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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (8) Show 12 proteins XML

enzymes (4)transporters (8) Show 12 proteins

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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:00 UTC

HMDB ID

HMDB0000359

Secondary Accession Numbers

HMDB0001974
HMDB00359
HMDB01974

Metabolite Identification

Common Name

3alpha,7alpha-Dihydroxycoprostanic acid

Description

3α,7α-Dihydroxycoprostanic acid is a bile acid excreted in small amounts in the urine of healthy subjects (PMID: 864325 ). 3α,7α-Dihydroxycoprostanic acid is the precursor to chenodeoxycholic acid, 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.

Structure

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

  Mrv1652304202019412D          

 36 39  0  0  1  0            999 V2000
    5.1383   -4.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1383   -4.9052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8526   -3.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8526   -5.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2817   -5.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5672   -4.0801    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2817   -3.6677    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9961   -4.0801    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9961   -4.9052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5672   -4.9052    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2817   -2.8426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4952   -3.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9802   -3.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5672   -3.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2817   -4.4927    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9961   -3.2552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7106   -3.6677    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7106   -2.8426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7106   -2.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7106   -4.4927    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9961   -2.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7106   -5.3177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4238   -5.3177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5672   -5.7302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7807   -1.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4952   -1.7628    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2097   -1.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9242   -1.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6387   -1.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3531   -2.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3531   -1.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0676   -0.5253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0676   -1.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7821   -1.7628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4952   -2.5878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2097   -2.1753    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  1  0  0  0  0
  2 23  1  6  0  0  0
  2  4  1  0  0  0  0
  6  3  1  0  0  0  0
 10  4  1  0  0  0  0
  5  9  1  0  0  0  0
 10  5  1  0  0  0  0
  6 14  1  1  0  0  0
  7  6  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  7 15  1  6  0  0  0
  8  7  1  0  0  0  0
 17  8  1  0  0  0  0
  8 16  1  1  0  0  0
  8  9  1  0  0  0  0
  9 22  1  6  0  0  0
 10 24  1  1  0  0  0
 11 21  1  0  0  0  0
 17 12  1  0  0  0  0
 13 12  1  0  0  0  0
 13 35  1  0  0  0  0
 17 18  1  0  0  0  0
 17 20  1  6  0  0  0
 18 35  1  0  0  0  0
 18 21  1  0  0  0  0
 18 19  1  1  0  0  0
 35 26  1  0  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 31  1  0  0  0  0
 31 30  1  0  0  0  0
 31 33  1  0  0  0  0
 33 32  2  0  0  0  0
 33 34  1  0  0  0  0
 35 36  1  6  0  0  0
M  END

HMDB0000359
     RDKit          3D
3alpha,7alpha-Dihydroxycoprostanic acid
 77 80  0  0  0  0  0  0  0  0999 V2000
    7.3633    0.1703    0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6191    1.2787    0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5621    0.6484   -0.6652 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5887   -0.1682    0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5388   -0.8066   -0.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5198   -1.6363    0.0086 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1538   -2.8242    0.7584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4071   -1.1429    0.7733 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5597   -0.3398    2.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1043    0.0505    2.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7006   -0.4705    1.2034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9849    0.1755    0.9106 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5298   -0.2625   -0.4254 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5256   -0.3345   -1.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2992   -1.1099   -1.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3137   -0.3951    0.0597 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6039    1.0426   -0.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6977    0.6075   -0.7580 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2206    2.0619   -0.7555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2744    0.2385   -2.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5212    1.0169   -2.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5720    0.8901   -1.3483 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.6925    0.2365   -1.8953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0842    0.0611   -0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7310    0.4760    0.3112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3518   -0.5359    1.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917   -0.3034    1.9533 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5512   -1.5192    2.4814 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6208    2.0216   -0.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7929    3.2323   -0.3257 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3877    1.4231   -1.5297 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4469   -0.6697    0.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8852   -0.1096    1.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3873    0.5180    1.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1626    1.9237    1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0343    1.4751   -1.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0177   -0.0402   -1.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2195   -0.8447    0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691    0.5766    0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0879   -0.0375   -1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0987   -1.4602   -1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0253   -2.2136   -0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4111   -3.6167    0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5885   -2.5209    1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9611   -3.2792    0.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8716   -2.0893    1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0980    0.5936    1.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8819   -0.9907    2.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0260    1.1523    2.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2048   -0.3263    3.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8676   -1.5571    1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9881    1.2858    0.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9239   -1.3089   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2850    0.6406   -1.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062   -0.9277   -2.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6922   -2.0937   -0.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3878   -1.3111   -1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6168    1.3582    0.1383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1005    1.7118    0.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4894    1.3403   -1.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1296    2.1405   -0.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6676    2.6451   -1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5059    2.5786    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5675    0.3929   -2.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5278   -0.8310   -2.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9010    0.6097   -3.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3475    2.0883   -2.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9521    1.8785   -1.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4645    0.2439   -1.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0287   -1.0076   -0.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8039    0.1477    0.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9037    1.4428    0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5047   -1.5714    0.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1169   -0.4138    2.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0560    0.4300    2.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8000   -2.2442    1.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1237    0.7489   -1.3369 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  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
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 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 13 18  1  0
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 18 20  1  0
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 22 23  1  0
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 25 26  1  0
 26 27  1  0
 27 28  1  0
  2 29  1  0
 29 30  2  0
 29 31  1  0
 16  8  1  0
 25 18  1  0
 16 11  1  0
 27 12  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  6
  7 43  1  0
  7 44  1  0
  7 45  1  0
  8 46  1  1
  9 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  1
 12 52  1  6
 13 53  1  1
 14 54  1  0
 14 55  1  0
 15 56  1  0
 15 57  1  0
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 24 70  1  0
 24 71  1  0
 25 72  1  1
 26 73  1  0
 26 74  1  0
 27 75  1  1
 28 76  1  0
 31 77  1  0
M  END

  Mrv1652304202019412D          

 36 39  0  0  1  0            999 V2000
    5.1383   -4.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1383   -4.9052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8526   -3.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8526   -5.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2817   -5.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5672   -4.0801    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2817   -3.6677    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9961   -4.0801    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9961   -4.9052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5672   -4.9052    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2817   -2.8426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4952   -3.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9802   -3.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5672   -3.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2817   -4.4927    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9961   -3.2552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7106   -3.6677    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7106   -2.8426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7106   -2.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7106   -4.4927    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9961   -2.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7106   -5.3177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4238   -5.3177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5672   -5.7302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7807   -1.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4952   -1.7628    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2097   -1.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9242   -1.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6387   -1.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3531   -2.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3531   -1.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0676   -0.5253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0676   -1.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7821   -1.7628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4952   -2.5878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2097   -2.1753    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  1  0  0  0  0
  2 23  1  6  0  0  0
  2  4  1  0  0  0  0
  6  3  1  0  0  0  0
 10  4  1  0  0  0  0
  5  9  1  0  0  0  0
 10  5  1  0  0  0  0
  6 14  1  1  0  0  0
  7  6  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  7 15  1  6  0  0  0
  8  7  1  0  0  0  0
 17  8  1  0  0  0  0
  8 16  1  1  0  0  0
  8  9  1  0  0  0  0
  9 22  1  6  0  0  0
 10 24  1  1  0  0  0
 11 21  1  0  0  0  0
 17 12  1  0  0  0  0
 13 12  1  0  0  0  0
 13 35  1  0  0  0  0
 17 18  1  0  0  0  0
 17 20  1  6  0  0  0
 18 35  1  0  0  0  0
 18 21  1  0  0  0  0
 18 19  1  1  0  0  0
 35 26  1  0  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 31  1  0  0  0  0
 31 30  1  0  0  0  0
 31 33  1  0  0  0  0
 33 32  2  0  0  0  0
 33 34  1  0  0  0  0
 35 36  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000359

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O4/c1-16(6-5-7-17(2)25(30)31)20-8-9-21-24-22(11-13-27(20,21)4)26(3)12-10-19(28)14-18(26)15-23(24)29/h16-24,28-29H,5-15H2,1-4H3,(H,30,31)/t16-,17?,18+,19-,20-,21+,22+,23-,24+,26+,27-/m1/s1

> <INCHI_KEY>
ITZYGDKGRKKBSN-HKFUITGCSA-N

> <FORMULA>
C27H46O4

> <MOLECULAR_WEIGHT>
434.661

> <EXACT_MASS>
434.339609961

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
52.20624287291586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R)-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid

> <ALOGPS_LOGP>
4.02

> <JCHEM_LOGP>
5.145429132000005

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.296339908541825

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.82892261028387

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5356619176938756

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
123.05029999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000359
     RDKit          3D
3alpha,7alpha-Dihydroxycoprostanic acid
 77 80  0  0  0  0  0  0  0  0999 V2000
    7.3633    0.1703    0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6191    1.2787    0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5621    0.6484   -0.6652 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5887   -0.1682    0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5388   -0.8066   -0.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5198   -1.6363    0.0086 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1538   -2.8242    0.7584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4071   -1.1429    0.7733 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5597   -0.3398    2.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1043    0.0505    2.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7006   -0.4705    1.2034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9849    0.1755    0.9106 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5298   -0.2625   -0.4254 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5256   -0.3345   -1.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2992   -1.1099   -1.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3137   -0.3951    0.0597 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6039    1.0426   -0.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6977    0.6075   -0.7580 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2206    2.0619   -0.7555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2744    0.2385   -2.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5212    1.0169   -2.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5720    0.8901   -1.3483 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.6925    0.2365   -1.8953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0842    0.0611   -0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7310    0.4760    0.3112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3518   -0.5359    1.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917   -0.3034    1.9533 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5512   -1.5192    2.4814 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6208    2.0216   -0.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7929    3.2323   -0.3257 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3877    1.4231   -1.5297 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4469   -0.6697    0.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8852   -0.1096    1.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3873    0.5180    1.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1626    1.9237    1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0343    1.4751   -1.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0177   -0.0402   -1.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2195   -0.8447    0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691    0.5766    0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0879   -0.0375   -1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0987   -1.4602   -1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0253   -2.2136   -0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4111   -3.6167    0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5885   -2.5209    1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9611   -3.2792    0.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8716   -2.0893    1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0980    0.5936    1.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8819   -0.9907    2.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0260    1.1523    2.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2048   -0.3263    3.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8676   -1.5571    1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9881    1.2858    0.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9239   -1.3089   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2850    0.6406   -1.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062   -0.9277   -2.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6922   -2.0937   -0.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3878   -1.3111   -1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6168    1.3582    0.1383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1005    1.7118    0.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4894    1.3403   -1.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1296    2.1405   -0.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6676    2.6451   -1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5059    2.5786    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5675    0.3929   -2.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5278   -0.8310   -2.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9010    0.6097   -3.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3475    2.0883   -2.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9521    1.8785   -1.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4645    0.2439   -1.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0287   -1.0076   -0.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8039    0.1477    0.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9037    1.4428    0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5047   -1.5714    0.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1169   -0.4138    2.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0560    0.4300    2.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8000   -2.2442    1.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1237    0.7489   -1.3369 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  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 13 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
  2 29  1  0
 29 30  2  0
 29 31  1  0
 16  8  1  0
 25 18  1  0
 16 11  1  0
 27 12  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  6
  7 43  1  0
  7 44  1  0
  7 45  1  0
  8 46  1  1
  9 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  1
 12 52  1  6
 13 53  1  1
 14 54  1  0
 14 55  1  0
 15 56  1  0
 15 57  1  0
 17 58  1  0
 17 59  1  0
 17 60  1  0
 19 61  1  0
 19 62  1  0
 19 63  1  0
 20 64  1  0
 20 65  1  0
 21 66  1  0
 21 67  1  0
 22 68  1  1
 23 69  1  0
 24 70  1  0
 24 71  1  0
 25 72  1  1
 26 73  1  0
 26 74  1  0
 27 75  1  1
 28 76  1  0
 31 77  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0       9.591  -7.616   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.591  -9.156   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.925  -6.846   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.925  -9.926   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.593  -9.926   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.259  -7.616   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.593  -6.846   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.926  -7.616   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.926  -9.156   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.259  -9.156   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.593  -5.306   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.724  -7.322   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.630  -6.076   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.259  -6.076   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0      13.593  -8.386   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0      14.926  -6.076   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0      16.260  -6.846   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.260  -5.306   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.260  -3.766   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      16.260  -8.386   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0      14.926  -4.536   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.260  -9.926   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.258  -9.926   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0      12.259 -10.696   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0      16.391  -2.521   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.724  -3.291   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.058  -2.521   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.392  -3.291   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      21.726  -2.521   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      23.059  -4.831   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      23.059  -3.291   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      24.393  -0.981   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      24.393  -2.521   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      25.727  -3.291   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      17.724  -4.831   0.000  0.00  0.00           C+0
HETATM   36  H   UNK     0      19.058  -4.061   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1   23    4                                                  
CONECT    3    1    6                                                       
CONECT    4    2   10                                                       
CONECT    5    9   10                                                       
CONECT    6    3   14    7   10                                             
CONECT    7    6   11   15    8                                             
CONECT    8    7   17   16    9                                             
CONECT    9    5    8   22                                                  
CONECT   10    4    5    6   24                                             
CONECT   11    7   21                                                       
CONECT   12   17   13                                                       
CONECT   13   12   35                                                       
CONECT   14    6                                                            
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17    8   12   18   20                                             
CONECT   18   17   35   21   19                                             
CONECT   19   18                                                            
CONECT   20   17                                                            
CONECT   21   11   18                                                       
CONECT   22    9                                                            
CONECT   23    2                                                            
CONECT   24   10                                                            
CONECT   25   26                                                            
CONECT   26   35   25   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   31                                                       
CONECT   30   31                                                            
CONECT   31   29   30   33                                                  
CONECT   32   33                                                            
CONECT   33   31   32   34                                                  
CONECT   34   33                                                            
CONECT   35   13   18   26   36                                             
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

COMPND    HMDB0000359
HETATM    1  C1  UNL     1       7.363   0.170   0.978  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.619   1.279   0.252  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.562   0.648  -0.665  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.589  -0.168   0.203  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.539  -0.807  -0.619  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.520  -1.636   0.009  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.154  -2.824   0.758  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.407  -1.143   0.773  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.560  -0.340   2.002  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.104   0.051   2.332  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.701  -0.471   1.203  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.985   0.175   0.911  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.530  -0.262  -0.425  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.526  -0.334  -1.519  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.299  -1.110  -1.089  1.00  0.00           C  
HETATM   16  C16 UNL     1       0.314  -0.395   0.060  1.00  0.00           C  
HETATM   17  C17 UNL     1       0.604   1.043  -0.185  1.00  0.00           C  
HETATM   18  C18 UNL     1      -3.698   0.607  -0.758  1.00  0.00           C  
HETATM   19  C19 UNL     1      -3.221   2.062  -0.755  1.00  0.00           C  
HETATM   20  C20 UNL     1      -4.274   0.238  -2.093  1.00  0.00           C  
HETATM   21  C21 UNL     1      -5.521   1.017  -2.410  1.00  0.00           C  
HETATM   22  C22 UNL     1      -6.572   0.890  -1.348  1.00  0.00           C  
HETATM   23  O1  UNL     1      -7.693   0.236  -1.895  1.00  0.00           O  
HETATM   24  C23 UNL     1      -6.084   0.061  -0.212  1.00  0.00           C  
HETATM   25  C24 UNL     1      -4.731   0.476   0.311  1.00  0.00           C  
HETATM   26  C25 UNL     1      -4.352  -0.536   1.372  1.00  0.00           C  
HETATM   27  C26 UNL     1      -2.992  -0.303   1.953  1.00  0.00           C  
HETATM   28  O2  UNL     1      -2.551  -1.519   2.481  1.00  0.00           O  
HETATM   29  C27 UNL     1       7.621   2.022  -0.542  1.00  0.00           C  
HETATM   30  O3  UNL     1       7.793   3.232  -0.326  1.00  0.00           O  
HETATM   31  O4  UNL     1       8.388   1.423  -1.530  1.00  0.00           O  
HETATM   32  H1  UNL     1       7.447  -0.670   0.263  1.00  0.00           H  
HETATM   33  H2  UNL     1       6.885  -0.110   1.922  1.00  0.00           H  
HETATM   34  H3  UNL     1       8.387   0.518   1.188  1.00  0.00           H  
HETATM   35  H4  UNL     1       6.163   1.924   1.000  1.00  0.00           H  
HETATM   36  H5  UNL     1       5.034   1.475  -1.165  1.00  0.00           H  
HETATM   37  H6  UNL     1       6.018  -0.040  -1.376  1.00  0.00           H  
HETATM   38  H7  UNL     1       5.220  -0.845   0.791  1.00  0.00           H  
HETATM   39  H8  UNL     1       4.169   0.577   0.903  1.00  0.00           H  
HETATM   40  H9  UNL     1       3.088  -0.037  -1.286  1.00  0.00           H  
HETATM   41  H10 UNL     1       4.099  -1.460  -1.365  1.00  0.00           H  
HETATM   42  H11 UNL     1       2.025  -2.214  -0.864  1.00  0.00           H  
HETATM   43  H12 UNL     1       2.411  -3.617   0.944  1.00  0.00           H  
HETATM   44  H13 UNL     1       3.589  -2.521   1.707  1.00  0.00           H  
HETATM   45  H14 UNL     1       3.961  -3.279   0.139  1.00  0.00           H  
HETATM   46  H15 UNL     1       0.872  -2.089   1.142  1.00  0.00           H  
HETATM   47  H16 UNL     1       2.098   0.594   1.962  1.00  0.00           H  
HETATM   48  H17 UNL     1       1.882  -0.991   2.859  1.00  0.00           H  
HETATM   49  H18 UNL     1      -0.026   1.152   2.368  1.00  0.00           H  
HETATM   50  H19 UNL     1      -0.205  -0.326   3.326  1.00  0.00           H  
HETATM   51  H20 UNL     1      -0.868  -1.557   1.364  1.00  0.00           H  
HETATM   52  H21 UNL     1      -1.988   1.286   0.993  1.00  0.00           H  
HETATM   53  H22 UNL     1      -2.924  -1.309  -0.267  1.00  0.00           H  
HETATM   54  H23 UNL     1      -1.285   0.641  -1.979  1.00  0.00           H  
HETATM   55  H24 UNL     1      -2.006  -0.928  -2.353  1.00  0.00           H  
HETATM   56  H25 UNL     1      -0.692  -2.094  -0.697  1.00  0.00           H  
HETATM   57  H26 UNL     1       0.388  -1.311  -1.922  1.00  0.00           H  
HETATM   58  H27 UNL     1       1.617   1.358   0.138  1.00  0.00           H  
HETATM   59  H28 UNL     1      -0.100   1.712   0.354  1.00  0.00           H  
HETATM   60  H29 UNL     1       0.489   1.340  -1.270  1.00  0.00           H  
HETATM   61  H30 UNL     1      -2.130   2.141  -0.854  1.00  0.00           H  
HETATM   62  H31 UNL     1      -3.668   2.645  -1.575  1.00  0.00           H  
HETATM   63  H32 UNL     1      -3.506   2.579   0.188  1.00  0.00           H  
HETATM   64  H33 UNL     1      -3.568   0.393  -2.926  1.00  0.00           H  
HETATM   65  H34 UNL     1      -4.528  -0.831  -2.078  1.00  0.00           H  
HETATM   66  H35 UNL     1      -5.901   0.610  -3.393  1.00  0.00           H  
HETATM   67  H36 UNL     1      -5.347   2.088  -2.589  1.00  0.00           H  
HETATM   68  H37 UNL     1      -6.952   1.878  -1.002  1.00  0.00           H  
HETATM   69  H38 UNL     1      -8.464   0.244  -1.301  1.00  0.00           H  
HETATM   70  H39 UNL     1      -6.029  -1.008  -0.490  1.00  0.00           H  
HETATM   71  H40 UNL     1      -6.804   0.148   0.627  1.00  0.00           H  
HETATM   72  H41 UNL     1      -4.904   1.443   0.869  1.00  0.00           H  
HETATM   73  H42 UNL     1      -4.505  -1.571   0.995  1.00  0.00           H  
HETATM   74  H43 UNL     1      -5.117  -0.414   2.191  1.00  0.00           H  
HETATM   75  H44 UNL     1      -3.056   0.430   2.784  1.00  0.00           H  
HETATM   76  H45 UNL     1      -2.800  -2.244   1.847  1.00  0.00           H  
HETATM   77  H46 UNL     1       9.124   0.749  -1.337  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3   29   35
CONECT    3    4   36   37
CONECT    4    5   38   39
CONECT    5    6   40   41
CONECT    6    7    8   42
CONECT    7   43   44   45
CONECT    8    9   16   46
CONECT    9   10   47   48
CONECT   10   11   49   50
CONECT   11   12   16   51
CONECT   12   13   27   52
CONECT   13   14   18   53
CONECT   14   15   54   55
CONECT   15   16   56   57
CONECT   16   17
CONECT   17   58   59   60
CONECT   18   19   20   25
CONECT   19   61   62   63
CONECT   20   21   64   65
CONECT   21   22   66   67
CONECT   22   23   24   68
CONECT   23   69
CONECT   24   25   70   71
CONECT   25   26   72
CONECT   26   27   73   74
CONECT   27   28   75
CONECT   28   76
CONECT   29   30   30   31
CONECT   31   77
END

HMDB0000359
     RDKit          3D
3alpha,7alpha-Dihydroxycoprostanic acid
 77 80  0  0  0  0  0  0  0  0999 V2000
    7.3633    0.1703    0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6191    1.2787    0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5621    0.6484   -0.6652 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5887   -0.1682    0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5388   -0.8066   -0.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5198   -1.6363    0.0086 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1538   -2.8242    0.7584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4071   -1.1429    0.7733 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5597   -0.3398    2.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1043    0.0505    2.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7006   -0.4705    1.2034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9849    0.1755    0.9106 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5298   -0.2625   -0.4254 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5256   -0.3345   -1.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2992   -1.1099   -1.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3137   -0.3951    0.0597 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6039    1.0426   -0.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6977    0.6075   -0.7580 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2206    2.0619   -0.7555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2744    0.2385   -2.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5212    1.0169   -2.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5720    0.8901   -1.3483 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.6925    0.2365   -1.8953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0842    0.0611   -0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7310    0.4760    0.3112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3518   -0.5359    1.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917   -0.3034    1.9533 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5512   -1.5192    2.4814 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6208    2.0216   -0.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7929    3.2323   -0.3257 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3877    1.4231   -1.5297 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4469   -0.6697    0.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8852   -0.1096    1.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3873    0.5180    1.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1626    1.9237    1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0343    1.4751   -1.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0177   -0.0402   -1.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2195   -0.8447    0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691    0.5766    0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0879   -0.0375   -1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0987   -1.4602   -1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0253   -2.2136   -0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4111   -3.6167    0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5885   -2.5209    1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9611   -3.2792    0.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8716   -2.0893    1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0980    0.5936    1.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8819   -0.9907    2.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0260    1.1523    2.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2048   -0.3263    3.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8676   -1.5571    1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9881    1.2858    0.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9239   -1.3089   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2850    0.6406   -1.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062   -0.9277   -2.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6922   -2.0937   -0.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3878   -1.3111   -1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6168    1.3582    0.1383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1005    1.7118    0.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4894    1.3403   -1.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1296    2.1405   -0.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6676    2.6451   -1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5059    2.5786    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5675    0.3929   -2.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5278   -0.8310   -2.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9010    0.6097   -3.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3475    2.0883   -2.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9521    1.8785   -1.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4645    0.2439   -1.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0287   -1.0076   -0.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8039    0.1477    0.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9037    1.4428    0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5047   -1.5714    0.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1169   -0.4138    2.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0560    0.4300    2.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8000   -2.2442    1.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1237    0.7489   -1.3369 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  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 13 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
  2 29  1  0
 29 30  2  0
 29 31  1  0
 16  8  1  0
 25 18  1  0
 16 11  1  0
 27 12  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  6
  7 43  1  0
  7 44  1  0
  7 45  1  0
  8 46  1  1
  9 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  1
 12 52  1  6
 13 53  1  1
 14 54  1  0
 14 55  1  0
 15 56  1  0
 15 57  1  0
 17 58  1  0
 17 59  1  0
 17 60  1  0
 19 61  1  0
 19 62  1  0
 19 63  1  0
 20 64  1  0
 20 65  1  0
 21 66  1  0
 21 67  1  0
 22 68  1  1
 23 69  1  0
 24 70  1  0
 24 71  1  0
 25 72  1  1
 26 73  1  0
 26 74  1  0
 27 75  1  1
 28 76  1  0
 31 77  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3alpha,7alpha-Dihydroxy-5beta-cholestanate	ChEBI
3alpha,7alpha-Dihydroxy-5beta-cholestanic acid	ChEBI
3alpha,7alpha-Dihydroxy-5beta-cholestanoate	ChEBI
3alpha,7alpha-Dihydroxy-5beta-cholestanoic acid	ChEBI
3a,7a-Dihydroxy-5b-cholestanate	Generator
3a,7a-Dihydroxy-5b-cholestanic acid	Generator
3Α,7α-dihydroxy-5β-cholestanate	Generator
3Α,7α-dihydroxy-5β-cholestanic acid	Generator
3a,7a-Dihydroxy-5b-cholestanoate	Generator
3a,7a-Dihydroxy-5b-cholestanoic acid	Generator
3Α,7α-dihydroxy-5β-cholestanoate	Generator
3Α,7α-dihydroxy-5β-cholestanoic acid	Generator
3a,7a-Dihydroxycoprostanate	Generator
3a,7a-Dihydroxycoprostanic acid	Generator
3alpha,7alpha-Dihydroxycoprostanate	Generator
3Α,7α-dihydroxycoprostanate	Generator
3Α,7α-dihydroxycoprostanic acid	Generator
3a,7a-Dihydroxy-5b-cholestan-26-Oate	HMDB
3a,7a-Dihydroxy-5b-cholestan-26-Oic acid	HMDB
3alpha,7alpha-Dihydroxy-5beta-cholestan-26-Oate	HMDB
3Α,7α-dihydroxy-5β-cholestan-26-Oate	HMDB
3Α,7α-dihydroxy-5β-cholestan-26-Oic acid	HMDB
(3Α,5β,7α)-3,7-dihydroxycholestan-26-Oic acid	HMDB
(3a,5b,7a)-3,7-Dihydroxycholestan-26-Oic acid	HMDB
(3alpha,5beta,7alpha)-3,7-Dihydroxycholestan-26-Oic acid	HMDB
3Α,7α-hydroxy-5β-cholestan-26-Oic acid	HMDB
3a,7a-Hydroxy-5β-cholestan-26-Oic acid	HMDB
3alpha,7alpha-Hydroxy-5β-cholestan-26-Oic acid	HMDB
3a,7a-Hydroxy-5b-cholestan-26-Oate	HMDB
3a,7a-Hydroxy-5b-cholestan-26-Oic acid	HMDB
3alpha,7alpha-Dihydroxy-5beta-cholestan-26-Oic acid	HMDB
3alpha,7alpha-Dihydroxycoprostanic acid	HMDB

Chemical Formula

C₂₇H₄₆O₄

Average Molecular Weight

434.661

Monoisotopic Molecular Weight

434.339609961

IUPAC Name

(6R)-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid

Traditional Name

(6R)-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid

CAS Registry Number

17974-66-2

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O

InChI Identifier

InChI=1S/C27H46O4/c1-16(6-5-7-17(2)25(30)31)20-8-9-21-24-22(11-13-27(20,21)4)26(3)12-10-19(28)14-18(26)15-23(24)29/h16-24,28-29H,5-15H2,1-4H3,(H,30,31)/t16-,17?,18+,19-,20-,21+,22+,23-,24+,26+,27-/m1/s1

InChI Key

ITZYGDKGRKKBSN-HKFUITGCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Dihydroxy bile acid, alcohol, or derivatives
Steroid acid
3-hydroxysteroid
7-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
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

3alpha-hydroxy steroid (CHEBI:16577 )
dihydroxy monocarboxylic acid (CHEBI:16577 )
7alpha-hydroxy steroid (CHEBI:16577 )
cholestanoid (CHEBI:16577 )
C27 bile acids, alcohols, and derivatives (LMST04030066 )

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 2427795)
Bile (PMID: 31643938)

Excreta

Biofluid or Excreta

Feces (PMID: 26848182)
Urine (PMID: 1112456)

Cellular substructure

Extracellular (HMDB: HMDB0000359)

Organ

Source

Exogenous

Exogenous (HMDB: HMDB0000359)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000359)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Bile Acid Biosynthesis (PathBank: SMP0087329)

Disease pathway

27-Hydroxylase Deficiency (PathBank: SMP0120652)
Cerebrotendinous Xanthomatosis (CTX) (PathBank: SMP0120683)
Familial Hypercholanemia (FHCA) (PathBank: SMP0120697)
Zellweger Syndrome (PathBank: SMP0120715)
Congenital Bile Acid Synthesis Defect Type II (PathBank: SMP0120687)
Congenital Bile Acid Synthesis Defect Type III (PathBank: SMP0120688)

Role

Industrial application

Pharmaceutical industry

Biomarker

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	0.0044 g/L	ALOGPS
logP	4.02	ALOGPS
logP	5.15	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.83	ChemAxon
pKa (Strongest Basic)	-0.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.05 m³·mol⁻¹	ChemAxon
Polarizability	52.21 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	211.212	32859911
AllCCS	[M-H]-	206.022	32859911
DeepCCS	[M-2H]-	251.435	30932474
DeepCCS	[M+Na]+	225.451	30932474
AllCCS	[M+H]+	211.2	32859911
AllCCS	[M+H-H2O]+	209.4	32859911
AllCCS	[M+NH4]+	212.9	32859911
AllCCS	[M+Na]+	213.3	32859911
AllCCS	[M-H]-	206.0	32859911
AllCCS	[M+Na-2H]-	208.2	32859911
AllCCS	[M+HCOO]-	210.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3alpha,7alpha-Dihydroxycoprostanic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O	3711.5	Standard polar	33892256
3alpha,7alpha-Dihydroxycoprostanic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O	3535.3	Standard non polar	33892256
3alpha,7alpha-Dihydroxycoprostanic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O	3716.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3alpha,7alpha-Dihydroxycoprostanic acid,1TMS,isomer #1	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C)C(=O)O	3582.0	Semi standard non polar	33892256
3alpha,7alpha-Dihydroxycoprostanic acid,1TMS,isomer #2	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O)C(=O)O	3629.0	Semi standard non polar	33892256
3alpha,7alpha-Dihydroxycoprostanic acid,1TMS,isomer #3	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O)C(=O)O[Si](C)(C)C	3539.4	Semi standard non polar	33892256
3alpha,7alpha-Dihydroxycoprostanic acid,2TMS,isomer #1	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C)C(=O)O	3511.6	Semi standard non polar	33892256
3alpha,7alpha-Dihydroxycoprostanic acid,2TMS,isomer #2	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C)C(=O)O[Si](C)(C)C	3459.4	Semi standard non polar	33892256
3alpha,7alpha-Dihydroxycoprostanic acid,2TMS,isomer #3	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O)C(=O)O[Si](C)(C)C	3535.9	Semi standard non polar	33892256
3alpha,7alpha-Dihydroxycoprostanic acid,3TMS,isomer #1	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C)C(=O)O[Si](C)(C)C	3438.2	Semi standard non polar	33892256
3alpha,7alpha-Dihydroxycoprostanic acid,1TBDMS,isomer #1	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C)C(=O)O	3799.9	Semi standard non polar	33892256
3alpha,7alpha-Dihydroxycoprostanic acid,1TBDMS,isomer #2	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O)C(=O)O	3847.8	Semi standard non polar	33892256
3alpha,7alpha-Dihydroxycoprostanic acid,1TBDMS,isomer #3	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O)C(=O)O[Si](C)(C)C(C)(C)C	3801.3	Semi standard non polar	33892256
3alpha,7alpha-Dihydroxycoprostanic acid,2TBDMS,isomer #1	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C)C(=O)O	3935.3	Semi standard non polar	33892256
3alpha,7alpha-Dihydroxycoprostanic acid,2TBDMS,isomer #2	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3932.4	Semi standard non polar	33892256
3alpha,7alpha-Dihydroxycoprostanic acid,2TBDMS,isomer #3	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O)C(=O)O[Si](C)(C)C(C)(C)C	4022.2	Semi standard non polar	33892256
3alpha,7alpha-Dihydroxycoprostanic acid,3TBDMS,isomer #1	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	4139.3	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 - 3alpha,7alpha-Dihydroxycoprostanic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid 10V, Positive-QTOF	splash10-014s-0007900000-55bf6ba08fdb23cc5f37	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid 20V, Positive-QTOF	splash10-01ba-0009200000-3864d6012d9e0f3baf02	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid 40V, Positive-QTOF	splash10-06di-1019000000-1d984e3a244a1acc4fd5	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid 10V, Negative-QTOF	splash10-001i-0001900000-8b656f3d458df7baa276	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid 20V, Negative-QTOF	splash10-00sr-0007900000-8c41fc1f2328cf805012	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid 40V, Negative-QTOF	splash10-05fr-6009200000-226e124be38dd986fd54	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid 10V, Negative-QTOF	splash10-001i-0000900000-7d30a0f812b7e3c2a316	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid 20V, Negative-QTOF	splash10-001i-0003900000-0d1d8d80f2d02b013f95	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid 40V, Negative-QTOF	splash10-001i-1001900000-5768154ed48ccb53ffa4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid 10V, Positive-QTOF	splash10-00ks-1216900000-ef73c5639ce04b841fe1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid 20V, Positive-QTOF	splash10-00xs-2139100000-c7d71db3ab32237bfc53	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,7alpha-Dihydroxycoprostanic acid 40V, Positive-QTOF	splash10-052k-9670000000-86665221276c4d7674c4	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Feces

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Primary bile acid biosynthesis	Not Available
Congenital Bile Acid Synthesis Defect Type II		Not Available
Congenital Bile Acid Synthesis Defect Type III		Not Available
Familial Hypercholanemia (FHCA)		Not Available
Zellweger Syndrome		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.403 - 0.842 uM	Children (1 - 13 years old)	Male	Classicle Refsum's disease	2427795	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Inflammatory bowel disease	26848182	details

Associated Disorders and Diseases

Disease References

Refsum's disease
Poll-The BT, Saudubray JM, Ogier H, Schutgens RB, Wanders RJ, Schrakamp G, van den Bosch H, Trijbels JM, Poulos A, Moser HW, et al.: Infantile Refsum's disease: biochemical findings suggesting multiple peroxisomal dysfunction. J Inherit Metab Dis. 1986;9(2):169-74. [PubMed:2427795 ]
Inflammatory bowel disease
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]

Associated OMIM IDs

266500 (Refsum's disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021979

KNApSAcK ID

Not Available

Chemspider ID

4447327

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5348

PubChem Compound

5284239

PDB ID

Not Available

ChEBI ID

16577

Food Biomarker Ontology

Not Available

VMH ID

DHCHOLESTANATE

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Hanson, Russell Floyd. Isolation, identification, formation, and metabolism of 3a, 7a-hydroxy-5b-cholestan-26-oic acid in man. (1972), 73 pp. CAN 78:27152 AN 1973:27152

Material Safety Data Sheet (MSDS)

Not Available

General References

Alme B, Bremmelgaard A, Sjovall J, Thomassen P: Analysis of metabolic profiles of bile acids in urine using a lipophilic anion exchanger and computerized gas-liquid chromatorgaphy-mass spectrometry. J Lipid Res. 1977 May;18(3):339-62. [PubMed:864325 ]

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Aldehyde dehydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: ALDH2
Uniprot ID:: P05091
Molecular weight:: 56380.93

Enzyme Details

2. Bile acid-CoA:amino acid N-acyltransferase

General function:: Involved in thiolester hydrolase activity
Specific function:: Involved in bile acid metabolism. In liver hepatocytes catalyzes the second step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi. The major components of bile are cholic acid and chenodeoxycholic acid. In a first step the bile acids are converted to an acyl-CoA thioester, either in peroxisomes (primary bile acids deriving from the cholesterol pathway), or cytoplasmic at the endoplasmic reticulum (secondary bile acids). May catalyze the conjugation of primary or secondary bile acids, or both. The conjugation increases the detergent properties of bile acids in the intestine, which facilitates lipid and fat-soluble vitamin absorption. In turn, bile acids are deconjugated by bacteria in the intestine and are recycled back to the liver for reconjugation (secondary bile acids). May also act as an acyl-CoA thioesterase that regulates intracellular levels of free fatty acids. In vitro, catalyzes the hydrolysis of long- and very long-chain saturated acyl-CoAs to the free fatty acid and coenzyme A (CoASH), and conjugates glycine to these acyl-CoAs.
Gene Name:: BAAT
Uniprot ID:: Q14032
Molecular weight:: 46298.865

Enzyme Details

3. Bile acyl-CoA synthetase

General function:: Involved in catalytic activity
Specific function:: Acyl-CoA synthetase involved in bile acid metabolism. Proposed to catalyze the first step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi by activating them to their CoA thioesters. Seems to activate secondary bile acids entering the liver from the enterohepatic circulation. In vitro, also activates 3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestanate (THCA), the C27 precursor of cholic acid deriving from the de novo synthesis from cholesterol.
Gene Name:: SLC27A5
Uniprot ID:: Q9Y2P5
Molecular weight:: 75384.375

Enzyme Details

4. Gastrotropin

General function:: Involved in binding
Specific function:: Ileal protein which stimulates gastric acid and pepsinogen secretion. Seems to be able to bind to bile salts and bilirubins. Isoform 2 is essential for the survival of colon cancer cells to bile acid-induced apoptosis
Gene Name:: FABP6
Uniprot ID:: P51161
Molecular weight:: 14371.2

References

Kurz M, Brachvogel V, Matter H, Stengelin S, Thuring H, Kramer W: Insights into the bile acid transportation system: the human ileal lipid-binding protein-cholyltaurine complex and its comparison with homologous structures. Proteins. 2003 Feb 1;50(2):312-28. [PubMed:12486725 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1B3

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
Gene Name:: SLCO1B3
Uniprot ID:: Q9NPD5
Molecular weight:: 77402.2

Enzyme Details

2. Solute carrier organic anion transporter family member 1B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:: SLCO1B1
Uniprot ID:: Q9Y6L6
Molecular weight:: 76448.0

References

Michalski C, Cui Y, Nies AT, Nuessler AK, Neuhaus P, Zanger UM, Klein K, Eichelbaum M, Keppler D, Konig J: A naturally occurring mutation in the SLC21A6 gene causing impaired membrane localization of the hepatocyte uptake transporter. J Biol Chem. 2002 Nov 8;277(45):43058-63. Epub 2002 Aug 23. [PubMed:12196548 ]

Enzyme Details

3. Canalicular multispecific organic anion transporter 2

General function:: Involved in ATP binding
Specific function:: May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:: ABCC3
Uniprot ID:: O15438
Molecular weight:: 169341.1

Enzyme Details

4. Bile salt export pump

General function:: Involved in ATP binding
Specific function:: Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:: ABCB11
Uniprot ID:: O95342
Molecular weight:: 146405.8

Enzyme Details

5. Ileal sodium/bile acid cotransporter

General function:: Involved in bile acid:sodium symporter activity
Specific function:: Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism
Gene Name:: SLC10A2
Uniprot ID:: Q12908
Molecular weight:: 37697.4

References

Kramer W, Girbig F, Glombik H, Corsiero D, Stengelin S, Weyland C: Identification of a ligand-binding site in the Na+/bile acid cotransporting protein from rabbit ileum. J Biol Chem. 2001 Sep 21;276(38):36020-7. Epub 2001 Jul 10. [PubMed:11447228 ]

Enzyme Details

6. Sodium/bile acid cotransporter

General function:: Involved in bile acid:sodium symporter activity
Specific function:: The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium.
Gene Name:: SLC10A1
Uniprot ID:: Q14973
Molecular weight:: 38118.64

Enzyme Details

7. Solute carrier organic anion transporter family member 1A2

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:: SLCO1A2
Uniprot ID:: P46721
Molecular weight:: 74144.1

Enzyme Details

8. Solute carrier organic anion transporter family member 4A1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate
Gene Name:: SLCO4A1
Uniprot ID:: Q96BD0
Molecular weight:: 77192.5

Only showing the first 10 proteins. There are 12 proteins in total.

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Showing metabocard for 3alpha,7alpha-Dihydroxycoprostanic acid (HMDB0000359)

MOL for HMDB0000359 (3alpha,7alpha-Dihydroxycoprostanic acid)

3D MOL for HMDB0000359 (3alpha,7alpha-Dihydroxycoprostanic acid)

3D SDF for HMDB0000359 (3alpha,7alpha-Dihydroxycoprostanic acid)

3D-SDF for HMDB0000359 (3alpha,7alpha-Dihydroxycoprostanic acid)

PDB for HMDB0000359 (3alpha,7alpha-Dihydroxycoprostanic acid)

3D PDB for HMDB0000359 (3alpha,7alpha-Dihydroxycoprostanic acid)

SMILES for HMDB0000359 (3alpha,7alpha-Dihydroxycoprostanic acid)

INCHI for HMDB0000359 (3alpha,7alpha-Dihydroxycoprostanic acid)

Structure for HMDB0000359 (3alpha,7alpha-Dihydroxycoprostanic acid)

3D Structure for HMDB0000359 (3alpha,7alpha-Dihydroxycoprostanic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Transporters

References

References