Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:38:17 UTC
Update Date2024-04-30 19:31:15 UTC
Metabolite IDMMDBc0000166
Metabolite Identification
Common NameTaurodeoxycholic acid
DescriptionTaurodeoxycholic acid is a bile salt formed in the liver by conjugation of deoxycholate with taurine, usually as the sodium salt. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the 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 ). Taurodeoxycholic acid can be found in Escherichia (PMID: 30736766 ).
Structure
Synonyms
ValueSource
TaurodeoxycholateChEBI
Acid, taurodeoxycholicHMDB
Deoxycholate, taurineHMDB
Sodium taurodeoxycholateHMDB
Taurine deoxycholateHMDB
DeoxycholyltaurineHMDB
Taurodeoxycholate, sodiumHMDB
DeoxytaurocholateHMDB
Deoxytaurocholic acidHMDB
N-(3a,12a-Dihydroxy-5b-cholan-24-oyl)-taurineHMDB
Sodium taurodeoxylateHMDB
Taurodeoxycholic acid sodium saltHMDB
Taurodeoxycholic acid sodium salt hydrateHMDB
TaurodesoxycholateHMDB
Taurodesoxycholic acidHMDB
TudcabilHMDB
Molecular FormulaC26H45NO6S
Average Mass499.704
Monoisotopic Mass499.296758867
IUPAC Name2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid
Traditional Name2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid
CAS Registry Number516-50-7
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O
InChI Identifier
InChI=1S/C26H45NO6S/c1-16(4-9-24(30)27-12-13-34(31,32)33)20-7-8-21-19-6-5-17-14-18(28)10-11-25(17,2)22(19)15-23(29)26(20,21)3/h16-23,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,23+,25+,26-/m1/s1
InChI KeyAWDRATDZQPNJFN-VAYUFCLWSA-N