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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-16 03:44:36 UTC

Update Date

2022-03-07 03:17:53 UTC

HMDB ID

HMDB0062339

Secondary Accession Numbers

HMDB62339

Metabolite Identification

Common Name

N-Palmitoyl phenylalanine

Description

N-palmitoyl 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 Palmitic 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-Palmitoyl 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-Palmitoyl 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          

 30 30  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
   -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
  2 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
M  END

HMDB0062339
     RDKit          3D
N-Palmitoyl phenylalanine
 70 70  0  0  0  0  0  0  0  0999 V2000
    6.3416    2.4616    0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7072    2.3352    0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0302    1.0333   -0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0800   -0.1925    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0585   -0.8981    0.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8770   -1.4668    0.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9819   -0.4708   -0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7862   -1.1491   -1.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9378   -0.0873   -1.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3887    0.9061   -0.6584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5347    0.2393    0.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3407   -0.4759   -0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4697   -1.1144    0.8415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6403   -1.8500    0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5308   -0.9105   -0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7204   -1.6335   -1.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4029   -2.6765   -1.9944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8202   -1.3607   -0.7867 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9968   -0.9125   -0.3481 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9494    0.5551    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2825    0.9743    0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1858    1.6374   -0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4345    2.0274    0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8464    1.7660    1.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9618    1.1080    2.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7148    0.7185    1.9298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0352   -1.0221   -1.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6716   -1.2681   -2.5865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3521   -0.8528   -1.1147 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259    2.2778   -0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1691    3.5638    0.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1577    1.8519    1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7579    3.0969   -0.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4930    2.6621    0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1484    1.1783   -0.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4836    0.9755   -1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6346   -1.0100   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9502   -0.0405    1.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6441   -0.3085    1.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5261   -1.7972    1.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3159   -2.0697    1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1634   -2.2385   -0.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6221    0.2144    0.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4833    0.0788   -1.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2147   -1.7568   -1.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2682   -1.8264   -0.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1187   -0.4941   -2.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6166    0.5114   -2.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1834    1.4778   -0.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8031    1.6618   -1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1494    0.9749    1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1499   -0.5653    0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7681   -1.2113   -0.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2394    0.2657   -0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8399   -0.2836    1.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1793   -1.8151    1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1988   -2.5890   -0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1805   -2.4513    1.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9125   -0.1431    0.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9614   -0.5087   -1.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2787   -3.6233   -1.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4246   -1.4480    0.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5635    1.2203   -0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2333    0.6078    1.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8563    1.8446   -1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1065    2.5408   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8356    2.0771    1.8730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2651    0.8970    3.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9961    0.1991    2.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7843   -1.4183   -0.4057 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
 16 18  2  3
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 19 27  1  0
 27 28  2  0
 27 29  1  0
 26 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  0
 12 54  1  0
 13 55  1  0
 13 56  1  0
 14 57  1  0
 14 58  1  0
 15 59  1  0
 15 60  1  0
 17 61  1  0
 19 62  1  1
 20 63  1  0
 20 64  1  0
 22 65  1  0
 23 66  1  0
 24 67  1  0
 25 68  1  0
 26 69  1  0
 29 70  1  0
M  END


  Mrv1652303161704442D          

 30 30  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
   -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
  2 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062339

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17-20-24(27)26-23(25(28)29)21-22-18-15-14-16-19-22/h14-16,18-19,23H,2-13,17,20-21H2,1H3,(H,26,27)(H,28,29)/t23-/m0/s1

> <INCHI_KEY>
BAHIJPSQSKWCJX-QHCPKHFHSA-N

> <FORMULA>
C25H41NO3

> <MOLECULAR_WEIGHT>
403.607

> <EXACT_MASS>
403.308644184

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
50.43423291028502

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.98

> <JCHEM_LOGP>
8.195994275

> <ALOGPS_LOGS>
-6.55

> <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>
119.52169999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.14e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062339
     RDKit          3D
N-Palmitoyl phenylalanine
 70 70  0  0  0  0  0  0  0  0999 V2000
    6.3416    2.4616    0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7072    2.3352    0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0302    1.0333   -0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0800   -0.1925    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0585   -0.8981    0.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8770   -1.4668    0.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9819   -0.4708   -0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7862   -1.1491   -1.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9378   -0.0873   -1.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3887    0.9061   -0.6584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5347    0.2393    0.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3407   -0.4759   -0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4697   -1.1144    0.8415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6403   -1.8500    0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5308   -0.9105   -0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7204   -1.6335   -1.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4029   -2.6765   -1.9944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8202   -1.3607   -0.7867 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9968   -0.9125   -0.3481 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9494    0.5551    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2825    0.9743    0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1858    1.6374   -0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4345    2.0274    0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8464    1.7660    1.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9618    1.1080    2.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7148    0.7185    1.9298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0352   -1.0221   -1.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6716   -1.2681   -2.5865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3521   -0.8528   -1.1147 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259    2.2778   -0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1691    3.5638    0.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1577    1.8519    1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7579    3.0969   -0.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4930    2.6621    0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1484    1.1783   -0.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4836    0.9755   -1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6346   -1.0100   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9502   -0.0405    1.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6441   -0.3085    1.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5261   -1.7972    1.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3159   -2.0697    1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1634   -2.2385   -0.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6221    0.2144    0.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4833    0.0788   -1.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2147   -1.7568   -1.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2682   -1.8264   -0.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1187   -0.4941   -2.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6166    0.5114   -2.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1834    1.4778   -0.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8031    1.6618   -1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1494    0.9749    1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1499   -0.5653    0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7681   -1.2113   -0.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2394    0.2657   -0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8399   -0.2836    1.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1793   -1.8151    1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1988   -2.5890   -0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1805   -2.4513    1.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9125   -0.1431    0.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9614   -0.5087   -1.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2787   -3.6233   -1.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4246   -1.4480    0.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5635    1.2203   -0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2333    0.6078    1.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8563    1.8446   -1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1065    2.5408   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8356    2.0771    1.8730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2651    0.8970    3.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9961    0.1991    2.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7843   -1.4183   -0.4057 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
 16 18  2  3
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 19 27  1  0
 27 28  2  0
 27 29  1  0
 26 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  0
 12 54  1  0
 13 55  1  0
 13 56  1  0
 14 57  1  0
 14 58  1  0
 15 59  1  0
 15 60  1  0
 17 61  1  0
 19 62  1  1
 20 63  1  0
 20 64  1  0
 22 65  1  0
 23 66  1  0
 24 67  1  0
 25 68  1  0
 26 69  1  0
 29 70  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      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -9.336 -10.010   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10   28                                             
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                                                            
CONECT   28    2   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   60    0
END

COMPND    HMDB0062339
HETATM    1  C1  UNL     1       6.342   2.462   0.631  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.707   2.335   0.067  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.030   1.033  -0.535  1.00  0.00           C  
HETATM    4  C4  UNL     1       8.080  -0.192   0.222  1.00  0.00           C  
HETATM    5  C5  UNL     1       7.058  -0.898   0.955  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.877  -1.467   0.275  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.982  -0.471  -0.361  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.786  -1.149  -1.040  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.938  -0.087  -1.651  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.389   0.906  -0.658  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.535   0.239   0.397  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.341  -0.476  -0.256  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.470  -1.114   0.842  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.640  -1.850   0.260  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.531  -0.911  -0.483  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.720  -1.634  -1.069  1.00  0.00           C  
HETATM   17  O1  UNL     1      -3.403  -2.677  -1.994  1.00  0.00           O  
HETATM   18  N1  UNL     1      -4.820  -1.361  -0.787  1.00  0.00           N  
HETATM   19  C17 UNL     1      -5.997  -0.912  -0.348  1.00  0.00           C  
HETATM   20  C18 UNL     1      -5.949   0.555   0.161  1.00  0.00           C  
HETATM   21  C19 UNL     1      -7.282   0.974   0.622  1.00  0.00           C  
HETATM   22  C20 UNL     1      -8.186   1.637  -0.191  1.00  0.00           C  
HETATM   23  C21 UNL     1      -9.434   2.027   0.244  1.00  0.00           C  
HETATM   24  C22 UNL     1      -9.846   1.766   1.541  1.00  0.00           C  
HETATM   25  C23 UNL     1      -8.962   1.108   2.364  1.00  0.00           C  
HETATM   26  C24 UNL     1      -7.715   0.719   1.930  1.00  0.00           C  
HETATM   27  C25 UNL     1      -7.035  -1.022  -1.428  1.00  0.00           C  
HETATM   28  O2  UNL     1      -6.672  -1.268  -2.587  1.00  0.00           O  
HETATM   29  O3  UNL     1      -8.352  -0.853  -1.115  1.00  0.00           O  
HETATM   30  H1  UNL     1       5.626   2.278  -0.227  1.00  0.00           H  
HETATM   31  H2  UNL     1       6.169   3.564   0.915  1.00  0.00           H  
HETATM   32  H3  UNL     1       6.158   1.852   1.510  1.00  0.00           H  
HETATM   33  H4  UNL     1       7.758   3.097  -0.780  1.00  0.00           H  
HETATM   34  H5  UNL     1       8.493   2.662   0.828  1.00  0.00           H  
HETATM   35  H6  UNL     1       9.148   1.178  -0.914  1.00  0.00           H  
HETATM   36  H7  UNL     1       7.484   0.975  -1.522  1.00  0.00           H  
HETATM   37  H8  UNL     1       8.635  -1.010  -0.443  1.00  0.00           H  
HETATM   38  H9  UNL     1       8.950  -0.041   1.004  1.00  0.00           H  
HETATM   39  H10 UNL     1       6.644  -0.309   1.845  1.00  0.00           H  
HETATM   40  H11 UNL     1       7.526  -1.797   1.537  1.00  0.00           H  
HETATM   41  H12 UNL     1       5.316  -2.070   1.066  1.00  0.00           H  
HETATM   42  H13 UNL     1       6.163  -2.238  -0.504  1.00  0.00           H  
HETATM   43  H14 UNL     1       4.622   0.214   0.439  1.00  0.00           H  
HETATM   44  H15 UNL     1       5.483   0.079  -1.148  1.00  0.00           H  
HETATM   45  H16 UNL     1       4.215  -1.757  -1.862  1.00  0.00           H  
HETATM   46  H17 UNL     1       3.268  -1.826  -0.360  1.00  0.00           H  
HETATM   47  H18 UNL     1       2.119  -0.494  -2.279  1.00  0.00           H  
HETATM   48  H19 UNL     1       3.617   0.511  -2.320  1.00  0.00           H  
HETATM   49  H20 UNL     1       3.183   1.478  -0.158  1.00  0.00           H  
HETATM   50  H21 UNL     1       1.803   1.662  -1.237  1.00  0.00           H  
HETATM   51  H22 UNL     1       1.149   0.975   1.121  1.00  0.00           H  
HETATM   52  H23 UNL     1       2.150  -0.565   0.848  1.00  0.00           H  
HETATM   53  H24 UNL     1       0.768  -1.211  -0.953  1.00  0.00           H  
HETATM   54  H25 UNL     1      -0.239   0.266  -0.859  1.00  0.00           H  
HETATM   55  H26 UNL     1      -0.840  -0.284   1.508  1.00  0.00           H  
HETATM   56  H27 UNL     1       0.179  -1.815   1.427  1.00  0.00           H  
HETATM   57  H28 UNL     1      -1.199  -2.589  -0.476  1.00  0.00           H  
HETATM   58  H29 UNL     1      -2.180  -2.451   1.023  1.00  0.00           H  
HETATM   59  H30 UNL     1      -2.913  -0.143   0.199  1.00  0.00           H  
HETATM   60  H31 UNL     1      -1.961  -0.509  -1.360  1.00  0.00           H  
HETATM   61  H32 UNL     1      -3.279  -3.623  -1.612  1.00  0.00           H  
HETATM   62  H33 UNL     1      -6.425  -1.448   0.581  1.00  0.00           H  
HETATM   63  H34 UNL     1      -5.564   1.220  -0.642  1.00  0.00           H  
HETATM   64  H35 UNL     1      -5.233   0.608   1.013  1.00  0.00           H  
HETATM   65  H36 UNL     1      -7.856   1.845  -1.218  1.00  0.00           H  
HETATM   66  H37 UNL     1     -10.106   2.541  -0.423  1.00  0.00           H  
HETATM   67  H38 UNL     1     -10.836   2.077   1.873  1.00  0.00           H  
HETATM   68  H39 UNL     1      -9.265   0.897   3.377  1.00  0.00           H  
HETATM   69  H40 UNL     1      -6.996   0.199   2.554  1.00  0.00           H  
HETATM   70  H41 UNL     1      -8.784  -1.418  -0.406  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3   33   34
CONECT    3    4   35   36
CONECT    4    5   37   38
CONECT    5    6   39   40
CONECT    6    7   41   42
CONECT    7    8   43   44
CONECT    8    9   45   46
CONECT    9   10   47   48
CONECT   10   11   49   50
CONECT   11   12   51   52
CONECT   12   13   53   54
CONECT   13   14   55   56
CONECT   14   15   57   58
CONECT   15   16   59   60
CONECT   16   17   18   18
CONECT   17   61
CONECT   18   19
CONECT   19   20   27   62
CONECT   20   21   63   64
CONECT   21   22   22   26
CONECT   22   23   65
CONECT   23   24   24   66
CONECT   24   25   67
CONECT   25   26   26   68
CONECT   26   69
CONECT   27   28   28   29
CONECT   29   70
END

HMDB0062339
     RDKit          3D
N-Palmitoyl phenylalanine
 70 70  0  0  0  0  0  0  0  0999 V2000
    6.3416    2.4616    0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7072    2.3352    0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0302    1.0333   -0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0800   -0.1925    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0585   -0.8981    0.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8770   -1.4668    0.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9819   -0.4708   -0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7862   -1.1491   -1.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9378   -0.0873   -1.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3887    0.9061   -0.6584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5347    0.2393    0.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3407   -0.4759   -0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4697   -1.1144    0.8415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6403   -1.8500    0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5308   -0.9105   -0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7204   -1.6335   -1.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4029   -2.6765   -1.9944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8202   -1.3607   -0.7867 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9968   -0.9125   -0.3481 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9494    0.5551    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2825    0.9743    0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1858    1.6374   -0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4345    2.0274    0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8464    1.7660    1.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9618    1.1080    2.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7148    0.7185    1.9298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0352   -1.0221   -1.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6716   -1.2681   -2.5865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3521   -0.8528   -1.1147 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259    2.2778   -0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1691    3.5638    0.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1577    1.8519    1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7579    3.0969   -0.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4930    2.6621    0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1484    1.1783   -0.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4836    0.9755   -1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6346   -1.0100   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9502   -0.0405    1.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6441   -0.3085    1.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5261   -1.7972    1.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3159   -2.0697    1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1634   -2.2385   -0.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6221    0.2144    0.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4833    0.0788   -1.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2147   -1.7568   -1.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2682   -1.8264   -0.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1187   -0.4941   -2.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6166    0.5114   -2.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1834    1.4778   -0.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8031    1.6618   -1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1494    0.9749    1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1499   -0.5653    0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7681   -1.2113   -0.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2394    0.2657   -0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8399   -0.2836    1.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1793   -1.8151    1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1988   -2.5890   -0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1805   -2.4513    1.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9125   -0.1431    0.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9614   -0.5087   -1.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2787   -3.6233   -1.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4246   -1.4480    0.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5635    1.2203   -0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2333    0.6078    1.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8563    1.8446   -1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1065    2.5408   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8356    2.0771    1.8730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2651    0.8970    3.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9961    0.1991    2.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7843   -1.4183   -0.4057 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
 16 18  2  3
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 19 27  1  0
 27 28  2  0
 27 29  1  0
 26 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  0
 12 54  1  0
 13 55  1  0
 13 56  1  0
 14 57  1  0
 14 58  1  0
 15 59  1  0
 15 60  1  0
 17 61  1  0
 19 62  1  1
 20 63  1  0
 20 64  1  0
 22 65  1  0
 23 66  1  0
 24 67  1  0
 25 68  1  0
 26 69  1  0
 29 70  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₅H₄₁NO₃

Average Molecular Weight

403.607

Monoisotopic Molecular Weight

403.308644184

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17-20-24(27)26-23(25(28)29)21-22-18-15-14-16-19-22/h14-16,18-19,23H,2-13,17,20-21H2,1H3,(H,26,27)(H,28,29)/t23-/m0/s1

InChI Key

BAHIJPSQSKWCJX-QHCPKHFHSA-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 or derivatives
N-acyl-alpha-amino acid
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
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N-acyl amines (LMFA08020091 )

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	0.0001 g/l	ALOGPS
LogP	7.30	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	6.98	ALOGPS
logP	8.2	ChemAxon
logS	-6.6	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	18	ChemAxon
Refractivity	119.52 m³·mol⁻¹	ChemAxon
Polarizability	50.43 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]+	203.318	31661259
DarkChem	[M-H]-	205.723	31661259
DeepCCS	[M+H]+	194.511	30932474
DeepCCS	[M-H]-	192.153	30932474
DeepCCS	[M-2H]-	225.76	30932474
DeepCCS	[M+Na]+	200.986	30932474
AllCCS	[M+H]+	207.6	32859911
AllCCS	[M+H-H2O]+	205.5	32859911
AllCCS	[M+NH4]+	209.4	32859911
AllCCS	[M+Na]+	210.0	32859911
AllCCS	[M-H]-	201.7	32859911
AllCCS	[M+Na-2H]-	203.9	32859911
AllCCS	[M+HCOO]-	206.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Palmitoyl phenylalanine	[H][C@@](CC1=CC=CC=C1)(N=C(O)CCCCCCCCCCCCCCC)C(O)=O	3304.5	Standard polar	33892256
N-Palmitoyl phenylalanine	[H][C@@](CC1=CC=CC=C1)(N=C(O)CCCCCCCCCCCCCCC)C(O)=O	2913.8	Standard non polar	33892256
N-Palmitoyl phenylalanine	[H][C@@](CC1=CC=CC=C1)(N=C(O)CCCCCCCCCCCCCCC)C(O)=O	3091.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Palmitoyl phenylalanine,1TMS,isomer #1	CCCCCCCCCCCCCCCC(=N[C@@H](CC1=CC=CC=C1)C(=O)O)O[Si](C)(C)C	3155.6	Semi standard non polar	33892256
N-Palmitoyl phenylalanine,1TMS,isomer #2	CCCCCCCCCCCCCCCC(O)=N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	3138.8	Semi standard non polar	33892256
N-Palmitoyl phenylalanine,2TMS,isomer #1	CCCCCCCCCCCCCCCC(=N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	3121.2	Semi standard non polar	33892256
N-Palmitoyl phenylalanine,1TBDMS,isomer #1	CCCCCCCCCCCCCCCC(=N[C@@H](CC1=CC=CC=C1)C(=O)O)O[Si](C)(C)C(C)(C)C	3395.3	Semi standard non polar	33892256
N-Palmitoyl phenylalanine,1TBDMS,isomer #2	CCCCCCCCCCCCCCCC(O)=N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	3385.5	Semi standard non polar	33892256
N-Palmitoyl phenylalanine,2TBDMS,isomer #1	CCCCCCCCCCCCCCCC(=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	3605.4	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-Palmitoyl phenylalanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9445000000-6308da786906ea2c9daa	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Palmitoyl phenylalanine GC-MS (2 TMS) - 70eV, Positive	splash10-001l-9200320000-4ea4a9e0e9cd644cd7f8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Palmitoyl 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-Palmitoyl phenylalanine 10V, Positive-QTOF	splash10-0iki-2906400000-08f014d415f8a3a3f55a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Palmitoyl phenylalanine 20V, Positive-QTOF	splash10-02t9-2921000000-70e7423c76d6f8d7605b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Palmitoyl phenylalanine 40V, Positive-QTOF	splash10-0006-9600000000-6e3724f582f024c04014	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Palmitoyl phenylalanine 10V, Negative-QTOF	splash10-0udi-0015900000-d7b7d0e9e4340aaef5c0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Palmitoyl phenylalanine 20V, Negative-QTOF	splash10-115i-2579300000-d145fea9cffbb167f691	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Palmitoyl phenylalanine 40V, Negative-QTOF	splash10-00kf-9520000000-6be31cddd4e9232fa454	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Palmitoyl phenylalanine 10V, Negative-QTOF	splash10-0ue9-1409800000-a4ea3bd469a00de3c6a7	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Palmitoyl phenylalanine 20V, Negative-QTOF	splash10-0udi-3941400000-0f463134a96c0a4edb52	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Palmitoyl phenylalanine 40V, Negative-QTOF	splash10-0006-8950000000-2f3e7ee9823a4d367c80	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Palmitoyl phenylalanine 10V, Positive-QTOF	splash10-0gb9-1913300000-17cafc425cb593dd526f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Palmitoyl phenylalanine 20V, Positive-QTOF	splash10-06dj-3911000000-d8d57c039fd9e14cbc58	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Palmitoyl phenylalanine 40V, Positive-QTOF	splash10-0596-9600000000-37c37e4b1c5e04a921f6	2021-09-25	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

181534

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-Palmitoyl phenylalanine (HMDB0062339)

MOL for HMDB0062339 (N-Palmitoyl phenylalanine)

3D MOL for HMDB0062339 (N-Palmitoyl phenylalanine)

3D SDF for HMDB0062339 (N-Palmitoyl phenylalanine)

3D-SDF for HMDB0062339 (N-Palmitoyl phenylalanine)

PDB for HMDB0062339 (N-Palmitoyl phenylalanine)

3D PDB for HMDB0062339 (N-Palmitoyl phenylalanine)

SMILES for HMDB0062339 (N-Palmitoyl phenylalanine)

INCHI for HMDB0062339 (N-Palmitoyl phenylalanine)

Structure for HMDB0062339 (N-Palmitoyl phenylalanine)

3D Structure for HMDB0062339 (N-Palmitoyl phenylalanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra