1.0 2011-09-21 00:23:14 UTC 2015-07-21 06:57:28 UTC FDB023011 Taurochenodeoxycholate-3-sulfate Taurochenodeoxycholate-3-sulfate is a bile salt formed in the liver by conjugation of chenodeoxycholate with taurine, usually as the sodium salt. 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] Taurochenodeoxycholic acid 3-sulfate Taurochenodeoxycholic acid 3-sulphate Taurochenodeoxycholic acid 3a-sulfate Taurochenodeoxycholic acid 3a-sulphate C26H45NO9S2 579.767 579.253573423 (1S,2S,5R,7R,9R,10R,11S,14R,15R,16R)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-4-[(2-sulfoethyl)carbamoyl]butan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5-sulfonic acid (1S,2S,5R,7R,9R,10R,11S,14R,15R,16R)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-4-[(2-sulfoethyl)carbamoyl]butan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5-sulfonic acid 67030-59-5 [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])C[C@@H](O)[C@]12C)S(O)(=O)=O)[C@H](C)CCC(=O)NCCS(O)(=O)=O InChI=1S/C26H45NO9S2/c1-15(4-7-23(30)27-10-11-37(31,32)33)18-5-6-19-24-20(14-22(29)26(18,19)3)25(2)9-8-17(38(34,35)36)12-16(25)13-21(24)28/h15-22,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32,33)(H,34,35,36)/t15-,16+,17-,18-,19+,20+,21-,22-,24+,25+,26-/m1/s1 IJHJZQKOSUFQCX-WZJRQFJBSA-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 7-hydroxysteroids Alkanesulfonic acids Carbonyl compounds Cyclic alcohols and derivatives Dihydroxy bile acids, alcohols and derivatives Hydrocarbon derivatives N-acyl amines Organic oxides Organonitrogen compounds Organopnictogen compounds Organosulfonic acids Secondary alcohols Secondary carboxylic acid amides Sulfonyls 12-hydroxysteroid 7-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Alkanesulfonic acid Carbonyl group Carboxamide group Carboxylic acid derivative Cyclic alcohol Dihydroxy bile acid, alcohol, or derivatives 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 Secondary alcohol Secondary carboxylic acid amide Sulfonyl Taurinated bile acid Solid logp -0.86 ALOGPS logs -3.61 ALOGPS solubility 1.41e-01 g/l ALOGPS logp -1.5 ChemAxon pka_strongest_acidic -1.3 ChemAxon pka_strongest_basic 0.31 ChemAxon iupac (1S,2S,5R,7R,9R,10R,11S,14R,15R,16R)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-4-[(2-sulfoethyl)carbamoyl]butan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5-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](O)C[C@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])C[C@@H](O)[C@]12C)S(O)(=O)=O)[C@H](C)CCC(=O)NCCS(O)(=O)=O ChemAxon formula C26H45NO9S2 ChemAxon inchi InChI=1S/C26H45NO9S2/c1-15(4-7-23(30)27-10-11-37(31,32)33)18-5-6-19-24-20(14-22(29)26(18,19)3)25(2)9-8-17(38(34,35)36)12-16(25)13-21(24)28/h15-22,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32,33)(H,34,35,36)/t15-,16+,17-,18-,19+,20+,21-,22-,24+,25+,26-/m1/s1 ChemAxon inchikey IJHJZQKOSUFQCX-WZJRQFJBSA-N ChemAxon polar_surface_area 178.3 ChemAxon refractivity 140.71 ChemAxon polarizability 61.32 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 122578 Specdb::NmrOneD 122579 Specdb::NmrOneD 122580 Specdb::NmrOneD 122581 Specdb::NmrOneD 122582 Specdb::NmrOneD 122583 Specdb::NmrOneD 122584 Specdb::NmrOneD 122585 Specdb::NmrOneD 122586 Specdb::NmrOneD 122587 Specdb::NmrOneD 122588 Specdb::NmrOneD 122589 Specdb::NmrOneD 122590 Specdb::NmrOneD 122591 Specdb::NmrOneD 122592 Specdb::NmrOneD 122593 Specdb::NmrOneD 122594 Specdb::NmrOneD 122595 Specdb::NmrOneD 122596 Specdb::NmrOneD 122597 Specdb::CMs 9533 Specdb::CMs 38427 Specdb::CMs 282528 Specdb::CMs 391840 Specdb::CMs 391841 Specdb::CMs 391842 Specdb::CMs 391843 Specdb::CMs 391844 Specdb::CMs 391845 Specdb::CMs 391846 Specdb::CMs 391847 Specdb::CMs 391848 Specdb::CMs 391849 Specdb::CMs 391850 Specdb::CMs 391851 Specdb::CMs 391852 Specdb::CMs 391853 Specdb::CMs 391854 Specdb::CMs 391855 Specdb::CMs 391856 Specdb::CMs 391857 Specdb::CMs 391858 Specdb::CMs 391859 Specdb::CMs 391860 Specdb::CMs 391861 Specdb::MsMs 287029 Specdb::MsMs 287030 Specdb::MsMs 287031 Specdb::MsMs 325774 Specdb::MsMs 325775 Specdb::MsMs 325776 Specdb::MsMs 2755978 Specdb::MsMs 2755979 Specdb::MsMs 2755980 Specdb::MsMs 2952981 Specdb::MsMs 2952982 Specdb::MsMs 2952983 HMDB02486 #<Reference:0x000055ce32a159b8> #<Reference:0x000055ce32a155f8> #<Reference:0x000055ce32a15238> #<Reference:0x000055ce32a14e78>