FComEx: Taurodeoxycholic acid (PC000460)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:48 UTC

Update date

2017-01-19 02:36:24 UTC

FoodComEx ID

PC000460

FoodDB Record

FDB022304

Chemical Information

Name

Taurodeoxycholic acid

Description

Taurodeoxycholic 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 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]

CAS Number

516-50-7

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Deoxycholyltaurine	hmdb
Deoxytaurocholate	hmdb
Deoxytaurocholic acid	hmdb
N-(3a,12a-dihydroxy-5b-cholan-24-oyl)-Taurine	hmdb
Sodium taurodeoxycholate	hmdb
Sodium taurodeoxylate	hmdb
Taurodeoxycholate	ChEBI
Taurodeoxycholic acid	hmdb
Taurodeoxycholic acid sodium salt	hmdb
Taurodeoxycholic acid sodium salt hydrate	hmdb
Taurodesoxycholate	hmdb
Taurodesoxycholic acid	hmdb
Tudcabil	hmdb

Chemical Formula

C26H45NO6S

IUPAC name

2-[(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

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 Key

AWDRATDZQPNJFN-VAYUFCLWSA-N

Isomeric 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

Average Molecular Weight

499.704

Monoisotopic Molecular Weight

499.296758867

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Taurinated bile acids and derivatives

Alternative Parents