MiMeDB: Showing metabocard for Deoxycholylalanine (MMDBc0057257)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-11-10 23:37:44 UTC

Update Date

2024-04-30 20:57:01 UTC

Metabolite ID

MMDBc0057257

Metabolite Identification

Common Name

Deoxycholylalanine

Description

Deoxycholylalanine 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. Deoxycholylalanine consists of the bile acid deoxycholic 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 Deoxycholylalanine, 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 ). Deoxycholylalanine 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


  Mrv1652308302121382D          

 33 36  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
   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
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 12 31  1  0  0  0  0
 15 31  1  0  0  0  0
 31 32  1  0  0  0  0
  4 33  1  0  0  0  0
M  END

HMDB0242412
     RDKit          3D
Deoxycholylalanine
 78 81  0  0  0  0  0  0  0  0999 V2000
    6.8902    1.0807   -0.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3601    1.0267   -0.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9229   -0.1020    0.1634 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1409   -1.1080   -0.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8407   -1.0011   -1.6625 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6845   -2.2875    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -3.1467   -0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5047   -2.6406   -0.9907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9610   -3.8975   -1.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4085   -2.2545   -0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0984   -3.3418    0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4696   -2.7500    1.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1262   -1.2972    1.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2580   -0.3767    1.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1590   -0.8082   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3166    0.1310   -0.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0228    1.5704   -0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7987    2.0413   -1.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8535    3.5417   -1.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0620    3.8802   -0.9002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7407    4.0566   -0.7134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5192    3.4142    0.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9796    2.0190    0.7942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7036    2.0007    2.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370    1.0566    0.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6785    1.3198    0.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0135    0.0957   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3301    0.4690   -0.8126 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1804   -1.0102    0.5768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1433   -0.5282    1.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792    2.3171   -0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1740    2.3408    1.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1931    3.5328   -0.5975 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2153    0.0117   -0.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2072    1.6938   -1.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2454    1.4639    0.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9990    0.9596   -1.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1799   -0.1941    1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4279   -2.0267    1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6420   -2.9351    0.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6474   -4.0958    0.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4470   -3.5514   -1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7108   -1.9371   -1.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0900   -4.7735   -1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1252   -3.7648   -1.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4582   -3.9663   -2.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5467   -2.2516   -0.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5062   -3.3846    1.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2489   -4.3028    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0261   -2.9351    0.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9605   -3.2217    1.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9322   -1.2475    2.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9407   -0.4255    1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6223   -1.7881    0.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7078   -0.9088   -1.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9044   -0.1269   -1.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9652   -0.0706    0.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9826    2.0969    0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7192    1.7194   -2.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9600    1.6096   -2.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8341    4.0231   -2.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0735    4.8335   -0.6339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9429    5.1647   -0.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210    4.0752   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799    4.1249    1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000    3.4193    0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4567    2.8137    2.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9829    2.1193    2.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2800    1.0616    2.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4489    1.2595    2.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9558    1.9128   -0.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0984    1.9471    0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4141   -0.3328   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3814    0.7618   -1.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3761   -1.3563    2.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6458    0.2413    2.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0555   -0.0707    1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0024    4.0378   -0.2359 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
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
  2 31  1  0
 31 32  2  0
 31 33  1  0
 29 10  1  0
 29 13  1  0
 25 14  1  0
 23 17  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  3 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 18 59  1  0
 18 60  1  0
 19 61  1  0
 20 62  1  0
 21 63  1  0
 21 64  1  0
 22 65  1  0
 22 66  1  0
 24 67  1  0
 24 68  1  0
 24 69  1  0
 25 70  1  0
 26 71  1  0
 26 72  1  0
 27 73  1  0
 28 74  1  0
 30 75  1  0
 30 76  1  0
 30 77  1  0
 33 78  1  0
M  END


  Mrv1652308302121382D          

 33 36  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
   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
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 12 31  1  0  0  0  0
 15 31  1  0  0  0  0
 31 32  1  0  0  0  0
  4 33  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0057257

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H45NO5/c1-15(5-10-24(31)28-16(2)25(32)33)20-8-9-21-19-7-6-17-13-18(29)11-12-26(17,3)22(19)14-23(30)27(20,21)4/h15-23,29-30H,5-14H2,1-4H3,(H,28,31)(H,32,33)

> <INCHI_KEY>
UUMHESNLNMWIQK-UHFFFAOYSA-N

> <FORMULA>
C27H45NO5

> <MOLECULAR_WEIGHT>
463.659

> <EXACT_MASS>
463.329773553

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
53.92357205589104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
3.254740256333332

> <ALOGPS_LOGS>
-4.87

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.766549839564828

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.801308675600922

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3082315402158936

> <JCHEM_POLAR_SURFACE_AREA>
106.86000000000001

> <JCHEM_REFRACTIVITY>
126.49419999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.20e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242412
     RDKit          3D
Deoxycholylalanine
 78 81  0  0  0  0  0  0  0  0999 V2000
    6.8902    1.0807   -0.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3601    1.0267   -0.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9229   -0.1020    0.1634 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1409   -1.1080   -0.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8407   -1.0011   -1.6625 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6845   -2.2875    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -3.1467   -0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5047   -2.6406   -0.9907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9610   -3.8975   -1.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4085   -2.2545   -0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0984   -3.3418    0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4696   -2.7500    1.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1262   -1.2972    1.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2580   -0.3767    1.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1590   -0.8082   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3166    0.1310   -0.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0228    1.5704   -0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7987    2.0413   -1.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8535    3.5417   -1.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0620    3.8802   -0.9002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7407    4.0566   -0.7134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5192    3.4142    0.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9796    2.0190    0.7942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7036    2.0007    2.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370    1.0566    0.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6785    1.3198    0.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0135    0.0957   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3301    0.4690   -0.8126 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1804   -1.0102    0.5768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1433   -0.5282    1.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792    2.3171   -0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1740    2.3408    1.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1931    3.5328   -0.5975 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2153    0.0117   -0.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2072    1.6938   -1.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2454    1.4639    0.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9990    0.9596   -1.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1799   -0.1941    1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4279   -2.0267    1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6420   -2.9351    0.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6474   -4.0958    0.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4470   -3.5514   -1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7108   -1.9371   -1.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0900   -4.7735   -1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1252   -3.7648   -1.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4582   -3.9663   -2.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5467   -2.2516   -0.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5062   -3.3846    1.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2489   -4.3028    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0261   -2.9351    0.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9605   -3.2217    1.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9322   -1.2475    2.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9407   -0.4255    1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6223   -1.7881    0.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7078   -0.9088   -1.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9044   -0.1269   -1.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9652   -0.0706    0.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9826    2.0969    0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7192    1.7194   -2.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9600    1.6096   -2.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8341    4.0231   -2.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0735    4.8335   -0.6339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9429    5.1647   -0.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210    4.0752   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799    4.1249    1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000    3.4193    0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4567    2.8137    2.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9829    2.1193    2.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2800    1.0616    2.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4489    1.2595    2.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9558    1.9128   -0.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0984    1.9471    0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4141   -0.3328   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3814    0.7618   -1.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3761   -1.3563    2.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6458    0.2413    2.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0555   -0.0707    1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0024    4.0378   -0.2359 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
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
  2 31  1  0
 31 32  2  0
 31 33  1  0
 29 10  1  0
 29 13  1  0
 25 14  1  0
 23 17  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  3 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 18 59  1  0
 18 60  1  0
 19 61  1  0
 20 62  1  0
 21 63  1  0
 21 64  1  0
 22 65  1  0
 22 66  1  0
 24 67  1  0
 24 68  1  0
 24 69  1  0
 25 70  1  0
 26 71  1  0
 26 72  1  0
 27 73  1  0
 28 74  1  0
 30 75  1  0
 30 76  1  0
 30 77  1  0
 33 78  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  C   UNK     0      32.746  -3.701   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.222  -5.166   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      34.728  -5.486   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      35.204  -6.950   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      36.710  -7.271   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      34.174  -8.095   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      32.667  -7.775   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      32.191  -6.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      31.161  -7.454   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      30.685  -5.990   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      29.654  -7.134   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      28.148  -6.814   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      27.118  -7.958   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      27.672  -5.349   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      26.528  -6.380   0.000  0.00  0.00           C+0
HETATM   33  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   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   31                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   31                                                  
CONECT   16   15   17   27                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   19   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   16   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   12   15   32                                             
CONECT   32   31                                                            
CONECT   33    4                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0242412
HETATM    1  C1  UNL     1       6.890   1.081  -0.693  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.360   1.027  -0.593  1.00  0.00           C  
HETATM    3  N1  UNL     1       4.923  -0.102   0.163  1.00  0.00           N  
HETATM    4  C3  UNL     1       4.141  -1.108  -0.459  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.841  -1.001  -1.662  1.00  0.00           O  
HETATM    6  C4  UNL     1       3.685  -2.287   0.335  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.792  -3.147  -0.454  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.505  -2.641  -0.991  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.961  -3.898  -1.791  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.409  -2.254  -0.142  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.098  -3.342   0.813  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.470  -2.750   1.082  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.126  -1.297   1.309  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.258  -0.377   1.006  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.159  -0.808  -0.102  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.317   0.131  -0.164  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.023   1.570  -0.181  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.799   2.041  -1.588  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.854   3.542  -1.552  1.00  0.00           C  
HETATM   20  O2  UNL     1      -5.062   3.880  -0.900  1.00  0.00           O  
HETATM   21  C18 UNL     1      -2.741   4.057  -0.713  1.00  0.00           C  
HETATM   22  C19 UNL     1      -2.519   3.414   0.594  1.00  0.00           C  
HETATM   23  C20 UNL     1      -2.980   2.019   0.794  1.00  0.00           C  
HETATM   24  C21 UNL     1      -3.704   2.001   2.162  1.00  0.00           C  
HETATM   25  C22 UNL     1      -1.837   1.057   0.965  1.00  0.00           C  
HETATM   26  C23 UNL     1      -0.679   1.320   0.061  1.00  0.00           C  
HETATM   27  C24 UNL     1       0.013   0.096  -0.446  1.00  0.00           C  
HETATM   28  O3  UNL     1       1.330   0.469  -0.813  1.00  0.00           O  
HETATM   29  C25 UNL     1       0.180  -1.010   0.577  1.00  0.00           C  
HETATM   30  C26 UNL     1       1.143  -0.528   1.584  1.00  0.00           C  
HETATM   31  C27 UNL     1       4.879   2.317  -0.012  1.00  0.00           C  
HETATM   32  O4  UNL     1       4.174   2.341   1.028  1.00  0.00           O  
HETATM   33  O5  UNL     1       5.193   3.533  -0.598  1.00  0.00           O  
HETATM   34  H1  UNL     1       7.215   0.012  -0.775  1.00  0.00           H  
HETATM   35  H2  UNL     1       7.207   1.694  -1.554  1.00  0.00           H  
HETATM   36  H3  UNL     1       7.245   1.464   0.286  1.00  0.00           H  
HETATM   37  H4  UNL     1       4.999   0.960  -1.618  1.00  0.00           H  
HETATM   38  H5  UNL     1       5.180  -0.194   1.192  1.00  0.00           H  
HETATM   39  H6  UNL     1       3.428  -2.027   1.349  1.00  0.00           H  
HETATM   40  H7  UNL     1       4.642  -2.935   0.489  1.00  0.00           H  
HETATM   41  H8  UNL     1       2.647  -4.096   0.148  1.00  0.00           H  
HETATM   42  H9  UNL     1       3.447  -3.551  -1.310  1.00  0.00           H  
HETATM   43  H10 UNL     1       1.711  -1.937  -1.857  1.00  0.00           H  
HETATM   44  H11 UNL     1       1.090  -4.773  -1.131  1.00  0.00           H  
HETATM   45  H12 UNL     1      -0.125  -3.765  -1.958  1.00  0.00           H  
HETATM   46  H13 UNL     1       1.458  -3.966  -2.755  1.00  0.00           H  
HETATM   47  H14 UNL     1      -0.547  -2.252  -0.881  1.00  0.00           H  
HETATM   48  H15 UNL     1       0.506  -3.385   1.737  1.00  0.00           H  
HETATM   49  H16 UNL     1      -0.249  -4.303   0.327  1.00  0.00           H  
HETATM   50  H17 UNL     1      -2.026  -2.935   0.133  1.00  0.00           H  
HETATM   51  H18 UNL     1      -1.961  -3.222   1.954  1.00  0.00           H  
HETATM   52  H19 UNL     1      -0.932  -1.247   2.419  1.00  0.00           H  
HETATM   53  H20 UNL     1      -2.941  -0.426   1.922  1.00  0.00           H  
HETATM   54  H21 UNL     1      -3.622  -1.788   0.244  1.00  0.00           H  
HETATM   55  H22 UNL     1      -2.708  -0.909  -1.090  1.00  0.00           H  
HETATM   56  H23 UNL     1      -4.904  -0.127  -1.075  1.00  0.00           H  
HETATM   57  H24 UNL     1      -4.965  -0.071   0.739  1.00  0.00           H  
HETATM   58  H25 UNL     1      -4.983   2.097   0.125  1.00  0.00           H  
HETATM   59  H26 UNL     1      -4.719   1.719  -2.162  1.00  0.00           H  
HETATM   60  H27 UNL     1      -2.960   1.610  -2.111  1.00  0.00           H  
HETATM   61  H28 UNL     1      -3.834   4.023  -2.527  1.00  0.00           H  
HETATM   62  H29 UNL     1      -5.073   4.834  -0.634  1.00  0.00           H  
HETATM   63  H30 UNL     1      -2.943   5.165  -0.580  1.00  0.00           H  
HETATM   64  H31 UNL     1      -1.821   4.075  -1.373  1.00  0.00           H  
HETATM   65  H32 UNL     1      -2.880   4.125   1.400  1.00  0.00           H  
HETATM   66  H33 UNL     1      -1.400   3.419   0.772  1.00  0.00           H  
HETATM   67  H34 UNL     1      -4.457   2.814   2.110  1.00  0.00           H  
HETATM   68  H35 UNL     1      -2.983   2.119   2.970  1.00  0.00           H  
HETATM   69  H36 UNL     1      -4.280   1.062   2.290  1.00  0.00           H  
HETATM   70  H37 UNL     1      -1.449   1.260   2.015  1.00  0.00           H  
HETATM   71  H38 UNL     1      -0.956   1.913  -0.845  1.00  0.00           H  
HETATM   72  H39 UNL     1       0.098   1.947   0.565  1.00  0.00           H  
HETATM   73  H40 UNL     1      -0.414  -0.333  -1.373  1.00  0.00           H  
HETATM   74  H41 UNL     1       1.381   0.762  -1.747  1.00  0.00           H  
HETATM   75  H42 UNL     1       1.376  -1.356   2.321  1.00  0.00           H  
HETATM   76  H43 UNL     1       0.646   0.241   2.234  1.00  0.00           H  
HETATM   77  H44 UNL     1       2.056  -0.071   1.233  1.00  0.00           H  
HETATM   78  H45 UNL     1       6.002   4.038  -0.236  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3   31   37
CONECT    3    4   38
CONECT    4    5    5    6
CONECT    6    7   39   40
CONECT    7    8   41   42
CONECT    8    9   10   43
CONECT    9   44   45   46
CONECT   10   11   29   47
CONECT   11   12   48   49
CONECT   12   13   50   51
CONECT   13   14   29   52
CONECT   14   15   25   53
CONECT   15   16   54   55
CONECT   16   17   56   57
CONECT   17   18   23   58
CONECT   18   19   59   60
CONECT   19   20   21   61
CONECT   20   62
CONECT   21   22   63   64
CONECT   22   23   65   66
CONECT   23   24   25
CONECT   24   67   68   69
CONECT   25   26   70
CONECT   26   27   71   72
CONECT   27   28   29   73
CONECT   28   74
CONECT   29   30
CONECT   30   75   76   77
CONECT   31   32   32   33
CONECT   33   78
END

HMDB0242412
     RDKit          3D
Deoxycholylalanine
 78 81  0  0  0  0  0  0  0  0999 V2000
    6.8902    1.0807   -0.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3601    1.0267   -0.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9229   -0.1020    0.1634 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1409   -1.1080   -0.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8407   -1.0011   -1.6625 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6845   -2.2875    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -3.1467   -0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5047   -2.6406   -0.9907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9610   -3.8975   -1.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4085   -2.2545   -0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0984   -3.3418    0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4696   -2.7500    1.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1262   -1.2972    1.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2580   -0.3767    1.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1590   -0.8082   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3166    0.1310   -0.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0228    1.5704   -0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7987    2.0413   -1.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8535    3.5417   -1.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0620    3.8802   -0.9002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7407    4.0566   -0.7134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5192    3.4142    0.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9796    2.0190    0.7942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7036    2.0007    2.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370    1.0566    0.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6785    1.3198    0.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0135    0.0957   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3301    0.4690   -0.8126 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1804   -1.0102    0.5768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1433   -0.5282    1.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792    2.3171   -0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1740    2.3408    1.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1931    3.5328   -0.5975 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2153    0.0117   -0.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2072    1.6938   -1.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2454    1.4639    0.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9990    0.9596   -1.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1799   -0.1941    1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4279   -2.0267    1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6420   -2.9351    0.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6474   -4.0958    0.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4470   -3.5514   -1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7108   -1.9371   -1.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0900   -4.7735   -1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1252   -3.7648   -1.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4582   -3.9663   -2.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5467   -2.2516   -0.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5062   -3.3846    1.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2489   -4.3028    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0261   -2.9351    0.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9605   -3.2217    1.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9322   -1.2475    2.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9407   -0.4255    1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6223   -1.7881    0.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7078   -0.9088   -1.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9044   -0.1269   -1.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9652   -0.0706    0.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9826    2.0969    0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7192    1.7194   -2.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9600    1.6096   -2.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8341    4.0231   -2.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0735    4.8335   -0.6339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9429    5.1647   -0.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210    4.0752   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799    4.1249    1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000    3.4193    0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4567    2.8137    2.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9829    2.1193    2.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2800    1.0616    2.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4489    1.2595    2.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9558    1.9128   -0.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0984    1.9471    0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4141   -0.3328   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3814    0.7618   -1.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3761   -1.3563    2.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6458    0.2413    2.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0555   -0.0707    1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0024    4.0378   -0.2359 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
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
  2 31  1  0
 31 32  2  0
 31 33  1  0
 29 10  1  0
 29 13  1  0
 25 14  1  0
 23 17  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  3 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 18 59  1  0
 18 60  1  0
 19 61  1  0
 20 62  1  0
 21 63  1  0
 21 64  1  0
 22 65  1  0
 22 66  1  0
 24 67  1  0
 24 68  1  0
 24 69  1  0
 25 70  1  0
 26 71  1  0
 26 72  1  0
 27 73  1  0
 28 74  1  0
 30 75  1  0
 30 76  1  0
 30 77  1  0
 33 78  1  0
M  END

Synonyms

Value	Source
Deoxycholylalanine	HMDB
Ala-Deoxycho	HMDB
Ala-DCA	HMDB
Alanodeoxycholic acid	HMDB
Alanodeoxycholate	HMDB

Molecular Formula

C₂₇H₄₅NO₅

Average Mass

463.659

Monoisotopic Mass

463.329773553

IUPAC Name

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

Traditional Name

2-(4-{5,16-dihydroxy-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)C1CCC2C3CCC4CC(O)CCC4(C)C3CC(O)C12C

InChI Identifier

InChI=1S/C27H45NO5/c1-15(5-10-24(31)28-16(2)25(32)33)20-8-9-21-19-7-6-17-13-18(29)11-12-26(17,3)22(19)14-23(30)27(20,21)4/h15-23,29-30H,5-14H2,1-4H3,(H,28,31)(H,32,33)

InChI Key

UUMHESNLNMWIQK-UHFFFAOYSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0062 g/L	ALOGPS
logP	2.72	ALOGPS
logP	3.25	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	3.8	ChemAxon
pKa (Strongest Basic)	-0.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.86 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	126.49 m³·mol⁻¹	ChemAxon
Polarizability	53.92 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kb-0122900000-e31c71ac516bcd5cd7aa	2021-09-23	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0001900000-f68d10ddd2196779b59f	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0nou-4218900000-41ba95caa0ae96aeadbf	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9611000000-9084588c6ee66937f6ee	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-1b7c870ab275d1ba6a78	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-1002900000-c9421544f4e66637717d	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gvo-5009500000-8772b4901a1cb5b6ed37	2021-10-12	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Intestine

Tissue Locations

Intestine

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria	Bacteroidetes	3	Human feces; Human stool; Human urine; Human
Bacteria	Actinobacteria	2	Human feces; Human
Bacteria	Firmicutes	6	Human ; Human feces; Human stool; Human urine

Exposure Sources

Host Biospecimen and Location

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

External Links

HMDB ID

HMDB0242412

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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

Showing metabocard for Deoxycholylalanine (MMDBc0057257)

MOL for #<Metabolite:0x00007fdb32052318>

3D MOL for #<Metabolite:0x00007fdb32052318>

3D SDF for #<Metabolite:0x00007fdb32052318>

3D-SDF for #<Metabolite:0x00007fdb32052318>

PDB for #<Metabolite:0x00007fdb32052318>

3D PDB for #<Metabolite:0x00007fdb32052318>

SMILES for #<Metabolite:0x00007fdb32052318>

INCHI for #<Metabolite:0x00007fdb32052318>

Structure for #<Metabolite:0x00007fdb32052318>

3D Structure for #<Metabolite:0x00007fdb32052318>