Back to Compounds

Showing Compound Taurolithocholic acid 3-sulfate (FDB023028)

Record Information
Version1.0
Creation date2011-09-21 00:23:31 UTC
Update date2015-07-21 06:57:29 UTC
Primary IDFDB023028
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number15324-65-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(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
(3alpha-sulfato-5beta-cholan-24-oyl)-2'-aminoethanesulfonatehmdb
(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
3α-sulfatolithocholyltaurineGenerator
3α-sulphatolithocholyltaurineGenerator
Slct-3-sulfatehmdb
Slct-3-sulfuric acidGenerator
Slct-3-sulphateGenerator
Slct-3-sulphuric acidGenerator
taurolithocholate 3-sulfatehmdb
Taurolithocholic acid 3-sulfic acidhmdb
taurolithocholic acid sulfatehmdb
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
Chemical FormulaC26H45NO8S2
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
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
Isomeric 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
Average Molecular Weight563.767
Monoisotopic Molecular Weight563.258658801
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSTaurolithocholic acid 3-sulfate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001s-0122960000-7322e2c8b4da02bf9e0aSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0000900000-4d1082945d64455a6eab2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900340000-82769bc714a44b90e5d32016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900200000-44fc18bc9bafc7c398f12016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-7911100000-5bfee268d4d671bbc0252016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3100490000-7c2e69684854500bbe5f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-5201920000-f65c49dc30c74c2b1eb92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0089-9303100000-f4bac240298f8ba5004f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000590000-1b81180dda2f5166dc7f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0219500000-ec90bdc61d5b63c6bb942021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-4279200000-8776b4d5f63c61813c122021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000090000-baf7d898c278a1ba0a122021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ot-9000050000-c8bf230c02d78676120c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01qa-9000030000-78391f8c8560da71030e2021-09-22View Spectrum
NMRNot Available
ChemSpider ID389078
ChEMBL IDCHEMBL270493
KEGG Compound IDC03642
Pubchem Compound ID440071
Pubchem Substance IDNot Available
ChEBI ID17864
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02580
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Bile salt sulfotransferaseSULT2A1Q06520
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference