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Record Information
Version1.0
Creation Date2016-09-30 22:35:30 UTC
Update Date2020-05-11 20:09:09 UTC
BMDB IDBMDB0000722
Secondary Accession Numbers
  • BMDB00722
Metabolite Identification
Common NameLithocholyltaurine
DescriptionLithocholyltaurine, also known as taurolithocholate, 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. Lithocholyltaurine is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC26H45NO5S
Average Molecular Weight483.704
Monoisotopic Molecular Weight483.301844245
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
Traditional Name2-[(4R)-4-[(2S,5R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid
CAS Registry Number516-90-5
SMILES
C[C@H](CCC(=O)NCCS(O)(=O)=O)C1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C
InChI Identifier
InChI=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
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
  • 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
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point212 - 213 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-1029-1111900000-9b7720684db0a5d665e3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fu-4112690000-5f7dbb7d5419abf2ba4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-0901700000-054992ad8ced4d2f3e44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2901100000-a9230c3cb18f164ca919View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9713000000-2fe3be6a01ea90da1733View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2002900000-5755bbe6c2787d148d0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-7507900000-f3a3e3647094386df7adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9101000000-810d7b96472bf28ac739View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen Locations
  • Gallbladder
  • Intestine
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
GallbladderExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000722
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022203
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02592
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTaurolithocholic acid
METLIN ID5690
PubChem Compound53477716
PDB IDNot Available
ChEBI ID36259
References
Synthesis ReferenceZhang, Jie; Griffiths, William J.; Bergman, Tomas; Sjoevall, Jan. Derivatization of bile acids with taurine for analysis by fast atom bombardment mass spectrometry with collision-induced fragmentation. Journal of Lipid Research (1993), 34(11), 1895-900.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available