Taurolithocholic acid 3-sulfate (CHEM022769)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:51:29 UTC
Update Date2016-11-09 01:17:34 UTC
Accession NumberCHEM022769
Identification
Common NameTaurolithocholic acid 3-sulfate
ClassSmall Molecule
DescriptionThe steroid sulfate of taurolithocholic acid.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass563.767 g/mol
Monoisotopic Mass563.259 g/mol
CAS Registry Number15324-65-9
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
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 IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000590000-1b81180dda2f5166dc7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0219500000-ec90bdc61d5b63c6bb94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-4279200000-8776b4d5f63c61813c12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000090000-baf7d898c278a1ba0a12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ot-9000050000-c8bf230c02d78676120cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01qa-9000030000-78391f8c8560da71030eSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002580
FooDB IDFDB023028
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDTAUROLITHOCHOLATE-SULFATE
METLIN ID6716
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID389078
ChEBI ID17864
PubChem Compound ID440071
Kegg Compound IDC03642
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24177139
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=8437507
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=871063
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=894140
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. 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.