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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-11-30 15:50:09 UTC

Update Date

2022-03-07 02:51:28 UTC

HMDB ID

HMDB0013158

Secondary Accession Numbers

HMDB13158

Metabolite Identification

Common Name

1b,3a,7b-Trihydroxy-5b-cholanoic acid

Description

1b,3a,7b-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 1, 3, and 7. 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 enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487 , 16037564 , 12576301 , 11907135 ).

Structure

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

  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  1  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
   10.1882   -9.4428    0.0000 O   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
  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
  3 28  1  1  0  0  0
  6 29  1  6  0  0  0
  8 30  1  1  0  0  0
M  END

HMDB0013158
     RDKit          3D
1b,3a,7b-Trihydroxy-5b-cholanoic acid
 70 73  0  0  0  0  0  0  0  0999 V2000
    1.7539   -1.6990   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2053   -0.3179    0.0783 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2941   -0.4245    1.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9780   -1.1990    1.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6520   -0.8172   -0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9944    0.4687   -0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3968    0.1480   -1.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1730    1.3149   -1.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7706    1.9287   -0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2006    0.7413    0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6559    0.4378    0.1001 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9199    0.1277   -1.2160 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3572   -0.3493    1.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7855   -0.6984    0.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8183    0.3383    0.8290 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7061    1.2758   -0.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4418    2.5144   -0.1591 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8959    0.8480   -1.5868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8089    1.2491   -1.6796 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0828    0.5539   -2.8306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0927    1.5779   -0.8912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8536    0.2723   -0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2242    0.4896   -0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3182    0.5352    1.1417 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5441    1.8235    1.6539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1221   -0.0739    1.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7485   -1.2808    1.0470 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0081   -1.9020    0.7833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1146   -0.8821   -0.2955 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5149   -2.0964   -1.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7670   -2.2274    0.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0071   -2.3228   -0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7367   -1.7618   -0.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151   -1.0064    2.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1390    0.5493    1.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5975   -0.9604    1.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -2.2810    1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2300   -1.5767   -0.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9093    1.1489    0.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3816   -0.7072   -1.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6214    2.0100   -2.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083    0.8869   -2.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6927    2.4824   -0.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0981    2.6074    0.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1371    1.0417    1.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1240    1.4972    0.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5893   -0.5492   -1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8474   -1.3294    1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2720    0.2442    2.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8177   -1.3649    0.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1460   -1.4173    1.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8471    0.9353    1.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8249   -0.2156    0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9143   -0.1261   -1.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3479    2.2088   -1.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4642    0.8353   -3.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7030    2.3081   -1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7801    1.9162    0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0127    0.0802   -1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5972    1.4563   -0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9206   -0.2877   -0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2060   -0.0652    1.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5374    1.9989    1.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4780   -0.4339    2.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3349    0.6522    2.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1963   -2.0595    1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4330   -1.9918    1.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2670   -1.8617   -2.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9310   -2.9472   -0.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5876   -2.2706   -1.0984 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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  6 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  6
  7  2  1  0
 29 22  1  0
 10  2  1  0
 29  5  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  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  6
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 18 54  1  0
 19 55  1  6
 20 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  6
 25 63  1  0
 26 64  1  0
 26 65  1  0
 27 66  1  1
 28 67  1  0
 30 68  1  0
 30 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  1  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
   10.1882   -9.4428    0.0000 O   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
  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
  3 28  1  1  0  0  0
  6 29  1  6  0  0  0
  8 30  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0013158

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O6/c1-23-9-8-17-22(16(23)7-6-15(23)18(26)4-3-5-21(29)30)19(27)11-13-10-14(25)12-20(28)24(13,17)2/h13-20,22,25-28H,3-12H2,1-2H3,(H,29,30)/t13?,14-,15?,16?,17?,18+,19-,20+,22?,23+,24-/m0/s1

> <INCHI_KEY>
TVLHFFLEOSSHFT-QVLZICSDSA-N

> <FORMULA>
C24H40O6

> <MOLECULAR_WEIGHT>
424.5708

> <EXACT_MASS>
424.282489012

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
48.688094436865164

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R)-5-hydroxy-5-[(2S,3R,5S,9S,15S)-3,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.258485222333334

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.503984784746944

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.614626553395153

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3042595111468859

> <JCHEM_POLAR_SURFACE_AREA>
118.22000000000001

> <JCHEM_REFRACTIVITY>
112.39059999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-5-hydroxy-5-[(2S,3R,5S,9S,15S)-3,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013158
     RDKit          3D
1b,3a,7b-Trihydroxy-5b-cholanoic acid
 70 73  0  0  0  0  0  0  0  0999 V2000
    1.7539   -1.6990   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2053   -0.3179    0.0783 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2941   -0.4245    1.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9780   -1.1990    1.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6520   -0.8172   -0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9944    0.4687   -0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3968    0.1480   -1.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1730    1.3149   -1.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7706    1.9287   -0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2006    0.7413    0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6559    0.4378    0.1001 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9199    0.1277   -1.2160 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3572   -0.3493    1.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7855   -0.6984    0.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8183    0.3383    0.8290 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7061    1.2758   -0.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4418    2.5144   -0.1591 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8959    0.8480   -1.5868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8089    1.2491   -1.6796 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0828    0.5539   -2.8306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0927    1.5779   -0.8912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8536    0.2723   -0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2242    0.4896   -0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3182    0.5352    1.1417 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5441    1.8235    1.6539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1221   -0.0739    1.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7485   -1.2808    1.0470 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0081   -1.9020    0.7833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1146   -0.8821   -0.2955 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5149   -2.0964   -1.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7670   -2.2274    0.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0071   -2.3228   -0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7367   -1.7618   -0.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151   -1.0064    2.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1390    0.5493    1.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5975   -0.9604    1.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -2.2810    1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2300   -1.5767   -0.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9093    1.1489    0.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3816   -0.7072   -1.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6214    2.0100   -2.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083    0.8869   -2.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6927    2.4824   -0.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0981    2.6074    0.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1371    1.0417    1.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1240    1.4972    0.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5893   -0.5492   -1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8474   -1.3294    1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2720    0.2442    2.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8177   -1.3649    0.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1460   -1.4173    1.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8471    0.9353    1.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8249   -0.2156    0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9143   -0.1261   -1.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3479    2.2088   -1.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4642    0.8353   -3.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7030    2.3081   -1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7801    1.9162    0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0127    0.0802   -1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5972    1.4563   -0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9206   -0.2877   -0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2060   -0.0652    1.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5374    1.9989    1.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4780   -0.4339    2.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3349    0.6522    2.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1963   -2.0595    1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4330   -1.9918    1.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2670   -1.8617   -2.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9310   -2.9472   -0.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5876   -2.2706   -1.0984 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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  6 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  6
  7  2  1  0
 29 22  1  0
 10  2  1  0
 29  5  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  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  6
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 18 54  1  0
 19 55  1  6
 20 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  6
 25 63  1  0
 26 64  1  0
 26 65  1  0
 27 66  1  1
 28 67  1  0
 30 68  1  0
 30 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      19.018 -17.627   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      16.351 -22.247   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      24.353 -22.247   0.000  0.00  0.00           O+0
CONECT    1    3    9    2   26                                             
CONECT    2    4   10    1                                                  
CONECT    3    1    5   28                                                  
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5   29                                                  
CONECT    7    8   12    9                                                  
CONECT    8    7   10   30                                                  
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                                                       
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    3                                                            
CONECT   29    6                                                            
CONECT   30    8                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0013158
HETATM    1  C1  UNL     1       1.754  -1.699  -0.148  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.205  -0.318   0.078  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.294  -0.425   1.287  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.978  -1.199   1.045  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.652  -0.817  -0.254  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.994   0.469  -0.674  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.397   0.148  -1.141  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.173   1.315  -1.661  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.771   1.929  -0.443  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.201   0.741   0.387  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.656   0.438   0.100  1.00  0.00           C  
HETATM   12  O1  UNL     1       3.920   0.128  -1.216  1.00  0.00           O  
HETATM   13  C12 UNL     1       4.357  -0.349   1.138  1.00  0.00           C  
HETATM   14  C13 UNL     1       5.785  -0.698   0.925  1.00  0.00           C  
HETATM   15  C14 UNL     1       6.818   0.338   0.829  1.00  0.00           C  
HETATM   16  C15 UNL     1       6.706   1.276  -0.267  1.00  0.00           C  
HETATM   17  O2  UNL     1       6.442   2.514  -0.159  1.00  0.00           O  
HETATM   18  O3  UNL     1       6.896   0.848  -1.587  1.00  0.00           O  
HETATM   19  C16 UNL     1      -1.809   1.249  -1.680  1.00  0.00           C  
HETATM   20  O4  UNL     1      -2.083   0.554  -2.831  1.00  0.00           O  
HETATM   21  C17 UNL     1      -3.093   1.578  -0.891  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.854   0.272  -0.905  1.00  0.00           C  
HETATM   23  C19 UNL     1      -5.224   0.490  -0.335  1.00  0.00           C  
HETATM   24  C20 UNL     1      -5.318   0.535   1.142  1.00  0.00           C  
HETATM   25  O5  UNL     1      -5.544   1.824   1.654  1.00  0.00           O  
HETATM   26  C21 UNL     1      -4.122  -0.074   1.852  1.00  0.00           C  
HETATM   27  C22 UNL     1      -3.748  -1.281   1.047  1.00  0.00           C  
HETATM   28  O6  UNL     1      -5.008  -1.902   0.783  1.00  0.00           O  
HETATM   29  C23 UNL     1      -3.115  -0.882  -0.295  1.00  0.00           C  
HETATM   30  C24 UNL     1      -3.515  -2.096  -1.179  1.00  0.00           C  
HETATM   31  H1  UNL     1       1.767  -2.227   0.824  1.00  0.00           H  
HETATM   32  H2  UNL     1       1.007  -2.323  -0.748  1.00  0.00           H  
HETATM   33  H3  UNL     1       2.737  -1.762  -0.600  1.00  0.00           H  
HETATM   34  H4  UNL     1       0.915  -1.006   2.042  1.00  0.00           H  
HETATM   35  H5  UNL     1       0.139   0.549   1.800  1.00  0.00           H  
HETATM   36  H6  UNL     1      -1.597  -0.960   1.945  1.00  0.00           H  
HETATM   37  H7  UNL     1      -0.671  -2.281   1.060  1.00  0.00           H  
HETATM   38  H8  UNL     1      -1.230  -1.577  -0.991  1.00  0.00           H  
HETATM   39  H9  UNL     1      -0.909   1.149   0.199  1.00  0.00           H  
HETATM   40  H10 UNL     1       0.382  -0.707  -1.848  1.00  0.00           H  
HETATM   41  H11 UNL     1       0.621   2.010  -2.300  1.00  0.00           H  
HETATM   42  H12 UNL     1       2.008   0.887  -2.289  1.00  0.00           H  
HETATM   43  H13 UNL     1       2.693   2.482  -0.766  1.00  0.00           H  
HETATM   44  H14 UNL     1       1.098   2.607   0.100  1.00  0.00           H  
HETATM   45  H15 UNL     1       2.137   1.042   1.484  1.00  0.00           H  
HETATM   46  H16 UNL     1       4.124   1.497   0.204  1.00  0.00           H  
HETATM   47  H17 UNL     1       4.589  -0.549  -1.384  1.00  0.00           H  
HETATM   48  H18 UNL     1       3.847  -1.329   1.410  1.00  0.00           H  
HETATM   49  H19 UNL     1       4.272   0.244   2.117  1.00  0.00           H  
HETATM   50  H20 UNL     1       5.818  -1.365   0.008  1.00  0.00           H  
HETATM   51  H21 UNL     1       6.146  -1.417   1.744  1.00  0.00           H  
HETATM   52  H22 UNL     1       6.847   0.935   1.800  1.00  0.00           H  
HETATM   53  H23 UNL     1       7.825  -0.216   0.803  1.00  0.00           H  
HETATM   54  H24 UNL     1       6.914  -0.126  -1.790  1.00  0.00           H  
HETATM   55  H25 UNL     1      -1.348   2.209  -1.886  1.00  0.00           H  
HETATM   56  H26 UNL     1      -1.464   0.835  -3.576  1.00  0.00           H  
HETATM   57  H27 UNL     1      -3.703   2.308  -1.446  1.00  0.00           H  
HETATM   58  H28 UNL     1      -2.780   1.916   0.089  1.00  0.00           H  
HETATM   59  H29 UNL     1      -4.013   0.080  -1.993  1.00  0.00           H  
HETATM   60  H30 UNL     1      -5.597   1.456  -0.741  1.00  0.00           H  
HETATM   61  H31 UNL     1      -5.921  -0.288  -0.768  1.00  0.00           H  
HETATM   62  H32 UNL     1      -6.206  -0.065   1.457  1.00  0.00           H  
HETATM   63  H33 UNL     1      -6.537   1.999   1.721  1.00  0.00           H  
HETATM   64  H34 UNL     1      -4.478  -0.434   2.837  1.00  0.00           H  
HETATM   65  H35 UNL     1      -3.335   0.652   2.046  1.00  0.00           H  
HETATM   66  H36 UNL     1      -3.196  -2.060   1.560  1.00  0.00           H  
HETATM   67  H37 UNL     1      -5.433  -1.992   1.659  1.00  0.00           H  
HETATM   68  H38 UNL     1      -3.267  -1.862  -2.233  1.00  0.00           H  
HETATM   69  H39 UNL     1      -2.931  -2.947  -0.784  1.00  0.00           H  
HETATM   70  H40 UNL     1      -4.588  -2.271  -1.098  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    7   10
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6   29   38
CONECT    6    7   19   39
CONECT    7    8   40
CONECT    8    9   41   42
CONECT    9   10   43   44
CONECT   10   11   45
CONECT   11   12   13   46
CONECT   12   47
CONECT   13   14   48   49
CONECT   14   15   50   51
CONECT   15   16   52   53
CONECT   16   17   17   18
CONECT   18   54
CONECT   19   20   21   55
CONECT   20   56
CONECT   21   22   57   58
CONECT   22   23   29   59
CONECT   23   24   60   61
CONECT   24   25   26   62
CONECT   25   63
CONECT   26   27   64   65
CONECT   27   28   29   66
CONECT   28   67
CONECT   29   30
CONECT   30   68   69   70
END

HMDB0013158
     RDKit          3D
1b,3a,7b-Trihydroxy-5b-cholanoic acid
 70 73  0  0  0  0  0  0  0  0999 V2000
    1.7539   -1.6990   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2053   -0.3179    0.0783 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2941   -0.4245    1.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9780   -1.1990    1.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6520   -0.8172   -0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9944    0.4687   -0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3968    0.1480   -1.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1730    1.3149   -1.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7706    1.9287   -0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2006    0.7413    0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6559    0.4378    0.1001 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9199    0.1277   -1.2160 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3572   -0.3493    1.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7855   -0.6984    0.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8183    0.3383    0.8290 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7061    1.2758   -0.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4418    2.5144   -0.1591 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8959    0.8480   -1.5868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8089    1.2491   -1.6796 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0828    0.5539   -2.8306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0927    1.5779   -0.8912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8536    0.2723   -0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2242    0.4896   -0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3182    0.5352    1.1417 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5441    1.8235    1.6539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1221   -0.0739    1.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7485   -1.2808    1.0470 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0081   -1.9020    0.7833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1146   -0.8821   -0.2955 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5149   -2.0964   -1.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7670   -2.2274    0.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0071   -2.3228   -0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7367   -1.7618   -0.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151   -1.0064    2.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1390    0.5493    1.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5975   -0.9604    1.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -2.2810    1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2300   -1.5767   -0.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9093    1.1489    0.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3816   -0.7072   -1.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6214    2.0100   -2.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083    0.8869   -2.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6927    2.4824   -0.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0981    2.6074    0.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1371    1.0417    1.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1240    1.4972    0.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5893   -0.5492   -1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8474   -1.3294    1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2720    0.2442    2.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8177   -1.3649    0.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1460   -1.4173    1.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8471    0.9353    1.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8249   -0.2156    0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9143   -0.1261   -1.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3479    2.2088   -1.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4642    0.8353   -3.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7030    2.3081   -1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7801    1.9162    0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0127    0.0802   -1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5972    1.4563   -0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9206   -0.2877   -0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2060   -0.0652    1.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5374    1.9989    1.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4780   -0.4339    2.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3349    0.6522    2.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1963   -2.0595    1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4330   -1.9918    1.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2670   -1.8617   -2.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9310   -2.9472   -0.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5876   -2.2706   -1.0984 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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  6 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  6
  7  2  1  0
 29 22  1  0
 10  2  1  0
 29  5  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  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  6
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 18 54  1  0
 19 55  1  6
 20 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  6
 25 63  1  0
 26 64  1  0
 26 65  1  0
 27 66  1  1
 28 67  1  0
 30 68  1  0
 30 69  1  0
 30 70  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1b,3a,7b-Trihydroxy-5b-cholanoate	Generator
1b,3a,7b-Trihydroxy-5b-cholanate	HMDB
1b,3a,7b-Trihydroxy-5b-cholanic acid	HMDB
7b-Hydroxyisocholate	HMDB
7b-Hydroxyisocholic acid	HMDB
Lagocholate	HMDB
Lagocholic acid	HMDB
(5R)-5-Hydroxy-5-[(2S,3R,5S,9S,15S)-3,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	Generator

Chemical Formula

C₂₄H₄₀O₆

Average Molecular Weight

424.5708

Monoisotopic Molecular Weight

424.282489012

IUPAC Name

(5R)-5-hydroxy-5-[(2S,3R,5S,9S,15S)-3,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

Traditional Name

(5R)-5-hydroxy-5-[(2S,3R,5S,9S,15S)-3,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H40O6/c1-23-9-8-17-22(16(23)7-6-15(23)18(26)4-3-5-21(29)30)19(27)11-13-10-14(25)12-20(28)24(13,17)2/h13-20,22,25-28H,3-12H2,1-2H3,(H,29,30)/t13?,14-,15?,16?,17?,18+,19-,20+,22?,23+,24-/m0/s1

InChI Key

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Disposition

Biological location

Cellular substructure

Non-excretory biofluid

Biofluid or Excreta

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

Excreta

Biofluid or Excreta

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

Organ

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0013158)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013158)

Source

Endogenous

Endogenous (HMDB: HMDB0013158)

Animal

Animal (HMDB: HMDB0013158)

Exogenous

Food

Food (HMDB: HMDB0013158)

Exogenous (HMDB: HMDB0013158)

Process

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	0.24 g/L	ALOGPS
logP	1.42	ALOGPS
logP	1.26	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.61	ChemAxon
pKa (Strongest Basic)	-0.3	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	112.39 m³·mol⁻¹	ChemAxon
Polarizability	48.69 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]+	196.586	31661259
DarkChem	[M-H]-	191.057	31661259
DeepCCS	[M-2H]-	232.818	30932474
DeepCCS	[M+Na]+	208.163	30932474
AllCCS	[M+H]+	207.8	32859911
AllCCS	[M+H-H2O]+	205.8	32859911
AllCCS	[M+NH4]+	209.6	32859911
AllCCS	[M+Na]+	210.1	32859911
AllCCS	[M-H]-	205.2	32859911
AllCCS	[M+Na-2H]-	206.6	32859911
AllCCS	[M+HCOO]-	208.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1b,3a,7b-Trihydroxy-5b-cholanoic acid	C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(O)=O)[C@@H](O)CC1C[C@H](O)C[C@@H](O)[C@]31C	3737.8	Standard polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid	C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(O)=O)[C@@H](O)CC1C[C@H](O)C[C@@H](O)[C@]31C	3498.2	Standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid	C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(O)=O)[C@@H](O)CC1C[C@H](O)C[C@@H](O)[C@]31C	3866.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1b,3a,7b-Trihydroxy-5b-cholanoic acid,1TMS,isomer #1	C[C@]12CCC3C(C1CCC2[C@@H](CCCC(=O)O)O[Si](C)(C)C)[C@@H](O)CC1C[C@H](O)C[C@@H](O)[C@@]13C	3734.0	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,1TMS,isomer #2	C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(=O)O[Si](C)(C)C)[C@@H](O)CC1C[C@H](O)C[C@@H](O)[C@@]13C	3734.5	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,1TMS,isomer #3	C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(=O)O)[C@@H](O[Si](C)(C)C)CC1C[C@H](O)C[C@@H](O)[C@@]13C	3789.3	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,1TMS,isomer #4	C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(=O)O)[C@@H](O)CC1C[C@H](O[Si](C)(C)C)C[C@@H](O)[C@@]13C	3777.5	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,1TMS,isomer #5	C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(=O)O)[C@@H](O)CC1C[C@H](O)C[C@@H](O[Si](C)(C)C)[C@@]13C	3789.9	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TMS,isomer #1	C[C@]12CCC3C(C1CCC2[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)CC1C[C@H](O)C[C@@H](O)[C@@]13C	3692.4	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TMS,isomer #10	C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(=O)O)[C@@H](O)CC1C[C@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@]13C	3728.1	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TMS,isomer #2	C[C@]12CCC3C(C1CCC2[C@@H](CCCC(=O)O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)CC1C[C@H](O)C[C@@H](O)[C@@]13C	3687.2	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TMS,isomer #3	C[C@]12CCC3C(C1CCC2[C@@H](CCCC(=O)O)O[Si](C)(C)C)[C@@H](O)CC1C[C@H](O[Si](C)(C)C)C[C@@H](O)[C@@]13C	3700.5	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TMS,isomer #4	C[C@]12CCC3C(C1CCC2[C@@H](CCCC(=O)O)O[Si](C)(C)C)[C@@H](O)CC1C[C@H](O)C[C@@H](O[Si](C)(C)C)[C@@]13C	3687.9	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TMS,isomer #5	C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)CC1C[C@H](O)C[C@@H](O)[C@@]13C	3751.4	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TMS,isomer #6	C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(=O)O[Si](C)(C)C)[C@@H](O)CC1C[C@H](O[Si](C)(C)C)C[C@@H](O)[C@@]13C	3736.0	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TMS,isomer #7	C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(=O)O[Si](C)(C)C)[C@@H](O)CC1C[C@H](O)C[C@@H](O[Si](C)(C)C)[C@@]13C	3733.9	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TMS,isomer #8	C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(=O)O)[C@@H](O[Si](C)(C)C)CC1C[C@H](O[Si](C)(C)C)C[C@@H](O)[C@@]13C	3756.8	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TMS,isomer #9	C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(=O)O)[C@@H](O[Si](C)(C)C)CC1C[C@H](O)C[C@@H](O[Si](C)(C)C)[C@@]13C	3759.9	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TMS,isomer #1	C[C@]12CCC3C(C1CCC2[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)CC1C[C@H](O)C[C@@H](O)[C@@]13C	3583.9	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TMS,isomer #10	C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(=O)O)[C@@H](O[Si](C)(C)C)CC1C[C@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@]13C	3648.5	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TMS,isomer #2	C[C@]12CCC3C(C1CCC2[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)CC1C[C@H](O[Si](C)(C)C)C[C@@H](O)[C@@]13C	3597.7	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TMS,isomer #3	C[C@]12CCC3C(C1CCC2[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)CC1C[C@H](O)C[C@@H](O[Si](C)(C)C)[C@@]13C	3596.4	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TMS,isomer #4	C[C@]12CCC3C(C1CCC2[C@@H](CCCC(=O)O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)CC1C[C@H](O[Si](C)(C)C)C[C@@H](O)[C@@]13C	3574.7	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TMS,isomer #5	C[C@]12CCC3C(C1CCC2[C@@H](CCCC(=O)O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)CC1C[C@H](O)C[C@@H](O[Si](C)(C)C)[C@@]13C	3584.8	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TMS,isomer #6	C[C@]12CCC3C(C1CCC2[C@@H](CCCC(=O)O)O[Si](C)(C)C)[C@@H](O)CC1C[C@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@]13C	3589.1	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TMS,isomer #7	C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)CC1C[C@H](O[Si](C)(C)C)C[C@@H](O)[C@@]13C	3642.6	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TMS,isomer #8	C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)CC1C[C@H](O)C[C@@H](O[Si](C)(C)C)[C@@]13C	3647.5	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TMS,isomer #9	C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(=O)O[Si](C)(C)C)[C@@H](O)CC1C[C@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@]13C	3625.2	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,4TMS,isomer #1	C[C@]12CCC3C(C1CCC2[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)CC1C[C@H](O[Si](C)(C)C)C[C@@H](O)[C@@]13C	3514.6	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,4TMS,isomer #2	C[C@]12CCC3C(C1CCC2[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)CC1C[C@H](O)C[C@@H](O[Si](C)(C)C)[C@@]13C	3528.2	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,4TMS,isomer #3	C[C@]12CCC3C(C1CCC2[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)CC1C[C@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@]13C	3515.8	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,4TMS,isomer #4	C[C@]12CCC3C(C1CCC2[C@@H](CCCC(=O)O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)CC1C[C@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@]13C	3524.0	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,4TMS,isomer #5	C[C@]12CCC3C(C1CCC2[C@H](O)CCCC(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)CC1C[C@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@]13C	3572.5	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,5TMS,isomer #1	C[C@]12CCC3C(C1CCC2[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)CC1C[C@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@]13C	3475.8	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H](CCCC(=O)O)C1CCC2C3C(CC[C@@]21C)[C@]1(C)C(C[C@H](O)C[C@H]1O)C[C@@H]3O	3983.0	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@]1(C)C(C[C@H](O)C[C@H]1O)C[C@@H]3O	3990.0	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1CC2C[C@H](O)C[C@@H](O)[C@]2(C)C2CC[C@@]3(C)C(CCC3[C@H](O)CCCC(=O)O)C21	4009.1	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1CC2C[C@H](O)C3C4CCC([C@H](O)CCCC(=O)O)[C@@]4(C)CCC3[C@@]2(C)[C@H](O)C1	4002.7	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](O)CC2C[C@H](O)C3C4CCC([C@H](O)CCCC(=O)O)[C@@]4(C)CCC3[C@]21C	4002.8	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@@]21C)[C@]1(C)C(C[C@H](O)C[C@H]1O)C[C@@H]3O	4198.6	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@H]1CC2C[C@H](O)C3C4CCC([C@H](O)CCCC(=O)O)[C@@]4(C)CCC3[C@@]2(C)[C@H](O[Si](C)(C)C(C)(C)C)C1	4114.7	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1CC2C[C@H](O)C3C4CCC([C@@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)[C@@]4(C)CCC3[C@@]2(C)[C@H](O)C1	4180.7	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H](CCCC(=O)O)C1CCC2C3C(CC[C@@]21C)[C@]1(C)C(C[C@H](O)C[C@H]1O[Si](C)(C)C(C)(C)C)C[C@@H]3O	4149.3	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1CC2C[C@H](O)C[C@@H](O)[C@]2(C)C2CC[C@@]3(C)C(CCC3[C@@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)C21	4165.9	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@]1(C)C(C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O)C[C@@H]3O	4199.3	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@]1(C)C(C[C@H](O)C[C@H]1O[Si](C)(C)C(C)(C)C)C[C@@H]3O	4174.1	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@]1(C)C(C[C@H](O)C[C@H]1O)C[C@@H]3O[Si](C)(C)C(C)(C)C	4202.7	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@H]1CC2C[C@H](O[Si](C)(C)C(C)(C)C)C3C4CCC([C@H](O)CCCC(=O)O)[C@@]4(C)CCC3[C@@]2(C)[C@H](O)C1	4180.1	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@H]1CC2C[C@H](O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@]2(C)C2CC[C@@]3(C)C(CCC3[C@H](O)CCCC(=O)O)C21	4170.0	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@@]21C)[C@]1(C)C(C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O)C[C@@H]3O	4317.6	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@H]1CC2C[C@H](O[Si](C)(C)C(C)(C)C)C3C4CCC([C@H](O)CCCC(=O)O)[C@@]4(C)CCC3[C@@]2(C)[C@H](O[Si](C)(C)C(C)(C)C)C1	4235.8	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@@]21C)[C@]1(C)C(C[C@H](O)C[C@H]1O[Si](C)(C)C(C)(C)C)C[C@@H]3O	4294.6	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@@]21C)[C@]1(C)C(C[C@H](O)C[C@H]1O)C[C@@H]3O[Si](C)(C)C(C)(C)C	4299.6	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1CC2C[C@H](O[Si](C)(C)C(C)(C)C)C3C4CCC([C@@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)[C@@]4(C)CCC3[C@@]2(C)[C@H](O)C1	4287.9	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@H]1CC2C[C@H](O)C3C4CCC([C@@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)[C@@]4(C)CCC3[C@@]2(C)[C@H](O[Si](C)(C)C(C)(C)C)C1	4244.9	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@H]1CC2C[C@H](O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@]2(C)C2CC[C@@]3(C)C(CCC3[C@@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)C21	4283.3	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@]1(C)C(C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)C[C@@H]3O	4250.3	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@]1(C)C(C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O)C[C@@H]3O[Si](C)(C)C(C)(C)C	4301.3	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@]1(C)C(C[C@H](O)C[C@H]1O[Si](C)(C)C(C)(C)C)C[C@@H]3O[Si](C)(C)C(C)(C)C	4283.1	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@@]21C)[C@]1(C)C(C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)C[C@@H]3O	4365.5	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@@]21C)[C@]1(C)C(C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O)C[C@@H]3O[Si](C)(C)C(C)(C)C	4406.4	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@@]21C)[C@]1(C)C(C[C@H](O)C[C@H]1O[Si](C)(C)C(C)(C)C)C[C@@H]3O[Si](C)(C)C(C)(C)C	4414.5	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1CC2C[C@H](O[Si](C)(C)C(C)(C)C)C3C4CCC([C@@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)[C@@]4(C)CCC3[C@@]2(C)[C@H](O[Si](C)(C)C(C)(C)C)C1	4359.6	Semi standard non polar	33892256
1b,3a,7b-Trihydroxy-5b-cholanoic acid,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O)C1CCC2C3C(CC[C@@]21C)[C@]1(C)C(C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)C[C@@H]3O[Si](C)(C)C(C)(C)C	4366.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1b,3a,7b-Trihydroxy-5b-cholanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-057i-0259200000-548951fb57f423c7e4c2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1b,3a,7b-Trihydroxy-5b-cholanoic acid GC-MS (3 TMS) - 70eV, Positive	splash10-00b9-2120398000-13a7de5dcf35c15ffd81	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1b,3a,7b-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 - 1b,3a,7b-Trihydroxy-5b-cholanoic acid 10V, Positive-QTOF	splash10-052r-0009600000-e389ed646d1a4be3386e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1b,3a,7b-Trihydroxy-5b-cholanoic acid 20V, Positive-QTOF	splash10-000i-0019200000-74f9bc6344ea79571b89	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1b,3a,7b-Trihydroxy-5b-cholanoic acid 40V, Positive-QTOF	splash10-00ks-0069000000-fc660c8de3a3fc223fd7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1b,3a,7b-Trihydroxy-5b-cholanoic acid 10V, Negative-QTOF	splash10-05fr-0003900000-c4d41c4ee30c6fc7f6ca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1b,3a,7b-Trihydroxy-5b-cholanoic acid 20V, Negative-QTOF	splash10-0a4i-1006900000-1a3fc4580ed27846c22f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1b,3a,7b-Trihydroxy-5b-cholanoic acid 40V, Negative-QTOF	splash10-0a4i-5019000000-0f836598fa1e055939b1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1b,3a,7b-Trihydroxy-5b-cholanoic acid 10V, Positive-QTOF	splash10-002r-0009700000-be4306453f267fb010f6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1b,3a,7b-Trihydroxy-5b-cholanoic acid 20V, Positive-QTOF	splash10-000i-1359200000-17ba93bdaa36abe7bebb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1b,3a,7b-Trihydroxy-5b-cholanoic acid 40V, Positive-QTOF	splash10-0570-4594000000-9dd6f94bb7191e1d7768	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1b,3a,7b-Trihydroxy-5b-cholanoic acid 10V, Negative-QTOF	splash10-00di-0000900000-f2b8ea5cd784108b4f12	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1b,3a,7b-Trihydroxy-5b-cholanoic acid 20V, Negative-QTOF	splash10-05fr-1015900000-0b15d06ac54c83e2a167	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1b,3a,7b-Trihydroxy-5b-cholanoic acid 40V, Negative-QTOF	splash10-0fkl-9023400000-c77a070b8d3c1bea8740	2021-09-25	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

FDB029314

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

53481636

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 1b,3a,7b-Trihydroxy-5b-cholanoic acid (HMDB0013158)

MOL for HMDB0013158 (1b,3a,7b-Trihydroxy-5b-cholanoic acid)

3D MOL for HMDB0013158 (1b,3a,7b-Trihydroxy-5b-cholanoic acid)

3D SDF for HMDB0013158 (1b,3a,7b-Trihydroxy-5b-cholanoic acid)

3D-SDF for HMDB0013158 (1b,3a,7b-Trihydroxy-5b-cholanoic acid)

PDB for HMDB0013158 (1b,3a,7b-Trihydroxy-5b-cholanoic acid)

3D PDB for HMDB0013158 (1b,3a,7b-Trihydroxy-5b-cholanoic acid)

SMILES for HMDB0013158 (1b,3a,7b-Trihydroxy-5b-cholanoic acid)

INCHI for HMDB0013158 (1b,3a,7b-Trihydroxy-5b-cholanoic acid)

Structure for HMDB0013158 (1b,3a,7b-Trihydroxy-5b-cholanoic acid)

3D Structure for HMDB0013158 (1b,3a,7b-Trihydroxy-5b-cholanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra