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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:57 UTC
Update Date2020-02-26 21:24:12 UTC
HMDB IDHMDB0002580
Secondary Accession Numbers
  • HMDB02580
Metabolite Identification
Common NameTaurolithocholic acid 3-sulfate
DescriptionTaurolithocholic acid 3-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 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 ).
Structure
Data?1582752252
Synonyms
ValueSource
(3alpha-Sulfato-5beta-cholan-24-oyl)-2'-aminoethanesulfonateChEBI
3alpha-SulfatolithocholyltaurineChEBI
SLCT-3-SulfateChEBI
Taurolithocholate 3-sulfateChEBI
Taurolithocholate sulfateChEBI
TLC-SChEBI
(3a-Sulfato-5b-cholan-24-oyl)-2'-aminoethanesulfonateGenerator
(3a-Sulfato-5b-cholan-24-oyl)-2'-aminoethanesulfonic acidGenerator
(3a-Sulphato-5b-cholan-24-oyl)-2'-aminoethanesulphonateGenerator
(3a-Sulphato-5b-cholan-24-oyl)-2'-aminoethanesulphonic acidGenerator
(3alpha-Sulfato-5beta-cholan-24-oyl)-2'-aminoethanesulfonic acidGenerator
(3alpha-Sulphato-5beta-cholan-24-oyl)-2'-aminoethanesulphonateGenerator
(3alpha-Sulphato-5beta-cholan-24-oyl)-2'-aminoethanesulphonic acidGenerator
(3Α-sulfato-5β-cholan-24-oyl)-2'-aminoethanesulfonateGenerator
(3Α-sulfato-5β-cholan-24-oyl)-2'-aminoethanesulfonic acidGenerator
(3Α-sulphato-5β-cholan-24-oyl)-2'-aminoethanesulphonateGenerator
(3Α-sulphato-5β-cholan-24-oyl)-2'-aminoethanesulphonic acidGenerator
3a-SulfatolithocholyltaurineGenerator
3a-SulphatolithocholyltaurineGenerator
3alpha-SulphatolithocholyltaurineGenerator
3Α-sulfatolithocholyltaurineGenerator
3Α-sulphatolithocholyltaurineGenerator
SLCT-3-Sulfuric acidGenerator
SLCT-3-SulphateGenerator
SLCT-3-Sulphuric acidGenerator
Taurolithocholate 3-sulphateGenerator
Taurolithocholic acid 3-sulfuric acidGenerator
Taurolithocholic acid 3-sulphuric acidGenerator
Taurolithocholate sulphateGenerator
Taurolithocholic acid sulfuric acidGenerator
Taurolithocholic acid sulphuric acidGenerator
Taurolithocholic acid 3-sulphateHMDB
Taurolithocholic acid sulfateHMDB
Taurolithocholic acid sulphateHMDB
Taurolithocholic acid 3-sulfateChEBI
Chemical FormulaC26H45NO8S2
Average Molecular Weight563.767
Monoisotopic Molecular Weight563.258658801
IUPAC Name2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[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)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid
CAS Registry Number15324-65-9
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@H](C)CCC(=O)NCCS(O)(=O)=O
InChI Identifier
InChI=1S/C26H45NO8S2/c1-17(4-9-24(28)27-14-15-36(29,30)31)21-7-8-22-20-6-5-18-16-19(35-37(32,33)34)10-12-25(18,2)23(20)11-13-26(21,22)3/h17-23H,4-16H2,1-3H3,(H,27,28)(H,29,30,31)(H,32,33,34)/t17-,18-,19-,20+,21-,22+,23+,25+,26-/m1/s1
InChI KeyHSNPMXROZIQAQD-GBURMNQMSA-N
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTaurinated bile acids and derivatives
Alternative Parents
Substituents
  • Taurinated bile acid
  • Sulfated steroid skeleton
  • Fatty amide
  • N-acyl-amine
  • Sulfuric acid monoester
  • Sulfate-ester
  • Fatty acyl
  • Sulfuric acid ester
  • Alkyl sulfate
  • Organic sulfuric acid or derivatives
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Organosulfonic acid
  • Sulfonyl
  • Alkanesulfonic acid
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Carbonyl group
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0014 g/LALOGPS
logP-0.12ALOGPS
logP1.24ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)-1.6ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area147.07 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity139.08 m³·mol⁻¹ChemAxon
Polarizability61.47 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001s-0122960000-7322e2c8b4da02bf9e0aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0000900000-4d1082945d64455a6eabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900340000-82769bc714a44b90e5d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900200000-44fc18bc9bafc7c398f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-7911100000-5bfee268d4d671bbc025Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3100490000-7c2e69684854500bbe5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-5201920000-f65c49dc30c74c2b1eb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0089-9303100000-f4bac240298f8ba5004fSpectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified0.77 +/- 0.63 nmol/g dry fecesNot SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023028
KNApSAcK IDNot Available
Chemspider ID389078
KEGG Compound IDC03642
BioCyc IDTAUROLITHOCHOLATE-SULFATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6716
PubChem Compound440071
PDB IDNot Available
ChEBI ID17864
Food Biomarker OntologyNot Available
VMH IDHC02198
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Herold BC, Kirkpatrick R, Marcellino D, Travelstead A, Pilipenko V, Krasa H, Bremer J, Dong LJ, Cooper MD: Bile salts: natural detergents for the prevention of sexually transmitted diseases. Antimicrob Agents Chemother. 1999 Apr;43(4):745-51. [PubMed:10103175 ]
  2. Hayashi H, Takada T, Suzuki H, Onuki R, Hofmann AF, Sugiyama Y: Transport by vesicles of glycine- and taurine-conjugated bile salts and taurolithocholate 3-sulfate: a comparison of human BSEP with rat Bsep. Biochim Biophys Acta. 2005 Dec 30;1738(1-3):54-62. Epub 2005 Nov 15. [PubMed:16332456 ]
  3. Boucherie S, Koukoui O, Nicolas V, Combettes L: Cholestatic bile acids inhibit gap junction permeability in rat hepatocyte couplets and normal rat cholangiocytes. J Hepatol. 2005 Feb;42(2):244-51. [PubMed:15664251 ]
  4. Zelcer N, Reid G, Wielinga P, Kuil A, van der Heijden I, Schuetz JD, Borst P: Steroid and bile acid conjugates are substrates of human multidrug-resistance protein (MRP) 4 (ATP-binding cassette C4). Biochem J. 2003 Apr 15;371(Pt 2):361-7. [PubMed:12523936 ]
  5. St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. [PubMed:11316487 ]
  6. Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. [PubMed:16037564 ]
  7. Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. [PubMed:12576301 ]
  8. Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
Gene Name:
SULT2A1
Uniprot ID:
Q06520
Molecular weight:
33779.57
Reactions
Phosphoadenosine phosphosulfate + Lithocholyltaurine → Adenosine 3',5'-diphosphate + Taurolithocholic acid 3-sulfatedetails