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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-08-30 16:04:45 UTC

Update Date

2022-11-15 17:19:57 UTC

HMDB ID

HMDB0242370

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cholylalanine

Description

Cholylalanine 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. Cholylalanine consists of the bile acid cholic acid conjugated to the amino acid Alanine 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 Cholylalanine, 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 ). Cholylalanine 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

  Mrv1652308302118142D          

 34 37  0  0  0  0            999 V2000
    8.3550   -2.5302    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
    9.0694   -3.7677    0.0000 O   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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 16 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 12 32  1  0  0  0  0
 15 32  1  0  0  0  0
 32 33  1  0  0  0  0
  4 34  1  0  0  0  0
M  END

HMDB0242370
     RDKit          3D
Cholylalanine
 79 82  0  0  0  0  0  0  0  0999 V2000
    6.7876    3.2007   -1.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2887    2.1150   -0.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9391    0.9028   -1.2511 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6281    0.3844   -1.1653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    0.9584   -0.4862 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2975   -0.8407   -1.8806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9146   -1.3639   -1.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5151   -1.7192   -0.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4684   -2.8084    0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417   -2.2539   -0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9837   -2.5473    1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4741   -2.4280    1.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331   -1.9832    0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3358   -1.1807    0.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5368   -1.5812   -0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3231   -2.8095   -0.8137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9776   -0.5303   -1.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3604    0.7165   -0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7753    0.5551    0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2675    1.6417    0.9623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5219    2.8419    0.2942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3379    1.7884    2.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0933    0.9471    2.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4041    1.0848    0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0042    2.5629    0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1375    0.3013    0.7269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0908    0.8347   -0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2070    0.0810    0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5772    0.2073    1.3647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0043   -1.3281   -0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559   -1.3204   -1.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3325    1.8163    0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7863    0.6535    0.6254 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8433    2.8136    1.2783 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3773    2.7995   -2.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9546    3.8496   -1.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5095    3.8154   -0.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4037    2.4822   -0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6974    0.4512   -1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4102   -0.5976   -2.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0838   -1.6367   -1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2386   -0.6103   -2.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8888   -2.3269   -2.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6416   -0.8739    0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9727   -2.5159    1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2065   -3.0910   -0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9362   -3.7587    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9555   -3.2022   -0.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2678   -3.6158    1.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.8364    1.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9342   -3.3871    1.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6888   -1.6959    2.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4155   -2.9107   -0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6517   -1.4906    1.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4576   -1.7748    0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7308   -2.8542   -1.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3009   -0.3308   -1.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9215   -0.9302   -1.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3688    1.5472   -1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4192    0.5738   -0.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9858   -0.4268    0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2771    1.3055    1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0965    2.8804   -0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8439    1.4583    3.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1112    2.8638    2.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3276   -0.1085    2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3827    1.3199    2.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8392    3.2379    0.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2580    2.7408    1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118    2.7912   -0.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7005    0.5150    1.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8773    1.8915    0.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3686    0.8808   -1.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9705    0.5845   -0.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3405    1.1160    1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2930   -1.5971   -2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1165   -0.3017   -2.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3745   -2.0768   -2.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7986    3.1341    1.1246 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
  2 32  1  0
 32 33  2  0
 32 34  1  0
 30 10  1  0
 30 13  1  0
 26 14  1  0
 24 18  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  3 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 12 52  1  0
 13 53  1  0
 14 54  1  0
 15 55  1  0
 16 56  1  0
 17 57  1  0
 17 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 20 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  0
 23 67  1  0
 25 68  1  0
 25 69  1  0
 25 70  1  0
 26 71  1  0
 27 72  1  0
 27 73  1  0
 28 74  1  0
 29 75  1  0
 31 76  1  0
 31 77  1  0
 31 78  1  0
 34 79  1  0
M  END

  Mrv1652308302118142D          

 34 37  0  0  0  0            999 V2000
    8.3550   -2.5302    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
    9.0694   -3.7677    0.0000 O   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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 16 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 12 32  1  0  0  0  0
 15 32  1  0  0  0  0
 32 33  1  0  0  0  0
  4 34  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242370

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H45NO6/c1-14(5-8-23(32)28-15(2)25(33)34)18-6-7-19-24-20(13-22(31)27(18,19)4)26(3)10-9-17(29)11-16(26)12-21(24)30/h14-22,24,29-31H,5-13H2,1-4H3,(H,28,32)(H,33,34)

> <INCHI_KEY>
AZWGEBXBDOIOHW-UHFFFAOYSA-N

> <FORMULA>
C27H45NO6

> <MOLECULAR_WEIGHT>
479.658

> <EXACT_MASS>
479.324688173

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
54.635394819645285

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <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)propanoic acid

> <ALOGPS_LOGP>
1.92

> <JCHEM_LOGP>
1.9459754593333318

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.62717112144627

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.801325643427841

> <JCHEM_PKA_STRONGEST_BASIC>
-0.1313469400481745

> <JCHEM_POLAR_SURFACE_AREA>
127.09000000000002

> <JCHEM_REFRACTIVITY>
128.08669999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e-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)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242370
     RDKit          3D
Cholylalanine
 79 82  0  0  0  0  0  0  0  0999 V2000
    6.7876    3.2007   -1.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2887    2.1150   -0.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9391    0.9028   -1.2511 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6281    0.3844   -1.1653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    0.9584   -0.4862 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2975   -0.8407   -1.8806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9146   -1.3639   -1.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5151   -1.7192   -0.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4684   -2.8084    0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417   -2.2539   -0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9837   -2.5473    1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4741   -2.4280    1.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331   -1.9832    0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3358   -1.1807    0.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5368   -1.5812   -0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3231   -2.8095   -0.8137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9776   -0.5303   -1.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3604    0.7165   -0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7753    0.5551    0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2675    1.6417    0.9623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5219    2.8419    0.2942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3379    1.7884    2.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0933    0.9471    2.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4041    1.0848    0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0042    2.5629    0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1375    0.3013    0.7269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0908    0.8347   -0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2070    0.0810    0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5772    0.2073    1.3647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0043   -1.3281   -0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559   -1.3204   -1.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3325    1.8163    0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7863    0.6535    0.6254 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8433    2.8136    1.2783 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3773    2.7995   -2.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9546    3.8496   -1.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5095    3.8154   -0.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4037    2.4822   -0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6974    0.4512   -1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4102   -0.5976   -2.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0838   -1.6367   -1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2386   -0.6103   -2.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8888   -2.3269   -2.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6416   -0.8739    0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9727   -2.5159    1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2065   -3.0910   -0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9362   -3.7587    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9555   -3.2022   -0.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2678   -3.6158    1.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.8364    1.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9342   -3.3871    1.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6888   -1.6959    2.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4155   -2.9107   -0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6517   -1.4906    1.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4576   -1.7748    0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7308   -2.8542   -1.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3009   -0.3308   -1.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9215   -0.9302   -1.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3688    1.5472   -1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4192    0.5738   -0.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9858   -0.4268    0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2771    1.3055    1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0965    2.8804   -0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8439    1.4583    3.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1112    2.8638    2.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3276   -0.1085    2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3827    1.3199    2.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8392    3.2379    0.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2580    2.7408    1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118    2.7912   -0.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7005    0.5150    1.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8773    1.8915    0.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3686    0.8808   -1.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9705    0.5845   -0.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3405    1.1160    1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2930   -1.5971   -2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1165   -0.3017   -2.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3745   -2.0768   -2.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7986    3.1341    1.1246 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
  2 32  1  0
 32 33  2  0
 32 34  1  0
 30 10  1  0
 30 13  1  0
 26 14  1  0
 24 18  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  3 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 12 52  1  0
 13 53  1  0
 14 54  1  0
 15 55  1  0
 16 56  1  0
 17 57  1  0
 17 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 20 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  0
 23 67  1  0
 25 68  1  0
 25 69  1  0
 25 70  1  0
 26 71  1  0
 27 72  1  0
 27 73  1  0
 28 74  1  0
 29 75  1  0
 31 76  1  0
 31 77  1  0
 31 78  1  0
 34 79  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      15.596  -4.723   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      16.930  -5.493   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      16.930  -7.033   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      18.263  -4.723   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      19.597  -5.493   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      20.931  -4.723   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      20.931  -3.183   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      22.264  -5.493   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.598  -4.723   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.932  -5.493   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.932  -7.033   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.265  -4.723   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.426  -3.191   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.933  -2.871   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.703  -4.205   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.209  -4.525   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      31.239  -3.381   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      30.764  -1.916   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      32.746  -3.701   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      33.222  -5.166   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      34.728  -5.486   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      35.204  -6.950   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      36.710  -7.271   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      34.174  -8.095   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      32.667  -7.775   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      32.191  -6.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      31.161  -7.454   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      30.685  -5.990   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      29.654  -7.134   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      28.148  -6.814   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      27.118  -7.958   0.000  0.00  0.00           O+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
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   34                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   32                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   32                                                  
CONECT   16   15   17   28                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   20   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   16   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   12   15   33                                             
CONECT   33   32                                                            
CONECT   34    4                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

COMPND    HMDB0242370
HETATM    1  C1  UNL     1       6.788   3.201  -1.472  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.289   2.115  -0.551  1.00  0.00           C  
HETATM    3  N1  UNL     1       5.939   0.903  -1.251  1.00  0.00           N  
HETATM    4  C3  UNL     1       4.628   0.384  -1.165  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.746   0.958  -0.486  1.00  0.00           O  
HETATM    6  C4  UNL     1       4.298  -0.841  -1.881  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.915  -1.364  -1.726  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.515  -1.719  -0.335  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.468  -2.808   0.189  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.142  -2.254  -0.159  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.984  -2.547   1.341  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.474  -2.428   1.629  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.133  -1.983   0.339  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.336  -1.181   0.643  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.537  -1.581  -0.190  1.00  0.00           C  
HETATM   16  O2  UNL     1      -3.323  -2.810  -0.814  1.00  0.00           O  
HETATM   17  C14 UNL     1      -3.978  -0.530  -1.154  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.360   0.716  -0.394  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.775   0.555   0.069  1.00  0.00           C  
HETATM   20  C17 UNL     1      -6.267   1.642   0.962  1.00  0.00           C  
HETATM   21  O3  UNL     1      -6.522   2.842   0.294  1.00  0.00           O  
HETATM   22  C18 UNL     1      -5.338   1.788   2.120  1.00  0.00           C  
HETATM   23  C19 UNL     1      -4.093   0.947   2.014  1.00  0.00           C  
HETATM   24  C20 UNL     1      -3.404   1.085   0.674  1.00  0.00           C  
HETATM   25  C21 UNL     1      -3.004   2.563   0.559  1.00  0.00           C  
HETATM   26  C22 UNL     1      -2.138   0.301   0.727  1.00  0.00           C  
HETATM   27  C23 UNL     1      -1.091   0.835  -0.212  1.00  0.00           C  
HETATM   28  C24 UNL     1       0.207   0.081   0.032  1.00  0.00           C  
HETATM   29  O4  UNL     1       0.577   0.207   1.365  1.00  0.00           O  
HETATM   30  C25 UNL     1      -0.004  -1.328  -0.397  1.00  0.00           C  
HETATM   31  C26 UNL     1      -0.256  -1.320  -1.906  1.00  0.00           C  
HETATM   32  C27 UNL     1       7.332   1.816   0.467  1.00  0.00           C  
HETATM   33  O5  UNL     1       7.786   0.654   0.625  1.00  0.00           O  
HETATM   34  O6  UNL     1       7.843   2.814   1.278  1.00  0.00           O  
HETATM   35  H1  UNL     1       7.377   2.799  -2.319  1.00  0.00           H  
HETATM   36  H2  UNL     1       5.955   3.850  -1.781  1.00  0.00           H  
HETATM   37  H3  UNL     1       7.510   3.815  -0.861  1.00  0.00           H  
HETATM   38  H4  UNL     1       5.404   2.482  -0.010  1.00  0.00           H  
HETATM   39  H5  UNL     1       6.697   0.451  -1.807  1.00  0.00           H  
HETATM   40  H6  UNL     1       4.410  -0.598  -2.982  1.00  0.00           H  
HETATM   41  H7  UNL     1       5.084  -1.637  -1.734  1.00  0.00           H  
HETATM   42  H8  UNL     1       2.239  -0.610  -2.179  1.00  0.00           H  
HETATM   43  H9  UNL     1       2.889  -2.327  -2.322  1.00  0.00           H  
HETATM   44  H10 UNL     1       2.642  -0.874   0.365  1.00  0.00           H  
HETATM   45  H11 UNL     1       3.973  -2.516   1.118  1.00  0.00           H  
HETATM   46  H12 UNL     1       4.207  -3.091  -0.617  1.00  0.00           H  
HETATM   47  H13 UNL     1       2.936  -3.759   0.404  1.00  0.00           H  
HETATM   48  H14 UNL     1       0.955  -3.202  -0.672  1.00  0.00           H  
HETATM   49  H15 UNL     1       1.268  -3.616   1.561  1.00  0.00           H  
HETATM   50  H16 UNL     1       1.527  -1.836   1.967  1.00  0.00           H  
HETATM   51  H17 UNL     1      -0.934  -3.387   1.988  1.00  0.00           H  
HETATM   52  H18 UNL     1      -0.689  -1.696   2.460  1.00  0.00           H  
HETATM   53  H19 UNL     1      -1.415  -2.911  -0.225  1.00  0.00           H  
HETATM   54  H20 UNL     1      -2.652  -1.491   1.695  1.00  0.00           H  
HETATM   55  H21 UNL     1      -4.458  -1.775   0.445  1.00  0.00           H  
HETATM   56  H22 UNL     1      -3.731  -2.854  -1.718  1.00  0.00           H  
HETATM   57  H23 UNL     1      -3.301  -0.331  -1.994  1.00  0.00           H  
HETATM   58  H24 UNL     1      -4.922  -0.930  -1.632  1.00  0.00           H  
HETATM   59  H25 UNL     1      -4.369   1.547  -1.160  1.00  0.00           H  
HETATM   60  H26 UNL     1      -6.419   0.574  -0.858  1.00  0.00           H  
HETATM   61  H27 UNL     1      -5.986  -0.427   0.539  1.00  0.00           H  
HETATM   62  H28 UNL     1      -7.277   1.306   1.343  1.00  0.00           H  
HETATM   63  H29 UNL     1      -6.096   2.880  -0.599  1.00  0.00           H  
HETATM   64  H30 UNL     1      -5.844   1.458   3.075  1.00  0.00           H  
HETATM   65  H31 UNL     1      -5.111   2.864   2.287  1.00  0.00           H  
HETATM   66  H32 UNL     1      -4.328  -0.108   2.208  1.00  0.00           H  
HETATM   67  H33 UNL     1      -3.383   1.320   2.786  1.00  0.00           H  
HETATM   68  H34 UNL     1      -3.839   3.238   0.739  1.00  0.00           H  
HETATM   69  H35 UNL     1      -2.258   2.741   1.362  1.00  0.00           H  
HETATM   70  H36 UNL     1      -2.612   2.791  -0.456  1.00  0.00           H  
HETATM   71  H37 UNL     1      -1.700   0.515   1.754  1.00  0.00           H  
HETATM   72  H38 UNL     1      -0.877   1.891   0.126  1.00  0.00           H  
HETATM   73  H39 UNL     1      -1.369   0.881  -1.253  1.00  0.00           H  
HETATM   74  H40 UNL     1       0.970   0.584  -0.565  1.00  0.00           H  
HETATM   75  H41 UNL     1       0.340   1.116   1.704  1.00  0.00           H  
HETATM   76  H42 UNL     1      -1.293  -1.597  -2.166  1.00  0.00           H  
HETATM   77  H43 UNL     1      -0.116  -0.302  -2.320  1.00  0.00           H  
HETATM   78  H44 UNL     1       0.375  -2.077  -2.419  1.00  0.00           H  
HETATM   79  H45 UNL     1       8.799   3.134   1.125  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3   32   38
CONECT    3    4   39
CONECT    4    5    5    6
CONECT    6    7   40   41
CONECT    7    8   42   43
CONECT    8    9   10   44
CONECT    9   45   46   47
CONECT   10   11   30   48
CONECT   11   12   49   50
CONECT   12   13   51   52
CONECT   13   14   30   53
CONECT   14   15   26   54
CONECT   15   16   17   55
CONECT   16   56
CONECT   17   18   57   58
CONECT   18   19   24   59
CONECT   19   20   60   61
CONECT   20   21   22   62
CONECT   21   63
CONECT   22   23   64   65
CONECT   23   24   66   67
CONECT   24   25   26
CONECT   25   68   69   70
CONECT   26   27   71
CONECT   27   28   72   73
CONECT   28   29   30   74
CONECT   29   75
CONECT   30   31
CONECT   31   76   77   78
CONECT   32   33   33   34
CONECT   34   79
END

HMDB0242370
     RDKit          3D
Cholylalanine
 79 82  0  0  0  0  0  0  0  0999 V2000
    6.7876    3.2007   -1.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2887    2.1150   -0.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9391    0.9028   -1.2511 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6281    0.3844   -1.1653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    0.9584   -0.4862 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2975   -0.8407   -1.8806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9146   -1.3639   -1.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5151   -1.7192   -0.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4684   -2.8084    0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417   -2.2539   -0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9837   -2.5473    1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4741   -2.4280    1.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331   -1.9832    0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3358   -1.1807    0.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5368   -1.5812   -0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3231   -2.8095   -0.8137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9776   -0.5303   -1.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3604    0.7165   -0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7753    0.5551    0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2675    1.6417    0.9623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5219    2.8419    0.2942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3379    1.7884    2.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0933    0.9471    2.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4041    1.0848    0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0042    2.5629    0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1375    0.3013    0.7269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0908    0.8347   -0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2070    0.0810    0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5772    0.2073    1.3647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0043   -1.3281   -0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559   -1.3204   -1.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3325    1.8163    0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7863    0.6535    0.6254 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8433    2.8136    1.2783 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3773    2.7995   -2.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9546    3.8496   -1.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5095    3.8154   -0.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4037    2.4822   -0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6974    0.4512   -1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4102   -0.5976   -2.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0838   -1.6367   -1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2386   -0.6103   -2.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8888   -2.3269   -2.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6416   -0.8739    0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9727   -2.5159    1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2065   -3.0910   -0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9362   -3.7587    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9555   -3.2022   -0.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2678   -3.6158    1.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.8364    1.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9342   -3.3871    1.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6888   -1.6959    2.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4155   -2.9107   -0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6517   -1.4906    1.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4576   -1.7748    0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7308   -2.8542   -1.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3009   -0.3308   -1.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9215   -0.9302   -1.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3688    1.5472   -1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4192    0.5738   -0.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9858   -0.4268    0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2771    1.3055    1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0965    2.8804   -0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8439    1.4583    3.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1112    2.8638    2.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3276   -0.1085    2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3827    1.3199    2.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8392    3.2379    0.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2580    2.7408    1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118    2.7912   -0.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7005    0.5150    1.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8773    1.8915    0.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3686    0.8808   -1.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9705    0.5845   -0.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3405    1.1160    1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2930   -1.5971   -2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1165   -0.3017   -2.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3745   -2.0768   -2.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7986    3.1341    1.1246 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
  2 32  1  0
 32 33  2  0
 32 34  1  0
 30 10  1  0
 30 13  1  0
 26 14  1  0
 24 18  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  3 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 12 52  1  0
 13 53  1  0
 14 54  1  0
 15 55  1  0
 16 56  1  0
 17 57  1  0
 17 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 20 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  0
 23 67  1  0
 25 68  1  0
 25 69  1  0
 25 70  1  0
 26 71  1  0
 27 72  1  0
 27 73  1  0
 28 74  1  0
 29 75  1  0
 31 76  1  0
 31 77  1  0
 31 78  1  0
 34 79  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]propanoate	HMDB
Cholylalanine	HMDB
Ala-Cho	HMDB
Ala-CA	HMDB
Alanocholic acid	HMDB
Alanocholate	HMDB

Chemical Formula

C₂₇H₄₅NO₆

Average Molecular Weight

479.658

Monoisotopic Molecular Weight

479.324688173

IUPAC Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H45NO6/c1-14(5-8-23(32)28-15(2)25(33)34)18-6-7-19-24-20(13-22(31)27(18,19)4)26(3)10-9-17(29)11-16(26)12-21(24)30/h14-22,24,29-31H,5-13H2,1-4H3,(H,28,32)(H,33,34)

InChI Key

AZWGEBXBDOIOHW-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
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alanine or derivatives
Alpha-amino acid or derivatives
Fatty acyl
N-acyl-amine
Fatty amide
Cyclic alcohol
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Polyol
Monocarboxylic acid or derivatives
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	1.92	ALOGPS
logP	1.95	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	3.8	ChemAxon
pKa (Strongest Basic)	-0.13	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.09 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	128.09 m³·mol⁻¹	ChemAxon
Polarizability	54.64 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]-	239.228	30932474
DeepCCS	[M+Na]+	214.452	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cholylalanine	CC(CCC(=O)NC(C)C(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C	3373.9	Standard polar	33892256
Cholylalanine	CC(CCC(=O)NC(C)C(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C	2827.3	Standard non polar	33892256
Cholylalanine	CC(CCC(=O)NC(C)C(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C	4170.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cholylalanine,5TMS,isomer #1	CC(CCC(=O)N(C(C)C(=O)O[Si](C)(C)C)[Si](C)(C)C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O[Si](C)(C)C)C12C	3761.1	Semi standard non polar	33892256
Cholylalanine,5TMS,isomer #1	CC(CCC(=O)N(C(C)C(=O)O[Si](C)(C)C)[Si](C)(C)C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O[Si](C)(C)C)C12C	3781.8	Standard non polar	33892256
Cholylalanine,5TMS,isomer #1	CC(CCC(=O)N(C(C)C(=O)O[Si](C)(C)C)[Si](C)(C)C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CC(O[Si](C)(C)C)C12C	4018.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cholylalanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-0221900000-f3faee2f61731294c055	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholylalanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholylalanine 10V, Positive-QTOF	splash10-001i-0000900000-4d1ce43d0ffc658e8c70	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholylalanine 20V, Positive-QTOF	splash10-007o-4216900000-d3bea8cd6a5af2689b73	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholylalanine 40V, Positive-QTOF	splash10-052e-9622000000-e5dbcf3ec3340b177ade	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholylalanine 10V, Negative-QTOF	splash10-004i-0000900000-8b9f8d9b980a467e067b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholylalanine 20V, Negative-QTOF	splash10-0059-1001900000-8156657d21ba167c18fc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholylalanine 40V, Negative-QTOF	splash10-0173-6007900000-8e20d8639d492a134807	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

71058927

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 Cholylalanine (HMDB0242370)

MOL for HMDB0242370 (Cholylalanine)

3D MOL for HMDB0242370 (Cholylalanine)

3D SDF for HMDB0242370 (Cholylalanine)

3D-SDF for HMDB0242370 (Cholylalanine)

PDB for HMDB0242370 (Cholylalanine)

3D PDB for HMDB0242370 (Cholylalanine)

SMILES for HMDB0242370 (Cholylalanine)

INCHI for HMDB0242370 (Cholylalanine)

Structure for HMDB0242370 (Cholylalanine)

3D Structure for HMDB0242370 (Cholylalanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra