Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Predicted

Creation Date

2021-08-30 17:08:16 UTC

Update Date

2022-11-15 17:47:01 UTC

HMDB ID

HMDB0242381

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cholylaspartic acid

Description

Cholylaspartic 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. Cholylaspartic acid consists of the bile acid cholic 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 Cholylaspartic 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 ). Cholylaspartic 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


  Mrv1652308302119182D          

 37 40  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
   14.5273   -4.2635    0.0000 O   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
 31 33  1  0  0  0  0
 13 33  1  0  0  0  0
 16 33  1  0  0  0  0
 33 34  1  0  0  0  0
  5 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END

HMDB0242381
     RDKit          3D
Cholylaspartic acid
 82 85  0  0  0  0  0  0  0  0999 V2000
    1.4969    1.9678   -3.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0860    1.1476   -2.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9804    0.1391   -2.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6949   -0.7978   -1.9904 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6131   -0.1598   -1.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7560    1.0797   -1.0463 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3287   -0.9255   -0.0999 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2456   -0.2747    0.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8954   -0.7157    2.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6950   -0.1183    3.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5344    0.7872    3.1388 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5558   -0.5451    4.6593 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6275   -0.7474    0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8270   -1.5831   -0.4020 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7341   -0.3175    1.2288 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2179    0.8081   -1.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149    2.1086   -0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1367    1.5492    0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4462    0.0945    0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8199   -0.2413    0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0000   -1.5548    1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0559   -1.7072    2.2871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3751   -1.4541    1.9549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4704   -1.1349    0.9998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7487   -0.9825    1.7525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1775    0.4145    2.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7466    0.5811    3.2797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0624    1.4248    1.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3995    1.3532    0.5283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1871   -0.0237    0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1756   -0.2425   -1.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8199   -0.2844   -0.5668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4846    0.6775   -1.6337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0996    0.5738   -2.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1484   -0.2576   -3.3140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0446    0.0502   -1.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1723   -1.4327   -1.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0705    2.9233   -3.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9086    1.3778   -4.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4099    2.2777   -4.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8027    1.9170   -1.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8019    0.7397   -3.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5220   -0.3685   -3.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3559   -1.4438   -2.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0518   -1.5271   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2402   -1.9422   -0.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2160    0.8063    0.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8938   -1.8439    2.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8118   -0.4654    2.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2111   -0.3242    5.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4485   -1.0116    1.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8291    0.3293   -0.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2094    2.7719   -1.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5886    2.6224   -0.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0833    2.0708    0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3840    1.5236    1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2745   -0.5623    0.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1980    0.5333    1.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0766   -2.4144    0.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7495   -2.6452    2.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5808   -2.4981    2.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3428   -0.8240    2.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5987   -2.0604    0.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6014   -1.5019    1.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6620   -1.5067    2.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9656    0.7364    1.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3035   -0.2101    3.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5338    2.4269    1.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3278    1.3576    2.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0636    1.9623   -0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4742    1.9733    0.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8014   -0.9989   -1.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2919    0.7281   -1.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1719   -0.5625   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8937   -1.3136   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2142    0.5135   -2.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7300    1.7296   -1.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8417    1.6184   -2.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0255   -0.6761   -3.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7667   -1.9470   -1.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6170   -1.9725   -0.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8742   -1.5751   -2.4225 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
 34 36  1  0
 36 37  1  0
 36 16  1  0
 36 19  1  0
 32 20  1  0
 30 24  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  3 42  1  0
  3 43  1  0
  4 44  1  0
  4 45  1  0
  7 46  1  0
  8 47  1  0
  9 48  1  0
  9 49  1  0
 12 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  0
 20 58  1  0
 21 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 27 67  1  0
 28 68  1  0
 28 69  1  0
 29 70  1  0
 29 71  1  0
 31 72  1  0
 31 73  1  0
 31 74  1  0
 32 75  1  0
 33 76  1  0
 33 77  1  0
 34 78  1  0
 35 79  1  0
 37 80  1  0
 37 81  1  0
 37 82  1  0
M  END


  Mrv1652308302119182D          

 37 40  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
   14.5273   -4.2635    0.0000 O   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
 31 33  1  0  0  0  0
 13 33  1  0  0  0  0
 16 33  1  0  0  0  0
 33 34  1  0  0  0  0
  5 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242381

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CCC(=O)NC(CC(O)=O)C(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H45NO8/c1-14(4-7-23(33)29-20(26(36)37)13-24(34)35)17-5-6-18-25-19(12-22(32)28(17,18)3)27(2)9-8-16(30)10-15(27)11-21(25)31/h14-22,25,30-32H,4-13H2,1-3H3,(H,29,33)(H,34,35)(H,36,37)

> <INCHI_KEY>
VMFFESMCXOCOIZ-UHFFFAOYSA-N

> <FORMULA>
C28H45NO8

> <MOLECULAR_WEIGHT>
523.667

> <EXACT_MASS>
523.314517413

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
57.18684894006927

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-{5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)butanedioic acid

> <ALOGPS_LOGP>
1.34

> <JCHEM_LOGP>
1.3041635493333334

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.46294819276326

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5489981809745426

> <JCHEM_PKA_STRONGEST_BASIC>
-0.13226955847207578

> <JCHEM_POLAR_SURFACE_AREA>
164.39000000000001

> <JCHEM_REFRACTIVITY>
134.1221

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-{5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242381
     RDKit          3D
Cholylaspartic acid
 82 85  0  0  0  0  0  0  0  0999 V2000
    1.4969    1.9678   -3.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0860    1.1476   -2.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9804    0.1391   -2.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6949   -0.7978   -1.9904 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6131   -0.1598   -1.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7560    1.0797   -1.0463 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3287   -0.9255   -0.0999 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2456   -0.2747    0.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8954   -0.7157    2.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6950   -0.1183    3.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5344    0.7872    3.1388 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5558   -0.5451    4.6593 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6275   -0.7474    0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8270   -1.5831   -0.4020 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7341   -0.3175    1.2288 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2179    0.8081   -1.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149    2.1086   -0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1367    1.5492    0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4462    0.0945    0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8199   -0.2413    0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0000   -1.5548    1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0559   -1.7072    2.2871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3751   -1.4541    1.9549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4704   -1.1349    0.9998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7487   -0.9825    1.7525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1775    0.4145    2.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7466    0.5811    3.2797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0624    1.4248    1.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3995    1.3532    0.5283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1871   -0.0237    0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1756   -0.2425   -1.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8199   -0.2844   -0.5668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4846    0.6775   -1.6337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0996    0.5738   -2.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1484   -0.2576   -3.3140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0446    0.0502   -1.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1723   -1.4327   -1.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0705    2.9233   -3.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9086    1.3778   -4.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4099    2.2777   -4.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8027    1.9170   -1.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8019    0.7397   -3.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5220   -0.3685   -3.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3559   -1.4438   -2.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0518   -1.5271   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2402   -1.9422   -0.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2160    0.8063    0.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8938   -1.8439    2.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8118   -0.4654    2.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2111   -0.3242    5.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4485   -1.0116    1.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8291    0.3293   -0.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2094    2.7719   -1.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5886    2.6224   -0.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0833    2.0708    0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3840    1.5236    1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2745   -0.5623    0.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1980    0.5333    1.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0766   -2.4144    0.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7495   -2.6452    2.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5808   -2.4981    2.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3428   -0.8240    2.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5987   -2.0604    0.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6014   -1.5019    1.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6620   -1.5067    2.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9656    0.7364    1.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3035   -0.2101    3.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5338    2.4269    1.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3278    1.3576    2.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0636    1.9623   -0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4742    1.9733    0.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8014   -0.9989   -1.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2919    0.7281   -1.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1719   -0.5625   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8937   -1.3136   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2142    0.5135   -2.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7300    1.7296   -1.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8417    1.6184   -2.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0255   -0.6761   -3.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7667   -1.9470   -1.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6170   -1.9725   -0.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8742   -1.5751   -2.4225 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
 34 36  1  0
 36 37  1  0
 36 16  1  0
 36 19  1  0
 32 20  1  0
 30 24  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  3 42  1  0
  3 43  1  0
  4 44  1  0
  4 45  1  0
  7 46  1  0
  8 47  1  0
  9 48  1  0
  9 49  1  0
 12 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  0
 20 58  1  0
 21 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 27 67  1  0
 28 68  1  0
 28 69  1  0
 29 70  1  0
 29 71  1  0
 31 72  1  0
 31 73  1  0
 31 74  1  0
 32 75  1  0
 33 76  1  0
 33 77  1  0
 34 78  1  0
 35 79  1  0
 37 80  1  0
 37 81  1  0
 37 82  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  O   UNK     0      27.118  -7.958   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      27.672  -5.349   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      26.528  -6.380   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      18.263  -3.183   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      19.597  -2.413   0.000  0.00  0.00           O+0
HETATM   37  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   35                                                  
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   33                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   33                                                  
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   33                                                  
CONECT   32   31                                                            
CONECT   33   31   13   16   34                                             
CONECT   34   33                                                            
CONECT   35    5   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

COMPND    HMDB0242381
HETATM    1  C1  UNL     1       1.497   1.968  -3.403  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.086   1.148  -2.269  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.980   0.139  -2.892  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.695  -0.798  -1.990  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.613  -0.160  -1.031  1.00  0.00           C  
HETATM    6  O1  UNL     1       4.756   1.080  -1.046  1.00  0.00           O  
HETATM    7  N1  UNL     1       5.329  -0.925  -0.100  1.00  0.00           N  
HETATM    8  C6  UNL     1       6.246  -0.275   0.859  1.00  0.00           C  
HETATM    9  C7  UNL     1       5.895  -0.716   2.246  1.00  0.00           C  
HETATM   10  C8  UNL     1       6.695  -0.118   3.324  1.00  0.00           C  
HETATM   11  O2  UNL     1       7.534   0.787   3.139  1.00  0.00           O  
HETATM   12  O3  UNL     1       6.556  -0.545   4.659  1.00  0.00           O  
HETATM   13  C9  UNL     1       7.627  -0.747   0.541  1.00  0.00           C  
HETATM   14  O4  UNL     1       7.827  -1.583  -0.402  1.00  0.00           O  
HETATM   15  O5  UNL     1       8.734  -0.317   1.229  1.00  0.00           O  
HETATM   16  C10 UNL     1       1.218   0.808  -1.179  1.00  0.00           C  
HETATM   17  C11 UNL     1       0.715   2.109  -0.525  1.00  0.00           C  
HETATM   18  C12 UNL     1      -0.137   1.549   0.570  1.00  0.00           C  
HETATM   19  C13 UNL     1      -0.446   0.094   0.204  1.00  0.00           C  
HETATM   20  C14 UNL     1      -1.820  -0.241   0.532  1.00  0.00           C  
HETATM   21  C15 UNL     1      -2.000  -1.555   1.305  1.00  0.00           C  
HETATM   22  O6  UNL     1      -1.056  -1.707   2.287  1.00  0.00           O  
HETATM   23  C16 UNL     1      -3.375  -1.454   1.955  1.00  0.00           C  
HETATM   24  C17 UNL     1      -4.470  -1.135   1.000  1.00  0.00           C  
HETATM   25  C18 UNL     1      -5.749  -0.982   1.752  1.00  0.00           C  
HETATM   26  C19 UNL     1      -6.177   0.415   2.019  1.00  0.00           C  
HETATM   27  O7  UNL     1      -6.747   0.581   3.280  1.00  0.00           O  
HETATM   28  C20 UNL     1      -5.062   1.425   1.888  1.00  0.00           C  
HETATM   29  C21 UNL     1      -4.400   1.353   0.528  1.00  0.00           C  
HETATM   30  C22 UNL     1      -4.187  -0.024   0.028  1.00  0.00           C  
HETATM   31  C23 UNL     1      -5.176  -0.242  -1.133  1.00  0.00           C  
HETATM   32  C24 UNL     1      -2.820  -0.284  -0.567  1.00  0.00           C  
HETATM   33  C25 UNL     1      -2.485   0.678  -1.634  1.00  0.00           C  
HETATM   34  C26 UNL     1      -1.100   0.574  -2.168  1.00  0.00           C  
HETATM   35  O8  UNL     1      -1.148  -0.258  -3.314  1.00  0.00           O  
HETATM   36  C27 UNL     1      -0.045   0.050  -1.280  1.00  0.00           C  
HETATM   37  C28 UNL     1       0.172  -1.433  -1.577  1.00  0.00           C  
HETATM   38  H1  UNL     1       1.071   2.923  -3.082  1.00  0.00           H  
HETATM   39  H2  UNL     1       0.909   1.378  -4.114  1.00  0.00           H  
HETATM   40  H3  UNL     1       2.410   2.278  -4.009  1.00  0.00           H  
HETATM   41  H4  UNL     1       2.803   1.917  -1.822  1.00  0.00           H  
HETATM   42  H5  UNL     1       3.802   0.740  -3.405  1.00  0.00           H  
HETATM   43  H6  UNL     1       2.522  -0.369  -3.780  1.00  0.00           H  
HETATM   44  H7  UNL     1       4.356  -1.444  -2.649  1.00  0.00           H  
HETATM   45  H8  UNL     1       3.052  -1.527  -1.458  1.00  0.00           H  
HETATM   46  H9  UNL     1       5.240  -1.942  -0.056  1.00  0.00           H  
HETATM   47  H10 UNL     1       6.216   0.806   0.701  1.00  0.00           H  
HETATM   48  H11 UNL     1       5.894  -1.844   2.303  1.00  0.00           H  
HETATM   49  H12 UNL     1       4.812  -0.465   2.464  1.00  0.00           H  
HETATM   50  H13 UNL     1       7.211  -0.324   5.372  1.00  0.00           H  
HETATM   51  H14 UNL     1       9.448  -1.012   1.462  1.00  0.00           H  
HETATM   52  H15 UNL     1       1.829   0.329  -0.365  1.00  0.00           H  
HETATM   53  H16 UNL     1       0.209   2.772  -1.219  1.00  0.00           H  
HETATM   54  H17 UNL     1       1.589   2.622  -0.029  1.00  0.00           H  
HETATM   55  H18 UNL     1      -1.083   2.071   0.715  1.00  0.00           H  
HETATM   56  H19 UNL     1       0.384   1.524   1.561  1.00  0.00           H  
HETATM   57  H20 UNL     1       0.275  -0.562   0.721  1.00  0.00           H  
HETATM   58  H21 UNL     1      -2.198   0.533   1.272  1.00  0.00           H  
HETATM   59  H22 UNL     1      -2.077  -2.414   0.603  1.00  0.00           H  
HETATM   60  H23 UNL     1      -0.749  -2.645   2.419  1.00  0.00           H  
HETATM   61  H24 UNL     1      -3.581  -2.498   2.341  1.00  0.00           H  
HETATM   62  H25 UNL     1      -3.343  -0.824   2.858  1.00  0.00           H  
HETATM   63  H26 UNL     1      -4.599  -2.060   0.356  1.00  0.00           H  
HETATM   64  H27 UNL     1      -6.601  -1.502   1.225  1.00  0.00           H  
HETATM   65  H28 UNL     1      -5.662  -1.507   2.732  1.00  0.00           H  
HETATM   66  H29 UNL     1      -6.966   0.736   1.277  1.00  0.00           H  
HETATM   67  H30 UNL     1      -7.304  -0.210   3.538  1.00  0.00           H  
HETATM   68  H31 UNL     1      -5.534   2.427   1.994  1.00  0.00           H  
HETATM   69  H32 UNL     1      -4.328   1.358   2.723  1.00  0.00           H  
HETATM   70  H33 UNL     1      -5.064   1.962  -0.157  1.00  0.00           H  
HETATM   71  H34 UNL     1      -3.474   1.973   0.608  1.00  0.00           H  
HETATM   72  H35 UNL     1      -4.801  -0.999  -1.822  1.00  0.00           H  
HETATM   73  H36 UNL     1      -5.292   0.728  -1.650  1.00  0.00           H  
HETATM   74  H37 UNL     1      -6.172  -0.563  -0.728  1.00  0.00           H  
HETATM   75  H38 UNL     1      -2.894  -1.314  -1.015  1.00  0.00           H  
HETATM   76  H39 UNL     1      -3.214   0.514  -2.482  1.00  0.00           H  
HETATM   77  H40 UNL     1      -2.730   1.730  -1.298  1.00  0.00           H  
HETATM   78  H41 UNL     1      -0.842   1.618  -2.513  1.00  0.00           H  
HETATM   79  H42 UNL     1      -2.025  -0.676  -3.424  1.00  0.00           H  
HETATM   80  H43 UNL     1      -0.767  -1.947  -1.852  1.00  0.00           H  
HETATM   81  H44 UNL     1       0.617  -1.973  -0.729  1.00  0.00           H  
HETATM   82  H45 UNL     1       0.874  -1.575  -2.422  1.00  0.00           H  
CONECT    1    2   38   39   40
CONECT    2    3   16   41
CONECT    3    4   42   43
CONECT    4    5   44   45
CONECT    5    6    6    7
CONECT    7    8   46
CONECT    8    9   13   47
CONECT    9   10   48   49
CONECT   10   11   11   12
CONECT   12   50
CONECT   13   14   14   15
CONECT   15   51
CONECT   16   17   36   52
CONECT   17   18   53   54
CONECT   18   19   55   56
CONECT   19   20   36   57
CONECT   20   21   32   58
CONECT   21   22   23   59
CONECT   22   60
CONECT   23   24   61   62
CONECT   24   25   30   63
CONECT   25   26   64   65
CONECT   26   27   28   66
CONECT   27   67
CONECT   28   29   68   69
CONECT   29   30   70   71
CONECT   30   31   32
CONECT   31   72   73   74
CONECT   32   33   75
CONECT   33   34   76   77
CONECT   34   35   36   78
CONECT   35   79
CONECT   36   37
CONECT   37   80   81   82
END

HMDB0242381
     RDKit          3D
Cholylaspartic acid
 82 85  0  0  0  0  0  0  0  0999 V2000
    1.4969    1.9678   -3.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0860    1.1476   -2.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9804    0.1391   -2.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6949   -0.7978   -1.9904 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6131   -0.1598   -1.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7560    1.0797   -1.0463 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3287   -0.9255   -0.0999 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2456   -0.2747    0.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8954   -0.7157    2.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6950   -0.1183    3.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5344    0.7872    3.1388 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5558   -0.5451    4.6593 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6275   -0.7474    0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8270   -1.5831   -0.4020 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7341   -0.3175    1.2288 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2179    0.8081   -1.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149    2.1086   -0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1367    1.5492    0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4462    0.0945    0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8199   -0.2413    0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0000   -1.5548    1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0559   -1.7072    2.2871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3751   -1.4541    1.9549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4704   -1.1349    0.9998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7487   -0.9825    1.7525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1775    0.4145    2.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7466    0.5811    3.2797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0624    1.4248    1.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3995    1.3532    0.5283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1871   -0.0237    0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1756   -0.2425   -1.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8199   -0.2844   -0.5668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4846    0.6775   -1.6337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0996    0.5738   -2.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1484   -0.2576   -3.3140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0446    0.0502   -1.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1723   -1.4327   -1.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0705    2.9233   -3.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9086    1.3778   -4.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4099    2.2777   -4.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8027    1.9170   -1.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8019    0.7397   -3.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5220   -0.3685   -3.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3559   -1.4438   -2.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0518   -1.5271   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2402   -1.9422   -0.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2160    0.8063    0.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8938   -1.8439    2.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8118   -0.4654    2.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2111   -0.3242    5.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4485   -1.0116    1.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8291    0.3293   -0.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2094    2.7719   -1.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5886    2.6224   -0.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0833    2.0708    0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3840    1.5236    1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2745   -0.5623    0.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1980    0.5333    1.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0766   -2.4144    0.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7495   -2.6452    2.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5808   -2.4981    2.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3428   -0.8240    2.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5987   -2.0604    0.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6014   -1.5019    1.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6620   -1.5067    2.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9656    0.7364    1.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3035   -0.2101    3.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5338    2.4269    1.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3278    1.3576    2.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0636    1.9623   -0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4742    1.9733    0.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8014   -0.9989   -1.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2919    0.7281   -1.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1719   -0.5625   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8937   -1.3136   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2142    0.5135   -2.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7300    1.7296   -1.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8417    1.6184   -2.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0255   -0.6761   -3.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7667   -1.9470   -1.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6170   -1.9725   -0.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8742   -1.5751   -2.4225 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
 34 36  1  0
 36 37  1  0
 36 16  1  0
 36 19  1  0
 32 20  1  0
 30 24  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  3 42  1  0
  3 43  1  0
  4 44  1  0
  4 45  1  0
  7 46  1  0
  8 47  1  0
  9 48  1  0
  9 49  1  0
 12 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  0
 20 58  1  0
 21 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 27 67  1  0
 28 68  1  0
 28 69  1  0
 29 70  1  0
 29 71  1  0
 31 72  1  0
 31 73  1  0
 31 74  1  0
 32 75  1  0
 33 76  1  0
 33 77  1  0
 34 78  1  0
 35 79  1  0
 37 80  1  0
 37 81  1  0
 37 82  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-[(1-Hydroxy-4-{5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl}pentylidene)amino]butanedioate	Generator
Cholylaspartate	Generator

Chemical Formula

C₂₈H₄₅NO₈

Average Molecular Weight

523.667

Monoisotopic Molecular Weight

523.314517413

IUPAC Name

2-(4-{5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)butanedioic acid

Traditional Name

2-(4-{5,9,16-trihydroxy-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)C3CC(O)C12C

InChI Identifier

InChI=1S/C28H45NO8/c1-14(4-7-23(33)29-20(26(36)37)13-24(34)35)17-5-6-18-25-19(12-22(32)28(17,18)3)27(2)9-8-16(30)10-15(27)11-21(25)31/h14-22,25,30-32H,4-13H2,1-3H3,(H,29,33)(H,34,35)(H,36,37)

InChI Key

VMFFESMCXOCOIZ-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
Trihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
7-hydroxysteroid
Hydroxysteroid
12-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
Polyol
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

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.34	ALOGPS
logP	1.3	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	-0.13	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.39 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	134.12 m³·mol⁻¹	ChemAxon
Polarizability	57.19 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	244.587	30932474
DeepCCS	[M+Na]+	220.012	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cholylaspartic acid	CC(CCC(=O)NC(CC(O)=O)C(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C	3747.5	Standard polar	33892256
Cholylaspartic acid	CC(CCC(=O)NC(CC(O)=O)C(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C	3122.8	Standard non polar	33892256
Cholylaspartic acid	CC(CCC(=O)NC(CC(O)=O)C(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C	4558.5	Semi standard non polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholylaspartic acid 10V, Negative-QTOF	splash10-0udr-0100980000-1ece05f51ea988856152	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholylaspartic acid 20V, Negative-QTOF	splash10-01p9-3100930000-f002b749a42699e3058c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholylaspartic acid 40V, Negative-QTOF	splash10-052o-7109800000-26422a98b6b37778cc15	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholylaspartic acid 10V, Positive-QTOF	splash10-00di-0002490000-fafb1c7be26c7c5ce6f8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholylaspartic acid 20V, Positive-QTOF	splash10-00di-0109210000-d3846e111ab7c1a66421	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholylaspartic acid 40V, Positive-QTOF	splash10-02bs-9833000000-07afb99e3c1a345a6587	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Intestine

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

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 Cholylaspartic acid (HMDB0242381)

MOL for HMDB0242381 (Cholylaspartic acid)

3D MOL for HMDB0242381 (Cholylaspartic acid)

3D SDF for HMDB0242381 (Cholylaspartic acid)

3D-SDF for HMDB0242381 (Cholylaspartic acid)

PDB for HMDB0242381 (Cholylaspartic acid)

3D PDB for HMDB0242381 (Cholylaspartic acid)

SMILES for HMDB0242381 (Cholylaspartic acid)

INCHI for HMDB0242381 (Cholylaspartic acid)

Structure for HMDB0242381 (Cholylaspartic acid)

3D Structure for HMDB0242381 (Cholylaspartic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

MS/MS Spectra