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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (8) Show 9 proteins XML

enzymes (1)transporters (8) Show 9 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:05 UTC

HMDB ID

HMDB0000686

Secondary Accession Numbers

HMDB00686

Metabolite Identification

Common Name

Isoursodeoxycholic acid

Description

Isoursodeoxycholic acid is a bile acid. 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


  Mrv1652302052016242D          

 33 36  0  0  0  0            999 V2000
10000.340010001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9999.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3421 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0597 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9142 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6270 9999.7851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.3400 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4883 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.1317    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.4883 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.627510000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.913010000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9130 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6275 9998.9659    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.2002 9998.9568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.2002 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9147 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6292 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.342010000.2033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3420 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1266 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6115 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.126610000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.126610001.2833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.842310001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.555910001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.271610001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.985210001.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.271610002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.412910001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.842310000.8708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11  4  1  1  0  0  0
 20  3  1  1  0  0  0
 12 18  1  0  0  0  0
 18  5  1  1  0  0  0
  9 17  1  0  0  0  0
 17  2  1  1  0  0  0
 15 17  1  0  0  0  0
 15  6  1  6  0  0  0
 20 16  1  0  0  0  0
 16  7  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 25 33  1  6  0  0  0
 26 27  1  0  0  0  0
 26 32  1  6  0  0  0
 27 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
 25 21  1  0  0  0  0
 25 24  1  0  0  0  0
 16 22  1  0  0  0  0
 22  8  1  6  0  0  0
 13 21  1  0  0  0  0
 21  1  1  1  0  0  0
M  END

HMDB0000686
     RDKit          3D
Isoursodeoxycholic acid
 68 71  0  0  0  0  0  0  0  0999 V2000
    4.0712    0.9472    0.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7340   -0.2011   -0.3323 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9223   -0.6107   -1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0518   -1.1283   -0.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6843   -0.2719    0.6951 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3519   -0.3638    1.9024 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6715    0.6788    0.3926 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4909    0.1107   -1.1245 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1377   -1.0006   -2.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1324   -1.7996   -1.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2505   -0.6260   -0.9441 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9361   -0.7932   -0.1173 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9727   -1.6967   -0.8591 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4219   -2.9495   -1.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1009   -1.8901    0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7872   -0.5854    0.4553 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6308   -0.1764   -0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5739    0.9424   -0.3181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8221    0.4286    0.0221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0262    1.6488    0.9047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5187    1.8181    0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8017    0.4832    0.8795 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4029    0.1469    2.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6240    0.5463   -0.0477 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7355    1.7029    0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5917    1.6653   -0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2496    0.3148   -0.2893 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4014    0.1424    1.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0787    1.3970    0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4036    1.8405    0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9585    0.7722    1.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5247   -1.1384    0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6536   -1.5038   -1.7815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2856    0.2179   -1.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7644   -2.1333    0.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9157   -1.4585   -0.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4694    1.2977   -0.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6700    1.0457   -1.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9122   -1.5770   -2.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4817   -0.5190   -2.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5977   -2.2003   -0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6854   -2.5163   -1.9151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0671   -0.1801   -1.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8332   -1.3175    0.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2998   -1.1922   -1.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9586   -3.2447   -0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6678   -2.3757    1.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8556   -2.5615   -0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4575   -0.7630    1.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0202    0.1148   -1.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2437   -1.0454   -1.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6609    1.6622   -1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2716    1.1413    0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3232    1.1778    1.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4474    2.6811    0.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130    2.4024    1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2742    2.3995   -0.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1289   -0.9125    2.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2986    0.2940    2.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6127    0.7767    2.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0778    0.6899   -1.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5894    1.8282    1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2509    2.6307   -0.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2091    2.4404   -0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253    1.8558   -1.5767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6237    1.1622    1.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0527   -0.6488    1.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3534   -0.0229    1.5869 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
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27  8  1  0
 27 11  1  0
 24 12  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  6
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  6
 12 44  1  1
 13 45  1  6
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  1
 17 50  1  0
 17 51  1  0
 18 52  1  6
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 23 58  1  0
 23 59  1  0
 23 60  1  0
 24 61  1  6
 25 62  1  0
 25 63  1  0
 26 64  1  0
 26 65  1  0
 28 66  1  0
 28 67  1  0
 28 68  1  0
M  END


  Mrv1652302052016242D          

 33 36  0  0  0  0            999 V2000
10000.340010001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9999.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3421 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0597 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9142 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6270 9999.7851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.3400 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4883 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.1317    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.4883 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.627510000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.913010000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9130 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6275 9998.9659    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.2002 9998.9568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.2002 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9147 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6292 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.342010000.2033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3420 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1266 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6115 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.126610000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.126610001.2833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.842310001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.555910001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.271610001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.985210001.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.271610002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.412910001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.842310000.8708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11  4  1  1  0  0  0
 20  3  1  1  0  0  0
 12 18  1  0  0  0  0
 18  5  1  1  0  0  0
  9 17  1  0  0  0  0
 17  2  1  1  0  0  0
 15 17  1  0  0  0  0
 15  6  1  6  0  0  0
 20 16  1  0  0  0  0
 16  7  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 25 33  1  6  0  0  0
 26 27  1  0  0  0  0
 26 32  1  6  0  0  0
 27 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
 25 21  1  0  0  0  0
 25 24  1  0  0  0  0
 16 22  1  0  0  0  0
 22  8  1  6  0  0  0
 13 21  1  0  0  0  0
 21  1  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0000686

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16+,17-,18+,19+,20+,22+,23+,24-/m1/s1

> <INCHI_KEY>
RUDATBOHQWOJDD-DNMBCGTGSA-N

> <FORMULA>
C24H40O4

> <MOLECULAR_WEIGHT>
392.572

> <EXACT_MASS>
392.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
46.71924296082756

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2S,5S,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
3.7133055236666674

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.296339908541825

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.595945733487658

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5356636301705279

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
109.27379999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2S,5S,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000686
     RDKit          3D
Isoursodeoxycholic acid
 68 71  0  0  0  0  0  0  0  0999 V2000
    4.0712    0.9472    0.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7340   -0.2011   -0.3323 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9223   -0.6107   -1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0518   -1.1283   -0.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6843   -0.2719    0.6951 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3519   -0.3638    1.9024 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6715    0.6788    0.3926 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4909    0.1107   -1.1245 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1377   -1.0006   -2.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1324   -1.7996   -1.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2505   -0.6260   -0.9441 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9361   -0.7932   -0.1173 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9727   -1.6967   -0.8591 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4219   -2.9495   -1.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1009   -1.8901    0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7872   -0.5854    0.4553 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6308   -0.1764   -0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5739    0.9424   -0.3181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8221    0.4286    0.0221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0262    1.6488    0.9047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5187    1.8181    0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8017    0.4832    0.8795 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4029    0.1469    2.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6240    0.5463   -0.0477 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7355    1.7029    0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5917    1.6653   -0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2496    0.3148   -0.2893 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4014    0.1424    1.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0787    1.3970    0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4036    1.8405    0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9585    0.7722    1.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5247   -1.1384    0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6536   -1.5038   -1.7815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2856    0.2179   -1.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7644   -2.1333    0.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9157   -1.4585   -0.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4694    1.2977   -0.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6700    1.0457   -1.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9122   -1.5770   -2.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4817   -0.5190   -2.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5977   -2.2003   -0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6854   -2.5163   -1.9151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0671   -0.1801   -1.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8332   -1.3175    0.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2998   -1.1922   -1.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9586   -3.2447   -0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6678   -2.3757    1.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8556   -2.5615   -0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4575   -0.7630    1.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0202    0.1148   -1.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2437   -1.0454   -1.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6609    1.6622   -1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2716    1.1413    0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3232    1.1778    1.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4474    2.6811    0.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130    2.4024    1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2742    2.3995   -0.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1289   -0.9125    2.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2986    0.2940    2.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6127    0.7767    2.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0778    0.6899   -1.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5894    1.8282    1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2509    2.6307   -0.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2091    2.4404   -0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253    1.8558   -1.5767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6237    1.1622    1.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0527   -0.6488    1.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3534   -0.0229    1.5869 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
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27  8  1  0
 27 11  1  0
 24 12  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  6
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  6
 12 44  1  1
 13 45  1  6
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  1
 17 50  1  0
 17 51  1  0
 18 52  1  6
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 23 58  1  0
 23 59  1  0
 23 60  1  0
 24 61  1  6
 25 62  1  0
 25 63  1  0
 26 64  1  0
 26 65  1  0
 28 66  1  0
 28 67  1  0
 28 68  1  0
M  END

HEADER    PROTEIN                                 05-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-FEB-20         0                                  
HETATM    1  C   UNK     0    8667.3018668.598   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8663.3108666.266   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8667.3058662.405   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8659.3118662.405   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8663.3108661.633   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8664.6408663.961   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8665.9708666.266   0.000  0.00  0.00           H+0
HETATM    8  H   UNK     0    8667.3018663.961   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0    8661.9788665.489   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8660.6448664.719   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8660.6448663.179   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.9788662.409   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.9718667.816   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.6388667.046   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.6388665.506   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.9718664.736   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8663.3078664.719   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.3078663.179   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.6418662.409   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8665.9758663.179   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8667.3058667.046   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8667.3058665.506   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.7708665.030   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8669.6758666.276   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8668.7708667.522   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8668.7708669.062   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8670.1068669.832   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8671.4388669.062   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8672.7748669.832   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0    8674.1068669.062   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0    8672.7748671.372   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0    8667.4378669.832   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0    8670.1068668.292   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2   17                                                            
CONECT    3   20                                                            
CONECT    4   11                                                            
CONECT    5   18                                                            
CONECT    6   15                                                            
CONECT    7   16                                                            
CONECT    8   22                                                            
CONECT    9   10   17                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    4                                                  
CONECT   12   11   18                                                       
CONECT   13   14   21                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17    6                                             
CONECT   16   15   20    7   22                                             
CONECT   17   18    9    2   15                                             
CONECT   18   17   19   12    5                                             
CONECT   19   18   20                                                       
CONECT   20   19    3   16                                                  
CONECT   21   22   25   13    1                                             
CONECT   22   21   23   16    8                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   26   33   21   24                                             
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   26                                                            
CONECT   33   25                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0000686
HETATM    1  C1  UNL     1       4.071   0.947   0.578  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.734  -0.201  -0.332  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.922  -0.611  -1.123  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.052  -1.128  -0.295  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.684  -0.272   0.695  1.00  0.00           C  
HETATM    6  O1  UNL     1       6.352  -0.364   1.902  1.00  0.00           O  
HETATM    7  O2  UNL     1       7.671   0.679   0.393  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.491   0.111  -1.124  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.138  -1.001  -2.090  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.132  -1.800  -1.229  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.251  -0.626  -0.944  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.936  -0.793  -0.117  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.973  -1.697  -0.859  1.00  0.00           C  
HETATM   14  O3  UNL     1      -1.422  -2.950  -1.077  1.00  0.00           O  
HETATM   15  C12 UNL     1      -3.101  -1.890   0.154  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.787  -0.585   0.455  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.631  -0.176  -0.707  1.00  0.00           C  
HETATM   18  C15 UNL     1      -5.574   0.942  -0.318  1.00  0.00           C  
HETATM   19  O4  UNL     1      -6.822   0.429   0.022  1.00  0.00           O  
HETATM   20  C16 UNL     1      -5.026   1.649   0.905  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.519   1.818   0.817  1.00  0.00           C  
HETATM   22  C18 UNL     1      -2.802   0.483   0.880  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.403   0.147   2.298  1.00  0.00           C  
HETATM   24  C20 UNL     1      -1.624   0.546  -0.048  1.00  0.00           C  
HETATM   25  C21 UNL     1      -0.736   1.703   0.200  1.00  0.00           C  
HETATM   26  C22 UNL     1       0.592   1.665  -0.507  1.00  0.00           C  
HETATM   27  C23 UNL     1       1.250   0.315  -0.289  1.00  0.00           C  
HETATM   28  C24 UNL     1       1.401   0.142   1.172  1.00  0.00           C  
HETATM   29  H1  UNL     1       5.079   1.397   0.308  1.00  0.00           H  
HETATM   30  H2  UNL     1       3.404   1.840   0.356  1.00  0.00           H  
HETATM   31  H3  UNL     1       3.959   0.772   1.640  1.00  0.00           H  
HETATM   32  H4  UNL     1       3.525  -1.138   0.319  1.00  0.00           H  
HETATM   33  H5  UNL     1       4.654  -1.504  -1.782  1.00  0.00           H  
HETATM   34  H6  UNL     1       5.286   0.218  -1.798  1.00  0.00           H  
HETATM   35  H7  UNL     1       5.764  -2.133   0.155  1.00  0.00           H  
HETATM   36  H8  UNL     1       6.916  -1.459  -0.980  1.00  0.00           H  
HETATM   37  H9  UNL     1       7.469   1.298  -0.393  1.00  0.00           H  
HETATM   38  H10 UNL     1       2.670   1.046  -1.690  1.00  0.00           H  
HETATM   39  H11 UNL     1       2.912  -1.577  -2.519  1.00  0.00           H  
HETATM   40  H12 UNL     1       1.482  -0.519  -2.863  1.00  0.00           H  
HETATM   41  H13 UNL     1       1.598  -2.200  -0.331  1.00  0.00           H  
HETATM   42  H14 UNL     1       0.685  -2.516  -1.915  1.00  0.00           H  
HETATM   43  H15 UNL     1      -0.067  -0.180  -1.925  1.00  0.00           H  
HETATM   44  H16 UNL     1      -0.833  -1.317   0.841  1.00  0.00           H  
HETATM   45  H17 UNL     1      -2.300  -1.192  -1.767  1.00  0.00           H  
HETATM   46  H18 UNL     1      -0.959  -3.245  -0.258  1.00  0.00           H  
HETATM   47  H19 UNL     1      -2.668  -2.376   1.042  1.00  0.00           H  
HETATM   48  H20 UNL     1      -3.856  -2.561  -0.307  1.00  0.00           H  
HETATM   49  H21 UNL     1      -4.458  -0.763   1.328  1.00  0.00           H  
HETATM   50  H22 UNL     1      -4.020   0.115  -1.573  1.00  0.00           H  
HETATM   51  H23 UNL     1      -5.244  -1.045  -1.003  1.00  0.00           H  
HETATM   52  H24 UNL     1      -5.661   1.662  -1.159  1.00  0.00           H  
HETATM   53  H25 UNL     1      -7.272   1.141   0.572  1.00  0.00           H  
HETATM   54  H26 UNL     1      -5.323   1.178   1.850  1.00  0.00           H  
HETATM   55  H27 UNL     1      -5.447   2.681   0.879  1.00  0.00           H  
HETATM   56  H28 UNL     1      -3.213   2.402   1.708  1.00  0.00           H  
HETATM   57  H29 UNL     1      -3.274   2.399  -0.084  1.00  0.00           H  
HETATM   58  H30 UNL     1      -2.129  -0.912   2.400  1.00  0.00           H  
HETATM   59  H31 UNL     1      -3.299   0.294   2.964  1.00  0.00           H  
HETATM   60  H32 UNL     1      -1.613   0.777   2.705  1.00  0.00           H  
HETATM   61  H33 UNL     1      -2.078   0.690  -1.080  1.00  0.00           H  
HETATM   62  H34 UNL     1      -0.589   1.828   1.293  1.00  0.00           H  
HETATM   63  H35 UNL     1      -1.251   2.631  -0.146  1.00  0.00           H  
HETATM   64  H36 UNL     1       1.209   2.440  -0.027  1.00  0.00           H  
HETATM   65  H37 UNL     1       0.525   1.856  -1.577  1.00  0.00           H  
HETATM   66  H38 UNL     1       1.624   1.162   1.620  1.00  0.00           H  
HETATM   67  H39 UNL     1       2.053  -0.649   1.529  1.00  0.00           H  
HETATM   68  H40 UNL     1       0.353  -0.023   1.587  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    8   32
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6    6    7
CONECT    7   37
CONECT    8    9   27   38
CONECT    9   10   39   40
CONECT   10   11   41   42
CONECT   11   12   27   43
CONECT   12   13   24   44
CONECT   13   14   15   45
CONECT   14   46
CONECT   15   16   47   48
CONECT   16   17   22   49
CONECT   17   18   50   51
CONECT   18   19   20   52
CONECT   19   53
CONECT   20   21   54   55
CONECT   21   22   56   57
CONECT   22   23   24
CONECT   23   58   59   60
CONECT   24   25   61
CONECT   25   26   62   63
CONECT   26   27   64   65
CONECT   27   28
CONECT   28   66   67   68
END

HMDB0000686
     RDKit          3D
Isoursodeoxycholic acid
 68 71  0  0  0  0  0  0  0  0999 V2000
    4.0712    0.9472    0.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7340   -0.2011   -0.3323 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9223   -0.6107   -1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0518   -1.1283   -0.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6843   -0.2719    0.6951 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3519   -0.3638    1.9024 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6715    0.6788    0.3926 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4909    0.1107   -1.1245 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1377   -1.0006   -2.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1324   -1.7996   -1.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2505   -0.6260   -0.9441 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9361   -0.7932   -0.1173 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9727   -1.6967   -0.8591 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4219   -2.9495   -1.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1009   -1.8901    0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7872   -0.5854    0.4553 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6308   -0.1764   -0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5739    0.9424   -0.3181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8221    0.4286    0.0221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0262    1.6488    0.9047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5187    1.8181    0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8017    0.4832    0.8795 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4029    0.1469    2.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6240    0.5463   -0.0477 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7355    1.7029    0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5917    1.6653   -0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2496    0.3148   -0.2893 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4014    0.1424    1.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0787    1.3970    0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4036    1.8405    0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9585    0.7722    1.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5247   -1.1384    0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6536   -1.5038   -1.7815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2856    0.2179   -1.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7644   -2.1333    0.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9157   -1.4585   -0.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4694    1.2977   -0.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6700    1.0457   -1.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9122   -1.5770   -2.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4817   -0.5190   -2.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5977   -2.2003   -0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6854   -2.5163   -1.9151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0671   -0.1801   -1.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8332   -1.3175    0.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2998   -1.1922   -1.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9586   -3.2447   -0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6678   -2.3757    1.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8556   -2.5615   -0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4575   -0.7630    1.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0202    0.1148   -1.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2437   -1.0454   -1.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6609    1.6622   -1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2716    1.1413    0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3232    1.1778    1.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4474    2.6811    0.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130    2.4024    1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2742    2.3995   -0.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1289   -0.9125    2.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2986    0.2940    2.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6127    0.7767    2.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0778    0.6899   -1.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5894    1.8282    1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2509    2.6307   -0.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2091    2.4404   -0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253    1.8558   -1.5767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6237    1.1622    1.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0527   -0.6488    1.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3534   -0.0229    1.5869 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
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27  8  1  0
 27 11  1  0
 24 12  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  6
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  6
 12 44  1  1
 13 45  1  6
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  1
 17 50  1  0
 17 51  1  0
 18 52  1  6
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 23 58  1  0
 23 59  1  0
 23 60  1  0
 24 61  1  6
 25 62  1  0
 25 63  1  0
 26 64  1  0
 26 65  1  0
 28 66  1  0
 28 67  1  0
 28 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3beta,5beta,7beta)-3,7-Dihydroxycholan-24-Oic acid	ChEBI
3beta,7beta-Dihydroxy-5beta-cholan-24-Oic acid	ChEBI
3beta,7beta-Dihydroxy-5beta-cholanoic acid	ChEBI
ISO-ursodeoxycholIC ACID	ChEBI
(3b,5b,7b)-3,7-Dihydroxycholan-24-Oate	Generator
(3b,5b,7b)-3,7-Dihydroxycholan-24-Oic acid	Generator
(3beta,5beta,7beta)-3,7-Dihydroxycholan-24-Oate	Generator
(3Β,5β,7β)-3,7-dihydroxycholan-24-Oate	Generator
(3Β,5β,7β)-3,7-dihydroxycholan-24-Oic acid	Generator
3b,7b-Dihydroxy-5b-cholan-24-Oate	Generator
3b,7b-Dihydroxy-5b-cholan-24-Oic acid	Generator
3beta,7beta-Dihydroxy-5beta-cholan-24-Oate	Generator
3Β,7β-dihydroxy-5β-cholan-24-Oate	Generator
3Β,7β-dihydroxy-5β-cholan-24-Oic acid	Generator
3b,7b-Dihydroxy-5b-cholanoate	Generator
3b,7b-Dihydroxy-5b-cholanoic acid	Generator
3beta,7beta-Dihydroxy-5beta-cholanoate	Generator
3Β,7β-dihydroxy-5β-cholanoate	Generator
3Β,7β-dihydroxy-5β-cholanoic acid	Generator
ISO-ursodeoxycholate	Generator
Isoursodeoxycholate	Generator
3b,7b-Dihydroxy-5b-cholanate	HMDB
3b,7b-Dihydroxy-5b-cholanic acid	HMDB
3b-Ursodeoxycholate	HMDB
3b-Ursodeoxycholic acid	HMDB
3,7-Dihydroxycholan-24-Oic acid	MeSH, HMDB
Sodium OF isoursodeoxycholic acid	MeSH, HMDB
3beta,7beta-Dihydroxy-5beta-cholanic acid	HMDB
3beta-Ursodeoxycholic acid	HMDB
3β,7β-Dihydroxy-5β-cholanic acid	HMDB
3β-Ursodeoxycholic acid	HMDB
Isoursodeoxycholic acid	HMDB

Chemical Formula

C₂₄H₄₀O₄

Average Molecular Weight

392.572

Monoisotopic Molecular Weight

392.292659768

IUPAC Name

(4R)-4-[(1S,2S,5S,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2S,5S,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

CAS Registry Number

78919-26-3

SMILES

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

InChI Identifier

InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16+,17-,18+,19+,20+,22+,23+,24-/m1/s1

InChI Key

RUDATBOHQWOJDD-DNMBCGTGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Dihydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
7-hydroxysteroid
7-alpha-hydroxysteroid
3-beta-hydroxysteroid
Hydroxysteroid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

dihydroxy-5beta-cholanic acid (CHEBI:43419 )
C24 bile acids, alcohols, and derivatives (C17662 )
C24 bile acids, alcohols, and derivatives (LMST04010035 )

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Depression (PMID: 35445772)

Alzheimer's Disease (PMID: 30337151)

Cirrhosis (PMID: 1112456)
Jaundice (PMID: 1112456)
Chronic hepatitis (PMID: 1112456)
Primary biliary cirrhosis (HMDB: HMDB0000686)

Cancer

Colorectal cancer (PMID: 21724466)

Digestive system disorder

Gastrointestinal disorder

Chronic diarrhea (PMID: 19900947)

Disposition

Biological location

Cytoplasm (HMDB: HMDB0000686)
Cell membrane (HMDB: HMDB0000686)

Biofluid or Excreta

Blood (HMDB: HMDB0000686)
Urine (HMDB: HMDB0000686)

Tissue substructure

Hepatic tissue (HMDB: HMDB0000686)

Organ

Excreta

Biofluid or Excreta

Urine (PMID: 2621422)
Feces (PMID: 29808030)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 2621422)
Bile (PMID: 31643938)

Cellular substructure

Extracellular (HMDB: HMDB0000686)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000686)

Source

Endogenous

Endogenous (HMDB: HMDB0000686)

Animal

Animal (HMDB: HMDB0000686)

Exogenous

Food

Food (HMDB: HMDB0000686)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0000686)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0000686)

Cellular process

Cell signaling (HMDB: HMDB0000686)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0000686)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	3.01	ALOGPS
logP	3.71	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.6	ChemAxon
pKa (Strongest Basic)	-0.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.27 m³·mol⁻¹	ChemAxon
Polarizability	46.72 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	191.545	31661259
DarkChem	[M-H]-	186.721	31661259
AllCCS	[M+H]+	201.415	32859911
AllCCS	[M-H]-	198.892	32859911
DeepCCS	[M-2H]-	234.524	30932474
DeepCCS	[M+Na]+	208.469	30932474
AllCCS	[M+H]+	201.4	32859911
AllCCS	[M+H-H2O]+	199.2	32859911
AllCCS	[M+NH4]+	203.4	32859911
AllCCS	[M+Na]+	204.0	32859911
AllCCS	[M-H]-	198.9	32859911
AllCCS	[M+Na-2H]-	200.2	32859911
AllCCS	[M+HCOO]-	201.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoursodeoxycholic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O	3820.1	Standard polar	33892256
Isoursodeoxycholic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O	3330.9	Standard non polar	33892256
Isoursodeoxycholic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O	3473.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isoursodeoxycholic acid,1TMS,isomer #1	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3313.4	Semi standard non polar	33892256
Isoursodeoxycholic acid,1TMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3372.3	Semi standard non polar	33892256
Isoursodeoxycholic acid,1TMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3313.4	Semi standard non polar	33892256
Isoursodeoxycholic acid,2TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3232.6	Semi standard non polar	33892256
Isoursodeoxycholic acid,2TMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3259.4	Semi standard non polar	33892256
Isoursodeoxycholic acid,2TMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3321.5	Semi standard non polar	33892256
Isoursodeoxycholic acid,3TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3235.5	Semi standard non polar	33892256
Isoursodeoxycholic acid,1TBDMS,isomer #1	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3530.1	Semi standard non polar	33892256
Isoursodeoxycholic acid,1TBDMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3592.0	Semi standard non polar	33892256
Isoursodeoxycholic acid,1TBDMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3577.3	Semi standard non polar	33892256
Isoursodeoxycholic acid,2TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3702.6	Semi standard non polar	33892256
Isoursodeoxycholic acid,2TBDMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3698.7	Semi standard non polar	33892256
Isoursodeoxycholic acid,2TBDMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3813.9	Semi standard non polar	33892256
Isoursodeoxycholic acid,3TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3915.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isoursodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-01rt-0529000000-3b28c649fc51c7806ad3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoursodeoxycholic acid GC-MS (3 TMS) - 70eV, Positive	splash10-0006-1110390000-52bc66ab11fd14425d4f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoursodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoursodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoursodeoxycholic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoursodeoxycholic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoursodeoxycholic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoursodeoxycholic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoursodeoxycholic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoursodeoxycholic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoursodeoxycholic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoursodeoxycholic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoursodeoxycholic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoursodeoxycholic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoursodeoxycholic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoursodeoxycholic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoursodeoxycholic acid GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoursodeoxycholic acid 10V, Positive-QTOF	splash10-056r-0009000000-997e61e986e67265241c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoursodeoxycholic acid 20V, Positive-QTOF	splash10-056r-0009000000-81134947694f847d1c65	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoursodeoxycholic acid 40V, Positive-QTOF	splash10-02t9-1219000000-6a0ddebebacac090c27e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoursodeoxycholic acid 10V, Negative-QTOF	splash10-0006-0009000000-efdaad69eee0ae934dd5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoursodeoxycholic acid 20V, Negative-QTOF	splash10-006x-1009000000-15b4edab9d05e4c3693a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoursodeoxycholic acid 40V, Negative-QTOF	splash10-0a4l-9006000000-9291e69db3a3c47ecd97	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoursodeoxycholic acid 10V, Negative-QTOF	splash10-0006-0009000000-7631731446db77938069	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoursodeoxycholic acid 20V, Negative-QTOF	splash10-006x-0009000000-39e7e555dc6b36ada2af	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoursodeoxycholic acid 40V, Negative-QTOF	splash10-000i-1009000000-351c21e3dab693818b22	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoursodeoxycholic acid 10V, Positive-QTOF	splash10-0006-0019000000-56dc67f71a8507c1433f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoursodeoxycholic acid 20V, Positive-QTOF	splash10-0a4i-3039000000-510702cae19e3906b6e1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoursodeoxycholic acid 40V, Positive-QTOF	splash10-0002-9550000000-7486a5f56afd302efa7e	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Gall Bladder
Intestine
Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.3 (0.3-5.0) uM	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details
Urine	Detected and Quantified	1.1 (0.09-4.5) umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details

Associated Disorders and Diseases

Disease References

Primary biliary cirrhosis
Batta AK, Arora R, Salen G, Tint GS, Eskreis D, Katz S: Characterization of serum and urinary bile acids in patients with primary biliary cirrhosis by gas-liquid chromatography-mass spectrometry: effect of ursodeoxycholic acid treatment. J Lipid Res. 1989 Dec;30(12):1953-62. [PubMed:2621422 ]

Associated OMIM IDs

109720 (Primary biliary cirrhosis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022182

KNApSAcK ID

Not Available

Chemspider ID

113205

KEGG Compound ID

C17662

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

127601

PDB ID

Not Available

ChEBI ID

43419

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Thomas, Hans Guenter. Procedure for the preparation of isoursodeoxychloic acid. Ger. Offen. (1996), 8 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [PubMed:11316487 ]
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. Epub 2005 Jul 21. [PubMed:16037564 ]
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. [PubMed:12576301 ]
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 ]

Enzymes

Enzyme Details

1. Gastrotropin

General function:: Involved in binding
Specific function:: Ileal protein which stimulates gastric acid and pepsinogen secretion. Seems to be able to bind to bile salts and bilirubins. Isoform 2 is essential for the survival of colon cancer cells to bile acid-induced apoptosis
Gene Name:: FABP6
Uniprot ID:: P51161
Molecular weight:: 14371.2

References

Kurz M, Brachvogel V, Matter H, Stengelin S, Thuring H, Kramer W: Insights into the bile acid transportation system: the human ileal lipid-binding protein-cholyltaurine complex and its comparison with homologous structures. Proteins. 2003 Feb 1;50(2):312-28. [PubMed:12486725 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1B3

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
Gene Name:: SLCO1B3
Uniprot ID:: Q9NPD5
Molecular weight:: 77402.2

Enzyme Details

2. Solute carrier organic anion transporter family member 1B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:: SLCO1B1
Uniprot ID:: Q9Y6L6
Molecular weight:: 76448.0

References

Michalski C, Cui Y, Nies AT, Nuessler AK, Neuhaus P, Zanger UM, Klein K, Eichelbaum M, Keppler D, Konig J: A naturally occurring mutation in the SLC21A6 gene causing impaired membrane localization of the hepatocyte uptake transporter. J Biol Chem. 2002 Nov 8;277(45):43058-63. Epub 2002 Aug 23. [PubMed:12196548 ]

Enzyme Details

3. Canalicular multispecific organic anion transporter 2

General function:: Involved in ATP binding
Specific function:: May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:: ABCC3
Uniprot ID:: O15438
Molecular weight:: 169341.1

Enzyme Details

4. Bile salt export pump

General function:: Involved in ATP binding
Specific function:: Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:: ABCB11
Uniprot ID:: O95342
Molecular weight:: 146405.8

Enzyme Details

5. Ileal sodium/bile acid cotransporter

General function:: Involved in bile acid:sodium symporter activity
Specific function:: Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism
Gene Name:: SLC10A2
Uniprot ID:: Q12908
Molecular weight:: 37697.4

References

Kramer W, Girbig F, Glombik H, Corsiero D, Stengelin S, Weyland C: Identification of a ligand-binding site in the Na+/bile acid cotransporting protein from rabbit ileum. J Biol Chem. 2001 Sep 21;276(38):36020-7. Epub 2001 Jul 10. [PubMed:11447228 ]

Enzyme Details

6. Sodium/bile acid cotransporter

General function:: Involved in bile acid:sodium symporter activity
Specific function:: The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium.
Gene Name:: SLC10A1
Uniprot ID:: Q14973
Molecular weight:: 38118.64

Enzyme Details

7. Solute carrier organic anion transporter family member 1A2

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:: SLCO1A2
Uniprot ID:: P46721
Molecular weight:: 74144.1

Enzyme Details

8. Solute carrier organic anion transporter family member 4A1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate
Gene Name:: SLCO4A1
Uniprot ID:: Q96BD0
Molecular weight:: 77192.5

Showing metabocard for Isoursodeoxycholic acid (HMDB0000686)

MOL for HMDB0000686 (Isoursodeoxycholic acid)

3D MOL for HMDB0000686 (Isoursodeoxycholic acid)

3D SDF for HMDB0000686 (Isoursodeoxycholic acid)

3D-SDF for HMDB0000686 (Isoursodeoxycholic acid)

PDB for HMDB0000686 (Isoursodeoxycholic acid)

3D PDB for HMDB0000686 (Isoursodeoxycholic acid)

SMILES for HMDB0000686 (Isoursodeoxycholic acid)

INCHI for HMDB0000686 (Isoursodeoxycholic acid)

Structure for HMDB0000686 (Isoursodeoxycholic acid)

3D Structure for HMDB0000686 (Isoursodeoxycholic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Transporters

References

References