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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3)transporters (8) Show 11 proteins XML

enzymes (3)transporters (8) Show 11 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:07 UTC

HMDB ID

HMDB0000946

Secondary Accession Numbers

HMDB0015525
HMDB00946
HMDB15525

Metabolite Identification

Common Name

Ursodeoxycholic acid

Description

Ursodeoxycholic acid, also known as ursodeoxycholate or acid deoxyursocholic, 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. Ursodeoxycholic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.

Structure

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

1586
  Mrv1652305271900322D          

 33 36  0  0  1  0            999 V2000
    6.5590   -2.5194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0919   -2.5366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7049    2.9254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9996    1.5273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5410   -0.8436    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5410   -0.0186    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8265   -1.2561    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1122   -0.8436    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3614   -1.2617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3215    0.2327    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3547   -2.1210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8265    0.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1122   -0.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8398   -2.1153    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3215   -1.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8030   -0.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0990   -2.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5968   -0.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5410    0.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5779    1.0169    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5831   -2.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3678   -0.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8148   -1.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8079   -2.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3851    1.1870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0270    1.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6415    1.9712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4487    2.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6109   -1.4999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4007   -1.5816    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6836   -0.5137    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9736    0.3352    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3573   -2.7809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 14  1  1  1  0  0  0
 24  2  1  6  0  0  0
  3 28  1  0  0  0  0
  4 28  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 15  1  0  0  0  0
  5 29  1  6  0  0  0
  6 10  1  0  0  0  0
  6 12  1  0  0  0  0
  6 19  1  1  0  0  0
  7  8  1  0  0  0  0
  7 14  1  0  0  0  0
  7 30  1  1  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  8 31  1  6  0  0  0
  9 11  1  0  0  0  0
  9 18  1  0  0  0  0
  9 22  1  1  0  0  0
 10 16  1  0  0  0  0
 10 20  1  0  0  0  0
 10 32  1  6  0  0  0
 11 17  1  0  0  0  0
 11 21  1  0  0  0  0
 11 33  1  1  0  0  0
 12 13  1  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 18 23  1  0  0  0  0
 20 25  1  0  0  0  0
 20 26  1  6  0  0  0
 21 24  1  0  0  0  0
 23 24  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

HMDB0000946
     RDKit          3D
Ursodeoxycholic acid
 68 71  0  0  0  0  0  0  0  0999 V2000
    4.2279    0.5757    1.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9123   -0.3678    0.6095 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0966   -0.2610   -0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2772    1.1420   -0.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4536    1.1198   -1.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1145    0.0769   -2.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8407    2.3031   -2.4070 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6369   -0.2316   -0.0882 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5342   -1.2895   -1.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1592   -1.9068   -0.9818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4297   -0.7210   -0.4826 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9934   -0.8905   -0.1011 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7146   -1.2163   -1.4213 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4595   -2.5876   -1.6501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831   -1.0243   -1.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6639   -0.7793    0.1202 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1523   -0.4925    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4570    0.7898   -0.6841 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6866    0.5514   -2.0447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4147    1.8446   -0.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6576    1.6117    0.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9080    0.2949    0.8522 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8736   -0.1376    2.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5107    0.4240    0.3642 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6238    1.1334    1.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8243    1.1582    0.9335 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3519   -0.2319    0.6200 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1570   -1.0804    1.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1593    1.6485    1.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3103    0.4325    1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7148    0.3474    2.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198   -1.3873    1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0710   -1.0030   -1.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0014   -0.5215    0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3981    1.3749   -1.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4815    1.8749   -0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1410    3.0595   -1.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6637    0.7441   -0.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3371   -2.0488   -1.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5637   -0.8761   -2.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846   -2.7219   -0.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8300   -2.2893   -1.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4694    0.0622   -1.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2237   -1.7470    0.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2584   -0.5951   -2.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0549   -3.1430   -1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7287   -1.9471   -1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4911   -0.2400   -1.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5842   -1.7634    0.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5554   -0.4401    1.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6152   -1.3466   -0.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4579    1.1309   -0.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4125   -0.0977   -2.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7469    2.0359   -1.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9664    2.8175   -0.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4196    1.5835    1.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9438    2.4369    0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6598    0.7173    2.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9262   -0.4443    2.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2569   -1.0176    2.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5519    1.0879   -0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7307    0.7596    2.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9574    2.1928    1.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3922    1.6395    1.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9001    1.7844    0.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4913   -2.1320    1.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0632   -1.1443    1.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5318   -0.6319    2.7667 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  1
 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

1586
  Mrv1652305271900322D          

 33 36  0  0  1  0            999 V2000
    6.5590   -2.5194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0919   -2.5366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7049    2.9254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9996    1.5273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5410   -0.8436    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5410   -0.0186    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8265   -1.2561    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1122   -0.8436    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3614   -1.2617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3215    0.2327    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3547   -2.1210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8265    0.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1122   -0.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8398   -2.1153    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3215   -1.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8030   -0.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0990   -2.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5968   -0.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5410    0.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5779    1.0169    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5831   -2.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3678   -0.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8148   -1.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8079   -2.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3851    1.1870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0270    1.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6415    1.9712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4487    2.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6109   -1.4999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4007   -1.5816    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6836   -0.5137    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9736    0.3352    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3573   -2.7809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 14  1  1  1  0  0  0
 24  2  1  6  0  0  0
  3 28  1  0  0  0  0
  4 28  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 15  1  0  0  0  0
  5 29  1  6  0  0  0
  6 10  1  0  0  0  0
  6 12  1  0  0  0  0
  6 19  1  1  0  0  0
  7  8  1  0  0  0  0
  7 14  1  0  0  0  0
  7 30  1  1  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  8 31  1  6  0  0  0
  9 11  1  0  0  0  0
  9 18  1  0  0  0  0
  9 22  1  1  0  0  0
 10 16  1  0  0  0  0
 10 20  1  0  0  0  0
 10 32  1  6  0  0  0
 11 17  1  0  0  0  0
 11 21  1  0  0  0  0
 11 33  1  1  0  0  0
 12 13  1  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 18 23  1  0  0  0  0
 20 25  1  0  0  0  0
 20 26  1  6  0  0  0
 21 24  1  0  0  0  0
 23 24  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000946

> <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-UZVSRGJWSA-N

> <FORMULA>
C24H40O4

> <MOLECULAR_WEIGHT>
392.572

> <EXACT_MASS>
392.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
46.424384430421426

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2S,5R,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>
77.75999999999999

> <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,5R,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

$$$$

HMDB0000946
     RDKit          3D
Ursodeoxycholic acid
 68 71  0  0  0  0  0  0  0  0999 V2000
    4.2279    0.5757    1.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9123   -0.3678    0.6095 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0966   -0.2610   -0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2772    1.1420   -0.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4536    1.1198   -1.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1145    0.0769   -2.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8407    2.3031   -2.4070 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6369   -0.2316   -0.0882 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5342   -1.2895   -1.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1592   -1.9068   -0.9818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4297   -0.7210   -0.4826 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9934   -0.8905   -0.1011 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7146   -1.2163   -1.4213 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4595   -2.5876   -1.6501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831   -1.0243   -1.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6639   -0.7793    0.1202 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1523   -0.4925    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4570    0.7898   -0.6841 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6866    0.5514   -2.0447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4147    1.8446   -0.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6576    1.6117    0.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9080    0.2949    0.8522 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8736   -0.1376    2.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5107    0.4240    0.3642 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6238    1.1334    1.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8243    1.1582    0.9335 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3519   -0.2319    0.6200 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1570   -1.0804    1.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1593    1.6485    1.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3103    0.4325    1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7148    0.3474    2.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198   -1.3873    1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0710   -1.0030   -1.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0014   -0.5215    0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3981    1.3749   -1.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4815    1.8749   -0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1410    3.0595   -1.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6637    0.7441   -0.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3371   -2.0488   -1.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5637   -0.8761   -2.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846   -2.7219   -0.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8300   -2.2893   -1.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4694    0.0622   -1.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2237   -1.7470    0.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2584   -0.5951   -2.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0549   -3.1430   -1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7287   -1.9471   -1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4911   -0.2400   -1.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5842   -1.7634    0.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5554   -0.4401    1.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6152   -1.3466   -0.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4579    1.1309   -0.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4125   -0.0977   -2.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7469    2.0359   -1.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9664    2.8175   -0.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4196    1.5835    1.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9438    2.4369    0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6598    0.7173    2.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9262   -0.4443    2.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2569   -1.0176    2.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5519    1.0879   -0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7307    0.7596    2.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9574    2.1928    1.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3922    1.6395    1.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9001    1.7844    0.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4913   -2.1320    1.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0632   -1.1443    1.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5318   -0.6319    2.7667 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  1
 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                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1586                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      12.243  -4.703   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.905  -4.735   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      18.116   5.461   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      18.666   2.851   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      12.210  -1.575   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.210  -0.035   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.876  -2.345   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.543  -1.575   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.141  -2.355   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.667   0.434   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.129  -3.959   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.876   0.735   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.543  -0.035   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.901  -3.949   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.667  -2.044   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.566  -0.805   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.518  -4.761   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.714  -1.486   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.210   1.505   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.145   1.898   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.688  -4.806   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.153  -0.815   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.254  -2.300   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.241  -3.970   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.652   2.216   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.117   3.045   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.131   3.680   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.638   3.997   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      12.340  -2.800   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      11.948  -2.952   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      10.609  -0.959   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      14.884   0.626   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       8.134  -5.191   0.000  0.00  0.00           H+0
CONECT    1   14                                                            
CONECT    2   24                                                            
CONECT    3   28                                                            
CONECT    4   28                                                            
CONECT    5    6    7   15   29                                             
CONECT    6    5   10   12   19                                             
CONECT    7    5    8   14   30                                             
CONECT    8    7    9   13   31                                             
CONECT    9    8   11   18   22                                             
CONECT   10    6   16   20   32                                             
CONECT   11    9   17   21   33                                             
CONECT   12    6   13                                                       
CONECT   13    8   12                                                       
CONECT   14    1    7   17                                                  
CONECT   15    5   16                                                       
CONECT   16   10   15                                                       
CONECT   17   11   14                                                       
CONECT   18    9   23                                                       
CONECT   19    6                                                            
CONECT   20   10   25   26                                                  
CONECT   21   11   24                                                       
CONECT   22    9                                                            
CONECT   23   18   24                                                       
CONECT   24    2   21   23                                                  
CONECT   25   20   27                                                       
CONECT   26   20                                                            
CONECT   27   25   28                                                       
CONECT   28    3    4   27                                                  
CONECT   29    5                                                            
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32   10                                                            
CONECT   33   11                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0000946
HETATM    1  C1  UNL     1       4.228   0.576   1.727  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.912  -0.368   0.609  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.097  -0.261  -0.341  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.277   1.142  -0.869  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.454   1.120  -1.779  1.00  0.00           C  
HETATM    6  O1  UNL     1       7.115   0.077  -2.006  1.00  0.00           O  
HETATM    7  O2  UNL     1       6.841   2.303  -2.407  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.637  -0.232  -0.088  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.534  -1.289  -1.173  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.159  -1.907  -0.982  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.430  -0.721  -0.483  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.993  -0.890  -0.101  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.715  -1.216  -1.421  1.00  0.00           C  
HETATM   14  O3  UNL     1      -1.460  -2.588  -1.650  1.00  0.00           O  
HETATM   15  C12 UNL     1      -3.183  -1.024  -1.268  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.664  -0.779   0.120  1.00  0.00           C  
HETATM   17  C14 UNL     1      -5.152  -0.492   0.054  1.00  0.00           C  
HETATM   18  C15 UNL     1      -5.457   0.790  -0.684  1.00  0.00           C  
HETATM   19  O4  UNL     1      -5.687   0.551  -2.045  1.00  0.00           O  
HETATM   20  C16 UNL     1      -4.415   1.845  -0.446  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.658   1.612   0.840  1.00  0.00           C  
HETATM   22  C18 UNL     1      -2.908   0.295   0.852  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.874  -0.138   2.312  1.00  0.00           C  
HETATM   24  C20 UNL     1      -1.511   0.424   0.364  1.00  0.00           C  
HETATM   25  C21 UNL     1      -0.624   1.133   1.346  1.00  0.00           C  
HETATM   26  C22 UNL     1       0.824   1.158   0.934  1.00  0.00           C  
HETATM   27  C23 UNL     1       1.352  -0.232   0.620  1.00  0.00           C  
HETATM   28  C24 UNL     1       1.157  -1.080   1.800  1.00  0.00           C  
HETATM   29  H1  UNL     1       4.159   1.649   1.443  1.00  0.00           H  
HETATM   30  H2  UNL     1       5.310   0.433   1.958  1.00  0.00           H  
HETATM   31  H3  UNL     1       3.715   0.347   2.679  1.00  0.00           H  
HETATM   32  H4  UNL     1       4.020  -1.387   1.045  1.00  0.00           H  
HETATM   33  H5  UNL     1       5.071  -1.003  -1.158  1.00  0.00           H  
HETATM   34  H6  UNL     1       6.001  -0.522   0.280  1.00  0.00           H  
HETATM   35  H7  UNL     1       4.398   1.375  -1.502  1.00  0.00           H  
HETATM   36  H8  UNL     1       5.482   1.875  -0.092  1.00  0.00           H  
HETATM   37  H9  UNL     1       7.141   3.060  -1.813  1.00  0.00           H  
HETATM   38  H10 UNL     1       2.664   0.744  -0.634  1.00  0.00           H  
HETATM   39  H11 UNL     1       3.337  -2.049  -1.081  1.00  0.00           H  
HETATM   40  H12 UNL     1       2.564  -0.876  -2.189  1.00  0.00           H  
HETATM   41  H13 UNL     1       1.285  -2.722  -0.246  1.00  0.00           H  
HETATM   42  H14 UNL     1       0.830  -2.289  -1.970  1.00  0.00           H  
HETATM   43  H15 UNL     1       0.469   0.062  -1.273  1.00  0.00           H  
HETATM   44  H16 UNL     1      -1.224  -1.747   0.546  1.00  0.00           H  
HETATM   45  H17 UNL     1      -1.258  -0.595  -2.201  1.00  0.00           H  
HETATM   46  H18 UNL     1      -2.055  -3.143  -1.115  1.00  0.00           H  
HETATM   47  H19 UNL     1      -3.729  -1.947  -1.628  1.00  0.00           H  
HETATM   48  H20 UNL     1      -3.491  -0.240  -1.991  1.00  0.00           H  
HETATM   49  H21 UNL     1      -3.584  -1.763   0.669  1.00  0.00           H  
HETATM   50  H22 UNL     1      -5.555  -0.440   1.086  1.00  0.00           H  
HETATM   51  H23 UNL     1      -5.615  -1.347  -0.489  1.00  0.00           H  
HETATM   52  H24 UNL     1      -6.458   1.131  -0.285  1.00  0.00           H  
HETATM   53  H25 UNL     1      -6.413  -0.098  -2.114  1.00  0.00           H  
HETATM   54  H26 UNL     1      -3.747   2.036  -1.296  1.00  0.00           H  
HETATM   55  H27 UNL     1      -4.966   2.817  -0.284  1.00  0.00           H  
HETATM   56  H28 UNL     1      -4.420   1.584   1.646  1.00  0.00           H  
HETATM   57  H29 UNL     1      -2.944   2.437   0.979  1.00  0.00           H  
HETATM   58  H30 UNL     1      -2.660   0.717   2.996  1.00  0.00           H  
HETATM   59  H31 UNL     1      -3.926  -0.444   2.595  1.00  0.00           H  
HETATM   60  H32 UNL     1      -2.257  -1.018   2.499  1.00  0.00           H  
HETATM   61  H33 UNL     1      -1.552   1.088  -0.552  1.00  0.00           H  
HETATM   62  H34 UNL     1      -0.731   0.760   2.386  1.00  0.00           H  
HETATM   63  H35 UNL     1      -0.957   2.193   1.374  1.00  0.00           H  
HETATM   64  H36 UNL     1       1.392   1.639   1.749  1.00  0.00           H  
HETATM   65  H37 UNL     1       0.900   1.784   0.016  1.00  0.00           H  
HETATM   66  H38 UNL     1       1.491  -2.132   1.693  1.00  0.00           H  
HETATM   67  H39 UNL     1       0.063  -1.144   1.995  1.00  0.00           H  
HETATM   68  H40 UNL     1       1.532  -0.632   2.767  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

HMDB0000946
     RDKit          3D
Ursodeoxycholic acid
 68 71  0  0  0  0  0  0  0  0999 V2000
    4.2279    0.5757    1.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9123   -0.3678    0.6095 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0966   -0.2610   -0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2772    1.1420   -0.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4536    1.1198   -1.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1145    0.0769   -2.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8407    2.3031   -2.4070 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6369   -0.2316   -0.0882 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5342   -1.2895   -1.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1592   -1.9068   -0.9818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4297   -0.7210   -0.4826 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9934   -0.8905   -0.1011 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7146   -1.2163   -1.4213 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4595   -2.5876   -1.6501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831   -1.0243   -1.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6639   -0.7793    0.1202 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1523   -0.4925    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4570    0.7898   -0.6841 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6866    0.5514   -2.0447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4147    1.8446   -0.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6576    1.6117    0.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9080    0.2949    0.8522 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8736   -0.1376    2.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5107    0.4240    0.3642 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6238    1.1334    1.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8243    1.1582    0.9335 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3519   -0.2319    0.6200 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1570   -1.0804    1.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1593    1.6485    1.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3103    0.4325    1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7148    0.3474    2.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198   -1.3873    1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0710   -1.0030   -1.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0014   -0.5215    0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3981    1.3749   -1.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4815    1.8749   -0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1410    3.0595   -1.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6637    0.7441   -0.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3371   -2.0488   -1.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5637   -0.8761   -2.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846   -2.7219   -0.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8300   -2.2893   -1.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4694    0.0622   -1.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2237   -1.7470    0.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2584   -0.5951   -2.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0549   -3.1430   -1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7287   -1.9471   -1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4911   -0.2400   -1.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5842   -1.7634    0.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5554   -0.4401    1.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6152   -1.3466   -0.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4579    1.1309   -0.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4125   -0.0977   -2.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7469    2.0359   -1.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9664    2.8175   -0.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4196    1.5835    1.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9438    2.4369    0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6598    0.7173    2.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9262   -0.4443    2.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2569   -1.0176    2.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5519    1.0879   -0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7307    0.7596    2.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9574    2.1928    1.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3922    1.6395    1.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9001    1.7844    0.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4913   -2.1320    1.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0632   -1.1443    1.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5318   -0.6319    2.7667 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  1
 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
(3alpha,5beta,7beta)-3,7-Dihydroxycholan-24-Oic acid	ChEBI
3alpha,7beta-Dihydroxy-5beta-cholan-24-Oic acid	ChEBI
Actigall	ChEBI
Ursodeoxycholate	ChEBI
Ursodiol	ChEBI
Urso	Kegg
(3a,5b,7b)-3,7-Dihydroxycholan-24-Oate	Generator
(3a,5b,7b)-3,7-Dihydroxycholan-24-Oic acid	Generator
(3alpha,5beta,7beta)-3,7-Dihydroxycholan-24-Oate	Generator
(3Α,5β,7β)-3,7-dihydroxycholan-24-Oate	Generator
(3Α,5β,7β)-3,7-dihydroxycholan-24-Oic acid	Generator
3a,7b-Dihydroxy-5b-cholan-24-Oate	Generator
3a,7b-Dihydroxy-5b-cholan-24-Oic acid	Generator
3alpha,7beta-Dihydroxy-5beta-cholan-24-Oate	Generator
3Α,7β-dihydroxy-5β-cholan-24-Oate	Generator
3Α,7β-dihydroxy-5β-cholan-24-Oic acid	Generator
3 alpha,7 beta-Dihydroxy-5 beta-cholan-24-Oic acid	HMDB
Acid, deoxyursocholic	HMDB
Acid, ursacholic	HMDB
Acid, ursodeoxycholic	HMDB
Cholit-ursan	HMDB
Cholofalk	HMDB
Delursan	HMDB
Deoxyursocholic acid	HMDB
Ursochol	HMDB
Ursogal	HMDB
Ursolite	HMDB
Ursolvan	HMDB
Urso heumann	HMDB
Ursobilane	HMDB
Ursofalk	HMDB
Destolit	HMDB
Sodium ursodeoxycholate	HMDB
Ursacholic acid	HMDB
Ursodeoxycholate, sodium	HMDB
3 alpha,7 beta Dihydroxy 5 beta cholan 24 Oic acid	HMDB
Urdox	HMDB
(3a,5b,7b)-3,7-Dihydroxy-cholan-24-Oate	HMDB
(3a,5b,7b)-3,7-Dihydroxy-cholan-24-Oic acid	HMDB
3,7-Dihydroxycholan-24-Oic acid	HMDB
3-alpha,7-beta-Dihydroxy-5-beta-cholanoic acid	HMDB
3-alpha,7-beta-Dihydroxycholanic acid	HMDB
3-alpha,7-beta-Dioxycholanic acid	HMDB
Antigall	HMDB
Urosdesoxycholate	HMDB
Urosdesoxycholic acid	HMDB
Ursodeoxycholicacid	HMDB
Ursodexycholate	HMDB
Ursodexycholic acid	HMDB
Aventis brand OF ursodeoxycholic acid	HMDB
Axcan brand OF ursodeoxycholic acid	HMDB
Falk brand OF ursodeoxycholic acid	HMDB
Farmasa brand OF ursodeoxycholic acid	HMDB
Galen brand OF ursodeoxycholic acid	HMDB
Orphan brand OF ursodeoxycholic acid	HMDB
Antigen brand OF ursodeoxycholic acid	HMDB
CP Brand OF ursodeoxycholic acid	HMDB
Heumann brand OF ursodeoxycholic acid	HMDB
Niddapharm brand OF ursodeoxycholic acid	HMDB
Norgine brand OF ursodeoxycholic acid	HMDB
Sanofi synthelabo brand OF ursodeoxycholic acid	HMDB
Estedi brand OF ursodeoxycholic acid	HMDB
Provalis brand OF ursodeoxycholic acid	HMDB
Tramedico brand OF ursodeoxycholic acid	HMDB
Vita brand OF ursodeoxycholic acid	HMDB
Zambon brand OF ursodeoxycholic acid	HMDB

Chemical Formula

C₂₄H₄₀O₄

Average Molecular Weight

392.572

Monoisotopic Molecular Weight

392.292659768

IUPAC Name

(4R)-4-[(1S,2S,5R,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,5R,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

128-13-2

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-UZVSRGJWSA-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-alpha-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

bile acid (CHEBI:9907 )
dihydroxy-5beta-cholanic acid (CHEBI:9907 )
C24 bile acids, alcohols, and derivatives (C07880 )
Cholane and derivatives (C07880 )
C24 bile acids, alcohols, and derivatives (LMST04010033 )

Ontology

Physiological effect

Organoleptic effect

Odor

bitter

Disposition

Biological location

Organ substructure

Adrenal Cortex (HMDB: HMDB0000946)

Organ

Cell

Fibroblasts (HMDB: HMDB0000946)

Tissue

Muscle tissue

Skeletal Muscle (HMDB: HMDB0000946)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 15185309)

Excreta

Biofluid or Excreta

Urine (PMID: 2621422)
Feces (PMID: 22664055)

Cellular substructure

Extracellular (HMDB: HMDB0000946)

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

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Cystic fibrosis (MarkerDB: MDB00000289)
Cirrhosis (MarkerDB: MDB00000289)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	203 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.02 mg/mL	Not Available
LogP	3.00	RODA,A ET AL. (1990)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	200.2	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002153

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	46.42 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]+	193.064	31661259
DarkChem	[M-H]-	191.37	31661259
AllCCS	[M+H]+	200.81	32859911
AllCCS	[M-H]-	198.892	32859911
DeepCCS	[M-2H]-	236.123	30932474
DeepCCS	[M+Na]+	210.098	30932474
AllCCS	[M+H]+	200.8	32859911
AllCCS	[M+H-H2O]+	198.7	32859911
AllCCS	[M+NH4]+	202.8	32859911
AllCCS	[M+Na]+	203.3	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
Ursodeoxycholic 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
Ursodeoxycholic 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
Ursodeoxycholic 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
Ursodeoxycholic 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
Ursodeoxycholic 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
Ursodeoxycholic 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
Ursodeoxycholic 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
Ursodeoxycholic 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
Ursodeoxycholic 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
Ursodeoxycholic 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
Ursodeoxycholic 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
Ursodeoxycholic 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
Ursodeoxycholic 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
Ursodeoxycholic 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
Ursodeoxycholic 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
Ursodeoxycholic 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
Ursodeoxycholic 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 - Ursodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-01rt-0419000000-6a92f910581240163a99	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursodeoxycholic 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 - Ursodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursodeoxycholic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursodeoxycholic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursodeoxycholic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursodeoxycholic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursodeoxycholic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursodeoxycholic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursodeoxycholic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursodeoxycholic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursodeoxycholic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursodeoxycholic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursodeoxycholic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursodeoxycholic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursodeoxycholic acid GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursodeoxycholic acid LC-ESI-qTof , Positive-QTOF	splash10-0a4l-3940000000-cf90a6f216d592e2ad4c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursodeoxycholic acid LC-ESI-IT , negative-QTOF	splash10-00di-0029000000-54929e08fef761ba2b28	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursodeoxycholic acid , positive-QTOF	splash10-0002-2911000000-eec2b269eeb08a30ac6e	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 10V, Positive-QTOF	splash10-056r-0009000000-997e61e986e67265241c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 20V, Positive-QTOF	splash10-056r-0009000000-81134947694f847d1c65	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 40V, Positive-QTOF	splash10-02t9-1219000000-6a0ddebebacac090c27e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 10V, Negative-QTOF	splash10-0006-0009000000-efdaad69eee0ae934dd5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 20V, Negative-QTOF	splash10-006x-1009000000-15b4edab9d05e4c3693a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 40V, Negative-QTOF	splash10-0a4l-9006000000-9291e69db3a3c47ecd97	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 10V, Negative-QTOF	splash10-0006-0009000000-7631731446db77938069	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 20V, Negative-QTOF	splash10-006x-0009000000-39e7e555dc6b36ada2af	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 40V, Negative-QTOF	splash10-000i-1009000000-351c21e3dab693818b22	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 10V, Positive-QTOF	splash10-0006-0019000000-56dc67f71a8507c1433f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 20V, Positive-QTOF	splash10-0a4i-3039000000-510702cae19e3906b6e1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 40V, Positive-QTOF	splash10-0002-9550000000-7486a5f56afd302efa7e	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2018-05-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Adrenal Cortex
Bladder
Fibroblasts
Intestine
Liver
Placenta
Skeletal Muscle

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.16 +/- 0.03 uM	Adult (>18 years old)	Both	Normal	15185309	details
Feces	Detected and Quantified	27.05 +/- 61.13 nmol/g dry feces	Not Specified	Not Specified	Normal	22664055	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23940645	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected and Quantified	0.022 (0.013-0.030) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.7 (0.7-3.0) uM	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details
Blood	Detected and Quantified	24.5 (2.3-51.3) uM	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details
Blood	Detected and Quantified	0.48 +/- 0.16 uM	Adult (>18 years old)	Both	Cystic fibrosis	15185309	details
Blood	Detected and Quantified	0.61 +/- 0.27 uM	Children (1-13 years old)	Both	Cystic fibrosis	15185309	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	23940645	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	23940645	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	0.29 (0.056-0.98) umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details
Urine	Detected and Quantified	12.5 (0.7-53.9) umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details

Associated Disorders and Diseases

Disease References

Cystic fibrosis
Smith JL, Lewindon PJ, Hoskins AC, Pereira TN, Setchell KD, O'Connell NC, Shepherd RW, Ramm GA: Endogenous ursodeoxycholic acid and cholic acid in liver disease due to cystic fibrosis. Hepatology. 2004 Jun;39(6):1673-82. [PubMed:15185309 ]
Colorectal cancer
Weir TL, Manter DK, Sheflin AM, Barnett BA, Heuberger AL, Ryan EP: Stool microbiome and metabolome differences between colorectal cancer patients and healthy adults. PLoS One. 2013 Aug 6;8(8):e70803. doi: 10.1371/journal.pone.0070803. Print 2013. [PubMed:23940645 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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

219700 (Cystic fibrosis)
114500 (Colorectal cancer)
109720 (Primary biliary cirrhosis)

External Links

DrugBank ID

DB01586

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ursodiol

METLIN ID

5893

PubChem Compound

31401

PDB ID

Not Available

ChEBI ID

9907

Food Biomarker Ontology

Not Available

VMH ID

HC02194

MarkerDB ID

MDB00000289

Good Scents ID

Not Available

References

Synthesis Reference

Sawada, Haruji; Kulprecha, Songsri; Nilubol, Naline; Yoshida, Toshiomi; Kinoshita, Shinichi; Taguchi, Hisaharu. Microbial production of ursodeoxycholic acid from lithocholic acid by Fusarium equiseti M41. Applied and Environmental Microbiology (1982), 44(6):1249-52

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Smith JL, Lewindon PJ, Hoskins AC, Pereira TN, Setchell KD, O'Connell NC, Shepherd RW, Ramm GA: Endogenous ursodeoxycholic acid and cholic acid in liver disease due to cystic fibrosis. Hepatology. 2004 Jun;39(6):1673-82. [PubMed:15185309 ]
Fiorucci S, Antonelli E, Morelli A: Nitric oxide and portal hypertension: a nitric oxide-releasing derivative of ursodeoxycholic acid that selectively releases nitric oxide in the liver. Dig Liver Dis. 2003 May;35 Suppl 2:S61-9. [PubMed:12846445 ]
Meyers RL, Book LS, O'Gorman MA, Jackson WD, Black RE, Johnson DG, Matlak ME: High-dose steroids, ursodeoxycholic acid, and chronic intravenous antibiotics improve bile flow after Kasai procedure in infants with biliary atresia. J Pediatr Surg. 2003 Mar;38(3):406-11. [PubMed:12632357 ]
Soderdahl G, Nowak G, Duraj F, Wang FH, Einarsson C, Ericzon BG: Ursodeoxycholic acid increased bile flow and affects bile composition in the early postoperative phase following liver transplantation. Transpl Int. 1998;11 Suppl 1:S231-8. [PubMed:9664985 ]
Nobilis M, Pour M, Kunes J, Kopecky J, Kvetina J, Svoboda Z, Sladkova K, Vortel J: High-performance liquid chromatographic determination of ursodeoxycholic acid after solid phase extraction of blood serum and detection-oriented derivatization. J Pharm Biomed Anal. 2001 Mar;24(5-6):937-46. [PubMed:11248487 ]
Hillaire S, Ballet F, Franco D, Setchell KD, Poupon R: Effects of ursodeoxycholic acid and chenodeoxycholic acid on human hepatocytes in primary culture. Hepatology. 1995 Jul;22(1):82-7. [PubMed:7601437 ]
Reyes H, Sjovall J: Bile acids and progesterone metabolites in intrahepatic cholestasis of pregnancy. Ann Med. 2000 Mar;32(2):94-106. [PubMed:10766400 ]
Hofmann AF: The continuing importance of bile acids in liver and intestinal disease. Arch Intern Med. 1999 Dec 13-27;159(22):2647-58. [PubMed:10597755 ]
Eriksson LS, Olsson R, Glauman H, Prytz H, Befrits R, Ryden BO, Einarsson K, Lindgren S, Wallerstedt S, Weden M: Ursodeoxycholic acid treatment in patients with primary biliary cirrhosis. A Swedish multicentre, double-blind, randomized controlled study. Scand J Gastroenterol. 1997 Feb;32(2):179-86. [PubMed:9051880 ]
Lindblad A, Glaumann H, Strandvik B: A two-year prospective study of the effect of ursodeoxycholic acid on urinary bile acid excretion and liver morphology in cystic fibrosis-associated liver disease. Hepatology. 1998 Jan;27(1):166-74. [PubMed:9425933 ]
Kowdley KV: Ursodeoxycholic acid therapy in hepatobiliary disease. Am J Med. 2000 Apr 15;108(6):481-6. [PubMed:10781781 ]
Geetha A, Surendran R: Effect of ursodeoxycholic acid on copper induced oxidation of low density lipoprotein. Pharmazie. 2005 Aug;60(8):609-13. [PubMed:16124405 ]
Brites D: Intrahepatic cholestasis of pregnancy: changes in maternal-fetal bile acid balance and improvement by ursodeoxycholic acid. Ann Hepatol. 2002 Jan-Mar;1(1):20-8. [PubMed:15114292 ]
Serrano MA, Brites D, Larena MG, Monte MJ, Bravo MP, Oliveira N, Marin JJ: Beneficial effect of ursodeoxycholic acid on alterations induced by cholestasis of pregnancy in bile acid transport across the human placenta. J Hepatol. 1998 May;28(5):829-39. [PubMed:9625319 ]
Maton PN, Murphy GM, Dowling RH: Ursodeoxycholic acid treatment of gallstones. Dose-response study and possible mechanism of action. Lancet. 1977 Dec 24-31;2(8052-8053):1297-301. [PubMed:74722 ]
Ikegami T, Matsuzaki Y, Al Rashid M, Ceryak S, Zhang Y, Bouscarel B: Enhancement of DNA topoisomerase I inhibitor-induced apoptosis by ursodeoxycholic acid. Mol Cancer Ther. 2006 Jan;5(1):68-79. [PubMed:16432164 ]
Crosignani A, Setchell KD, Invernizzi P, Larghi A, Rodrigues CM, Podda M: Clinical pharmacokinetics of therapeutic bile acids. Clin Pharmacokinet. 1996 May;30(5):333-58. [PubMed:8743334 ]
Baruch Y, Assy N, Weisbruch F, Reisner SA, Rinkevich D, Enat R, Blendis LM, Bomzon A: A pilot study on the hemodynamic effect of short-term ursodeoxycholic acid therapy in patients with stable liver cirrhosis. Am J Gastroenterol. 1999 Oct;94(10):3000-4. [PubMed:10520859 ]
Marschall HU, Wagner M, Zollner G, Fickert P, Diczfalusy U, Gumhold J, Silbert D, Fuchsbichler A, Benthin L, Grundstrom R, Gustafsson U, Sahlin S, Einarsson C, Trauner M: Complementary stimulation of hepatobiliary transport and detoxification systems by rifampicin and ursodeoxycholic acid in humans. Gastroenterology. 2005 Aug;129(2):476-85. [PubMed:16083704 ]
Guarino MP, Carotti S, Sarzano M, Alloni R, Vanni M, Grosso M, Sironi G, Maffettone PL, Cicala M: Short-term ursodeoxycholic acid treatment improves gallbladder bile turnover in gallstone patients: a randomized trial. Neurogastroenterol Motil. 2005 Oct;17(5):680-6. [PubMed:16185306 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Aldo-keto reductase family 1 member C1

General function:: Involved in oxidoreductase activity
Specific function:: Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:: AKR1C1
Uniprot ID:: Q04828
Molecular weight:: 36788.02

Enzyme Details

2. Aldo-keto reductase family 1 member C2

General function:: Involved in oxidoreductase activity
Specific function:: Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent androgen 5-alpha-dihydrotestosterone (5-alpha-DHT) to 5-alpha-androstane-3-alpha,17-beta-diol (3-alpha-diol). Has a high bile-binding ability.
Gene Name:: AKR1C2
Uniprot ID:: P52895
Molecular weight:: 15747.91

Enzyme Details

3. 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

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Showing metabocard for Ursodeoxycholic acid (HMDB0000946)

MOL for HMDB0000946 (Ursodeoxycholic acid)

3D MOL for HMDB0000946 (Ursodeoxycholic acid)

3D SDF for HMDB0000946 (Ursodeoxycholic acid)

3D-SDF for HMDB0000946 (Ursodeoxycholic acid)

PDB for HMDB0000946 (Ursodeoxycholic acid)

3D PDB for HMDB0000946 (Ursodeoxycholic acid)

SMILES for HMDB0000946 (Ursodeoxycholic acid)

INCHI for HMDB0000946 (Ursodeoxycholic acid)

Structure for HMDB0000946 (Ursodeoxycholic acid)

3D Structure for HMDB0000946 (Ursodeoxycholic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

Transporters

References

References