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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-07-27 21:22:31 UTC

Update Date

2021-09-16 22:46:33 UTC

HMDB ID

HMDB0241918

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Arachidonoyl Glycine

Description

N-arachidonoyl glycine 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 Arachidonic 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-Arachidonoyl 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-Arachidonoyl 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


  Mrv1652308272120412D          

 30 31  0  0  1  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   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
    2.1434    2.0625    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
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000    5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    6.6000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  1  1  0  0  0  0
  7  3  1  0  0  0  0
  7  5  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  2  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 13 14  1  1  0  0  0
 15 12  1  0  0  0  0
 16  6  2  0  0  0  0
 16  7  1  4  0  0  0
 17  6  1  0  0  0  0
 10 18  1  6  0  0  0
 11 19  1  1  0  0  0
 12 20  1  1  0  0  0
 21 14  2  0  0  0  0
 22 14  1  0  0  0  0
 23  2  1  0  0  0  0
 23  9  1  0  0  0  0
 24  8  1  0  0  0  0
 15 24  1  6  0  0  0
 25 13  1  0  0  0  0
 25 15  1  0  0  0  0
 10 26  1  1  0  0  0
 11 27  1  6  0  0  0
 12 28  1  6  0  0  0
 13 29  1  1  0  0  0
 15 30  1  1  0  0  0
M  END

HMDB0241918
     RDKit          3D
N-Arachidonoyl Glycine
 61 60  0  0  0  0  0  0  0  0999 V2000
   -7.5077    4.2871    0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8849    3.4593   -0.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7537    2.6352   -0.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2181    1.6828    0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9663    0.9322    1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2484   -0.0377    2.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0592   -1.3022    2.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5279   -2.0317    1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2823   -2.7217    1.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1497   -2.4456    0.9976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8810   -3.1463    1.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3360   -3.8678    0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393   -3.6643   -0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8703   -2.6823    0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1156   -1.7597   -0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2287   -1.5583   -1.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5083   -2.1986   -1.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5329   -1.1341   -0.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7532   -0.1210   -1.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7781    0.8475   -1.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4758    1.5217   -0.2309 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8963    1.0521   -1.9751 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8283    1.9974   -1.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2177    3.3342   -1.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8610    4.3004   -0.8796 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9383    3.5429   -1.8442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8191    5.2863   -0.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8484    4.5055    1.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4198    3.7933    0.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4171    4.1528   -1.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6329    2.8137   -1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2261    2.0716   -0.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9926    3.3518    0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7091    2.2075    1.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9086    0.9519    0.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5702    0.4506    0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2107    1.6497    1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6650    0.3647    3.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3126   -1.9389    3.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3817   -1.4147    0.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2273   -2.8752    0.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3301   -3.4439    2.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1003   -1.7205    0.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1202   -3.8627    2.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2098   -2.3550    1.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9605   -4.6442   -0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1551   -4.2681   -1.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7889   -3.2602    0.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5666   -2.1209    1.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2145   -1.1963   -1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2314   -0.8212   -2.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9487   -2.7221   -2.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4038   -2.9271   -0.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4804   -1.6715   -0.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2200   -0.5941    0.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0461   -0.5400   -2.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7995    0.4535   -2.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5515    1.7755    0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8026    1.9998   -1.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0770    1.6046   -0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7473    4.0226   -2.7101 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  2  3
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  3
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 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
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 21 58  1  0
 23 59  1  0
 23 60  1  0
 26 61  1  0
M  END


  Mrv1652308272120412D          

 30 31  0  0  1  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   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
    2.1434    2.0625    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
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000    5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    6.6000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  1  1  0  0  0  0
  7  3  1  0  0  0  0
  7  5  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  2  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 13 14  1  1  0  0  0
 15 12  1  0  0  0  0
 16  6  2  0  0  0  0
 16  7  1  4  0  0  0
 17  6  1  0  0  0  0
 10 18  1  6  0  0  0
 11 19  1  1  0  0  0
 12 20  1  1  0  0  0
 21 14  2  0  0  0  0
 22 14  1  0  0  0  0
 23  2  1  0  0  0  0
 23  9  1  0  0  0  0
 24  8  1  0  0  0  0
 15 24  1  6  0  0  0
 25 13  1  0  0  0  0
 25 15  1  0  0  0  0
 10 26  1  1  0  0  0
 11 27  1  6  0  0  0
 12 28  1  6  0  0  0
 13 29  1  1  0  0  0
 15 30  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0241918

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(OC2=C(OC)C=C(C=C2)N=C(C)O)O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C15H19NO9/c1-6(17)16-7-3-4-8(9(5-7)23-2)24-15-12(20)10(18)11(19)13(25-15)14(21)22/h3-5,10-13,15,18-20H,1-2H3,(H,16,17)(H,21,22)/t10-,11-,12+,13-,15+/m0/s1

> <INCHI_KEY>
XLGYMPUDHJPLNR-DKBOKBLXSA-N

> <FORMULA>
C15H19NO9

> <MOLECULAR_WEIGHT>
357.315

> <EXACT_MASS>
357.105981196

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
33.97613977154006

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[(1-hydroxyethylidene)amino]-2-methoxyphenoxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
-0.92

> <JCHEM_LOGP>
-0.5834195407803919

> <ALOGPS_LOGS>
-1.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
5.099371130623775

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.955501281749684

> <JCHEM_PKA_STRONGEST_BASIC>
1.1968692268321293

> <JCHEM_POLAR_SURFACE_AREA>
158.26999999999998

> <JCHEM_REFRACTIVITY>
82.132

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.28e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[(1-hydroxyethylidene)amino]-2-methoxyphenoxy}oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0241918
     RDKit          3D
N-Arachidonoyl Glycine
 61 60  0  0  0  0  0  0  0  0999 V2000
   -7.5077    4.2871    0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8849    3.4593   -0.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7537    2.6352   -0.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2181    1.6828    0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9663    0.9322    1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2484   -0.0377    2.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0592   -1.3022    2.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5279   -2.0317    1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2823   -2.7217    1.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1497   -2.4456    0.9976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8810   -3.1463    1.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3360   -3.8678    0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393   -3.6643   -0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8703   -2.6823    0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1156   -1.7597   -0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2287   -1.5583   -1.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5083   -2.1986   -1.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5329   -1.1341   -0.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7532   -0.1210   -1.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7781    0.8475   -1.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4758    1.5217   -0.2309 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8963    1.0521   -1.9751 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8283    1.9974   -1.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2177    3.3342   -1.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8610    4.3004   -0.8796 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9383    3.5429   -1.8442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8191    5.2863   -0.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8484    4.5055    1.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4198    3.7933    0.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4171    4.1528   -1.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6329    2.8137   -1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2261    2.0716   -0.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9926    3.3518    0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7091    2.2075    1.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9086    0.9519    0.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5702    0.4506    0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2107    1.6497    1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6650    0.3647    3.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3126   -1.9389    3.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3817   -1.4147    0.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2273   -2.8752    0.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3301   -3.4439    2.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1003   -1.7205    0.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1202   -3.8627    2.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2098   -2.3550    1.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9605   -4.6442   -0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1551   -4.2681   -1.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7889   -3.2602    0.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5666   -2.1209    1.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2145   -1.1963   -1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2314   -0.8212   -2.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9487   -2.7221   -2.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4038   -2.9271   -0.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4804   -1.6715   -0.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2200   -0.5941    0.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0461   -0.5400   -2.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7995    0.4535   -2.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5515    1.7755    0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8026    1.9998   -1.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0770    1.6046   -0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7473    4.0226   -2.7101 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  2  3
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  3
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 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
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 21 58  1  0
 23 59  1  0
 23 60  1  0
 26 61  1  0
M  END

HEADER    PROTEIN                                 27-AUG-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-AUG-21         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.000  10.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.000   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334  13.090   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334  11.550   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001  11.550   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.667   9.240   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.334   8.470   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0      -0.000  12.320   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.334  10.010   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.001  10.010   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.334  10.010   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.667   7.700   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   23                                                            
CONECT    3    4    7                                                       
CONECT    4    3    8                                                       
CONECT    5    7    9                                                       
CONECT    6    1   16   17                                                  
CONECT    7    3    5   16                                                  
CONECT    8    4    9   24                                                  
CONECT    9    5    8   23                                                  
CONECT   10   11   12   18   26                                             
CONECT   11   10   13   19   27                                             
CONECT   12   10   15   20   28                                             
CONECT   13   11   14   25   29                                             
CONECT   14   13   21   22                                                  
CONECT   15   12   24   25   30                                             
CONECT   16    6    7                                                       
CONECT   17    6                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   14                                                            
CONECT   22   14                                                            
CONECT   23    2    9                                                       
CONECT   24    8   15                                                       
CONECT   25   13   15                                                       
CONECT   26   10                                                            
CONECT   27   11                                                            
CONECT   28   12                                                            
CONECT   29   13                                                            
CONECT   30   15                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

COMPND    HMDB0241918
HETATM    1  C1  UNL     1      -7.508   4.287   0.313  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.885   3.459  -0.761  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.754   2.635  -0.210  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.218   1.683   0.886  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.966   0.932   1.321  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.248  -0.038   2.382  1.00  0.00           C  
HETATM    7  C7  UNL     1      -5.059  -1.302   2.308  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.528  -2.032   1.156  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.282  -2.722   1.584  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.150  -2.446   0.998  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.881  -3.146   1.430  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.336  -3.868   0.278  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.839  -3.664  -0.237  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.870  -2.682   0.213  1.00  0.00           C  
HETATM   15  C15 UNL     1       2.116  -1.760  -0.915  1.00  0.00           C  
HETATM   16  C16 UNL     1       3.229  -1.558  -1.518  1.00  0.00           C  
HETATM   17  C17 UNL     1       4.508  -2.199  -1.224  1.00  0.00           C  
HETATM   18  C18 UNL     1       5.533  -1.134  -0.835  1.00  0.00           C  
HETATM   19  C19 UNL     1       5.753  -0.121  -1.917  1.00  0.00           C  
HETATM   20  C20 UNL     1       6.778   0.848  -1.387  1.00  0.00           C  
HETATM   21  O1  UNL     1       6.476   1.522  -0.231  1.00  0.00           O  
HETATM   22  N1  UNL     1       7.896   1.052  -1.975  1.00  0.00           N  
HETATM   23  C21 UNL     1       8.828   1.997  -1.405  1.00  0.00           C  
HETATM   24  C22 UNL     1       8.218   3.334  -1.360  1.00  0.00           C  
HETATM   25  O2  UNL     1       8.861   4.300  -0.880  1.00  0.00           O  
HETATM   26  O3  UNL     1       6.938   3.543  -1.844  1.00  0.00           O  
HETATM   27  H1  UNL     1      -7.819   5.286  -0.102  1.00  0.00           H  
HETATM   28  H2  UNL     1      -6.848   4.505   1.167  1.00  0.00           H  
HETATM   29  H3  UNL     1      -8.420   3.793   0.749  1.00  0.00           H  
HETATM   30  H4  UNL     1      -6.417   4.153  -1.515  1.00  0.00           H  
HETATM   31  H5  UNL     1      -7.633   2.814  -1.269  1.00  0.00           H  
HETATM   32  H6  UNL     1      -5.226   2.072  -0.997  1.00  0.00           H  
HETATM   33  H7  UNL     1      -4.993   3.352   0.204  1.00  0.00           H  
HETATM   34  H8  UNL     1      -6.709   2.207   1.703  1.00  0.00           H  
HETATM   35  H9  UNL     1      -6.909   0.952   0.455  1.00  0.00           H  
HETATM   36  H10 UNL     1      -4.570   0.451   0.435  1.00  0.00           H  
HETATM   37  H11 UNL     1      -4.211   1.650   1.735  1.00  0.00           H  
HETATM   38  H12 UNL     1      -5.665   0.365   3.341  1.00  0.00           H  
HETATM   39  H13 UNL     1      -5.313  -1.939   3.187  1.00  0.00           H  
HETATM   40  H14 UNL     1      -4.382  -1.415   0.277  1.00  0.00           H  
HETATM   41  H15 UNL     1      -5.227  -2.875   0.859  1.00  0.00           H  
HETATM   42  H16 UNL     1      -3.330  -3.444   2.377  1.00  0.00           H  
HETATM   43  H17 UNL     1      -2.100  -1.720   0.205  1.00  0.00           H  
HETATM   44  H18 UNL     1      -1.120  -3.863   2.257  1.00  0.00           H  
HETATM   45  H19 UNL     1      -0.210  -2.355   1.771  1.00  0.00           H  
HETATM   46  H20 UNL     1      -0.961  -4.644  -0.196  1.00  0.00           H  
HETATM   47  H21 UNL     1       1.155  -4.268  -1.110  1.00  0.00           H  
HETATM   48  H22 UNL     1       2.789  -3.260   0.522  1.00  0.00           H  
HETATM   49  H23 UNL     1       1.567  -2.121   1.129  1.00  0.00           H  
HETATM   50  H24 UNL     1       1.215  -1.196  -1.249  1.00  0.00           H  
HETATM   51  H25 UNL     1       3.231  -0.821  -2.355  1.00  0.00           H  
HETATM   52  H26 UNL     1       4.949  -2.722  -2.114  1.00  0.00           H  
HETATM   53  H27 UNL     1       4.404  -2.927  -0.410  1.00  0.00           H  
HETATM   54  H28 UNL     1       6.480  -1.671  -0.641  1.00  0.00           H  
HETATM   55  H29 UNL     1       5.220  -0.594   0.082  1.00  0.00           H  
HETATM   56  H30 UNL     1       6.046  -0.540  -2.889  1.00  0.00           H  
HETATM   57  H31 UNL     1       4.800   0.453  -2.099  1.00  0.00           H  
HETATM   58  H32 UNL     1       5.551   1.775   0.074  1.00  0.00           H  
HETATM   59  H33 UNL     1       9.803   2.000  -1.944  1.00  0.00           H  
HETATM   60  H34 UNL     1       9.077   1.605  -0.377  1.00  0.00           H  
HETATM   61  H35 UNL     1       6.747   4.023  -2.710  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   30   31
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6   36   37
CONECT    6    7    7   38
CONECT    7    8   39
CONECT    8    9   40   41
CONECT    9   10   10   42
CONECT   10   11   43
CONECT   11   12   44   45
CONECT   12   13   13   46
CONECT   13   14   47
CONECT   14   15   48   49
CONECT   15   16   16   50
CONECT   16   17   51
CONECT   17   18   52   53
CONECT   18   19   54   55
CONECT   19   20   56   57
CONECT   20   21   22   22
CONECT   21   58
CONECT   22   23
CONECT   23   24   59   60
CONECT   24   25   25   26
CONECT   26   61
END

HMDB0241918
     RDKit          3D
N-Arachidonoyl Glycine
 61 60  0  0  0  0  0  0  0  0999 V2000
   -7.5077    4.2871    0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8849    3.4593   -0.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7537    2.6352   -0.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2181    1.6828    0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9663    0.9322    1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2484   -0.0377    2.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0592   -1.3022    2.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5279   -2.0317    1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2823   -2.7217    1.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1497   -2.4456    0.9976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8810   -3.1463    1.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3360   -3.8678    0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393   -3.6643   -0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8703   -2.6823    0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1156   -1.7597   -0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2287   -1.5583   -1.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5083   -2.1986   -1.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5329   -1.1341   -0.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7532   -0.1210   -1.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7781    0.8475   -1.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4758    1.5217   -0.2309 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8963    1.0521   -1.9751 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8283    1.9974   -1.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2177    3.3342   -1.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8610    4.3004   -0.8796 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9383    3.5429   -1.8442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8191    5.2863   -0.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8484    4.5055    1.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4198    3.7933    0.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4171    4.1528   -1.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6329    2.8137   -1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2261    2.0716   -0.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9926    3.3518    0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7091    2.2075    1.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9086    0.9519    0.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5702    0.4506    0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2107    1.6497    1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6650    0.3647    3.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3126   -1.9389    3.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3817   -1.4147    0.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2273   -2.8752    0.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3301   -3.4439    2.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1003   -1.7205    0.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1202   -3.8627    2.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2098   -2.3550    1.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9605   -4.6442   -0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1551   -4.2681   -1.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7889   -3.2602    0.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5666   -2.1209    1.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2145   -1.1963   -1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2314   -0.8212   -2.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9487   -2.7221   -2.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4038   -2.9271   -0.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4804   -1.6715   -0.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2200   -0.5941    0.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0461   -0.5400   -2.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7995    0.4535   -2.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5515    1.7755    0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8026    1.9998   -1.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0770    1.6046   -0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7473    4.0226   -2.7101 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  2  3
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  3
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 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
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 21 58  1  0
 23 59  1  0
 23 60  1  0
 26 61  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₂H₃₅NO₃

Average Molecular Weight

361.5182

Monoisotopic Molecular Weight

361.261693991

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[(1-hydroxyethylidene)amino]-2-methoxyphenoxy}oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[(1-hydroxyethylidene)amino]-2-methoxyphenoxy}oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCCCCC=CCC=CCC=CCC=CCCCC(O)=NCC(O)=O

InChI Identifier

InChI=1S/C22H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21(24)23-20-22(25)26/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-20H2,1H3,(H,23,24)(H,25,26)

InChI Key

YLEARPUNMCCKMP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Not Available

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.92	ALOGPS
logP	-0.58	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	2.96	ChemAxon
pKa (Strongest Basic)	1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	158.27 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.13 m³·mol⁻¹	ChemAxon
Polarizability	33.98 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	196.1	32859911
AllCCS	[M+H-H2O]+	193.5	32859911
AllCCS	[M+NH4]+	198.4	32859911
AllCCS	[M+Na]+	199.1	32859911
AllCCS	[M-H]-	193.8	32859911
AllCCS	[M+Na-2H]-	196.0	32859911
AllCCS	[M+HCOO]-	198.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Arachidonoyl Glycine	CCCCCC=CCC=CCC=CCC=CCCCC(O)=NCC(O)=O	3341.6	Standard polar	33892256
N-Arachidonoyl Glycine	CCCCCC=CCC=CCC=CCC=CCCCC(O)=NCC(O)=O	2349.7	Standard non polar	33892256
N-Arachidonoyl Glycine	CCCCCC=CCC=CCC=CCC=CCCCC(O)=NCC(O)=O	2823.5	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-Arachidonoyl Glycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0v7l-6393000000-1a6b151fca51ec8d178a	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Arachidonoyl Glycine 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-Arachidonoyl Glycine 10V, Positive-QTOF	splash10-03di-1019000000-abf521c50b82d3c1c0cf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Arachidonoyl Glycine 20V, Positive-QTOF	splash10-071i-9753000000-084be478f48654cee1f6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Arachidonoyl Glycine 40V, Positive-QTOF	splash10-05o3-9800000000-7fc410a7bcd118dde147	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Arachidonoyl Glycine 10V, Negative-QTOF	splash10-03k9-3009000000-460d7a655f0d74e473de	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Arachidonoyl Glycine 20V, Negative-QTOF	splash10-00di-9035000000-80ae94fbef0702ebd88a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Arachidonoyl Glycine 40V, Negative-QTOF	splash10-05fr-9010000000-aedd082f403ce27a209f	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023629

KNApSAcK ID

Not Available

Chemspider ID

52083351

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4345

PDB ID

Not Available

ChEBI ID

92898

Food Biomarker Ontology

Not Available

VMH ID

CE2020

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-Arachidonoyl Glycine (HMDB0241918)

MOL for HMDB0241918 (N-Arachidonoyl Glycine)

3D MOL for HMDB0241918 (N-Arachidonoyl Glycine)

3D SDF for HMDB0241918 (N-Arachidonoyl Glycine)

3D-SDF for HMDB0241918 (N-Arachidonoyl Glycine)

PDB for HMDB0241918 (N-Arachidonoyl Glycine)

3D PDB for HMDB0241918 (N-Arachidonoyl Glycine)

SMILES for HMDB0241918 (N-Arachidonoyl Glycine)

INCHI for HMDB0241918 (N-Arachidonoyl Glycine)

Structure for HMDB0241918 (N-Arachidonoyl Glycine)

3D Structure for HMDB0241918 (N-Arachidonoyl Glycine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra