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Identification
YMDB IDYMDB00770
Nametaurocholic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionTaurocholic acid, also known as taurocholate or choloyl-taurine, belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. Taurocholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
  • 3a,7a,12a-Trihydroxy-5b-cholanic acid-24-taurine
  • 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanic acid 24-taurine
  • bile acid
  • Cholaic acid
  • Cholic acid taurine conjugate
  • Choloyl-taurine
  • cholyltaurine
  • n-choloyl-Taurine
  • N-Choloyltaurine
  • Taurine, N-choloyl-
  • taurocholate
  • Taurocholic acid
  • 3a,7a,12a-Trihydroxy-5b-cholanate 24-taurine
  • 3a,7a,12a-Trihydroxy-5b-cholanic acid 24-taurine
  • 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanate 24-taurine
  • 3Α,7α,12α-trihydroxy-5β-cholanate 24-taurine
  • 3Α,7α,12α-trihydroxy-5β-cholanic acid 24-taurine
  • Cholate taurine conjugate
  • Cholic acid taurine conjugic acid
  • Cholaate
  • Taurine cholate
  • Taurocholic acid, (7 beta)-isomer
  • Taurocholic acid, (5 alpha)-isomer
CAS number81-24-3
WeightAverage: 515.703
Monoisotopic: 515.291673489
InChI KeyWBWWGRHZICKQGZ-HZAMXZRMSA-N
InChIInChI=1S/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34)/t15-,16+,17-,18-,19+,20+,21-,22+,24+,25+,26-/m1/s1
IUPAC Name2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid
Traditional IUPAC Name2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid
Chemical FormulaC26H45NO7S
SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[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
Chemical Taxonomy
Description belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Trihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Cyclic alcohol
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Organosulfonic acid
  • Sulfonyl
  • Alkanesulfonic acid
  • Secondary alcohol
  • Carboximidic acid
  • Polyol
  • Carboximidic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Alcohol
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point125 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.077 g/LALOGPS
logP0.79ALOGPS
logP-0.24ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)-0.88ChemAxon
pKa (Strongest Basic)-0.053ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.16 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity132.19 m³·mol⁻¹ChemAxon
Polarizability57.36 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • vacuole
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Taurine and hypotaurine metabolismec00430 Map00430
SMPDB ReactionsNot Available
KEGG Reactions
taurocholic acid + Adenosine triphosphate + watertaurocholic acid + phosphate + hydron + ADP
taurocholic acid + Adenosine triphosphate + watertaurocholic acid + phosphate + hydron + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0000090000-911b2f8adf5d8a253a26JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0000090000-229891181661857b574bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0000090000-e3b432e2a36b91fb1106JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0000090000-afa59839c0e5c1b1f875JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0000090000-b29692cfc9f66c4205c5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0gvk-0019610000-6cd348047dc06e3abb7eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0010390000-b424218e255bf3091fdaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0191200000-4fddfc0190213d6555eeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-08i9-0590000000-c210cb519c7e4192622eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0w29-0900000000-42467048740170d1f693JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0002-0000940000-6c3a6cb6cef0d74f2139JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ea-0601910000-36005a0ab81d9a5c22c7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2901200000-0277ee57e5a77bb559edJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-8903200000-6e18275cb262330c1d11JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-3102890000-14b58b657187799f4abdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01qa-6404930000-b60c0ef5b779fc055945JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9101100000-30f5c6ad01e5a5d282daJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Rebbeor, J. F., Connolly, G. C., Ballatori, N. (2002). "Inhibition of Mrp2- and Ycf1p-mediated transport by reducing agents: evidence for GSH transport on rat Mrp2." Biochim Biophys Acta 1559:171-178.11853683
Synthesis Reference:Schersten, Tore; Bjorntorp, Per; Ekdahi, Per H.; Bjorkerud, Soren. Synthesis of taurocholic and glycocholic acids by preparations of human liver. II. An analysis of the stimulating effect of the L fraction. Biochimica et Biophysica Acta, General Sub
External Links:
ResourceLink
CHEBI ID28865
HMDB IDHMDB00036
Pubchem Compound ID440567
Kegg IDC05122
ChemSpider ID24850150
FOODB IDFDB012335
WikipediaTaurocholic_acid
BioCyc IDCPD-3743

Transporters

General function:
Involved in ATP binding
Specific function:
Exhibits ATP-dependent bile acid transport
Gene Name:
YBT1
Uniprot ID:
P32386
Molecular weight:
189160.0
Reactions