MiMeDB: Showing metabocard for Deoxycholylisoleucine (MMDBc0057261)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-11-10 23:38:17 UTC

Update Date

2024-04-30 20:57:05 UTC

Metabolite ID

MMDBc0057261

Metabolite Identification

Common Name

Deoxycholylisoleucine

Description

Deoxycholylisoleucine belongs to a class of molecules known as bile acid-amino acid conjugates. These are bile acid conjugates that consist of a primary bile acid such as cholic acid, doxycholic acid and chenodeoxycholic acid, conjugated to an amino acid. Deoxycholylisoleucine consists of the bile acid deoxycholic acid conjugated to the amino acid Isoleucine conjugated at the C24 acyl site.Bile acids play an important role in regulating various physiological systems, such as fat digestion, cholesterol metabolism, vitamin absorption, liver function, and enterohepatic circulation through their combined signaling, detergent, and antimicrobial mechanisms (PMID: 34127070 ). Bile acids also act as detergents in the gut and support the absorption of fats through the intestinal membrane. These same properties allow for the disruption of bacterial membranes, thereby allowing them to serve a bacteriocidal or bacteriostatic function. In humans (and other mammals) bile acids are normally conjugated with the amino acids glycine and taurine by the liver. This conjugation catalyzed by two liver enzymes, bile acid CoA ligase (BAL) and bile acid CoA: amino acid N-acyltransferase (BAT). Glycine and taurine bound BAs are also referred to as bile salts due to their decreased pKa and complete ionization resulting in these compounds being present as anions in vivo. Unlike glycine and taurine-conjugated bile acids, these recently discovered bile acids, such as Deoxycholylisoleucine, are produced by the gut microbiota, making them secondary bile acids (PMID: 32103176 ) or microbially conjugated bile acids (MCBAs) (PMID: 34127070 ). Evidence suggests that these bile acid-amino acid conjugates are produced by microbes belonging to Clostridia species (PMID: 32103176 ). These unusual bile acid-amino acid conjugates are found in higher frequency in patients with inflammatory bowel disease (IBD), cystic fibrosis (CF) and in infants (PMID: 32103176 ). Deoxycholylisoleucine appears to act as an agonist for the farnesoid X receptor (FXR) and it can also lead to reduced expression of bile acid synthesis genes (PMID: 32103176 ). It currently appears that microbially conjugated bile acids (MCBAs) or amino acid-bile acid conjugates are only conjugated to cholic acid, deoxycholic acid and chenodeoxycholic acid (PMID: 34127070 ). It has been estimated that if microbial conjugation of bile acids is very promiscuous and occurs for all potential oxidized, epimerized, and dehydroxylated states of each hydroxyl group present on cholic acid (C3, C7, C12) in addition to ring orientation, the total number of potential human bile acid conjugates could be over 2800 (PMID: 34127070 ).

Structure

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


  Mrv1652308302121562D          

 36 39  0  0  0  0            999 V2000
    9.1168   -3.4686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4023   -3.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6879   -3.4686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4023   -2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6879   -1.8186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9734   -2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9734   -3.0561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2589   -1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5445   -2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8300   -1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8300   -0.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1155   -2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0293   -3.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2223   -3.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8098   -2.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0028   -2.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4508   -2.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6438   -2.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3889   -1.9941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4181   -1.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -1.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4800   -0.8664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1210   -0.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860   -0.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9409   -1.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4930   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7479   -1.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2999   -0.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1069   -1.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6589   -0.4978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3618   -1.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9749   -1.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1168   -1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1168   -0.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8313   -2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5458   -1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 12 31  1  0  0  0  0
 15 31  1  0  0  0  0
 31 32  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END

HMDB0242416
     RDKit          3D
Deoxycholylisoleucine
 87 90  0  0  0  0  0  0  0  0999 V2000
    7.0982    3.1964   -1.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6376    1.7828   -1.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6499    0.7597   -1.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1911   -0.6234   -1.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2224    0.9771    0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2522   -0.0220    0.8423 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9977    0.2958    1.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7216    1.5356    1.5302 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0028   -0.7400    1.8057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7850   -0.1228    2.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7190   -1.0267    2.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3516   -1.9752    3.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063   -1.6952    1.9757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3279   -2.6282    0.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0621   -3.0040    0.2636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4765   -1.6068    0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6650   -1.2567   -0.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5632   -2.3847   -1.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8595   -2.0017   -1.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3188   -0.5974   -1.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0090   -0.1123   -2.9080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8371    1.0798   -2.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3347    1.6590   -3.7148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1395    2.1063   -1.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0911    1.6556   -0.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2996    0.4407   -1.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4872    0.8553   -2.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4967   -0.1400   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7397    0.8768    0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805    0.4369    1.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5298    0.6574    0.0749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4082   -1.0310    1.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6282   -1.4120    2.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3646    0.8884    1.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3449    0.0208    2.2908 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4916    1.6906    1.3368 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0810    3.2772   -1.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8155    3.8953   -1.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0057    3.4437   -0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6200    1.7345   -0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7623    1.7249   -2.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7470    0.8609   -1.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.1634   -0.5368   -1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5309   -1.2610   -1.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7710    1.9793    0.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5229   -1.0180    0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8035   -1.3346    0.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5534   -1.4081    2.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2012    0.3699    3.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5753   -2.7241    4.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8357   -3.5103    1.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8620   -3.5856   -0.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6908   -3.4820    1.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5596   -1.1330   -0.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3243   -0.8231   -1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918   -3.0076   -1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6633   -3.0723   -0.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6441   -2.6916   -1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9049   -2.2863   -2.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1134   -0.5341   -0.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3489    0.0288   -3.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7322   -0.9246   -3.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7452    0.7172   -1.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6800    2.5773   -3.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7942    2.9308   -2.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9335    2.6299   -1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3425    2.4868   -0.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4647    1.5020    0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3816    0.0641   -3.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0511    1.6755   -2.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5137    1.3155   -2.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5969    1.7736   -0.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3639    1.2469    1.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1462    1.0708    2.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1738    1.5710    0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2312   -1.8382    3.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2220   -2.2222    1.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1889   -0.5215    2.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4169    1.3703    1.5619 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
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 21 22  1  0
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 22 24  1  0
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 25 26  1  0
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 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
  5 34  1  0
 34 35  2  0
 34 36  1  0
 32 13  1  0
 32 16  1  0
 28 17  1  0
 26 20  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  0
  2 41  1  0
  3 42  1  0
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  9 48  1  0
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 31 83  1  0
 33 84  1  0
 33 85  1  0
 33 86  1  0
 36 87  1  0
M  END


  Mrv1652308302121562D          

 36 39  0  0  0  0            999 V2000
    9.1168   -3.4686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4023   -3.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6879   -3.4686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4023   -2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6879   -1.8186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9734   -2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9734   -3.0561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2589   -1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5445   -2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8300   -1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8300   -0.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1155   -2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0293   -3.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2223   -3.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8098   -2.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0028   -2.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4508   -2.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6438   -2.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3889   -1.9941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4181   -1.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -1.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4800   -0.8664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1210   -0.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860   -0.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9409   -1.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4930   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7479   -1.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2999   -0.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1069   -1.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6589   -0.4978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3618   -1.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9749   -1.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1168   -1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1168   -0.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8313   -2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5458   -1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 12 31  1  0  0  0  0
 15 31  1  0  0  0  0
 31 32  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0057261

> <DATABASE_NAME>
MIME

> <SMILES>
CCC(C)C(NC(=O)CCC(C)C1CCC2C3CCC4CC(O)CCC4(C)C3CC(O)C12C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H51NO5/c1-6-17(2)27(28(35)36)31-26(34)12-7-18(3)22-10-11-23-21-9-8-19-15-20(32)13-14-29(19,4)24(21)16-25(33)30(22,23)5/h17-25,27,32-33H,6-16H2,1-5H3,(H,31,34)(H,35,36)

> <INCHI_KEY>
QTMPUVRWTSAYOC-UHFFFAOYSA-N

> <FORMULA>
C30H51NO5

> <MOLECULAR_WEIGHT>
505.74

> <EXACT_MASS>
505.376723746

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
59.52018361954015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)-3-methylpentanoic acid

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
4.586804142666667

> <ALOGPS_LOGS>
-5.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.391194918179025

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.973697886200414

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2488955351276677

> <JCHEM_POLAR_SURFACE_AREA>
106.86000000000001

> <JCHEM_REFRACTIVITY>
140.0908

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.97e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)-3-methylpentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242416
     RDKit          3D
Deoxycholylisoleucine
 87 90  0  0  0  0  0  0  0  0999 V2000
    7.0982    3.1964   -1.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6376    1.7828   -1.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6499    0.7597   -1.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1911   -0.6234   -1.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2224    0.9771    0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2522   -0.0220    0.8423 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9977    0.2958    1.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7216    1.5356    1.5302 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0028   -0.7400    1.8057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7850   -0.1228    2.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7190   -1.0267    2.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3516   -1.9752    3.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063   -1.6952    1.9757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3279   -2.6282    0.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0621   -3.0040    0.2636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4765   -1.6068    0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6650   -1.2567   -0.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5632   -2.3847   -1.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8595   -2.0017   -1.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3188   -0.5974   -1.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0090   -0.1123   -2.9080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8371    1.0798   -2.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3347    1.6590   -3.7148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1395    2.1063   -1.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0911    1.6556   -0.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2996    0.4407   -1.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4872    0.8553   -2.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4967   -0.1400   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7397    0.8768    0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805    0.4369    1.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5298    0.6574    0.0749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4082   -1.0310    1.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6282   -1.4120    2.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3646    0.8884    1.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3449    0.0208    2.2908 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4916    1.6906    1.3368 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0810    3.2772   -1.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8155    3.8953   -1.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0057    3.4437   -0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6200    1.7345   -0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7623    1.7249   -2.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7470    0.8609   -1.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4015   -1.1592   -0.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1634   -0.5368   -1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5309   -1.2610   -1.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7710    1.9793    0.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5229   -1.0180    0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8035   -1.3346    0.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5534   -1.4081    2.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4642    0.7880    1.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2012    0.3699    3.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957   -0.3749    3.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5753   -2.7241    4.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1784   -2.5611    3.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6340   -1.4565    4.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6493   -2.5371    2.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8357   -3.5103    1.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8047   -2.1159    0.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8620   -3.5856   -0.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6908   -3.4820    1.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5596   -1.1330   -0.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3243   -0.8231   -1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918   -3.0076   -1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6633   -3.0723   -0.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6441   -2.6916   -1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9049   -2.2863   -2.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1134   -0.5341   -0.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3489    0.0288   -3.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7322   -0.9246   -3.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7452    0.7172   -1.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6800    2.5773   -3.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7942    2.9308   -2.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9335    2.6299   -1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3425    2.4868   -0.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4647    1.5020    0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3816    0.0641   -3.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0511    1.6755   -2.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5137    1.3155   -2.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2958   -0.5574    0.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5969    1.7736   -0.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3639    1.2469    1.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1462    1.0708    2.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1738    1.5710    0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2312   -1.8382    3.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2220   -2.2222    1.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1889   -0.5215    2.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4169    1.3703    1.5619 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
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 17 18  1  0
 18 19  1  0
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 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
  5 34  1  0
 34 35  2  0
 34 36  1  0
 32 13  1  0
 32 16  1  0
 28 17  1  0
 26 20  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  0
  2 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
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  5 46  1  0
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  9 48  1  0
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 10 50  1  0
 10 51  1  0
 11 52  1  0
 12 53  1  0
 12 54  1  0
 12 55  1  0
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 15 59  1  0
 15 60  1  0
 16 61  1  0
 17 62  1  0
 18 63  1  0
 18 64  1  0
 19 65  1  0
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 21 68  1  0
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 22 70  1  0
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 24 72  1  0
 24 73  1  0
 25 74  1  0
 25 75  1  0
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 30 82  1  0
 31 83  1  0
 33 84  1  0
 33 85  1  0
 33 86  1  0
 36 87  1  0
M  END

HEADER    PROTEIN                                 30-AUG-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-AUG-21         0                                  
HETATM    1  O   UNK     0      17.018  -6.475   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      15.684  -5.705   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      14.351  -6.475   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      15.684  -4.165   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      14.351  -3.395   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      13.017  -4.165   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.017  -5.705   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.683  -3.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.350  -4.165   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.016  -3.395   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.016  -1.855   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.682  -4.165   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.521  -5.696   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.015  -6.016   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.245  -4.683   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.739  -4.363   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.708  -5.507   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.202  -5.187   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.726  -3.722   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.780  -3.402   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.256  -1.937   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.763  -1.617   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.226  -0.793   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.281  -1.113   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.756  -2.578   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.787  -1.433   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.263  -2.898   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.293  -1.754   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.800  -2.074   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.830  -0.929   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.275  -3.538   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.420  -2.508   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      17.018  -3.395   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      17.018  -1.855   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      18.352  -4.165   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      19.685  -3.395   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   31                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   31                                                  
CONECT   16   15   17   27                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   19   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   16   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   12   15   32                                             
CONECT   32   31                                                            
CONECT   33    4   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

COMPND    HMDB0242416
HETATM    1  C1  UNL     1       7.098   3.196  -1.220  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.638   1.783  -1.440  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.650   0.760  -1.002  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.191  -0.623  -1.224  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.222   0.977   0.433  1.00  0.00           C  
HETATM    6  N1  UNL     1       5.252  -0.022   0.842  1.00  0.00           N  
HETATM    7  C6  UNL     1       3.998   0.296   1.391  1.00  0.00           C  
HETATM    8  O1  UNL     1       3.722   1.536   1.530  1.00  0.00           O  
HETATM    9  C7  UNL     1       3.003  -0.740   1.806  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.785  -0.123   2.420  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.719  -1.027   2.868  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.352  -1.975   3.917  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.206  -1.695   1.976  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.328  -2.628   0.901  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.062  -3.004   0.264  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.477  -1.607   0.016  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.665  -1.257  -0.733  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.563  -2.385  -1.158  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.859  -2.002  -1.729  1.00  0.00           C  
HETATM   20  C18 UNL     1      -5.319  -0.597  -1.653  1.00  0.00           C  
HETATM   21  C19 UNL     1      -6.009  -0.112  -2.908  1.00  0.00           C  
HETATM   22  C20 UNL     1      -6.837   1.080  -2.546  1.00  0.00           C  
HETATM   23  O2  UNL     1      -7.335   1.659  -3.715  1.00  0.00           O  
HETATM   24  C21 UNL     1      -6.140   2.106  -1.738  1.00  0.00           C  
HETATM   25  C22 UNL     1      -5.091   1.656  -0.803  1.00  0.00           C  
HETATM   26  C23 UNL     1      -4.300   0.441  -1.275  1.00  0.00           C  
HETATM   27  C24 UNL     1      -3.487   0.855  -2.447  1.00  0.00           C  
HETATM   28  C25 UNL     1      -3.497  -0.140  -0.132  1.00  0.00           C  
HETATM   29  C26 UNL     1      -2.740   0.877   0.637  1.00  0.00           C  
HETATM   30  C27 UNL     1      -1.380   0.437   1.159  1.00  0.00           C  
HETATM   31  O3  UNL     1      -0.530   0.657   0.075  1.00  0.00           O  
HETATM   32  C28 UNL     1      -1.408  -1.031   1.445  1.00  0.00           C  
HETATM   33  C29 UNL     1      -2.628  -1.412   2.272  1.00  0.00           C  
HETATM   34  C30 UNL     1       7.365   0.888   1.370  1.00  0.00           C  
HETATM   35  O4  UNL     1       7.345   0.021   2.291  1.00  0.00           O  
HETATM   36  O5  UNL     1       8.492   1.691   1.337  1.00  0.00           O  
HETATM   37  H1  UNL     1       6.081   3.277  -1.659  1.00  0.00           H  
HETATM   38  H2  UNL     1       7.815   3.895  -1.738  1.00  0.00           H  
HETATM   39  H3  UNL     1       7.006   3.444  -0.144  1.00  0.00           H  
HETATM   40  H4  UNL     1       8.620   1.735  -0.956  1.00  0.00           H  
HETATM   41  H5  UNL     1       7.762   1.725  -2.563  1.00  0.00           H  
HETATM   42  H6  UNL     1       5.747   0.861  -1.639  1.00  0.00           H  
HETATM   43  H7  UNL     1       7.401  -1.159  -0.276  1.00  0.00           H  
HETATM   44  H8  UNL     1       8.163  -0.537  -1.744  1.00  0.00           H  
HETATM   45  H9  UNL     1       6.531  -1.261  -1.859  1.00  0.00           H  
HETATM   46  H10 UNL     1       5.771   1.979   0.546  1.00  0.00           H  
HETATM   47  H11 UNL     1       5.523  -1.018   0.713  1.00  0.00           H  
HETATM   48  H12 UNL     1       2.804  -1.335   0.903  1.00  0.00           H  
HETATM   49  H13 UNL     1       3.553  -1.408   2.497  1.00  0.00           H  
HETATM   50  H14 UNL     1       1.464   0.788   1.854  1.00  0.00           H  
HETATM   51  H15 UNL     1       2.201   0.370   3.372  1.00  0.00           H  
HETATM   52  H16 UNL     1       0.096  -0.375   3.608  1.00  0.00           H  
HETATM   53  H17 UNL     1       0.575  -2.724   4.182  1.00  0.00           H  
HETATM   54  H18 UNL     1       2.178  -2.561   3.457  1.00  0.00           H  
HETATM   55  H19 UNL     1       1.634  -1.457   4.830  1.00  0.00           H  
HETATM   56  H20 UNL     1      -0.649  -2.537   2.681  1.00  0.00           H  
HETATM   57  H21 UNL     1       0.836  -3.510   1.268  1.00  0.00           H  
HETATM   58  H22 UNL     1       0.805  -2.116   0.057  1.00  0.00           H  
HETATM   59  H23 UNL     1      -0.862  -3.586  -0.640  1.00  0.00           H  
HETATM   60  H24 UNL     1      -1.691  -3.482   1.014  1.00  0.00           H  
HETATM   61  H25 UNL     1      -0.560  -1.133  -0.473  1.00  0.00           H  
HETATM   62  H26 UNL     1      -2.324  -0.823  -1.732  1.00  0.00           H  
HETATM   63  H27 UNL     1      -2.992  -3.008  -1.911  1.00  0.00           H  
HETATM   64  H28 UNL     1      -3.663  -3.072  -0.292  1.00  0.00           H  
HETATM   65  H29 UNL     1      -5.644  -2.692  -1.287  1.00  0.00           H  
HETATM   66  H30 UNL     1      -4.905  -2.286  -2.829  1.00  0.00           H  
HETATM   67  H31 UNL     1      -6.113  -0.534  -0.854  1.00  0.00           H  
HETATM   68  H32 UNL     1      -5.349   0.029  -3.763  1.00  0.00           H  
HETATM   69  H33 UNL     1      -6.732  -0.925  -3.204  1.00  0.00           H  
HETATM   70  H34 UNL     1      -7.745   0.717  -1.996  1.00  0.00           H  
HETATM   71  H35 UNL     1      -7.680   2.577  -3.578  1.00  0.00           H  
HETATM   72  H36 UNL     1      -5.794   2.931  -2.434  1.00  0.00           H  
HETATM   73  H37 UNL     1      -6.933   2.630  -1.121  1.00  0.00           H  
HETATM   74  H38 UNL     1      -4.342   2.487  -0.721  1.00  0.00           H  
HETATM   75  H39 UNL     1      -5.465   1.502   0.244  1.00  0.00           H  
HETATM   76  H40 UNL     1      -3.382   0.064  -3.238  1.00  0.00           H  
HETATM   77  H41 UNL     1      -4.051   1.675  -2.986  1.00  0.00           H  
HETATM   78  H42 UNL     1      -2.514   1.316  -2.183  1.00  0.00           H  
HETATM   79  H43 UNL     1      -4.296  -0.557   0.545  1.00  0.00           H  
HETATM   80  H44 UNL     1      -2.597   1.774  -0.034  1.00  0.00           H  
HETATM   81  H45 UNL     1      -3.364   1.247   1.474  1.00  0.00           H  
HETATM   82  H46 UNL     1      -1.146   1.071   2.021  1.00  0.00           H  
HETATM   83  H47 UNL     1      -0.174   1.571   0.031  1.00  0.00           H  
HETATM   84  H48 UNL     1      -2.231  -1.838   3.252  1.00  0.00           H  
HETATM   85  H49 UNL     1      -3.222  -2.222   1.871  1.00  0.00           H  
HETATM   86  H50 UNL     1      -3.189  -0.522   2.645  1.00  0.00           H  
HETATM   87  H51 UNL     1       9.417   1.370   1.562  1.00  0.00           H  
CONECT    1    2   37   38   39
CONECT    2    3   40   41
CONECT    3    4    5   42
CONECT    4   43   44   45
CONECT    5    6   34   46
CONECT    6    7   47
CONECT    7    8    8    9
CONECT    9   10   48   49
CONECT   10   11   50   51
CONECT   11   12   13   52
CONECT   12   53   54   55
CONECT   13   14   32   56
CONECT   14   15   57   58
CONECT   15   16   59   60
CONECT   16   17   32   61
CONECT   17   18   28   62
CONECT   18   19   63   64
CONECT   19   20   65   66
CONECT   20   21   26   67
CONECT   21   22   68   69
CONECT   22   23   24   70
CONECT   23   71
CONECT   24   25   72   73
CONECT   25   26   74   75
CONECT   26   27   28
CONECT   27   76   77   78
CONECT   28   29   79
CONECT   29   30   80   81
CONECT   30   31   32   82
CONECT   31   83
CONECT   32   33
CONECT   33   84   85   86
CONECT   34   35   35   36
CONECT   36   87
END

HMDB0242416
     RDKit          3D
Deoxycholylisoleucine
 87 90  0  0  0  0  0  0  0  0999 V2000
    7.0982    3.1964   -1.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6376    1.7828   -1.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6499    0.7597   -1.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1911   -0.6234   -1.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2224    0.9771    0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2522   -0.0220    0.8423 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9977    0.2958    1.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7216    1.5356    1.5302 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0028   -0.7400    1.8057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7850   -0.1228    2.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7190   -1.0267    2.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3516   -1.9752    3.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063   -1.6952    1.9757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3279   -2.6282    0.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0621   -3.0040    0.2636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4765   -1.6068    0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6650   -1.2567   -0.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5632   -2.3847   -1.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8595   -2.0017   -1.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3188   -0.5974   -1.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0090   -0.1123   -2.9080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8371    1.0798   -2.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3347    1.6590   -3.7148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1395    2.1063   -1.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0911    1.6556   -0.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2996    0.4407   -1.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4872    0.8553   -2.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4967   -0.1400   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7397    0.8768    0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805    0.4369    1.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5298    0.6574    0.0749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4082   -1.0310    1.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6282   -1.4120    2.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3646    0.8884    1.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3449    0.0208    2.2908 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4916    1.6906    1.3368 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0810    3.2772   -1.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8155    3.8953   -1.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0057    3.4437   -0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6200    1.7345   -0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7623    1.7249   -2.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7470    0.8609   -1.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4015   -1.1592   -0.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1634   -0.5368   -1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5309   -1.2610   -1.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7710    1.9793    0.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5229   -1.0180    0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8035   -1.3346    0.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5534   -1.4081    2.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4642    0.7880    1.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2012    0.3699    3.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957   -0.3749    3.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5753   -2.7241    4.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1784   -2.5611    3.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6340   -1.4565    4.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6493   -2.5371    2.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8357   -3.5103    1.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8047   -2.1159    0.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8620   -3.5856   -0.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6908   -3.4820    1.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5596   -1.1330   -0.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3243   -0.8231   -1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918   -3.0076   -1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6633   -3.0723   -0.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6441   -2.6916   -1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9049   -2.2863   -2.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1134   -0.5341   -0.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3489    0.0288   -3.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7322   -0.9246   -3.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7452    0.7172   -1.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6800    2.5773   -3.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7942    2.9308   -2.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9335    2.6299   -1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3425    2.4868   -0.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4647    1.5020    0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3816    0.0641   -3.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0511    1.6755   -2.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5137    1.3155   -2.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2958   -0.5574    0.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5969    1.7736   -0.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3639    1.2469    1.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1462    1.0708    2.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1738    1.5710    0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2312   -1.8382    3.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2220   -2.2222    1.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1889   -0.5215    2.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4169    1.3703    1.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Synonyms

Value	Source
Deoxycholylisoleucine	HMDB
Ile-Deoxycho	HMDB
Ile-DCA	HMDB
Isoleucodeoxycholic acid	HMDB
Isoleucodeoxycholate	HMDB

Molecular Formula

C₃₀H₅₁NO₅

Average Mass

505.74

Monoisotopic Mass

505.376723746

IUPAC Name

2-(4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)-3-methylpentanoic acid

Traditional Name

2-(4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)-3-methylpentanoic acid

CAS Registry Number

Not Available

SMILES

CCC(C)C(NC(=O)CCC(C)C1CCC2C3CCC4CC(O)CCC4(C)C3CC(O)C12C)C(O)=O

InChI Identifier

InChI=1S/C30H51NO5/c1-6-17(2)27(28(35)36)31-26(34)12-7-18(3)22-10-11-23-21-9-8-19-15-20(32)13-14-29(19,4)24(21)16-25(33)30(22,23)5/h17-25,27,32-33H,6-16H2,1-5H3,(H,31,34)(H,35,36)

InChI Key

QTMPUVRWTSAYOC-UHFFFAOYSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.003 g/L	ALOGPS
logP	3.71	ALOGPS
logP	4.59	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	3.97	ChemAxon
pKa (Strongest Basic)	-0.25	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.86 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	140.09 m³·mol⁻¹	ChemAxon
Polarizability	59.52 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0bt9-0105940000-111b67e950fac432a645	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1009200000-d5dfcf461725bea4453e	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05mk-4922000000-3e884052af26a3bf24ef	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000490000-ac950438bbd7e655f795	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kpi-0209230000-7ed71a5e6a57ee44c20c	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fu-1019300000-98d824acf09c0923e5c1	2021-10-12	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Intestine

Tissue Locations

Intestine

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

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

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0242416

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Guzior DV, Quinn RA: Review: microbial transformations of human bile acids. Microbiome. 2021 Jun 14;9(1):140. doi: 10.1186/s40168-021-01101-1. [PubMed:34127070 ]
Quinn RA, Melnik AV, Vrbanac A, Fu T, Patras KA, Christy MP, Bodai Z, Belda-Ferre P, Tripathi A, Chung LK, Downes M, Welch RD, Quinn M, Humphrey G, Panitchpakdi M, Weldon KC, Aksenov A, da Silva R, Avila-Pacheco J, Clish C, Bae S, Mallick H, Franzosa EA, Lloyd-Price J, Bussell R, Thron T, Nelson AT, Wang M, Leszczynski E, Vargas F, Gauglitz JM, Meehan MJ, Gentry E, Arthur TD, Komor AC, Poulsen O, Boland BS, Chang JT, Sandborn WJ, Lim M, Garg N, Lumeng JC, Xavier RJ, Kazmierczak BI, Jain R, Egan M, Rhee KE, Ferguson D, Raffatellu M, Vlamakis H, Haddad GG, Siegel D, Huttenhower C, Mazmanian SK, Evans RM, Nizet V, Knight R, Dorrestein PC: Global chemical effects of the microbiome include new bile-acid conjugations. Nature. 2020 Mar;579(7797):123-129. doi: 10.1038/s41586-020-2047-9. Epub 2020 Feb 26. [PubMed:32103176 ]

Showing metabocard for Deoxycholylisoleucine (MMDBc0057261)

MOL for #<Metabolite:0x00007fece40fc908>

3D MOL for #<Metabolite:0x00007fece40fc908>

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3D-SDF for #<Metabolite:0x00007fece40fc908>

PDB for #<Metabolite:0x00007fece40fc908>

3D PDB for #<Metabolite:0x00007fece40fc908>

SMILES for #<Metabolite:0x00007fece40fc908>

INCHI for #<Metabolite:0x00007fece40fc908>

Structure for #<Metabolite:0x00007fece40fc908>

3D Structure for #<Metabolite:0x00007fece40fc908>