NP-MRD: Showing NP-Card for Ursodeoxycholic acid (NP0000661)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-10-07 20:41:50 UTC

NP-MRD ID

NP0000661

Secondary Accession Numbers

None

Natural Product 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>
NP0000661

> <DATABASE_NAME>
NP-MRD

> <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 NMR Assignments

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 Mass

392.5720 Da

Monoisotopic Mass

392.29266 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

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

Species Where Detected

Species Name	Source	Reference
Bos taurus domesticus GMELIN	KNApSAcK Database	22123792
Homo sapiens (Urine)	KNApSAcK Database	22123792

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	203 °C	Not Available
Boiling Point	547.10 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.02 mg/mL	Not Available
LogP	3.00	Roda, A., Minutello, A., Angellotti, M. A., & Fini, A. (1990). Bile acid structure-activity relationship: evaluation of bile acid lipophilicity using 1-octanol/water partition coefficient and reverse phase HPLC. Journal of lipid research, 31(8), 1433-1443.

Predicted 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

External Links

HMDB ID

HMDB0000946

DrugBank ID

DB01586

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1296231

References

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 ]

Showing NP-Card for Ursodeoxycholic acid (NP0000661)

MOL for NP0000661 (Ursodeoxycholic acid)

3D MOL for NP0000661 (Ursodeoxycholic acid)

3D SDF for NP0000661 (Ursodeoxycholic acid)

3D-SDF for NP0000661 (Ursodeoxycholic acid)

PDB for NP0000661 (Ursodeoxycholic acid)

3D PDB for NP0000661 (Ursodeoxycholic acid)

SMILES for NP0000661 (Ursodeoxycholic acid)

INCHI for NP0000661 (Ursodeoxycholic acid)

Structure for NP0000661 (Ursodeoxycholic acid)

3D Structure for NP0000661 (Ursodeoxycholic acid)