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Record Information
Version3.6
Creation Date2006-05-22 14:17:57 UTC
Update Date2016-02-11 01:05:43 UTC
HMDB IDHMDB02580
Secondary Accession NumbersNone
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 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 ).
Structure
Thumb
Synonyms
ValueSource
(3alpha-Sulfato-5beta-cholan-24-oyl)-2'-aminoethanesulfonateChEBI
3alpha-SulfatolithocholyltaurineChEBI
SLCT-3-SulfateChEBI
Taurolithocholate sulfateChEBI
Taurolithocholic acid 3-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
SLCT-3-SulphateHMDB
Taurolithocholate 3-sulfateHMDB
Taurolithocholate 3-sulphateHMDB
Taurolithocholate sulphateHMDB
Taurolithocholic acid 3-sulphateHMDB
Taurolithocholic acid sulfateHMDB
Taurolithocholic acid sulphateHMDB
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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid
Traditional Nametlc-S
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 KeyInChIKey=HSNPMXROZIQAQD-GBURMNQMSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • 3-sulfated steroid
  • Sulfated steroid skeleton
  • Sulfuric acid monoester
  • Fatty acyl
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • N-acyl-amine
  • Fatty amide
  • Alkanesulfonic acid
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonic acid
  • Organic sulfuric acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
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 mg/mLALOGPS
logP-0.12ALOGPS
logP0.95ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)-1.5ChemAxon
pKa (Strongest Basic)0.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area147.07 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity139.08 m3·mol-1ChemAxon
Polarizability61.44 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Feces
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified0.77 +/- 0.63 nmol/g of fecesNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023028
KNApSAcK IDNot Available
Chemspider ID389078
KEGG Compound IDC03642
BioCyc IDTAUROLITHOCHOLATE-SULFATE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02580
Metagene LinkHMDB02580
METLIN ID6716
PubChem Compound440071
PDB IDNot Available
ChEBI ID17864
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [12523936 ]
  2. 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. [10103175 ]
  3. 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. [16332456 ]
  4. 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. [15664251 ]
  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. [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. [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. [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. [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