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Record Information
Version1.0
Creation Date2016-09-30 22:38:14 UTC
Update Date2020-05-11 20:09:24 UTC
BMDB IDBMDB0000896
Secondary Accession Numbers
  • BMDB00896
Metabolite Identification
Common NameTaurodeoxycholic acid
DescriptionTaurodeoxycholic acid, also known as taurodeoxycholate or acid, taurodeoxycholic, 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. Taurodeoxycholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
ValueSource
TaurodeoxycholateChEBI
Acid, taurodeoxycholicHMDB
Deoxycholate, taurineHMDB
Sodium taurodeoxycholateHMDB
Taurine deoxycholateHMDB
DeoxycholyltaurineHMDB
Taurodeoxycholate, sodiumHMDB
DeoxytaurocholateHMDB
Deoxytaurocholic acidHMDB
N-(3a,12a-Dihydroxy-5b-cholan-24-oyl)-taurineHMDB
Sodium taurodeoxylateHMDB
Taurodeoxycholic acid sodium saltHMDB
Taurodeoxycholic acid sodium salt hydrateHMDB
TaurodesoxycholateHMDB
Taurodesoxycholic acidHMDB
TudcabilHMDB
Chemical FormulaC26H45NO6S
Average Molecular Weight499.704
Monoisotopic Molecular Weight499.296758867
IUPAC Name2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[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,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid
CAS Registry Number516-50-7
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O
InChI Identifier
InChI=1S/C26H45NO6S/c1-16(4-9-24(30)27-12-13-34(31,32)33)20-7-8-21-19-6-5-17-14-18(28)10-11-25(17,2)22(19)15-23(29)26(20,21)3/h16-23,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,23+,25+,26-/m1/s1
InChI KeyAWDRATDZQPNJFN-VAYUFCLWSA-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
  • Dihydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • Fatty amide
  • Fatty acyl
  • N-acyl-amine
  • Cyclic alcohol
  • Alkanesulfonic acid
  • Sulfonyl
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Organosulfonic acid
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point204 - 208 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility41 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.19ALOGPS
logP1.14ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)-0.75ChemAxon
pKa (Strongest Basic)-0.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area123.93 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity130.6 m³·mol⁻¹ChemAxon
Polarizability56.55 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, Positivesplash10-00lu-0111900000-a90e31e3c4cf2f0c6f3aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-4201229000-01b8d5e2d286a6e403aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0ikd-0047930000-8f9f65d8c1d3c8253501View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03g0-0950300000-d3a559bd8c5ccd049d7bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9545740000-d9a7750b1b579bd2bb05View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0a4i-0009500000-11f56619a58a7f9fe2dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01si-0302920000-c2629184642c876303acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-1904400000-52b97ee82fecb26d2df7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-8906300000-1c0dd8ea92d737243ce2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-2001900000-5090bd6cae3b061c80e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-7504900000-0d93eba8b9f15618357fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-9202000000-2e68ed7e43eb97ec4ad8View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Intestine
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
IntestineExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Abnormal (male calves/vaccination biomarker)
details
HMDB IDHMDB0000896
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022304
KNApSAcK IDNot Available
Chemspider ID2015539
KEGG Compound IDC05463
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTaurodeoxycholic_acid
METLIN ID5853
PubChem Compound2733768
PDB IDNot Available
ChEBI ID9410
References
Synthesis ReferenceParenti, Massimo. Preparation of tauroursodesoxycholic acid dihydrate. Eur. Pat. Appl. (1990), 3 pp. CODEN: EPXXDW EP 400695 A2 19901205 CAN 114:82269 AN 1991:82269
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available