MiMeDB: Showing metabocard for Chenodeoxycholyllysine (MMDBc0057245)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-11-10 23:36:00 UTC

Update Date

2024-04-30 20:56:49 UTC

Metabolite ID

MMDBc0057245

Metabolite Identification

Common Name

Chenodeoxycholyllysine

Description

Chenodeoxycholyllysine 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. Chenodeoxycholyllysine consists of the bile acid chenodeoxycholic acid conjugated to the amino acid Lysine 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 Chenodeoxycholyllysine, 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 ). Chenodeoxycholyllysine 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


  Mrv1652308302120442D          

 37 40  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
    1.7057   -3.7348    0.0000 O   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
    3.3618   -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
    9.8313   -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
   11.2602   -2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9747   -1.8186    0.0000 N   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
 17 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
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 16 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 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
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END

HMDB0242400
     RDKit          3D
Chenodeoxycholyllysine
 89 92  0  0  0  0  0  0  0  0999 V2000
    0.6114   -0.9141    1.8549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5132   -1.1947    0.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8810   -1.6434   -0.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8516   -0.5124    0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2344   -0.8718   -0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3999   -2.0038   -0.7713 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3209   -0.0245   -0.0584 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7128   -0.3706   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0748    0.6688   -1.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3941    0.6420   -2.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6116    0.7795   -1.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6632    2.0564   -0.4487 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9108    2.0400    0.3193 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4517   -0.3065    0.8296 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1008    0.5757    1.6764 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4820   -1.1400    1.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6029   -2.1041    0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7068   -2.4904   -1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7885   -1.6389   -2.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1794   -0.7564   -0.8923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4907   -0.0791   -1.0033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2973    1.4196   -1.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6127    1.8415   -2.4870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9430    2.2309   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4092    1.8897    0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8123    2.6535    1.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1172    2.2126    1.9068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1644    2.2188    0.9777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8973    0.7575    2.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6687   -0.0526    1.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7018    0.4485    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3646    0.1264   -1.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4470   -0.4494    0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8982   -0.6169    1.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4081   -0.8972    1.4734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9994   -1.6687    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8392   -2.9307    0.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343    0.0389    2.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0406   -1.7483    2.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6594   -1.1144    2.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4013   -0.1753   -0.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9126   -1.8018   -1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2177   -2.5392    0.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5949    0.3767   -0.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8590   -0.1033    1.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2022    0.9077    0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6724   -1.3711   -0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3044    0.5674   -2.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8096    1.6738   -1.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4868   -0.3434   -2.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3821    1.3906   -2.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9148   -0.1213   -0.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4632    0.9378   -2.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8465    2.1668    0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6478    2.9047   -1.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7408    2.2567    1.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3492    1.0812    0.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6482   -2.0542    0.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4808   -3.0925    0.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0626   -3.5628   -1.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369   -2.4549   -1.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5980   -2.2135   -2.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3238   -1.0413   -2.8502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4044    0.0308   -0.8008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9468   -0.4267   -1.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1876    1.6322   -1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7548    1.0701   -3.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8731    3.3002   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3691    2.1732    0.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9313    2.4355   -0.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9197    3.7435    1.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0497    2.6186    2.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3352    2.8500    2.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8921    1.6911    1.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8841    0.4375    2.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1817    0.6540    3.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3160   -1.0720    1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6873   -0.3037    0.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1323    0.8638   -2.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1702   -0.9286   -1.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4882    0.1659   -1.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8968   -1.4520   -0.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3934   -1.4409    1.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0770    0.2782    2.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9356    0.1103    1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1728   -1.4214    2.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5488   -2.9890    1.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2003   -3.8531    0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2764   -3.0847   -0.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  8 14  1  0
 14 15  2  0
 14 16  1  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
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 29 30  1  0
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 31 32  1  0
 31 33  1  0
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 34 35  1  0
 35 36  1  0
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 36 17  1  0
 36 20  1  0
 33 21  1  0
 31 25  1  0
  1 38  1  0
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 33 82  1  0
 34 83  1  0
 34 84  1  0
 35 85  1  0
 35 86  1  0
 37 87  1  0
 37 88  1  0
 37 89  1  0
M  END


  Mrv1652308302120442D          

 37 40  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
    1.7057   -3.7348    0.0000 O   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
    3.3618   -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
    9.8313   -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
   11.2602   -2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9747   -1.8186    0.0000 N   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
 17 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
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 16 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 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
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0057245

> <DATABASE_NAME>
MIME

> <SMILES>
CC(CCC(=O)NC(CCCCN)C(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H52N2O5/c1-18(7-10-26(35)32-24(28(36)37)6-4-5-15-31)21-8-9-22-27-23(12-14-30(21,22)3)29(2)13-11-20(33)16-19(29)17-25(27)34/h18-25,27,33-34H,4-17,31H2,1-3H3,(H,32,35)(H,36,37)

> <INCHI_KEY>
LJAIXMQYBNEUSB-UHFFFAOYSA-N

> <FORMULA>
C30H52N2O5

> <MOLECULAR_WEIGHT>
520.755

> <EXACT_MASS>
520.387622782

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
61.3334510483249

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-amino-2-(4-{5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)hexanoic acid

> <ALOGPS_LOGP>
0.17

> <JCHEM_LOGP>
0.7818951015801848

> <ALOGPS_LOGS>
-5.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.517207767044667

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6835549520877273

> <JCHEM_PKA_STRONGEST_BASIC>
10.205444469725345

> <JCHEM_POLAR_SURFACE_AREA>
132.88000000000002

> <JCHEM_REFRACTIVITY>
143.8834

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-amino-2-(4-{5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)hexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242400
     RDKit          3D
Chenodeoxycholyllysine
 89 92  0  0  0  0  0  0  0  0999 V2000
    0.6114   -0.9141    1.8549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5132   -1.1947    0.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8810   -1.6434   -0.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8516   -0.5124    0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2344   -0.8718   -0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3999   -2.0038   -0.7713 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3209   -0.0245   -0.0584 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7128   -0.3706   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0748    0.6688   -1.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3941    0.6420   -2.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6116    0.7795   -1.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6632    2.0564   -0.4487 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9108    2.0400    0.3193 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4517   -0.3065    0.8296 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1008    0.5757    1.6764 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4820   -1.1400    1.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6029   -2.1041    0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7068   -2.4904   -1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7885   -1.6389   -2.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1794   -0.7564   -0.8923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4907   -0.0791   -1.0033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2973    1.4196   -1.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6127    1.8415   -2.4870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9430    2.2309   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4092    1.8897    0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8123    2.6535    1.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1172    2.2126    1.9068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1644    2.2188    0.9777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8973    0.7575    2.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6687   -0.0526    1.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7018    0.4485    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3646    0.1264   -1.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4470   -0.4494    0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8982   -0.6169    1.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4081   -0.8972    1.4734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9994   -1.6687    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8392   -2.9307    0.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343    0.0389    2.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0406   -1.7483    2.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6594   -1.1144    2.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4013   -0.1753   -0.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9126   -1.8018   -1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2177   -2.5392    0.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5949    0.3767   -0.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8590   -0.1033    1.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2022    0.9077    0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6724   -1.3711   -0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3044    0.5674   -2.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8096    1.6738   -1.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4868   -0.3434   -2.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3821    1.3906   -2.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9148   -0.1213   -0.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4632    0.9378   -2.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8465    2.1668    0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6478    2.9047   -1.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7408    2.2567    1.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3492    1.0812    0.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6482   -2.0542    0.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4808   -3.0925    0.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0626   -3.5628   -1.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369   -2.4549   -1.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5980   -2.2135   -2.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3238   -1.0413   -2.8502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4044    0.0308   -0.8008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9468   -0.4267   -1.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1876    1.6322   -1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7548    1.0701   -3.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8731    3.3002   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3691    2.1732    0.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9313    2.4355   -0.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9197    3.7435    1.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0497    2.6186    2.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3352    2.8500    2.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8921    1.6911    1.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8841    0.4375    2.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1817    0.6540    3.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3160   -1.0720    1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6873   -0.3037    0.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1323    0.8638   -2.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1702   -0.9286   -1.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4882    0.1659   -1.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8968   -1.4520   -0.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3934   -1.4409    1.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0770    0.2782    2.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9356    0.1103    1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1728   -1.4214    2.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5488   -2.9890    1.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2003   -3.8531    0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2764   -3.0847   -0.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  8 14  1  0
 14 15  2  0
 14 16  1  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
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 29 30  1  0
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 31 32  1  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 17  1  0
 36 20  1  0
 33 21  1  0
 31 25  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
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  3 42  1  0
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  4 44  1  0
  4 45  1  0
  7 46  1  0
  8 47  1  0
  9 48  1  0
  9 49  1  0
 10 50  1  0
 10 51  1  0
 11 52  1  0
 11 53  1  0
 12 54  1  0
 12 55  1  0
 13 56  1  0
 13 57  1  0
 16 58  1  0
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 35 85  1  0
 35 86  1  0
 37 87  1  0
 37 88  1  0
 37 89  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  O   UNK     0       3.184  -6.972   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.202  -5.187   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.726  -3.722   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.780  -3.402   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.256  -1.937   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.763  -1.617   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.226  -0.793   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.281  -1.113   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.756  -2.578   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.787  -1.433   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.263  -2.898   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.293  -1.754   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.800  -2.074   0.000  0.00  0.00           C+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      18.352  -4.165   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      19.685  -3.395   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      21.019  -4.165   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0      22.353  -3.395   0.000  0.00  0.00           N+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   28                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   20   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   16   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   12   15   32                                             
CONECT   32   31                                                            
CONECT   33    4   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

COMPND    HMDB0242400
HETATM    1  C1  UNL     1       0.611  -0.914   1.855  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.513  -1.195   0.370  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.881  -1.643  -0.100  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.852  -0.512   0.158  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.234  -0.872  -0.243  1.00  0.00           C  
HETATM    6  O1  UNL     1       4.400  -2.004  -0.771  1.00  0.00           O  
HETATM    7  N1  UNL     1       5.321  -0.024  -0.058  1.00  0.00           N  
HETATM    8  C6  UNL     1       6.713  -0.371  -0.448  1.00  0.00           C  
HETATM    9  C7  UNL     1       7.075   0.669  -1.453  1.00  0.00           C  
HETATM   10  C8  UNL     1       8.394   0.642  -2.094  1.00  0.00           C  
HETATM   11  C9  UNL     1       9.612   0.780  -1.259  1.00  0.00           C  
HETATM   12  C10 UNL     1       9.663   2.056  -0.449  1.00  0.00           C  
HETATM   13  N2  UNL     1      10.911   2.040   0.319  1.00  0.00           N  
HETATM   14  C11 UNL     1       7.452  -0.306   0.830  1.00  0.00           C  
HETATM   15  O2  UNL     1       7.101   0.576   1.676  1.00  0.00           O  
HETATM   16  O3  UNL     1       8.482  -1.140   1.155  1.00  0.00           O  
HETATM   17  C12 UNL     1      -0.603  -2.104   0.093  1.00  0.00           C  
HETATM   18  C13 UNL     1      -0.707  -2.490  -1.394  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.788  -1.639  -2.009  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.179  -0.756  -0.892  1.00  0.00           C  
HETATM   21  C16 UNL     1      -3.491  -0.079  -1.003  1.00  0.00           C  
HETATM   22  C17 UNL     1      -3.297   1.420  -1.190  1.00  0.00           C  
HETATM   23  O4  UNL     1      -3.613   1.841  -2.487  1.00  0.00           O  
HETATM   24  C18 UNL     1      -3.943   2.231  -0.126  1.00  0.00           C  
HETATM   25  C19 UNL     1      -5.409   1.890   0.087  1.00  0.00           C  
HETATM   26  C20 UNL     1      -5.812   2.653   1.332  1.00  0.00           C  
HETATM   27  C21 UNL     1      -7.117   2.213   1.907  1.00  0.00           C  
HETATM   28  O5  UNL     1      -8.164   2.219   0.978  1.00  0.00           O  
HETATM   29  C22 UNL     1      -6.897   0.757   2.315  1.00  0.00           C  
HETATM   30  C23 UNL     1      -6.669  -0.053   1.106  1.00  0.00           C  
HETATM   31  C24 UNL     1      -5.702   0.448   0.086  1.00  0.00           C  
HETATM   32  C25 UNL     1      -6.365   0.126  -1.274  1.00  0.00           C  
HETATM   33  C26 UNL     1      -4.447  -0.449   0.064  1.00  0.00           C  
HETATM   34  C27 UNL     1      -3.898  -0.617   1.420  1.00  0.00           C  
HETATM   35  C28 UNL     1      -2.408  -0.897   1.473  1.00  0.00           C  
HETATM   36  C29 UNL     1      -1.999  -1.669   0.304  1.00  0.00           C  
HETATM   37  C30 UNL     1      -2.839  -2.931   0.179  1.00  0.00           C  
HETATM   38  H1  UNL     1       0.234   0.039   2.188  1.00  0.00           H  
HETATM   39  H2  UNL     1       0.041  -1.748   2.369  1.00  0.00           H  
HETATM   40  H3  UNL     1       1.659  -1.114   2.226  1.00  0.00           H  
HETATM   41  H4  UNL     1       0.401  -0.175  -0.089  1.00  0.00           H  
HETATM   42  H5  UNL     1       1.913  -1.802  -1.198  1.00  0.00           H  
HETATM   43  H6  UNL     1       2.218  -2.539   0.461  1.00  0.00           H  
HETATM   44  H7  UNL     1       2.595   0.377  -0.508  1.00  0.00           H  
HETATM   45  H8  UNL     1       2.859  -0.103   1.163  1.00  0.00           H  
HETATM   46  H9  UNL     1       5.202   0.908   0.372  1.00  0.00           H  
HETATM   47  H10 UNL     1       6.672  -1.371  -0.880  1.00  0.00           H  
HETATM   48  H11 UNL     1       6.304   0.567  -2.283  1.00  0.00           H  
HETATM   49  H12 UNL     1       6.810   1.674  -1.015  1.00  0.00           H  
HETATM   50  H13 UNL     1       8.487  -0.343  -2.635  1.00  0.00           H  
HETATM   51  H14 UNL     1       8.382   1.391  -2.929  1.00  0.00           H  
HETATM   52  H15 UNL     1       9.915  -0.121  -0.749  1.00  0.00           H  
HETATM   53  H16 UNL     1      10.463   0.938  -2.028  1.00  0.00           H  
HETATM   54  H17 UNL     1       8.846   2.167   0.272  1.00  0.00           H  
HETATM   55  H18 UNL     1       9.648   2.905  -1.145  1.00  0.00           H  
HETATM   56  H19 UNL     1      10.741   2.257   1.321  1.00  0.00           H  
HETATM   57  H20 UNL     1      11.349   1.081   0.316  1.00  0.00           H  
HETATM   58  H21 UNL     1       8.648  -2.054   0.774  1.00  0.00           H  
HETATM   59  H22 UNL     1      -0.481  -3.093   0.631  1.00  0.00           H  
HETATM   60  H23 UNL     1      -1.063  -3.563  -1.480  1.00  0.00           H  
HETATM   61  H24 UNL     1       0.237  -2.455  -1.924  1.00  0.00           H  
HETATM   62  H25 UNL     1      -2.598  -2.213  -2.496  1.00  0.00           H  
HETATM   63  H26 UNL     1      -1.324  -1.041  -2.850  1.00  0.00           H  
HETATM   64  H27 UNL     1      -1.404   0.031  -0.801  1.00  0.00           H  
HETATM   65  H28 UNL     1      -3.947  -0.427  -1.981  1.00  0.00           H  
HETATM   66  H29 UNL     1      -2.188   1.632  -1.100  1.00  0.00           H  
HETATM   67  H30 UNL     1      -3.755   1.070  -3.097  1.00  0.00           H  
HETATM   68  H31 UNL     1      -3.873   3.300  -0.438  1.00  0.00           H  
HETATM   69  H32 UNL     1      -3.369   2.173   0.826  1.00  0.00           H  
HETATM   70  H33 UNL     1      -5.931   2.436  -0.758  1.00  0.00           H  
HETATM   71  H34 UNL     1      -5.920   3.743   1.068  1.00  0.00           H  
HETATM   72  H35 UNL     1      -5.050   2.619   2.131  1.00  0.00           H  
HETATM   73  H36 UNL     1      -7.335   2.850   2.780  1.00  0.00           H  
HETATM   74  H37 UNL     1      -8.892   1.691   1.437  1.00  0.00           H  
HETATM   75  H38 UNL     1      -7.884   0.438   2.768  1.00  0.00           H  
HETATM   76  H39 UNL     1      -6.182   0.654   3.131  1.00  0.00           H  
HETATM   77  H40 UNL     1      -6.316  -1.072   1.447  1.00  0.00           H  
HETATM   78  H41 UNL     1      -7.687  -0.304   0.673  1.00  0.00           H  
HETATM   79  H42 UNL     1      -6.132   0.864  -2.038  1.00  0.00           H  
HETATM   80  H43 UNL     1      -6.170  -0.929  -1.564  1.00  0.00           H  
HETATM   81  H44 UNL     1      -7.488   0.166  -1.151  1.00  0.00           H  
HETATM   82  H45 UNL     1      -4.897  -1.452  -0.223  1.00  0.00           H  
HETATM   83  H46 UNL     1      -4.393  -1.441   1.966  1.00  0.00           H  
HETATM   84  H47 UNL     1      -4.077   0.278   2.088  1.00  0.00           H  
HETATM   85  H48 UNL     1      -1.936   0.110   1.525  1.00  0.00           H  
HETATM   86  H49 UNL     1      -2.173  -1.421   2.416  1.00  0.00           H  
HETATM   87  H50 UNL     1      -3.549  -2.989   1.028  1.00  0.00           H  
HETATM   88  H51 UNL     1      -2.200  -3.853   0.334  1.00  0.00           H  
HETATM   89  H52 UNL     1      -3.276  -3.085  -0.808  1.00  0.00           H  
CONECT    1    2   38   39   40
CONECT    2    3   17   41
CONECT    3    4   42   43
CONECT    4    5   44   45
CONECT    5    6    6    7
CONECT    7    8   46
CONECT    8    9   14   47
CONECT    9   10   48   49
CONECT   10   11   50   51
CONECT   11   12   52   53
CONECT   12   13   54   55
CONECT   13   56   57
CONECT   14   15   15   16
CONECT   16   58
CONECT   17   18   36   59
CONECT   18   19   60   61
CONECT   19   20   62   63
CONECT   20   21   36   64
CONECT   21   22   33   65
CONECT   22   23   24   66
CONECT   23   67
CONECT   24   25   68   69
CONECT   25   26   31   70
CONECT   26   27   71   72
CONECT   27   28   29   73
CONECT   28   74
CONECT   29   30   75   76
CONECT   30   31   77   78
CONECT   31   32   33
CONECT   32   79   80   81
CONECT   33   34   82
CONECT   34   35   83   84
CONECT   35   36   85   86
CONECT   36   37
CONECT   37   87   88   89
END

HMDB0242400
     RDKit          3D
Chenodeoxycholyllysine
 89 92  0  0  0  0  0  0  0  0999 V2000
    0.6114   -0.9141    1.8549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5132   -1.1947    0.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8810   -1.6434   -0.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8516   -0.5124    0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2344   -0.8718   -0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3999   -2.0038   -0.7713 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3209   -0.0245   -0.0584 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7128   -0.3706   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0748    0.6688   -1.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3941    0.6420   -2.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6116    0.7795   -1.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6632    2.0564   -0.4487 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9108    2.0400    0.3193 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4517   -0.3065    0.8296 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1008    0.5757    1.6764 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4820   -1.1400    1.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6029   -2.1041    0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7068   -2.4904   -1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7885   -1.6389   -2.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1794   -0.7564   -0.8923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4907   -0.0791   -1.0033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2973    1.4196   -1.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6127    1.8415   -2.4870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9430    2.2309   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4092    1.8897    0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8123    2.6535    1.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1172    2.2126    1.9068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1644    2.2188    0.9777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8973    0.7575    2.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6687   -0.0526    1.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7018    0.4485    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3646    0.1264   -1.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4470   -0.4494    0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8982   -0.6169    1.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4081   -0.8972    1.4734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9994   -1.6687    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8392   -2.9307    0.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343    0.0389    2.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0406   -1.7483    2.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6594   -1.1144    2.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4013   -0.1753   -0.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9126   -1.8018   -1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2177   -2.5392    0.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5949    0.3767   -0.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8590   -0.1033    1.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2022    0.9077    0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6724   -1.3711   -0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3044    0.5674   -2.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8096    1.6738   -1.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4868   -0.3434   -2.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3821    1.3906   -2.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9148   -0.1213   -0.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4632    0.9378   -2.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8465    2.1668    0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6478    2.9047   -1.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7408    2.2567    1.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3492    1.0812    0.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6482   -2.0542    0.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4808   -3.0925    0.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0626   -3.5628   -1.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369   -2.4549   -1.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5980   -2.2135   -2.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3238   -1.0413   -2.8502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4044    0.0308   -0.8008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9468   -0.4267   -1.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Synonyms

Value	Source
6-Amino-2-[(4-{5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl}-1-hydroxypentylidene)amino]hexanoate	Generator
Chenodeoxycholyllysine	HMDB
Lys-Chenodeoxycho	HMDB
Lys-CDCA	HMDB
Lysochenodeoxycholic acid	HMDB
Lysochenodeoxycholate	HMDB

Molecular Formula

C₃₀H₅₂N₂O₅

Average Mass

520.755

Monoisotopic Mass

520.387622782

IUPAC Name

6-amino-2-(4-{5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)hexanoic acid

Traditional Name

6-amino-2-(4-{5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)hexanoic acid

CAS Registry Number

Not Available

SMILES

CC(CCC(=O)NC(CCCCN)C(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CCC12C

InChI Identifier

InChI=1S/C30H52N2O5/c1-18(7-10-26(35)32-24(28(36)37)6-4-5-15-31)21-8-9-22-27-23(12-14-30(21,22)3)29(2)13-11-20(33)16-19(29)17-25(27)34/h18-25,27,33-34H,4-17,31H2,1-3H3,(H,32,35)(H,36,37)

InChI Key

LJAIXMQYBNEUSB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Glycinated bile acids and derivatives

Alternative Parents

Substituents

Glycinated bile acid
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
7-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid or derivatives
Medium-chain fatty acid
Hydroxy fatty acid
Amino fatty acid
Fatty acyl
Fatty acid
N-acyl-amine
Fatty amide
Cyclic alcohol
Amino acid
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Amino acid or derivatives
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.003 g/L	ALOGPS
logP	0.17	ALOGPS
logP	0.78	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	132.88 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	143.88 m³·mol⁻¹	ChemAxon
Polarizability	61.33 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	splash10-00di-0000390000-d81e84acea900e1d33a2	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-6904740000-86ef46b840f67811db77	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0535-9122000000-61a357362ad28f4840dc	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000090000-afc030cd5304f761b25f	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-2200090000-4d2a5ec0e748a2f5f729	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9405830000-b8e0cba8433e822e356f	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
Bacteria	Firmicutes	2	Human ; Human feces; Human saliva

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

HMDB0242400

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

14559780

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 Chenodeoxycholyllysine (MMDBc0057245)

MOL for #<Metabolite:0x00007fece0f364f0>

3D MOL for #<Metabolite:0x00007fece0f364f0>

3D SDF for #<Metabolite:0x00007fece0f364f0>

3D-SDF for #<Metabolite:0x00007fece0f364f0>

PDB for #<Metabolite:0x00007fece0f364f0>

3D PDB for #<Metabolite:0x00007fece0f364f0>

SMILES for #<Metabolite:0x00007fece0f364f0>

INCHI for #<Metabolite:0x00007fece0f364f0>

Structure for #<Metabolite:0x00007fece0f364f0>

3D Structure for #<Metabolite:0x00007fece0f364f0>