Jump To Section:

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

2022-03-07 02:49:07 UTC

HMDB ID

HMDB0000917

Secondary Accession Numbers

HMDB00917

Metabolite Identification

Common Name

Ursocholic acid

Description

Ursocholic 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 ). Ursocholic acid is the 7 beta-hydroxyepimer of cholic acid. It induces a reduction of bile cholesterol saturation.

Structure

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

Untitled Document-3
  Mrv0541 02231218492D          

 33 36  0  0  0  0            999 V2000
   -2.4539   -2.3339    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4539   -1.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7395   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7395   -2.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250   -2.3339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3105   -2.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -2.3339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4040   -1.5089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1184   -1.0964    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9030   -1.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3880   -0.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9030   -0.0164    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1580    0.7682    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5746    1.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7881    2.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5850    2.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9650    0.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -0.2714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1184    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040    0.1411    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3105   -0.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105   -1.0964    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0250   -1.5089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0250   -0.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7986    3.1589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1684    1.7786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040    0.9661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -2.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1684   -2.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250   -3.1589    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105   -1.9214    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -0.6839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -1.9214    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
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  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
 12 11  1  1  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
 13 17  1  1  0  0  0
 12 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  1  0  0  0
 16 25  2  0  0  0  0
 16 26  1  0  0  0  0
 20 27  1  6  0  0  0
  7 28  1  1  0  0  0
  1 29  1  6  0  0  0
  5 30  1  1  0  0  0
 22 31  1  6  0  0  0
  8 32  1  1  0  0  0
  9 33  1  6  0  0  0
M  END

HMDB0000917
     RDKit          3D
Ursocholic acid
 69 72  0  0  0  0  0  0  0  0999 V2000
   -4.1465   -0.6340   -2.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9816   -0.8419   -0.6492 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8355    0.0278    0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6965    1.4949    0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6094    2.2449    0.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5578    3.5021    0.9384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4828    1.6286    1.8287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6232   -1.1726   -0.1739 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2319   -2.4839   -0.8818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8746   -2.1502   -1.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3424   -1.2205   -0.4978 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9218   -0.5172   -0.7950 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9456   -1.5234   -1.2298 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0133   -1.5231   -2.6264 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3158   -1.2141   -0.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4871    0.2786   -0.6817 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9220    0.6392   -0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4005    0.0693    0.8367 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6982   -1.2701    0.6695 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4123    0.2599    1.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3133    1.2170    1.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000    0.9559    0.3408 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2481    2.3231   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3487    0.1602    0.5150 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2591    0.9816    1.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0873    0.3402    1.1257 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0510   -0.7564    2.0168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5117   -0.2488   -0.2229 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4450    0.7342   -1.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9446   -1.2488   -2.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4524    0.4280   -2.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2168   -0.8913   -2.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5051   -1.8652   -0.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6812   -0.3043    1.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9282   -0.2090    0.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8524    1.8901   -0.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6687    1.7968    0.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4890    0.6223    1.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7537   -1.4877    0.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0419   -3.3033   -0.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9576   -2.7952   -1.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9811   -1.7515   -2.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2441   -3.0635   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2162   -1.7960    0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8696    0.2630   -1.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6336   -2.5657   -0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996   -0.8895   -2.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401   -1.7076    0.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0691   -1.6225   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1993    0.6449   -1.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5142    0.1169   -1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1321    1.7031   -0.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3854    0.5813    1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1802   -1.4762   -0.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0266   -0.7166    2.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9864    0.7009    2.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082    1.2177    2.4861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7685    2.2508    1.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5940    2.2591   -1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9203    3.0350    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2393    2.7352   -0.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5780   -0.6581    1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5327    1.1387    2.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1687    2.0073    0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7982    1.0388    1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1541   -0.4309    2.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3526    1.2745   -1.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0368    0.2727   -2.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6799    1.5044   -1.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  6
 28  8  1  0
 28 11  1  0
 24 12  1  0
 22 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  6
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  1
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  6
 13 46  1  1
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  6
 17 51  1  0
 17 52  1  0
 18 53  1  1
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 23 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  1
 25 63  1  0
 25 64  1  0
 26 65  1  1
 27 66  1  0
 29 67  1  0
 29 68  1  0
 29 69  1  0
M  END

Untitled Document-3
  Mrv0541 02231218492D          

 33 36  0  0  0  0            999 V2000
   -2.4539   -2.3339    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4539   -1.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7395   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7395   -2.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250   -2.3339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3105   -2.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -2.3339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4040   -1.5089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1184   -1.0964    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9030   -1.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3880   -0.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9030   -0.0164    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1580    0.7682    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5746    1.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7881    2.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5850    2.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9650    0.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -0.2714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1184    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040    0.1411    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3105   -0.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105   -1.0964    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0250   -1.5089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0250   -0.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7986    3.1589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1684    1.7786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040    0.9661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -2.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1684   -2.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250   -3.1589    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105   -1.9214    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -0.6839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -1.9214    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
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  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
 12 11  1  1  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
 13 17  1  1  0  0  0
 12 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  1  0  0  0
 16 25  2  0  0  0  0
 16 26  1  0  0  0  0
 20 27  1  6  0  0  0
  7 28  1  1  0  0  0
  1 29  1  6  0  0  0
  5 30  1  1  0  0  0
 22 31  1  6  0  0  0
  8 32  1  1  0  0  0
  9 33  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000917

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19+,20+,22+,23+,24-/m1/s1

> <INCHI_KEY>
BHQCQFFYRZLCQQ-UTLSPDKDSA-N

> <FORMULA>
C24H40O5

> <MOLECULAR_WEIGHT>
408.5714

> <EXACT_MASS>
408.28757439

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
47.04348310499775

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
2.482494456666666

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.2963399055959

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.475012423758966

> <JCHEM_PKA_STRONGEST_BASIC>
-0.15944265438213734

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
110.7893

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ursocholic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000917
     RDKit          3D
Ursocholic acid
 69 72  0  0  0  0  0  0  0  0999 V2000
   -4.1465   -0.6340   -2.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9816   -0.8419   -0.6492 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8355    0.0278    0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6965    1.4949    0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6094    2.2449    0.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5578    3.5021    0.9384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4828    1.6286    1.8287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6232   -1.1726   -0.1739 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2319   -2.4839   -0.8818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8746   -2.1502   -1.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3424   -1.2205   -0.4978 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9218   -0.5172   -0.7950 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9456   -1.5234   -1.2298 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0133   -1.5231   -2.6264 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3158   -1.2141   -0.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4871    0.2786   -0.6817 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9220    0.6392   -0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4005    0.0693    0.8367 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6982   -1.2701    0.6695 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4123    0.2599    1.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3133    1.2170    1.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000    0.9559    0.3408 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2481    2.3231   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3487    0.1602    0.5150 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2591    0.9816    1.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0873    0.3402    1.1257 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0510   -0.7564    2.0168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5117   -0.2488   -0.2229 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4450    0.7342   -1.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9446   -1.2488   -2.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4524    0.4280   -2.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2168   -0.8913   -2.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5051   -1.8652   -0.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6812   -0.3043    1.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9282   -0.2090    0.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8524    1.8901   -0.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6687    1.7968    0.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4890    0.6223    1.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7537   -1.4877    0.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0419   -3.3033   -0.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9576   -2.7952   -1.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9811   -1.7515   -2.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2441   -3.0635   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2162   -1.7960    0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8696    0.2630   -1.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6336   -2.5657   -0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996   -0.8895   -2.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401   -1.7076    0.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0691   -1.6225   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1993    0.6449   -1.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5142    0.1169   -1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1321    1.7031   -0.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3854    0.5813    1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1802   -1.4762   -0.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0266   -0.7166    2.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9864    0.7009    2.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082    1.2177    2.4861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7685    2.2508    1.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5940    2.2591   -1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9203    3.0350    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2393    2.7352   -0.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5780   -0.6581    1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5327    1.1387    2.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1687    2.0073    0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7982    1.0388    1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1541   -0.4309    2.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3526    1.2745   -1.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0368    0.2727   -2.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6799    1.5044   -1.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  6
 28  8  1  0
 28 11  1  0
 24 12  1  0
 22 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  6
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  1
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  6
 13 46  1  1
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  6
 17 51  1  0
 17 52  1  0
 18 53  1  1
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 23 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  1
 25 63  1  0
 25 64  1  0
 26 65  1  1
 27 66  1  0
 29 67  1  0
 29 68  1  0
 29 69  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-3                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.581  -4.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.581  -2.817   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.247  -2.047   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.247  -5.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.913  -4.357   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.580  -5.127   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.754  -4.357   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.754  -2.817   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.088  -2.047   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.552  -2.522   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.458  -1.277   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.552  -0.031   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.028   1.434   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.939   2.523   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.338   4.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.825   4.409   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.535   1.754   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.088  -0.507   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.088   1.033   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.754   0.263   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.580  -0.507   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.580  -2.047   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.913  -2.817   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.913  -1.277   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.224   5.897   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.914   3.320   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.754   1.803   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.088  -5.127   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -5.914  -5.127   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0      -1.913  -5.897   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.580  -3.587   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.754  -1.277   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.088  -3.587   0.000  0.00  0.00           H+0
CONECT    1    2    4   29                                                  
CONECT    2    1    3                                                       
CONECT    3    2   23                                                       
CONECT    4    1    5                                                       
CONECT    5    4    6   23   30                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   28                                                  
CONECT    8    7    9   22   32                                             
CONECT    9    8   10   18   33                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   25   26                                                  
CONECT   17   13                                                            
CONECT   18   12    9   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21    8   23   31                                             
CONECT   23   22    3    5   24                                             
CONECT   24   23                                                            
CONECT   25   16                                                            
CONECT   26   16                                                            
CONECT   27   20                                                            
CONECT   28    7                                                            
CONECT   29    1                                                            
CONECT   30    5                                                            
CONECT   31   22                                                            
CONECT   32    8                                                            
CONECT   33    9                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0000917
HETATM    1  C1  UNL     1      -4.147  -0.634  -2.129  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.982  -0.842  -0.649  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.835   0.028   0.194  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.696   1.495   0.072  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.609   2.245   0.977  1.00  0.00           C  
HETATM    6  O1  UNL     1      -5.558   3.502   0.938  1.00  0.00           O  
HETATM    7  O2  UNL     1      -6.483   1.629   1.829  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.623  -1.173  -0.174  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.232  -2.484  -0.882  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.875  -2.150  -1.524  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.342  -1.220  -0.498  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.922  -0.517  -0.795  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.946  -1.523  -1.230  1.00  0.00           C  
HETATM   14  O3  UNL     1       2.013  -1.523  -2.626  1.00  0.00           O  
HETATM   15  C12 UNL     1       3.316  -1.214  -0.706  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.487   0.279  -0.682  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.922   0.639  -0.479  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.401   0.069   0.837  1.00  0.00           C  
HETATM   19  O4  UNL     1       5.698  -1.270   0.669  1.00  0.00           O  
HETATM   20  C16 UNL     1       4.412   0.260   1.942  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.313   1.217   1.633  1.00  0.00           C  
HETATM   22  C18 UNL     1       2.600   0.956   0.341  1.00  0.00           C  
HETATM   23  C19 UNL     1       2.248   2.323  -0.247  1.00  0.00           C  
HETATM   24  C20 UNL     1       1.349   0.160   0.515  1.00  0.00           C  
HETATM   25  C21 UNL     1       0.259   0.982   1.100  1.00  0.00           C  
HETATM   26  C22 UNL     1      -1.087   0.340   1.126  1.00  0.00           C  
HETATM   27  O5  UNL     1      -1.051  -0.756   2.017  1.00  0.00           O  
HETATM   28  C23 UNL     1      -1.512  -0.249  -0.223  1.00  0.00           C  
HETATM   29  C24 UNL     1      -1.445   0.734  -1.342  1.00  0.00           C  
HETATM   30  H1  UNL     1      -4.945  -1.249  -2.597  1.00  0.00           H  
HETATM   31  H2  UNL     1      -4.452   0.428  -2.368  1.00  0.00           H  
HETATM   32  H3  UNL     1      -3.217  -0.891  -2.697  1.00  0.00           H  
HETATM   33  H4  UNL     1      -4.505  -1.865  -0.505  1.00  0.00           H  
HETATM   34  H5  UNL     1      -4.681  -0.304   1.260  1.00  0.00           H  
HETATM   35  H6  UNL     1      -5.928  -0.209   0.014  1.00  0.00           H  
HETATM   36  H7  UNL     1      -4.852   1.890  -0.950  1.00  0.00           H  
HETATM   37  H8  UNL     1      -3.669   1.797   0.345  1.00  0.00           H  
HETATM   38  H9  UNL     1      -6.489   0.622   1.903  1.00  0.00           H  
HETATM   39  H10 UNL     1      -2.754  -1.488   0.909  1.00  0.00           H  
HETATM   40  H11 UNL     1      -2.042  -3.303  -0.191  1.00  0.00           H  
HETATM   41  H12 UNL     1      -2.958  -2.795  -1.630  1.00  0.00           H  
HETATM   42  H13 UNL     1      -0.981  -1.752  -2.531  1.00  0.00           H  
HETATM   43  H14 UNL     1      -0.244  -3.064  -1.575  1.00  0.00           H  
HETATM   44  H15 UNL     1      -0.216  -1.796   0.444  1.00  0.00           H  
HETATM   45  H16 UNL     1       0.870   0.263  -1.570  1.00  0.00           H  
HETATM   46  H17 UNL     1       1.634  -2.566  -0.948  1.00  0.00           H  
HETATM   47  H18 UNL     1       2.700  -0.890  -2.960  1.00  0.00           H  
HETATM   48  H19 UNL     1       3.440  -1.708   0.254  1.00  0.00           H  
HETATM   49  H20 UNL     1       4.069  -1.622  -1.400  1.00  0.00           H  
HETATM   50  H21 UNL     1       3.199   0.645  -1.706  1.00  0.00           H  
HETATM   51  H22 UNL     1       5.514   0.117  -1.281  1.00  0.00           H  
HETATM   52  H23 UNL     1       5.132   1.703  -0.586  1.00  0.00           H  
HETATM   53  H24 UNL     1       6.385   0.581   1.047  1.00  0.00           H  
HETATM   54  H25 UNL     1       6.180  -1.476  -0.151  1.00  0.00           H  
HETATM   55  H26 UNL     1       4.027  -0.717   2.359  1.00  0.00           H  
HETATM   56  H27 UNL     1       4.986   0.701   2.810  1.00  0.00           H  
HETATM   57  H28 UNL     1       2.608   1.218   2.486  1.00  0.00           H  
HETATM   58  H29 UNL     1       3.768   2.251   1.634  1.00  0.00           H  
HETATM   59  H30 UNL     1       1.594   2.259  -1.114  1.00  0.00           H  
HETATM   60  H31 UNL     1       1.920   3.035   0.538  1.00  0.00           H  
HETATM   61  H32 UNL     1       3.239   2.735  -0.601  1.00  0.00           H  
HETATM   62  H33 UNL     1       1.578  -0.658   1.260  1.00  0.00           H  
HETATM   63  H34 UNL     1       0.533   1.139   2.188  1.00  0.00           H  
HETATM   64  H35 UNL     1       0.169   2.007   0.699  1.00  0.00           H  
HETATM   65  H36 UNL     1      -1.798   1.039   1.552  1.00  0.00           H  
HETATM   66  H37 UNL     1      -1.154  -0.431   2.961  1.00  0.00           H  
HETATM   67  H38 UNL     1      -2.353   1.274  -1.587  1.00  0.00           H  
HETATM   68  H39 UNL     1      -1.037   0.273  -2.288  1.00  0.00           H  
HETATM   69  H40 UNL     1      -0.680   1.504  -1.075  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   24   45
CONECT   13   14   15   46
CONECT   14   47
CONECT   15   16   48   49
CONECT   16   17   22   50
CONECT   17   18   51   52
CONECT   18   19   20   53
CONECT   19   54
CONECT   20   21   55   56
CONECT   21   22   57   58
CONECT   22   23   24
CONECT   23   59   60   61
CONECT   24   25   62
CONECT   25   26   63   64
CONECT   26   27   28   65
CONECT   27   66
CONECT   28   29
CONECT   29   67   68   69
END

HMDB0000917
     RDKit          3D
Ursocholic acid
 69 72  0  0  0  0  0  0  0  0999 V2000
   -4.1465   -0.6340   -2.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9816   -0.8419   -0.6492 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8355    0.0278    0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6965    1.4949    0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6094    2.2449    0.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5578    3.5021    0.9384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4828    1.6286    1.8287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6232   -1.1726   -0.1739 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2319   -2.4839   -0.8818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8746   -2.1502   -1.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3424   -1.2205   -0.4978 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9218   -0.5172   -0.7950 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9456   -1.5234   -1.2298 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0133   -1.5231   -2.6264 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3158   -1.2141   -0.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4871    0.2786   -0.6817 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9220    0.6392   -0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4005    0.0693    0.8367 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6982   -1.2701    0.6695 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4123    0.2599    1.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3133    1.2170    1.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000    0.9559    0.3408 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2481    2.3231   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3487    0.1602    0.5150 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2591    0.9816    1.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0873    0.3402    1.1257 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0510   -0.7564    2.0168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5117   -0.2488   -0.2229 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4450    0.7342   -1.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9446   -1.2488   -2.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4524    0.4280   -2.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2168   -0.8913   -2.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5051   -1.8652   -0.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6812   -0.3043    1.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9282   -0.2090    0.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8524    1.8901   -0.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6687    1.7968    0.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4890    0.6223    1.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7537   -1.4877    0.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0419   -3.3033   -0.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9576   -2.7952   -1.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9811   -1.7515   -2.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2441   -3.0635   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2162   -1.7960    0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8696    0.2630   -1.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6336   -2.5657   -0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996   -0.8895   -2.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401   -1.7076    0.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0691   -1.6225   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1993    0.6449   -1.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5142    0.1169   -1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1321    1.7031   -0.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3854    0.5813    1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1802   -1.4762   -0.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0266   -0.7166    2.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9864    0.7009    2.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082    1.2177    2.4861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7685    2.2508    1.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5940    2.2591   -1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9203    3.0350    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2393    2.7352   -0.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5780   -0.6581    1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5327    1.1387    2.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1687    2.0073    0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7982    1.0388    1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1541   -0.4309    2.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3526    1.2745   -1.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0368    0.2727   -2.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6799    1.5044   -1.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  6
 28  8  1  0
 28 11  1  0
 24 12  1  0
 22 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  6
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  1
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  6
 13 46  1  1
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  6
 17 51  1  0
 17 52  1  0
 18 53  1  1
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 23 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  1
 25 63  1  0
 25 64  1  0
 26 65  1  1
 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
(3alpha,5beta,7beta,12alpha)-3,7,12-Trihydroxycholan-24-Oic acid	ChEBI
3alpha,7beta,12alpha-Trihydroxy-5beta-cholan-24-Oic acid	ChEBI
3alpha,7beta,12alpha-Trihydroxy-5beta-cholanic acid	ChEBI
7-Epicholic acid	ChEBI
7beta-Hydroxyisocholic acid	Kegg
(3a,5b,7b,12a)-3,7,12-Trihydroxycholan-24-Oate	Generator
(3a,5b,7b,12a)-3,7,12-Trihydroxycholan-24-Oic acid	Generator
(3alpha,5beta,7beta,12alpha)-3,7,12-Trihydroxycholan-24-Oate	Generator
(3Α,5β,7β,12α)-3,7,12-trihydroxycholan-24-Oate	Generator
(3Α,5β,7β,12α)-3,7,12-trihydroxycholan-24-Oic acid	Generator
3a,7b,12a-Trihydroxy-5b-cholan-24-Oate	Generator
3a,7b,12a-Trihydroxy-5b-cholan-24-Oic acid	Generator
3alpha,7beta,12alpha-Trihydroxy-5beta-cholan-24-Oate	Generator
3Α,7β,12α-trihydroxy-5β-cholan-24-Oate	Generator
3Α,7β,12α-trihydroxy-5β-cholan-24-Oic acid	Generator
3a,7b,12a-Trihydroxy-5b-cholanate	Generator
3a,7b,12a-Trihydroxy-5b-cholanic acid	Generator
3alpha,7beta,12alpha-Trihydroxy-5beta-cholanate	Generator
3Α,7β,12α-trihydroxy-5β-cholanate	Generator
3Α,7β,12α-trihydroxy-5β-cholanic acid	Generator
7-Epicholate	Generator
7b-Hydroxyisocholate	Generator
7b-Hydroxyisocholic acid	Generator
7beta-Hydroxyisocholate	Generator
7Β-hydroxyisocholate	Generator
7Β-hydroxyisocholic acid	Generator
Ursocholate	Generator
3a,7b,12a-Trihydroxy-5b-cholanoate	HMDB
3a,7b,12a-Trihydroxy-5b-cholanoic acid	HMDB
3a,7b,12a-Trihydroxycholanate	HMDB
3a,7b,12a-Trihydroxycholanic acid	HMDB
3 alpha,7 beta,12 alpha-Trihydroxy-5 beta-cholan-24-Oic acid	HMDB

Chemical Formula

C₂₄H₄₀O₅

Average Molecular Weight

408.5714

Monoisotopic Molecular Weight

408.28757439

IUPAC Name

(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

Traditional Name

ursocholic acid

CAS Registry Number

2955-27-3

SMILES

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

InChI Identifier

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

InChI Key

BHQCQFFYRZLCQQ-UTLSPDKDSA-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
12-hydroxysteroid
7-hydroxysteroid
7-alpha-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

bile acid (CHEBI:81240 )
C24 bile acids, alcohols, and derivatives (LMST04010088 )

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Depression (PMID: 35445772)

Alzheimer's Disease (PMID: 30337151)

Cirrhosis (PMID: 1112456)
Jaundice (PMID: 1112456)
Chronic hepatitis (PMID: 1112456)
Primary biliary cirrhosis (HMDB: HMDB0000917)

Cancer

Colorectal cancer (PMID: 21724466)

Digestive system disorder

Gastrointestinal disorder

Chronic diarrhea (PMID: 19900947)

Disposition

Biological location

Cytoplasm (HMDB: HMDB0000917)
Cell membrane (HMDB: HMDB0000917)

Biofluid or Excreta

Blood (HMDB: HMDB0000917)
Urine (HMDB: HMDB0000917)

Tissue substructure

Hepatic tissue (HMDB: HMDB0000917)

Organ

Excreta

Biofluid or Excreta

Urine (PMID: 2621422)
Feces (PMID: 31643938)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 2621422)
Bile (PMID: 31643938)

Cellular substructure

Extracellular (HMDB: HMDB0000917)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000917)

Source

Endogenous

Endogenous (HMDB: HMDB0000917)

Animal

Animal (HMDB: HMDB0000917)

Exogenous

Food

Food (HMDB: HMDB0000917)

Animal origin

Poultry

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

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0000917)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0000917)

Cellular process

Cell signaling (HMDB: HMDB0000917)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0000917)

Role

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	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	205.097	30932474
[M-H]-	Not Available	205.097	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001887

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.074 g/L	ALOGPS
logP	2.26	ALOGPS
logP	2.48	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-0.16	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	110.79 m³·mol⁻¹	ChemAxon
Polarizability	47.04 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
AllCCS	[M+H]+	203.044	32859911
AllCCS	[M-H]-	200.947	32859911
DeepCCS	[M-2H]-	237.784	30932474
DeepCCS	[M+Na]+	211.558	30932474
AllCCS	[M+H]+	203.0	32859911
AllCCS	[M+H-H2O]+	201.0	32859911
AllCCS	[M+NH4]+	204.9	32859911
AllCCS	[M+Na]+	205.4	32859911
AllCCS	[M-H]-	200.9	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
Ursocholic acid	[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C	4216.7	Standard polar	33892256
Ursocholic acid	[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C	3464.1	Standard non polar	33892256
Ursocholic acid	[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C	3681.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ursocholic acid,1TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C	3395.4	Semi standard non polar	33892256
Ursocholic acid,1TMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C	3422.2	Semi standard non polar	33892256
Ursocholic acid,1TMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C	3367.0	Semi standard non polar	33892256
Ursocholic acid,1TMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C	3442.5	Semi standard non polar	33892256
Ursocholic acid,2TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C	3314.0	Semi standard non polar	33892256
Ursocholic acid,2TMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C	3385.4	Semi standard non polar	33892256
Ursocholic acid,2TMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C	3379.4	Semi standard non polar	33892256
Ursocholic acid,2TMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C	3337.1	Semi standard non polar	33892256
Ursocholic acid,2TMS,isomer #5	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C	3372.3	Semi standard non polar	33892256
Ursocholic acid,2TMS,isomer #6	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C	3336.2	Semi standard non polar	33892256
Ursocholic acid,3TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C	3321.6	Semi standard non polar	33892256
Ursocholic acid,3TMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C	3329.1	Semi standard non polar	33892256
Ursocholic acid,3TMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C	3343.2	Semi standard non polar	33892256
Ursocholic acid,3TMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C	3336.5	Semi standard non polar	33892256
Ursocholic acid,4TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C)[C@@]21C	3341.1	Semi standard non polar	33892256
Ursocholic acid,1TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C	3642.8	Semi standard non polar	33892256
Ursocholic acid,1TBDMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C	3636.4	Semi standard non polar	33892256
Ursocholic acid,1TBDMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C	3579.0	Semi standard non polar	33892256
Ursocholic acid,1TBDMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C	3656.8	Semi standard non polar	33892256
Ursocholic acid,2TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C	3753.0	Semi standard non polar	33892256
Ursocholic acid,2TBDMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C	3849.5	Semi standard non polar	33892256
Ursocholic acid,2TBDMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C	3838.8	Semi standard non polar	33892256
Ursocholic acid,2TBDMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C	3767.2	Semi standard non polar	33892256
Ursocholic acid,2TBDMS,isomer #5	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C	3798.6	Semi standard non polar	33892256
Ursocholic acid,2TBDMS,isomer #6	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C	3761.4	Semi standard non polar	33892256
Ursocholic acid,3TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O)[C@@]21C	3941.8	Semi standard non polar	33892256
Ursocholic 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]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C	3958.5	Semi standard non polar	33892256
Ursocholic acid,3TBDMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C	3986.6	Semi standard non polar	33892256
Ursocholic acid,3TBDMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C	3967.2	Semi standard non polar	33892256
Ursocholic 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]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C	4162.0	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 - Ursocholic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03ec-0439000000-abd2a5c162e23ea0d78f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (4 TMS) - 70eV, Positive	splash10-001i-1100049000-ae391322cbbc458fdb46	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursocholic 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursocholic acid 40V, Negative-QTOF	splash10-0a4i-1019800000-4a5ffc11cb3fa93e46cb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursocholic acid 20V, Negative-QTOF	splash10-0a4i-0000900000-7f097ee7b44073c18648	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursocholic acid 10V, Negative-QTOF	splash10-0a4i-0000900000-07966770f57ff86aa177	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursocholic acid 10V, Positive-QTOF	splash10-00dl-0009100000-915584a506714c470270	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursocholic acid 20V, Positive-QTOF	splash10-00dl-0009000000-f970a088fc3d9cdb8fe6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursocholic acid 40V, Positive-QTOF	splash10-017j-3109000000-bb054743c390ef266044	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursocholic acid 10V, Negative-QTOF	splash10-0a4i-0008900000-ed202aebd950e99a7852	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursocholic acid 20V, Negative-QTOF	splash10-0a4r-1009300000-db2a4b9107b891a8ef3a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursocholic acid 40V, Negative-QTOF	splash10-0a4i-9006000000-87df039839010127a1a0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursocholic acid 10V, Negative-QTOF	splash10-0a4i-0001900000-450d1e4d25aae2ed99f4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursocholic acid 20V, Negative-QTOF	splash10-0a4r-0005900000-630ea179fce67da6f208	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursocholic acid 40V, Negative-QTOF	splash10-0r09-0019200000-0754019de78fe2be314d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursocholic acid 10V, Positive-QTOF	splash10-0abc-0009400000-fe4f5c75dd7ef6e8d9ce	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursocholic acid 20V, Positive-QTOF	splash10-059l-3159100000-f0eff49c7e8da5d00c58	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursocholic acid 40V, Positive-QTOF	splash10-0aor-9640000000-28284141ad8f72ab8fe1	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
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
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.2 (0.2-11.7) uM	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details
Urine	Detected and Quantified	1.0 (0.13-2.7) umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details

Associated Disorders and Diseases

Disease References

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

109720 (Primary biliary cirrhosis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022316

KNApSAcK ID

Not Available

Chemspider ID

109088

KEGG Compound ID

C17644

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5871

PubChem Compound

122340

PDB ID

Not Available

ChEBI ID

81240

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Terada, Masaki; Sato, Manabu; Horie, Yoshiaki; Takatsu, Mitsumune; Minami, Junichi. Production of ursocholic acid. Jpn. Kokai Tokkyo Koho (1986), 9 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
Batta AK, Salen G, Abroon J: Ursocholic acid, a hydrophilic bile acid, fails to improve liver function parameters in primary biliary cirrhosis: comparison with ursodeoxycholic acid. Am J Gastroenterol. 1997 Jun;92(6):1035-7. [PubMed:9177526 ]
Lanzini A, Pigozzi G, Facchinetti D, Bettini L, Castellano M, Beschi M, Rossi A, Muiesan G: Effect of chronic ursocholic acid administration on bile lipid composition and bile acid pool size in gallstone patients. Scand J Gastroenterol. 1990 Jul;25(7):711-9. [PubMed:2396085 ]
Tint GS, Batta AK, Dayal B, Kovell N, Shefer S, Salen G: Metabolism of ursocholic acid in humans: conversion of ursocholic acid to deoxycholic acid. Hepatology. 1992 Apr;15(4):645-50. [PubMed:1551642 ]
Li H, Chen F, Shang Q, Pan L, Shneider BL, Chiang JY, Forman BM, Ananthanarayanan M, Tint GS, Salen G, Xu G: FXR-activating ligands inhibit rabbit ASBT expression via FXR-SHP-FTF cascade. Am J Physiol Gastrointest Liver Physiol. 2005 Jan;288(1):G60-6. [PubMed:15591588 ]
Loria P, Carulli N, Medici G, Menozzi D, Salvioli G, Bertolotti M, Montanari M: Effect of ursocholic acid on bile lipid secretion and composition. Gastroenterology. 1986 Apr;90(4):865-74. [PubMed:3949116 ]
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 Ursocholic acid (HMDB0000917)

MOL for HMDB0000917 (Ursocholic acid)

3D MOL for HMDB0000917 (Ursocholic acid)

3D SDF for HMDB0000917 (Ursocholic acid)

3D-SDF for HMDB0000917 (Ursocholic acid)

PDB for HMDB0000917 (Ursocholic acid)

3D PDB for HMDB0000917 (Ursocholic acid)

SMILES for HMDB0000917 (Ursocholic acid)

INCHI for HMDB0000917 (Ursocholic acid)

Structure for HMDB0000917 (Ursocholic acid)

3D Structure for HMDB0000917 (Ursocholic 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