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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-11-30 15:50:43 UTC

Update Date

2022-03-07 02:51:28 UTC

HMDB ID

HMDB0013192

Secondary Accession Numbers

HMDB13192

Metabolite Identification

Common Name

3a,7b,21-Trihydroxy-5b-cholanoic acid

Description

3a,7b,21-Trihydroxy-5b-cholanoic acid is a bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 21. 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 holesterol. 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 nterohepatic 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


  Mrv0541 02251208182D          

 30 33  0  0  1  0            999 V2000
   10.9027  -10.6803    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9027  -11.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1882  -10.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1882  -11.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4738  -10.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4738  -11.5053    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3317  -10.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3317  -11.5053    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.6172  -10.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6172  -11.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0462   -9.4428    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0462  -10.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3317   -9.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6172   -9.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8308   -9.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3157   -9.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8310  -10.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0858   -8.4032    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.8928   -8.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5338   -7.7901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4448   -8.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2518   -8.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8038   -9.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6108   -9.1149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5488  -10.0711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9027   -9.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1325   -8.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7593  -11.9178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0462  -11.9178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1477   -7.4471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  8  1  0  0  0  0
  1  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2  1  1  0  0  0  0
 13 11  1  0  0  0  0
  7 12  1  0  0  0  0
 14 13  1  0  0  0  0
  9  7  1  0  0  0  0
  9 14  1  0  0  0  0
 15 11  1  0  0  0  0
 12 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18 15  1  0  0  0  0
 19 18  1  0  0  0  0
 18 20  1  6  0  0  0
 21 19  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 23  2  0  0  0  0
  1 26  1  1  0  0  0
 11 27  1  1  0  0  0
  6 28  1  6  0  0  0
  8 29  1  1  0  0  0
 30 19  1  0  0  0  0
M  END

HMDB0013192
     RDKit          3D
3a,7b,21-Trihydroxy-5b-cholanoic acid
 70 73  0  0  0  0  0  0  0  0999 V2000
   -4.1116   -1.4124    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3415   -0.1559    0.3532 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9246    0.3459    1.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4366    0.3413    1.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8754    1.1557    0.2981 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9253    2.5044    0.7193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0057    1.0900   -0.9124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5434    0.9402   -0.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8146    0.7293   -1.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3542    0.3946   -1.7611 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9743   -0.1451   -3.0159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1916   -0.7307   -0.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8698   -0.5047    0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875    0.5264    1.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2975    0.6038    1.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9415   -0.5953    0.6121 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1450   -1.6295    1.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2350   -1.1462   -0.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924   -0.8012   -1.7772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5055   -0.9989   -1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427   -0.2281    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3926   -0.3997    1.1419 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9910    0.5003    2.1806 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7057    0.1765    0.6499 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5392    0.3355    1.8160 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5157   -0.8691   -0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8090   -0.3144   -0.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6373    0.8089   -1.5585 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6830    1.4170   -1.9330 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3754    1.1727   -1.9865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6014   -2.0916   -0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2226   -1.9681    0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1128   -1.2160   -0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6320    1.3846    1.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7308   -0.3468    2.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8613    0.8288    2.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8448   -0.6969    1.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9031    0.8230    0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8649    2.8231    0.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1276    2.0709   -1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3741    0.3320   -1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1935    1.8934   -0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3323   -0.0021   -2.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8653    1.7021   -2.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7661    1.2844   -1.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1873    0.6015   -3.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7124   -1.6129   -1.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9134   -1.5131    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6038    1.5336    1.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5119    0.4177    2.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7044    0.7241    2.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6255    1.5466    0.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3718   -1.0774    2.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1966   -2.1752    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556   -2.4226    1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3001   -2.2713   -0.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9403   -1.4352   -2.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0692    0.2994   -1.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6788   -2.0672   -1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1762   -0.4827   -1.9041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3613    0.8531   -0.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5892   -1.3989    1.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7602    0.8669    2.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6372    1.1359    0.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6315    1.2976    1.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8151   -1.6422    0.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9424   -1.4282   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4725   -0.0834    0.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3131   -1.1333   -1.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2684    1.5353   -2.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
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 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
  8  2  1  0
 18 12  1  0
 13  2  1  0
 21 16  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  6
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  1
 11 46  1  0
 12 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 17 53  1  0
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 17 55  1  0
 18 56  1  0
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 20 60  1  0
 21 61  1  0
 22 62  1  1
 23 63  1  0
 24 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 27 69  1  0
 30 70  1  0
M  END


  Mrv0541 02251208182D          

 30 33  0  0  1  0            999 V2000
   10.9027  -10.6803    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9027  -11.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1882  -10.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1882  -11.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4738  -10.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4738  -11.5053    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3317  -10.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3317  -11.5053    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.6172  -10.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6172  -11.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0462   -9.4428    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0462  -10.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3317   -9.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6172   -9.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8308   -9.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3157   -9.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8310  -10.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0858   -8.4032    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.8928   -8.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5338   -7.7901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4448   -8.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2518   -8.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8038   -9.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6108   -9.1149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5488  -10.0711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9027   -9.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1325   -8.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7593  -11.9178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0462  -11.9178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1477   -7.4471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  8  1  0  0  0  0
  1  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2  1  1  0  0  0  0
 13 11  1  0  0  0  0
  7 12  1  0  0  0  0
 14 13  1  0  0  0  0
  9  7  1  0  0  0  0
  9 14  1  0  0  0  0
 15 11  1  0  0  0  0
 12 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18 15  1  0  0  0  0
 19 18  1  0  0  0  0
 18 20  1  6  0  0  0
 21 19  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 23  2  0  0  0  0
  1 26  1  1  0  0  0
 11 27  1  1  0  0  0
  6 28  1  6  0  0  0
  8 29  1  1  0  0  0
 30 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013192

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@]12CCC3C(C1CCC2[C@H](O)C(O)CCC(O)=O)[C@@H](O)CC1C[C@H](O)CC[C@]31C

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O6/c1-23-9-7-14(25)11-13(23)12-19(27)21-15-3-4-17(24(15,2)10-8-16(21)23)22(30)18(26)5-6-20(28)29/h13-19,21-22,25-27,30H,3-12H2,1-2H3,(H,28,29)/t13?,14-,15?,16?,17?,18?,19+,21?,22+,23+,24+/m1/s1

> <INCHI_KEY>
JHBLUEHIRYMJOU-ZSFPCQDKSA-N

> <FORMULA>
C24H40O6

> <MOLECULAR_WEIGHT>
424.5708

> <EXACT_MASS>
424.282489012

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
48.454018318654036

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S)-5-[(2S,5R,9S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-4,5-dihydroxypentanoic acid

> <ALOGPS_LOGP>
1.46

> <JCHEM_LOGP>
1.487186688333334

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.758469873692757

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.479001653073449

> <JCHEM_PKA_STRONGEST_BASIC>
-0.535664089178311

> <JCHEM_POLAR_SURFACE_AREA>
118.22000000000001

> <JCHEM_REFRACTIVITY>
112.28019999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-5-[(2S,5R,9S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-4,5-dihydroxypentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013192
     RDKit          3D
3a,7b,21-Trihydroxy-5b-cholanoic acid
 70 73  0  0  0  0  0  0  0  0999 V2000
   -4.1116   -1.4124    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3415   -0.1559    0.3532 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9246    0.3459    1.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4366    0.3413    1.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8754    1.1557    0.2981 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9253    2.5044    0.7193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0057    1.0900   -0.9124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5434    0.9402   -0.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8146    0.7293   -1.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3542    0.3946   -1.7611 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9743   -0.1451   -3.0159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1916   -0.7307   -0.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8698   -0.5047    0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875    0.5264    1.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2975    0.6038    1.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9415   -0.5953    0.6121 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1450   -1.6295    1.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2350   -1.1462   -0.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924   -0.8012   -1.7772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5055   -0.9989   -1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427   -0.2281    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3926   -0.3997    1.1419 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9910    0.5003    2.1806 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7057    0.1765    0.6499 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5392    0.3355    1.8160 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5157   -0.8691   -0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8090   -0.3144   -0.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6373    0.8089   -1.5585 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6830    1.4170   -1.9330 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3754    1.1727   -1.9865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6014   -2.0916   -0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2226   -1.9681    0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1128   -1.2160   -0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6320    1.3846    1.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7308   -0.3468    2.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8613    0.8288    2.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8448   -0.6969    1.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9031    0.8230    0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8649    2.8231    0.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1276    2.0709   -1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3741    0.3320   -1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1935    1.8934   -0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3323   -0.0021   -2.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8653    1.7021   -2.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7661    1.2844   -1.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1873    0.6015   -3.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7124   -1.6129   -1.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9134   -1.5131    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6038    1.5336    1.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5119    0.4177    2.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7044    0.7241    2.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6255    1.5466    0.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3718   -1.0774    2.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1966   -2.1752    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556   -2.4226    1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3001   -2.2713   -0.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9403   -1.4352   -2.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0692    0.2994   -1.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6788   -2.0672   -1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1762   -0.4827   -1.9041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3613    0.8531   -0.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5892   -1.3989    1.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7602    0.8669    2.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6372    1.1359    0.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6315    1.2976    1.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8151   -1.6422    0.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9424   -1.4282   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4725   -0.0834    0.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3131   -1.1333   -1.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2684    1.5353   -2.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
  8  2  1  0
 18 12  1  0
 13  2  1  0
 21 16  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  6
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  1
 11 46  1  0
 12 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 17 53  1  0
 17 54  1  0
 17 55  1  0
 18 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 22 62  1  1
 23 63  1  0
 24 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 27 69  1  0
 30 70  1  0
M  END

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      20.352 -19.937   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.352 -21.477   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.018 -19.167   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.018 -22.247   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.684 -19.937   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.684 -21.477   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.019 -19.937   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.019 -21.477   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.685 -19.167   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.685 -22.247   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.353 -17.627   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.353 -19.167   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.019 -16.857   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.685 -17.627   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.817 -17.151   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.723 -18.397   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.818 -19.642   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.293 -15.686   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.800 -15.366   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      25.263 -14.542   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      28.830 -16.510   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      30.337 -16.190   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      31.367 -17.335   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      32.873 -17.014   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      30.891 -18.799   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      20.352 -18.397   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      24.514 -16.095   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.351 -22.247   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      24.353 -22.247   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      28.276 -13.901   0.000  0.00  0.00           O+0
CONECT    1    3    9    2   26                                             
CONECT    2    4   10    1                                                  
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5   28                                                  
CONECT    7    8   12    9                                                  
CONECT    8    7   10   29                                                  
CONECT    9    1    7   14                                                  
CONECT   10    8    2                                                       
CONECT   11   13   15   12   27                                             
CONECT   12    7   11   17                                                  
CONECT   13   11   14                                                       
CONECT   14   13    9                                                       
CONECT   15   11   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   12   16                                                       
CONECT   18   15   19   20                                                  
CONECT   19   18   21   30                                                  
CONECT   20   18                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    1                                                            
CONECT   27   11                                                            
CONECT   28    6                                                            
CONECT   29    8                                                            
CONECT   30   19                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0013192
HETATM    1  C1  UNL     1      -4.112  -1.412   0.016  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.341  -0.156   0.353  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.925   0.346   1.676  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.437   0.341   1.463  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.875   1.156   0.298  1.00  0.00           C  
HETATM    6  O1  UNL     1      -5.925   2.504   0.719  1.00  0.00           O  
HETATM    7  C6  UNL     1      -5.006   1.090  -0.912  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.543   0.940  -0.640  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.815   0.729  -1.918  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.354   0.395  -1.761  1.00  0.00           C  
HETATM   11  O2  UNL     1      -0.974  -0.145  -3.016  1.00  0.00           O  
HETATM   12  C10 UNL     1      -1.192  -0.731  -0.764  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.870  -0.505   0.544  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.187   0.526   1.370  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.297   0.604   1.211  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.941  -0.595   0.612  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.145  -1.629   1.697  1.00  0.00           C  
HETATM   18  C16 UNL     1       0.235  -1.146  -0.586  1.00  0.00           C  
HETATM   19  C17 UNL     1       1.092  -0.801  -1.777  1.00  0.00           C  
HETATM   20  C18 UNL     1       2.505  -0.999  -1.170  1.00  0.00           C  
HETATM   21  C19 UNL     1       2.343  -0.228   0.099  1.00  0.00           C  
HETATM   22  C20 UNL     1       3.393  -0.400   1.142  1.00  0.00           C  
HETATM   23  O3  UNL     1       2.991   0.500   2.181  1.00  0.00           O  
HETATM   24  C21 UNL     1       4.706   0.176   0.650  1.00  0.00           C  
HETATM   25  O4  UNL     1       5.539   0.335   1.816  1.00  0.00           O  
HETATM   26  C22 UNL     1       5.516  -0.869  -0.142  1.00  0.00           C  
HETATM   27  C23 UNL     1       6.809  -0.314  -0.642  1.00  0.00           C  
HETATM   28  C24 UNL     1       6.637   0.809  -1.559  1.00  0.00           C  
HETATM   29  O5  UNL     1       7.683   1.417  -1.933  1.00  0.00           O  
HETATM   30  O6  UNL     1       5.375   1.173  -1.986  1.00  0.00           O  
HETATM   31  H1  UNL     1      -3.601  -2.092  -0.662  1.00  0.00           H  
HETATM   32  H2  UNL     1      -4.223  -1.968   0.993  1.00  0.00           H  
HETATM   33  H3  UNL     1      -5.113  -1.216  -0.365  1.00  0.00           H  
HETATM   34  H4  UNL     1      -3.632   1.385   1.855  1.00  0.00           H  
HETATM   35  H5  UNL     1      -3.731  -0.347   2.505  1.00  0.00           H  
HETATM   36  H6  UNL     1      -5.861   0.829   2.386  1.00  0.00           H  
HETATM   37  H7  UNL     1      -5.845  -0.697   1.468  1.00  0.00           H  
HETATM   38  H8  UNL     1      -6.903   0.823   0.026  1.00  0.00           H  
HETATM   39  H9  UNL     1      -6.865   2.823   0.729  1.00  0.00           H  
HETATM   40  H10 UNL     1      -5.128   2.071  -1.461  1.00  0.00           H  
HETATM   41  H11 UNL     1      -5.374   0.332  -1.666  1.00  0.00           H  
HETATM   42  H12 UNL     1      -3.193   1.893  -0.179  1.00  0.00           H  
HETATM   43  H13 UNL     1      -3.332  -0.002  -2.589  1.00  0.00           H  
HETATM   44  H14 UNL     1      -2.865   1.702  -2.492  1.00  0.00           H  
HETATM   45  H15 UNL     1      -0.766   1.284  -1.503  1.00  0.00           H  
HETATM   46  H16 UNL     1      -1.187   0.602  -3.662  1.00  0.00           H  
HETATM   47  H17 UNL     1      -1.712  -1.613  -1.247  1.00  0.00           H  
HETATM   48  H18 UNL     1      -1.913  -1.513   1.054  1.00  0.00           H  
HETATM   49  H19 UNL     1      -1.604   1.534   1.074  1.00  0.00           H  
HETATM   50  H20 UNL     1      -1.512   0.418   2.445  1.00  0.00           H  
HETATM   51  H21 UNL     1       0.704   0.724   2.259  1.00  0.00           H  
HETATM   52  H22 UNL     1       0.625   1.547   0.687  1.00  0.00           H  
HETATM   53  H23 UNL     1       1.372  -1.077   2.630  1.00  0.00           H  
HETATM   54  H24 UNL     1       0.197  -2.175   1.941  1.00  0.00           H  
HETATM   55  H25 UNL     1       1.856  -2.423   1.433  1.00  0.00           H  
HETATM   56  H26 UNL     1       0.300  -2.271  -0.492  1.00  0.00           H  
HETATM   57  H27 UNL     1       0.940  -1.435  -2.645  1.00  0.00           H  
HETATM   58  H28 UNL     1       1.069   0.299  -1.998  1.00  0.00           H  
HETATM   59  H29 UNL     1       2.679  -2.067  -1.062  1.00  0.00           H  
HETATM   60  H30 UNL     1       3.176  -0.483  -1.904  1.00  0.00           H  
HETATM   61  H31 UNL     1       2.361   0.853  -0.190  1.00  0.00           H  
HETATM   62  H32 UNL     1       3.589  -1.399   1.503  1.00  0.00           H  
HETATM   63  H33 UNL     1       3.760   0.867   2.647  1.00  0.00           H  
HETATM   64  H34 UNL     1       4.637   1.136   0.180  1.00  0.00           H  
HETATM   65  H35 UNL     1       5.631   1.298   1.972  1.00  0.00           H  
HETATM   66  H36 UNL     1       5.815  -1.642   0.643  1.00  0.00           H  
HETATM   67  H37 UNL     1       4.942  -1.428  -0.861  1.00  0.00           H  
HETATM   68  H38 UNL     1       7.472  -0.083   0.221  1.00  0.00           H  
HETATM   69  H39 UNL     1       7.313  -1.133  -1.199  1.00  0.00           H  
HETATM   70  H40 UNL     1       5.268   1.535  -2.925  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    8   13
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6    7   38
CONECT    6   39
CONECT    7    8   40   41
CONECT    8    9   42
CONECT    9   10   43   44
CONECT   10   11   12   45
CONECT   11   46
CONECT   12   13   18   47
CONECT   13   14   48
CONECT   14   15   49   50
CONECT   15   16   51   52
CONECT   16   17   18   21
CONECT   17   53   54   55
CONECT   18   19   56
CONECT   19   20   57   58
CONECT   20   21   59   60
CONECT   21   22   61
CONECT   22   23   24   62
CONECT   23   63
CONECT   24   25   26   64
CONECT   25   65
CONECT   26   27   66   67
CONECT   27   28   68   69
CONECT   28   29   29   30
CONECT   30   70
END

HMDB0013192
     RDKit          3D
3a,7b,21-Trihydroxy-5b-cholanoic acid
 70 73  0  0  0  0  0  0  0  0999 V2000
   -4.1116   -1.4124    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3415   -0.1559    0.3532 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9246    0.3459    1.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4366    0.3413    1.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8754    1.1557    0.2981 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9253    2.5044    0.7193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0057    1.0900   -0.9124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5434    0.9402   -0.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8146    0.7293   -1.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3542    0.3946   -1.7611 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9743   -0.1451   -3.0159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1916   -0.7307   -0.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8698   -0.5047    0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875    0.5264    1.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2975    0.6038    1.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9415   -0.5953    0.6121 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1450   -1.6295    1.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2350   -1.1462   -0.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924   -0.8012   -1.7772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5055   -0.9989   -1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427   -0.2281    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3926   -0.3997    1.1419 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9910    0.5003    2.1806 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7057    0.1765    0.6499 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5392    0.3355    1.8160 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5157   -0.8691   -0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8090   -0.3144   -0.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6373    0.8089   -1.5585 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6830    1.4170   -1.9330 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3754    1.1727   -1.9865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6014   -2.0916   -0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2226   -1.9681    0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1128   -1.2160   -0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6320    1.3846    1.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7308   -0.3468    2.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8613    0.8288    2.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8448   -0.6969    1.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9031    0.8230    0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8649    2.8231    0.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1276    2.0709   -1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3741    0.3320   -1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1935    1.8934   -0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3323   -0.0021   -2.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8653    1.7021   -2.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7661    1.2844   -1.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1873    0.6015   -3.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7124   -1.6129   -1.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9134   -1.5131    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6038    1.5336    1.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5119    0.4177    2.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7044    0.7241    2.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6255    1.5466    0.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3718   -1.0774    2.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1966   -2.1752    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556   -2.4226    1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3001   -2.2713   -0.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9403   -1.4352   -2.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0692    0.2994   -1.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6788   -2.0672   -1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1762   -0.4827   -1.9041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3613    0.8531   -0.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5892   -1.3989    1.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7602    0.8669    2.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6372    1.1359    0.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6315    1.2976    1.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8151   -1.6422    0.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9424   -1.4282   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4725   -0.0834    0.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3131   -1.1333   -1.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2684    1.5353   -2.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
  8  2  1  0
 18 12  1  0
 13  2  1  0
 21 16  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  6
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  1
 11 46  1  0
 12 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 17 53  1  0
 17 54  1  0
 17 55  1  0
 18 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 22 62  1  1
 23 63  1  0
 24 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 27 69  1  0
 30 70  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3a,7b,21-Trihydroxy-5b-cholanoate	Generator
21-Hydroxyisocholate	HMDB
21-Hydroxyisocholic acid	HMDB
3a,7a,21-Trihydroxy-5b-cholanate	HMDB
3a,7a,21-Trihydroxy-5b-cholanic acid	HMDB
3a,7a,21-Trihydroxy-5b-cholanoate	HMDB
3a,7a,21-Trihydroxy-5b-cholanoic acid	HMDB
Lagocholate	HMDB
Lagocholic acid	HMDB
(5S)-5-[(2S,5R,9S,15S)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-4,5-dihydroxypentanoate	Generator

Chemical Formula

C₂₄H₄₀O₆

Average Molecular Weight

424.5708

Monoisotopic Molecular Weight

424.282489012

IUPAC Name

(5S)-5-[(2S,5R,9S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-4,5-dihydroxypentanoic acid

Traditional Name

(5S)-5-[(2S,5R,9S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-4,5-dihydroxypentanoic acid

CAS Registry Number

Not Available

SMILES

C[C@]12CCC3C(C1CCC2[C@H](O)C(O)CCC(O)=O)[C@@H](O)CC1C[C@H](O)CC[C@]31C

InChI Identifier

InChI=1S/C24H40O6/c1-23-9-7-14(25)11-13(23)12-19(27)21-15-3-4-17(24(15,2)10-8-16(21)23)22(30)18(26)5-6-20(28)29/h13-19,21-22,25-27,30H,3-12H2,1-2H3,(H,28,29)/t13?,14-,15?,16?,17?,18?,19+,21?,22+,23+,24+/m1/s1

InChI Key

JHBLUEHIRYMJOU-ZSFPCQDKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

20-hydroxysteroid
Androgen-skeleton
3-hydroxysteroid
7-hydroxysteroid
7-alpha-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
Medium-chain hydroxy acid
Medium-chain fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Depression (PMID: 35445772)

Alzheimer's Disease (PMID: 30337151)

Cancer

Colorectal cancer (PMID: 21724466)

Digestive system disorder

Gastrointestinal disorder

Chronic diarrhea (PMID: 19900947)

Disposition

Biological location

Cytoplasm (HMDB: HMDB0013192)
Cell membrane (HMDB: HMDB0013192)

Biofluid or Excreta

Urine (HMDB: HMDB0013192)

Tissue substructure

Hepatic tissue (HMDB: HMDB0013192)

Cellular substructure

Extracellular (HMDB: HMDB0013192)
Membrane (HMDB: HMDB0013192)

Non-excretory biofluid

Biofluid or Excreta

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

Excreta

Biofluid or Excreta

Feces (PMID: 31643938)
Urine (PMID: 1112456)

Organ

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013192)

Source

Endogenous

Endogenous (HMDB: HMDB0013192)

Animal

Animal (HMDB: HMDB0013192)

Exogenous

Food

Food (HMDB: HMDB0013192)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0013192)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0013192)

Cellular process

Cell signaling (HMDB: HMDB0013192)

System process

Reproduction (HMDB: HMDB0013192)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0013192)

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

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
logP	1.46	ALOGPS
logP	1.49	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-0.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	118.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	112.28 m³·mol⁻¹	ChemAxon
Polarizability	48.45 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]+	196.033	31661259
DarkChem	[M-H]-	188.037	31661259
DeepCCS	[M-2H]-	233.691	30932474
DeepCCS	[M+Na]+	208.719	30932474
AllCCS	[M+H]+	207.9	32859911
AllCCS	[M+H-H2O]+	205.9	32859911
AllCCS	[M+NH4]+	209.7	32859911
AllCCS	[M+Na]+	210.2	32859911
AllCCS	[M-H]-	204.7	32859911
AllCCS	[M+Na-2H]-	206.2	32859911
AllCCS	[M+HCOO]-	208.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3a,7b,21-Trihydroxy-5b-cholanoic acid	C[C@]12CCC3C(C1CCC2[C@H](O)C(O)CCC(O)=O)[C@@H](O)CC1C[C@H](O)CC[C@]31C	3384.1	Standard polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid	C[C@]12CCC3C(C1CCC2[C@H](O)C(O)CCC(O)=O)[C@@H](O)CC1C[C@H](O)CC[C@]31C	3438.5	Standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid	C[C@]12CCC3C(C1CCC2[C@H](O)C(O)CCC(O)=O)[C@@H](O)CC1C[C@H](O)CC[C@]31C	3841.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3a,7b,21-Trihydroxy-5b-cholanoic acid,1TMS,isomer #1	C[C@]12CC[C@@H](O)CC1C[C@H](O)C1C2CC[C@@]2(C)C1CCC2[C@H](O[Si](C)(C)C)C(O)CCC(=O)O	3739.4	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,1TMS,isomer #2	C[C@]12CC[C@@H](O)CC1C[C@H](O)C1C2CC[C@@]2(C)C1CCC2[C@H](O)C(CCC(=O)O)O[Si](C)(C)C	3758.7	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,1TMS,isomer #3	C[C@]12CC[C@@H](O)CC1C[C@H](O)C1C2CC[C@@]2(C)C1CCC2[C@H](O)C(O)CCC(=O)O[Si](C)(C)C	3736.2	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,1TMS,isomer #4	C[C@]12CC[C@@H](O)CC1C[C@H](O[Si](C)(C)C)C1C2CC[C@@]2(C)C1CCC2[C@H](O)C(O)CCC(=O)O	3780.6	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,1TMS,isomer #5	C[C@]12CC[C@@H](O[Si](C)(C)C)CC1C[C@H](O)C1C2CC[C@@]2(C)C1CCC2[C@H](O)C(O)CCC(=O)O	3772.2	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TMS,isomer #1	C[C@]12CC[C@@H](O[Si](C)(C)C)CC1C[C@H](O)C1C2CC[C@@]2(C)C1CCC2[C@H](O[Si](C)(C)C)C(O)CCC(=O)O	3703.3	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TMS,isomer #10	C[C@]12CC[C@@H](O[Si](C)(C)C)CC1C[C@H](O[Si](C)(C)C)C1C2CC[C@@]2(C)C1CCC2[C@H](O)C(O)CCC(=O)O	3760.1	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TMS,isomer #2	C[C@]12CC[C@@H](O)CC1C[C@H](O[Si](C)(C)C)C1C2CC[C@@]2(C)C1CCC2[C@H](O[Si](C)(C)C)C(O)CCC(=O)O	3640.1	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TMS,isomer #3	C[C@]12CC[C@@H](O)CC1C[C@H](O)C1C2CC[C@@]2(C)C1CCC2[C@H](O[Si](C)(C)C)C(CCC(=O)O)O[Si](C)(C)C	3745.9	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TMS,isomer #4	C[C@]12CC[C@@H](O)CC1C[C@H](O)C1C2CC[C@@]2(C)C1CCC2[C@H](O[Si](C)(C)C)C(O)CCC(=O)O[Si](C)(C)C	3660.1	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TMS,isomer #5	C[C@]12CC[C@@H](O[Si](C)(C)C)CC1C[C@H](O)C1C2CC[C@@]2(C)C1CCC2[C@H](O)C(CCC(=O)O)O[Si](C)(C)C	3741.1	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TMS,isomer #6	C[C@]12CC[C@@H](O)CC1C[C@H](O[Si](C)(C)C)C1C2CC[C@@]2(C)C1CCC2[C@H](O)C(CCC(=O)O)O[Si](C)(C)C	3681.1	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TMS,isomer #7	C[C@]12CC[C@@H](O)CC1C[C@H](O)C1C2CC[C@@]2(C)C1CCC2[C@H](O)C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3685.1	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TMS,isomer #8	C[C@]12CC[C@@H](O[Si](C)(C)C)CC1C[C@H](O)C1C2CC[C@@]2(C)C1CCC2[C@H](O)C(O)CCC(=O)O[Si](C)(C)C	3720.2	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TMS,isomer #9	C[C@]12CC[C@@H](O)CC1C[C@H](O[Si](C)(C)C)C1C2CC[C@@]2(C)C1CCC2[C@H](O)C(O)CCC(=O)O[Si](C)(C)C	3682.1	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TMS,isomer #1	C[C@]12CC[C@@H](O[Si](C)(C)C)CC1C[C@H](O[Si](C)(C)C)C1C2CC[C@@]2(C)C1CCC2[C@H](O[Si](C)(C)C)C(O)CCC(=O)O	3582.9	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TMS,isomer #10	C[C@]12CC[C@@H](O[Si](C)(C)C)CC1C[C@H](O[Si](C)(C)C)C1C2CC[C@@]2(C)C1CCC2[C@H](O)C(O)CCC(=O)O[Si](C)(C)C	3629.3	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TMS,isomer #2	C[C@]12CC[C@@H](O[Si](C)(C)C)CC1C[C@H](O)C1C2CC[C@@]2(C)C1CCC2[C@H](O[Si](C)(C)C)C(CCC(=O)O)O[Si](C)(C)C	3679.5	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TMS,isomer #3	C[C@]12CC[C@@H](O[Si](C)(C)C)CC1C[C@H](O)C1C2CC[C@@]2(C)C1CCC2[C@H](O[Si](C)(C)C)C(O)CCC(=O)O[Si](C)(C)C	3594.2	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TMS,isomer #4	C[C@]12CC[C@@H](O)CC1C[C@H](O[Si](C)(C)C)C1C2CC[C@@]2(C)C1CCC2[C@H](O[Si](C)(C)C)C(CCC(=O)O)O[Si](C)(C)C	3619.3	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TMS,isomer #5	C[C@]12CC[C@@H](O)CC1C[C@H](O[Si](C)(C)C)C1C2CC[C@@]2(C)C1CCC2[C@H](O[Si](C)(C)C)C(O)CCC(=O)O[Si](C)(C)C	3549.0	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TMS,isomer #6	C[C@]12CC[C@@H](O)CC1C[C@H](O)C1C2CC[C@@]2(C)C1CCC2[C@H](O[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3642.9	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TMS,isomer #7	C[C@]12CC[C@@H](O[Si](C)(C)C)CC1C[C@H](O[Si](C)(C)C)C1C2CC[C@@]2(C)C1CCC2[C@H](O)C(CCC(=O)O)O[Si](C)(C)C	3625.8	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TMS,isomer #8	C[C@]12CC[C@@H](O[Si](C)(C)C)CC1C[C@H](O)C1C2CC[C@@]2(C)C1CCC2[C@H](O)C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3616.3	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TMS,isomer #9	C[C@]12CC[C@@H](O)CC1C[C@H](O[Si](C)(C)C)C1C2CC[C@@]2(C)C1CCC2[C@H](O)C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3584.1	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,4TMS,isomer #1	C[C@]12CC[C@@H](O[Si](C)(C)C)CC1C[C@H](O[Si](C)(C)C)C1C2CC[C@@]2(C)C1CCC2[C@H](O[Si](C)(C)C)C(CCC(=O)O)O[Si](C)(C)C	3557.2	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,4TMS,isomer #2	C[C@]12CC[C@@H](O[Si](C)(C)C)CC1C[C@H](O[Si](C)(C)C)C1C2CC[C@@]2(C)C1CCC2[C@H](O[Si](C)(C)C)C(O)CCC(=O)O[Si](C)(C)C	3498.4	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,4TMS,isomer #3	C[C@]12CC[C@@H](O[Si](C)(C)C)CC1C[C@H](O)C1C2CC[C@@]2(C)C1CCC2[C@H](O[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3575.0	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,4TMS,isomer #4	C[C@]12CC[C@@H](O)CC1C[C@H](O[Si](C)(C)C)C1C2CC[C@@]2(C)C1CCC2[C@H](O[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3535.2	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,4TMS,isomer #5	C[C@]12CC[C@@H](O[Si](C)(C)C)CC1C[C@H](O[Si](C)(C)C)C1C2CC[C@@]2(C)C1CCC2[C@H](O)C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3529.8	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,5TMS,isomer #1	C[C@]12CC[C@@H](O[Si](C)(C)C)CC1C[C@H](O[Si](C)(C)C)C1C2CC[C@@]2(C)C1CCC2[C@H](O[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3471.6	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H](C(O)CCC(=O)O)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)CC1C[C@@H]3O	3974.6	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CCC(=O)O)[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)CC1C[C@@H]3O	4002.7	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CCC(O)[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)CC1C[C@@H]3O	3983.8	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1CC2C[C@H](O)CC[C@]2(C)C2CC[C@@]3(C)C(CCC3[C@H](O)C(O)CCC(=O)O)C21	3992.9	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@@]2(C)C(C[C@H](O)C3C2CC[C@@]2(C)C3CCC2[C@H](O)C(O)CCC(=O)O)C1	3993.8	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CCC(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)CC1C[C@@H]3O	4237.5	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@H]1CC2C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]2(C)C2CC[C@@]3(C)C(CCC3[C@H](O)C(O)CCC(=O)O)C21	4195.0	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC(O)[C@@H](O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)CC1C[C@@H]3O	4159.9	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H](C(O)CCC(=O)O)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@@H]3O	4188.7	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1CC2C[C@H](O)CC[C@]2(C)C2CC[C@@]3(C)C(CCC3[C@H](O[Si](C)(C)C(C)(C)C)C(O)CCC(=O)O)C21	4097.9	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)CCC(O[Si](C)(C)C(C)(C)C)[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)CC1C[C@@H]3O	4169.8	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(CCC(=O)O)[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@@H]3O	4213.1	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(CCC(=O)O)[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)CC1C[C@@H]3O[Si](C)(C)C(C)(C)C	4130.5	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)CCC(O)[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@@H]3O	4210.8	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC(=O)CCC(O)[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)CC1C[C@@H]3O[Si](C)(C)C(C)(C)C	4144.6	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)CC1C[C@@H]3O	4355.4	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)CCC(O)[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@@H]3O[Si](C)(C)C(C)(C)C	4299.3	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CCC(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@@H]3O	4417.2	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(CCC(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)CC1C[C@@H]3O[Si](C)(C)C(C)(C)C	4296.3	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CCC(O)[C@@H](O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@@H]3O	4318.9	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)CCC(O)[C@@H](O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)CC1C[C@@H]3O[Si](C)(C)C(C)(C)C	4227.3	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@H]1CC2C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]2(C)C2CC[C@@]3(C)C(CCC3[C@H](O[Si](C)(C)C(C)(C)C)C(O)CCC(=O)O)C21	4259.2	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)CCC(O[Si](C)(C)C(C)(C)C)[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@@H]3O	4317.6	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)CCC(O[Si](C)(C)C(C)(C)C)[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)CC1C[C@@H]3O[Si](C)(C)C(C)(C)C	4233.6	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC(CCC(=O)O)[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@@H]3O[Si](C)(C)C(C)(C)C	4277.5	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@@H]3O	4497.6	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)CC1C[C@@H]3O[Si](C)(C)C(C)(C)C	4389.7	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(CCC(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@@H]3O[Si](C)(C)C(C)(C)C	4451.4	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CCC(O)[C@@H](O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@@H]3O[Si](C)(C)C(C)(C)C	4389.9	Semi standard non polar	33892256
3a,7b,21-Trihydroxy-5b-cholanoic acid,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)CCC(O[Si](C)(C)C(C)(C)C)[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@@H]3O[Si](C)(C)C(C)(C)C	4393.9	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 - 3a,7b,21-Trihydroxy-5b-cholanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pb9-0459300000-254aff111622abadd039	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3a,7b,21-Trihydroxy-5b-cholanoic acid GC-MS (3 TMS) - 70eV, Positive	splash10-004i-1112169000-5395394ff6b105a34afb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3a,7b,21-Trihydroxy-5b-cholanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - 3a,7b,21-Trihydroxy-5b-cholanoic acid 10V, Positive-QTOF	splash10-052r-0009800000-8af77c3f05db01be9b67	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7b,21-Trihydroxy-5b-cholanoic acid 20V, Positive-QTOF	splash10-0abi-4039100000-e1c21f78d9d54ab82e24	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7b,21-Trihydroxy-5b-cholanoic acid 40V, Positive-QTOF	splash10-0fi0-4079000000-a52bdab7e9361b64e6d9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7b,21-Trihydroxy-5b-cholanoic acid 10V, Negative-QTOF	splash10-05fr-0002900000-9f9cf1f6feb9759b38c0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7b,21-Trihydroxy-5b-cholanoic acid 20V, Negative-QTOF	splash10-0ab9-4348900000-cd564da9feeda679e27c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7b,21-Trihydroxy-5b-cholanoic acid 40V, Negative-QTOF	splash10-052f-9157000000-dd12ac76965a1b2fa47a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7b,21-Trihydroxy-5b-cholanoic acid 10V, Negative-QTOF	splash10-0a4r-0106900000-e507acf721124b9610bc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7b,21-Trihydroxy-5b-cholanoic acid 20V, Negative-QTOF	splash10-03di-4009000000-b79dbd01554d1f17a391	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7b,21-Trihydroxy-5b-cholanoic acid 40V, Negative-QTOF	splash10-0079-9022200000-248cfe1010ee8c4c97e4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7b,21-Trihydroxy-5b-cholanoic acid 10V, Positive-QTOF	splash10-0550-1018900000-a1d1975cb859b07fb14c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7b,21-Trihydroxy-5b-cholanoic acid 20V, Positive-QTOF	splash10-00dr-4497200000-40a0c837670639f53763	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a,7b,21-Trihydroxy-5b-cholanoic acid 40V, Positive-QTOF	splash10-056u-8950000000-71a13901b74a96aea69b	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029325

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481646

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 3a,7b,21-Trihydroxy-5b-cholanoic acid (HMDB0013192)

MOL for HMDB0013192 (3a,7b,21-Trihydroxy-5b-cholanoic acid)

3D MOL for HMDB0013192 (3a,7b,21-Trihydroxy-5b-cholanoic acid)

3D SDF for HMDB0013192 (3a,7b,21-Trihydroxy-5b-cholanoic acid)

3D-SDF for HMDB0013192 (3a,7b,21-Trihydroxy-5b-cholanoic acid)

PDB for HMDB0013192 (3a,7b,21-Trihydroxy-5b-cholanoic acid)

3D PDB for HMDB0013192 (3a,7b,21-Trihydroxy-5b-cholanoic acid)

SMILES for HMDB0013192 (3a,7b,21-Trihydroxy-5b-cholanoic acid)

INCHI for HMDB0013192 (3a,7b,21-Trihydroxy-5b-cholanoic acid)

Structure for HMDB0013192 (3a,7b,21-Trihydroxy-5b-cholanoic acid)

3D Structure for HMDB0013192 (3a,7b,21-Trihydroxy-5b-cholanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra