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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-08-30 22:46:40 UTC

Update Date

2022-11-15 17:47:03 UTC

HMDB ID

HMDB0242438

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Deoxycholylproline

Description

Deoxycholylproline 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. Deoxycholylproline consists of the bile acid deoxycholic acid conjugated to the amino acid Proline 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 Deoxycholylproline, 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 ). Deoxycholylproline 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


  Mrv1652308312100562D          

 35 39  0  0  0  0            999 V2000
   -2.1957   -3.5677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3728   -3.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0130   -2.7658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098   -4.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853   -4.2178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211   -3.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1102   -2.8023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1444   -3.9229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1440   -5.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5388   -5.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -4.9669    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
  5 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  4 35  1  0  0  0  0
M  END

HMDB0242438
     RDKit          3D
Deoxycholylproline
 82 86  0  0  0  0  0  0  0  0999 V2000
    2.4532    1.8947    2.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6735    1.0389    1.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5734    1.0346    0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9252    0.4329    0.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7916    0.4358   -0.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3561    0.8950   -1.5642 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1061   -0.0684   -0.4629 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8191   -0.6451    0.6874 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2540   -0.2521    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3610   -0.4270   -1.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9994   -0.1100   -1.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6162   -1.1258   -2.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6161   -1.8637   -2.4298 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3774   -1.2790   -3.7284 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4031    1.7556    1.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3156    1.8506    2.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6868    1.2278    2.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3519    0.2829    1.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4803   -0.4758    1.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7878   -0.1683    1.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8902   -1.0928    1.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7652   -1.6290   -0.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1599   -1.9290   -0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0161   -2.6500   -1.8601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2241   -3.7801   -1.6352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3250   -1.7441   -2.8283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0240   -1.1953   -2.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0710   -0.6106   -0.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8652    0.6239   -0.9307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6480   -0.5377   -0.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9043    0.4960   -1.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4877    0.7190   -0.6710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0706    1.6470   -1.5437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6756    1.2925    0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5935    2.5235    0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0471    2.6649    2.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701    1.2518    3.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7521    2.4381    3.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6624    0.0283    2.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1378    0.3425   -0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6521    2.0209   -0.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4308    0.9157    1.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8304   -0.6350    1.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5244   -0.1714    1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7743   -1.7462    0.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4932    0.7661    0.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9161   -0.9849    0.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1459    0.2141   -1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5765   -1.5110   -1.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8592   -2.1424   -3.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6493    2.8284    1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1870    1.1614    3.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3482    2.8636    3.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0152    0.6843    3.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4586    1.9620    2.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5073   -0.3587    1.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3106   -1.5527    1.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5496   -0.4188    2.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0496    0.8808    1.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8736   -0.5782    1.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9352   -1.9911    2.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1761   -2.5554   -0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6092   -2.6354    0.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7385   -0.9932   -0.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0110   -2.8974   -2.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2405   -4.3037   -2.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0979   -2.3675   -3.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9923   -0.9152   -3.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1689   -1.8954   -2.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7760   -0.3171   -3.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5871    0.5738   -1.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3621    1.5756   -1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5699    0.6922   -0.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1943   -1.5155   -0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3572    1.4662   -1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6990    0.1207   -2.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0360   -0.2899   -0.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1745    1.2868   -2.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6464    2.2738    0.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3886    3.3033    1.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3417    3.0021   -0.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  2 15  1  0
 15 16  1  0
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 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 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
 31 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 11  7  1  0
 34 15  1  0
 34 18  1  0
 30 19  1  0
 28 22  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
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 11 50  1  0
 14 51  1  0
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 16 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 18 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
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 25 67  1  0
 26 68  1  0
 26 69  1  0
 27 70  1  0
 27 71  1  0
 29 72  1  0
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 30 75  1  0
 31 76  1  0
 31 77  1  0
 32 78  1  0
 33 79  1  0
 35 80  1  0
 35 81  1  0
 35 82  1  0
M  END


  Mrv1652308312100562D          

 35 39  0  0  0  0            999 V2000
   -2.1957   -3.5677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3728   -3.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0130   -2.7658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098   -4.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853   -4.2178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211   -3.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1102   -2.8023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1444   -3.9229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1440   -5.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5388   -5.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -4.9669    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
  5 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  4 35  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242438

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CCC(=O)N1CCCC1C(O)=O)C1CCC2C3CCC4CC(O)CCC4(C)C3CC(O)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H47NO5/c1-17(6-11-26(33)30-14-4-5-24(30)27(34)35)21-9-10-22-20-8-7-18-15-19(31)12-13-28(18,2)23(20)16-25(32)29(21,22)3/h17-25,31-32H,4-16H2,1-3H3,(H,34,35)

> <INCHI_KEY>
BHWXBRBFQBOUAF-UHFFFAOYSA-N

> <FORMULA>
C29H47NO5

> <MOLECULAR_WEIGHT>
489.697

> <EXACT_MASS>
489.345423617

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
57.337926609846335

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanoyl)pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
3.5274058339999983

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.296396318179

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8093974333567604

> <JCHEM_PKA_STRONGEST_BASIC>
-0.22608716724785427

> <JCHEM_POLAR_SURFACE_AREA>
98.07000000000001

> <JCHEM_REFRACTIVITY>
134.18329999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanoyl)pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242438
     RDKit          3D
Deoxycholylproline
 82 86  0  0  0  0  0  0  0  0999 V2000
    2.4532    1.8947    2.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6735    1.0389    1.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5734    1.0346    0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9252    0.4329    0.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7916    0.4358   -0.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3561    0.8950   -1.5642 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1061   -0.0684   -0.4629 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8191   -0.6451    0.6874 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2540   -0.2521    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3610   -0.4270   -1.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9994   -0.1100   -1.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6162   -1.1258   -2.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6161   -1.8637   -2.4298 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3774   -1.2790   -3.7284 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4031    1.7556    1.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3156    1.8506    2.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6868    1.2278    2.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3519    0.2829    1.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4803   -0.4758    1.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7878   -0.1683    1.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8902   -1.0928    1.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7652   -1.6290   -0.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1599   -1.9290   -0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0161   -2.6500   -1.8601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2241   -3.7801   -1.6352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3250   -1.7441   -2.8283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0240   -1.1953   -2.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0710   -0.6106   -0.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8652    0.6239   -0.9307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6480   -0.5377   -0.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9043    0.4960   -1.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4877    0.7190   -0.6710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0706    1.6470   -1.5437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6756    1.2925    0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5935    2.5235    0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0471    2.6649    2.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701    1.2518    3.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7521    2.4381    3.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6624    0.0283    2.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1378    0.3425   -0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6521    2.0209   -0.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4308    0.9157    1.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8304   -0.6350    1.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5244   -0.1714    1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7743   -1.7462    0.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4932    0.7661    0.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9161   -0.9849    0.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1459    0.2141   -1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5765   -1.5110   -1.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9334    0.8920   -2.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.1424   -3.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6493    2.8284    1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1870    1.1614    3.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3482    2.8636    3.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0152    0.6843    3.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4586    1.9620    2.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5073   -0.3587    1.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3106   -1.5527    1.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5496   -0.4188    2.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0496    0.8808    1.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8736   -0.5782    1.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9352   -1.9911    2.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1761   -2.5554   -0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6092   -2.6354    0.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7385   -0.9932   -0.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0110   -2.8974   -2.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2405   -4.3037   -2.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0979   -2.3675   -3.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9923   -0.9152   -3.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1689   -1.8954   -2.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7760   -0.3171   -3.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5871    0.5738   -1.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3621    1.5756   -1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5699    0.6922   -0.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1943   -1.5155   -0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3572    1.4662   -1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6990    0.1207   -2.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0360   -0.2899   -0.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1745    1.2868   -2.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6464    2.2738    0.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3886    3.3033    1.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3417    3.0021   -0.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 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
 31 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 11  7  1  0
 34 15  1  0
 34 18  1  0
 30 19  1  0
 28 22  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 14 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 18 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  0
 23 64  1  0
 23 65  1  0
 24 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 27 70  1  0
 27 71  1  0
 29 72  1  0
 29 73  1  0
 29 74  1  0
 30 75  1  0
 31 76  1  0
 31 77  1  0
 32 78  1  0
 33 79  1  0
 35 80  1  0
 35 81  1  0
 35 82  1  0
M  END

HEADER    PROTEIN                                 31-AUG-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-AUG-21         0                                  
HETATM    1  O   UNK     0      -4.099  -6.660   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.563  -6.549   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.891  -5.163   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.698  -7.823   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.159  -7.873   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.206  -5.231   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.736  -7.323   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.269  -9.353   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.006 -10.217   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.222  -9.272   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   35                                                  
CONECT    5    4    6   33                                                  
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    5   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    4                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

COMPND    HMDB0242438
HETATM    1  C1  UNL     1       2.453   1.895   2.718  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.674   1.039   1.677  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.573   1.035   0.438  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.925   0.433   0.762  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.792   0.436  -0.475  1.00  0.00           C  
HETATM    6  O1  UNL     1       4.356   0.895  -1.564  1.00  0.00           O  
HETATM    7  N1  UNL     1       6.106  -0.068  -0.463  1.00  0.00           N  
HETATM    8  C6  UNL     1       6.819  -0.645   0.687  1.00  0.00           C  
HETATM    9  C7  UNL     1       8.254  -0.252   0.399  1.00  0.00           C  
HETATM   10  C8  UNL     1       8.361  -0.427  -1.081  1.00  0.00           C  
HETATM   11  C9  UNL     1       6.999  -0.110  -1.596  1.00  0.00           C  
HETATM   12  C10 UNL     1       6.616  -1.126  -2.586  1.00  0.00           C  
HETATM   13  O2  UNL     1       5.616  -1.864  -2.430  1.00  0.00           O  
HETATM   14  O3  UNL     1       7.377  -1.279  -3.728  1.00  0.00           O  
HETATM   15  C11 UNL     1       0.403   1.756   1.509  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.316   1.851   2.875  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.687   1.228   2.687  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.352   0.283   1.553  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.480  -0.476   1.008  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.788  -0.168   1.758  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.890  -1.093   1.349  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.765  -1.629  -0.045  1.00  0.00           C  
HETATM   23  C19 UNL     1      -6.160  -1.929  -0.544  1.00  0.00           C  
HETATM   24  C20 UNL     1      -6.016  -2.650  -1.860  1.00  0.00           C  
HETATM   25  O4  UNL     1      -5.224  -3.780  -1.635  1.00  0.00           O  
HETATM   26  C21 UNL     1      -5.325  -1.744  -2.828  1.00  0.00           C  
HETATM   27  C22 UNL     1      -4.024  -1.195  -2.362  1.00  0.00           C  
HETATM   28  C23 UNL     1      -4.071  -0.611  -0.951  1.00  0.00           C  
HETATM   29  C24 UNL     1      -4.865   0.624  -0.931  1.00  0.00           C  
HETATM   30  C25 UNL     1      -2.648  -0.538  -0.467  1.00  0.00           C  
HETATM   31  C26 UNL     1      -1.904   0.496  -1.248  1.00  0.00           C  
HETATM   32  C27 UNL     1      -0.488   0.719  -0.671  1.00  0.00           C  
HETATM   33  O5  UNL     1       0.071   1.647  -1.544  1.00  0.00           O  
HETATM   34  C28 UNL     1      -0.676   1.292   0.655  1.00  0.00           C  
HETATM   35  C29 UNL     1      -1.593   2.524   0.461  1.00  0.00           C  
HETATM   36  H1  UNL     1       3.047   2.665   2.211  1.00  0.00           H  
HETATM   37  H2  UNL     1       3.170   1.252   3.268  1.00  0.00           H  
HETATM   38  H3  UNL     1       1.752   2.438   3.383  1.00  0.00           H  
HETATM   39  H4  UNL     1       1.662   0.028   2.066  1.00  0.00           H  
HETATM   40  H5  UNL     1       2.138   0.343  -0.302  1.00  0.00           H  
HETATM   41  H6  UNL     1       2.652   2.021  -0.036  1.00  0.00           H  
HETATM   42  H7  UNL     1       4.431   0.916   1.621  1.00  0.00           H  
HETATM   43  H8  UNL     1       3.830  -0.635   1.049  1.00  0.00           H  
HETATM   44  H9  UNL     1       6.524  -0.171   1.623  1.00  0.00           H  
HETATM   45  H10 UNL     1       6.774  -1.746   0.679  1.00  0.00           H  
HETATM   46  H11 UNL     1       8.493   0.766   0.726  1.00  0.00           H  
HETATM   47  H12 UNL     1       8.916  -0.985   0.940  1.00  0.00           H  
HETATM   48  H13 UNL     1       9.146   0.214  -1.535  1.00  0.00           H  
HETATM   49  H14 UNL     1       8.577  -1.511  -1.278  1.00  0.00           H  
HETATM   50  H15 UNL     1       6.933   0.892  -2.076  1.00  0.00           H  
HETATM   51  H16 UNL     1       7.859  -2.142  -3.983  1.00  0.00           H  
HETATM   52  H17 UNL     1       0.649   2.828   1.252  1.00  0.00           H  
HETATM   53  H18 UNL     1       0.187   1.161   3.610  1.00  0.00           H  
HETATM   54  H19 UNL     1      -0.348   2.864   3.264  1.00  0.00           H  
HETATM   55  H20 UNL     1      -2.015   0.684   3.596  1.00  0.00           H  
HETATM   56  H21 UNL     1      -2.459   1.962   2.454  1.00  0.00           H  
HETATM   57  H22 UNL     1      -0.507  -0.359   1.948  1.00  0.00           H  
HETATM   58  H23 UNL     1      -2.311  -1.553   1.355  1.00  0.00           H  
HETATM   59  H24 UNL     1      -3.550  -0.419   2.838  1.00  0.00           H  
HETATM   60  H25 UNL     1      -4.050   0.881   1.780  1.00  0.00           H  
HETATM   61  H26 UNL     1      -5.874  -0.578   1.517  1.00  0.00           H  
HETATM   62  H27 UNL     1      -4.935  -1.991   2.027  1.00  0.00           H  
HETATM   63  H28 UNL     1      -4.176  -2.555  -0.111  1.00  0.00           H  
HETATM   64  H29 UNL     1      -6.609  -2.635   0.187  1.00  0.00           H  
HETATM   65  H30 UNL     1      -6.738  -0.993  -0.629  1.00  0.00           H  
HETATM   66  H31 UNL     1      -7.011  -2.897  -2.266  1.00  0.00           H  
HETATM   67  H32 UNL     1      -5.240  -4.304  -2.482  1.00  0.00           H  
HETATM   68  H33 UNL     1      -5.098  -2.367  -3.738  1.00  0.00           H  
HETATM   69  H34 UNL     1      -5.992  -0.915  -3.133  1.00  0.00           H  
HETATM   70  H35 UNL     1      -3.169  -1.895  -2.484  1.00  0.00           H  
HETATM   71  H36 UNL     1      -3.776  -0.317  -3.027  1.00  0.00           H  
HETATM   72  H37 UNL     1      -5.587   0.574  -1.804  1.00  0.00           H  
HETATM   73  H38 UNL     1      -4.362   1.576  -1.047  1.00  0.00           H  
HETATM   74  H39 UNL     1      -5.570   0.692  -0.049  1.00  0.00           H  
HETATM   75  H40 UNL     1      -2.194  -1.515  -0.844  1.00  0.00           H  
HETATM   76  H41 UNL     1      -2.357   1.466  -1.361  1.00  0.00           H  
HETATM   77  H42 UNL     1      -1.699   0.121  -2.293  1.00  0.00           H  
HETATM   78  H43 UNL     1      -0.036  -0.290  -0.721  1.00  0.00           H  
HETATM   79  H44 UNL     1       0.174   1.287  -2.471  1.00  0.00           H  
HETATM   80  H45 UNL     1      -2.646   2.274   0.458  1.00  0.00           H  
HETATM   81  H46 UNL     1      -1.389   3.303   1.227  1.00  0.00           H  
HETATM   82  H47 UNL     1      -1.342   3.002  -0.508  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3   15   39
CONECT    3    4   40   41
CONECT    4    5   42   43
CONECT    5    6    6    7
CONECT    7    8   11
CONECT    8    9   44   45
CONECT    9   10   46   47
CONECT   10   11   48   49
CONECT   11   12   50
CONECT   12   13   13   14
CONECT   14   51
CONECT   15   16   34   52
CONECT   16   17   53   54
CONECT   17   18   55   56
CONECT   18   19   34   57
CONECT   19   20   30   58
CONECT   20   21   59   60
CONECT   21   22   61   62
CONECT   22   23   28   63
CONECT   23   24   64   65
CONECT   24   25   26   66
CONECT   25   67
CONECT   26   27   68   69
CONECT   27   28   70   71
CONECT   28   29   30
CONECT   29   72   73   74
CONECT   30   31   75
CONECT   31   32   76   77
CONECT   32   33   34   78
CONECT   33   79
CONECT   34   35
CONECT   35   80   81   82
END

HMDB0242438
     RDKit          3D
Deoxycholylproline
 82 86  0  0  0  0  0  0  0  0999 V2000
    2.4532    1.8947    2.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6735    1.0389    1.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5734    1.0346    0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9252    0.4329    0.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7916    0.4358   -0.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3561    0.8950   -1.5642 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1061   -0.0684   -0.4629 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8191   -0.6451    0.6874 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2540   -0.2521    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3610   -0.4270   -1.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9994   -0.1100   -1.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6162   -1.1258   -2.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6161   -1.8637   -2.4298 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3774   -1.2790   -3.7284 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4031    1.7556    1.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3156    1.8506    2.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6868    1.2278    2.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3519    0.2829    1.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4803   -0.4758    1.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7878   -0.1683    1.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8902   -1.0928    1.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7652   -1.6290   -0.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1599   -1.9290   -0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0161   -2.6500   -1.8601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2241   -3.7801   -1.6352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3250   -1.7441   -2.8283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0240   -1.1953   -2.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0710   -0.6106   -0.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8652    0.6239   -0.9307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6480   -0.5377   -0.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9043    0.4960   -1.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4877    0.7190   -0.6710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0706    1.6470   -1.5437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6756    1.2925    0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5935    2.5235    0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0471    2.6649    2.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701    1.2518    3.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7521    2.4381    3.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6624    0.0283    2.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1378    0.3425   -0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6521    2.0209   -0.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4308    0.9157    1.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8304   -0.6350    1.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5244   -0.1714    1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7743   -1.7462    0.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4932    0.7661    0.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9161   -0.9849    0.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1459    0.2141   -1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5765   -1.5110   -1.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9334    0.8920   -2.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.1424   -3.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6493    2.8284    1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1870    1.1614    3.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3482    2.8636    3.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0152    0.6843    3.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4586    1.9620    2.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5073   -0.3587    1.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3106   -1.5527    1.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5496   -0.4188    2.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0496    0.8808    1.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8736   -0.5782    1.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9352   -1.9911    2.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1761   -2.5554   -0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6092   -2.6354    0.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7385   -0.9932   -0.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0110   -2.8974   -2.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2405   -4.3037   -2.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0979   -2.3675   -3.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9923   -0.9152   -3.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1689   -1.8954   -2.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7760   -0.3171   -3.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5871    0.5738   -1.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3621    1.5756   -1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5699    0.6922   -0.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1943   -1.5155   -0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3572    1.4662   -1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6990    0.1207   -2.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0360   -0.2899   -0.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1745    1.2868   -2.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6464    2.2738    0.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3886    3.3033    1.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3417    3.0021   -0.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 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
 31 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 11  7  1  0
 34 15  1  0
 34 18  1  0
 30 19  1  0
 28 22  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 14 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 18 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  0
 23 64  1  0
 23 65  1  0
 24 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 27 70  1  0
 27 71  1  0
 29 72  1  0
 29 73  1  0
 29 74  1  0
 30 75  1  0
 31 76  1  0
 31 77  1  0
 32 78  1  0
 33 79  1  0
 35 80  1  0
 35 81  1  0
 35 82  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₉H₄₇NO₅

Average Molecular Weight

489.697

Monoisotopic Molecular Weight

489.345423617

IUPAC Name

1-(4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanoyl)pyrrolidine-2-carboxylic acid

Traditional Name

1-(4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanoyl)pyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(CCC(=O)N1CCCC1C(O)=O)C1CCC2C3CCC4CC(O)CCC4(C)C3CC(O)C12C

InChI Identifier

InChI=1S/C29H47NO5/c1-17(6-11-26(33)30-14-4-5-24(30)27(34)35)21-9-10-22-20-8-7-18-15-19(31)12-13-28(18,2)23(20)16-25(32)29(21,22)3/h17-25,31-32H,4-16H2,1-3H3,(H,34,35)

InChI Key

BHWXBRBFQBOUAF-UHFFFAOYSA-N

Chemical Taxonomy

Classification

Not classified

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	3.1	ALOGPS
logP	3.53	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	3.81	ChemAxon
pKa (Strongest Basic)	-0.23	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	98.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	134.18 m³·mol⁻¹	ChemAxon
Polarizability	57.34 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	246.119	30932474
DeepCCS	[M+Na]+	221.347	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Deoxycholylproline	CC(CCC(=O)N1CCCC1C(O)=O)C1CCC2C3CCC4CC(O)CCC4(C)C3CC(O)C12C	3403.0	Standard polar	33892256
Deoxycholylproline	CC(CCC(=O)N1CCCC1C(O)=O)C1CCC2C3CCC4CC(O)CCC4(C)C3CC(O)C12C	3522.8	Standard non polar	33892256
Deoxycholylproline	CC(CCC(=O)N1CCCC1C(O)=O)C1CCC2C3CCC4CC(O)CCC4(C)C3CC(O)C12C	4293.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxycholylproline GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-1112900000-a96fc0f2d97d302a78bf	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxycholylproline 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 - Deoxycholylproline 10V, Positive-QTOF	splash10-0006-0000900000-76385ebbf0e75df0360b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxycholylproline 20V, Positive-QTOF	splash10-0ffx-2411900000-689d94109dcde6b2cc9c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxycholylproline 40V, Positive-QTOF	splash10-0f6t-9802000000-5653f9f5e7fe70b1d3a3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxycholylproline 10V, Negative-QTOF	splash10-000i-0000900000-1e4e1a7fd21b6ea4b576	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxycholylproline 20V, Negative-QTOF	splash10-000i-1102900000-24ff65c352ccfaba6734	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxycholylproline 40V, Negative-QTOF	splash10-01pd-9207800000-aaf51247faddd36c60ee	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Intestine

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Deoxycholylproline (HMDB0242438)

MOL for HMDB0242438 (Deoxycholylproline)

3D MOL for HMDB0242438 (Deoxycholylproline)

3D SDF for HMDB0242438 (Deoxycholylproline)

3D-SDF for HMDB0242438 (Deoxycholylproline)

PDB for HMDB0242438 (Deoxycholylproline)

3D PDB for HMDB0242438 (Deoxycholylproline)

SMILES for HMDB0242438 (Deoxycholylproline)

INCHI for HMDB0242438 (Deoxycholylproline)

Structure for HMDB0242438 (Deoxycholylproline)

3D Structure for HMDB0242438 (Deoxycholylproline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra