MiMeDB: Showing metabocard for Ursodeoxycholic acid (MMDBc0000172)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:38:31 UTC

Update Date

2024-10-11 03:32:32 UTC

Metabolite ID

MMDBc0000172

Metabolite Identification

Common Name

Ursodeoxycholic acid

Description

Ursodeoxycholic acid is an epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic. [PubChem]

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
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 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
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 18 20  1  0
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 27 28  1  1
 27  8  1  0
 27 11  1  0
 24 12  1  0
 22 16  1  0
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  1 31  1  0
  2 32  1  1
  3 33  1  0
  3 34  1  0
  4 35  1  0
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  7 37  1  0
  8 38  1  6
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 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
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    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
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  6 10  1  0  0  0  0
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  7  8  1  0  0  0  0
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  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>
MMDBc0000172

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₂₄H₄₀O₄

Average Mass

392.572

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Adrenal Cortex
Bladder
Blood
Feces
Fibroblasts
Intestine
Liver
Placenta
Skeletal Muscle
Urine

Tissue Locations

Adrenal Cortex
Bladder
Fibroblasts
Intestine
Liver
Placenta
Skeletal Muscle

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192053	Aldo-keto reductase family 1 member C1	Unknown	Q04828	Homo sapiens
MMDBp0192054	Aldo-keto reductase family 1 member C2	Unknown	P52895	Homo sapiens
MMDBp0192108	Solute carrier organic anion transporter family member 1B3	Transporter	Q9NPD5	Homo sapiens
MMDBp0192115	Solute carrier organic anion transporter family member 1B1	Transporter	Q9Y6L6	Homo sapiens
MMDBp0193395	Canalicular multispecific organic anion transporter 2	Transporter	O15438	Homo sapiens
MMDBp0193400	Bile salt export pump	Transporter	O95342	Homo sapiens
MMDBp0193547	Ileal sodium/bile acid cotransporter	Transporter	Q12908	Homo sapiens
MMDBp0193577	Sodium/bile acid cotransporter	Transporter	Q14973	Homo sapiens
MMDBp0193639	Solute carrier organic anion transporter family member 1A2	Transporter	P46721	Homo sapiens
MMDBp0193865	Solute carrier organic anion transporter family member 4A1	Transporter	Q96BD0	Homo sapiens
MMDBp0195864	Gastrotropin	Unknown	P51161	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0038904	ursodeoxycholoyl-CoA	Ursodeoxycholic acid	Thioesterase TesA	Hydrolysis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Cystic fibrosis	Increased	Association	Human Blood	HMDB	15185309
Primary biliary cirrhosis	Increased	Association	Human Urine	HMDB	2621422
Primary biliary cirrhosis	Increased	Association	Human Blood	HMDB	2621422

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Firmicutes	14	Human stool; Human ; Human feces; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	4	Human ; Human supragingival plaque; Human saliva; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Actinobacteria	2	Human ; Human supragingival plaque; Human saliva; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Firmicutes	1	Human stool; Human ; Human feces; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs	U.S. Environmental Protection Agency	CompTox
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.48	0.16			uM	Adult (>18 years old)	Both	Cystic fibrosis	HMDB	15185309
Human Blood	Detected and Quantified	0.61	0.27			uM	Children (1-13 years old)	Both	Cystic fibrosis	HMDB	15185309
Human Urine	Detected and Quantified	0.29		0.056	0.98	umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	HMDB	2621422
Human Blood	Detected and Quantified	1.7		0.7	3.0	uM	Adult (>18 years old)	Both	Biliary cirrhosis	HMDB	2621422
Human Urine	Detected and Quantified	12.5		0.7	53.9	umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	HMDB	2621422
Human Blood	Detected and Quantified	24.5		2.3	51.3	uM	Adult (>18 years old)	Both	Biliary cirrhosis	HMDB	2621422
Human Urine	Detected and Quantified	0.022		0.013	0.030	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Blood	Detected and Quantified	0.16	0.03			uM	Adult (>18 years old)	Both	Normal	HMDB	15185309
Human Feces	Detected and Quantified	27.05	61.13			nmol/g dry feces	Not Specified	Not Specified	Normal	HMDB	22664055
Human Adrenal cortex	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Bladder	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	23940645
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000946

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.1016/s0140-6736(77)90358-0. [PubMed:74722 ]
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 ]
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. doi: 10.2165/00003088-199630050-00002. [PubMed:8743334 ]
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. doi: 10.3109/00365529709000190. [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. doi: 10.1002/hep.510270126. [PubMed:9425933 ]
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. doi: 10.1016/s0168-8278(98)80234-1. [PubMed:9625319 ]
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. doi: 10.1007/s001470050467. [PubMed:9664985 ]
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. doi: 10.1111/j.1572-0241.1999.01450.x. [PubMed:10520859 ]
Hofmann AF: The continuing importance of bile acids in liver and intestinal disease. Arch Intern Med. 1999 Dec 13-27;159(22):2647-58. doi: 10.1001/archinte.159.22.2647. [PubMed:10597755 ]
Reyes H, Sjovall J: Bile acids and progesterone metabolites in intrahepatic cholestasis of pregnancy. Ann Med. 2000 Mar;32(2):94-106. doi: 10.3109/07853890009011758. [PubMed:10766400 ]
Kowdley KV: Ursodeoxycholic acid therapy in hepatobiliary disease. Am J Med. 2000 Apr 15;108(6):481-6. doi: 10.1016/s0002-9343(00)00318-1. [PubMed:10781781 ]
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. doi: 10.1016/s0731-7085(00)00563-x. [PubMed:11248487 ]
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. doi: 10.1053/jpsu.2003.50069. [PubMed:12632357 ]
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. doi: 10.1016/s1590-8658(03)00053-7. [PubMed:12846445 ]
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 ]
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. doi: 10.1002/hep.20238. [PubMed:15185309 ]
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. doi: 10.1016/j.gastro.2005.05.009. [PubMed:16083704 ]
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 ]
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. doi: 10.1111/j.1365-2982.2005.00683.x. [PubMed:16185306 ]
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. doi: 10.1158/1535-7163.MCT-05-0107. [PubMed:16432164 ]

Showing metabocard for Ursodeoxycholic acid (MMDBc0000172)

MOL for #<Metabolite:0x00007f924112b5f8>

3D MOL for #<Metabolite:0x00007f924112b5f8>

3D SDF for #<Metabolite:0x00007f924112b5f8>

3D-SDF for #<Metabolite:0x00007f924112b5f8>

PDB for #<Metabolite:0x00007f924112b5f8>

3D PDB for #<Metabolite:0x00007f924112b5f8>

SMILES for #<Metabolite:0x00007f924112b5f8>

INCHI for #<Metabolite:0x00007f924112b5f8>

Structure for #<Metabolite:0x00007f924112b5f8>

3D Structure for #<Metabolite:0x00007f924112b5f8>