Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-03-07 02:49:07 UTC |
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HMDB ID | HMDB0000896 |
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Secondary Accession Numbers | - HMDB0004011
- HMDB00896
- HMDB04011
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Metabolite Identification |
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Common Name | Taurodeoxycholic acid |
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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 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 ). |
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Structure | [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=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 |
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Synonyms | Value | Source |
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Taurodeoxycholate | ChEBI | Acid, taurodeoxycholic | HMDB | Deoxycholate, taurine | HMDB | Sodium taurodeoxycholate | HMDB | Taurine deoxycholate | HMDB | Deoxycholyltaurine | HMDB | Taurodeoxycholate, sodium | HMDB | Deoxytaurocholate | HMDB | Deoxytaurocholic acid | HMDB | N-(3a,12a-Dihydroxy-5b-cholan-24-oyl)-taurine | HMDB | Sodium taurodeoxylate | HMDB | Taurodeoxycholic acid sodium salt | HMDB | Taurodeoxycholic acid sodium salt hydrate | HMDB | Taurodesoxycholate | HMDB | Taurodesoxycholic acid | HMDB | Tudcabil | HMDB |
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Chemical Formula | C26H45NO6S |
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Average Molecular Weight | 499.704 |
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Monoisotopic Molecular Weight | 499.296758867 |
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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 |
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Traditional 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]ethanesulfonic acid |
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CAS Registry Number | 516-50-7 |
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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 |
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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 |
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InChI Key | AWDRATDZQPNJFN-VAYUFCLWSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Bile acids, alcohols and derivatives |
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Direct Parent | Taurinated bile acids and derivatives |
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Alternative Parents | |
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Substituents | - Taurinated bile acid
- Dihydroxy bile acid, alcohol, or derivatives
- Hydroxy bile acid, alcohol, or derivatives
- 3-hydroxysteroid
- 12-hydroxysteroid
- 3-alpha-hydroxysteroid
- Hydroxysteroid
- Fatty amide
- Fatty acyl
- N-acyl-amine
- Cyclic alcohol
- Alkanesulfonic acid
- Sulfonyl
- Organic sulfonic acid or derivatives
- Organosulfonic acid or derivatives
- Organosulfonic acid
- Secondary alcohol
- Secondary carboxylic acid amide
- Carboxamide group
- Carboxylic acid derivative
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organosulfur compound
- Carbonyl group
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 204 - 208 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 41 mg/mL | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Taurodeoxycholic acid,1TMS,isomer #1 | C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C | 4275.2 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,1TMS,isomer #2 | C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C | 4209.0 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,1TMS,isomer #3 | C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C | 4327.9 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,1TMS,isomer #4 | C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C | 4261.9 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,2TMS,isomer #1 | C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C | 4140.3 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,2TMS,isomer #2 | C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C | 4322.3 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,2TMS,isomer #3 | C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C | 4240.1 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,2TMS,isomer #4 | C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C | 4250.7 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,2TMS,isomer #5 | C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C | 4156.1 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,2TMS,isomer #6 | C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C | 4311.1 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,3TMS,isomer #1 | C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C | 4185.6 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,3TMS,isomer #1 | C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C | 4429.9 | Standard non polar | 33892256 | Taurodeoxycholic acid,3TMS,isomer #1 | C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C | 4824.8 | Standard polar | 33892256 | Taurodeoxycholic acid,3TMS,isomer #2 | C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C | 4073.0 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,3TMS,isomer #2 | C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C | 4491.7 | Standard non polar | 33892256 | Taurodeoxycholic acid,3TMS,isomer #2 | C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C | 4889.7 | Standard polar | 33892256 | Taurodeoxycholic acid,3TMS,isomer #3 | C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C | 4256.7 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,3TMS,isomer #3 | C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C | 4504.4 | Standard non polar | 33892256 | Taurodeoxycholic acid,3TMS,isomer #3 | C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C | 4844.2 | Standard polar | 33892256 | Taurodeoxycholic acid,3TMS,isomer #4 | C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C | 4198.5 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,3TMS,isomer #4 | C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C | 4509.3 | Standard non polar | 33892256 | Taurodeoxycholic acid,3TMS,isomer #4 | C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C | 4795.8 | Standard polar | 33892256 | Taurodeoxycholic acid,4TMS,isomer #1 | C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C | 4130.8 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,4TMS,isomer #1 | C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C | 4644.9 | Standard non polar | 33892256 | Taurodeoxycholic acid,4TMS,isomer #1 | C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C | 4650.8 | Standard polar | 33892256 | Taurodeoxycholic acid,1TBDMS,isomer #1 | C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C | 4474.7 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,1TBDMS,isomer #2 | C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C | 4401.0 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,1TBDMS,isomer #3 | C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C | 4513.4 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,1TBDMS,isomer #4 | C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C | 4517.3 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,2TBDMS,isomer #1 | C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C | 4529.5 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,2TBDMS,isomer #2 | C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C | 4736.8 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,2TBDMS,isomer #3 | C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C | 4686.8 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,2TBDMS,isomer #4 | C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C | 4640.9 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,2TBDMS,isomer #5 | C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C | 4601.5 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,2TBDMS,isomer #6 | C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C | 4755.6 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,3TBDMS,isomer #1 | C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C | 4759.7 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,3TBDMS,isomer #1 | C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C | 5209.0 | Standard non polar | 33892256 | Taurodeoxycholic acid,3TBDMS,isomer #1 | C[C@H](CCC(=O)NCCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C | 4920.1 | Standard polar | 33892256 | Taurodeoxycholic acid,3TBDMS,isomer #2 | C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C | 4738.3 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,3TBDMS,isomer #2 | C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C | 5216.7 | Standard non polar | 33892256 | Taurodeoxycholic acid,3TBDMS,isomer #2 | C[C@H](CCC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C | 4988.9 | Standard polar | 33892256 | Taurodeoxycholic acid,3TBDMS,isomer #3 | C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C | 4907.7 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,3TBDMS,isomer #3 | C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C | 5277.7 | Standard non polar | 33892256 | Taurodeoxycholic acid,3TBDMS,isomer #3 | C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C | 4948.3 | Standard polar | 33892256 | Taurodeoxycholic acid,3TBDMS,isomer #4 | C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C | 4851.3 | Semi standard non polar | 33892256 | Taurodeoxycholic acid,3TBDMS,isomer #4 | C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C | 5288.8 | Standard non polar | 33892256 | Taurodeoxycholic acid,3TBDMS,isomer #4 | C[C@H](CCC(=O)N(CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C | 4907.6 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-00lu-0111900000-a90e31e3c4cf2f0c6f3a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (2 TMS) - 70eV, Positive | splash10-004i-4201229000-01b8d5e2d286a6e403aa | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (TMS_1_4) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (TMS_2_4) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (TMS_2_5) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (TMS_2_6) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (TBDMS_1_4) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (TBDMS_2_4) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (TBDMS_2_5) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Taurodeoxycholic acid GC-MS (TBDMS_2_6) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Taurodeoxycholic acid Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-0ikd-0047930000-8f9f65d8c1d3c8253501 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Taurodeoxycholic acid Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-03g0-0950300000-d3a559bd8c5ccd049d7b | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Taurodeoxycholic acid Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-001i-9545740000-d9a7750b1b579bd2bb05 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Taurodeoxycholic acid LC-ESI-IT , negative-QTOF | splash10-0a4i-0009500000-11f56619a58a7f9fe2df | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Taurodeoxycholic acid 10V, Positive-QTOF | splash10-0udi-0000690000-02978b9c502ebd7d68d6 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Taurodeoxycholic acid 20V, Positive-QTOF | splash10-03di-0000900000-c7214ee029f71204bb8f | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Taurodeoxycholic acid 40V, Positive-QTOF | splash10-0470-1596200000-357f5937f8ae2d422ba2 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Taurodeoxycholic acid 40V, Positive-QTOF | splash10-0470-1596200000-078d7c7763da8bb11d2e | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Taurodeoxycholic acid 10V, Positive-QTOF | splash10-01si-0302920000-c2629184642c876303ac | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Taurodeoxycholic acid 20V, Positive-QTOF | splash10-0a6r-1904400000-52b97ee82fecb26d2df7 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Taurodeoxycholic acid 40V, Positive-QTOF | splash10-004l-8906300000-1c0dd8ea92d737243ce2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Taurodeoxycholic acid 10V, Negative-QTOF | splash10-000t-2001900000-5090bd6cae3b061c80e4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Taurodeoxycholic acid 20V, Negative-QTOF | splash10-0089-7504900000-0d93eba8b9f15618357f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Taurodeoxycholic acid 40V, Negative-QTOF | splash10-001l-9202000000-2e68ed7e43eb97ec4ad8 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Taurodeoxycholic acid 10V, Negative-QTOF | splash10-0002-0000900000-31f17d1d48b7afdf3bae | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Taurodeoxycholic acid 20V, Negative-QTOF | splash10-0002-0000900000-09a127bb8eacbd0a6ab7 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Taurodeoxycholic acid 40V, Negative-QTOF | splash10-001j-9201800000-97168e49aaa085a3735c | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Taurodeoxycholic acid 10V, Positive-QTOF | splash10-0f89-0000950000-e77d9cab9a8afc22e8b1 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Taurodeoxycholic acid 20V, Positive-QTOF | splash10-08gi-2414910000-42610292496f161b3e8d | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Taurodeoxycholic acid 40V, Positive-QTOF | splash10-052e-8912000000-fd93247f3ff2a43d83dd | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
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Disease References | Hepatocellular carcinoma |
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- Ressom HW, Xiao JF, Tuli L, Varghese RS, Zhou B, Tsai TH, Ranjbar MR, Zhao Y, Wang J, Di Poto C, Cheema AK, Tadesse MG, Goldman R, Shetty K: Utilization of metabolomics to identify serum biomarkers for hepatocellular carcinoma in patients with liver cirrhosis. Anal Chim Acta. 2012 Sep 19;743:90-100. doi: 10.1016/j.aca.2012.07.013. Epub 2012 Jul 20. [PubMed:22882828 ]
| Cirrhosis |
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- Ressom HW, Xiao JF, Tuli L, Varghese RS, Zhou B, Tsai TH, Ranjbar MR, Zhao Y, Wang J, Di Poto C, Cheema AK, Tadesse MG, Goldman R, Shetty K: Utilization of metabolomics to identify serum biomarkers for hepatocellular carcinoma in patients with liver cirrhosis. Anal Chim Acta. 2012 Sep 19;743:90-100. doi: 10.1016/j.aca.2012.07.013. Epub 2012 Jul 20. [PubMed:22882828 ]
| Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
| Metastatic melanoma |
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- Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]
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- Xie Q, Li GM, Zhou XQ, Liao D, Yu H, Guo Q: [Effect of Tauroursodeoxycholic acid on cytochrome C-mediated apoptosis in HepG2 cells]. Zhonghua Gan Zang Bing Za Zhi. 2003 May;11(5):298-301. [PubMed:12773247 ]
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- Xu Y, Yang L, Zhao S, Wang Z: Large-scale production of tauroursodeoxycholic acid products through fermentation optimization of engineered Escherichia coli cell factory. Microb Cell Fact. 2019 Feb 8;18(1):34. doi: 10.1186/s12934-019-1076-2. [PubMed:30736766 ]
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