MiMeDB: Showing metabocard for Chenodeoxycholylaspartic acid (MMDBc0057247)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-11-10 23:36:19 UTC

Update Date

2024-04-30 20:56:51 UTC

Metabolite ID

MMDBc0057247

Metabolite Identification

Common Name

Chenodeoxycholylaspartic acid

Description

Chenodeoxycholylaspartic acid 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. Chenodeoxycholylaspartic acid consists of the bile acid chenodeoxycholic acid conjugated to the amino acid Aspartic acid 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 Chenodeoxycholylaspartic acid, 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 ). Chenodeoxycholylaspartic acid 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


  Mrv1652308302120532D          

 36 39  0  0  0  0            999 V2000
    7.6405   -2.9427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3550   -2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3550   -1.7052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0694   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7839   -2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4984   -2.9427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2128   -2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2128   -1.7052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9273   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6418   -2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3563   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3563   -3.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0707   -2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1570   -1.7097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9639   -1.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3764   -2.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1834   -2.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7354   -1.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4805   -1.0265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5424   -1.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7974   -2.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6043   -2.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8593   -3.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6662   -3.8949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3072   -4.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5003   -4.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2453   -3.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6933   -3.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4383   -3.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8863   -3.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0793   -3.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8244   -2.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2113   -3.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7839   -1.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4984   -1.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0694   -1.2927    0.0000 O   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  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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
 18 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
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 17 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 13 32  1  0  0  0  0
 16 32  1  0  0  0  0
 32 33  1  0  0  0  0
  5 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END

HMDB0242402
     RDKit          3D
Chenodeoxycholylaspartic acid
 81 84  0  0  0  0  0  0  0  0999 V2000
    1.8449   -1.6839    2.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6090   -0.5335    1.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8446   -0.5001    0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0843   -0.2499    1.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3101   -0.2192    0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1602   -0.3661   -0.8056 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5837   -0.0317    0.9944 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8268    0.0295    0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7497    0.7531   -1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3383    2.1343   -0.8143 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1786    2.4415   -0.4927 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2407    3.2067   -0.9482 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3895   -1.2951    0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8276   -2.3538    0.5016 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6049   -1.4671   -0.5556 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466   -0.8997    0.5706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3650   -2.2366   -0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1081   -2.2990   -0.5911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3690   -0.8781   -1.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7488   -0.4006   -0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2512    0.5766   -1.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0597   -0.0333   -2.7653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9063    1.7924   -1.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8694    1.5312   -0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2280    1.3623   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0965    0.3359   -0.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1696    0.0883   -0.9499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2701   -0.9413   -0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2023   -0.7336    0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3996    0.5167    0.8477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3516    1.1287    2.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9379    0.0887    0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9512    1.1066    1.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7732    1.2661    0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2663   -0.0163   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6480    0.3581   -1.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8525   -1.9569    2.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2463   -2.5647    1.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4544   -1.3093    3.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5740    0.3744    1.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8378    0.3880   -0.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0454   -1.3847   -0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2232   -1.0442    2.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0362    0.7021    1.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6006    0.0733    2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5417    0.6839    0.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8204    0.7839   -1.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1370    0.2427   -1.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1844    3.0808   -0.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3727   -1.9879   -0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4682   -1.0672    1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5289   -3.0608    0.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008   -2.2534   -1.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2685   -3.0416   -1.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676   -2.5568    0.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640   -0.9156   -2.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4236   -1.3043   -0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3390    0.9271   -2.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6704   -0.9251   -2.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4992    2.2407   -2.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1830    2.6236   -1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9041    2.5416    0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8279    2.3208   -0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1449    1.0818   -1.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5135    0.6015    0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8772   -0.5781   -1.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9151   -1.1189   -1.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9148   -1.7664    0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5577   -1.6649    0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7195   -0.8316    1.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2304    2.2198    2.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5928    0.6478    2.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3514    0.9462    2.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8252   -0.8089    1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5435    0.8648    2.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4088    2.1277    1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0910    1.6627    0.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9027    2.0410   -0.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0986    1.3623   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -0.4442   -1.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0181    0.4691   -2.5347 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  2  0
 10 12  1  0
  8 13  1  0
 13 14  2  0
 13 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 35 16  1  0
 35 19  1  0
 32 20  1  0
 30 24  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  7 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 12 49  1  0
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 17 53  1  0
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 18 55  1  0
 19 56  1  0
 20 57  1  0
 21 58  1  0
 22 59  1  0
 23 60  1  0
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 25 63  1  0
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 27 66  1  0
 28 67  1  0
 28 68  1  0
 29 69  1  0
 29 70  1  0
 31 71  1  0
 31 72  1  0
 31 73  1  0
 32 74  1  0
 33 75  1  0
 33 76  1  0
 34 77  1  0
 34 78  1  0
 36 79  1  0
 36 80  1  0
 36 81  1  0
M  END


  Mrv1652308302120532D          

 36 39  0  0  0  0            999 V2000
    7.6405   -2.9427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3550   -2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3550   -1.7052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0694   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7839   -2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4984   -2.9427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2128   -2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2128   -1.7052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9273   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6418   -2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3563   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3563   -3.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0707   -2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1570   -1.7097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9639   -1.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3764   -2.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1834   -2.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7354   -1.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4805   -1.0265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5424   -1.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7974   -2.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6043   -2.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8593   -3.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6662   -3.8949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3072   -4.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5003   -4.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2453   -3.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6933   -3.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4383   -3.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8863   -3.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0793   -3.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8244   -2.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2113   -3.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7839   -1.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4984   -1.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0694   -1.2927    0.0000 O   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  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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
 18 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
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 17 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 13 32  1  0  0  0  0
 16 32  1  0  0  0  0
 32 33  1  0  0  0  0
  5 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0057247

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C28H45NO7/c1-15(4-7-23(32)29-21(26(35)36)14-24(33)34)18-5-6-19-25-20(9-11-28(18,19)3)27(2)10-8-17(30)12-16(27)13-22(25)31/h15-22,25,30-31H,4-14H2,1-3H3,(H,29,32)(H,33,34)(H,35,36)

> <INCHI_KEY>
TZJSDNVVGFIRIY-UHFFFAOYSA-N

> <FORMULA>
C28H45NO7

> <MOLECULAR_WEIGHT>
507.668

> <EXACT_MASS>
507.319602793

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
57.30891495118534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.86

> <JCHEM_LOGP>
2.534974616333332

> <ALOGPS_LOGS>
-4.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.46294759282095

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5489495296892675

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4735347307651222

> <JCHEM_POLAR_SURFACE_AREA>
144.16

> <JCHEM_REFRACTIVITY>
132.6066

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.77e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242402
     RDKit          3D
Chenodeoxycholylaspartic acid
 81 84  0  0  0  0  0  0  0  0999 V2000
    1.8449   -1.6839    2.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6090   -0.5335    1.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8446   -0.5001    0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0843   -0.2499    1.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3101   -0.2192    0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1602   -0.3661   -0.8056 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5837   -0.0317    0.9944 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8268    0.0295    0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7497    0.7531   -1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3383    2.1343   -0.8143 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1786    2.4415   -0.4927 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2407    3.2067   -0.9482 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3895   -1.2951    0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8276   -2.3538    0.5016 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6049   -1.4671   -0.5556 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466   -0.8997    0.5706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3650   -2.2366   -0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1081   -2.2990   -0.5911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3690   -0.8781   -1.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7488   -0.4006   -0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2512    0.5766   -1.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0597   -0.0333   -2.7653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9063    1.7924   -1.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8694    1.5312   -0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2280    1.3623   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0965    0.3359   -0.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1696    0.0883   -0.9499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2701   -0.9413   -0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2023   -0.7336    0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3996    0.5167    0.8477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3516    1.1287    2.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9379    0.0887    0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9512    1.1066    1.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7732    1.2661    0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2663   -0.0163   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6480    0.3581   -1.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8525   -1.9569    2.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2463   -2.5647    1.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4544   -1.3093    3.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5740    0.3744    1.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8378    0.3880   -0.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0454   -1.3847   -0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2232   -1.0442    2.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0362    0.7021    1.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6006    0.0733    2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5417    0.6839    0.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8204    0.7839   -1.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1370    0.2427   -1.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1844    3.0808   -0.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3727   -1.9879   -0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4682   -1.0672    1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5289   -3.0608    0.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008   -2.2534   -1.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2685   -3.0416   -1.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676   -2.5568    0.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640   -0.9156   -2.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4236   -1.3043   -0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3390    0.9271   -2.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6704   -0.9251   -2.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4992    2.2407   -2.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1830    2.6236   -1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9041    2.5416    0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8279    2.3208   -0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1449    1.0818   -1.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5135    0.6015    0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8772   -0.5781   -1.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9151   -1.1189   -1.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9148   -1.7664    0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5577   -1.6649    0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7195   -0.8316    1.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2304    2.2198    2.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5928    0.6478    2.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3514    0.9462    2.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8252   -0.8089    1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5435    0.8648    2.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4088    2.1277    1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0910    1.6627    0.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9027    2.0410   -0.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0986    1.3623   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -0.4442   -1.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0181    0.4691   -2.5347 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  2  0
 10 12  1  0
  8 13  1  0
 13 14  2  0
 13 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 35 16  1  0
 35 19  1  0
 32 20  1  0
 30 24  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  7 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 12 49  1  0
 15 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 20 57  1  0
 21 58  1  0
 22 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 26 65  1  0
 27 66  1  0
 28 67  1  0
 28 68  1  0
 29 69  1  0
 29 70  1  0
 31 71  1  0
 31 72  1  0
 31 73  1  0
 32 74  1  0
 33 75  1  0
 33 76  1  0
 34 77  1  0
 34 78  1  0
 36 79  1  0
 36 80  1  0
 36 81  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      14.262  -5.493   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      15.596  -4.723   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      15.596  -3.183   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      16.930  -5.493   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.263  -4.723   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      19.597  -5.493   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      20.931  -4.723   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      20.931  -3.183   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      22.264  -5.493   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.598  -4.723   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.932  -5.493   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.932  -7.033   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.265  -4.723   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.426  -3.191   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.933  -2.871   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.703  -4.205   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      30.209  -4.525   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.239  -3.381   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      30.764  -1.916   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      32.746  -3.701   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      33.222  -5.166   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      34.728  -5.486   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      35.204  -6.950   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      36.710  -7.271   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      34.174  -8.095   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      32.667  -7.775   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      32.191  -6.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      31.161  -7.454   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      30.685  -5.990   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      29.654  -7.134   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      28.148  -6.814   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      27.672  -5.349   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      26.528  -6.380   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      18.263  -3.183   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      19.597  -2.413   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      16.930  -2.413   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   32                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   32                                                  
CONECT   17   16   18   29                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   21   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   17   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   13   16   33                                             
CONECT   33   32                                                            
CONECT   34    5   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

COMPND    HMDB0242402
HETATM    1  C1  UNL     1       1.845  -1.684   2.274  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.609  -0.533   1.237  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.845  -0.500   0.406  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.084  -0.250   1.260  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.310  -0.219   0.420  1.00  0.00           C  
HETATM    6  O1  UNL     1       5.160  -0.366  -0.806  1.00  0.00           O  
HETATM    7  N1  UNL     1       6.584  -0.032   0.994  1.00  0.00           N  
HETATM    8  C6  UNL     1       7.827   0.029   0.300  1.00  0.00           C  
HETATM    9  C7  UNL     1       7.750   0.753  -1.041  1.00  0.00           C  
HETATM   10  C8  UNL     1       7.338   2.134  -0.814  1.00  0.00           C  
HETATM   11  O2  UNL     1       6.179   2.441  -0.493  1.00  0.00           O  
HETATM   12  O3  UNL     1       8.241   3.207  -0.948  1.00  0.00           O  
HETATM   13  C9  UNL     1       8.389  -1.295   0.102  1.00  0.00           C  
HETATM   14  O4  UNL     1       7.828  -2.354   0.502  1.00  0.00           O  
HETATM   15  O5  UNL     1       9.605  -1.467  -0.556  1.00  0.00           O  
HETATM   16  C10 UNL     1       0.347  -0.900   0.571  1.00  0.00           C  
HETATM   17  C11 UNL     1       0.365  -2.237  -0.162  1.00  0.00           C  
HETATM   18  C12 UNL     1      -1.108  -2.299  -0.591  1.00  0.00           C  
HETATM   19  C13 UNL     1      -1.369  -0.878  -1.037  1.00  0.00           C  
HETATM   20  C14 UNL     1      -2.749  -0.401  -0.767  1.00  0.00           C  
HETATM   21  C15 UNL     1      -3.251   0.577  -1.799  1.00  0.00           C  
HETATM   22  O6  UNL     1      -4.060  -0.033  -2.765  1.00  0.00           O  
HETATM   23  C16 UNL     1      -3.906   1.792  -1.262  1.00  0.00           C  
HETATM   24  C17 UNL     1      -4.869   1.531  -0.106  1.00  0.00           C  
HETATM   25  C18 UNL     1      -6.228   1.362  -0.695  1.00  0.00           C  
HETATM   26  C19 UNL     1      -7.096   0.336  -0.062  1.00  0.00           C  
HETATM   27  O7  UNL     1      -8.170   0.088  -0.950  1.00  0.00           O  
HETATM   28  C20 UNL     1      -6.270  -0.941  -0.041  1.00  0.00           C  
HETATM   29  C21 UNL     1      -5.202  -0.734   0.985  1.00  0.00           C  
HETATM   30  C22 UNL     1      -4.400   0.517   0.848  1.00  0.00           C  
HETATM   31  C23 UNL     1      -4.352   1.129   2.267  1.00  0.00           C  
HETATM   32  C24 UNL     1      -2.938   0.089   0.623  1.00  0.00           C  
HETATM   33  C25 UNL     1      -1.951   1.107   1.073  1.00  0.00           C  
HETATM   34  C26 UNL     1      -0.773   1.266   0.163  1.00  0.00           C  
HETATM   35  C27 UNL     1      -0.266  -0.016  -0.437  1.00  0.00           C  
HETATM   36  C28 UNL     1       0.648   0.358  -1.578  1.00  0.00           C  
HETATM   37  H1  UNL     1       0.853  -1.957   2.684  1.00  0.00           H  
HETATM   38  H2  UNL     1       2.246  -2.565   1.753  1.00  0.00           H  
HETATM   39  H3  UNL     1       2.454  -1.309   3.103  1.00  0.00           H  
HETATM   40  H4  UNL     1       1.574   0.374   1.844  1.00  0.00           H  
HETATM   41  H5  UNL     1       2.838   0.388  -0.291  1.00  0.00           H  
HETATM   42  H6  UNL     1       3.045  -1.385  -0.207  1.00  0.00           H  
HETATM   43  H7  UNL     1       4.223  -1.044   2.020  1.00  0.00           H  
HETATM   44  H8  UNL     1       4.036   0.702   1.798  1.00  0.00           H  
HETATM   45  H9  UNL     1       6.601   0.073   2.060  1.00  0.00           H  
HETATM   46  H10 UNL     1       8.542   0.684   0.896  1.00  0.00           H  
HETATM   47  H11 UNL     1       8.820   0.784  -1.389  1.00  0.00           H  
HETATM   48  H12 UNL     1       7.137   0.243  -1.783  1.00  0.00           H  
HETATM   49  H13 UNL     1       9.184   3.081  -0.597  1.00  0.00           H  
HETATM   50  H14 UNL     1      10.373  -1.988  -0.141  1.00  0.00           H  
HETATM   51  H15 UNL     1      -0.468  -1.067   1.365  1.00  0.00           H  
HETATM   52  H16 UNL     1       0.529  -3.061   0.547  1.00  0.00           H  
HETATM   53  H17 UNL     1       1.001  -2.253  -1.043  1.00  0.00           H  
HETATM   54  H18 UNL     1      -1.269  -3.042  -1.385  1.00  0.00           H  
HETATM   55  H19 UNL     1      -1.668  -2.557   0.332  1.00  0.00           H  
HETATM   56  H20 UNL     1      -1.264  -0.916  -2.163  1.00  0.00           H  
HETATM   57  H21 UNL     1      -3.424  -1.304  -0.876  1.00  0.00           H  
HETATM   58  H22 UNL     1      -2.339   0.927  -2.367  1.00  0.00           H  
HETATM   59  H23 UNL     1      -3.670  -0.925  -2.929  1.00  0.00           H  
HETATM   60  H24 UNL     1      -4.499   2.241  -2.116  1.00  0.00           H  
HETATM   61  H25 UNL     1      -3.183   2.624  -1.015  1.00  0.00           H  
HETATM   62  H26 UNL     1      -4.904   2.542   0.415  1.00  0.00           H  
HETATM   63  H27 UNL     1      -6.828   2.321  -0.725  1.00  0.00           H  
HETATM   64  H28 UNL     1      -6.145   1.082  -1.786  1.00  0.00           H  
HETATM   65  H29 UNL     1      -7.513   0.602   0.907  1.00  0.00           H  
HETATM   66  H30 UNL     1      -7.877  -0.578  -1.639  1.00  0.00           H  
HETATM   67  H31 UNL     1      -5.915  -1.119  -1.054  1.00  0.00           H  
HETATM   68  H32 UNL     1      -6.915  -1.766   0.302  1.00  0.00           H  
HETATM   69  H33 UNL     1      -4.558  -1.665   0.954  1.00  0.00           H  
HETATM   70  H34 UNL     1      -5.719  -0.832   1.987  1.00  0.00           H  
HETATM   71  H35 UNL     1      -4.230   2.220   2.171  1.00  0.00           H  
HETATM   72  H36 UNL     1      -3.593   0.648   2.883  1.00  0.00           H  
HETATM   73  H37 UNL     1      -5.351   0.946   2.728  1.00  0.00           H  
HETATM   74  H38 UNL     1      -2.825  -0.809   1.304  1.00  0.00           H  
HETATM   75  H39 UNL     1      -1.543   0.865   2.098  1.00  0.00           H  
HETATM   76  H40 UNL     1      -2.409   2.128   1.202  1.00  0.00           H  
HETATM   77  H41 UNL     1       0.091   1.663   0.775  1.00  0.00           H  
HETATM   78  H42 UNL     1      -0.903   2.041  -0.626  1.00  0.00           H  
HETATM   79  H43 UNL     1       1.099   1.362  -1.481  1.00  0.00           H  
HETATM   80  H44 UNL     1       1.355  -0.444  -1.859  1.00  0.00           H  
HETATM   81  H45 UNL     1       0.018   0.469  -2.535  1.00  0.00           H  
CONECT    1    2   37   38   39
CONECT    2    3   16   40
CONECT    3    4   41   42
CONECT    4    5   43   44
CONECT    5    6    6    7
CONECT    7    8   45
CONECT    8    9   13   46
CONECT    9   10   47   48
CONECT   10   11   11   12
CONECT   12   49
CONECT   13   14   14   15
CONECT   15   50
CONECT   16   17   35   51
CONECT   17   18   52   53
CONECT   18   19   54   55
CONECT   19   20   35   56
CONECT   20   21   32   57
CONECT   21   22   23   58
CONECT   22   59
CONECT   23   24   60   61
CONECT   24   25   30   62
CONECT   25   26   63   64
CONECT   26   27   28   65
CONECT   27   66
CONECT   28   29   67   68
CONECT   29   30   69   70
CONECT   30   31   32
CONECT   31   71   72   73
CONECT   32   33   74
CONECT   33   34   75   76
CONECT   34   35   77   78
CONECT   35   36
CONECT   36   79   80   81
END

HMDB0242402
     RDKit          3D
Chenodeoxycholylaspartic acid
 81 84  0  0  0  0  0  0  0  0999 V2000
    1.8449   -1.6839    2.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6090   -0.5335    1.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8446   -0.5001    0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0843   -0.2499    1.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3101   -0.2192    0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1602   -0.3661   -0.8056 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5837   -0.0317    0.9944 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8268    0.0295    0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7497    0.7531   -1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3383    2.1343   -0.8143 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1786    2.4415   -0.4927 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2407    3.2067   -0.9482 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3895   -1.2951    0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8276   -2.3538    0.5016 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6049   -1.4671   -0.5556 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466   -0.8997    0.5706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3650   -2.2366   -0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1081   -2.2990   -0.5911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3690   -0.8781   -1.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7488   -0.4006   -0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2512    0.5766   -1.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0597   -0.0333   -2.7653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9063    1.7924   -1.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8694    1.5312   -0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2280    1.3623   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0965    0.3359   -0.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1696    0.0883   -0.9499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2701   -0.9413   -0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2023   -0.7336    0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3996    0.5167    0.8477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3516    1.1287    2.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9379    0.0887    0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9512    1.1066    1.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7732    1.2661    0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2663   -0.0163   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6480    0.3581   -1.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8525   -1.9569    2.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2463   -2.5647    1.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4544   -1.3093    3.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5740    0.3744    1.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8378    0.3880   -0.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0454   -1.3847   -0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2232   -1.0442    2.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0362    0.7021    1.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6006    0.0733    2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5417    0.6839    0.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8204    0.7839   -1.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1370    0.2427   -1.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1844    3.0808   -0.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3727   -1.9879   -0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4682   -1.0672    1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5289   -3.0608    0.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008   -2.2534   -1.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2685   -3.0416   -1.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676   -2.5568    0.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640   -0.9156   -2.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4236   -1.3043   -0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3390    0.9271   -2.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6704   -0.9251   -2.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4992    2.2407   -2.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1830    2.6236   -1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9041    2.5416    0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8279    2.3208   -0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1449    1.0818   -1.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5135    0.6015    0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8772   -0.5781   -1.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9151   -1.1189   -1.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9148   -1.7664    0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5577   -1.6649    0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7195   -0.8316    1.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2304    2.2198    2.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5928    0.6478    2.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3514    0.9462    2.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8252   -0.8089    1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5435    0.8648    2.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4088    2.1277    1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0910    1.6627    0.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9027    2.0410   -0.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0986    1.3623   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -0.4442   -1.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0181    0.4691   -2.5347 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  2  0
 10 12  1  0
  8 13  1  0
 13 14  2  0
 13 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 35 16  1  0
 35 19  1  0
 32 20  1  0
 30 24  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  7 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 12 49  1  0
 15 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 20 57  1  0
 21 58  1  0
 22 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 26 65  1  0
 27 66  1  0
 28 67  1  0
 28 68  1  0
 29 69  1  0
 29 70  1  0
 31 71  1  0
 31 72  1  0
 31 73  1  0
 32 74  1  0
 33 75  1  0
 33 76  1  0
 34 77  1  0
 34 78  1  0
 36 79  1  0
 36 80  1  0
 36 81  1  0
M  END

Synonyms

Value	Source
2-[(4-{5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl}-1-hydroxypentylidene)amino]butanedioate	Generator
Chenodeoxycholylaspartate	Generator
Asp-Chenodeoxycho	HMDB
Asp-CDCA	HMDB
Aspartochenodeoxycholic acid	HMDB
Aspartochenodeoxycholate	HMDB

Molecular Formula

C₂₈H₄₅NO₇

Average Mass

507.668

Monoisotopic Mass

507.319602793

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C28H45NO7/c1-15(4-7-23(32)29-21(26(35)36)14-24(33)34)18-5-6-19-25-20(9-11-28(18,19)3)27(2)10-8-17(30)12-16(27)13-22(25)31/h15-22,25,30-31H,4-14H2,1-3H3,(H,29,32)(H,33,34)(H,35,36)

InChI Key

TZJSDNVVGFIRIY-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
Aspartic acid or derivatives
Acyl-homoserine
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid or derivatives
Fatty acyl
N-acyl-amine
Fatty amide
Dicarboxylic acid or derivatives
Cyclic alcohol
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	0.0058 g/L	ALOGPS
logP	1.86	ALOGPS
logP	2.53	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	-0.47	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.16 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	132.61 m³·mol⁻¹	ChemAxon
Polarizability	57.31 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	splash10-0a4i-0003890000-bb4a37c0e07d3d9af4ef	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1109200000-74460e9dbebf555c0202	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00mt-9688000000-065eb15bdb1b385f7e64	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000920000-cde227237fc6d2750e49	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-2100920000-d9187bd79667a67d6d0f	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-7309400000-458ba0767e31d60982f5	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

Exposure Sources

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

HMDB0242402

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 Chenodeoxycholylaspartic acid (MMDBc0057247)

MOL for #<Metabolite:0x00007fdb3e21f0b8>

3D MOL for #<Metabolite:0x00007fdb3e21f0b8>

3D SDF for #<Metabolite:0x00007fdb3e21f0b8>

3D-SDF for #<Metabolite:0x00007fdb3e21f0b8>

PDB for #<Metabolite:0x00007fdb3e21f0b8>

3D PDB for #<Metabolite:0x00007fdb3e21f0b8>

SMILES for #<Metabolite:0x00007fdb3e21f0b8>

INCHI for #<Metabolite:0x00007fdb3e21f0b8>

Structure for #<Metabolite:0x00007fdb3e21f0b8>

3D Structure for #<Metabolite:0x00007fdb3e21f0b8>