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

enzymes (1)transporters (8) Show 9 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-09-22 18:34:14 UTC

HMDB ID

HMDB0000760

Secondary Accession Numbers

HMDB00760

Metabolite Identification

Common Name

Hyocholic acid

Description

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

Structure

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


  Mrv1652305231919592D          

 33 36  0  0  1  0            999 V2000
   11.5004   -4.6154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.2175   -5.0281    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7865   -5.0216    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5101   -3.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9380   -4.6220    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.2077   -5.8698    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7865   -5.8566    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0660   -4.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7865   -4.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2241   -3.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9478   -3.7869    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7239   -4.8709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5004   -6.2627    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9217   -6.3249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0660   -6.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3586   -5.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7306   -3.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1639   -2.9945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1988   -4.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5233   -7.0978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3586   -5.8468    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.0155   -2.7489    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6218   -6.2496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8275   -2.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4553   -2.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3614   -3.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1636   -3.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7074   -3.6854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4486   -2.2772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2875   -5.4047    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4304   -4.2388    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1574   -5.4112    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8093   -6.9013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1 30  1  6  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2 31  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  1  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  5 32  1  6  0  0  0
  6 13  1  0  0  0  0
  6 14  1  6  0  0  0
  7 15  1  0  0  0  0
  7 13  1  0  0  0  0
  7 33  1  1  0  0  0
  8 16  1  0  0  0  0
 10 11  1  0  0  0  0
 11 17  1  0  0  0  0
 11 18  1  1  0  0  0
 12 19  1  0  0  0  0
 13 20  1  6  0  0  0
 15 21  1  0  0  0  0
 16 21  1  0  0  0  0
 17 22  1  0  0  0  0
 17 19  1  0  0  0  0
 21 23  1  6  0  0  0
 22 24  1  0  0  0  0
 22 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
M  END

HMDB0000760
     RDKit          3D
Hyocholic acid
 69 72  0  0  0  0  0  0  0  0999 V2000
    3.5952    0.2066   -1.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7187    0.2169    0.1202 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0954   -0.1016    0.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2106    0.7896    0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4892    0.9415   -1.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0911    1.9251   -1.8484 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2245   -0.0348   -1.8327 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6697   -0.5733    0.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6355   -2.0313    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1736   -2.3899    0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5017   -1.1717    0.1749 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9134   -0.9650    0.5703 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8350   -2.0985    0.2587 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2394   -3.1499   -0.4315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0474   -1.7044   -0.5608 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7443   -1.6385   -1.9060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7345   -0.4872   -0.0369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8616   -0.1537   -0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6176    1.0809   -0.5518 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5943    1.3204   -1.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6457    2.2108   -0.4658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2045    1.7710   -0.7620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7857    0.6673    0.1843 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9463    1.2194    1.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3545    0.3004   -0.1344 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4906    1.4712    0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9908    1.1845    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2992   -0.0598    0.8690 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8430    0.0830    2.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5196   -0.2640   -1.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5099    1.2114   -1.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7655   -0.4650   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5907    1.3320    0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0413   -0.1036    1.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3776   -1.1675    0.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1528    0.3746    0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1181    1.7997    0.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7713    0.2310   -2.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0772   -0.6049    1.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302   -2.1685   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2996   -2.6710    1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9418   -2.6140    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0197   -3.3154    0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -1.0614   -0.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0005   -0.7475    1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2487   -2.5611    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6454   -4.0335   -0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7801   -2.5576   -0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6415   -2.5878   -2.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2285   -0.7642    0.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5914   -1.0036   -0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5339   -0.1059   -2.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0529    0.8743    0.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5237    2.2056   -1.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6203    2.6366    0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8578    3.0141   -1.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1813    1.4468   -1.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6145    2.7138   -0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0390    1.1581    1.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7124    2.3009    1.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3421    0.6885    2.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235    0.0848   -1.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7716    2.0307    1.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6551    2.2164   -0.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4657    2.0731    0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2786    1.1400   -0.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0434    0.8147    2.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7405    0.5164    2.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6799   -0.8960    2.8029 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  1
 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  0
  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  1
 14 47  1  0
 15 48  1  6
 16 49  1  0
 17 50  1  1
 18 51  1  0
 18 52  1  0
 19 53  1  1
 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


  Mrv1652305231919592D          

 33 36  0  0  1  0            999 V2000
   11.5004   -4.6154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.2175   -5.0281    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7865   -5.0216    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5101   -3.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9380   -4.6220    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.2077   -5.8698    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7865   -5.8566    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0660   -4.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7865   -4.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2241   -3.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9478   -3.7869    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7239   -4.8709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5004   -6.2627    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9217   -6.3249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0660   -6.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3586   -5.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7306   -3.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1639   -2.9945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1988   -4.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5233   -7.0978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3586   -5.8468    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.0155   -2.7489    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6218   -6.2496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8275   -2.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4553   -2.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3614   -3.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1636   -3.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7074   -3.6854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4486   -2.2772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2875   -5.4047    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4304   -4.2388    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1574   -5.4112    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8093   -6.9013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1 30  1  6  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2 31  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  1  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  5 32  1  6  0  0  0
  6 13  1  0  0  0  0
  6 14  1  6  0  0  0
  7 15  1  0  0  0  0
  7 13  1  0  0  0  0
  7 33  1  1  0  0  0
  8 16  1  0  0  0  0
 10 11  1  0  0  0  0
 11 17  1  0  0  0  0
 11 18  1  1  0  0  0
 12 19  1  0  0  0  0
 13 20  1  6  0  0  0
 15 21  1  0  0  0  0
 16 21  1  0  0  0  0
 17 22  1  0  0  0  0
 17 19  1  0  0  0  0
 21 23  1  6  0  0  0
 22 24  1  0  0  0  0
 22 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000760

> <DATABASE_NAME>
hmdb

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

> <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-NNFRHCBVSA-N

> <FORMULA>
C24H40O5

> <MOLECULAR_WEIGHT>
408.5714

> <EXACT_MASS>
408.28757439

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
46.85711134621157

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2R,5R,7R,8R,9S,10S,11S,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>
110.55829999999996

> <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,8R,9S,10S,11S,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

$$$$

HMDB0000760
     RDKit          3D
Hyocholic acid
 69 72  0  0  0  0  0  0  0  0999 V2000
    3.5952    0.2066   -1.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7187    0.2169    0.1202 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0954   -0.1016    0.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2106    0.7896    0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4892    0.9415   -1.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0911    1.9251   -1.8484 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2245   -0.0348   -1.8327 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6697   -0.5733    0.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6355   -2.0313    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1736   -2.3899    0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5017   -1.1717    0.1749 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9134   -0.9650    0.5703 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8350   -2.0985    0.2587 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2394   -3.1499   -0.4315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0474   -1.7044   -0.5608 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7443   -1.6385   -1.9060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7345   -0.4872   -0.0369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8616   -0.1537   -0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6176    1.0809   -0.5518 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5943    1.3204   -1.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6457    2.2108   -0.4658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2045    1.7710   -0.7620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7857    0.6673    0.1843 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9463    1.2194    1.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3545    0.3004   -0.1344 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4906    1.4712    0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9908    1.1845    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2992   -0.0598    0.8690 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8430    0.0830    2.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5196   -0.2640   -1.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5099    1.2114   -1.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7655   -0.4650   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5907    1.3320    0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0413   -0.1036    1.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3776   -1.1675    0.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1528    0.3746    0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1181    1.7997    0.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7713    0.2310   -2.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0772   -0.6049    1.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302   -2.1685   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2996   -2.6710    1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9418   -2.6140    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0197   -3.3154    0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -1.0614   -0.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0005   -0.7475    1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2487   -2.5611    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6454   -4.0335   -0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7801   -2.5576   -0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6415   -2.5878   -2.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2285   -0.7642    0.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5914   -1.0036   -0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5339   -0.1059   -2.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0529    0.8743    0.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5237    2.2056   -1.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6203    2.6366    0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8578    3.0141   -1.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1813    1.4468   -1.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6145    2.7138   -0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0390    1.1581    1.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7124    2.3009    1.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3421    0.6885    2.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235    0.0848   -1.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7716    2.0307    1.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6551    2.2164   -0.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4657    2.0731    0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2786    1.1400   -0.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0434    0.8147    2.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7405    0.5164    2.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6799   -0.8960    2.8029 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  1
 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  0
  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  1
 14 47  1  0
 15 48  1  6
 16 49  1  0
 17 50  1  1
 18 51  1  0
 18 52  1  0
 19 53  1  1
 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                                 23-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAY-19         0                                  
HETATM    1  C   UNK     0      21.467  -8.615   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.806  -9.386   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.135  -9.374   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.486  -7.044   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.151  -8.628   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.788 -10.957   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.135 -10.932   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.790  -8.615   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.135  -7.833   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.818  -6.280   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.169  -7.069   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.618  -9.092   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.467 -11.690   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      24.121 -11.806   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      18.790 -11.690   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.469  -9.386   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.630  -6.616   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.573  -5.590   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.504  -7.833   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      21.510 -13.249   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      17.469 -10.914   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.162  -5.131   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      16.094 -11.666   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      27.678  -4.819   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      25.117  -3.957   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      28.675  -5.969   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      30.172  -5.694   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      31.187  -6.879   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      30.704  -4.251   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0      21.070 -10.089   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      23.203  -7.912   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      24.560 -10.101   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      20.177 -12.882   0.000  0.00  0.00           H+0
CONECT    1    2    3    4   30                                             
CONECT    2    1    5    6   31                                             
CONECT    3    1    7    8    9                                             
CONECT    4    1   10                                                       
CONECT    5    2   11   12   32                                             
CONECT    6    2   13   14                                                  
CONECT    7    3   15   13   33                                             
CONECT    8    3   16                                                       
CONECT    9    3                                                            
CONECT   10    4   11                                                       
CONECT   11    5   10   17   18                                             
CONECT   12    5   19                                                       
CONECT   13    6    7   20                                                  
CONECT   14    6                                                            
CONECT   15    7   21                                                       
CONECT   16    8   21                                                       
CONECT   17   11   22   19                                                  
CONECT   18   11                                                            
CONECT   19   12   17                                                       
CONECT   20   13                                                            
CONECT   21   15   16   23                                                  
CONECT   22   17   24   25                                                  
CONECT   23   21                                                            
CONECT   24   22   26                                                       
CONECT   25   22                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    1                                                            
CONECT   31    2                                                            
CONECT   32    5                                                            
CONECT   33    7                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0000760
HETATM    1  C1  UNL     1       3.595   0.207  -1.354  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.719   0.217   0.120  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.095  -0.102   0.602  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.211   0.790   0.248  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.489   0.941  -1.179  1.00  0.00           C  
HETATM    6  O1  UNL     1       6.091   1.925  -1.848  1.00  0.00           O  
HETATM    7  O2  UNL     1       7.224  -0.035  -1.833  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.670  -0.573   0.866  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.635  -2.031   0.480  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.174  -2.390   0.673  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.502  -1.172   0.175  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.913  -0.965   0.570  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.835  -2.099   0.259  1.00  0.00           C  
HETATM   14  O3  UNL     1      -1.239  -3.150  -0.431  1.00  0.00           O  
HETATM   15  C12 UNL     1      -3.047  -1.704  -0.561  1.00  0.00           C  
HETATM   16  O4  UNL     1      -2.744  -1.638  -1.906  1.00  0.00           O  
HETATM   17  C13 UNL     1      -3.734  -0.487  -0.037  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.862  -0.154  -0.984  1.00  0.00           C  
HETATM   19  C15 UNL     1      -5.618   1.081  -0.552  1.00  0.00           C  
HETATM   20  O5  UNL     1      -6.594   1.320  -1.519  1.00  0.00           O  
HETATM   21  C16 UNL     1      -4.646   2.211  -0.466  1.00  0.00           C  
HETATM   22  C17 UNL     1      -3.205   1.771  -0.762  1.00  0.00           C  
HETATM   23  C18 UNL     1      -2.786   0.667   0.184  1.00  0.00           C  
HETATM   24  C19 UNL     1      -2.946   1.219   1.592  1.00  0.00           C  
HETATM   25  C20 UNL     1      -1.355   0.300  -0.134  1.00  0.00           C  
HETATM   26  C21 UNL     1      -0.491   1.471   0.149  1.00  0.00           C  
HETATM   27  C22 UNL     1       0.991   1.185   0.135  1.00  0.00           C  
HETATM   28  C23 UNL     1       1.299  -0.060   0.869  1.00  0.00           C  
HETATM   29  C24 UNL     1       0.843   0.083   2.315  1.00  0.00           C  
HETATM   30  H1  UNL     1       4.520  -0.264  -1.804  1.00  0.00           H  
HETATM   31  H2  UNL     1       3.510   1.211  -1.795  1.00  0.00           H  
HETATM   32  H3  UNL     1       2.765  -0.465  -1.720  1.00  0.00           H  
HETATM   33  H4  UNL     1       3.591   1.332   0.406  1.00  0.00           H  
HETATM   34  H5  UNL     1       5.041  -0.104   1.742  1.00  0.00           H  
HETATM   35  H6  UNL     1       5.378  -1.168   0.361  1.00  0.00           H  
HETATM   36  H7  UNL     1       7.153   0.375   0.727  1.00  0.00           H  
HETATM   37  H8  UNL     1       6.118   1.800   0.752  1.00  0.00           H  
HETATM   38  H9  UNL     1       7.771   0.231  -2.625  1.00  0.00           H  
HETATM   39  H10 UNL     1       3.077  -0.605   1.935  1.00  0.00           H  
HETATM   40  H11 UNL     1       2.830  -2.169  -0.614  1.00  0.00           H  
HETATM   41  H12 UNL     1       3.300  -2.671   1.093  1.00  0.00           H  
HETATM   42  H13 UNL     1       0.942  -2.614   1.732  1.00  0.00           H  
HETATM   43  H14 UNL     1       1.020  -3.315   0.081  1.00  0.00           H  
HETATM   44  H15 UNL     1       0.618  -1.061  -0.898  1.00  0.00           H  
HETATM   45  H16 UNL     1      -1.000  -0.748   1.663  1.00  0.00           H  
HETATM   46  H17 UNL     1      -2.249  -2.561   1.203  1.00  0.00           H  
HETATM   47  H18 UNL     1      -1.645  -4.033  -0.174  1.00  0.00           H  
HETATM   48  H19 UNL     1      -3.780  -2.558  -0.451  1.00  0.00           H  
HETATM   49  H20 UNL     1      -2.641  -2.588  -2.217  1.00  0.00           H  
HETATM   50  H21 UNL     1      -4.228  -0.764   0.940  1.00  0.00           H  
HETATM   51  H22 UNL     1      -5.591  -1.004  -0.903  1.00  0.00           H  
HETATM   52  H23 UNL     1      -4.534  -0.106  -2.028  1.00  0.00           H  
HETATM   53  H24 UNL     1      -6.053   0.874   0.442  1.00  0.00           H  
HETATM   54  H25 UNL     1      -6.524   2.206  -1.929  1.00  0.00           H  
HETATM   55  H26 UNL     1      -4.620   2.637   0.559  1.00  0.00           H  
HETATM   56  H27 UNL     1      -4.858   3.014  -1.226  1.00  0.00           H  
HETATM   57  H28 UNL     1      -3.181   1.447  -1.821  1.00  0.00           H  
HETATM   58  H29 UNL     1      -2.615   2.714  -0.610  1.00  0.00           H  
HETATM   59  H30 UNL     1      -4.039   1.158   1.849  1.00  0.00           H  
HETATM   60  H31 UNL     1      -2.712   2.301   1.610  1.00  0.00           H  
HETATM   61  H32 UNL     1      -2.342   0.688   2.328  1.00  0.00           H  
HETATM   62  H33 UNL     1      -1.324   0.085  -1.227  1.00  0.00           H  
HETATM   63  H34 UNL     1      -0.772   2.031   1.059  1.00  0.00           H  
HETATM   64  H35 UNL     1      -0.655   2.216  -0.687  1.00  0.00           H  
HETATM   65  H36 UNL     1       1.466   2.073   0.646  1.00  0.00           H  
HETATM   66  H37 UNL     1       1.279   1.140  -0.930  1.00  0.00           H  
HETATM   67  H38 UNL     1       0.043   0.815   2.459  1.00  0.00           H  
HETATM   68  H39 UNL     1       1.740   0.516   2.852  1.00  0.00           H  
HETATM   69  H40 UNL     1       0.680  -0.896   2.803  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

HMDB0000760
     RDKit          3D
Hyocholic acid
 69 72  0  0  0  0  0  0  0  0999 V2000
    3.5952    0.2066   -1.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7187    0.2169    0.1202 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0954   -0.1016    0.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2106    0.7896    0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4892    0.9415   -1.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0911    1.9251   -1.8484 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2245   -0.0348   -1.8327 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6697   -0.5733    0.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6355   -2.0313    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1736   -2.3899    0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5017   -1.1717    0.1749 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9134   -0.9650    0.5703 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8350   -2.0985    0.2587 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2394   -3.1499   -0.4315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0474   -1.7044   -0.5608 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7443   -1.6385   -1.9060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7345   -0.4872   -0.0369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8616   -0.1537   -0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6176    1.0809   -0.5518 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5943    1.3204   -1.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6457    2.2108   -0.4658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2045    1.7710   -0.7620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7857    0.6673    0.1843 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9463    1.2194    1.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3545    0.3004   -0.1344 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4906    1.4712    0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9908    1.1845    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2992   -0.0598    0.8690 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8430    0.0830    2.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5196   -0.2640   -1.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5099    1.2114   -1.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7655   -0.4650   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5907    1.3320    0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0413   -0.1036    1.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3776   -1.1675    0.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1528    0.3746    0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1181    1.7997    0.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7713    0.2310   -2.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0772   -0.6049    1.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302   -2.1685   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2996   -2.6710    1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9418   -2.6140    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0197   -3.3154    0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -1.0614   -0.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0005   -0.7475    1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2487   -2.5611    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6454   -4.0335   -0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7801   -2.5576   -0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6415   -2.5878   -2.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2285   -0.7642    0.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5914   -1.0036   -0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5339   -0.1059   -2.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0529    0.8743    0.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5237    2.2056   -1.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6203    2.6366    0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8578    3.0141   -1.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1813    1.4468   -1.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6145    2.7138   -0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0390    1.1581    1.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7124    2.3009    1.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3421    0.6885    2.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235    0.0848   -1.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7716    2.0307    1.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6551    2.2164   -0.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4657    2.0731    0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2786    1.1400   -0.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0434    0.8147    2.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7405    0.5164    2.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6799   -0.8960    2.8029 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  1
 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  0
  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  1
 14 47  1  0
 15 48  1  6
 16 49  1  0
 17 50  1  1
 18 51  1  0
 18 52  1  0
 19 53  1  1
 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
Hyocholate	Generator
(4R)-4-[(1S,2R,5R,7R,8R,9S,10S,11S,15R)-5,8,9-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	HMDB
3a,6a,7a-Trihydroxy-5b-cholan-24-Oate	HMDB
3a,6a,7a-Trihydroxy-5b-cholan-24-Oic acid	HMDB
3a,6a,7a-Trihydroxy-5b-cholanate	HMDB
3a,6a,7a-Trihydroxy-5b-cholanic acid	HMDB
3a,6a,7a-Trihydroxy-5b-cholanoate	HMDB
3a,6a,7a-Trihydroxy-5b-cholanoic acid	HMDB
5b-Cholanic acid-3a,6a,7a-triol	HMDB
6a-Hydroxychenodeoxycholate	HMDB
6a-Hydroxychenodeoxycholic acid	HMDB
a-Hyocholate	HMDB
a-Hyocholic acid	HMDB
alpha-Hyocholate	HMDB
alpha-Hyocholic acid	HMDB
g-Muricholate	HMDB
g-Muricholic acid	HMDB
gamma-Muricholate	HMDB
gamma-Muricholic acid	HMDB
Iocholate	HMDB
Iocholic acid	HMDB
(4R)-4-[(1S,2R,5R,7R,8R,9S,10S,11S,15R)-5,8,9-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl]pentanoate	Generator

Chemical Formula

C₂₄H₄₀O₅

Average Molecular Weight

408.5714

Monoisotopic Molecular Weight

408.28757439

IUPAC Name

(4R)-4-[(1S,2R,5R,7R,8R,9S,10S,11S,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,8R,9S,10S,11S,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

547-75-1

SMILES

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

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-NNFRHCBVSA-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

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	0.018 mg/mL	Not Available
LogP	2.72	Extrapolated

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	206.001	30932474

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	46.86 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]+	193.98	31661259
DarkChem	[M-H]-	188.498	31661259
AllCCS	[M+H]+	203.609	32859911
AllCCS	[M-H]-	201.036	32859911
DeepCCS	[M-2H]-	224.951	30932474
DeepCCS	[M+Na]+	199.105	30932474
AllCCS	[M+H]+	203.6	32859911
AllCCS	[M+H-H2O]+	201.5	32859911
AllCCS	[M+NH4]+	205.5	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
Hyocholic acid	[H][C@@]12CCC([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)[C@H](O)[C@]2([H])C[C@H](O)CC[C@]12C	3718.3	Standard polar	33892256
Hyocholic acid	[H][C@@]12CCC([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)[C@H](O)[C@]2([H])C[C@H](O)CC[C@]12C	3476.8	Standard non polar	33892256
Hyocholic acid	[H][C@@]12CCC([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)[C@H](O)[C@]2([H])C[C@H](O)CC[C@]12C	3613.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hyocholic acid,1TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)C1CC[C@H]2[C@@H]3[C@H](O)[C@H](O)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3416.5	Semi standard non polar	33892256
Hyocholic acid,1TMS,isomer #2	C[C@H](CCC(=O)O)C1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)[C@H](O)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3370.3	Semi standard non polar	33892256
Hyocholic acid,1TMS,isomer #3	C[C@H](CCC(=O)O)C1CC[C@H]2[C@@H]3[C@H](O)[C@H](O[Si](C)(C)C)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3373.1	Semi standard non polar	33892256
Hyocholic acid,1TMS,isomer #4	C[C@H](CCC(=O)O)C1CC[C@H]2[C@@H]3[C@H](O)[C@H](O)[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3445.2	Semi standard non polar	33892256
Hyocholic acid,2TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)C1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)[C@H](O)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3327.4	Semi standard non polar	33892256
Hyocholic acid,2TMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C)C1CC[C@H]2[C@@H]3[C@H](O)[C@H](O[Si](C)(C)C)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3324.1	Semi standard non polar	33892256
Hyocholic acid,2TMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C)C1CC[C@H]2[C@@H]3[C@H](O)[C@H](O)[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3396.5	Semi standard non polar	33892256
Hyocholic acid,2TMS,isomer #4	C[C@H](CCC(=O)O)C1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3289.3	Semi standard non polar	33892256
Hyocholic acid,2TMS,isomer #5	C[C@H](CCC(=O)O)C1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)[C@H](O)[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3325.9	Semi standard non polar	33892256
Hyocholic acid,2TMS,isomer #6	C[C@H](CCC(=O)O)C1CC[C@H]2[C@@H]3[C@H](O)[C@H](O[Si](C)(C)C)[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3335.4	Semi standard non polar	33892256
Hyocholic acid,3TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)C1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3284.2	Semi standard non polar	33892256
Hyocholic acid,3TMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C)C1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)[C@H](O)[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3314.2	Semi standard non polar	33892256
Hyocholic acid,3TMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C)C1CC[C@H]2[C@@H]3[C@H](O)[C@H](O[Si](C)(C)C)[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3315.5	Semi standard non polar	33892256
Hyocholic acid,3TMS,isomer #4	C[C@H](CCC(=O)O)C1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3307.8	Semi standard non polar	33892256
Hyocholic acid,4TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)C1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3314.1	Semi standard non polar	33892256
Hyocholic acid,1TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C1CC[C@H]2[C@@H]3[C@H](O)[C@H](O)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3683.9	Semi standard non polar	33892256
Hyocholic acid,1TBDMS,isomer #2	C[C@H](CCC(=O)O)C1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3594.2	Semi standard non polar	33892256
Hyocholic acid,1TBDMS,isomer #3	C[C@H](CCC(=O)O)C1CC[C@H]2[C@@H]3[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3602.7	Semi standard non polar	33892256
Hyocholic acid,1TBDMS,isomer #4	C[C@H](CCC(=O)O)C1CC[C@H]2[C@@H]3[C@H](O)[C@H](O)[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3676.6	Semi standard non polar	33892256
Hyocholic acid,2TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3778.0	Semi standard non polar	33892256
Hyocholic acid,2TBDMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C1CC[C@H]2[C@@H]3[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3790.3	Semi standard non polar	33892256
Hyocholic acid,2TBDMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C1CC[C@H]2[C@@H]3[C@H](O)[C@H](O)[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3878.6	Semi standard non polar	33892256
Hyocholic acid,2TBDMS,isomer #4	C[C@H](CCC(=O)O)C1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3714.5	Semi standard non polar	33892256
Hyocholic acid,2TBDMS,isomer #5	C[C@H](CCC(=O)O)C1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3752.6	Semi standard non polar	33892256
Hyocholic acid,2TBDMS,isomer #6	C[C@H](CCC(=O)O)C1CC[C@H]2[C@@H]3[C@H](O)[C@H](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@]12C	3779.2	Semi standard non polar	33892256
Hyocholic acid,3TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3909.1	Semi standard non polar	33892256
Hyocholic acid,3TBDMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3952.5	Semi standard non polar	33892256
Hyocholic acid,3TBDMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C1CC[C@H]2[C@@H]3[C@H](O)[C@H](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@]12C	3964.9	Semi standard non polar	33892256
Hyocholic acid,3TBDMS,isomer #4	C[C@H](CCC(=O)O)C1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@H](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@]12C	3929.8	Semi standard non polar	33892256
Hyocholic acid,4TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)[C@H](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@]12C	4122.8	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 - Hyocholic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-0329000000-fed34af3d93baa3f7367	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic 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 - Hyocholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hyocholic acid GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyocholic acid 10V, Positive-QTOF	splash10-0596-0009200000-68022c747190b8d9159d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyocholic acid 20V, Positive-QTOF	splash10-00dm-0009000000-f33b26becb402995f0c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyocholic acid 40V, Positive-QTOF	splash10-003u-3409000000-c98554b075722b6c348b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyocholic acid 10V, Negative-QTOF	splash10-0a4i-0006900000-d69d03dcd69523fa0f48	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyocholic acid 20V, Negative-QTOF	splash10-0a4r-1009400000-2901e7db0545c5747619	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyocholic acid 40V, Negative-QTOF	splash10-0a4l-9006000000-c9f8bf273d05021457ac	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyocholic acid 10V, Negative-QTOF	splash10-0a4i-0001900000-68e3200734e1d0985f37	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyocholic acid 20V, Negative-QTOF	splash10-0a4r-0009800000-a11781ffcf06d8bb288c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyocholic acid 40V, Negative-QTOF	splash10-0a4j-3009300000-d354f18e540a94d7dfe1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyocholic acid 10V, Positive-QTOF	splash10-0ab9-0009600000-56beda528763ce5ae6df	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyocholic acid 20V, Positive-QTOF	splash10-059j-3449200000-98d256091462f2bbd882	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hyocholic acid 40V, Positive-QTOF	splash10-052u-4951000000-c203ad5efbf5e653aa09	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Gall Bladder
Intestine
Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected and Quantified	6.71 +/- 4.46 nmol/g dry feces	Not Specified	Not Specified	Normal	22664055	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	1.15 (0.20-2.31) umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details
Urine	Detected and Quantified	0.58 (0.15-1.36) umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Primary biliary cirrhosis
Batta AK, Arora R, Salen G, Tint GS, Eskreis D, Katz S: Characterization of serum and urinary bile acids in patients with primary biliary cirrhosis by gas-liquid chromatography-mass spectrometry: effect of ursodeoxycholic acid treatment. J Lipid Res. 1989 Dec;30(12):1953-62. [PubMed:2621422 ]

Associated OMIM IDs

114500 (Colorectal cancer)
109720 (Primary biliary cirrhosis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022229

KNApSAcK ID

Not Available

Chemspider ID

59651444

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hyocholic acid

METLIN ID

5728

PubChem Compound

131750324

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

HYOCHOL

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Iida, Takashi; Momose, Toshiaki; Tamura, Toshitake; Matsumoto, Taro; Chang, Frederic C.; Goto, Junichi; Nambara, Toshio. Potential bile acid metabolites. 14. Hyocholic and muricholic acid stereoisomers. Journal of Lipid Research (1989), 30(8), 1267-79.

Material Safety Data Sheet (MSDS)

Not Available

General References

Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
Kimura A, Mahara R, Inoue T, Nomura Y, Murai T, Kurosawa T, Tohma M, Noguchi K, Hoshiyama A, Fujisawa T, Kato H: Profile of urinary bile acids in infants and children: developmental pattern of excretion of unsaturated ketonic bile acids and 7beta-hydroxylated bile acids. Pediatr Res. 1999 Apr;45(4 Pt 1):603-9. [PubMed:10203155 ]
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 Hyocholic acid (HMDB0000760)

MOL for HMDB0000760 (Hyocholic acid)

3D MOL for HMDB0000760 (Hyocholic acid)

3D SDF for HMDB0000760 (Hyocholic acid)

3D-SDF for HMDB0000760 (Hyocholic acid)

PDB for HMDB0000760 (Hyocholic acid)

3D PDB for HMDB0000760 (Hyocholic acid)

SMILES for HMDB0000760 (Hyocholic acid)

INCHI for HMDB0000760 (Hyocholic acid)

Structure for HMDB0000760 (Hyocholic acid)

3D Structure for HMDB0000760 (Hyocholic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Transporters

References

References