MiMeDB: Showing metabocard for Nutriacholic acid (MMDBc0000105)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:36:04 UTC

Update Date

2024-04-30 19:31:04 UTC

Metabolite ID

MMDBc0000105

Metabolite Identification

Common Name

Nutriacholic acid

Description

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

Structure

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


  Mrv1652305271900242D          

 32 35  0  0  1  0            999 V2000
   12.3055   -9.6019    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6374   -9.6019    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0212   -8.6675    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5004  -10.7449    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6657   -7.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5915   -8.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9440   -7.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3334   -6.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9992   -8.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4778   -9.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5181   -6.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1188   -9.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3279   -8.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8551   -8.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0642   -7.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7633  -10.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1900  -10.5587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8504   -7.1870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4996  -10.1070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0729  -10.0275    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.5521   -7.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7087   -8.9908    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.2819   -8.9112    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9263  -10.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0011   -6.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9723   -9.3629    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5455   -9.2833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7546   -8.1671    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3366  -10.3995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6167  -10.6383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2993   -5.2584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1858   -6.1539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 18  5  1  6  0  0  0
 27  6  1  1  0  0  0
 28  7  1  1  0  0  0
  8 18  1  0  0  0  0
  8 11  1  0  0  0  0
 21  9  1  0  0  0  0
  9 10  1  0  0  0  0
 22 10  1  0  0  0  0
 11 25  1  0  0  0  0
 12 14  1  0  0  0  0
 12 20  1  0  0  0  0
 23 13  1  0  0  0  0
 13 15  1  0  0  0  0
 14 27  1  0  0  0  0
 15 28  1  0  0  0  0
 16 20  1  0  0  0  0
 19 16  1  0  0  0  0
 17 19  1  0  0  0  0
 17 24  1  0  0  0  0
 18 21  1  0  0  0  0
 19 27  1  0  0  0  0
 20 29  1  6  0  0  0
 21 28  1  0  0  0  0
 22 26  1  0  0  0  0
 22 28  1  0  0  0  0
 23 26  1  0  0  0  0
 23 27  1  0  0  0  0
 26 24  1  0  0  0  0
 24 30  2  0  0  0  0
 25 31  1  0  0  0  0
 25 32  2  0  0  0  0
 19  4  1  1  0  0  0
 26  3  1  1  0  0  0
 22  2  1  6  0  0  0
 23  1  1  6  0  0  0
M  END

HMDB0000467
     RDKit          3D
Nutriacholic acid
 66 69  0  0  0  0  0  0  0  0999 V2000
   -3.6071   -2.0314   -0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4462   -0.6090   -1.0622 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8349   -0.0308   -1.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7023   -0.0312   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0238    0.5696   -0.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2263    0.9617   -1.6292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0557    0.7118    0.4564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6312    0.2116   -0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5518    1.6749   -0.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3417    2.1475    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4238    1.0457   -0.1622 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8440    0.9540    0.5725 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6671    2.1692    0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079    3.2435    0.6493 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9762    1.9987   -0.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7413    0.9107    0.4232 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0582    0.7393   -0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8661   -0.4074    0.2685 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0567   -0.4596   -0.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0830   -1.6862    0.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6570   -1.4955   -0.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9609   -0.3807    0.5062 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8442   -0.7195    1.9925 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6164   -0.1857   -0.1035 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8391   -1.4401   -0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6186   -1.2947   -0.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2648   -0.1978    0.1997 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1366   -0.4370    1.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7153   -2.3061   -0.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2589   -2.1728    0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1124   -2.7663   -1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0106   -0.6643   -2.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3203   -0.7440   -2.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8088    0.9303   -1.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2614    0.5172    0.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9581   -1.0321    0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6529    1.5479    0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2405    0.3205    0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2509    1.7248   -1.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4109    2.2594   -0.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9497    3.1024   -0.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5866    2.2558    1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2587    1.0347   -1.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7445    0.7853    1.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5762    2.9368   -0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9557    1.8315   -1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9779    1.3387    1.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6564    1.6602   -0.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9213    0.6233   -1.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1705   -0.1621    1.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3217    0.4853   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1942   -2.3056    1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721   -2.2921   -0.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5440   -1.3172   -1.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1096   -2.4380    0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2520   -1.6118    2.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4905    0.1920    2.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8680   -0.9123    2.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834    0.1791   -1.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050   -2.0822    0.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2939   -2.0690   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6265   -1.0398   -1.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0541   -2.3019   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0155   -1.0026    2.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2327   -0.9643    1.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1654    0.5282    2.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27  8  1  0
 27 11  1  0
 24 12  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  6
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  6
 12 44  1  1
 15 45  1  0
 15 46  1  0
 16 47  1  1
 17 48  1  0
 17 49  1  0
 18 50  1  1
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 23 56  1  0
 23 57  1  0
 23 58  1  0
 24 59  1  6
 25 60  1  0
 25 61  1  0
 26 62  1  0
 26 63  1  0
 28 64  1  0
 28 65  1  0
 28 66  1  0
M  END


  Mrv1652305271900242D          

 32 35  0  0  1  0            999 V2000
   12.3055   -9.6019    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6374   -9.6019    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0212   -8.6675    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5004  -10.7449    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6657   -7.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5915   -8.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9440   -7.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3334   -6.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9992   -8.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4778   -9.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5181   -6.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1188   -9.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3279   -8.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8551   -8.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0642   -7.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7633  -10.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1900  -10.5587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8504   -7.1870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4996  -10.1070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0729  -10.0275    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.5521   -7.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7087   -8.9908    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.2819   -8.9112    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9263  -10.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0011   -6.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9723   -9.3629    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5455   -9.2833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7546   -8.1671    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3366  -10.3995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6167  -10.6383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2993   -5.2584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1858   -6.1539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 18  5  1  6  0  0  0
 27  6  1  1  0  0  0
 28  7  1  1  0  0  0
  8 18  1  0  0  0  0
  8 11  1  0  0  0  0
 21  9  1  0  0  0  0
  9 10  1  0  0  0  0
 22 10  1  0  0  0  0
 11 25  1  0  0  0  0
 12 14  1  0  0  0  0
 12 20  1  0  0  0  0
 23 13  1  0  0  0  0
 13 15  1  0  0  0  0
 14 27  1  0  0  0  0
 15 28  1  0  0  0  0
 16 20  1  0  0  0  0
 19 16  1  0  0  0  0
 17 19  1  0  0  0  0
 17 24  1  0  0  0  0
 18 21  1  0  0  0  0
 19 27  1  0  0  0  0
 20 29  1  6  0  0  0
 21 28  1  0  0  0  0
 22 26  1  0  0  0  0
 22 28  1  0  0  0  0
 23 26  1  0  0  0  0
 23 27  1  0  0  0  0
 26 24  1  0  0  0  0
 24 30  2  0  0  0  0
 25 31  1  0  0  0  0
 25 32  2  0  0  0  0
 19  4  1  1  0  0  0
 26  3  1  1  0  0  0
 22  2  1  6  0  0  0
 23  1  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000105

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-19,22,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17?,18-,19-,22-,23-,24+/m0/s1

> <INCHI_KEY>
DXOCDBGWDZAYRQ-QPVZPPSOSA-N

> <FORMULA>
C24H38O4

> <MOLECULAR_WEIGHT>
390.5561

> <EXACT_MASS>
390.277009704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
44.93776957982735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.52

> <JCHEM_LOGP>
4.098819777333333

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.361716911793224

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.556917014493273

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3283852427336238

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
108.34859999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000467
     RDKit          3D
Nutriacholic acid
 66 69  0  0  0  0  0  0  0  0999 V2000
   -3.6071   -2.0314   -0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4462   -0.6090   -1.0622 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8349   -0.0308   -1.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7023   -0.0312   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0238    0.5696   -0.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2263    0.9617   -1.6292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0557    0.7118    0.4564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6312    0.2116   -0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5518    1.6749   -0.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3417    2.1475    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4238    1.0457   -0.1622 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8440    0.9540    0.5725 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6671    2.1692    0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079    3.2435    0.6493 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9762    1.9987   -0.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7413    0.9107    0.4232 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0582    0.7393   -0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8661   -0.4074    0.2685 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0567   -0.4596   -0.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0830   -1.6862    0.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6570   -1.4955   -0.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9609   -0.3807    0.5062 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8442   -0.7195    1.9925 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6164   -0.1857   -0.1035 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8391   -1.4401   -0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6186   -1.2947   -0.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2648   -0.1978    0.1997 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1366   -0.4370    1.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7153   -2.3061   -0.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2589   -2.1728    0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1124   -2.7663   -1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0106   -0.6643   -2.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3203   -0.7440   -2.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8088    0.9303   -1.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2614    0.5172    0.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9581   -1.0321    0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6529    1.5479    0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2405    0.3205    0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2509    1.7248   -1.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4109    2.2594   -0.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9497    3.1024   -0.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5866    2.2558    1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2587    1.0347   -1.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7445    0.7853    1.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5762    2.9368   -0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9557    1.8315   -1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9779    1.3387    1.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6564    1.6602   -0.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9213    0.6233   -1.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1705   -0.1621    1.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3217    0.4853   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1942   -2.3056    1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721   -2.2921   -0.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5440   -1.3172   -1.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1096   -2.4380    0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2520   -1.6118    2.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4905    0.1920    2.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8680   -0.9123    2.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834    0.1791   -1.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050   -2.0822    0.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2939   -2.0690   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6265   -1.0398   -1.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0541   -2.3019   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0155   -1.0026    2.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2327   -0.9643    1.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1654    0.5282    2.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27  8  1  0
 27 11  1  0
 24 12  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  6
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  6
 12 44  1  1
 15 45  1  0
 15 46  1  0
 16 47  1  1
 17 48  1  0
 17 49  1  0
 18 50  1  1
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 23 56  1  0
 23 57  1  0
 23 58  1  0
 24 59  1  6
 25 60  1  0
 25 61  1  0
 26 62  1  0
 26 63  1  0
 28 64  1  0
 28 65  1  0
 28 66  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  H   UNK     0      22.970 -17.924   0.000  0.00  0.00           H+0
HETATM    2  H   UNK     0      25.456 -17.924   0.000  0.00  0.00           H+0
HETATM    3  H   UNK     0      24.306 -16.179   0.000  0.00  0.00           H+0
HETATM    4  H   UNK     0      21.467 -20.057   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0      29.243 -13.180   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.637 -15.791   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.029 -13.746   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.756 -12.216   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.999 -16.146   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.025 -17.340   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.234 -12.451   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.888 -17.180   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.012 -15.097   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.263 -16.486   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.387 -14.402   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.091 -19.561   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.755 -19.710   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      27.721 -13.416   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.466 -18.866   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.803 -18.718   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.164 -14.852   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      25.590 -16.783   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.926 -16.634   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      24.129 -19.015   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      24.269 -11.252   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.215 -17.477   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      21.552 -17.329   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      25.675 -15.245   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      17.428 -19.412   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      25.418 -19.858   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      24.825  -9.816   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      22.747 -11.487   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2   22                                                            
CONECT    3   26                                                            
CONECT    4   19                                                            
CONECT    5   18                                                            
CONECT    6   27                                                            
CONECT    7   28                                                            
CONECT    8   18   11                                                       
CONECT    9   21   10                                                       
CONECT   10    9   22                                                       
CONECT   11    8   25                                                       
CONECT   12   14   20                                                       
CONECT   13   23   15                                                       
CONECT   14   12   27                                                       
CONECT   15   13   28                                                       
CONECT   16   20   19                                                       
CONECT   17   19   24                                                       
CONECT   18    5    8   21                                                  
CONECT   19   16   17   27    4                                             
CONECT   20   12   16   29                                                  
CONECT   21    9   18   28                                                  
CONECT   22   10   26   28    2                                             
CONECT   23   13   26   27    1                                             
CONECT   24   17   26   30                                                  
CONECT   25   11   31   32                                                  
CONECT   26   22   23   24    3                                             
CONECT   27    6   14   19   23                                             
CONECT   28    7   15   21   22                                             
CONECT   29   20                                                            
CONECT   30   24                                                            
CONECT   31   25                                                            
CONECT   32   25                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0000467
HETATM    1  C1  UNL     1      -3.607  -2.031  -0.624  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.446  -0.609  -1.062  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.835  -0.031  -1.284  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.702  -0.031  -0.071  1.00  0.00           C  
HETATM    5  C5  UNL     1      -7.024   0.570  -0.456  1.00  0.00           C  
HETATM    6  O1  UNL     1      -7.226   0.962  -1.629  1.00  0.00           O  
HETATM    7  O2  UNL     1      -8.056   0.712   0.456  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.631   0.212  -0.133  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.552   1.675  -0.643  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.342   2.148   0.182  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.424   1.046  -0.162  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.844   0.954   0.573  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.667   2.169   0.315  1.00  0.00           C  
HETATM   14  O3  UNL     1       1.208   3.244   0.649  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.976   1.999  -0.322  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.741   0.911   0.423  1.00  0.00           C  
HETATM   17  C14 UNL     1       5.058   0.739  -0.297  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.866  -0.407   0.269  1.00  0.00           C  
HETATM   19  O4  UNL     1       7.057  -0.460  -0.466  1.00  0.00           O  
HETATM   20  C16 UNL     1       5.083  -1.686   0.174  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.657  -1.495  -0.232  1.00  0.00           C  
HETATM   22  C18 UNL     1       2.961  -0.381   0.506  1.00  0.00           C  
HETATM   23  C19 UNL     1       2.844  -0.720   1.993  1.00  0.00           C  
HETATM   24  C20 UNL     1       1.616  -0.186  -0.104  1.00  0.00           C  
HETATM   25  C21 UNL     1       0.839  -1.440  -0.177  1.00  0.00           C  
HETATM   26  C22 UNL     1      -0.619  -1.295  -0.558  1.00  0.00           C  
HETATM   27  C23 UNL     1      -1.265  -0.198   0.200  1.00  0.00           C  
HETATM   28  C24 UNL     1      -1.137  -0.437   1.702  1.00  0.00           C  
HETATM   29  H1  UNL     1      -4.715  -2.306  -0.574  1.00  0.00           H  
HETATM   30  H2  UNL     1      -3.259  -2.173   0.412  1.00  0.00           H  
HETATM   31  H3  UNL     1      -3.112  -2.766  -1.299  1.00  0.00           H  
HETATM   32  H4  UNL     1      -3.011  -0.664  -2.094  1.00  0.00           H  
HETATM   33  H5  UNL     1      -5.320  -0.744  -2.017  1.00  0.00           H  
HETATM   34  H6  UNL     1      -4.809   0.930  -1.806  1.00  0.00           H  
HETATM   35  H7  UNL     1      -5.261   0.517   0.788  1.00  0.00           H  
HETATM   36  H8  UNL     1      -5.958  -1.032   0.325  1.00  0.00           H  
HETATM   37  H9  UNL     1      -8.653   1.548   0.395  1.00  0.00           H  
HETATM   38  H10 UNL     1      -3.240   0.320   0.814  1.00  0.00           H  
HETATM   39  H11 UNL     1      -2.251   1.725  -1.685  1.00  0.00           H  
HETATM   40  H12 UNL     1      -3.411   2.259  -0.333  1.00  0.00           H  
HETATM   41  H13 UNL     1      -0.950   3.102  -0.229  1.00  0.00           H  
HETATM   42  H14 UNL     1      -1.587   2.256   1.237  1.00  0.00           H  
HETATM   43  H15 UNL     1      -0.259   1.035  -1.253  1.00  0.00           H  
HETATM   44  H16 UNL     1       0.744   0.785   1.650  1.00  0.00           H  
HETATM   45  H17 UNL     1       3.576   2.937  -0.160  1.00  0.00           H  
HETATM   46  H18 UNL     1       2.956   1.832  -1.398  1.00  0.00           H  
HETATM   47  H19 UNL     1       3.978   1.339   1.419  1.00  0.00           H  
HETATM   48  H20 UNL     1       5.656   1.660  -0.124  1.00  0.00           H  
HETATM   49  H21 UNL     1       4.921   0.623  -1.381  1.00  0.00           H  
HETATM   50  H22 UNL     1       6.170  -0.162   1.318  1.00  0.00           H  
HETATM   51  H23 UNL     1       7.322   0.485  -0.625  1.00  0.00           H  
HETATM   52  H24 UNL     1       5.194  -2.306   1.086  1.00  0.00           H  
HETATM   53  H25 UNL     1       5.572  -2.292  -0.645  1.00  0.00           H  
HETATM   54  H26 UNL     1       3.544  -1.317  -1.316  1.00  0.00           H  
HETATM   55  H27 UNL     1       3.110  -2.438   0.023  1.00  0.00           H  
HETATM   56  H28 UNL     1       2.252  -1.612   2.180  1.00  0.00           H  
HETATM   57  H29 UNL     1       2.490   0.192   2.521  1.00  0.00           H  
HETATM   58  H30 UNL     1       3.868  -0.912   2.374  1.00  0.00           H  
HETATM   59  H31 UNL     1       1.783   0.179  -1.156  1.00  0.00           H  
HETATM   60  H32 UNL     1       0.905  -2.082   0.723  1.00  0.00           H  
HETATM   61  H33 UNL     1       1.294  -2.069  -1.002  1.00  0.00           H  
HETATM   62  H34 UNL     1      -0.626  -1.040  -1.641  1.00  0.00           H  
HETATM   63  H35 UNL     1      -1.054  -2.302  -0.370  1.00  0.00           H  
HETATM   64  H36 UNL     1      -2.015  -1.003   2.057  1.00  0.00           H  
HETATM   65  H37 UNL     1      -0.233  -0.964   1.991  1.00  0.00           H  
HETATM   66  H38 UNL     1      -1.165   0.528   2.272  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    8   32
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6    6    7
CONECT    7   37
CONECT    8    9   27   38
CONECT    9   10   39   40
CONECT   10   11   41   42
CONECT   11   12   27   43
CONECT   12   13   24   44
CONECT   13   14   14   15
CONECT   15   16   45   46
CONECT   16   17   22   47
CONECT   17   18   48   49
CONECT   18   19   20   50
CONECT   19   51
CONECT   20   21   52   53
CONECT   21   22   54   55
CONECT   22   23   24
CONECT   23   56   57   58
CONECT   24   25   59
CONECT   25   26   60   61
CONECT   26   27   62   63
CONECT   27   28
CONECT   28   64   65   66
END

HMDB0000467
     RDKit          3D
Nutriacholic acid
 66 69  0  0  0  0  0  0  0  0999 V2000
   -3.6071   -2.0314   -0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4462   -0.6090   -1.0622 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8349   -0.0308   -1.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7023   -0.0312   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0238    0.5696   -0.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2263    0.9617   -1.6292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0557    0.7118    0.4564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6312    0.2116   -0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5518    1.6749   -0.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3417    2.1475    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4238    1.0457   -0.1622 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8440    0.9540    0.5725 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6671    2.1692    0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079    3.2435    0.6493 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9762    1.9987   -0.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7413    0.9107    0.4232 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0582    0.7393   -0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8661   -0.4074    0.2685 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0567   -0.4596   -0.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0830   -1.6862    0.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6570   -1.4955   -0.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9609   -0.3807    0.5062 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8442   -0.7195    1.9925 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6164   -0.1857   -0.1035 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8391   -1.4401   -0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6186   -1.2947   -0.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2648   -0.1978    0.1997 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1366   -0.4370    1.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7153   -2.3061   -0.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2589   -2.1728    0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1124   -2.7663   -1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0106   -0.6643   -2.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3203   -0.7440   -2.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8088    0.9303   -1.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2614    0.5172    0.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9581   -1.0321    0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6529    1.5479    0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2405    0.3205    0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2509    1.7248   -1.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4109    2.2594   -0.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9497    3.1024   -0.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5866    2.2558    1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2587    1.0347   -1.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7445    0.7853    1.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5762    2.9368   -0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9557    1.8315   -1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9779    1.3387    1.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6564    1.6602   -0.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9213    0.6233   -1.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1705   -0.1621    1.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3217    0.4853   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1942   -2.3056    1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721   -2.2921   -0.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5440   -1.3172   -1.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1096   -2.4380    0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2520   -1.6118    2.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4905    0.1920    2.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8680   -0.9123    2.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834    0.1791   -1.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050   -2.0822    0.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2939   -2.0690   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6265   -1.0398   -1.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0541   -2.3019   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0155   -1.0026    2.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2327   -0.9643    1.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1654    0.5282    2.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27  8  1  0
 27 11  1  0
 24 12  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  6
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  6
 12 44  1  1
 15 45  1  0
 15 46  1  0
 16 47  1  1
 17 48  1  0
 17 49  1  0
 18 50  1  1
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 23 56  1  0
 23 57  1  0
 23 58  1  0
 24 59  1  6
 25 60  1  0
 25 61  1  0
 26 62  1  0
 26 63  1  0
 28 64  1  0
 28 65  1  0
 28 66  1  0
M  END

Synonyms

Value	Source
Nutriacholate	Generator
3a-Hydroxy-7-oxo-5b-cholanoate	HMDB
3a-Hydroxy-7-oxo-5b-cholanoic acid	HMDB
5b-Cholanic acid-3a-ol-7-one	HMDB
7-Ketochenodeoxycholate	HMDB
7-Ketochenodeoxycholic acid	HMDB
7-Ketolithocholate	HMDB
7-Ketolithocholic acid	HMDB, MeSH
7-oxo-3a-Hydroxycholan-24-Oate	HMDB
7-oxo-3a-Hydroxycholan-24-Oic acid	HMDB
7-Oxolithocholate	HMDB
7-Oxolithocholic acid	HMDB, MeSH
3 alpha-Hydroxy-7-keto-5 beta-cholanoate	MeSH, HMDB
3 alpha-Ol-7-one-5 beta-cholanoic acid	MeSH, HMDB
7-Ketolithocholic acid, (3beta,5alpha)-isomer	MeSH, HMDB
(4S)-4-[(1S,2S,5R,7S,10R,11S,15R)-5-Hydroxy-2,15-dimethyl-9-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	Generator, HMDB

Molecular Formula

C₂₄H₃₈O₄

Average Mass

390.5561

Monoisotopic Mass

390.277009704

IUPAC Name

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

Traditional Name

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

CAS Registry Number

4651-67-6

SMILES

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

InChI Identifier

InChI=1S/C24H38O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-19,22,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17?,18-,19-,22-,23-,24+/m0/s1

InChI Key

DXOCDBGWDZAYRQ-QPVZPPSOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Monohydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	3.52	ALOGPS
logP	4.1	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.56	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.35 m³·mol⁻¹	ChemAxon
Polarizability	44.94 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03gj-0319000000-99c0cf456750a298fdba	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-2141590000-df782bc25f3fffc7b8b0	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-0291000000-9f5bf5f94dd6944d6d6f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-052r-2962000000-f18d1686d1ac8b6e93f3	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-05o1-2900000000-681b2fd8ee33b91d7a44	2012-07-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-0009000000-96e2b732bac67ff31b5c	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-076s-0009000000-63349742d082a77d840f	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01t9-0229000000-c96c7b6b3568bc1568ec	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-bcd0337fb08276e5242b	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dr-0009000000-8e05a17c162e99bd54ed	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9006000000-ddfed24aad7a991420fa	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-1bf3e4a9164eecd8b5ad	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0079-0009000000-dabdf5ac37340fa8a343	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052r-3029000000-ec70dabf7a7d2522ff70	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0596-0009000000-aa05b3718c19db13d245	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-2059000000-993d476f495649000a3f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0adj-2931000000-238650ed3f34647466eb	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Feces
Gall Bladder
Intestine
Kidney
Liver

Tissue Locations

Gall Bladder
Intestine
Kidney
Liver

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192108	Solute carrier organic anion transporter family member 1B3	Transporter	Q9NPD5	Homo sapiens
MMDBp0192115	Solute carrier organic anion transporter family member 1B1	Transporter	Q9Y6L6	Homo sapiens
MMDBp0193395	Canalicular multispecific organic anion transporter 2	Transporter	O15438	Homo sapiens
MMDBp0193400	Bile salt export pump	Transporter	O95342	Homo sapiens
MMDBp0193547	Ileal sodium/bile acid cotransporter	Transporter	Q12908	Homo sapiens
MMDBp0193577	Sodium/bile acid cotransporter	Transporter	Q14973	Homo sapiens
MMDBp0193639	Solute carrier organic anion transporter family member 1A2	Transporter	P46721	Homo sapiens
MMDBp0193865	Solute carrier organic anion transporter family member 4A1	Transporter	Q96BD0	Homo sapiens
MMDBp0195864	Gastrotropin	Unknown	P51161	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0006120	Chenodeoxycholic acid	Nutriacholic acid	Not Available	Formation of 7-Ketolithocholate	VMH	30371894
MMDBr0006121	Nutriacholic acid	Ursodeoxycholic acid	Not Available	Formation of Ursodeoxycholate	VMH	30371894
MMDBr0006885	Nutriacholic acid	Nutriacholic acid	Atp-binding cassette, sub-family b (mdr/tap), member 11	Transport of 7-Ketolithocholate, Active Transport	VMH	30371894
MMDBr0006886	Nutriacholic acid	Nutriacholic acid	Solute carrier family 10 (sodium/bile acid cotransporter), member 1	Transport of 7-Ketolithocholate, Sodium Symport	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Microbial culture
Bacteria	Bacteroidetes	1	Human ; Human feces	Microbial culture

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Gall bladder	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified	Infant (0-1 year old)	NULL	Normal	HMDB	24628373
Human Feces	Detected but not Quantified	Adult (>18 years old)	Not Specified	Normal	HMDB	21458633
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	23384618
Human Feces	Detected but not Quantified	Infant (0-1 year old)	Not Specified	Normal	HMDB	24628373
Human Feces	Detected but not Quantified	Infant (0-1 year old)	Not Specified	Normal	HMDB	24628373
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000467

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022059

KNApSAcK ID

Not Available

Chemspider ID

59651435

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5454

PubChem Compound

53477693

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Fromm H, Sarva RP, Bazzoli F: Formation of ursodeoxycholic acid from chenodeoxycholic acid in the human colon: studies of the role of 7-ketolithocholic acid as an intermediate. J Lipid Res. 1983 Jul;24(7):841-53. [PubMed:6631218 ]
Amuro Y, Yamade W, Kudo K, Yamamoto T, Hada T, Higashino K: Reduction of 7-ketolithocholic acid by human liver enzyme preparations in vitro. Am J Physiol. 1989 Jan;256(1 Pt 1):G67-71. doi: 10.1152/ajpgi.1989.256.1.G67. [PubMed:2912152 ]
Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
Salen G, Verga D, Batta AK, Tint GS, Shefer S: Effect of 7-ketolithocholic acid on bile acid metabolism in humans. Gastroenterology. 1982 Aug;83(2):341-7. [PubMed:7084613 ]
Albini E, Marca G, Mellerio G: Further observations on the in vitro metabolism of chenodeoxycholic acid and ursodeoxycholic acid. Arzneimittelforschung. 1982;32(12):1554-7. [PubMed:6891595 ]
Higashi S, Setoguchi T, Katsuki T: Conversion of 7-ketolithocholic acid to ursodeoxycholic acid by human intestinal anaerobic microorganisms: interchangeability of chenodeoxycholic acid and ursodeoxycholic acid. Gastroenterol Jpn. 1979 Oct;14(5):417-24. doi: 10.1007/BF02773728. [PubMed:520764 ]
Fedorowski T, Salen G, Tint GS, Mosbach E: Transformation of chenodeoxycholic acid and ursodeoxycholic acid by human intestinal bacteria. Gastroenterology. 1979 Nov;77(5):1068-73. [PubMed:488633 ]
Akao T, Akao T, Hattori M, Namba T, Kobashi K: Enzymes involved in the formation of 3 beta, 7 beta-dihydroxy-12-oxo-5 beta-cholanic acid from dehydrocholic acid by Ruminococcus sp. obtained from human intestine. Biochim Biophys Acta. 1987 Sep 25;921(2):275-80. [PubMed:3477291 ]
Fromm H, Carlson GL, Hofmann AF, Farivar S, Amin P: Metabolism in man of 7-ketolithocholic acid: precursor of cheno- and ursodeoxycholic acids. Am J Physiol. 1980 Sep;239(3):G161-6. doi: 10.1152/ajpgi.1980.239.3.G161. [PubMed:7435569 ]
Miwa H, Yamamoto M, Nishida T, Yao T: Transformation of chenodeoxycholic acid to ursodeoxycholic acid in patients with Crohn's disease. Gastroenterology. 1986 Mar;90(3):718-23. doi: 10.1016/0016-5085(86)91128-5. [PubMed:3943699 ]
Roda A, Cappelleri G, Aldini R, Roda E, Barbara L: Quantitative aspects of the interaction of bile acids with human serum albumin. J Lipid Res. 1982 Mar;23(3):490-5. [PubMed:7077161 ]
Salen G, Tint GS, Eliav B, Deering N, Mosbach EH: Increased formation of ursodeoxycholic acid in patients treated with chenodeoxycholic acid. J Clin Invest. 1974 Feb;53(2):612-21. doi: 10.1172/JCI107596. [PubMed:11344576 ]
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. doi: 10.1242/jeb.204.10.1673. [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. doi: 10.1161/01.ATV.0000178994.21828.a7. 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. doi: 10.1152/ajpgi.00417.2002. [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 ]

Showing metabocard for Nutriacholic acid (MMDBc0000105)

MOL for #<Metabolite:0x000055c79c6f9c30>

3D MOL for #<Metabolite:0x000055c79c6f9c30>

3D SDF for #<Metabolite:0x000055c79c6f9c30>

3D-SDF for #<Metabolite:0x000055c79c6f9c30>

PDB for #<Metabolite:0x000055c79c6f9c30>

3D PDB for #<Metabolite:0x000055c79c6f9c30>

SMILES for #<Metabolite:0x000055c79c6f9c30>

INCHI for #<Metabolite:0x000055c79c6f9c30>

Structure for #<Metabolite:0x000055c79c6f9c30>

3D Structure for #<Metabolite:0x000055c79c6f9c30>