MiMeDB: Showing metabocard for Lithocholyltaurine (MMDBc0000146)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:37:33 UTC

Update Date

2024-04-30 19:31:13 UTC

Metabolite ID

MMDBc0000146

Metabolite Identification

Common Name

Lithocholyltaurine

Description

Lithocholyltaurine is a bile salt formed in the liver from lithocholic acid conjugation with taurine, usually as the sodium salt. It solubilizes fats for absorption and is itself absorbed. Lithocholic acid, a hydrophobic secondary bile acid, is well known to cause intrahepatic cholestasis. There have been extensive studies on the mechanisms of lithocholate-induced cholestasis in animals. Lithocholate diminishes both the bile acid-dependent and independent bile flow. In humans, elevated levels of lithocholic acid are found in patients with chronic cholestatic liver disease. Lithocholyltaurine impairs both the bile canalicular contractions and the canalicular bile secretion, possibly by acting directly on the canalicular membranes in lithocholyltaurine-induced cholestasis. Lithocholyltaurine induce acute cholestasis-associated with retrieval of the bile salt export pump. The bile salt export pump (BSEP) of hepatocyte secretes conjugated bile salts across the canalicular membrane in an ATP-dependent manner. Hepatic retention of bile acids may lead to liver injury by hepatocyte apoptosis and eventually deterioration of cholestatic liver diseases. One mechanism of induced apoptosis by lithocholyltaurine is the induction of transcriptional activity of AP-1 (activation protein-1). (PMID: 16981261 , 15763547 , 16332456 , 18164257 ).

Structure

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


  Mrv1652309152018592D          

 38 41  0  0  0  0            999 V2000
 9998.933710001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7957 9999.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6538 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2209 9999.7851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5083 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9337 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7957 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7940 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.7940 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.5085 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2230 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.221410000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.506910000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5069 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.2214 9998.9659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.0818 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3673 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3673 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.0818 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.935910000.2033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9359 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.7205 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.2054 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.720510000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.720510001.2833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.434510001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.005910001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.150210001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.863910001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.579510001.2833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.863910002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.293210001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.008910001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.724510001.6958    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10005.137010002.4115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.312010002.4115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.440210001.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.434510000.8708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  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
 18  3  1  6  0  0  0
 19  9  1  0  0  0  0
  9  7  1  1  0  0  0
 16  8  1  0  0  0  0
  8  2  1  1  0  0  0
 14  8  1  0  0  0  0
 14  5  1  6  0  0  0
 11 15  1  0  0  0  0
 15  4  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 24 38  1  6  0  0  0
 25 26  1  0  0  0  0
 25 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  2  0  0  0  0
 34 37  1  0  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
 15 21  1  0  0  0  0
 21  6  1  6  0  0  0
 12 20  1  0  0  0  0
 20  1  1  1  0  0  0
M  END

HMDB0000722
     RDKit          3D
Lithocholyltaurine
 78 81  0  0  0  0  0  0  0  0999 V2000
    2.8472   -0.1611   -3.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538    0.0022   -1.7833 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0557   -0.4907   -0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3676    0.2627   -0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2014   -0.2663    0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674   -1.2149    1.1351 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4984    0.2256    0.7561 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3079   -0.2932    1.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6093    0.4679    1.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3857    2.1795    2.1871 S   0  0  0  0  0  6  0  0  0  0  0  0
    9.7620    2.7783    2.3701 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7115    2.9228    1.0993 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6005    2.3281    3.6691 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8265   -0.5489   -1.8882 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7304   -2.0185   -2.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6946   -2.4357   -1.8502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118   -1.1323   -1.4631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5508   -1.1884   -0.6816 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7039   -1.4777   -1.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8254   -0.5032   -1.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2439   -0.2058   -0.1066 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0851    1.0762   -0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6656    1.4437    1.1492 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0344    2.8064    1.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6362    1.3462    2.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2779    1.3159    1.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0649    0.0273    0.8105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8488   -1.0734    1.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8424    0.1551   -0.0521 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6797    0.7424    0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5474    0.8956   -0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1297   -0.4656   -0.7509 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2000   -1.3786    0.4045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0483    0.0463   -3.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1966   -1.1778   -3.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6058    0.6274   -3.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0987    1.1061   -1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3032   -1.5471   -0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5681   -0.3092    0.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1585    1.3446   -0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8728    0.3034   -1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8413    1.0070    0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7957   -0.3046    2.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5389   -1.3657    1.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2511    0.0178    2.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1830    0.3783    0.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8414    3.2212    4.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3033   -0.0346   -2.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7884   -2.1818   -3.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4838   -2.6383   -1.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2247   -2.9320   -2.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6409   -3.1588   -1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4949   -0.5651   -2.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5912   -2.0113    0.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3589   -1.4385   -2.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1156   -2.4946   -1.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6637    0.4337   -2.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7200   -0.9830   -2.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8946   -1.0097    0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5296    1.8934   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9377    0.8184   -0.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5659    0.8757    1.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0067    2.9246    1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6492    2.2337    2.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8672    0.4713    2.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4764    1.4574    2.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2373    2.1883    0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3077   -1.9973    1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7704   -1.2249    2.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3536   -0.8983    2.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1048    0.8657   -0.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3610    0.1825    1.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9440    1.7668    0.9767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9737    1.4226   -1.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167    1.5057    0.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0043   -2.1199    0.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4659   -0.8081    1.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -2.0134    0.7125 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
 32 33  1  1
 32 14  1  0
 32 17  1  0
 29 18  1  0
 27 21  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  1
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
 13 47  1  0
 14 48  1  6
 15 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 17 53  1  6
 18 54  1  1
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  1
 22 60  1  0
 22 61  1  0
 23 62  1  1
 24 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 28 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  6
 30 72  1  0
 30 73  1  0
 31 74  1  0
 31 75  1  0
 33 76  1  0
 33 77  1  0
 33 78  1  0
M  END


  Mrv1652309152018592D          

 38 41  0  0  0  0            999 V2000
 9998.933710001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7957 9999.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6538 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2209 9999.7851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5083 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9337 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7957 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7940 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.7940 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.5085 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2230 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.221410000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.506910000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5069 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.2214 9998.9659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.0818 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3673 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3673 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.0818 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.935910000.2033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9359 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.7205 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.2054 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.720510000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.720510001.2833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.434510001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.005910001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.150210001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.863910001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.579510001.2833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.863910002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.293210001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.008910001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.724510001.6958    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10005.137010002.4115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.312010002.4115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.440210001.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.434510000.8708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  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
 18  3  1  6  0  0  0
 19  9  1  0  0  0  0
  9  7  1  1  0  0  0
 16  8  1  0  0  0  0
  8  2  1  1  0  0  0
 14  8  1  0  0  0  0
 14  5  1  6  0  0  0
 11 15  1  0  0  0  0
 15  4  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 24 38  1  6  0  0  0
 25 26  1  0  0  0  0
 25 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  2  0  0  0  0
 34 37  1  0  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
 15 21  1  0  0  0  0
 21  6  1  6  0  0  0
 12 20  1  0  0  0  0
 20  1  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000146

> <DATABASE_NAME>
MIME

> <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])CC[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H45NO5S/c1-17(4-9-24(29)27-14-15-33(30,31)32)21-7-8-22-20-6-5-18-16-19(28)10-12-25(18,2)23(20)11-13-26(21,22)3/h17-23,28H,4-16H2,1-3H3,(H,27,29)(H,30,31,32)/t17-,18-,19-,20+,21-,22+,23+,25+,26-/m1/s1

> <INCHI_KEY>
QBYUNVOYXHFVKC-GBURMNQMSA-N

> <FORMULA>
C26H45NO5S

> <MOLECULAR_WEIGHT>
483.71

> <EXACT_MASS>
483.301844727

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
55.84601914016565

> <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)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
2.4811742052517807

> <ALOGPS_LOGS>
-6.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.60199909179077

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.6276888737017137

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1127164403915377

> <JCHEM_POLAR_SURFACE_AREA>
103.69999999999999

> <JCHEM_REFRACTIVITY>
129.08649999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.77e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000722
     RDKit          3D
Lithocholyltaurine
 78 81  0  0  0  0  0  0  0  0999 V2000
    2.8472   -0.1611   -3.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538    0.0022   -1.7833 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0557   -0.4907   -0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3676    0.2627   -0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2014   -0.2663    0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674   -1.2149    1.1351 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4984    0.2256    0.7561 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3079   -0.2932    1.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6093    0.4679    1.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3857    2.1795    2.1871 S   0  0  0  0  0  6  0  0  0  0  0  0
    9.7620    2.7783    2.3701 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7115    2.9228    1.0993 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6005    2.3281    3.6691 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8265   -0.5489   -1.8882 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7304   -2.0185   -2.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6946   -2.4357   -1.8502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118   -1.1323   -1.4631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5508   -1.1884   -0.6816 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7039   -1.4777   -1.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8254   -0.5032   -1.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2439   -0.2058   -0.1066 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0851    1.0762   -0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6656    1.4437    1.1492 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0344    2.8064    1.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6362    1.3462    2.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2779    1.3159    1.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0649    0.0273    0.8105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8488   -1.0734    1.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8424    0.1551   -0.0521 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6797    0.7424    0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5474    0.8956   -0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1297   -0.4656   -0.7509 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2000   -1.3786    0.4045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0483    0.0463   -3.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1966   -1.1778   -3.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6058    0.6274   -3.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0987    1.1061   -1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3032   -1.5471   -0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5681   -0.3092    0.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1585    1.3446   -0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8728    0.3034   -1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8413    1.0070    0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7957   -0.3046    2.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5389   -1.3657    1.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2511    0.0178    2.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1830    0.3783    0.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8414    3.2212    4.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3033   -0.0346   -2.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7884   -2.1818   -3.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4838   -2.6383   -1.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2247   -2.9320   -2.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6409   -3.1588   -1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4949   -0.5651   -2.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5912   -2.0113    0.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3589   -1.4385   -2.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1156   -2.4946   -1.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6637    0.4337   -2.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7200   -0.9830   -2.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8946   -1.0097    0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5296    1.8934   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9377    0.8184   -0.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5659    0.8757    1.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0067    2.9246    1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6492    2.2337    2.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8672    0.4713    2.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4764    1.4574    2.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2373    2.1883    0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3077   -1.9973    1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7704   -1.2249    2.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3536   -0.8983    2.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1048    0.8657   -0.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3610    0.1825    1.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9440    1.7668    0.9767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9737    1.4226   -1.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167    1.5057    0.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0043   -2.1199    0.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4659   -0.8081    1.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -2.0134    0.7125 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
 32 33  1  1
 32 14  1  0
 32 17  1  0
 29 18  1  0
 27 21  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  1
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
 13 47  1  0
 14 48  1  6
 15 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 17 53  1  6
 18 54  1  1
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  1
 22 60  1  0
 22 61  1  0
 23 62  1  1
 24 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 28 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  6
 30 72  1  0
 30 73  1  0
 31 74  1  0
 31 75  1  0
 33 76  1  0
 33 77  1  0
 33 78  1  0
M  END

HEADER    PROTEIN                                 15-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-SEP-20         0                                  
HETATM    1  C   UNK     0    8664.6768668.598   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.6858666.266   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8656.6878662.405   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8663.3468666.266   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8662.0158663.961   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8664.6768663.961   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8660.6858661.633   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0    8660.6828664.719   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8660.6828663.179   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.0168662.409   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8663.3508663.179   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8663.3478667.816   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.0138667.046   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8662.0138665.506   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.3478664.736   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8659.3538665.489   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8658.0198664.719   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8658.0198663.179   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8659.3538662.409   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8664.6808667.046   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8664.6808665.506   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8666.1458665.030   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8667.0508666.276   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8666.1458667.522   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8666.1458669.062   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8667.4788669.832   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8664.8118669.832   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8668.8148669.062   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8670.1468669.832   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0    8671.4828669.062   0.000  0.00  0.00           N+0
HETATM   31  O   UNK     0    8670.1468671.372   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0    8672.8148669.832   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8674.1508669.062   0.000  0.00  0.00           C+0
HETATM   34  S   UNK     0    8675.4868669.832   0.000  0.00  0.00           S+0
HETATM   35  O   UNK     0    8676.2568671.168   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0    8674.7168671.168   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0    8676.8228669.062   0.000  0.00  0.00           O+0
HETATM   38  H   UNK     0    8667.4788668.292   0.000  0.00  0.00           H+0
CONECT    1   20                                                            
CONECT    2    8                                                            
CONECT    3   18                                                            
CONECT    4   15                                                            
CONECT    5   14                                                            
CONECT    6   21                                                            
CONECT    7    9                                                            
CONECT    8    9   16    2   14                                             
CONECT    9    8   10   19    7                                             
CONECT   10    9   11                                                       
CONECT   11   10   15                                                       
CONECT   12   13   20                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15    8    5                                             
CONECT   15   14   11    4   21                                             
CONECT   16   17    8                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19    3                                                  
CONECT   19   18    9                                                       
CONECT   20   21   24   12    1                                             
CONECT   21   20   22   15    6                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   25   38   20   23                                             
CONECT   25   24   26   27                                                  
CONECT   26   25   28                                                       
CONECT   27   25                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29   32                                                       
CONECT   31   29                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36   37                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   34                                                            
CONECT   38   24                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

COMPND    HMDB0000722
HETATM    1  C1  UNL     1       2.847  -0.161  -3.142  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.154   0.002  -1.783  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.056  -0.491  -0.699  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.368   0.263  -0.643  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.201  -0.266   0.435  1.00  0.00           C  
HETATM    6  O1  UNL     1       4.767  -1.215   1.135  1.00  0.00           O  
HETATM    7  N1  UNL     1       6.498   0.226   0.756  1.00  0.00           N  
HETATM    8  C6  UNL     1       7.308  -0.293   1.807  1.00  0.00           C  
HETATM    9  C7  UNL     1       8.609   0.468   1.868  1.00  0.00           C  
HETATM   10  S1  UNL     1       8.386   2.179   2.187  1.00  0.00           S  
HETATM   11  O2  UNL     1       9.762   2.778   2.370  1.00  0.00           O  
HETATM   12  O3  UNL     1       7.711   2.923   1.099  1.00  0.00           O  
HETATM   13  O4  UNL     1       7.600   2.328   3.669  1.00  0.00           O  
HETATM   14  C8  UNL     1       0.827  -0.549  -1.888  1.00  0.00           C  
HETATM   15  C9  UNL     1       0.730  -2.019  -2.251  1.00  0.00           C  
HETATM   16  C10 UNL     1      -0.695  -2.436  -1.850  1.00  0.00           C  
HETATM   17  C11 UNL     1      -1.312  -1.132  -1.463  1.00  0.00           C  
HETATM   18  C12 UNL     1      -2.551  -1.188  -0.682  1.00  0.00           C  
HETATM   19  C13 UNL     1      -3.704  -1.478  -1.635  1.00  0.00           C  
HETATM   20  C14 UNL     1      -4.825  -0.503  -1.516  1.00  0.00           C  
HETATM   21  C15 UNL     1      -5.244  -0.206  -0.107  1.00  0.00           C  
HETATM   22  C16 UNL     1      -6.085   1.076  -0.173  1.00  0.00           C  
HETATM   23  C17 UNL     1      -6.666   1.444   1.149  1.00  0.00           C  
HETATM   24  O5  UNL     1      -7.034   2.806   1.079  1.00  0.00           O  
HETATM   25  C18 UNL     1      -5.636   1.346   2.249  1.00  0.00           C  
HETATM   26  C19 UNL     1      -4.278   1.316   1.597  1.00  0.00           C  
HETATM   27  C20 UNL     1      -4.065   0.027   0.811  1.00  0.00           C  
HETATM   28  C21 UNL     1      -3.849  -1.073   1.795  1.00  0.00           C  
HETATM   29  C22 UNL     1      -2.842   0.155  -0.052  1.00  0.00           C  
HETATM   30  C23 UNL     1      -1.680   0.742   0.674  1.00  0.00           C  
HETATM   31  C24 UNL     1      -0.547   0.896  -0.351  1.00  0.00           C  
HETATM   32  C25 UNL     1      -0.130  -0.466  -0.751  1.00  0.00           C  
HETATM   33  C26 UNL     1       0.200  -1.379   0.404  1.00  0.00           C  
HETATM   34  H1  UNL     1       2.048   0.046  -3.906  1.00  0.00           H  
HETATM   35  H2  UNL     1       3.197  -1.178  -3.311  1.00  0.00           H  
HETATM   36  H3  UNL     1       3.606   0.627  -3.300  1.00  0.00           H  
HETATM   37  H4  UNL     1       2.099   1.106  -1.648  1.00  0.00           H  
HETATM   38  H5  UNL     1       3.303  -1.547  -0.740  1.00  0.00           H  
HETATM   39  H6  UNL     1       2.568  -0.309   0.293  1.00  0.00           H  
HETATM   40  H7  UNL     1       4.159   1.345  -0.387  1.00  0.00           H  
HETATM   41  H8  UNL     1       4.873   0.303  -1.625  1.00  0.00           H  
HETATM   42  H9  UNL     1       6.841   1.007   0.163  1.00  0.00           H  
HETATM   43  H10 UNL     1       6.796  -0.305   2.783  1.00  0.00           H  
HETATM   44  H11 UNL     1       7.539  -1.366   1.537  1.00  0.00           H  
HETATM   45  H12 UNL     1       9.251   0.018   2.657  1.00  0.00           H  
HETATM   46  H13 UNL     1       9.183   0.378   0.914  1.00  0.00           H  
HETATM   47  H14 UNL     1       7.841   3.221   4.062  1.00  0.00           H  
HETATM   48  H15 UNL     1       0.303  -0.035  -2.754  1.00  0.00           H  
HETATM   49  H16 UNL     1       0.788  -2.182  -3.342  1.00  0.00           H  
HETATM   50  H17 UNL     1       1.484  -2.638  -1.772  1.00  0.00           H  
HETATM   51  H18 UNL     1      -1.225  -2.932  -2.661  1.00  0.00           H  
HETATM   52  H19 UNL     1      -0.641  -3.159  -1.001  1.00  0.00           H  
HETATM   53  H20 UNL     1      -1.495  -0.565  -2.416  1.00  0.00           H  
HETATM   54  H21 UNL     1      -2.591  -2.011   0.076  1.00  0.00           H  
HETATM   55  H22 UNL     1      -3.359  -1.439  -2.710  1.00  0.00           H  
HETATM   56  H23 UNL     1      -4.116  -2.495  -1.508  1.00  0.00           H  
HETATM   57  H24 UNL     1      -4.664   0.434  -2.125  1.00  0.00           H  
HETATM   58  H25 UNL     1      -5.720  -0.983  -2.013  1.00  0.00           H  
HETATM   59  H26 UNL     1      -5.895  -1.010   0.255  1.00  0.00           H  
HETATM   60  H27 UNL     1      -5.530   1.893  -0.665  1.00  0.00           H  
HETATM   61  H28 UNL     1      -6.938   0.818  -0.860  1.00  0.00           H  
HETATM   62  H29 UNL     1      -7.566   0.876   1.381  1.00  0.00           H  
HETATM   63  H30 UNL     1      -8.007   2.925   1.237  1.00  0.00           H  
HETATM   64  H31 UNL     1      -5.649   2.234   2.920  1.00  0.00           H  
HETATM   65  H32 UNL     1      -5.867   0.471   2.854  1.00  0.00           H  
HETATM   66  H33 UNL     1      -3.476   1.457   2.324  1.00  0.00           H  
HETATM   67  H34 UNL     1      -4.237   2.188   0.894  1.00  0.00           H  
HETATM   68  H35 UNL     1      -4.308  -1.997   1.387  1.00  0.00           H  
HETATM   69  H36 UNL     1      -2.770  -1.225   2.050  1.00  0.00           H  
HETATM   70  H37 UNL     1      -4.354  -0.898   2.780  1.00  0.00           H  
HETATM   71  H38 UNL     1      -3.105   0.866  -0.883  1.00  0.00           H  
HETATM   72  H39 UNL     1      -1.361   0.182   1.557  1.00  0.00           H  
HETATM   73  H40 UNL     1      -1.944   1.767   0.977  1.00  0.00           H  
HETATM   74  H41 UNL     1      -0.974   1.423  -1.210  1.00  0.00           H  
HETATM   75  H42 UNL     1       0.217   1.506   0.132  1.00  0.00           H  
HETATM   76  H43 UNL     1       1.004  -2.120   0.141  1.00  0.00           H  
HETATM   77  H44 UNL     1       0.466  -0.808   1.334  1.00  0.00           H  
HETATM   78  H45 UNL     1      -0.659  -2.013   0.712  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3   14   37
CONECT    3    4   38   39
CONECT    4    5   40   41
CONECT    5    6    6    7
CONECT    7    8   42
CONECT    8    9   43   44
CONECT    9   10   45   46
CONECT   10   11   11   12   12
CONECT   10   13
CONECT   13   47
CONECT   14   15   32   48
CONECT   15   16   49   50
CONECT   16   17   51   52
CONECT   17   18   32   53
CONECT   18   19   29   54
CONECT   19   20   55   56
CONECT   20   21   57   58
CONECT   21   22   27   59
CONECT   22   23   60   61
CONECT   23   24   25   62
CONECT   24   63
CONECT   25   26   64   65
CONECT   26   27   66   67
CONECT   27   28   29
CONECT   28   68   69   70
CONECT   29   30   71
CONECT   30   31   72   73
CONECT   31   32   74   75
CONECT   32   33
CONECT   33   76   77   78
END

HMDB0000722
     RDKit          3D
Lithocholyltaurine
 78 81  0  0  0  0  0  0  0  0999 V2000
    2.8472   -0.1611   -3.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538    0.0022   -1.7833 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0557   -0.4907   -0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3676    0.2627   -0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2014   -0.2663    0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674   -1.2149    1.1351 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4984    0.2256    0.7561 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3079   -0.2932    1.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6093    0.4679    1.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3857    2.1795    2.1871 S   0  0  0  0  0  6  0  0  0  0  0  0
    9.7620    2.7783    2.3701 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7115    2.9228    1.0993 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6005    2.3281    3.6691 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8265   -0.5489   -1.8882 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7304   -2.0185   -2.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6946   -2.4357   -1.8502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118   -1.1323   -1.4631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5508   -1.1884   -0.6816 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7039   -1.4777   -1.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8254   -0.5032   -1.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2439   -0.2058   -0.1066 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0851    1.0762   -0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6656    1.4437    1.1492 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0344    2.8064    1.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6362    1.3462    2.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2779    1.3159    1.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0649    0.0273    0.8105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8488   -1.0734    1.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8424    0.1551   -0.0521 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6797    0.7424    0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5474    0.8956   -0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1297   -0.4656   -0.7509 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2000   -1.3786    0.4045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0483    0.0463   -3.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1966   -1.1778   -3.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6058    0.6274   -3.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0987    1.1061   -1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3032   -1.5471   -0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5681   -0.3092    0.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1585    1.3446   -0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8728    0.3034   -1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8413    1.0070    0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7957   -0.3046    2.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5389   -1.3657    1.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2511    0.0178    2.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1830    0.3783    0.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8414    3.2212    4.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3033   -0.0346   -2.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7884   -2.1818   -3.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4838   -2.6383   -1.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2247   -2.9320   -2.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6409   -3.1588   -1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4949   -0.5651   -2.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5912   -2.0113    0.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3589   -1.4385   -2.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1156   -2.4946   -1.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6637    0.4337   -2.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7200   -0.9830   -2.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8946   -1.0097    0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5296    1.8934   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9377    0.8184   -0.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5659    0.8757    1.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0067    2.9246    1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6492    2.2337    2.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8672    0.4713    2.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4764    1.4574    2.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2373    2.1883    0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3077   -1.9973    1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7704   -1.2249    2.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3536   -0.8983    2.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1048    0.8657   -0.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3610    0.1825    1.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9440    1.7668    0.9767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9737    1.4226   -1.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167    1.5057    0.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0043   -2.1199    0.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4659   -0.8081    1.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -2.0134    0.7125 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
 32 33  1  1
 32 14  1  0
 32 17  1  0
 29 18  1  0
 27 21  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  1
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
 13 47  1  0
 14 48  1  6
 15 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 17 53  1  6
 18 54  1  1
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  1
 22 60  1  0
 22 61  1  0
 23 62  1  1
 24 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 28 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  6
 30 72  1  0
 30 73  1  0
 31 74  1  0
 31 75  1  0
 33 76  1  0
 33 77  1  0
 33 78  1  0
M  END

Synonyms

Value	Source
Taurolithocholate	ChEBI
Taurolithocholic acid	Kegg
Taurine lithocholate	HMDB
Acid, taurolithocholic	HMDB
Taurolithocholic acid, monosodium salt	HMDB
Lithocholate, taurine	HMDB
3alpha-Hydroxy-5beta-cholanoyltaurine	HMDB
3alpha-Hydroxy-N-(2-sulfoethyl)-5beta-cholan-24-amide	HMDB
3Α-hydroxy-5β-cholanoyltaurine	HMDB
3Α-hydroxy-N-(2-sulfoethyl)-5β-cholan-24-amide	HMDB
Lithocholic acid taurine conjugate	HMDB
Lithocholyltaurine	ChEBI

Molecular Formula

C₂₆H₄₅NO₅S

Average Mass

483.71

Monoisotopic Mass

483.301844727

IUPAC Name

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

CAS Registry Number

516-90-5

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])CC[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O

InChI Identifier

InChI=1S/C26H45NO5S/c1-17(4-9-24(29)27-14-15-33(30,31)32)21-7-8-22-20-6-5-18-16-19(28)10-12-25(18,2)23(20)11-13-26(21,22)3/h17-23,28H,4-16H2,1-3H3,(H,27,29)(H,30,31,32)/t17-,18-,19-,20+,21-,22+,23+,25+,26-/m1/s1

InChI Key

QBYUNVOYXHFVKC-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
Hydroxy bile acid, alcohol, or derivatives
Monohydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
Fatty amide
N-acyl-amine
Fatty acyl
Sulfonyl
Organosulfonic acid
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Alkanesulfonic acid
Cyclic alcohol
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organosulfur compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:36259 )
bile acid taurine conjugate (CHEBI:36259 )
C26 bile acids, alcohols, and derivatives (C02592 )
Taurine conjugates (C02592 )
Taurine conjugates (LMST05040003 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00028 g/L	ALOGPS
logP	2.1	ALOGPS
logP	2.48	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	-0.63	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.7 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	129.09 m³·mol⁻¹	ChemAxon
Polarizability	55.85 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

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Bile
Blood
Feces
Gall Bladder
Intestine
Urine

Tissue Locations

Gall Bladder
Intestine

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	4	Human ; Human feces; Human saliva; Human mucosa	Microbial culture
Bacteria/Eubacteria	Proteobacteria	1	Human ; Human feces	Microbial culture
Bacteria/Eubacteria	Actinobacteria	3	Human feces; Human ; Human saliva; Human mucosa	Microbial culture

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Feces	Detected and Quantified	0.51	0.40			nmol/g dry feces	Not Specified	Not Specified	Normal	HMDB	22664055
Human Blood	Detected and Quantified	0.614	0.013			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	16182619
Human Blood	Detected and Quantified	1.810	0.002			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	16182619
Human Bile	Detected and Quantified	370.0		350.0	380.0	uM	Adult (>18 years old)	Both	Normal	HMDB	16548228
Human Gall bladder	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
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

HMDB0000722

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022203

KNApSAcK ID

Not Available

Chemspider ID

388820

KEGG Compound ID

C02592

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Taurolithocholic_acid

METLIN ID

5690

PubChem Compound

439763

PDB ID

Not Available

ChEBI ID

36259

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Lee BL, New AL, Ong CN: Comparative analysis of conjugated bile acids in human serum using high-performance liquid chromatography and capillary electrophoresis. J Chromatogr B Biomed Sci Appl. 1997 Dec 19;704(1-2):35-42. doi: 10.1016/s0378-4347(97)00443-x. [PubMed:9518169 ]
Crocenzi FA, Basiglio CL, Perez LM, Portesio MS, Pozzi EJ, Roma MG: Silibinin prevents cholestasis-associated retrieval of the bile salt export pump, Bsep, in isolated rat hepatocyte couplets: possible involvement of cAMP. Biochem Pharmacol. 2005 Apr 1;69(7):1113-20. doi: 10.1016/j.bcp.2005.01.009. [PubMed:15763547 ]
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 ]
Tadano T, Kanoh M, Matsumoto M, Sakamoto K, Kamano T: Studies of serum and feces bile acids determination by gas chromatography-mass spectrometry. Rinsho Byori. 2006 Feb;54(2):103-10. [PubMed:16548228 ]
Watanabe N, Kagawa T, Kojima S, Takashimizu S, Nagata N, Nishizaki Y, Mine T: Taurolithocholate impairs bile canalicular motility and canalicular bile secretion in isolated rat hepatocyte couplets. World J Gastroenterol. 2006 Sep 7;12(33):5320-5. doi: 10.3748/wjg.v12.i33.5320. [PubMed:16981261 ]
Pusl T, Vennegeerts T, Wimmer R, Denk GU, Beuers U, Rust C: Tauroursodeoxycholic acid reduces bile acid-induced apoptosis by modulation of AP-1. Biochem Biophys Res Commun. 2008 Feb 29;367(1):208-12. doi: 10.1016/j.bbrc.2007.12.122. Epub 2007 Dec 27. [PubMed:18164257 ]

Showing metabocard for Lithocholyltaurine (MMDBc0000146)

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