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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-07-27 21:14:25 UTC

Update Date

2021-10-01 16:48:34 UTC

HMDB ID

HMDB0241916

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Oleoyl Glycine

Description

N-oleoyl glycine, also known as MK-0518, raltegravirum, or isentress 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 an Oleic acid amide of Glycine. 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-Oleoyl Glycine 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-Oleoyl Glycine 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

  Mrv0541 10091315242D          

 32 34  0  0  0  0            999 V2000
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    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
   -1.3184   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1904   -6.2599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4453   -7.0445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704   -7.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7553   -7.7120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5253   -6.2599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 16 21  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 26 32  1  0  0  0  0
M  END

HMDB0241916
     RDKit          3D
N-Oleoyl Glycine
 61 60  0  0  0  0  0  0  0  0999 V2000
    8.5370   -0.3482    1.9877 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3079    0.6335    0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1616   -0.0526   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1088   -1.0448   -0.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6826   -0.7522   -0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0991   -0.2718    0.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6027   -0.1146    0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2403    0.8821   -0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7376    1.0465   -0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2381    2.2389   -0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2380    2.4652   -0.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9012    1.1522   -0.6537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4066    1.3199   -0.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0171   -0.0312   -1.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5308    0.1297   -1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1902   -1.1735   -1.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6748   -0.9994   -1.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2069   -0.6017   -0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4877   -0.5640    0.8124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5855   -0.2292   -0.0591 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0511    0.1486    1.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8887   -0.9300    2.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3929   -2.0552    1.9830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3140   -0.6615    3.5430 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9578    0.2478    2.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6029   -0.7906    2.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3161   -1.0793    1.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5776    1.3669    1.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2989    1.2274    0.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2379    0.6930   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1531   -0.6118   -0.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4194   -1.9597   -0.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2456   -1.4833   -1.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1277   -1.7066   -0.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3590   -0.0632   -1.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2425   -1.0528    1.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4443    0.7121    1.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0922   -1.0942    0.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2655    0.3191    1.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7156    1.8537   -0.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5890    0.6210   -1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1641    0.1714   -0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9027    3.0719   -0.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5879    2.8366    0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4377    3.1889   -1.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5175    0.8416   -1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6862    0.3754    0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7487    1.6637    0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6158    2.0397   -1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6847   -0.3418   -2.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7276   -0.7911   -0.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9225    0.6063   -0.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7941    0.8354   -1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7667   -1.5453   -2.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9872   -1.9324   -0.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8692   -0.2091   -2.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1367   -1.9487   -1.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1825   -0.2572   -0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4961    1.0271    1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1187    0.4263    1.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2622   -0.3357    3.6858 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  2  3
 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  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  0
 17 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 24 61  1  0
M  END

  Mrv0541 10091315242D          

 32 34  0  0  0  0            999 V2000
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    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
   -1.3184   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1904   -6.2599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4453   -7.0445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704   -7.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7553   -7.7120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5253   -6.2599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 16 21  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 26 32  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0241916

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(=O)C(O)=C(N=C1C(C)(C)NC(=O)C1=NN=C(C)O1)C(=O)NCC1=CC=C(F)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H21FN6O5/c1-10-25-26-17(32-10)16(30)24-20(2,3)19-23-13(14(28)18(31)27(19)4)15(29)22-9-11-5-7-12(21)8-6-11/h5-8,28H,9H2,1-4H3,(H,22,29)(H,24,30)

> <INCHI_KEY>
CZFFBEXEKNGXKS-UHFFFAOYSA-N

> <FORMULA>
C20H21FN6O5

> <MOLECULAR_WEIGHT>
444.4163

> <EXACT_MASS>
444.155746017

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
42.465830125440235

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-{2-[(5-methyl-1,3,4-oxadiazol-2-yl)formamido]propan-2-yl}-6-oxo-1,6-dihydropyrimidine-4-carboxamide

> <JCHEM_LOGP>
-0.3882265613333336

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.154755568024907

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.617113948405954

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4968036990609659

> <JCHEM_POLAR_SURFACE_AREA>
150.02

> <JCHEM_REFRACTIVITY>
112.59169999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
raltegravir

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0241916
     RDKit          3D
N-Oleoyl Glycine
 61 60  0  0  0  0  0  0  0  0999 V2000
    8.5370   -0.3482    1.9877 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3079    0.6335    0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1616   -0.0526   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1088   -1.0448   -0.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6826   -0.7522   -0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0991   -0.2718    0.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6027   -0.1146    0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2403    0.8821   -0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7376    1.0465   -0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2381    2.2389   -0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2380    2.4652   -0.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9012    1.1522   -0.6537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4066    1.3199   -0.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0171   -0.0312   -1.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5308    0.1297   -1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1902   -1.1735   -1.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6748   -0.9994   -1.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2069   -0.6017   -0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4877   -0.5640    0.8124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5855   -0.2292   -0.0591 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0511    0.1486    1.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8887   -0.9300    2.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3929   -2.0552    1.9830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3140   -0.6615    3.5430 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9578    0.2478    2.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6029   -0.7906    2.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3161   -1.0793    1.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5776    1.3669    1.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2989    1.2274    0.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2379    0.6930   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1531   -0.6118   -0.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4194   -1.9597   -0.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2456   -1.4833   -1.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1277   -1.7066   -0.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3590   -0.0632   -1.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2425   -1.0528    1.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4443    0.7121    1.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0922   -1.0942    0.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2655    0.3191    1.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7156    1.8537   -0.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5890    0.6210   -1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1641    0.1714   -0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9027    3.0719   -0.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5879    2.8366    0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4377    3.1889   -1.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5175    0.8416   -1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6862    0.3754    0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7487    1.6637    0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6158    2.0397   -1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6847   -0.3418   -2.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7276   -0.7911   -0.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9225    0.6063   -0.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7941    0.8354   -1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7667   -1.5453   -2.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9872   -1.9324   -0.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8692   -0.2091   -2.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1367   -1.9487   -1.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1825   -0.2572   -0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4961    1.0271    1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1187    0.4263    1.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2622   -0.3357    3.6858 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  2  3
 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  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  0
 17 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 24 61  1  0
M  END

HEADER    PROTEIN                                 09-OCT-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-OCT-13         0                                  
HETATM    1  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -5.335  -4.620   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -2.667  -4.620   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.461  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.541  -6.930   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -4.001  -8.470   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.668  -8.470   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -4.089 -11.685   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -4.565 -13.150   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -6.105 -13.150   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.010 -14.396   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.581 -11.685   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   30  F   UNK     0       1.334   3.850   0.000  0.00  0.00           F+0
HETATM   31  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8    2   10                                                  
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   16                                                       
CONECT   22    7   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   26                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

COMPND    HMDB0241916
HETATM    1  C1  UNL     1       8.537  -0.348   1.988  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.308   0.634   0.865  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.162  -0.053  -0.459  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.109  -1.045  -0.631  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.683  -0.752  -0.502  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.099  -0.272   0.747  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.603  -0.115   0.631  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.240   0.882  -0.417  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.738   1.047  -0.488  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.238   2.239  -0.259  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.238   2.465  -0.314  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.901   1.152  -0.654  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.407   1.320  -0.725  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.017  -0.031  -1.069  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.531   0.130  -1.142  1.00  0.00           C  
HETATM   16  C16 UNL     1      -5.190  -1.173  -1.478  1.00  0.00           C  
HETATM   17  C17 UNL     1      -6.675  -0.999  -1.544  1.00  0.00           C  
HETATM   18  C18 UNL     1      -7.207  -0.602  -0.233  1.00  0.00           C  
HETATM   19  O1  UNL     1      -6.488  -0.564   0.812  1.00  0.00           O  
HETATM   20  N1  UNL     1      -8.585  -0.229  -0.059  1.00  0.00           N  
HETATM   21  C19 UNL     1      -9.051   0.149   1.234  1.00  0.00           C  
HETATM   22  C20 UNL     1      -8.889  -0.930   2.244  1.00  0.00           C  
HETATM   23  O2  UNL     1      -8.393  -2.055   1.983  1.00  0.00           O  
HETATM   24  O3  UNL     1      -9.314  -0.661   3.543  1.00  0.00           O  
HETATM   25  H1  UNL     1       8.958   0.248   2.848  1.00  0.00           H  
HETATM   26  H2  UNL     1       7.603  -0.791   2.357  1.00  0.00           H  
HETATM   27  H3  UNL     1       9.316  -1.079   1.723  1.00  0.00           H  
HETATM   28  H4  UNL     1       7.578   1.367   1.144  1.00  0.00           H  
HETATM   29  H5  UNL     1       9.299   1.227   0.836  1.00  0.00           H  
HETATM   30  H6  UNL     1       8.238   0.693  -1.299  1.00  0.00           H  
HETATM   31  H7  UNL     1       9.153  -0.612  -0.583  1.00  0.00           H  
HETATM   32  H8  UNL     1       7.419  -1.960  -0.007  1.00  0.00           H  
HETATM   33  H9  UNL     1       7.246  -1.483  -1.683  1.00  0.00           H  
HETATM   34  H10 UNL     1       5.128  -1.707  -0.778  1.00  0.00           H  
HETATM   35  H11 UNL     1       5.359  -0.063  -1.353  1.00  0.00           H  
HETATM   36  H12 UNL     1       5.242  -1.053   1.561  1.00  0.00           H  
HETATM   37  H13 UNL     1       5.444   0.712   1.130  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.092  -1.094   0.496  1.00  0.00           H  
HETATM   39  H15 UNL     1       3.266   0.319   1.610  1.00  0.00           H  
HETATM   40  H16 UNL     1       3.716   1.854  -0.176  1.00  0.00           H  
HETATM   41  H17 UNL     1       3.589   0.621  -1.453  1.00  0.00           H  
HETATM   42  H18 UNL     1       1.164   0.171  -0.724  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.903   3.072  -0.026  1.00  0.00           H  
HETATM   44  H20 UNL     1      -0.588   2.837   0.681  1.00  0.00           H  
HETATM   45  H21 UNL     1      -0.438   3.189  -1.114  1.00  0.00           H  
HETATM   46  H22 UNL     1      -0.518   0.842  -1.659  1.00  0.00           H  
HETATM   47  H23 UNL     1      -0.686   0.375   0.104  1.00  0.00           H  
HETATM   48  H24 UNL     1      -2.749   1.664   0.272  1.00  0.00           H  
HETATM   49  H25 UNL     1      -2.616   2.040  -1.531  1.00  0.00           H  
HETATM   50  H26 UNL     1      -2.685  -0.342  -2.078  1.00  0.00           H  
HETATM   51  H27 UNL     1      -2.728  -0.791  -0.329  1.00  0.00           H  
HETATM   52  H28 UNL     1      -4.923   0.606  -0.242  1.00  0.00           H  
HETATM   53  H29 UNL     1      -4.794   0.835  -1.986  1.00  0.00           H  
HETATM   54  H30 UNL     1      -4.767  -1.545  -2.442  1.00  0.00           H  
HETATM   55  H31 UNL     1      -4.987  -1.932  -0.681  1.00  0.00           H  
HETATM   56  H32 UNL     1      -6.869  -0.209  -2.323  1.00  0.00           H  
HETATM   57  H33 UNL     1      -7.137  -1.949  -1.895  1.00  0.00           H  
HETATM   58  H34 UNL     1      -9.183  -0.257  -0.911  1.00  0.00           H  
HETATM   59  H35 UNL     1      -8.496   1.027   1.599  1.00  0.00           H  
HETATM   60  H36 UNL     1     -10.119   0.426   1.152  1.00  0.00           H  
HETATM   61  H37 UNL     1     -10.262  -0.336   3.686  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7   36   37
CONECT    7    8   38   39
CONECT    8    9   40   41
CONECT    9   10   10   42
CONECT   10   11   43
CONECT   11   12   44   45
CONECT   12   13   46   47
CONECT   13   14   48   49
CONECT   14   15   50   51
CONECT   15   16   52   53
CONECT   16   17   54   55
CONECT   17   18   56   57
CONECT   18   19   19   20
CONECT   20   21   58
CONECT   21   22   59   60
CONECT   22   23   23   24
CONECT   24   61
END

HMDB0241916
     RDKit          3D
N-Oleoyl Glycine
 61 60  0  0  0  0  0  0  0  0999 V2000
    8.5370   -0.3482    1.9877 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3079    0.6335    0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1616   -0.0526   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1088   -1.0448   -0.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6826   -0.7522   -0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0991   -0.2718    0.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6027   -0.1146    0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2403    0.8821   -0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7376    1.0465   -0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2381    2.2389   -0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2380    2.4652   -0.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9012    1.1522   -0.6537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4066    1.3199   -0.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0171   -0.0312   -1.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5308    0.1297   -1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1902   -1.1735   -1.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6748   -0.9994   -1.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2069   -0.6017   -0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4877   -0.5640    0.8124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5855   -0.2292   -0.0591 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0511    0.1486    1.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8887   -0.9300    2.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3929   -2.0552    1.9830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3140   -0.6615    3.5430 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9578    0.2478    2.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6029   -0.7906    2.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3161   -1.0793    1.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5776    1.3669    1.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2989    1.2274    0.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2379    0.6930   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1531   -0.6118   -0.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4194   -1.9597   -0.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2456   -1.4833   -1.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1277   -1.7066   -0.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3590   -0.0632   -1.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2425   -1.0528    1.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4443    0.7121    1.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0922   -1.0942    0.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2655    0.3191    1.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7156    1.8537   -0.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5890    0.6210   -1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1641    0.1714   -0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9027    3.0719   -0.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5879    2.8366    0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4377    3.1889   -1.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5175    0.8416   -1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6862    0.3754    0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7487    1.6637    0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6158    2.0397   -1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6847   -0.3418   -2.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7276   -0.7911   -0.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9225    0.6063   -0.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7941    0.8354   -1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7667   -1.5453   -2.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9872   -1.9324   -0.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8692   -0.2091   -2.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1367   -1.9487   -1.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1825   -0.2572   -0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4961    1.0271    1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1187    0.4263    1.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2622   -0.3357    3.6858 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  2  3
 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  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  0
 17 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 24 61  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
MK 0518	ChEBI
MK-0518	ChEBI
MK0518	ChEBI
Raltegravirum	ChEBI
Isentress	MeSH, HMDB
Potassium, raltegravir	MeSH, HMDB
Raltegravir potassium	MeSH, HMDB
N-[(4-Fluorophenyl)methyl]-5-hydroxy-1-methyl-2-{2-[(5-methyl-1,3,4-oxadiazol-2-yl)formamido]propan-2-yl}-6-oxo-1,6-dihydropyrimidine-4-carboximidate	Generator, HMDB

Chemical Formula

C₂₀H₃₇NO₃

Average Molecular Weight

339.52

Monoisotopic Molecular Weight

339.277344055

IUPAC Name

N-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-{2-[(5-methyl-1,3,4-oxadiazol-2-yl)formamido]propan-2-yl}-6-oxo-1,6-dihydropyrimidine-4-carboxamide

Traditional Name

raltegravir

CAS Registry Number

Not Available

SMILES

CCCCCCCCC=CCCCCCCCC(=O)NCC(O)=O

InChI Identifier

InChI=1S/C20H37NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(22)21-18-20(23)24/h9-10H,2-8,11-18H2,1H3,(H,21,22)(H,23,24)

InChI Key

HPFXACZRFJDURI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidinecarboxylic acids and derivatives. Pyrimidinecarboxylic acids and derivatives are compounds containing a pyrimidine ring which bears a carboxylic acid group (or a derivative thereof).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Pyrimidinecarboxylic acids and derivatives

Alternative Parents

Substituents

Pyrimidine-6-carboxylic acid or derivatives
2-heteroaryl carboxamide
Fluorobenzene
Hydroxypyrimidine
Halobenzene
Pyrimidone
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Hydropyrimidine
Benzenoid
1,3,4-oxadiazole
Azole
Heteroaromatic compound
Oxadiazole
Vinylogous acid
Lactam
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Oxacycle
Azacycle
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:82960 )
pyrimidines (CHEBI:82960 )
1,2,4-oxadiazole (CHEBI:82960 )
dicarboxylic acid amide (CHEBI:82960 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0257100)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.39	ChemAxon
pKa (Strongest Acidic)	5.62	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	150.02 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.59 m³·mol⁻¹	ChemAxon
Polarizability	42.47 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	188.723	30932474
DeepCCS	[M-H]-	185.307	30932474
DeepCCS	[M-2H]-	220.781	30932474
DeepCCS	[M+Na]+	197.072	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Oleoyl Glycine	CCCCCCCCC=CCCCCCCCC(=O)NCC(O)=O	3608.7	Standard polar	33892256
N-Oleoyl Glycine	CCCCCCCCC=CCCCCCCCC(=O)NCC(O)=O	2496.6	Standard non polar	33892256
N-Oleoyl Glycine	CCCCCCCCC=CCCCCCCCC(=O)NCC(O)=O	2730.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Oleoyl Glycine,2TMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	2763.7	Semi standard non polar	33892256
N-Oleoyl Glycine,2TMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	2771.8	Standard non polar	33892256
N-Oleoyl Glycine,2TMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	2823.7	Standard polar	33892256
N-Oleoyl Glycine,2TBDMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3241.3	Semi standard non polar	33892256
N-Oleoyl Glycine,2TBDMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3099.9	Standard non polar	33892256
N-Oleoyl Glycine,2TBDMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3009.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Raltegravir GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-5901100000-402e9e529e248f508e9f	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Raltegravir GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Raltegravir GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Raltegravir GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Raltegravir GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Raltegravir GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Raltegravir GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Raltegravir GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Raltegravir GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Oleoyl Glycine LC-ESI-qTof , Positive-QTOF	splash10-014i-0011900000-1f750fd89ed368c2519a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Oleoyl Glycine , positive-QTOF	splash10-01ot-0417900000-7f0f52f17ac409473482	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Oleoyl Glycine , positive-QTOF	splash10-014i-0011900000-1f750fd89ed368c2519a	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Oleoyl Glycine 10V, Positive-QTOF	splash10-0101-0901400000-9b8042c6c461dd4fad72	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Oleoyl Glycine 20V, Positive-QTOF	splash10-00di-0900000000-f00a70c9dfa901d921ac	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Oleoyl Glycine 40V, Positive-QTOF	splash10-05fr-5900000000-465f856a37914d77e3fb	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Oleoyl Glycine 10V, Negative-QTOF	splash10-0udi-6006900000-c7ca4f296a13a927013c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Oleoyl Glycine 20V, Negative-QTOF	splash10-0ac3-2449300000-ac0de1977dc124fe404d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Oleoyl Glycine 40V, Negative-QTOF	splash10-00c3-7694000000-1866c94f65b8fe9ccb57	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Oleoyl Glycine 10V, Positive-QTOF	splash10-002f-6009000000-d1f29a25fb262468cda8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Oleoyl Glycine 20V, Positive-QTOF	splash10-004i-9121000000-3bd27eb556983ed36c17	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Oleoyl Glycine 40V, Positive-QTOF	splash10-0a6u-9100000000-e5ee0f1c1ddd84c6fe41	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Oleoyl Glycine 10V, Negative-QTOF	splash10-000i-1009000000-30c3a690fbd89dd9372b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Oleoyl Glycine 20V, Negative-QTOF	splash10-00di-9002000000-7b142c09660037254c26	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Oleoyl Glycine 40V, Negative-QTOF	splash10-00di-9000000000-25e5315d765107a9843a	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

DB06817

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

16445111

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Raltegravir

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

82960

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-Oleoyl Glycine (HMDB0241916)

MOL for HMDB0241916 (N-Oleoyl Glycine)

3D MOL for HMDB0241916 (N-Oleoyl Glycine)

3D SDF for HMDB0241916 (N-Oleoyl Glycine)

3D-SDF for HMDB0241916 (N-Oleoyl Glycine)

PDB for HMDB0241916 (N-Oleoyl Glycine)

3D PDB for HMDB0241916 (N-Oleoyl Glycine)

SMILES for HMDB0241916 (N-Oleoyl Glycine)

INCHI for HMDB0241916 (N-Oleoyl Glycine)

Structure for HMDB0241916 (N-Oleoyl Glycine)

3D Structure for HMDB0241916 (N-Oleoyl Glycine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra