MiMeDB: Showing metabocard for Taurolithocholic acid 3-sulfate (MMDBc0000414)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:13 UTC

Update Date

2024-04-30 19:32:18 UTC

Metabolite ID

MMDBc0000414

Metabolite Identification

Common Name

Taurolithocholic acid 3-sulfate

Description

Taurolithocholic acid 3-sulfate is a sulfated bile acid. Under normal circumstances, bile acid sulfation is a minor pathway. However in the presence of cholestasis, the fraction of the bile acid pool which is sulfated increases. Sulfation of bile acids increases the aqueous solubility of the amphipathic compounds and results in more efficient renal clearance as well as in decreased reabsorption from the intestinal lumen. 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 ).

Structure

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


  Mrv1652310181922572D          

 42 45  0  0  0  0            999 V2000
 9999.649410001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5114 9999.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3695 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6549 9998.1285    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9994.2432 9998.8431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0686 9998.8431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9382 9997.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5114 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2240 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9366 9999.7851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6494 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7975 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0830 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0830 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.7975 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5097 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.5097 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2242 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9387 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.937110000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.222610000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2226 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.9371 9998.9659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.651610000.2033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6516 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.4362 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.9211 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.436210000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.436210001.2833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.149910001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.865510001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.579210001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.294910001.2833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10004.008510001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.724210001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.439910001.6958    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10005.852410002.4115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.027410002.4115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.155510001.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.579210002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.721210001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.149910000.8708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  2  0  0  0  0
  4  7  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 14  3  1  6  0  0  0
 15 17  1  0  0  0  0
 17  8  1  1  0  0  0
 12 16  1  0  0  0  0
 16  2  1  1  0  0  0
 22 16  1  0  0  0  0
 22  9  1  6  0  0  0
 19 23  1  0  0  0  0
 23 10  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 29  1  0  0  0  0
 28 42  1  6  0  0  0
 29 30  1  0  0  0  0
 29 41  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 40  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  2  0  0  0  0
 36 39  1  0  0  0  0
 28 24  1  0  0  0  0
 28 27  1  0  0  0  0
 23 25  1  0  0  0  0
 25 11  1  6  0  0  0
 20 24  1  0  0  0  0
 24  1  1  1  0  0  0
M  END

HMDB0002580
     RDKit          3D
Taurolithocholic acid 3-sulfate
 82 85  0  0  0  0  0  0  0  0999 V2000
    3.2696   -2.8216   -1.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7330   -1.5619   -1.7317 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4422   -0.3910   -1.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9533   -0.4136   -1.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5887    0.7810   -0.7186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8415    1.5821   -0.1047 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9764    1.0289   -0.7928 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6271    2.1569   -0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4714    2.2489    1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1369    0.8319    2.1160 S   0  0  0  0  0  6  0  0  0  0  0  0
    7.3275   -0.3750    1.6885 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5765    0.6323    1.8327 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9358    0.9892    3.7750 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2925   -1.3676   -1.8060 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6104   -2.4316   -2.6803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7982   -2.5781   -2.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9167   -1.3397   -1.3455 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9739   -1.1427   -0.3893 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3576   -1.5475   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1682   -1.4172    0.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2595    0.0102    0.9631 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6587    0.4418    0.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9653    1.8805    0.8252 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2487    2.1067    0.3165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3357    2.5834    1.5121 S   0  0  0  0  0  6  0  0  0  0  0  0
   -9.7147    2.5492    0.9782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9557    3.9746    1.9696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1697    1.5344    2.8390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9297    2.6958    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8378    1.8700   -0.5080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1842    0.9128    0.5054 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7761    1.8574    1.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9465    0.3501   -0.0495 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7112    0.4932    0.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5163   -0.1559    0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4213   -1.3292   -0.6236 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5098   -2.6566    0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9087   -3.7397   -1.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3727   -2.8518   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2474   -2.9509   -0.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1059   -1.5340   -2.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0618    0.5820   -1.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2577   -0.3743   -0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3995   -1.3080   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1949   -0.3854   -2.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5556    0.3316   -1.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2440    3.1328   -0.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7085    2.1588   -0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4373    2.4427    1.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0916    3.1250    1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7428    1.3342    4.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1083   -0.4033   -2.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1570   -3.3710   -2.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5449   -2.0850   -3.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707   -3.5137   -1.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5325   -2.5269   -2.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8302   -0.4827   -2.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7941   -1.6253    0.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3307   -2.6333   -1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7789   -1.0142   -1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1354   -1.8996    0.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6415   -2.0443    1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2371   -0.0202    2.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8319    0.2243   -0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3878   -0.1728    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0499    2.0996    1.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0617    1.1874    3.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4553    3.1778   -0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5518    3.5604    0.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1670    1.3501   -1.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0269    2.5723   -0.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1933    2.7180    1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6857    2.3584    2.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3124    1.3407    2.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7234    0.8685   -1.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9301    0.0456    1.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5357    1.5731    0.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1633   -0.4607    1.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0974    0.6291   -0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5075   -3.0889    0.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9485   -3.4421   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0016   -2.5659    1.0999 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
 24 25  1  0
 25 26  2  0
 25 27  2  0
 25 28  1  0
 23 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  1
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  1
 36 14  1  0
 36 17  1  0
 33 18  1  0
 31 21  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  6
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  3 43  1  0
  4 44  1  0
  4 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
  9 50  1  0
 13 51  1  0
 14 52  1  6
 15 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  6
 18 58  1  1
 19 59  1  0
 19 60  1  0
 20 61  1  0
 20 62  1  0
 21 63  1  1
 22 64  1  0
 22 65  1  0
 23 66  1  1
 28 67  1  0
 29 68  1  0
 29 69  1  0
 30 70  1  0
 30 71  1  0
 32 72  1  0
 32 73  1  0
 32 74  1  0
 33 75  1  6
 34 76  1  0
 34 77  1  0
 35 78  1  0
 35 79  1  0
 37 80  1  0
 37 81  1  0
 37 82  1  0
M  END


  Mrv1652310181922572D          

 42 45  0  0  0  0            999 V2000
 9999.649410001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5114 9999.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3695 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6549 9998.1285    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9994.2432 9998.8431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0686 9998.8431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9382 9997.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5114 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2240 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9366 9999.7851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6494 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7975 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0830 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0830 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.7975 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5097 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.5097 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2242 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9387 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.937110000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.222610000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2226 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.9371 9998.9659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.651610000.2033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6516 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.4362 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.9211 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.436210000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.436210001.2833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.149910001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.865510001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.579210001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.294910001.2833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10004.008510001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.724210001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.439910001.6958    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10005.852410002.4115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.027410002.4115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.155510001.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.579210002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.721210001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.149910000.8708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  2  0  0  0  0
  4  7  1  0  0  0  0
 12 13  1  0  0  0  0
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 14  3  1  6  0  0  0
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 17  8  1  1  0  0  0
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 16  2  1  1  0  0  0
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 28 24  1  0  0  0  0
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 25 11  1  6  0  0  0
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 24  1  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000414

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@H](C)CCC(=O)NCCS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H45NO8S2/c1-17(4-9-24(28)27-14-15-36(29,30)31)21-7-8-22-20-6-5-18-16-19(35-37(32,33)34)10-12-25(18,2)23(20)11-13-26(21,22)3/h17-23H,4-16H2,1-3H3,(H,27,28)(H,29,30,31)(H,32,33,34)/t17-,18-,19-,20+,21-,22+,23+,25+,26-/m1/s1

> <INCHI_KEY>
HSNPMXROZIQAQD-GBURMNQMSA-N

> <FORMULA>
C26H45NO8S2

> <MOLECULAR_WEIGHT>
563.767

> <EXACT_MASS>
563.258658801

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
61.46919818999537

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid

> <ALOGPS_LOGP>
-0.12

> <JCHEM_LOGP>
1.2383031872909969

> <ALOGPS_LOGS>
-5.62

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
-0.6226732220547602

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.613557186637399

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1053721686589895

> <JCHEM_POLAR_SURFACE_AREA>
147.07

> <JCHEM_REFRACTIVITY>
139.07829999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002580
     RDKit          3D
Taurolithocholic acid 3-sulfate
 82 85  0  0  0  0  0  0  0  0999 V2000
    3.2696   -2.8216   -1.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7330   -1.5619   -1.7317 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4422   -0.3910   -1.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9533   -0.4136   -1.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5887    0.7810   -0.7186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8415    1.5821   -0.1047 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9764    1.0289   -0.7928 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6271    2.1569   -0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4714    2.2489    1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1369    0.8319    2.1160 S   0  0  0  0  0  6  0  0  0  0  0  0
    7.3275   -0.3750    1.6885 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5765    0.6323    1.8327 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9358    0.9892    3.7750 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2925   -1.3676   -1.8060 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6104   -2.4316   -2.6803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7982   -2.5781   -2.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9167   -1.3397   -1.3455 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9739   -1.1427   -0.3893 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3576   -1.5475   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1682   -1.4172    0.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2595    0.0102    0.9631 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6587    0.4418    0.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9653    1.8805    0.8252 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2487    2.1067    0.3165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3357    2.5834    1.5121 S   0  0  0  0  0  6  0  0  0  0  0  0
   -9.7147    2.5492    0.9782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9557    3.9746    1.9696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1697    1.5344    2.8390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9297    2.6958    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8378    1.8700   -0.5080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1842    0.9128    0.5054 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7761    1.8574    1.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9465    0.3501   -0.0495 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7112    0.4932    0.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5163   -0.1559    0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4213   -1.3292   -0.6236 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5098   -2.6566    0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9087   -3.7397   -1.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3727   -2.8518   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2474   -2.9509   -0.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1059   -1.5340   -2.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0618    0.5820   -1.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2577   -0.3743   -0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3995   -1.3080   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1949   -0.3854   -2.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5556    0.3316   -1.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2440    3.1328   -0.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7085    2.1588   -0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4373    2.4427    1.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0916    3.1250    1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7428    1.3342    4.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1083   -0.4033   -2.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1570   -3.3710   -2.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5449   -2.0850   -3.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707   -3.5137   -1.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5325   -2.5269   -2.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8302   -0.4827   -2.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7941   -1.6253    0.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3307   -2.6333   -1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7789   -1.0142   -1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1354   -1.8996    0.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6415   -2.0443    1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2371   -0.0202    2.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8319    0.2243   -0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3878   -0.1728    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0499    2.0996    1.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0617    1.1874    3.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4553    3.1778   -0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5518    3.5604    0.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1670    1.3501   -1.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0269    2.5723   -0.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1933    2.7180    1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6857    2.3584    2.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3124    1.3407    2.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7234    0.8685   -1.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9301    0.0456    1.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5357    1.5731    0.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1633   -0.4607    1.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0974    0.6291   -0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5075   -3.0889    0.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9485   -3.4421   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0016   -2.5659    1.0999 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
 24 25  1  0
 25 26  2  0
 25 27  2  0
 25 28  1  0
 23 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  1
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  1
 36 14  1  0
 36 17  1  0
 33 18  1  0
 31 21  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  6
  3 42  1  0
  3 43  1  0
  4 44  1  0
  4 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
  9 50  1  0
 13 51  1  0
 14 52  1  6
 15 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  6
 18 58  1  1
 19 59  1  0
 19 60  1  0
 20 61  1  0
 20 62  1  0
 21 63  1  1
 22 64  1  0
 22 65  1  0
 23 66  1  1
 28 67  1  0
 29 68  1  0
 29 69  1  0
 30 70  1  0
 30 71  1  0
 32 72  1  0
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 33 75  1  6
 34 76  1  0
 34 77  1  0
 35 78  1  0
 35 79  1  0
 37 80  1  0
 37 81  1  0
 37 82  1  0
M  END

HEADER    PROTEIN                                 18-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-OCT-19         0                                  
HETATM    1  C   UNK     0    8666.0128668.598   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.0218666.266   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8658.0238662.405   0.000  0.00  0.00           O+0
HETATM    4  S   UNK     0    8656.6898663.173   0.000  0.00  0.00           S+0
HETATM    5  O   UNK     0    8655.9218664.507   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8657.4618664.507   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8655.3518662.401   0.000  0.00  0.00           O+0
HETATM    8  H   UNK     0    8662.0218661.633   0.000  0.00  0.00           H+0
HETATM    9  H   UNK     0    8663.3518663.961   0.000  0.00  0.00           H+0
HETATM   10  H   UNK     0    8664.6828666.266   0.000  0.00  0.00           H+0
HETATM   11  H   UNK     0    8666.0128663.961   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0    8660.6898665.489   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8659.3558664.719   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8659.3558663.179   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8660.6898662.409   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8662.0188664.719   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.0188663.179   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.3528662.409   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.6868663.179   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8664.6838667.816   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8663.3498667.046   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8663.3498665.506   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8664.6838664.736   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8666.0168667.046   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8666.0168665.506   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8667.4818665.030   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8668.3868666.276   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8667.4818667.522   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8667.4818669.062   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8668.8138669.832   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8670.1498669.062   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8671.4818669.832   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0    8672.8178669.062   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0    8674.1498669.832   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8675.4858669.062   0.000  0.00  0.00           C+0
HETATM   36  S   UNK     0    8676.8218669.832   0.000  0.00  0.00           S+0
HETATM   37  O   UNK     0    8677.5918671.168   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0    8676.0518671.168   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0    8678.1578669.062   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0    8671.4818671.372   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0    8666.1468669.832   0.000  0.00  0.00           C+0
HETATM   42  H   UNK     0    8668.8138668.292   0.000  0.00  0.00           H+0
CONECT    1   24                                                            
CONECT    2   16                                                            
CONECT    3    4   14                                                       
CONECT    4    3    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    4                                                            
CONECT    8   17                                                            
CONECT    9   22                                                            
CONECT   10   23                                                            
CONECT   11   25                                                            
CONECT   12   13   16                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15    3                                                  
CONECT   15   14   17                                                       
CONECT   16   17   12    2   22                                             
CONECT   17   16   18   15    8                                             
CONECT   18   17   19                                                       
CONECT   19   18   23                                                       
CONECT   20   21   24                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   16    9                                             
CONECT   23   22   19   10   25                                             
CONECT   24   25   28   20    1                                             
CONECT   25   24   26   23   11                                             
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   29   42   24   27                                             
CONECT   29   28   30   41                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   40                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36                                                            
CONECT   40   32                                                            
CONECT   41   29                                                            
CONECT   42   28                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

COMPND    HMDB0002580
HETATM    1  C1  UNL     1       3.270  -2.822  -1.180  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.733  -1.562  -1.732  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.442  -0.391  -1.099  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.953  -0.414  -1.349  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.589   0.781  -0.719  1.00  0.00           C  
HETATM    6  O1  UNL     1       4.842   1.582  -0.105  1.00  0.00           O  
HETATM    7  N1  UNL     1       6.976   1.029  -0.793  1.00  0.00           N  
HETATM    8  C6  UNL     1       7.627   2.157  -0.205  1.00  0.00           C  
HETATM    9  C7  UNL     1       7.471   2.249   1.277  1.00  0.00           C  
HETATM   10  S1  UNL     1       8.137   0.832   2.116  1.00  0.00           S  
HETATM   11  O2  UNL     1       7.328  -0.375   1.689  1.00  0.00           O  
HETATM   12  O3  UNL     1       9.577   0.632   1.833  1.00  0.00           O  
HETATM   13  O4  UNL     1       7.936   0.989   3.775  1.00  0.00           O  
HETATM   14  C8  UNL     1       1.292  -1.368  -1.806  1.00  0.00           C  
HETATM   15  C9  UNL     1       0.610  -2.432  -2.680  1.00  0.00           C  
HETATM   16  C10 UNL     1      -0.798  -2.578  -2.133  1.00  0.00           C  
HETATM   17  C11 UNL     1      -0.917  -1.340  -1.345  1.00  0.00           C  
HETATM   18  C12 UNL     1      -1.974  -1.143  -0.389  1.00  0.00           C  
HETATM   19  C13 UNL     1      -3.358  -1.548  -0.788  1.00  0.00           C  
HETATM   20  C14 UNL     1      -4.168  -1.417   0.489  1.00  0.00           C  
HETATM   21  C15 UNL     1      -4.259   0.010   0.963  1.00  0.00           C  
HETATM   22  C16 UNL     1      -5.659   0.442   0.589  1.00  0.00           C  
HETATM   23  C17 UNL     1      -5.965   1.880   0.825  1.00  0.00           C  
HETATM   24  O5  UNL     1      -7.249   2.107   0.317  1.00  0.00           O  
HETATM   25  S2  UNL     1      -8.336   2.583   1.512  1.00  0.00           S  
HETATM   26  O6  UNL     1      -9.715   2.549   0.978  1.00  0.00           O  
HETATM   27  O7  UNL     1      -7.956   3.975   1.970  1.00  0.00           O  
HETATM   28  O8  UNL     1      -8.170   1.534   2.839  1.00  0.00           O  
HETATM   29  C18 UNL     1      -4.930   2.696   0.114  1.00  0.00           C  
HETATM   30  C19 UNL     1      -3.838   1.870  -0.508  1.00  0.00           C  
HETATM   31  C20 UNL     1      -3.184   0.913   0.505  1.00  0.00           C  
HETATM   32  C21 UNL     1      -2.776   1.857   1.652  1.00  0.00           C  
HETATM   33  C22 UNL     1      -1.947   0.350  -0.049  1.00  0.00           C  
HETATM   34  C23 UNL     1      -0.711   0.493   0.791  1.00  0.00           C  
HETATM   35  C24 UNL     1       0.516  -0.156   0.270  1.00  0.00           C  
HETATM   36  C25 UNL     1       0.421  -1.329  -0.624  1.00  0.00           C  
HETATM   37  C26 UNL     1       0.510  -2.657   0.109  1.00  0.00           C  
HETATM   38  H1  UNL     1       2.909  -3.740  -1.749  1.00  0.00           H  
HETATM   39  H2  UNL     1       4.373  -2.852  -1.458  1.00  0.00           H  
HETATM   40  H3  UNL     1       3.247  -2.951  -0.101  1.00  0.00           H  
HETATM   41  H4  UNL     1       3.106  -1.534  -2.814  1.00  0.00           H  
HETATM   42  H5  UNL     1       3.062   0.582  -1.521  1.00  0.00           H  
HETATM   43  H6  UNL     1       3.258  -0.374  -0.018  1.00  0.00           H  
HETATM   44  H7  UNL     1       5.400  -1.308  -0.864  1.00  0.00           H  
HETATM   45  H8  UNL     1       5.195  -0.385  -2.426  1.00  0.00           H  
HETATM   46  H9  UNL     1       7.556   0.332  -1.316  1.00  0.00           H  
HETATM   47  H10 UNL     1       7.244   3.133  -0.621  1.00  0.00           H  
HETATM   48  H11 UNL     1       8.709   2.159  -0.439  1.00  0.00           H  
HETATM   49  H12 UNL     1       6.437   2.443   1.600  1.00  0.00           H  
HETATM   50  H13 UNL     1       8.092   3.125   1.615  1.00  0.00           H  
HETATM   51  H14 UNL     1       8.743   1.334   4.224  1.00  0.00           H  
HETATM   52  H15 UNL     1       1.108  -0.403  -2.373  1.00  0.00           H  
HETATM   53  H16 UNL     1       1.157  -3.371  -2.708  1.00  0.00           H  
HETATM   54  H17 UNL     1       0.545  -2.085  -3.752  1.00  0.00           H  
HETATM   55  H18 UNL     1      -0.971  -3.514  -1.617  1.00  0.00           H  
HETATM   56  H19 UNL     1      -1.532  -2.527  -2.987  1.00  0.00           H  
HETATM   57  H20 UNL     1      -0.830  -0.483  -2.084  1.00  0.00           H  
HETATM   58  H21 UNL     1      -1.794  -1.625   0.607  1.00  0.00           H  
HETATM   59  H22 UNL     1      -3.331  -2.633  -1.024  1.00  0.00           H  
HETATM   60  H23 UNL     1      -3.779  -1.014  -1.631  1.00  0.00           H  
HETATM   61  H24 UNL     1      -5.135  -1.900   0.302  1.00  0.00           H  
HETATM   62  H25 UNL     1      -3.641  -2.044   1.247  1.00  0.00           H  
HETATM   63  H26 UNL     1      -4.237  -0.020   2.075  1.00  0.00           H  
HETATM   64  H27 UNL     1      -5.832   0.224  -0.488  1.00  0.00           H  
HETATM   65  H28 UNL     1      -6.388  -0.173   1.157  1.00  0.00           H  
HETATM   66  H29 UNL     1      -6.050   2.100   1.913  1.00  0.00           H  
HETATM   67  H30 UNL     1      -9.062   1.187   3.090  1.00  0.00           H  
HETATM   68  H31 UNL     1      -5.455   3.178  -0.767  1.00  0.00           H  
HETATM   69  H32 UNL     1      -4.552   3.560   0.700  1.00  0.00           H  
HETATM   70  H33 UNL     1      -4.167   1.350  -1.407  1.00  0.00           H  
HETATM   71  H34 UNL     1      -3.027   2.572  -0.803  1.00  0.00           H  
HETATM   72  H35 UNL     1      -2.193   2.718   1.252  1.00  0.00           H  
HETATM   73  H36 UNL     1      -3.686   2.358   2.090  1.00  0.00           H  
HETATM   74  H37 UNL     1      -2.312   1.341   2.487  1.00  0.00           H  
HETATM   75  H38 UNL     1      -1.723   0.869  -1.016  1.00  0.00           H  
HETATM   76  H39 UNL     1      -0.930   0.046   1.782  1.00  0.00           H  
HETATM   77  H40 UNL     1      -0.536   1.573   0.963  1.00  0.00           H  
HETATM   78  H41 UNL     1       1.163  -0.461   1.124  1.00  0.00           H  
HETATM   79  H42 UNL     1       1.097   0.629  -0.264  1.00  0.00           H  
HETATM   80  H43 UNL     1      -0.507  -3.089   0.349  1.00  0.00           H  
HETATM   81  H44 UNL     1       0.949  -3.442  -0.539  1.00  0.00           H  
HETATM   82  H45 UNL     1       1.002  -2.566   1.100  1.00  0.00           H  
CONECT    1    2   38   39   40
CONECT    2    3   14   41
CONECT    3    4   42   43
CONECT    4    5   44   45
CONECT    5    6    6    7
CONECT    7    8   46
CONECT    8    9   47   48
CONECT    9   10   49   50
CONECT   10   11   11   12   12
CONECT   10   13
CONECT   13   51
CONECT   14   15   36   52
CONECT   15   16   53   54
CONECT   16   17   55   56
CONECT   17   18   36   57
CONECT   18   19   33   58
CONECT   19   20   59   60
CONECT   20   21   61   62
CONECT   21   22   31   63
CONECT   22   23   64   65
CONECT   23   24   29   66
CONECT   24   25
CONECT   25   26   26   27   27
CONECT   25   28
CONECT   28   67
CONECT   29   30   68   69
CONECT   30   31   70   71
CONECT   31   32   33
CONECT   32   72   73   74
CONECT   33   34   75
CONECT   34   35   76   77
CONECT   35   36   78   79
CONECT   36   37
CONECT   37   80   81   82
END

HMDB0002580
     RDKit          3D
Taurolithocholic acid 3-sulfate
 82 85  0  0  0  0  0  0  0  0999 V2000
    3.2696   -2.8216   -1.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7330   -1.5619   -1.7317 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4422   -0.3910   -1.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9533   -0.4136   -1.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5887    0.7810   -0.7186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8415    1.5821   -0.1047 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9764    1.0289   -0.7928 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6271    2.1569   -0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4714    2.2489    1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1369    0.8319    2.1160 S   0  0  0  0  0  6  0  0  0  0  0  0
    7.3275   -0.3750    1.6885 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5765    0.6323    1.8327 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9358    0.9892    3.7750 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2925   -1.3676   -1.8060 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6104   -2.4316   -2.6803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7982   -2.5781   -2.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9167   -1.3397   -1.3455 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9739   -1.1427   -0.3893 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3576   -1.5475   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1682   -1.4172    0.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2595    0.0102    0.9631 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6587    0.4418    0.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9653    1.8805    0.8252 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2487    2.1067    0.3165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3357    2.5834    1.5121 S   0  0  0  0  0  6  0  0  0  0  0  0
   -9.7147    2.5492    0.9782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9557    3.9746    1.9696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1697    1.5344    2.8390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9297    2.6958    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8378    1.8700   -0.5080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1842    0.9128    0.5054 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7761    1.8574    1.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9465    0.3501   -0.0495 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7112    0.4932    0.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5163   -0.1559    0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4213   -1.3292   -0.6236 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5098   -2.6566    0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9087   -3.7397   -1.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3727   -2.8518   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2474   -2.9509   -0.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1059   -1.5340   -2.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0618    0.5820   -1.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2577   -0.3743   -0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3995   -1.3080   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1949   -0.3854   -2.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5556    0.3316   -1.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2440    3.1328   -0.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7085    2.1588   -0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4373    2.4427    1.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0916    3.1250    1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7428    1.3342    4.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1083   -0.4033   -2.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1570   -3.3710   -2.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5449   -2.0850   -3.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707   -3.5137   -1.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5325   -2.5269   -2.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8302   -0.4827   -2.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7941   -1.6253    0.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3307   -2.6333   -1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7789   -1.0142   -1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1354   -1.8996    0.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6415   -2.0443    1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2371   -0.0202    2.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8319    0.2243   -0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3878   -0.1728    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0499    2.0996    1.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0617    1.1874    3.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4553    3.1778   -0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5518    3.5604    0.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1670    1.3501   -1.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0269    2.5723   -0.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1933    2.7180    1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6857    2.3584    2.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3124    1.3407    2.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7234    0.8685   -1.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9301    0.0456    1.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5357    1.5731    0.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1633   -0.4607    1.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0974    0.6291   -0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5075   -3.0889    0.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9485   -3.4421   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0016   -2.5659    1.0999 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
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 10 13  1  0
  2 14  1  0
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 15 16  1  0
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 19 20  1  0
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  1 38  1  0
  1 39  1  0
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  2 41  1  6
  3 42  1  0
  3 43  1  0
  4 44  1  0
  4 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
  9 50  1  0
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 35 78  1  0
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 37 80  1  0
 37 81  1  0
 37 82  1  0
M  END

Synonyms

Value	Source
(3alpha-Sulfato-5beta-cholan-24-oyl)-2'-aminoethanesulfonate	ChEBI
3alpha-Sulfatolithocholyltaurine	ChEBI
SLCT-3-Sulfate	ChEBI
Taurolithocholate 3-sulfate	ChEBI
Taurolithocholate sulfate	ChEBI
TLC-S	ChEBI
(3a-Sulfato-5b-cholan-24-oyl)-2'-aminoethanesulfonate	Generator
(3a-Sulfato-5b-cholan-24-oyl)-2'-aminoethanesulfonic acid	Generator
(3a-Sulphato-5b-cholan-24-oyl)-2'-aminoethanesulphonate	Generator
(3a-Sulphato-5b-cholan-24-oyl)-2'-aminoethanesulphonic acid	Generator
(3alpha-Sulfato-5beta-cholan-24-oyl)-2'-aminoethanesulfonic acid	Generator
(3alpha-Sulphato-5beta-cholan-24-oyl)-2'-aminoethanesulphonate	Generator
(3alpha-Sulphato-5beta-cholan-24-oyl)-2'-aminoethanesulphonic acid	Generator
(3Α-sulfato-5β-cholan-24-oyl)-2'-aminoethanesulfonate	Generator
(3Α-sulfato-5β-cholan-24-oyl)-2'-aminoethanesulfonic acid	Generator
(3Α-sulphato-5β-cholan-24-oyl)-2'-aminoethanesulphonate	Generator
(3Α-sulphato-5β-cholan-24-oyl)-2'-aminoethanesulphonic acid	Generator
3a-Sulfatolithocholyltaurine	Generator
3a-Sulphatolithocholyltaurine	Generator
3alpha-Sulphatolithocholyltaurine	Generator
3Α-sulfatolithocholyltaurine	Generator
3Α-sulphatolithocholyltaurine	Generator
SLCT-3-Sulfuric acid	Generator
SLCT-3-Sulphate	Generator
SLCT-3-Sulphuric acid	Generator
Taurolithocholate 3-sulphate	Generator
Taurolithocholic acid 3-sulfuric acid	Generator
Taurolithocholic acid 3-sulphuric acid	Generator
Taurolithocholate sulphate	Generator
Taurolithocholic acid sulfuric acid	Generator
Taurolithocholic acid sulphuric acid	Generator
Taurolithocholic acid 3-sulphate	HMDB
Taurolithocholic acid sulfate	HMDB
Taurolithocholic acid sulphate	HMDB
Taurolithocholic acid 3-sulfate	ChEBI

Molecular Formula

C₂₆H₄₅NO₈S₂

Average Mass

563.767

Monoisotopic Mass

563.258658801

IUPAC Name

2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[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)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@H](C)CCC(=O)NCCS(O)(=O)=O

InChI Identifier

InChI=1S/C26H45NO8S2/c1-17(4-9-24(28)27-14-15-36(29,30)31)21-7-8-22-20-6-5-18-16-19(35-37(32,33)34)10-12-25(18,2)23(20)11-13-26(21,22)3/h17-23H,4-16H2,1-3H3,(H,27,28)(H,29,30,31)(H,32,33,34)/t17-,18-,19-,20+,21-,22+,23+,25+,26-/m1/s1

InChI Key

HSNPMXROZIQAQD-GBURMNQMSA-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.

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
Sulfated steroid skeleton
Fatty amide
N-acyl-amine
Sulfuric acid monoester
Sulfate-ester
Fatty acyl
Sulfuric acid ester
Alkyl sulfate
Organic sulfuric acid or derivatives
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Alkanesulfonic acid
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Carbonyl group
Organopnictogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

steroid sulfate (CHEBI:17864 )
sulfates (C03642 )
C26 bile acids, alcohols, and derivatives (C03642 )
Taurine conjugates (C03642 )
Sulfates (LMST05020003 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0014 g/L	ALOGPS
logP	-0.12	ALOGPS
logP	1.24	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	-1.6	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	147.07 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	139.08 m³·mol⁻¹	ChemAxon
Polarizability	61.47 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192015	Bile salt sulfotransferase	Enzyme	Q06520	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Firmicutes	2	Human ; Human feces; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Feces	Detected and Quantified	0.77	0.63	nmol/g dry feces	Not Specified	Not Specified	Normal	HMDB	22664055
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0002580

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023028

KNApSAcK ID

Not Available

Chemspider ID

389078

KEGG Compound ID

C03642

BioCyc ID

TAUROLITHOCHOLATE-SULFATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6716

PubChem Compound

440071

PDB ID

Not Available

ChEBI ID

17864

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Herold BC, Kirkpatrick R, Marcellino D, Travelstead A, Pilipenko V, Krasa H, Bremer J, Dong LJ, Cooper MD: Bile salts: natural detergents for the prevention of sexually transmitted diseases. Antimicrob Agents Chemother. 1999 Apr;43(4):745-51. doi: 10.1128/AAC.43.4.745. [PubMed:10103175 ]
St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. doi: 10.1242/jeb.204.10.1673. [PubMed:11316487 ]
Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]
Zelcer N, Reid G, Wielinga P, Kuil A, van der Heijden I, Schuetz JD, Borst P: Steroid and bile acid conjugates are substrates of human multidrug-resistance protein (MRP) 4 (ATP-binding cassette C4). Biochem J. 2003 Apr 15;371(Pt 2):361-7. doi: 10.1042/BJ20021886. [PubMed:12523936 ]
Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. doi: 10.1152/ajpgi.00417.2002. [PubMed:12576301 ]
Boucherie S, Koukoui O, Nicolas V, Combettes L: Cholestatic bile acids inhibit gap junction permeability in rat hepatocyte couplets and normal rat cholangiocytes. J Hepatol. 2005 Feb;42(2):244-51. doi: 10.1016/j.jhep.2004.10.013. [PubMed:15664251 ]
Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. doi: 10.1161/01.ATV.0000178994.21828.a7. Epub 2005 Jul 21. [PubMed:16037564 ]
Hayashi H, Takada T, Suzuki H, Onuki R, Hofmann AF, Sugiyama Y: Transport by vesicles of glycine- and taurine-conjugated bile salts and taurolithocholate 3-sulfate: a comparison of human BSEP with rat Bsep. Biochim Biophys Acta. 2005 Dec 30;1738(1-3):54-62. doi: 10.1016/j.bbalip.2005.10.006. Epub 2005 Nov 15. [PubMed:16332456 ]

Showing metabocard for Taurolithocholic acid 3-sulfate (MMDBc0000414)

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