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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-10-25 14:19:28 UTC

Update Date

2020-02-26 21:25:45 UTC

HMDB ID

HMDB0005096

Secondary Accession Numbers

HMDB0062617
HMDB05096
HMDB62617

Metabolite Identification

Common Name

N-Arachidonoylglycine

Description

N-Arachidonoylglycine, also known as nagly or ema-1 20:4, 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. Thus, N-arachidonoylglycine is considered to be a fatty amide lipid molecule. N-Arachidonoylglycine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

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

  Mrv1652304202019332D          

 26 25  0  0  0  0            999 V2000
10003.187410006.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.471910006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.758510006.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.043210006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.327710006.8454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.614310006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.896810006.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.183510006.4334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.896810007.6707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.043210005.6088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.902810006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.727510006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.440910006.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.156310006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.981610006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.696210006.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.411110006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.236110006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.950810006.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.665610006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.490710006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.205310006.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.920010006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.634710006.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.351310006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.066010006.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

HMDB0005096
     RDKit          3D
N-Arachidonoylglycine
 61 60  0  0  0  0  0  0  0  0999 V2000
   -7.8165    0.1874   -4.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3448    0.3709   -2.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7682   -0.9120   -2.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2760   -0.8908   -0.8145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1592    0.1285   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9975   -0.1276   -1.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7733   -0.4119   -1.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2025   -0.5639    0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9953   -0.4591    1.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9083    0.3972    2.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8801    1.4719    2.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0367    1.2570    3.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2397    1.0307    3.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0659    0.9523    2.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7316   -0.3438    2.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0368   -0.4637    2.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0086    0.6176    2.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8774    0.7397    1.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6495   -0.5245    0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4848   -0.3846   -0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4668    0.6792   -1.0786 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3049   -1.4452   -0.8452 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1538   -1.3712   -2.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1079   -0.2579   -1.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0830    0.4260   -0.7894 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0417    0.0438   -2.8107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9370   -0.0486   -4.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5138   -0.6638   -4.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2814    1.1352   -4.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2360    0.6990   -2.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5376    1.1339   -2.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5932   -1.6819   -2.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9707   -1.3119   -2.8726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9393   -1.9021   -0.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1431   -0.6577   -0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6193    1.1050   -0.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0548    0.2893    0.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2175   -0.0662   -2.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0720   -0.5576   -1.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6862   -1.6183    0.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2655    0.0691    0.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7865   -1.2574    1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6137    0.3263    3.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4575    2.4265    2.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3679    1.5915    1.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5481    1.2931    4.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7566    0.8862    4.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4514    1.2151    1.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8529    1.7629    2.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1139   -1.2292    2.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4297   -1.4928    2.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6973    1.6044    2.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7494    0.3043    3.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6099    1.5599    1.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2736    0.9564    0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9716   -1.4025    0.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2907   -0.6837    1.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3168   -2.3279   -0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7070   -2.3030   -2.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5000   -1.1793   -2.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0262    0.1359   -2.6057 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  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 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
 22 58  1  0
 23 59  1  0
 23 60  1  0
 26 61  1  0
M  END

  Mrv1652304202019332D          

 26 25  0  0  0  0            999 V2000
10003.187410006.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.471910006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.758510006.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.043210006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.327710006.8454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.614310006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.896810006.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.183510006.4334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.896810007.6707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.043210005.6088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.902810006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.727510006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.440910006.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.156310006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.981610006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.696210006.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.411110006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.236110006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.950810006.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.665610006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.490710006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.205310006.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.920010006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.634710006.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.351310006.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.066010006.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005096

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=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)/b7-6-,10-9-,13-12-,16-15-

> <INCHI_KEY>
YLEARPUNMCCKMP-DOFZRALJSA-N

> <FORMULA>
C22H35NO3

> <MOLECULAR_WEIGHT>
361.5182

> <EXACT_MASS>
361.261693991

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
42.857996564144266

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenamido]acetic acid

> <ALOGPS_LOGP>
6.28

> <JCHEM_LOGP>
5.481887571333334

> <ALOGPS_LOGS>
-6.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.89504496242905

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9841536053570614

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6855981479637538

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
112.75750000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.61e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nagly

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005096
     RDKit          3D
N-Arachidonoylglycine
 61 60  0  0  0  0  0  0  0  0999 V2000
   -7.8165    0.1874   -4.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3448    0.3709   -2.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7682   -0.9120   -2.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2760   -0.8908   -0.8145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1592    0.1285   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9975   -0.1276   -1.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7733   -0.4119   -1.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2025   -0.5639    0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9953   -0.4591    1.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9083    0.3972    2.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8801    1.4719    2.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0367    1.2570    3.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2397    1.0307    3.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0659    0.9523    2.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7316   -0.3438    2.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0368   -0.4637    2.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0086    0.6176    2.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8774    0.7397    1.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6495   -0.5245    0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4848   -0.3846   -0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4668    0.6792   -1.0786 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3049   -1.4452   -0.8452 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1538   -1.3712   -2.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1079   -0.2579   -1.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0830    0.4260   -0.7894 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0417    0.0438   -2.8107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9370   -0.0486   -4.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5138   -0.6638   -4.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2814    1.1352   -4.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2360    0.6990   -2.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5376    1.1339   -2.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5932   -1.6819   -2.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9707   -1.3119   -2.8726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9393   -1.9021   -0.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1431   -0.6577   -0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6193    1.1050   -0.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0548    0.2893    0.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2175   -0.0662   -2.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0720   -0.5576   -1.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6862   -1.6183    0.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2655    0.0691    0.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7865   -1.2574    1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6137    0.3263    3.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4575    2.4265    2.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3679    1.5915    1.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5481    1.2931    4.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7566    0.8862    4.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4514    1.2151    1.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8529    1.7629    2.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1139   -1.2292    2.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4297   -1.4928    2.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6973    1.6044    2.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7494    0.3043    3.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6099    1.5599    1.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2736    0.9564    0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9716   -1.4025    0.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2907   -0.6837    1.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3168   -2.3279   -0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7070   -2.3030   -2.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5000   -1.1793   -2.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0262    0.1359   -2.6057 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  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 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
 22 58  1  0
 23 59  1  0
 23 60  1  0
 26 61  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0    8672.6168679.445   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8671.2818678.676   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8669.9498679.445   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8668.6148678.676   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8667.2788679.445   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8665.9478678.676   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8664.6078679.445   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8663.2768678.676   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8664.6078680.985   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8668.6148677.136   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8673.9528678.676   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8675.4918678.676   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8676.8238679.445   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8678.1588678.676   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8679.6998678.676   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8681.0338679.445   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8682.3678678.676   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8683.9078678.676   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8685.2418679.445   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8686.5768678.676   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8688.1168678.676   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8689.4508679.445   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8690.7848678.676   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8692.1188679.445   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8693.4568678.676   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8694.7908679.445   0.000  0.00  0.00           C+0
CONECT    1    2   11                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    4                                                            
CONECT   11    1   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

COMPND    HMDB0005096
HETATM    1  C1  UNL     1      -7.816   0.187  -4.176  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.345   0.371  -2.724  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.768  -0.912  -2.218  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.276  -0.891  -0.815  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.159   0.128  -0.572  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.998  -0.128  -1.408  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.773  -0.412  -1.107  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.203  -0.564   0.203  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.995  -0.459   1.402  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.908   0.397   2.378  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.880   1.472   2.365  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.037   1.257   3.570  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.240   1.031   3.593  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.066   0.952   2.382  1.00  0.00           C  
HETATM   15  C15 UNL     1       1.732  -0.344   2.216  1.00  0.00           C  
HETATM   16  C16 UNL     1       3.037  -0.464   2.163  1.00  0.00           C  
HETATM   17  C17 UNL     1       4.009   0.618   2.257  1.00  0.00           C  
HETATM   18  C18 UNL     1       4.877   0.740   1.012  1.00  0.00           C  
HETATM   19  C19 UNL     1       5.650  -0.525   0.780  1.00  0.00           C  
HETATM   20  C20 UNL     1       6.485  -0.385  -0.425  1.00  0.00           C  
HETATM   21  O1  UNL     1       6.467   0.679  -1.079  1.00  0.00           O  
HETATM   22  N1  UNL     1       7.305  -1.445  -0.845  1.00  0.00           N  
HETATM   23  C21 UNL     1       8.154  -1.371  -2.027  1.00  0.00           C  
HETATM   24  C22 UNL     1       9.108  -0.258  -1.836  1.00  0.00           C  
HETATM   25  O2  UNL     1       9.083   0.426  -0.789  1.00  0.00           O  
HETATM   26  O3  UNL     1      10.042   0.044  -2.811  1.00  0.00           O  
HETATM   27  H1  UNL     1      -6.937  -0.049  -4.806  1.00  0.00           H  
HETATM   28  H2  UNL     1      -8.514  -0.664  -4.209  1.00  0.00           H  
HETATM   29  H3  UNL     1      -8.281   1.135  -4.526  1.00  0.00           H  
HETATM   30  H4  UNL     1      -8.236   0.699  -2.157  1.00  0.00           H  
HETATM   31  H5  UNL     1      -6.538   1.134  -2.771  1.00  0.00           H  
HETATM   32  H6  UNL     1      -7.593  -1.682  -2.248  1.00  0.00           H  
HETATM   33  H7  UNL     1      -5.971  -1.312  -2.873  1.00  0.00           H  
HETATM   34  H8  UNL     1      -5.939  -1.902  -0.542  1.00  0.00           H  
HETATM   35  H9  UNL     1      -7.143  -0.658  -0.154  1.00  0.00           H  
HETATM   36  H10 UNL     1      -5.619   1.105  -0.993  1.00  0.00           H  
HETATM   37  H11 UNL     1      -5.055   0.289   0.480  1.00  0.00           H  
HETATM   38  H12 UNL     1      -4.217  -0.066  -2.514  1.00  0.00           H  
HETATM   39  H13 UNL     1      -2.072  -0.558  -1.966  1.00  0.00           H  
HETATM   40  H14 UNL     1      -1.686  -1.618   0.163  1.00  0.00           H  
HETATM   41  H15 UNL     1      -1.266   0.069   0.329  1.00  0.00           H  
HETATM   42  H16 UNL     1      -3.786  -1.257   1.522  1.00  0.00           H  
HETATM   43  H17 UNL     1      -3.614   0.326   3.238  1.00  0.00           H  
HETATM   44  H18 UNL     1      -2.458   2.427   2.636  1.00  0.00           H  
HETATM   45  H19 UNL     1      -1.368   1.592   1.439  1.00  0.00           H  
HETATM   46  H20 UNL     1      -1.548   1.293   4.545  1.00  0.00           H  
HETATM   47  H21 UNL     1       0.757   0.886   4.557  1.00  0.00           H  
HETATM   48  H22 UNL     1       0.451   1.215   1.501  1.00  0.00           H  
HETATM   49  H23 UNL     1       1.853   1.763   2.402  1.00  0.00           H  
HETATM   50  H24 UNL     1       1.114  -1.229   2.135  1.00  0.00           H  
HETATM   51  H25 UNL     1       3.430  -1.493   2.037  1.00  0.00           H  
HETATM   52  H26 UNL     1       3.697   1.604   2.530  1.00  0.00           H  
HETATM   53  H27 UNL     1       4.749   0.304   3.076  1.00  0.00           H  
HETATM   54  H28 UNL     1       5.610   1.560   1.154  1.00  0.00           H  
HETATM   55  H29 UNL     1       4.274   0.956   0.113  1.00  0.00           H  
HETATM   56  H30 UNL     1       4.972  -1.402   0.730  1.00  0.00           H  
HETATM   57  H31 UNL     1       6.291  -0.684   1.680  1.00  0.00           H  
HETATM   58  H32 UNL     1       7.317  -2.328  -0.299  1.00  0.00           H  
HETATM   59  H33 UNL     1       8.707  -2.303  -2.183  1.00  0.00           H  
HETATM   60  H34 UNL     1       7.500  -1.179  -2.910  1.00  0.00           H  
HETATM   61  H35 UNL     1      11.026   0.136  -2.606  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   21   22
CONECT   22   23   58
CONECT   23   24   59   60
CONECT   24   25   25   26
CONECT   26   61
END

HMDB0005096
     RDKit          3D
N-Arachidonoylglycine
 61 60  0  0  0  0  0  0  0  0999 V2000
   -7.8165    0.1874   -4.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3448    0.3709   -2.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7682   -0.9120   -2.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2760   -0.8908   -0.8145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1592    0.1285   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9975   -0.1276   -1.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7733   -0.4119   -1.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2025   -0.5639    0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9953   -0.4591    1.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9083    0.3972    2.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8801    1.4719    2.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0367    1.2570    3.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2397    1.0307    3.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0659    0.9523    2.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7316   -0.3438    2.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0368   -0.4637    2.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0086    0.6176    2.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8774    0.7397    1.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6495   -0.5245    0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4848   -0.3846   -0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4668    0.6792   -1.0786 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3049   -1.4452   -0.8452 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1538   -1.3712   -2.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1079   -0.2579   -1.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0830    0.4260   -0.7894 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0417    0.0438   -2.8107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9370   -0.0486   -4.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5138   -0.6638   -4.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2814    1.1352   -4.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2360    0.6990   -2.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5376    1.1339   -2.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5932   -1.6819   -2.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9707   -1.3119   -2.8726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9393   -1.9021   -0.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1431   -0.6577   -0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6193    1.1050   -0.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0548    0.2893    0.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2175   -0.0662   -2.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0720   -0.5576   -1.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6862   -1.6183    0.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2655    0.0691    0.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7865   -1.2574    1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6137    0.3263    3.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4575    2.4265    2.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3679    1.5915    1.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5481    1.2931    4.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7566    0.8862    4.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4514    1.2151    1.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8529    1.7629    2.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1139   -1.2292    2.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4297   -1.4928    2.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6973    1.6044    2.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7494    0.3043    3.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6099    1.5599    1.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2736    0.9564    0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9716   -1.4025    0.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2907   -0.6837    1.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3168   -2.3279   -0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7070   -2.3030   -2.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5000   -1.1793   -2.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0262    0.1359   -2.6057 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  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 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
 22 58  1  0
 23 59  1  0
 23 60  1  0
 26 61  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-glycine	ChEBI
N-Arachidonoyl glycine	ChEBI
NAGly	ChEBI
N-Arachidonyl-L-glycine	HMDB
N-Arachidonylglycine	HMDB
EMA-1 20:4	HMDB
NAGly amino acid	HMDB
N-Arachidonoyl glycinate	HMDB
N-Arachidonoylglycinate	HMDB
N-[(5Z,8Z,11Z,14Z)-1-oxo-5,8,11,14-Eicosatetraen-1-yl]glycine	HMDB
N-Arachidonoylglycine	HMDB

Chemical Formula

C₂₂H₃₅NO₃

Average Molecular Weight

361.5182

Monoisotopic Molecular Weight

361.261693991

IUPAC Name

2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenamido]acetic acid

Traditional Name

nagly

CAS Registry Number

179113-91-8

SMILES

CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=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)/b7-6-,10-9-,13-12-,16-15-

InChI Key

YLEARPUNMCCKMP-DOFZRALJSA-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

Substituents

N-acyl-alpha-amino acid
Fatty amide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

fatty amide (CHEBI:58961 )
N-acylglycine (CHEBI:58961 )
N-acyl amines (LMFA08020003 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)

Cellular substructure

Membrane (HMDB: HMDB0005096)

Source

Endogenous

Endogenous (HMDB: HMDB0005096)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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	4.043	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00036 g/L	ALOGPS
logP	6.28	ALOGPS
logP	5.48	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	3.98	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	112.76 m³·mol⁻¹	ChemAxon
Polarizability	42.86 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	199.191	31661259
DarkChem	[M-H]-	198.061	31661259
DeepCCS	[M+H]+	199.415	30932474
DeepCCS	[M+H]+	191.256	30932474
DeepCCS	[M-H]-	197.057	30932474
DeepCCS	[M-H]-	188.898	30932474
DeepCCS	[M-2H]-	229.943	30932474
DeepCCS	[M+Na]+	205.508	30932474
DeepCCS	[M-2H]-	221.785	30932474
DeepCCS	[M+Na]+	197.35	30932474
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]-	194.1	32859911
AllCCS	[M+Na-2H]-	196.3	32859911
AllCCS	[M+HCOO]-	198.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Arachidonoylglycine	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCC(O)=O	4026.9	Standard polar	33892256
N-Arachidonoylglycine	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCC(O)=O	2437.7	Standard non polar	33892256
N-Arachidonoylglycine	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCC(O)=O	2925.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Arachidonoylglycine,1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCC(=O)O[Si](C)(C)C	2879.8	Semi standard non polar	33892256
N-Arachidonoylglycine,1TMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CC(=O)O)[Si](C)(C)C	2971.1	Semi standard non polar	33892256
N-Arachidonoylglycine,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	2896.2	Semi standard non polar	33892256
N-Arachidonoylglycine,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	2932.7	Standard non polar	33892256
N-Arachidonoylglycine,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	3036.3	Standard polar	33892256
N-Arachidonoylglycine,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C	3142.4	Semi standard non polar	33892256
N-Arachidonoylglycine,1TBDMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C	3213.4	Semi standard non polar	33892256
N-Arachidonoylglycine,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3392.8	Semi standard non polar	33892256
N-Arachidonoylglycine,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3282.6	Standard non polar	33892256
N-Arachidonoylglycine,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3079.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Arachidonoylglycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fyc-7393000000-04b6b96f91829d5feefe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Arachidonoylglycine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9141100000-d5de221d0748b6c07322	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Arachidonoylglycine 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-Arachidonoylglycine 10V, Positive-QTOF	splash10-0229-9015000000-2860195ca439964f027c	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Arachidonoylglycine 20V, Positive-QTOF	splash10-00di-9011000000-6f824b09e6808edc4685	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Arachidonoylglycine 40V, Positive-QTOF	splash10-00di-9010000000-6846d3f3704692ffd2ca	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Arachidonoylglycine 10V, Negative-QTOF	splash10-03di-0019000000-c766b47b569374526032	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Arachidonoylglycine 20V, Negative-QTOF	splash10-03k9-4139000000-6be001e2e3c064731d71	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Arachidonoylglycine 40V, Negative-QTOF	splash10-05fu-9120000000-24a924229e7f342b295f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Arachidonoylglycine 10V, Positive-QTOF	splash10-03fr-6119000000-3e536a637c2f6c3b9ffc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Arachidonoylglycine 20V, Positive-QTOF	splash10-004i-9221000000-51b37d44e7dae3812d5a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Arachidonoylglycine 40V, Positive-QTOF	splash10-05qc-9600000000-87a70dd054c2e35516e9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Arachidonoylglycine 10V, Negative-QTOF	splash10-03di-1009000000-ad572766b9cd41e2eda2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Arachidonoylglycine 20V, Negative-QTOF	splash10-00di-9002000000-58daec3d933739b930af	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Arachidonoylglycine 40V, Negative-QTOF	splash10-00di-9000000000-77d408cf5bc92e1b44fd	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.09 +/- 0.73 uM	Adult (>18 years old)	Both	Normal	21359215	details

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

4446510

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

N-Arachidonylglycine

METLIN ID

Not Available

PubChem Compound

5283389

PDB ID

Not Available

ChEBI ID

58961

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

Lipid Maps (LMFA08020003) [Link]

Enzymes

Enzyme Details

1. Glycine N-acyltransferase

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:: GLYAT
Uniprot ID:: Q6IB77
Molecular weight:: 18506.33

Enzyme Details

2. Glycine N-acyltransferase-like protein 1

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:: GLYATL1
Uniprot ID:: Q969I3
Molecular weight:: 35100.895

Enzyme Details

3. Glycine N-acyltransferase-like protein 2

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:: GLYATL2
Uniprot ID:: Q8WU03
Molecular weight:: 34277.055

Showing metabocard for N-Arachidonoylglycine (HMDB0005096)

MOL for HMDB0005096 (N-Arachidonoylglycine)

3D MOL for HMDB0005096 (N-Arachidonoylglycine)

3D SDF for HMDB0005096 (N-Arachidonoylglycine)

3D-SDF for HMDB0005096 (N-Arachidonoylglycine)

PDB for HMDB0005096 (N-Arachidonoylglycine)

3D PDB for HMDB0005096 (N-Arachidonoylglycine)

SMILES for HMDB0005096 (N-Arachidonoylglycine)

INCHI for HMDB0005096 (N-Arachidonoylglycine)

Structure for HMDB0005096 (N-Arachidonoylglycine)

3D Structure for HMDB0005096 (N-Arachidonoylglycine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes