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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-16 03:44:52 UTC

Update Date

2022-03-07 03:17:53 UTC

HMDB ID

HMDB0062342

Secondary Accession Numbers

HMDB62342

Metabolite Identification

Common Name

N-Stearoyl phenylalanine

Description

N-stearoyl phenylalanine belongs to the class of compounds known as N-acylamides. These are molecules characterized by a fatty acyl group linked to a primary amine by an amide bond. More specifically, it is a Stearic acid amide of Phenylalanine. It is believed that there are more than 800 types of N-acylamides in the human body. N-acylamides fall into several categories: amino acid conjugates (e.g., those acyl amides conjugated with amino acids), neurotransmitter conjugates (e.g., those acylamides conjugated with neurotransmitters), ethanolamine conjugates (e.g., those acylamides conjugated to ethanolamine), and taurine conjugates (e.g., those acyamides conjugated to taurine). N-Stearoyl phenylalanine is an amino acid conjugate. N-acylamides can be classified into 9 different categories depending on the size of their acyl-group: 1) short-chain N-acylamides; 2) medium-chain N-acylamides; 3) long-chain N-acylamides; and 4) very long-chain N-acylamides; 5) hydroxy N-acylamides; 6) branched chain N-acylamides; 7) unsaturated N-acylamides; 8) dicarboxylic N-acylamides and 9) miscellaneous N-acylamides. N-Stearoyl phenylalanine is therefore classified as a long chain N-acylamide. N-acyl amides have a variety of signaling functions in physiology, including in cardiovascular activity, metabolic homeostasis, memory, cognition, pain, motor control and others (PMID: 15655504 ). N-acyl amides have also been shown to play a role in cell migration, inflammation and certain pathological conditions such as diabetes, cancer, neurodegenerative disease, and obesity (PMID: 23144998 ; PMID: 25136293 ; PMID: 28854168 ).N-acyl amides can be synthesized both endogenously and by gut microbiota (PMID: 28854168 ). N-acylamides can be biosynthesized via different routes, depending on the parent amine group. N-acyl ethanolamines (NAEs) are formed via the hydrolysis of an unusual phospholipid precursor, N-acyl-phosphatidylethanolamine (NAPE), by a specific phospholipase D. N-acyl amino acids are synthesized via a circulating peptidase M20 domain containing 1 (PM20D1), which can catalyze the bidirectional the condensation and hydrolysis of a variety of N-acyl amino acids. The degradation of N-acylamides is largely mediated by an enzyme called fatty acid amide hydrolase (FAAH), which catalyzes the hydrolysis of N-acylamides into fatty acids and the biogenic amines. Many N-acylamides are involved in lipid signaling system through interactions with transient receptor potential channels (TRP). TRP channel proteins interact with N-acyl amides such as N-arachidonoyl ethanolamide (Anandamide), N-arachidonoyl dopamine and others in an opportunistic fashion (PMID: 23178153 ). This signaling system has been shown to play a role in the physiological processes involved in inflammation (PMID: 25136293 ). Other N-acyl amides, including N-oleoyl-glutamine, have also been characterized as TRP channel antagonists (PMID: 29967167 ). N-acylamides have also been shown to have G-protein-coupled receptors (GPCRs) binding activity (PMID: 28854168 ). The study of N-acylamides is an active area of research and it is likely that many novel N-acylamides will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered for these molecules.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652303161704442D          

 32 32  0  0  1  0            999 V2000
   -4.2868   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  2 10  1  6  0  0  0
 10 11  2  0  0  0  0
 11 12  1  4  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
M  END

HMDB0062342
     RDKit          3D
N-Stearoyl phenylalanine
 76 76  0  0  0  0  0  0  0  0999 V2000
   10.4671    0.5883    2.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3263    1.0849    0.6884 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9152    1.5022    0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9370    0.3834    0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2367   -0.7607   -0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2785   -1.9182   -0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8729   -1.5012   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9658   -2.7098   -0.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5244   -2.3334   -0.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721   -1.2897    0.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5538   -0.9324   -0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6380   -2.1151   -0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7526   -1.7268   -0.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3500   -0.6958    0.4207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371   -0.3051   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6619   -1.4887   -0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0240   -1.0746   -0.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6726   -0.0436    0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2035   -0.5267    1.5068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6859    1.1117   -0.0230 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0478    2.4133    0.2265 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9713    2.8658   -0.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1649    1.9663   -0.9637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0953    0.8138   -1.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1829   -0.0356   -1.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3197    0.2768   -1.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4068    1.4330   -0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3162    2.2807   -0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7750    2.6089    1.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0781    1.7164    2.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1480    3.9232    1.8296 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8601   -0.3339    2.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0985    1.3806    2.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5142    0.3209    2.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6573    0.3376   -0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0025    1.9744    0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6365    2.3864    1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8771    1.8933   -0.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9136    0.7920    0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8827    0.0686    1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1641   -0.3943   -1.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2845   -1.1062   -0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2963   -2.2195    0.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6053   -2.7616   -0.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8401   -1.1927   -1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5597   -0.6849    0.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2771   -3.4490   -1.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0149   -3.1619    0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3908   -2.0520   -1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9526   -3.2895   -0.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5585   -0.3481    0.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9932   -1.5843    1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1884   -0.0703    0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -0.5466   -1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6141   -2.4555    0.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9932   -2.9251   -0.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3548   -2.6740   -0.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676   -1.3276   -1.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4303   -1.1044    1.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7709    0.2243    0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1378    0.5268    0.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6314    0.0654   -1.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3071   -2.2697   -0.7552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8009   -1.8779    0.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9075   -0.6810   -1.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6570   -1.9817   -0.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1067   -0.9828    1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1946    3.1616    0.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2971    3.9030   -0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3652    2.7358   -1.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1940    0.5691   -2.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1075   -0.9449   -2.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1572   -0.3975   -1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2965    1.6747    0.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3427    3.2007    0.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0549    4.6954    1.1858 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  1  0
  6  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  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
 18 20  2  3
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 21 29  1  0
 29 30  2  0
 29 31  1  0
 28 23  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
  9 50  1  0
 10 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 12 56  1  0
 13 57  1  0
 13 58  1  0
 14 59  1  0
 14 60  1  0
 15 61  1  0
 15 62  1  0
 16 63  1  0
 16 64  1  0
 17 65  1  0
 17 66  1  0
 19 67  1  0
 21 68  1  1
 22 69  1  0
 22 70  1  0
 24 71  1  0
 25 72  1  0
 26 73  1  0
 27 74  1  0
 28 75  1  0
 31 76  1  0
M  END


  Mrv1652303161704442D          

 32 32  0  0  1  0            999 V2000
   -4.2868   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  2 10  1  6  0  0  0
 10 11  2  0  0  0  0
 11 12  1  4  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062342

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@](CC1=CC=CC=C1)(N=C(O)CCCCCCCCCCCCCCCCC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H45NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-22-26(29)28-25(27(30)31)23-24-20-17-16-18-21-24/h16-18,20-21,25H,2-15,19,22-23H2,1H3,(H,28,29)(H,30,31)/t25-/m0/s1

> <INCHI_KEY>
PHZQULSGYVCYNC-VWLOTQADSA-N

> <FORMULA>
C27H45NO3

> <MOLECULAR_WEIGHT>
431.661

> <EXACT_MASS>
431.339944313

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
54.717996300079655

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(1-hydroxyoctadecylidene)amino]-3-phenylpropanoic acid

> <ALOGPS_LOGP>
7.87

> <JCHEM_LOGP>
9.085131605

> <ALOGPS_LOGS>
-6.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.148552180015475

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.176851950471343

> <JCHEM_PKA_STRONGEST_BASIC>
1.5752196646177081

> <JCHEM_POLAR_SURFACE_AREA>
69.89000000000001

> <JCHEM_REFRACTIVITY>
128.72369999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.03e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(1-hydroxyoctadecylidene)amino]-3-phenylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062342
     RDKit          3D
N-Stearoyl phenylalanine
 76 76  0  0  0  0  0  0  0  0999 V2000
   10.4671    0.5883    2.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3263    1.0849    0.6884 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9152    1.5022    0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9370    0.3834    0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2367   -0.7607   -0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2785   -1.9182   -0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8729   -1.5012   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9658   -2.7098   -0.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5244   -2.3334   -0.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721   -1.2897    0.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5538   -0.9324   -0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6380   -2.1151   -0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7526   -1.7268   -0.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3500   -0.6958    0.4207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371   -0.3051   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6619   -1.4887   -0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0240   -1.0746   -0.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6726   -0.0436    0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2035   -0.5267    1.5068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6859    1.1117   -0.0230 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0478    2.4133    0.2265 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9713    2.8658   -0.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1649    1.9663   -0.9637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0953    0.8138   -1.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1829   -0.0356   -1.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3197    0.2768   -1.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4068    1.4330   -0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3162    2.2807   -0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7750    2.6089    1.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0781    1.7164    2.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1480    3.9232    1.8296 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8601   -0.3339    2.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0985    1.3806    2.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5142    0.3209    2.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6573    0.3376   -0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0025    1.9744    0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6365    2.3864    1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8771    1.8933   -0.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9136    0.7920    0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8827    0.0686    1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1641   -0.3943   -1.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2845   -1.1062   -0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2963   -2.2195    0.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6053   -2.7616   -0.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8401   -1.1927   -1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5597   -0.6849    0.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2771   -3.4490   -1.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0149   -3.1619    0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3908   -2.0520   -1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9526   -3.2895   -0.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5585   -0.3481    0.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9932   -1.5843    1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1884   -0.0703    0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -0.5466   -1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6141   -2.4555    0.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9932   -2.9251   -0.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3548   -2.6740   -0.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676   -1.3276   -1.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4303   -1.1044    1.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7709    0.2243    0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1378    0.5268    0.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6314    0.0654   -1.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3071   -2.2697   -0.7552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8009   -1.8779    0.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9075   -0.6810   -1.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6570   -1.9817   -0.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1067   -0.9828    1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1946    3.1616    0.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2971    3.9030   -0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3652    2.7358   -1.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1940    0.5691   -2.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1075   -0.9449   -2.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1572   -0.3975   -1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2965    1.6747    0.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3427    3.2007    0.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0549    4.6954    1.1858 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  1  0
  6  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  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
 18 20  2  3
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 21 29  1  0
 29 30  2  0
 29 31  1  0
 28 23  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
  9 50  1  0
 10 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 12 56  1  0
 13 57  1  0
 13 58  1  0
 14 59  1  0
 14 60  1  0
 15 61  1  0
 15 62  1  0
 16 63  1  0
 16 64  1  0
 17 65  1  0
 17 66  1  0
 19 67  1  0
 21 68  1  1
 22 69  1  0
 22 70  1  0
 24 71  1  0
 25 72  1  0
 26 73  1  0
 27 74  1  0
 28 75  1  0
 31 76  1  0
M  END

HEADER    PROTEIN                                 16-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAR-17         0                                  
HETATM    1  H   UNK     0      -8.002  -6.160   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.669  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -12.003 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -13.337  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -13.337  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -6.668  -6.930   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.338  -6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -9.336 -10.010   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10   30                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    2   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30    2   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   64    0
END

COMPND    HMDB0062342
HETATM    1  C1  UNL     1      10.467   0.588   2.115  1.00  0.00           C  
HETATM    2  C2  UNL     1      10.326   1.085   0.688  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.915   1.502   0.409  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.937   0.383   0.596  1.00  0.00           C  
HETATM    5  C5  UNL     1       8.237  -0.761  -0.315  1.00  0.00           C  
HETATM    6  C6  UNL     1       7.279  -1.918  -0.183  1.00  0.00           C  
HETATM    7  C7  UNL     1       5.873  -1.501  -0.496  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.966  -2.710  -0.361  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.524  -2.333  -0.678  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.972  -1.290   0.235  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.554  -0.932  -0.142  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.638  -2.115  -0.083  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.753  -1.727  -0.485  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.350  -0.696   0.421  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.737  -0.305  -0.039  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.662  -1.489  -0.068  1.00  0.00           C  
HETATM   17  C17 UNL     1      -5.024  -1.075  -0.557  1.00  0.00           C  
HETATM   18  C18 UNL     1      -5.673  -0.044   0.332  1.00  0.00           C  
HETATM   19  O1  UNL     1      -6.203  -0.527   1.507  1.00  0.00           O  
HETATM   20  N1  UNL     1      -5.686   1.112  -0.023  1.00  0.00           N  
HETATM   21  C19 UNL     1      -6.048   2.413   0.226  1.00  0.00           C  
HETATM   22  C20 UNL     1      -6.971   2.866  -0.943  1.00  0.00           C  
HETATM   23  C21 UNL     1      -8.165   1.966  -0.964  1.00  0.00           C  
HETATM   24  C22 UNL     1      -8.095   0.814  -1.724  1.00  0.00           C  
HETATM   25  C23 UNL     1      -9.183  -0.036  -1.763  1.00  0.00           C  
HETATM   26  C24 UNL     1     -10.320   0.277  -1.046  1.00  0.00           C  
HETATM   27  C25 UNL     1     -10.407   1.433  -0.275  1.00  0.00           C  
HETATM   28  C26 UNL     1      -9.316   2.281  -0.238  1.00  0.00           C  
HETATM   29  C27 UNL     1      -6.775   2.609   1.489  1.00  0.00           C  
HETATM   30  O2  UNL     1      -7.078   1.716   2.262  1.00  0.00           O  
HETATM   31  O3  UNL     1      -7.148   3.923   1.830  1.00  0.00           O  
HETATM   32  H1  UNL     1       9.860  -0.334   2.255  1.00  0.00           H  
HETATM   33  H2  UNL     1      10.098   1.381   2.785  1.00  0.00           H  
HETATM   34  H3  UNL     1      11.514   0.321   2.321  1.00  0.00           H  
HETATM   35  H4  UNL     1      10.657   0.338  -0.039  1.00  0.00           H  
HETATM   36  H5  UNL     1      11.003   1.974   0.608  1.00  0.00           H  
HETATM   37  H6  UNL     1       8.637   2.386   1.042  1.00  0.00           H  
HETATM   38  H7  UNL     1       8.877   1.893  -0.638  1.00  0.00           H  
HETATM   39  H8  UNL     1       6.914   0.792   0.368  1.00  0.00           H  
HETATM   40  H9  UNL     1       7.883   0.069   1.659  1.00  0.00           H  
HETATM   41  H10 UNL     1       8.164  -0.394  -1.368  1.00  0.00           H  
HETATM   42  H11 UNL     1       9.284  -1.106  -0.196  1.00  0.00           H  
HETATM   43  H12 UNL     1       7.296  -2.219   0.895  1.00  0.00           H  
HETATM   44  H13 UNL     1       7.605  -2.762  -0.801  1.00  0.00           H  
HETATM   45  H14 UNL     1       5.840  -1.193  -1.559  1.00  0.00           H  
HETATM   46  H15 UNL     1       5.560  -0.685   0.179  1.00  0.00           H  
HETATM   47  H16 UNL     1       5.277  -3.449  -1.117  1.00  0.00           H  
HETATM   48  H17 UNL     1       5.015  -3.162   0.636  1.00  0.00           H  
HETATM   49  H18 UNL     1       3.391  -2.052  -1.722  1.00  0.00           H  
HETATM   50  H19 UNL     1       2.953  -3.289  -0.517  1.00  0.00           H  
HETATM   51  H20 UNL     1       3.559  -0.348   0.170  1.00  0.00           H  
HETATM   52  H21 UNL     1       2.993  -1.584   1.299  1.00  0.00           H  
HETATM   53  H22 UNL     1       1.188  -0.070   0.451  1.00  0.00           H  
HETATM   54  H23 UNL     1       1.612  -0.547  -1.193  1.00  0.00           H  
HETATM   55  H24 UNL     1       0.614  -2.455   0.985  1.00  0.00           H  
HETATM   56  H25 UNL     1       0.993  -2.925  -0.759  1.00  0.00           H  
HETATM   57  H26 UNL     1      -1.355  -2.674  -0.447  1.00  0.00           H  
HETATM   58  H27 UNL     1      -0.768  -1.328  -1.523  1.00  0.00           H  
HETATM   59  H28 UNL     1      -1.430  -1.104   1.463  1.00  0.00           H  
HETATM   60  H29 UNL     1      -0.771   0.224   0.504  1.00  0.00           H  
HETATM   61  H30 UNL     1      -3.138   0.527   0.542  1.00  0.00           H  
HETATM   62  H31 UNL     1      -2.631   0.065  -1.090  1.00  0.00           H  
HETATM   63  H32 UNL     1      -3.307  -2.270  -0.755  1.00  0.00           H  
HETATM   64  H33 UNL     1      -3.801  -1.878   0.982  1.00  0.00           H  
HETATM   65  H34 UNL     1      -4.908  -0.681  -1.585  1.00  0.00           H  
HETATM   66  H35 UNL     1      -5.657  -1.982  -0.627  1.00  0.00           H  
HETATM   67  H36 UNL     1      -7.107  -0.983   1.466  1.00  0.00           H  
HETATM   68  H37 UNL     1      -5.195   3.162   0.169  1.00  0.00           H  
HETATM   69  H38 UNL     1      -7.297   3.903  -0.794  1.00  0.00           H  
HETATM   70  H39 UNL     1      -6.365   2.736  -1.851  1.00  0.00           H  
HETATM   71  H40 UNL     1      -7.194   0.569  -2.291  1.00  0.00           H  
HETATM   72  H41 UNL     1      -9.107  -0.945  -2.370  1.00  0.00           H  
HETATM   73  H42 UNL     1     -11.157  -0.398  -1.088  1.00  0.00           H  
HETATM   74  H43 UNL     1     -11.296   1.675   0.285  1.00  0.00           H  
HETATM   75  H44 UNL     1      -9.343   3.201   0.352  1.00  0.00           H  
HETATM   76  H45 UNL     1      -7.055   4.695   1.186  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3   35   36
CONECT    3    4   37   38
CONECT    4    5   39   40
CONECT    5    6   41   42
CONECT    6    7   43   44
CONECT    7    8   45   46
CONECT    8    9   47   48
CONECT    9   10   49   50
CONECT   10   11   51   52
CONECT   11   12   53   54
CONECT   12   13   55   56
CONECT   13   14   57   58
CONECT   14   15   59   60
CONECT   15   16   61   62
CONECT   16   17   63   64
CONECT   17   18   65   66
CONECT   18   19   20   20
CONECT   19   67
CONECT   20   21
CONECT   21   22   29   68
CONECT   22   23   69   70
CONECT   23   24   24   28
CONECT   24   25   71
CONECT   25   26   26   72
CONECT   26   27   73
CONECT   27   28   28   74
CONECT   28   75
CONECT   29   30   30   31
CONECT   31   76
END

HMDB0062342
     RDKit          3D
N-Stearoyl phenylalanine
 76 76  0  0  0  0  0  0  0  0999 V2000
   10.4671    0.5883    2.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3263    1.0849    0.6884 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9152    1.5022    0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9370    0.3834    0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2367   -0.7607   -0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2785   -1.9182   -0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8729   -1.5012   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9658   -2.7098   -0.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5244   -2.3334   -0.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721   -1.2897    0.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5538   -0.9324   -0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6380   -2.1151   -0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7526   -1.7268   -0.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3500   -0.6958    0.4207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371   -0.3051   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6619   -1.4887   -0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0240   -1.0746   -0.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6726   -0.0436    0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2035   -0.5267    1.5068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6859    1.1117   -0.0230 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0478    2.4133    0.2265 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9713    2.8658   -0.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1649    1.9663   -0.9637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0953    0.8138   -1.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1829   -0.0356   -1.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3197    0.2768   -1.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4068    1.4330   -0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3162    2.2807   -0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7750    2.6089    1.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0781    1.7164    2.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1480    3.9232    1.8296 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8601   -0.3339    2.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0985    1.3806    2.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5142    0.3209    2.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6573    0.3376   -0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0025    1.9744    0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6365    2.3864    1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8771    1.8933   -0.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9136    0.7920    0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8827    0.0686    1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1641   -0.3943   -1.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2845   -1.1062   -0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2963   -2.2195    0.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6053   -2.7616   -0.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8401   -1.1927   -1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5597   -0.6849    0.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2771   -3.4490   -1.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0149   -3.1619    0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3908   -2.0520   -1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9526   -3.2895   -0.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5585   -0.3481    0.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9932   -1.5843    1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1884   -0.0703    0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -0.5466   -1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6141   -2.4555    0.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9932   -2.9251   -0.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3548   -2.6740   -0.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676   -1.3276   -1.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4303   -1.1044    1.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7709    0.2243    0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1378    0.5268    0.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6314    0.0654   -1.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3071   -2.2697   -0.7552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8009   -1.8779    0.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9075   -0.6810   -1.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6570   -1.9817   -0.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1067   -0.9828    1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1946    3.1616    0.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2971    3.9030   -0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3652    2.7358   -1.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1940    0.5691   -2.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1075   -0.9449   -2.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1572   -0.3975   -1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2965    1.6747    0.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3427    3.2007    0.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0549    4.6954    1.1858 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  1  0
  6  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  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
 18 20  2  3
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 21 29  1  0
 29 30  2  0
 29 31  1  0
 28 23  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
  9 50  1  0
 10 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 12 56  1  0
 13 57  1  0
 13 58  1  0
 14 59  1  0
 14 60  1  0
 15 61  1  0
 15 62  1  0
 16 63  1  0
 16 64  1  0
 17 65  1  0
 17 66  1  0
 19 67  1  0
 21 68  1  1
 22 69  1  0
 22 70  1  0
 24 71  1  0
 25 72  1  0
 26 73  1  0
 27 74  1  0
 28 75  1  0
 31 76  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₇H₄₅NO₃

Average Molecular Weight

431.661

Monoisotopic Molecular Weight

431.339944313

IUPAC Name

(2S)-2-[(1-hydroxyoctadecylidene)amino]-3-phenylpropanoic acid

Traditional Name

(2S)-2-[(1-hydroxyoctadecylidene)amino]-3-phenylpropanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](CC1=CC=CC=C1)(N=C(O)CCCCCCCCCCCCCCCCC)C(O)=O

InChI Identifier

InChI=1S/C27H45NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-22-26(29)28-25(27(30)31)23-24-20-17-16-18-21-24/h16-18,20-21,25H,2-15,19,22-23H2,1H3,(H,28,29)(H,30,31)/t25-/m0/s1

InChI Key

PHZQULSGYVCYNC-VWLOTQADSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
N-acyl-l-alpha-amino acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
3-phenylpropanoic-acid
Amphetamine or derivatives
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
N-acyl-amine
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N-acyl amines (LMFA08020093 )

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	5.1e-05 g/l	ALOGPS
LogP	8.21	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	7.87	ALOGPS
logP	9.09	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	4.18	ChemAxon
pKa (Strongest Basic)	1.58	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.89 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	128.72 m³·mol⁻¹	ChemAxon
Polarizability	54.72 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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
DarkChem	[M+H]+	211.878	31661259
DarkChem	[M-H]-	208.693	31661259
DeepCCS	[M+H]+	200.952	30932474
DeepCCS	[M-H]-	198.594	30932474
DeepCCS	[M-2H]-	232.479	30932474
DeepCCS	[M+Na]+	207.706	30932474
AllCCS	[M+H]+	216.5	32859911
AllCCS	[M+H-H2O]+	214.7	32859911
AllCCS	[M+NH4]+	218.2	32859911
AllCCS	[M+Na]+	218.7	32859911
AllCCS	[M-H]-	208.4	32859911
AllCCS	[M+Na-2H]-	211.1	32859911
AllCCS	[M+HCOO]-	214.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Stearoyl phenylalanine	[H][C@@](CC1=CC=CC=C1)(N=C(O)CCCCCCCCCCCCCCCCC)C(O)=O	3380.8	Standard polar	33892256
N-Stearoyl phenylalanine	[H][C@@](CC1=CC=CC=C1)(N=C(O)CCCCCCCCCCCCCCCCC)C(O)=O	3071.0	Standard non polar	33892256
N-Stearoyl phenylalanine	[H][C@@](CC1=CC=CC=C1)(N=C(O)CCCCCCCCCCCCCCCCC)C(O)=O	3302.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Stearoyl phenylalanine,1TMS,isomer #1	CCCCCCCCCCCCCCCCCC(=N[C@@H](CC1=CC=CC=C1)C(=O)O)O[Si](C)(C)C	3351.2	Semi standard non polar	33892256
N-Stearoyl phenylalanine,1TMS,isomer #2	CCCCCCCCCCCCCCCCCC(O)=N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	3338.6	Semi standard non polar	33892256
N-Stearoyl phenylalanine,2TMS,isomer #1	CCCCCCCCCCCCCCCCCC(=N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	3317.6	Semi standard non polar	33892256
N-Stearoyl phenylalanine,1TBDMS,isomer #1	CCCCCCCCCCCCCCCCCC(=N[C@@H](CC1=CC=CC=C1)C(=O)O)O[Si](C)(C)C(C)(C)C	3601.3	Semi standard non polar	33892256
N-Stearoyl phenylalanine,1TBDMS,isomer #2	CCCCCCCCCCCCCCCCCC(O)=N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	3590.7	Semi standard non polar	33892256
N-Stearoyl phenylalanine,2TBDMS,isomer #1	CCCCCCCCCCCCCCCCCC(=N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3813.6	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 - N-Stearoyl phenylalanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9443000000-de7104e2914ca235f1ac	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Stearoyl phenylalanine GC-MS (2 TMS) - 70eV, Positive	splash10-06r6-9310330000-5294e0ffe73865e789e4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Stearoyl phenylalanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Stearoyl phenylalanine 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 - N-Stearoyl phenylalanine 10V, Positive-QTOF	splash10-03e9-2912800000-777fd2740127ecb0a258	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Stearoyl phenylalanine 20V, Positive-QTOF	splash10-02t9-1920000000-e1df9b78f613abe93fb8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Stearoyl phenylalanine 40V, Positive-QTOF	splash10-0006-9710000000-86777225280888f4e7c2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Stearoyl phenylalanine 10V, Negative-QTOF	splash10-001i-0002900000-2b0f23ddae9651e51aae	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Stearoyl phenylalanine 20V, Negative-QTOF	splash10-02ar-3697700000-012376026ac388fe8d37	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Stearoyl phenylalanine 40V, Negative-QTOF	splash10-00kf-9430000000-2365a3275c6a6bcc61a9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Stearoyl phenylalanine 10V, Negative-QTOF	splash10-03e9-0201900000-d963450f3f6aa48adb6f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Stearoyl phenylalanine 20V, Negative-QTOF	splash10-0fsl-4941400000-79e29a30c4c12a3ac1f3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Stearoyl phenylalanine 40V, Negative-QTOF	splash10-00kf-8931000000-9848ab7763a925b68c33	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Stearoyl phenylalanine 10V, Positive-QTOF	splash10-0159-2921400000-da0b13e719cc88034cc9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Stearoyl phenylalanine 20V, Positive-QTOF	splash10-06dj-4911000000-b093af6cb24c2fb85953	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Stearoyl phenylalanine 40V, Positive-QTOF	splash10-0597-9600000000-d3e87a3505e8ef10cf7f	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

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

6710071

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

Bradshaw HB, Walker JM: The expanding field of cannabimimetic and related lipid mediators. Br J Pharmacol. 2005 Feb;144(4):459-65. doi: 10.1038/sj.bjp.0706093. [PubMed:15655504 ]
Grapov D, Adams SH, Pedersen TL, Garvey WT, Newman JW: Type 2 diabetes associated changes in the plasma non-esterified fatty acids, oxylipins and endocannabinoids. PLoS One. 2012;7(11):e48852. doi: 10.1371/journal.pone.0048852. Epub 2012 Nov 8. [PubMed:23144998 ]
Raboune S, Stuart JM, Leishman E, Takacs SM, Rhodes B, Basnet A, Jameyfield E, McHugh D, Widlanski T, Bradshaw HB: Novel endogenous N-acyl amides activate TRPV1-4 receptors, BV-2 microglia, and are regulated in brain in an acute model of inflammation. Front Cell Neurosci. 2014 Aug 1;8:195. doi: 10.3389/fncel.2014.00195. eCollection 2014. [PubMed:25136293 ]
Cohen LJ, Esterhazy D, Kim SH, Lemetre C, Aguilar RR, Gordon EA, Pickard AJ, Cross JR, Emiliano AB, Han SM, Chu J, Vila-Farres X, Kaplitt J, Rogoz A, Calle PY, Hunter C, Bitok JK, Brady SF: Commensal bacteria make GPCR ligands that mimic human signalling molecules. Nature. 2017 Sep 7;549(7670):48-53. doi: 10.1038/nature23874. Epub 2017 Aug 30. [PubMed:28854168 ]
Bradshaw HB, Raboune S, Hollis JL: Opportunistic activation of TRP receptors by endogenous lipids: exploiting lipidomics to understand TRP receptor cellular communication. Life Sci. 2013 Mar 19;92(8-9):404-9. doi: 10.1016/j.lfs.2012.11.008. Epub 2012 Nov 20. [PubMed:23178153 ]
Long JZ, Roche AM, Berdan CA, Louie SM, Roberts AJ, Svensson KJ, Dou FY, Bateman LA, Mina AI, Deng Z, Jedrychowski MP, Lin H, Kamenecka TM, Asara JM, Griffin PR, Banks AS, Nomura DK, Spiegelman BM: Ablation of PM20D1 reveals N-acyl amino acid control of metabolism and nociception. Proc Natl Acad Sci U S A. 2018 Jul 17;115(29):E6937-E6945. doi: 10.1073/pnas.1803389115. Epub 2018 Jul 2. [PubMed:29967167 ]

Showing metabocard for N-Stearoyl phenylalanine (HMDB0062342)

MOL for HMDB0062342 (N-Stearoyl phenylalanine)

3D MOL for HMDB0062342 (N-Stearoyl phenylalanine)

3D SDF for HMDB0062342 (N-Stearoyl phenylalanine)

3D-SDF for HMDB0062342 (N-Stearoyl phenylalanine)

PDB for HMDB0062342 (N-Stearoyl phenylalanine)

3D PDB for HMDB0062342 (N-Stearoyl phenylalanine)

SMILES for HMDB0062342 (N-Stearoyl phenylalanine)

INCHI for HMDB0062342 (N-Stearoyl phenylalanine)

Structure for HMDB0062342 (N-Stearoyl phenylalanine)

3D Structure for HMDB0062342 (N-Stearoyl phenylalanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra