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Showing Compound Lithocholyltaurine (FDB022203)

Record Information
Version1.0
Creation date2011-09-21 00:10:02 UTC
Update date2015-07-21 06:57:03 UTC
Primary IDFDB022203
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLithocholyltaurine
DescriptionLithocholyltaurine is a bile salt formed in the liver from lithocholic acid conjugation with taurine, usually as the sodium salt. It solubilizes fats for absorption and is itself absorbed. Lithocholic acid, a hydrophobic secondary bile acid, is well known to cause intrahepatic cholestasis. There have been extensive studies on the mechanisms of lithocholate-induced cholestasis in animals. Lithocholate diminishes both the bile acid-dependent and independent bile flow. In humans, elevated levels of lithocholic acid are found in patients with chronic cholestatic liver disease. Lithocholyltaurine impairs both the bile canalicular contractions and the canalicular bile secretion, possibly by acting directly on the canalicular membranes in lithocholyltaurine-induced cholestasis. Lithocholyltaurine induce acute cholestasis-associated with retrieval of the bile salt export pump. The bile salt export pump (BSEP) of hepatocyte secretes conjugated bile salts across the canalicular membrane in an ATP-dependent manner. Hepatic retention of bile acids may lead to liver injury by hepatocyte apoptosis and eventually deterioration of cholestatic liver diseases. One mechanism of induced apoptosis by lithocholyltaurine is the induction of transcriptional activity of AP-1 (activation protein-1). (PMID: 16981261, 15763547, 16332456, 18164257) [HMDB]
CAS Number516-90-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-[(3alpha-Hydroxy-24-oxo-5beta-cholan-24-yl)amino]ethanesulfonic acidHMDB
2-[[(3a,5b)-3-Hydroxy-24-oxocholan-24-yl]amino]-ethanesulfonateHMDB
2-[[(3a,5b)-3-Hydroxy-24-oxocholan-24-yl]amino]-ethanesulfonic acidHMDB
3a-Hydroxy-5b-cholanoyltaurineHMDB
3a-Hydroxy-N-(2-sulfoethyl)-5b-cholan-24-amideHMDB
Cholane ethanesulfonic acid deriv.HMDB
Lithocholic acid taurine conjugateHMDB
Lithocholic acid taurine conjugic acidHMDB
N-(3a-Hydroxy-5b-cholan-24-oyl)-taurineHMDB
TaurolithocholateHMDB
Taurolithocholic acidHMDB
Lithocholate, taurineHMDB
Taurine lithocholateHMDB
Taurolithocholic acid, monosodium saltHMDB
Acid, taurolithocholicHMDB
2-[(3alpha-hydroxy-24-oxo-5beta-cholan-24-yl)amino]ethanesulfonic acidhmdb
2-[[(3a,5b)-3-hydroxy-24-oxocholan-24-yl]amino]-Ethanesulfonatehmdb
2-[[(3a,5b)-3-hydroxy-24-oxocholan-24-yl]amino]-Ethanesulfonic acidhmdb
N-(3a-hydroxy-5b-cholan-24-oyl)-Taurinehmdb
taurolithocholatehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.00028 g/LALOGPS
logP2.1ALOGPS
logP2.48ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)-0.63ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.7 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity129.09 m³·mol⁻¹ChemAxon
Polarizability55.73 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC26H45NO5S
IUPAC name2-[(4R)-4-[(2S,5R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid
InChI IdentifierInChI=1S/C26H45NO5S/c1-17(4-9-24(29)27-14-15-33(30,31)32)21-7-8-22-20-6-5-18-16-19(28)10-12-25(18,2)23(20)11-13-26(21,22)3/h17-23,28H,4-16H2,1-3H3,(H,27,29)(H,30,31,32)/t17-,18?,19-,20?,21?,22?,23?,25+,26-/m1/s1
InChI KeyQBYUNVOYXHFVKC-LVMSMGIASA-N
Isomeric SMILESC[C@H](CCC(=O)NCCS(O)(=O)=O)C1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C
Average Molecular Weight483.704
Monoisotopic Molecular Weight483.301844245
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
  • Hydroxy bile acid, alcohol, or derivatives
  • Monohydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Sulfonyl
  • Organosulfonic acid
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Alkanesulfonic acid
  • Cyclic alcohol
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
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-MSLithocholyltaurine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-1029-1111900000-9b7720684db0a5d665e3Spectrum
Predicted GC-MSLithocholyltaurine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fu-4112690000-5f7dbb7d5419abf2ba4aSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-0901700000-054992ad8ced4d2f3e442016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2901100000-a9230c3cb18f164ca9192016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9713000000-2fe3be6a01ea90da17332016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2002900000-5755bbe6c2787d148d0d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-7507900000-f3a3e3647094386df7ad2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9101000000-810d7b96472bf28ac7392016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC02592
Pubchem Compound ID53477716
Pubchem Substance IDNot Available
ChEBI ID36259
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00722
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
Pathways
NameSMPDB LinkKEGG Link
Bile Acid BiosynthesisSMP00035 map00120
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference