NP-MRD: Showing NP-Card for Taurodeoxycholic acid (NP0001203)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-06-29 00:46:36 UTC

NP-MRD ID

NP0001203

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Taurodeoxycholic acid

Description

Taurodeoxycholic acid is a bile salt formed in the liver by conjugation of deoxycholate with taurine, usually as the sodium salt. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the 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 ). Taurodeoxycholic acid can be found in Escherichia (PMID: 30736766 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652305271900302D          

 39 42  0  0  1  0            999 V2000
   19.3690  -10.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3690  -11.0356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.0835  -11.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7979  -11.0356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.7979  -10.2106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.0835   -9.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5124  -11.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2269  -11.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2269  -10.2106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.5124   -9.7981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.9414   -9.7981    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.9414   -8.9731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.2269   -8.5606    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.5124   -8.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7261  -10.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2110   -9.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7261   -8.7181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.6545  -11.4481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0277   -8.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9810   -7.9335    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.4290   -7.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7880   -7.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0429   -6.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8499   -6.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5124  -10.6231    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.7979   -9.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2269   -9.3856    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.0277  -10.6186    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.4478   -8.5664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.8038  -11.7288    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.1049   -6.0212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9118   -5.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2269   -7.7356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4020   -7.4189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1667   -5.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9737   -4.8934    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.2286   -4.1088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5257   -5.5065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4216   -4.2804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  1  6  0  0  0
 12 19  1  1  0  0  0
 17 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 10 25  1  6  0  0  0
  5 26  1  1  0  0  0
  9 27  1  1  0  0  0
 11 28  1  6  0  0  0
 17 29  1  6  0  0  0
  4 30  1  1  0  0  0
 31 24  1  0  0  0  0
 32 31  1  0  0  0  0
 13 33  1  6  0  0  0
 34 24  2  0  0  0  0
 35 32  1  0  0  0  0
 36 35  1  0  0  0  0
 37 36  1  0  0  0  0
 38 36  2  0  0  0  0
 39 36  2  0  0  0  0
M  END

HMDB0000896
     RDKit          3D
Taurodeoxycholic acid
 79 82  0  0  0  0  0  0  0  0999 V2000
    1.8473    2.6534    1.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0358    1.1869    1.3262 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4832    0.8394    1.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1144    1.1740   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5445    0.7783   -0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0327    0.2481    0.9695 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4102    0.9772   -1.1719 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7910    0.6102   -1.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0270   -0.8688   -0.9640 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7620   -1.2510   -0.9928 S   0  0  0  0  0  6  0  0  0  0  0  0
    9.9534   -2.7057   -0.6805 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3276   -0.9649   -2.3350 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5400   -0.3830    0.2365 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1584    0.3498    0.4277 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4296   -1.1376    0.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1432   -1.8636    0.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8057   -0.7968    0.0322 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2466   -1.0713    0.2767 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5979   -2.3696   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7395   -2.1123   -1.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8793   -1.3937   -0.6961 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0256   -1.3247   -1.6857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1849   -0.5550   -1.0897 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.2497   -0.6167   -1.9736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7185    0.8399   -0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2000    0.9931   -0.9725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4813   -0.0429   -0.1724 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9198    0.0942    1.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9969    0.1108   -0.3086 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5100    1.3769    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0369    1.5919    0.1800 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6866    1.8618   -1.1401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902    0.4358    0.7579 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5006    0.3596    2.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2138    3.1132    1.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8436    3.1680    1.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4859    2.9540    0.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7325    0.9617    2.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7037   -0.2252    1.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0218    1.4226    2.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0151    2.2426   -0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321    0.6029   -0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9875    1.4217   -2.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3496    1.1890   -0.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2584    0.8843   -2.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5475   -1.4067   -1.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6469   -1.1315    0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4988   -0.8526    1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3545    0.5146   -0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6654   -1.3303    1.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2873   -1.4717    0.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1610   -2.5690    1.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3715   -2.4703   -0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6993   -0.5542   -1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5143   -1.1890    1.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9502   -3.1500    0.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7646   -2.7662   -0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1180   -3.1026   -1.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4357   -1.5576   -2.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2524   -2.0333    0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7155   -0.9319   -2.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3567   -2.3793   -1.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4554   -1.1032   -0.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7991   -1.4173   -1.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0336    1.0981    0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2025    1.5163   -1.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9768    2.0103   -0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0051    0.9070   -2.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3343    1.1076    1.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7588   -0.6201    1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1004   -0.0756    1.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    0.1563   -1.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7070    1.3119    1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0550    2.2586   -0.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7803    2.5009    0.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6430    2.8369   -1.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2847    1.3710    2.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003   -0.3299    2.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5063    0.0943    2.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  2  0
 10 13  1  0
  2 14  1  0
 14 15  1  0
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 17 18  1  0
 18 19  1  0
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 20 21  1  0
 21 22  1  0
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 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  1
 33 14  1  0
 33 17  1  0
 29 18  1  0
 27 21  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  1
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 13 48  1  0
 14 49  1  6
 15 50  1  0
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 17 54  1  6
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 26 68  1  0
 28 69  1  0
 28 70  1  0
 28 71  1  0
 29 72  1  6
 30 73  1  0
 30 74  1  0
 31 75  1  1
 32 76  1  0
 34 77  1  0
 34 78  1  0
 34 79  1  0
M  END


  Mrv1652305271900302D          

 39 42  0  0  1  0            999 V2000
   19.3690  -10.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3690  -11.0356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.0835  -11.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7979  -11.0356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.7979  -10.2106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.0835   -9.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5124  -11.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2269  -11.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2269  -10.2106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.5124   -9.7981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.9414   -9.7981    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.9414   -8.9731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.2269   -8.5606    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.5124   -8.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7261  -10.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2110   -9.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7261   -8.7181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.6545  -11.4481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0277   -8.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9810   -7.9335    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.4290   -7.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7880   -7.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0429   -6.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8499   -6.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5124  -10.6231    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.7979   -9.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2269   -9.3856    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.0277  -10.6186    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.4478   -8.5664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.8038  -11.7288    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.1049   -6.0212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9118   -5.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2269   -7.7356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4020   -7.4189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1667   -5.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9737   -4.8934    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.2286   -4.1088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5257   -5.5065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4216   -4.2804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  1  6  0  0  0
 12 19  1  1  0  0  0
 17 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 10 25  1  6  0  0  0
  5 26  1  1  0  0  0
  9 27  1  1  0  0  0
 11 28  1  6  0  0  0
 17 29  1  6  0  0  0
  4 30  1  1  0  0  0
 31 24  1  0  0  0  0
 32 31  1  0  0  0  0
 13 33  1  6  0  0  0
 34 24  2  0  0  0  0
 35 32  1  0  0  0  0
 36 35  1  0  0  0  0
 37 36  1  0  0  0  0
 38 36  2  0  0  0  0
 39 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001203

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
AWDRATDZQPNJFN-VAYUFCLWSA-N

> <FORMULA>
C26H45NO6S

> <MOLECULAR_WEIGHT>
499.704

> <EXACT_MASS>
499.296758867

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
56.552705508993

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(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

> <ALOGPS_LOGP>
1.19

> <JCHEM_LOGP>
1.1358244460516165

> <ALOGPS_LOGS>
-4.81

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.518493370934234

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.7519355598435356

> <JCHEM_PKA_STRONGEST_BASIC>
-0.19573728975273197

> <JCHEM_POLAR_SURFACE_AREA>
123.93

> <JCHEM_REFRACTIVITY>
130.60199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.76e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000896
     RDKit          3D
Taurodeoxycholic acid
 79 82  0  0  0  0  0  0  0  0999 V2000
    1.8473    2.6534    1.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0358    1.1869    1.3262 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4832    0.8394    1.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1144    1.1740   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5445    0.7783   -0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0327    0.2481    0.9695 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4102    0.9772   -1.1719 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7910    0.6102   -1.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0270   -0.8688   -0.9640 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7620   -1.2510   -0.9928 S   0  0  0  0  0  6  0  0  0  0  0  0
    9.9534   -2.7057   -0.6805 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3276   -0.9649   -2.3350 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5400   -0.3830    0.2365 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1584    0.3498    0.4277 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4296   -1.1376    0.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1432   -1.8636    0.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8057   -0.7968    0.0322 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2466   -1.0713    0.2767 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5979   -2.3696   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7395   -2.1123   -1.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8793   -1.3937   -0.6961 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0256   -1.3247   -1.6857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1849   -0.5550   -1.0897 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.2497   -0.6167   -1.9736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7185    0.8399   -0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2000    0.9931   -0.9725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4813   -0.0429   -0.1724 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9198    0.0942    1.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9969    0.1108   -0.3086 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5100    1.3769    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0369    1.5919    0.1800 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6866    1.8618   -1.1401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902    0.4358    0.7579 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5006    0.3596    2.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2138    3.1132    1.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8436    3.1680    1.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4859    2.9540    0.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7325    0.9617    2.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7037   -0.2252    1.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0218    1.4226    2.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0151    2.2426   -0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321    0.6029   -0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9875    1.4217   -2.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3496    1.1890   -0.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2584    0.8843   -2.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5475   -1.4067   -1.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6469   -1.1315    0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4988   -0.8526    1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3545    0.5146   -0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6654   -1.3303    1.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2873   -1.4717    0.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1610   -2.5690    1.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3715   -2.4703   -0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6993   -0.5542   -1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5143   -1.1890    1.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9502   -3.1500    0.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7646   -2.7662   -0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1180   -3.1026   -1.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4357   -1.5576   -2.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2524   -2.0333    0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7155   -0.9319   -2.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3567   -2.3793   -1.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4554   -1.1032   -0.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7991   -1.4173   -1.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0336    1.0981    0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2025    1.5163   -1.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9768    2.0103   -0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0051    0.9070   -2.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3343    1.1076    1.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7588   -0.6201    1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1004   -0.0756    1.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    0.1563   -1.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7070    1.3119    1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0550    2.2586   -0.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7803    2.5009    0.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6430    2.8369   -1.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2847    1.3710    2.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003   -0.3299    2.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5063    0.0943    2.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  2  0
 10 13  1  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  1
 33 14  1  0
 33 17  1  0
 29 18  1  0
 27 21  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  1
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 13 48  1  0
 14 49  1  6
 15 50  1  0
 15 51  1  0
 16 52  1  0
 16 53  1  0
 17 54  1  6
 18 55  1  1
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  1
 22 61  1  0
 22 62  1  0
 23 63  1  1
 24 64  1  0
 25 65  1  0
 25 66  1  0
 26 67  1  0
 26 68  1  0
 28 69  1  0
 28 70  1  0
 28 71  1  0
 29 72  1  6
 30 73  1  0
 30 74  1  0
 31 75  1  1
 32 76  1  0
 34 77  1  0
 34 78  1  0
 34 79  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      36.155 -19.060   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      36.155 -20.600   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      37.489 -21.370   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      38.823 -20.600   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      38.823 -19.060   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      37.489 -18.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      40.156 -21.370   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      41.490 -20.600   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      41.490 -19.060   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      40.156 -18.290   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      42.824 -18.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      42.824 -16.750   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      41.490 -15.980   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      40.156 -16.750   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      44.289 -18.766   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      45.194 -17.520   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      44.289 -16.274   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      34.822 -21.370   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      42.985 -15.218   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      44.765 -14.809   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      43.734 -13.665   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      46.271 -14.489   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      46.747 -13.024   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      48.253 -12.704   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0      40.156 -19.830   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0      38.823 -17.520   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0      41.490 -17.520   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      42.985 -19.821   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      45.636 -15.991   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      38.834 -21.894   0.000  0.00  0.00           H+0
HETATM   31  N   UNK     0      48.729 -11.240   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0      50.235 -10.919   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      41.490 -14.440   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      49.284 -13.849   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      50.711  -9.455   0.000  0.00  0.00           C+0
HETATM   36  S   UNK     0      52.218  -9.134   0.000  0.00  0.00           S+0
HETATM   37  O   UNK     0      52.693  -7.670   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      53.248 -10.279   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      51.187  -7.990   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   30                                             
CONECT    5    4    6   10   26                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   27                                             
CONECT   10    9    5   14   25                                             
CONECT   11    9   12   15   28                                             
CONECT   12   11   13   17   19                                             
CONECT   13   12   14   33                                                  
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   20   29                                             
CONECT   18    2                                                            
CONECT   19   12                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   31   34                                                  
CONECT   25   10                                                            
CONECT   26    5                                                            
CONECT   27    9                                                            
CONECT   28   11                                                            
CONECT   29   17                                                            
CONECT   30    4                                                            
CONECT   31   24   32                                                       
CONECT   32   31   35                                                       
CONECT   33   13                                                            
CONECT   34   24                                                            
CONECT   35   32   36                                                       
CONECT   36   35   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

COMPND    HMDB0000896
HETATM    1  C1  UNL     1       1.847   2.653   1.132  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.036   1.187   1.326  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.483   0.839   1.216  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.114   1.174  -0.092  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.544   0.778  -0.060  1.00  0.00           C  
HETATM    6  O1  UNL     1       6.033   0.248   0.970  1.00  0.00           O  
HETATM    7  N1  UNL     1       6.410   0.977  -1.172  1.00  0.00           N  
HETATM    8  C6  UNL     1       7.791   0.610  -1.183  1.00  0.00           C  
HETATM    9  C7  UNL     1       8.027  -0.869  -0.964  1.00  0.00           C  
HETATM   10  S1  UNL     1       9.762  -1.251  -0.993  1.00  0.00           S  
HETATM   11  O2  UNL     1       9.953  -2.706  -0.680  1.00  0.00           O  
HETATM   12  O3  UNL     1      10.328  -0.965  -2.335  1.00  0.00           O  
HETATM   13  O4  UNL     1      10.540  -0.383   0.236  1.00  0.00           O  
HETATM   14  C8  UNL     1       1.158   0.350   0.428  1.00  0.00           C  
HETATM   15  C9  UNL     1       1.430  -1.138   0.700  1.00  0.00           C  
HETATM   16  C10 UNL     1       0.143  -1.864   0.370  1.00  0.00           C  
HETATM   17  C11 UNL     1      -0.806  -0.797   0.032  1.00  0.00           C  
HETATM   18  C12 UNL     1      -2.247  -1.071   0.277  1.00  0.00           C  
HETATM   19  C13 UNL     1      -2.598  -2.370  -0.411  1.00  0.00           C  
HETATM   20  C14 UNL     1      -3.740  -2.112  -1.371  1.00  0.00           C  
HETATM   21  C15 UNL     1      -4.879  -1.394  -0.696  1.00  0.00           C  
HETATM   22  C16 UNL     1      -6.026  -1.325  -1.686  1.00  0.00           C  
HETATM   23  C17 UNL     1      -7.185  -0.555  -1.090  1.00  0.00           C  
HETATM   24  O5  UNL     1      -8.250  -0.617  -1.974  1.00  0.00           O  
HETATM   25  C18 UNL     1      -6.718   0.840  -0.818  1.00  0.00           C  
HETATM   26  C19 UNL     1      -5.200   0.993  -0.972  1.00  0.00           C  
HETATM   27  C20 UNL     1      -4.481  -0.043  -0.172  1.00  0.00           C  
HETATM   28  C21 UNL     1      -4.920   0.094   1.271  1.00  0.00           C  
HETATM   29  C22 UNL     1      -2.997   0.111  -0.309  1.00  0.00           C  
HETATM   30  C23 UNL     1      -2.510   1.377   0.355  1.00  0.00           C  
HETATM   31  C24 UNL     1      -1.037   1.592   0.180  1.00  0.00           C  
HETATM   32  O6  UNL     1      -0.687   1.862  -1.140  1.00  0.00           O  
HETATM   33  C25 UNL     1      -0.290   0.436   0.758  1.00  0.00           C  
HETATM   34  C26 UNL     1      -0.501   0.360   2.238  1.00  0.00           C  
HETATM   35  H1  UNL     1       1.214   3.113   1.946  1.00  0.00           H  
HETATM   36  H2  UNL     1       2.844   3.168   1.279  1.00  0.00           H  
HETATM   37  H3  UNL     1       1.486   2.954   0.143  1.00  0.00           H  
HETATM   38  H4  UNL     1       1.733   0.962   2.382  1.00  0.00           H  
HETATM   39  H5  UNL     1       3.704  -0.225   1.439  1.00  0.00           H  
HETATM   40  H6  UNL     1       4.022   1.423   2.009  1.00  0.00           H  
HETATM   41  H7  UNL     1       4.015   2.243  -0.374  1.00  0.00           H  
HETATM   42  H8  UNL     1       3.632   0.603  -0.925  1.00  0.00           H  
HETATM   43  H9  UNL     1       5.987   1.422  -2.023  1.00  0.00           H  
HETATM   44  H10 UNL     1       8.350   1.189  -0.398  1.00  0.00           H  
HETATM   45  H11 UNL     1       8.258   0.884  -2.138  1.00  0.00           H  
HETATM   46  H12 UNL     1       7.547  -1.407  -1.795  1.00  0.00           H  
HETATM   47  H13 UNL     1       7.647  -1.131   0.027  1.00  0.00           H  
HETATM   48  H14 UNL     1      10.499  -0.853   1.099  1.00  0.00           H  
HETATM   49  H15 UNL     1       1.355   0.515  -0.646  1.00  0.00           H  
HETATM   50  H16 UNL     1       1.665  -1.330   1.747  1.00  0.00           H  
HETATM   51  H17 UNL     1       2.287  -1.472   0.086  1.00  0.00           H  
HETATM   52  H18 UNL     1      -0.161  -2.569   1.158  1.00  0.00           H  
HETATM   53  H19 UNL     1       0.372  -2.470  -0.554  1.00  0.00           H  
HETATM   54  H20 UNL     1      -0.699  -0.554  -1.066  1.00  0.00           H  
HETATM   55  H21 UNL     1      -2.514  -1.189   1.338  1.00  0.00           H  
HETATM   56  H22 UNL     1      -2.950  -3.150   0.292  1.00  0.00           H  
HETATM   57  H23 UNL     1      -1.765  -2.766  -0.989  1.00  0.00           H  
HETATM   58  H24 UNL     1      -4.118  -3.103  -1.701  1.00  0.00           H  
HETATM   59  H25 UNL     1      -3.436  -1.558  -2.271  1.00  0.00           H  
HETATM   60  H26 UNL     1      -5.252  -2.033   0.152  1.00  0.00           H  
HETATM   61  H27 UNL     1      -5.715  -0.932  -2.670  1.00  0.00           H  
HETATM   62  H28 UNL     1      -6.357  -2.379  -1.852  1.00  0.00           H  
HETATM   63  H29 UNL     1      -7.455  -1.103  -0.143  1.00  0.00           H  
HETATM   64  H30 UNL     1      -8.799  -1.417  -1.721  1.00  0.00           H  
HETATM   65  H31 UNL     1      -7.034   1.098   0.219  1.00  0.00           H  
HETATM   66  H32 UNL     1      -7.202   1.516  -1.539  1.00  0.00           H  
HETATM   67  H33 UNL     1      -4.977   2.010  -0.640  1.00  0.00           H  
HETATM   68  H34 UNL     1      -5.005   0.907  -2.070  1.00  0.00           H  
HETATM   69  H35 UNL     1      -5.334   1.108   1.488  1.00  0.00           H  
HETATM   70  H36 UNL     1      -5.759  -0.620   1.484  1.00  0.00           H  
HETATM   71  H37 UNL     1      -4.100  -0.076   1.988  1.00  0.00           H  
HETATM   72  H38 UNL     1      -2.736   0.156  -1.376  1.00  0.00           H  
HETATM   73  H39 UNL     1      -2.707   1.312   1.449  1.00  0.00           H  
HETATM   74  H40 UNL     1      -3.055   2.259  -0.043  1.00  0.00           H  
HETATM   75  H41 UNL     1      -0.780   2.501   0.774  1.00  0.00           H  
HETATM   76  H42 UNL     1      -0.643   2.837  -1.303  1.00  0.00           H  
HETATM   77  H43 UNL     1      -0.285   1.371   2.653  1.00  0.00           H  
HETATM   78  H44 UNL     1       0.200  -0.330   2.752  1.00  0.00           H  
HETATM   79  H45 UNL     1      -1.506   0.094   2.557  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3   14   38
CONECT    3    4   39   40
CONECT    4    5   41   42
CONECT    5    6    6    7
CONECT    7    8   43
CONECT    8    9   44   45
CONECT    9   10   46   47
CONECT   10   11   11   12   12
CONECT   10   13
CONECT   13   48
CONECT   14   15   33   49
CONECT   15   16   50   51
CONECT   16   17   52   53
CONECT   17   18   33   54
CONECT   18   19   29   55
CONECT   19   20   56   57
CONECT   20   21   58   59
CONECT   21   22   27   60
CONECT   22   23   61   62
CONECT   23   24   25   63
CONECT   24   64
CONECT   25   26   65   66
CONECT   26   27   67   68
CONECT   27   28   29
CONECT   28   69   70   71
CONECT   29   30   72
CONECT   30   31   73   74
CONECT   31   32   33   75
CONECT   32   76
CONECT   33   34
CONECT   34   77   78   79
END

HMDB0000896
     RDKit          3D
Taurodeoxycholic acid
 79 82  0  0  0  0  0  0  0  0999 V2000
    1.8473    2.6534    1.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0358    1.1869    1.3262 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4832    0.8394    1.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1144    1.1740   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5445    0.7783   -0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0327    0.2481    0.9695 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4102    0.9772   -1.1719 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7910    0.6102   -1.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0270   -0.8688   -0.9640 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7620   -1.2510   -0.9928 S   0  0  0  0  0  6  0  0  0  0  0  0
    9.9534   -2.7057   -0.6805 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3276   -0.9649   -2.3350 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5400   -0.3830    0.2365 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1584    0.3498    0.4277 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4296   -1.1376    0.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1432   -1.8636    0.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8057   -0.7968    0.0322 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2466   -1.0713    0.2767 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5979   -2.3696   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7395   -2.1123   -1.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8793   -1.3937   -0.6961 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0256   -1.3247   -1.6857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1849   -0.5550   -1.0897 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.2497   -0.6167   -1.9736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7185    0.8399   -0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2000    0.9931   -0.9725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4813   -0.0429   -0.1724 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9198    0.0942    1.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9969    0.1108   -0.3086 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5100    1.3769    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0369    1.5919    0.1800 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6866    1.8618   -1.1401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902    0.4358    0.7579 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5006    0.3596    2.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2138    3.1132    1.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8436    3.1680    1.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4859    2.9540    0.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7325    0.9617    2.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7037   -0.2252    1.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0218    1.4226    2.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0151    2.2426   -0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321    0.6029   -0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9875    1.4217   -2.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3496    1.1890   -0.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2584    0.8843   -2.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5475   -1.4067   -1.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6469   -1.1315    0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4988   -0.8526    1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3545    0.5146   -0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6654   -1.3303    1.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2873   -1.4717    0.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1610   -2.5690    1.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3715   -2.4703   -0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6993   -0.5542   -1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5143   -1.1890    1.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9502   -3.1500    0.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7646   -2.7662   -0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1180   -3.1026   -1.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4357   -1.5576   -2.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2524   -2.0333    0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7155   -0.9319   -2.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3567   -2.3793   -1.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4554   -1.1032   -0.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7991   -1.4173   -1.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0336    1.0981    0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2025    1.5163   -1.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9768    2.0103   -0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0051    0.9070   -2.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3343    1.1076    1.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7588   -0.6201    1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1004   -0.0756    1.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    0.1563   -1.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7070    1.3119    1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0550    2.2586   -0.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7803    2.5009    0.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6430    2.8369   -1.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2847    1.3710    2.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003   -0.3299    2.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5063    0.0943    2.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  2  0
 10 13  1  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  1
 33 14  1  0
 33 17  1  0
 29 18  1  0
 27 21  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  1
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 13 48  1  0
 14 49  1  6
 15 50  1  0
 15 51  1  0
 16 52  1  0
 16 53  1  0
 17 54  1  6
 18 55  1  1
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  1
 22 61  1  0
 22 62  1  0
 23 63  1  1
 24 64  1  0
 25 65  1  0
 25 66  1  0
 26 67  1  0
 26 68  1  0
 28 69  1  0
 28 70  1  0
 28 71  1  0
 29 72  1  6
 30 73  1  0
 30 74  1  0
 31 75  1  1
 32 76  1  0
 34 77  1  0
 34 78  1  0
 34 79  1  0
M  END

View in JSmol

Synonyms

Value	Source
Taurodeoxycholate	ChEBI
Acid, taurodeoxycholic	HMDB
Deoxycholate, taurine	HMDB
Sodium taurodeoxycholate	HMDB
Taurine deoxycholate	HMDB
Deoxycholyltaurine	HMDB
Taurodeoxycholate, sodium	HMDB
Deoxytaurocholate	HMDB
Deoxytaurocholic acid	HMDB
N-(3a,12a-Dihydroxy-5b-cholan-24-oyl)-taurine	HMDB
Sodium taurodeoxylate	HMDB
Taurodeoxycholic acid sodium salt	HMDB
Taurodeoxycholic acid sodium salt hydrate	HMDB
Taurodesoxycholate	HMDB
Taurodesoxycholic acid	HMDB
Tudcabil	HMDB

Chemical Formula

C₂₆H₄₅NO₆S

Average Mass

499.7040 Da

Monoisotopic Mass

499.29676 Da

IUPAC Name

2-[(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 Name

2-[(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 Number

516-50-7

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 Key

AWDRATDZQPNJFN-VAYUFCLWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Streptomyces nigra	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Taurinated 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 Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid taurine conjugate (CHEBI:9410 )
Taurine conjugates (LMST05040013 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	204 - 208 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	41 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0078 g/L	ALOGPS
logP	1.19	ALOGPS
logP	1.14	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	-0.75	ChemAxon
pKa (Strongest Basic)	-0.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	123.93 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	130.6 m³·mol⁻¹	ChemAxon
Polarizability	56.55 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0000896

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022304

KNApSAcK ID

Not Available

Chemspider ID

2015539

KEGG Compound ID

C05463

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Taurodeoxycholic_acid

METLIN ID

5853

PubChem Compound

2733768

PDB ID

Not Available

ChEBI ID

9410

Good Scents ID

Not Available

References

General References

Foley DP, Collins BR, Magee JC, Platt JL, Katz E, Harland RC, Meyers WC, Chari RS: Bile acids in xenogeneic ex-vivo liver perfusion: function of xenoperfused livers and compatibility with human bile salts and porcine livers. Transplantation. 2000 Jan 27;69(2):242-8. [PubMed:10670634 ]
Bretagne JF, Vidon N, L'Hirondel C, Bernier JJ: Increased cell loss in the human jejunum induced by laxatives (ricinoleic acid, dioctyl sodium sulphosuccinate, magnesium sulphate, bile salts). Gut. 1981 Apr;22(4):264-9. [PubMed:6165655 ]
Leveau P, Wang X, Sun Z, Borjesson A, Andersson E, Andersson R: Severity of pancreatitis-associated gut barrier dysfunction is reduced following treatment with the PAF inhibitor lexipafant. Biochem Pharmacol. 2005 May 1;69(9):1325-31. [PubMed:15826603 ]
Lim HJ, Kim SY, Lee WK: Isolation of cholesterol-lowering lactic acid bacteria from human intestine for probiotic use. J Vet Sci. 2004 Dec;5(4):391-5. [PubMed:15613825 ]
Muhlbauer M, Allard B, Bosserhoff AK, Kiessling S, Herfarth H, Rogler G, Scholmerich J, Jobin C, Hellerbrand C: Differential effects of deoxycholic acid and taurodeoxycholic acid on NF-kappa B signal transduction and IL-8 gene expression in colonic epithelial cells. Am J Physiol Gastrointest Liver Physiol. 2004 Jun;286(6):G1000-8. Epub 2004 Jan 15. [PubMed:14726307 ]
Elkins CA, Mullis LB: Bile-mediated aminoglycoside sensitivity in Lactobacillus species likely results from increased membrane permeability attributable to cholic acid. Appl Environ Microbiol. 2004 Dec;70(12):7200-9. [PubMed:15574918 ]
Aubert E, Sbarra V, Le Petit-Thevenin J, Valette A, Lombardo D: Site-directed mutagenesis of the basic N-terminal cluster of pancreatic bile salt-dependent lipase. Functional significance. J Biol Chem. 2002 Sep 20;277(38):34987-96. Epub 2002 Jul 10. [PubMed:12110666 ]
Xie Q, Li GM, Zhou XQ, Liao D, Yu H, Guo Q: [Effect of Tauroursodeoxycholic acid on cytochrome C-mediated apoptosis in HepG2 cells]. Zhonghua Gan Zang Bing Za Zhi. 2003 May;11(5):298-301. [PubMed:12773247 ]

Showing NP-Card for Taurodeoxycholic acid (NP0001203)

MOL for NP0001203 (Taurodeoxycholic acid)

3D MOL for NP0001203 (Taurodeoxycholic acid)

3D SDF for NP0001203 (Taurodeoxycholic acid)

3D-SDF for NP0001203 (Taurodeoxycholic acid)

PDB for NP0001203 (Taurodeoxycholic acid)

3D PDB for NP0001203 (Taurodeoxycholic acid)

SMILES for NP0001203 (Taurodeoxycholic acid)

INCHI for NP0001203 (Taurodeoxycholic acid)

Structure for NP0001203 (Taurodeoxycholic acid)

3D Structure for NP0001203 (Taurodeoxycholic acid)