpha)-3-hydroxy-24-oxo-7-(sulfooxy)cholan-24-yl)amino)-Ethanesulfonic acid Taurochenodeoxycholate-7-sulfate Taurochenodeoxycholate-7-sulphate TCDC-7-s C26H45NO9S2 579.767 579.253573423 2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-9-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid 2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-9-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethanesulfonic acid 66874-12-2 [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@H](C)CCC(=O)NCCS(O)(=O)=O InChI=1S/C26H45NO9S2/c1-16(4-7-23(29)27-12-13-37(30,31)32)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)36-38(33,34)35/h16-22,24,28H,4-15H2,1-3H3,(H,27,29)(H,30,31,32)(H,33,34,35)/t16-,17+,18-,19-,20+,21+,22-,24+,25+,26-/m1/s1 WTKQKSAFONWCMW-BJLOMENOSA-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 3-alpha-hydroxysteroids Alkanesulfonic acids Alkyl sulfates Carbonyl compounds Cyclic alcohols and derivatives Hydrocarbon derivatives Monohydroxy bile acids, alcohols and derivatives N-acyl amines Organic oxides Organonitrogen compounds Organopnictogen compounds Organosulfonic acids Secondary alcohols Secondary carboxylic acid amides Sulfated steroids Sulfonyls Sulfuric acid monoesters 3-alpha-hydroxysteroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Alkanesulfonic acid Alkyl sulfate Carbonyl group Carboxamide group Carboxylic acid derivative Cyclic alcohol Fatty acyl Fatty amide Hydrocarbon derivative Hydroxy bile acid, alcohol, or derivatives Hydroxysteroid Monohydroxy bile acid, alcohol, or derivatives N-acyl-amine Organic nitrogen compound Organic oxide Organic oxygen compound Organic sulfonic acid or derivatives Organic sulfuric acid or derivatives Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfonic acid Organosulfonic acid or derivatives Organosulfur compound Secondary alcohol Secondary carboxylic acid amide Sulfate-ester Sulfated steroid skeleton Sulfonyl Sulfuric acid ester Sulfuric acid monoester Taurinated bile acid Sulfates Solid logp -0.61 ALOGPS logs -4.63 ALOGPS solubility 1.37e-02 g/l ALOGPS logp -0.18 ChemAxon pka_strongest_acidic -1.2 ChemAxon pka_strongest_basic 0.13 ChemAxon iupac 2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-9-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid ChemAxon average_mass 579.767 ChemAxon mono_mass 579.253573423 ChemAxon smiles [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@H](C)CCC(=O)NCCS(O)(=O)=O ChemAxon formula C26H45NO9S2 ChemAxon inchi InChI=1S/C26H45NO9S2/c1-16(4-7-23(29)27-12-13-37(30,31)32)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)36-38(33,34)35/h16-22,24,28H,4-15H2,1-3H3,(H,27,29)(H,30,31,32)(H,33,34,35)/t16-,17+,18-,19-,20+,21+,22-,24+,25+,26-/m1/s1 ChemAxon inchikey WTKQKSAFONWCMW-BJLOMENOSA-N ChemAxon polar_surface_area 167.3 ChemAxon refractivity 140.67 ChemAxon polarizability 61.86 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 311812 Specdb::MsMs 311813 Specdb::MsMs 311814 Specdb::MsMs 356902 Specdb::MsMs 356903 Specdb::MsMs 356904 Specdb::MsMs 2735732 Specdb::MsMs 2735733 Specdb::MsMs 2735734 Specdb::MsMs 2973318 Specdb::MsMs 2973319 Specdb::MsMs 2973320 Specdb::NmrOneD 122598 Specdb::NmrOneD 122599 Specdb::NmrOneD 122600 Specdb::NmrOneD 122601 Specdb::NmrOneD 122602 Specdb::NmrOneD 122603 Specdb::NmrOneD 122604 Specdb::NmrOneD 122605 Specdb::NmrOneD 122606 Specdb::NmrOneD 122607 Specdb::NmrOneD 122608 Specdb::NmrOneD 122609 Specdb::NmrOneD 122610 Specdb::NmrOneD 122611 Specdb::NmrOneD 122612 Specdb::NmrOneD 122613 Specdb::NmrOneD 122614 Specdb::NmrOneD 122615 Specdb::NmrOneD 122616 Specdb::NmrOneD 122617 Specdb::CMs 20567 Specdb::CMs 38432 Specdb::CMs 282529 Specdb::CMs 391869 Specdb::CMs 391870 Specdb::CMs 391871 Specdb::CMs 391872 Specdb::CMs 391873 Specdb::CMs 391874 Specdb::CMs 391875 HMDB02498 #<Reference:0x000055ce324aa820> #<Reference:0x000055ce324aa668> #<Reference:0x000055ce324aa4b0> #<Reference:0x000055ce324aa2f8> #<Reference:0x000055ce324aa140> 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