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

enzymes (1)transporters (8) Show 9 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:06 UTC

HMDB ID

HMDB0000865

Secondary Accession Numbers

HMDB00865

Metabolite Identification

Common Name

Muricholic acid

Description

A bile acid. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ).

Structure

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


  Mrv1652304202019442D          

 34 37  0  0  1  0            999 V2000
   10.9098   -4.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1292   -4.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9701   -5.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1894   -5.7260    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5973   -5.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5312   -4.9252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0689   -3.5731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4271   -7.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7422   -8.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7980   -9.1330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5387   -9.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2237   -9.0363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9644   -9.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6493   -8.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5935   -8.1166    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2784   -7.6567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0785   -7.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5171   -7.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9882   -6.5261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2226   -6.8335    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4819   -6.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7969   -6.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8527   -7.7533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1678   -8.2132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2531   -6.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8211   -7.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3900   -9.3028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0202  -10.2226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1131   -9.5929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987   -9.9788    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5625   -7.1375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9804   -8.7413    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6431   -8.6652    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6912   -6.4011    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  1  6  2  0  0  0  0
  1  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 24  1  0  0  0  0
  8 24  1  0  0  0  0
 20 25  1  1  0  0  0
 24 26  1  1  0  0  0
 14 27  1  0  0  0  0
 13 28  1  0  0  0  0
 10 29  1  6  0  0  0
  4 19  1  0  0  0  0
 12 30  1  1  0  0  0
 15 31  1  1  0  0  0
 23 32  1  6  0  0  0
 16 33  1  6  0  0  0
 19 34  1  6  0  0  0
M  END

HMDB0000865
     RDKit          3D
Muricholic acid
 69 72  0  0  0  0  0  0  0  0999 V2000
   -3.9364   -1.4732   -1.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8055   -0.3775   -0.1131 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1076    0.4088   -0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2988   -0.4586    0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5642    0.3417    0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6605   -0.2131    0.3444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5763    1.6831   -0.2496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6097    0.4659   -0.3601 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5075    1.5852    0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3599    1.0478    1.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4417    0.7008    0.4572 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8830    0.1983    0.7684 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6923    1.1042    1.6827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2768    2.4114    1.6501 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1694    1.0655    1.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4252    2.0358    0.4121 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5222   -0.3196    0.9398 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9857   -0.5953    1.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8209    0.0390    0.0040 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9712    1.4103    0.1482 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2867   -0.3643   -1.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8395   -0.0513   -1.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9589   -0.5750   -0.4185 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8816   -2.0877   -0.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6142    0.0820   -0.5765 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8302   -0.6684   -1.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6024   -0.1969   -1.7319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2799   -0.2194   -0.3752 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3655   -1.6259    0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7964   -2.4888   -0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9430   -1.4413   -1.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2361   -1.3519   -2.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8267   -0.7980    0.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1131    1.2293    0.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2599    0.8222   -1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4004   -1.3799   -0.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2546   -0.7825    1.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1940    2.0636   -1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7423    0.9374   -1.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3971    1.7628    1.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1174    2.4778    0.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7585    0.1837    2.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0526    1.8867    2.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3291    1.6464   -0.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9310   -0.7924    1.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5925    0.7520    2.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3969    2.8466    2.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7439    1.3023    2.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8120    2.7914    0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9970   -1.0238    1.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2125   -1.6724    1.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3206   -0.1757    2.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8498   -0.3981    0.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9498    1.9006   -0.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8666    0.1456   -2.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4441   -1.4516   -1.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6421    1.0246   -1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5075   -0.5915   -2.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013   -2.4694   -0.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7720   -2.3411   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1653   -2.5637    0.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7509    1.1217   -0.9387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8293   -1.7770   -1.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3083   -0.5268   -2.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0453   -0.8781   -2.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5923    0.8192   -2.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.0241    0.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4271   -2.2800   -0.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1371   -1.8594    0.8261 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
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  1
 28  8  1  0
 28 11  1  0
 25 12  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  1
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  6
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  6
 12 45  1  1
 13 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  1
 18 51  1  0
 18 52  1  0
 19 53  1  6
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 24 59  1  0
 24 60  1  0
 24 61  1  0
 25 62  1  6
 26 63  1  0
 26 64  1  0
 27 65  1  0
 27 66  1  0
 29 67  1  0
 29 68  1  0
 29 69  1  0
M  END


  Mrv1652304202019442D          

 34 37  0  0  1  0            999 V2000
   10.9098   -4.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1292   -4.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9701   -5.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1894   -5.7260    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5973   -5.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5312   -4.9252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0689   -3.5731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4271   -7.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7422   -8.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7980   -9.1330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5387   -9.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2237   -9.0363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9644   -9.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6493   -8.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5935   -8.1166    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2784   -7.6567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0785   -7.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5171   -7.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9882   -6.5261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2226   -6.8335    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4819   -6.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7969   -6.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8527   -7.7533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1678   -8.2132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2531   -6.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8211   -7.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3900   -9.3028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0202  -10.2226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1131   -9.5929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987   -9.9788    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5625   -7.1375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9804   -8.7413    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6431   -8.6652    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6912   -6.4011    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  1  6  2  0  0  0  0
  1  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 24  1  0  0  0  0
  8 24  1  0  0  0  0
 20 25  1  1  0  0  0
 24 26  1  1  0  0  0
 14 27  1  0  0  0  0
 13 28  1  0  0  0  0
 10 29  1  6  0  0  0
  4 19  1  0  0  0  0
 12 30  1  1  0  0  0
 15 31  1  1  0  0  0
 23 32  1  6  0  0  0
 16 33  1  6  0  0  0
 19 34  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000865

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])C(O)C(O)[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/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21?,22?,23-,24-/m1/s1

> <INCHI_KEY>
DKPMWHFRUGMUKF-JDDNAIEOSA-N

> <FORMULA>
C24H40O5

> <MOLECULAR_WEIGHT>
408.5714

> <EXACT_MASS>
408.28757439

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
47.23405687250722

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2R,5R,7R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
2.716355646666667

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.6233491959118

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.595941876165357

> <JCHEM_PKA_STRONGEST_BASIC>
-2.69104497552095

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
110.55829999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.89e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2R,5R,7R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000865
     RDKit          3D
Muricholic acid
 69 72  0  0  0  0  0  0  0  0999 V2000
   -3.9364   -1.4732   -1.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8055   -0.3775   -0.1131 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1076    0.4088   -0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2988   -0.4586    0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5642    0.3417    0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6605   -0.2131    0.3444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5763    1.6831   -0.2496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6097    0.4659   -0.3601 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5075    1.5852    0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3599    1.0478    1.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4417    0.7008    0.4572 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8830    0.1983    0.7684 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6923    1.1042    1.6827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2768    2.4114    1.6501 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1694    1.0655    1.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4252    2.0358    0.4121 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5222   -0.3196    0.9398 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9857   -0.5953    1.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8209    0.0390    0.0040 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9712    1.4103    0.1482 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2867   -0.3643   -1.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8395   -0.0513   -1.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9589   -0.5750   -0.4185 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8816   -2.0877   -0.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6142    0.0820   -0.5765 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8302   -0.6684   -1.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6024   -0.1969   -1.7319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2799   -0.2194   -0.3752 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3655   -1.6259    0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7964   -2.4888   -0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9430   -1.4413   -1.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2361   -1.3519   -2.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8267   -0.7980    0.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1131    1.2293    0.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2599    0.8222   -1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4004   -1.3799   -0.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2546   -0.7825    1.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1940    2.0636   -1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7423    0.9374   -1.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3971    1.7628    1.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1174    2.4778    0.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7585    0.1837    2.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0526    1.8867    2.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3291    1.6464   -0.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9310   -0.7924    1.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5925    0.7520    2.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3969    2.8466    2.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7439    1.3023    2.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8120    2.7914    0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9970   -1.0238    1.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2125   -1.6724    1.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3206   -0.1757    2.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8498   -0.3981    0.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9498    1.9006   -0.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8666    0.1456   -2.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4441   -1.4516   -1.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6421    1.0246   -1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5075   -0.5915   -2.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013   -2.4694   -0.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7720   -2.3411   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1653   -2.5637    0.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7509    1.1217   -0.9387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8293   -1.7770   -1.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3083   -0.5268   -2.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0453   -0.8781   -2.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5923    0.8192   -2.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.0241    0.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4271   -2.2800   -0.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1371   -1.8594    0.8261 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
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  1
 28  8  1  0
 28 11  1  0
 25 12  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  1
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  6
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  6
 12 45  1  1
 13 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  1
 18 51  1  0
 18 52  1  0
 19 53  1  6
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 24 59  1  0
 24 60  1  0
 24 61  1  0
 25 62  1  6
 26 63  1  0
 26 64  1  0
 27 65  1  0
 27 66  1  0
 29 67  1  0
 29 68  1  0
 29 69  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0      20.365  -8.181   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.908  -8.679   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.611 -10.190   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.154 -10.689   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.048  -9.617   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      21.525  -9.194   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      20.662  -6.670   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.131 -14.653   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.852 -15.512   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.956 -17.048   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.339 -17.726   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.618 -16.868   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.000 -17.546   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.279 -16.687   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.175 -15.151   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.453 -14.293   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.947 -14.668   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.765 -13.364   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.778 -12.182   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.349 -12.756   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.966 -12.078   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.688 -12.936   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.792 -14.473   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.513 -15.331   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.406 -11.217   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.866 -13.202   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      15.661 -17.365   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      13.104 -19.082   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       7.678 -17.907   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0      11.944 -18.627   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      14.117 -13.323   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      13.030 -16.317   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      16.134 -16.175   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      18.090 -11.949   0.000  0.00  0.00           H+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4                                                            
CONECT    6    1                                                            
CONECT    7    1                                                            
CONECT    8    9   24                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   29                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   24   30                                             
CONECT   13   12   14   28                                                  
CONECT   14   13   15   27                                                  
CONECT   15   14   16   23   31                                             
CONECT   16   15   17   20   33                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20    4   34                                             
CONECT   20   19   16   21   25                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   15   24   32                                             
CONECT   24   23   12    8   26                                             
CONECT   25   20                                                            
CONECT   26   24                                                            
CONECT   27   14                                                            
CONECT   28   13                                                            
CONECT   29   10                                                            
CONECT   30   12                                                            
CONECT   31   15                                                            
CONECT   32   23                                                            
CONECT   33   16                                                            
CONECT   34   19                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

COMPND    HMDB0000865
HETATM    1  C1  UNL     1      -3.936  -1.473  -1.137  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.805  -0.377  -0.113  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.108   0.409  -0.178  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.299  -0.459   0.165  1.00  0.00           C  
HETATM    5  C5  UNL     1      -7.564   0.342   0.091  1.00  0.00           C  
HETATM    6  O1  UNL     1      -8.660  -0.213   0.344  1.00  0.00           O  
HETATM    7  O2  UNL     1      -7.576   1.683  -0.250  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.610   0.466  -0.360  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.508   1.585   0.691  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.360   1.048   1.574  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.442   0.701   0.457  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.883   0.198   0.768  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.692   1.104   1.683  1.00  0.00           C  
HETATM   14  O3  UNL     1       1.277   2.411   1.650  1.00  0.00           O  
HETATM   15  C12 UNL     1       3.169   1.065   1.363  1.00  0.00           C  
HETATM   16  O4  UNL     1       3.425   2.036   0.412  1.00  0.00           O  
HETATM   17  C13 UNL     1       3.522  -0.320   0.940  1.00  0.00           C  
HETATM   18  C14 UNL     1       4.986  -0.595   1.066  1.00  0.00           C  
HETATM   19  C15 UNL     1       5.821   0.039   0.004  1.00  0.00           C  
HETATM   20  O5  UNL     1       5.971   1.410   0.148  1.00  0.00           O  
HETATM   21  C16 UNL     1       5.287  -0.364  -1.341  1.00  0.00           C  
HETATM   22  C17 UNL     1       3.839  -0.051  -1.538  1.00  0.00           C  
HETATM   23  C18 UNL     1       2.959  -0.575  -0.419  1.00  0.00           C  
HETATM   24  C19 UNL     1       2.882  -2.088  -0.609  1.00  0.00           C  
HETATM   25  C20 UNL     1       1.614   0.082  -0.577  1.00  0.00           C  
HETATM   26  C21 UNL     1       0.830  -0.668  -1.580  1.00  0.00           C  
HETATM   27  C22 UNL     1      -0.602  -0.197  -1.732  1.00  0.00           C  
HETATM   28  C23 UNL     1      -1.280  -0.219  -0.375  1.00  0.00           C  
HETATM   29  C24 UNL     1      -1.365  -1.626   0.080  1.00  0.00           C  
HETATM   30  H1  UNL     1      -3.796  -2.489  -0.754  1.00  0.00           H  
HETATM   31  H2  UNL     1      -4.943  -1.441  -1.675  1.00  0.00           H  
HETATM   32  H3  UNL     1      -3.236  -1.352  -2.008  1.00  0.00           H  
HETATM   33  H4  UNL     1      -3.827  -0.798   0.936  1.00  0.00           H  
HETATM   34  H5  UNL     1      -5.113   1.229   0.561  1.00  0.00           H  
HETATM   35  H6  UNL     1      -5.260   0.822  -1.206  1.00  0.00           H  
HETATM   36  H7  UNL     1      -6.400  -1.380  -0.396  1.00  0.00           H  
HETATM   37  H8  UNL     1      -6.255  -0.782   1.250  1.00  0.00           H  
HETATM   38  H9  UNL     1      -7.194   2.064  -1.089  1.00  0.00           H  
HETATM   39  H10 UNL     1      -2.742   0.937  -1.371  1.00  0.00           H  
HETATM   40  H11 UNL     1      -3.397   1.763   1.260  1.00  0.00           H  
HETATM   41  H12 UNL     1      -2.117   2.478   0.150  1.00  0.00           H  
HETATM   42  H13 UNL     1      -1.759   0.184   2.108  1.00  0.00           H  
HETATM   43  H14 UNL     1      -1.053   1.887   2.200  1.00  0.00           H  
HETATM   44  H15 UNL     1      -0.329   1.646  -0.160  1.00  0.00           H  
HETATM   45  H16 UNL     1       0.931  -0.792   1.237  1.00  0.00           H  
HETATM   46  H17 UNL     1       1.592   0.752   2.741  1.00  0.00           H  
HETATM   47  H18 UNL     1       1.397   2.847   2.541  1.00  0.00           H  
HETATM   48  H19 UNL     1       3.744   1.302   2.295  1.00  0.00           H  
HETATM   49  H20 UNL     1       2.812   2.791   0.545  1.00  0.00           H  
HETATM   50  H21 UNL     1       2.997  -1.024   1.649  1.00  0.00           H  
HETATM   51  H22 UNL     1       5.212  -1.672   1.094  1.00  0.00           H  
HETATM   52  H23 UNL     1       5.321  -0.176   2.048  1.00  0.00           H  
HETATM   53  H24 UNL     1       6.850  -0.398   0.084  1.00  0.00           H  
HETATM   54  H25 UNL     1       5.950   1.901  -0.718  1.00  0.00           H  
HETATM   55  H26 UNL     1       5.867   0.146  -2.108  1.00  0.00           H  
HETATM   56  H27 UNL     1       5.444  -1.452  -1.466  1.00  0.00           H  
HETATM   57  H28 UNL     1       3.642   1.025  -1.747  1.00  0.00           H  
HETATM   58  H29 UNL     1       3.507  -0.591  -2.461  1.00  0.00           H  
HETATM   59  H30 UNL     1       3.901  -2.469  -0.316  1.00  0.00           H  
HETATM   60  H31 UNL     1       2.772  -2.341  -1.676  1.00  0.00           H  
HETATM   61  H32 UNL     1       2.165  -2.564   0.059  1.00  0.00           H  
HETATM   62  H33 UNL     1       1.751   1.122  -0.939  1.00  0.00           H  
HETATM   63  H34 UNL     1       0.829  -1.777  -1.413  1.00  0.00           H  
HETATM   64  H35 UNL     1       1.308  -0.527  -2.573  1.00  0.00           H  
HETATM   65  H36 UNL     1      -1.045  -0.878  -2.476  1.00  0.00           H  
HETATM   66  H37 UNL     1      -0.592   0.819  -2.171  1.00  0.00           H  
HETATM   67  H38 UNL     1      -0.412  -2.024   0.548  1.00  0.00           H  
HETATM   68  H39 UNL     1      -1.427  -2.280  -0.844  1.00  0.00           H  
HETATM   69  H40 UNL     1      -2.137  -1.859   0.826  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    8   33
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6    6    7
CONECT    7   38
CONECT    8    9   28   39
CONECT    9   10   40   41
CONECT   10   11   42   43
CONECT   11   12   28   44
CONECT   12   13   25   45
CONECT   13   14   15   46
CONECT   14   47
CONECT   15   16   17   48
CONECT   16   49
CONECT   17   18   23   50
CONECT   18   19   51   52
CONECT   19   20   21   53
CONECT   20   54
CONECT   21   22   55   56
CONECT   22   23   57   58
CONECT   23   24   25
CONECT   24   59   60   61
CONECT   25   26   62
CONECT   26   27   63   64
CONECT   27   28   65   66
CONECT   28   29
CONECT   29   67   68   69
END

HMDB0000865
     RDKit          3D
Muricholic acid
 69 72  0  0  0  0  0  0  0  0999 V2000
   -3.9364   -1.4732   -1.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8055   -0.3775   -0.1131 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1076    0.4088   -0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2988   -0.4586    0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5642    0.3417    0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6605   -0.2131    0.3444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5763    1.6831   -0.2496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6097    0.4659   -0.3601 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5075    1.5852    0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3599    1.0478    1.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4417    0.7008    0.4572 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8830    0.1983    0.7684 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6923    1.1042    1.6827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2768    2.4114    1.6501 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1694    1.0655    1.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4252    2.0358    0.4121 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5222   -0.3196    0.9398 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9857   -0.5953    1.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8209    0.0390    0.0040 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9712    1.4103    0.1482 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2867   -0.3643   -1.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8395   -0.0513   -1.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9589   -0.5750   -0.4185 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8816   -2.0877   -0.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6142    0.0820   -0.5765 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8302   -0.6684   -1.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6024   -0.1969   -1.7319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2799   -0.2194   -0.3752 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3655   -1.6259    0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7964   -2.4888   -0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9430   -1.4413   -1.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2361   -1.3519   -2.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8267   -0.7980    0.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1131    1.2293    0.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2599    0.8222   -1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4004   -1.3799   -0.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2546   -0.7825    1.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1940    2.0636   -1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7423    0.9374   -1.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3971    1.7628    1.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1174    2.4778    0.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7585    0.1837    2.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0526    1.8867    2.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3291    1.6464   -0.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9310   -0.7924    1.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5925    0.7520    2.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3969    2.8466    2.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7439    1.3023    2.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8120    2.7914    0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9970   -1.0238    1.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2125   -1.6724    1.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3206   -0.1757    2.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8498   -0.3981    0.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9498    1.9006   -0.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8666    0.1456   -2.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4441   -1.4516   -1.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6421    1.0246   -1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5075   -0.5915   -2.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013   -2.4694   -0.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7720   -2.3411   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1653   -2.5637    0.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7509    1.1217   -0.9387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8293   -1.7770   -1.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3083   -0.5268   -2.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0453   -0.8781   -2.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5923    0.8192   -2.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.0241    0.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4271   -2.2800   -0.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1371   -1.8594    0.8261 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
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  1
 28  8  1  0
 28 11  1  0
 25 12  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  1
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  6
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  6
 12 45  1  1
 13 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  1
 18 51  1  0
 18 52  1  0
 19 53  1  6
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 24 59  1  0
 24 60  1  0
 24 61  1  0
 25 62  1  6
 26 63  1  0
 26 64  1  0
 27 65  1  0
 27 66  1  0
 29 67  1  0
 29 68  1  0
 29 69  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Muricholate	Generator
(3alpha,5beta)-3,6,7-Trihydroxy-cholan-24-Oate	HMDB
(3alpha,5beta)-3,6,7-Trihydroxy-cholan-24-Oic acid	HMDB
3,6,7-Trihydroxy-5-cholanoate	HMDB
3,6,7-Trihydroxy-5-cholanoic acid	HMDB
3alpha,6alpha,7beta-Trihydroxy-5beta-cholanoate	HMDB
3alpha,6alpha,7beta-Trihydroxy-5beta-cholanoic acid	HMDB
Hyocholic acid	HMDB
Trihydroxy-5alpha-cholanoate	HMDB
Trihydroxy-5alpha-cholanoic acid	HMDB
3 alpha,6 alpha,7 beta-Trihydroxy-5 beta-cholanoic acid	HMDB
alpha-Muricholic acid	HMDB
beta-Muricholic acid	HMDB
Muricholic acid, (3alpha,5alpha,6alpha,7alpha)-isomer	HMDB
Muricholic acid, (3alpha,5beta,6alpha,7alpha)-isomer	HMDB
Muricholic acid, (3alpha,5beta,6alpha,7beta)-isomer	HMDB
Muricholic acid, (3alpha,5beta,6beta,7alpha)-isomer	HMDB
Muricholic acid, (3alpha,5beta,6beta,7beta)-isomer	HMDB
Muricholic acid, sodium salt	HMDB
Omega-muricholic acid	HMDB
Trihydroxy-5 alpha-cholanoic acid	HMDB
Muricholic acid	MeSH

Chemical Formula

C₂₄H₄₀O₅

Average Molecular Weight

408.5714

Monoisotopic Molecular Weight

408.28757439

IUPAC Name

(4R)-4-[(1S,2R,5R,7R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2R,5R,7R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

CAS Registry Number

39016-49-4

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])C(O)C(O)[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/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21?,22?,23-,24-/m1/s1

InChI Key

DKPMWHFRUGMUKF-JDDNAIEOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl 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

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0000865)

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

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	2.72	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.069 g/L	ALOGPS
logP	2.16	ALOGPS
logP	2.72	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.6	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.56 m³·mol⁻¹	ChemAxon
Polarizability	47.23 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	193.481	31661259
DarkChem	[M-H]-	190.536	31661259
AllCCS	[M+H]+	203.532	32859911
AllCCS	[M-H]-	201.036	32859911
DeepCCS	[M-2H]-	238.169	30932474
DeepCCS	[M+Na]+	212.186	30932474
AllCCS	[M+H]+	203.5	32859911
AllCCS	[M+H-H2O]+	201.5	32859911
AllCCS	[M+NH4]+	205.4	32859911
AllCCS	[M+Na]+	206.0	32859911
AllCCS	[M-H]-	201.0	32859911
AllCCS	[M+Na-2H]-	202.4	32859911
AllCCS	[M+HCOO]-	204.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Muricholic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])C(O)C(O)[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O	3386.6	Standard polar	33892256
Muricholic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])C(O)C(O)[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O	3384.5	Standard non polar	33892256
Muricholic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])C(O)C(O)[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O	3611.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Muricholic acid,1TMS,isomer #1	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)C(O)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3465.8	Semi standard non polar	33892256
Muricholic acid,1TMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C(O)C(O[Si](C)(C)C)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3478.3	Semi standard non polar	33892256
Muricholic acid,1TMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C(O)C(O)[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3515.4	Semi standard non polar	33892256
Muricholic acid,1TMS,isomer #4	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C(O)C(O)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3442.9	Semi standard non polar	33892256
Muricholic acid,2TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)C(O)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3401.5	Semi standard non polar	33892256
Muricholic acid,2TMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)C(O[Si](C)(C)C)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3384.2	Semi standard non polar	33892256
Muricholic acid,2TMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)C(O)[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3429.5	Semi standard non polar	33892256
Muricholic acid,2TMS,isomer #4	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C(O)C(O[Si](C)(C)C)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3405.4	Semi standard non polar	33892256
Muricholic acid,2TMS,isomer #5	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C(O)C(O[Si](C)(C)C)[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3445.7	Semi standard non polar	33892256
Muricholic acid,2TMS,isomer #6	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C(O)C(O)[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3466.5	Semi standard non polar	33892256
Muricholic acid,3TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)C(O[Si](C)(C)C)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3351.9	Semi standard non polar	33892256
Muricholic acid,3TMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)C(O)[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3383.4	Semi standard non polar	33892256
Muricholic acid,3TMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)C(O[Si](C)(C)C)[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3392.0	Semi standard non polar	33892256
Muricholic acid,3TMS,isomer #4	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C(O)C(O[Si](C)(C)C)[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3396.3	Semi standard non polar	33892256
Muricholic acid,4TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)C(O[Si](C)(C)C)[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3364.6	Semi standard non polar	33892256
Muricholic acid,1TBDMS,isomer #1	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)C(O)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3679.8	Semi standard non polar	33892256
Muricholic acid,1TBDMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C(O)C(O[Si](C)(C)C(C)(C)C)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3698.9	Semi standard non polar	33892256
Muricholic acid,1TBDMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C(O)C(O)[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3752.9	Semi standard non polar	33892256
Muricholic acid,1TBDMS,isomer #4	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C(O)C(O)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3710.8	Semi standard non polar	33892256
Muricholic acid,2TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)C(O)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3837.1	Semi standard non polar	33892256
Muricholic acid,2TBDMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3814.9	Semi standard non polar	33892256
Muricholic acid,2TBDMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)C(O)[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3855.3	Semi standard non polar	33892256
Muricholic acid,2TBDMS,isomer #4	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C(O)C(O[Si](C)(C)C(C)(C)C)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3850.6	Semi standard non polar	33892256
Muricholic acid,2TBDMS,isomer #5	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C(O)C(O[Si](C)(C)C(C)(C)C)[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3888.0	Semi standard non polar	33892256
Muricholic acid,2TBDMS,isomer #6	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C(O)C(O)[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3943.0	Semi standard non polar	33892256
Muricholic acid,3TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3990.4	Semi standard non polar	33892256
Muricholic acid,3TBDMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)C(O)[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	4024.1	Semi standard non polar	33892256
Muricholic acid,3TBDMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	4024.4	Semi standard non polar	33892256
Muricholic acid,3TBDMS,isomer #4	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C(O)C(O[Si](C)(C)C(C)(C)C)[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	4047.6	Semi standard non polar	33892256
Muricholic acid,4TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	4194.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-0229000000-ffb958adac1bd99cb8c8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (4 TMS) - 70eV, Positive	splash10-001i-1110029000-d964e134586fffeb9133	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muricholic acid GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muricholic acid 10V, Positive-QTOF	splash10-006x-0009100000-aeaf5bcdde74fe1ddf76	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muricholic acid 20V, Positive-QTOF	splash10-00dm-0009000000-4af1ebd01d1d670d4f42	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muricholic acid 40V, Positive-QTOF	splash10-003u-2209000000-454d741b691e592d251a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muricholic acid 10V, Negative-QTOF	splash10-0a4i-0007900000-e501198616f74730538f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muricholic acid 20V, Negative-QTOF	splash10-052r-1009300000-9efc23876fa89e243bc6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muricholic acid 40V, Negative-QTOF	splash10-0a4l-9007000000-e10e02b21078730f3ff9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muricholic acid 10V, Negative-QTOF	splash10-0a4i-0001900000-3a052136aaad1f7a6938	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muricholic acid 20V, Negative-QTOF	splash10-0a4r-0007900000-22aa0ad4e0928aedf2ca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muricholic acid 40V, Negative-QTOF	splash10-0a4i-1007900000-6419c8b1ffa27ffadfc8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muricholic acid 10V, Positive-QTOF	splash10-0a4i-0009500000-dcb14c8cf8d9d980be59	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muricholic acid 20V, Positive-QTOF	splash10-000j-2389100000-31f9fcf2f00a46e40c20	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muricholic acid 40V, Positive-QTOF	splash10-0002-9650000000-1b93af04c335777ff295	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Gall Bladder
Intestine
Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

106701

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Muricholic_acid

METLIN ID

5826

PubChem Compound

119473

PDB ID

Not Available

ChEBI ID

134216

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Aranda G; Bertranne M; Fetizon M; Infante R Synthesis of 6 alpha-tritiated beta-muricholic acid for use as a molecular probe. Steroids (1992), 57(4), 205-7.

Material Safety Data Sheet (MSDS)

Not Available

General References

Nakashima T, Yoh T, Sumida Y, Kakisaka Y, Mitsuyoshi H: Differences in the efficacy of ursodeoxycholic acid and bile acid metabolism between viral liver diseases and primary biliary cirrhosis. J Gastroenterol Hepatol. 2001 May;16(5):541-7. [PubMed:11350551 ]
Lundell K, Wikvall K: Gene structure of pig sterol 12alpha-hydroxylase (CYP8B1) and expression in fetal liver: comparison with expression of taurochenodeoxycholic acid 6alpha-hydroxylase (CYP4A21). Biochim Biophys Acta. 2003 Nov 15;1634(3):86-96. [PubMed:14643796 ]
Strandvik B, Wikstrom SA: Tetrahydroxylated bile acids in healthy human newborns. Eur J Clin Invest. 1982 Aug;12(4):301-5. [PubMed:6814920 ]
Bremmelgaard A, Sjovall J: Hydroxylation of cholic, chenodeoxycholic, and deoxycholic acids in patients with intrahepatic cholestasis. J Lipid Res. 1980 Nov;21(8):1072-81. [PubMed:7462803 ]
Kimura A, Yamakawa R, Ushijima K, Fujisawa T, Kuriya N, Kato H, Inokuchi T, Mahara R, Kurosawa T, Tohma M: Fetal bile acid metabolism during infancy: analysis of 1 beta-hydroxylated bile acids in urine, meconium and feces. Hepatology. 1994 Oct;20(4 Pt 1):819-24. [PubMed:7927221 ]
Kayahara T, Tamura T, Amuro Y, Higashino K, Igimi H, Uchida K: Delta 22-beta-muricholic acid in monoassociated rats and conventional rats. Lipids. 1994 Apr;29(4):289-96. [PubMed:8177022 ]
Nakashima T, Sakamoto Y, Inaba K, Mitsuyoshi H, Ishikawa H, Nakajima Y, Sakai M, Shima T, Kashima K: A paucity of unusual trihydroxy bile acids in the urine of patients with severe liver diseases. Hepatology. 1999 May;29(5):1518-22. [PubMed:10216137 ]
Narushima S, Itoh K, Takamine F, Uchida K: Absence of cecal secondary bile acids in gnotobiotic mice associated with two human intestinal bacteria with the ability to dehydroxylate bile acids in vitro. Microbiol Immunol. 1999;43(9):893-7. [PubMed:10553682 ]
Kano M, Matsumoto M, Kamano T, Tsurumaru M: ELISA determination of serum hyocholic acid concentrations in humans and their possible clinical significance. Hepatogastroenterology. 1999 Mar-Apr;46(26):983-4. [PubMed:10370651 ]
Ushijima K, Kimura A, Inokuchi T, Yamato Y, Maeda K, Yamashita Y, Nakashima E, Kato H: Placental transport of bile acids: analysis of bile acids in maternal serum and urine, umbilical cord blood, and amniotic fluid. Kurume Med J. 2001;48(2):87-91. [PubMed:11501503 ]
van Berge Henegouwen GP, Brandt KH, Eyssen H, Parmentier G: Sulphated and unsulphated bile acids in serum, bile, and urine of patients with cholestasis. Gut. 1976 Nov;17(11):861-9. [PubMed:1001976 ]
St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. [PubMed:11316487 ]
Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. [PubMed:16037564 ]
Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. [PubMed:12576301 ]
Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]

Enzymes

Enzyme Details

1. Gastrotropin

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

References

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

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1B3

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

Enzyme Details

2. Solute carrier organic anion transporter family member 1B1

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

References

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

Enzyme Details

3. Canalicular multispecific organic anion transporter 2

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

Enzyme Details

4. Bile salt export pump

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

Enzyme Details

5. Ileal sodium/bile acid cotransporter

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

References

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

Enzyme Details

6. Sodium/bile acid cotransporter

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

Enzyme Details

7. Solute carrier organic anion transporter family member 1A2

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

Enzyme Details

8. Solute carrier organic anion transporter family member 4A1

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

Showing metabocard for Muricholic acid (HMDB0000865)

MOL for HMDB0000865 (Muricholic acid)

3D MOL for HMDB0000865 (Muricholic acid)

3D SDF for HMDB0000865 (Muricholic acid)

3D-SDF for HMDB0000865 (Muricholic acid)

PDB for HMDB0000865 (Muricholic acid)

3D PDB for HMDB0000865 (Muricholic acid)

SMILES for HMDB0000865 (Muricholic acid)

INCHI for HMDB0000865 (Muricholic acid)

Structure for HMDB0000865 (Muricholic acid)

3D Structure for HMDB0000865 (Muricholic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Transporters

References

References