You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2010-05-20 12:52:41 UTC

Update Date

2022-03-07 02:51:34 UTC

HMDB ID

HMDB0013626

Secondary Accession Numbers

HMDB13626

Metabolite Identification

Common Name

Adrenoyl ethanolamide

Description

Adrenoyl ethanolamide is a N-acylethanolamine. N-acylethanolamines (NAEs) constitute a class of lipid compounds naturally present in both animal and plant membranes as constituents of the membrane-bound phospholipid, N-acylphosphatidylethanolamine (NAPE). NAPE is composed of a third fatty acid moiety linked to the amino head group of the commonly occurring membrane phospholipid, phosphatidylethanolamine. NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli. Transient NAE release and accumulation has been attributed a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. N-oleoylethanolamine is an inhibitor of the sphingolipid signaling pathway, via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). N-oleoylethanolamine blocks the effects of TNF- and arachidonic acid on intracellular Ca concentration. (PMID: 12692337 , 12056855 , 12560208 , 11997249 ).

Structure

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


  Mrv0541 02271200282D          

 27 26  0  0  0  0            999 V2000
    5.8462  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5607  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2751  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9897  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7041  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4186  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1331  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8475  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5620  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2765  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9910  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7055  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4200  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1344  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8489  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5634  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2778  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9923  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7068  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4213  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1358  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8502  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5647  -15.7529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8502  -14.5154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2792  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9936  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7081  -15.3404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 25 23  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
M  END

HMDB0013626
     RDKit          3D
Adrenoyl ethanolamide
 68 67  0  0  0  0  0  0  0  0999 V2000
    8.4388    1.8230   -0.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2930    2.4629   -1.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6073    1.5999   -2.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0224    0.3137   -1.8732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9586    0.2534   -0.8558 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2301    0.7010    0.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1621   -0.1040    1.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8147   -1.5182    1.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5857   -1.8619    2.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4674   -2.3737    1.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2972   -2.6773    0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2982   -2.0760   -0.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4113   -1.1673   -0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2594   -0.5458    1.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9326   -0.7295    1.9018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9658   -1.4507    1.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2384   -2.2973    0.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5510   -1.7630   -0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3171   -0.3450   -0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5631    0.2704   -1.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6716    0.2182   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9106    0.8209   -0.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8874    1.2749   -1.8212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0756    0.8700    0.1582 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2760    1.4479   -0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1057    2.9024   -0.7690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7354    3.6671    0.3275 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2893    1.6223   -1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1740    0.8716   -0.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8115    2.5865    0.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6103    3.0387   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8173    3.2666   -1.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2891    1.3579   -3.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7988    2.2188   -2.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6782   -0.1816   -2.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8319   -0.4150   -1.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4077   -0.7253   -0.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1290    0.9659   -1.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4865    1.7690    0.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3841    0.3302    2.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9053   -1.9044    0.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6967   -2.0442    2.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6280   -1.6599    3.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6390   -2.5893    2.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3224   -2.7242   -0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0704   -3.8299    0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2496   -2.4295   -1.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2684   -0.8000   -1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1548    0.6245    0.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1876   -0.4549    1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9221   -0.1282    2.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7597   -1.4055    2.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5540   -2.4150   -0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6029   -3.3438    0.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7878   -2.4291   -0.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2784   -1.8486    0.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9311    0.2249    0.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5336   -0.2798   -1.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3618    1.3031   -1.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8003   -0.3198   -1.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3517    0.7280    0.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9294   -0.8652    0.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0560    0.4915    1.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0737    1.3951    0.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6195    0.8469   -1.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3901    3.0453   -1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0928    3.2650   -1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8645    3.1254    1.1687 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  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 24 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
M  END


  Mrv0541 02271200282D          

 27 26  0  0  0  0            999 V2000
    5.8462  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5607  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2751  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9897  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7041  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4186  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1331  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8475  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5620  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2765  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9910  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7055  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4200  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1344  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8489  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5634  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2778  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9923  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7068  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4213  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1358  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8502  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5647  -15.7529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8502  -14.5154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2792  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9936  -15.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7081  -15.3404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 25 23  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013626

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(=O)NCCO

> <INCHI_IDENTIFIER>
InChI=1S/C24H41NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(27)25-22-23-26/h6-7,9-10,12-13,15-16,26H,2-5,8,11,14,17-23H2,1H3,(H,25,27)/b7-6-,10-9-,13-12-,16-15-

> <INCHI_KEY>
FMVHVRYFQIXOAF-DOFZRALJSA-N

> <FORMULA>
C24H41NO2

> <MOLECULAR_WEIGHT>
375.5878

> <EXACT_MASS>
375.313729561

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
47.16563561963316

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(7Z,10Z,13Z,16Z)-N-(2-hydroxyethyl)docosa-7,10,13,16-tetraenamide

> <ALOGPS_LOGP>
6.58

> <JCHEM_LOGP>
6.202939581000001

> <ALOGPS_LOGS>
-6.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.45421975479898

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.463455353153769

> <JCHEM_PKA_STRONGEST_BASIC>
-0.32593691026839566

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
122.16719999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.91e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
docosatetraenoylethanolamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013626
     RDKit          3D
Adrenoyl ethanolamide
 68 67  0  0  0  0  0  0  0  0999 V2000
    8.4388    1.8230   -0.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2930    2.4629   -1.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6073    1.5999   -2.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0224    0.3137   -1.8732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9586    0.2534   -0.8558 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2301    0.7010    0.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1621   -0.1040    1.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8147   -1.5182    1.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5857   -1.8619    2.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4674   -2.3737    1.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2972   -2.6773    0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2982   -2.0760   -0.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4113   -1.1673   -0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2594   -0.5458    1.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9326   -0.7295    1.9018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9658   -1.4507    1.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2384   -2.2973    0.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5510   -1.7630   -0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3171   -0.3450   -0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5631    0.2704   -1.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6716    0.2182   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9106    0.8209   -0.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8874    1.2749   -1.8212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0756    0.8700    0.1582 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2760    1.4479   -0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1057    2.9024   -0.7690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7354    3.6671    0.3275 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2893    1.6223   -1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1740    0.8716   -0.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8115    2.5865    0.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6103    3.0387   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8173    3.2666   -1.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2891    1.3579   -3.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7988    2.2188   -2.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6782   -0.1816   -2.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8319   -0.4150   -1.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4077   -0.7253   -0.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1290    0.9659   -1.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4865    1.7690    0.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3841    0.3302    2.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9053   -1.9044    0.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6967   -2.0442    2.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6280   -1.6599    3.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6390   -2.5893    2.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3224   -2.7242   -0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0704   -3.8299    0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2496   -2.4295   -1.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2684   -0.8000   -1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1548    0.6245    0.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1876   -0.4549    1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9221   -0.1282    2.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7597   -1.4055    2.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5540   -2.4150   -0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6029   -3.3438    0.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7878   -2.4291   -0.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2784   -1.8486    0.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9311    0.2249    0.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5336   -0.2798   -1.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3618    1.3031   -1.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8003   -0.3198   -1.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3517    0.7280    0.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9294   -0.8652    0.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0560    0.4915    1.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0737    1.3951    0.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6195    0.8469   -1.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3901    3.0453   -1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0928    3.2650   -1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8645    3.1254    1.1687 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  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 24 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0      10.913 -29.405   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.247 -28.635   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.580 -29.405   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.914 -28.635   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.248 -29.405   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.581 -28.635   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.915 -28.635   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.249 -29.405   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.582 -28.635   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.916 -28.635   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.250 -29.405   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.584 -28.635   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.917 -28.635   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.251 -29.405   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.585 -28.635   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.918 -28.635   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      32.252 -29.405   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      33.586 -28.635   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      34.919 -29.405   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      36.253 -28.635   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      37.587 -29.405   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      38.920 -28.635   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      40.254 -29.405   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0      38.920 -27.095   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      41.588 -28.635   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      42.921 -29.405   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      44.255 -28.635   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   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   24                                                  
CONECT   23   22   25                                                       
CONECT   24   22                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

COMPND    HMDB0013626
HETATM    1  C1  UNL     1       8.439   1.823  -0.584  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.293   2.463  -1.316  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.607   1.600  -2.298  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.022   0.314  -1.873  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.959   0.253  -0.856  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.230   0.701   0.499  1.00  0.00           C  
HETATM    7  C7  UNL     1       5.162  -0.104   1.536  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.815  -1.518   1.447  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.586  -1.862   2.206  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.467  -2.374   1.730  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.297  -2.677   0.338  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.298  -2.076  -0.494  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.411  -1.167  -0.209  1.00  0.00           C  
HETATM   14  C14 UNL     1       0.259  -0.546   1.087  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.933  -0.729   1.902  1.00  0.00           C  
HETATM   16  C16 UNL     1      -1.966  -1.451   1.677  1.00  0.00           C  
HETATM   17  C17 UNL     1      -2.238  -2.297   0.534  1.00  0.00           C  
HETATM   18  C18 UNL     1      -3.551  -1.763  -0.087  1.00  0.00           C  
HETATM   19  C19 UNL     1      -3.317  -0.345  -0.474  1.00  0.00           C  
HETATM   20  C20 UNL     1      -4.563   0.270  -1.082  1.00  0.00           C  
HETATM   21  C21 UNL     1      -5.672   0.218  -0.072  1.00  0.00           C  
HETATM   22  C22 UNL     1      -6.911   0.821  -0.638  1.00  0.00           C  
HETATM   23  O1  UNL     1      -6.887   1.275  -1.821  1.00  0.00           O  
HETATM   24  N1  UNL     1      -8.076   0.870   0.158  1.00  0.00           N  
HETATM   25  C23 UNL     1      -9.276   1.448  -0.373  1.00  0.00           C  
HETATM   26  C24 UNL     1      -9.106   2.902  -0.769  1.00  0.00           C  
HETATM   27  O2  UNL     1      -8.735   3.667   0.327  1.00  0.00           O  
HETATM   28  H1  UNL     1       9.289   1.622  -1.264  1.00  0.00           H  
HETATM   29  H2  UNL     1       8.174   0.872  -0.093  1.00  0.00           H  
HETATM   30  H3  UNL     1       8.812   2.586   0.150  1.00  0.00           H  
HETATM   31  H4  UNL     1       6.610   3.039  -0.714  1.00  0.00           H  
HETATM   32  H5  UNL     1       7.817   3.267  -1.975  1.00  0.00           H  
HETATM   33  H6  UNL     1       7.289   1.358  -3.184  1.00  0.00           H  
HETATM   34  H7  UNL     1       5.799   2.219  -2.780  1.00  0.00           H  
HETATM   35  H8  UNL     1       5.678  -0.182  -2.853  1.00  0.00           H  
HETATM   36  H9  UNL     1       6.832  -0.415  -1.553  1.00  0.00           H  
HETATM   37  H10 UNL     1       4.408  -0.725  -0.928  1.00  0.00           H  
HETATM   38  H11 UNL     1       4.129   0.966  -1.275  1.00  0.00           H  
HETATM   39  H12 UNL     1       5.487   1.769   0.675  1.00  0.00           H  
HETATM   40  H13 UNL     1       5.384   0.330   2.530  1.00  0.00           H  
HETATM   41  H14 UNL     1       4.905  -1.904   0.451  1.00  0.00           H  
HETATM   42  H15 UNL     1       5.697  -2.044   2.012  1.00  0.00           H  
HETATM   43  H16 UNL     1       3.628  -1.660   3.296  1.00  0.00           H  
HETATM   44  H17 UNL     1       1.639  -2.589   2.458  1.00  0.00           H  
HETATM   45  H18 UNL     1       3.322  -2.724  -0.173  1.00  0.00           H  
HETATM   46  H19 UNL     1       2.070  -3.830   0.326  1.00  0.00           H  
HETATM   47  H20 UNL     1       1.250  -2.429  -1.577  1.00  0.00           H  
HETATM   48  H21 UNL     1      -0.268  -0.800  -1.061  1.00  0.00           H  
HETATM   49  H22 UNL     1       0.155   0.625   0.808  1.00  0.00           H  
HETATM   50  H23 UNL     1       1.188  -0.455   1.705  1.00  0.00           H  
HETATM   51  H24 UNL     1      -0.922  -0.128   2.887  1.00  0.00           H  
HETATM   52  H25 UNL     1      -2.760  -1.406   2.495  1.00  0.00           H  
HETATM   53  H26 UNL     1      -1.554  -2.415  -0.266  1.00  0.00           H  
HETATM   54  H27 UNL     1      -2.603  -3.344   0.898  1.00  0.00           H  
HETATM   55  H28 UNL     1      -3.788  -2.429  -0.927  1.00  0.00           H  
HETATM   56  H29 UNL     1      -4.278  -1.849   0.747  1.00  0.00           H  
HETATM   57  H30 UNL     1      -2.931   0.225   0.388  1.00  0.00           H  
HETATM   58  H31 UNL     1      -2.534  -0.280  -1.283  1.00  0.00           H  
HETATM   59  H32 UNL     1      -4.362   1.303  -1.415  1.00  0.00           H  
HETATM   60  H33 UNL     1      -4.800  -0.320  -1.983  1.00  0.00           H  
HETATM   61  H34 UNL     1      -5.352   0.728   0.858  1.00  0.00           H  
HETATM   62  H35 UNL     1      -5.929  -0.865   0.107  1.00  0.00           H  
HETATM   63  H36 UNL     1      -8.056   0.491   1.113  1.00  0.00           H  
HETATM   64  H37 UNL     1     -10.074   1.395   0.394  1.00  0.00           H  
HETATM   65  H38 UNL     1      -9.620   0.847  -1.241  1.00  0.00           H  
HETATM   66  H39 UNL     1      -8.390   3.045  -1.594  1.00  0.00           H  
HETATM   67  H40 UNL     1     -10.093   3.265  -1.127  1.00  0.00           H  
HETATM   68  H41 UNL     1      -8.865   3.125   1.169  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   31   32
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6   37   38
CONECT    6    7    7   39
CONECT    7    8   40
CONECT    8    9   41   42
CONECT    9   10   10   43
CONECT   10   11   44
CONECT   11   12   45   46
CONECT   12   13   13   47
CONECT   13   14   48
CONECT   14   15   49   50
CONECT   15   16   16   51
CONECT   16   17   52
CONECT   17   18   53   54
CONECT   18   19   55   56
CONECT   19   20   57   58
CONECT   20   21   59   60
CONECT   21   22   61   62
CONECT   22   23   23   24
CONECT   24   25   63
CONECT   25   26   64   65
CONECT   26   27   66   67
CONECT   27   68
END

HMDB0013626
     RDKit          3D
Adrenoyl ethanolamide
 68 67  0  0  0  0  0  0  0  0999 V2000
    8.4388    1.8230   -0.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2930    2.4629   -1.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6073    1.5999   -2.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0224    0.3137   -1.8732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9586    0.2534   -0.8558 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2301    0.7010    0.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1621   -0.1040    1.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8147   -1.5182    1.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5857   -1.8619    2.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4674   -2.3737    1.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2972   -2.6773    0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2982   -2.0760   -0.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4113   -1.1673   -0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2594   -0.5458    1.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9326   -0.7295    1.9018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9658   -1.4507    1.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2384   -2.2973    0.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5510   -1.7630   -0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3171   -0.3450   -0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5631    0.2704   -1.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6716    0.2182   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9106    0.8209   -0.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8874    1.2749   -1.8212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0756    0.8700    0.1582 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2760    1.4479   -0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1057    2.9024   -0.7690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7354    3.6671    0.3275 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2893    1.6223   -1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1740    0.8716   -0.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8115    2.5865    0.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6103    3.0387   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8173    3.2666   -1.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2891    1.3579   -3.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7988    2.2188   -2.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6782   -0.1816   -2.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8319   -0.4150   -1.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4077   -0.7253   -0.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1290    0.9659   -1.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4865    1.7690    0.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3841    0.3302    2.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9053   -1.9044    0.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6967   -2.0442    2.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6280   -1.6599    3.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6390   -2.5893    2.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3224   -2.7242   -0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0704   -3.8299    0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2496   -2.4295   -1.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2684   -0.8000   -1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1548    0.6245    0.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1876   -0.4549    1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9221   -0.1282    2.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7597   -1.4055    2.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5540   -2.4150   -0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6029   -3.3438    0.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7878   -2.4291   -0.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2784   -1.8486    0.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9311    0.2249    0.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5336   -0.2798   -1.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3618    1.3031   -1.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8003   -0.3198   -1.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3517    0.7280    0.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9294   -0.8652    0.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0560    0.4915    1.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0737    1.3951    0.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6195    0.8469   -1.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3901    3.0453   -1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0928    3.2650   -1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8645    3.1254    1.1687 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  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 24 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-(7Z,10Z,13Z,16Z-Docosatetraenoyl)-ethanolamine	Kegg
7,10,13,16-DTEA	MeSH
7,10,13,16-Docosatetraenylethanolamide	MeSH
N-(7Z,10Z,13Z,16Z-Docosatetraenoyl)-ethanolamide	KEGG, HMDB
7,10,13,16-Docosatetraenoylethanolamine	HMDB
8,11,14-Eicosatrienoylethanolamide	HMDB
Adrenoyl-ethanolamine	HMDB
DEA	HMDB
Docosa-7,10,13,16-tetraenoate	HMDB
Docosa-7,10,13,16-tetraenoic acid	HMDB
Docosa-7,10,13,16-tetraenoic acid (2-hydroxy-ethyl)-amide	HMDB
N-(8Z,11Z,14Z-Icosatrienoyl)-ethanolamide	HMDB

Chemical Formula

C₂₄H₄₁NO₂

Average Molecular Weight

375.5878

Monoisotopic Molecular Weight

375.313729561

IUPAC Name

(7Z,10Z,13Z,16Z)-N-(2-hydroxyethyl)docosa-7,10,13,16-tetraenamide

Traditional Name

docosatetraenoylethanolamide

CAS Registry Number

150314-35-5

SMILES

CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(=O)NCCO

InChI Identifier

InChI=1S/C24H41NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(27)25-22-23-26/h6-7,9-10,12-13,15-16,26H,2-5,8,11,14,17-23H2,1H3,(H,25,27)/b7-6-,10-9-,13-12-,16-15-

InChI Key

FMVHVRYFQIXOAF-DOFZRALJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

N-acylethanolamines

Alternative Parents

Substituents

N-acylethanolamine
Fatty amide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

endocannabinoid (CHEBI:34478 )
N-acyl ethanolamides (endocannabinoids) (C13829 )
N-acyl ethanolamines (endocannabinoids) (LMFA08040047 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0013626)

Biofluid or Excreta

Blood (HMDB: HMDB0013626)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)

Cellular substructure

Extracellular (HMDB: HMDB0013626)
Membrane (HMDB: HMDB0013626)

Source

Endogenous

Endogenous (HMDB: HMDB0013626)

Exogenous

Food

Food (HMDB: HMDB0013626)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0013626)

Role

Biological role

Energy source (HMDB: HMDB0013626)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013626)

Emulsifier (HMDB: HMDB0013626)

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	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00019 g/L	ALOGPS
logP	6.58	ALOGPS
logP	6.2	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	15.46	ChemAxon
pKa (Strongest Basic)	-0.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	122.17 m³·mol⁻¹	ChemAxon
Polarizability	47.17 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	204.761	31661259
DarkChem	[M-H]-	205.648	31661259
DeepCCS	[M+H]+	199.513	30932474
DeepCCS	[M-H]-	197.155	30932474
DeepCCS	[M-2H]-	230.683	30932474
DeepCCS	[M+Na]+	205.934	30932474
AllCCS	[M+H]+	202.1	32859911
AllCCS	[M+H-H2O]+	199.7	32859911
AllCCS	[M+NH4]+	204.3	32859911
AllCCS	[M+Na]+	205.0	32859911
AllCCS	[M-H]-	200.0	32859911
AllCCS	[M+Na-2H]-	202.9	32859911
AllCCS	[M+HCOO]-	206.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Adrenoyl ethanolamide	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(=O)NCCO	3457.9	Standard polar	33892256
Adrenoyl ethanolamide	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(=O)NCCO	2769.0	Standard non polar	33892256
Adrenoyl ethanolamide	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(=O)NCCO	3050.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Adrenoyl ethanolamide,1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)NCCO[Si](C)(C)C	3070.9	Semi standard non polar	33892256
Adrenoyl ethanolamide,1TMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)N(CCO)[Si](C)(C)C	3009.1	Semi standard non polar	33892256
Adrenoyl ethanolamide,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	3054.6	Semi standard non polar	33892256
Adrenoyl ethanolamide,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	3091.0	Standard non polar	33892256
Adrenoyl ethanolamide,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	3050.0	Standard polar	33892256
Adrenoyl ethanolamide,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)NCCO[Si](C)(C)C(C)(C)C	3315.3	Semi standard non polar	33892256
Adrenoyl ethanolamide,1TBDMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C	3259.3	Semi standard non polar	33892256
Adrenoyl ethanolamide,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3552.6	Semi standard non polar	33892256
Adrenoyl ethanolamide,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3428.7	Standard non polar	33892256
Adrenoyl ethanolamide,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3098.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Adrenoyl ethanolamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-8596000000-fb56397a219ca27323ee	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adrenoyl ethanolamide GC-MS (1 TMS) - 70eV, Positive	splash10-00yi-9263400000-08ff1e6d3a4de7602967	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adrenoyl ethanolamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adrenoyl ethanolamide 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 - Adrenoyl ethanolamide 10V, Positive-QTOF	splash10-01t9-4019000000-af6365155318609eed17	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenoyl ethanolamide 20V, Positive-QTOF	splash10-03dl-9122000000-8e28d155f14c7badafed	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenoyl ethanolamide 40V, Positive-QTOF	splash10-03di-9130000000-e57644d2630bb1b3b060	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenoyl ethanolamide 10V, Negative-QTOF	splash10-00di-0009000000-7ec4d3341aea6c7e0b11	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenoyl ethanolamide 20V, Negative-QTOF	splash10-074l-5009000000-00b3c02e8e16ba5c1e65	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenoyl ethanolamide 40V, Negative-QTOF	splash10-0006-9011000000-d5cb6f4617816a6a0fb2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenoyl ethanolamide 10V, Negative-QTOF	splash10-00di-0009000000-19586eb33dc1d3f7d937	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenoyl ethanolamide 20V, Negative-QTOF	splash10-00di-4119000000-9b6fce221585710cf9dc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenoyl ethanolamide 40V, Negative-QTOF	splash10-052f-9002000000-b09284232013b6fc7b7a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenoyl ethanolamide 10V, Positive-QTOF	splash10-01t9-8119000000-da9fd03d8d325045c6d7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenoyl ethanolamide 20V, Positive-QTOF	splash10-03dl-9000000000-7ae2abc24b2249be27a2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrenoyl ethanolamide 40V, Positive-QTOF	splash10-03dl-9100000000-60701a0404a7efc4eea6	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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	1.63 +/- 0.78 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

FDB029603

KNApSAcK ID

Not Available

Chemspider ID

4445444

KEGG Compound ID

C13829

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282273

PDB ID

Not Available

ChEBI ID

269625

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

Hofmann U, Domeier E, Frantz S, Laser M, Weckler B, Kuhlencordt P, Heuer S, Keweloh B, Ertl G, Bonz AW: Increased myocardial oxygen consumption by TNF-alpha is mediated by a sphingosine signaling pathway. Am J Physiol Heart Circ Physiol. 2003 Jun;284(6):H2100-5. Epub 2003 Jan 30. [PubMed:12560208 ]
Tripathy S, Kleppinger-Sparace K, Dixon RA, Chapman KD: N-acylethanolamine signaling in tobacco is mediated by a membrane-associated, high-affinity binding protein. Plant Physiol. 2003 Apr;131(4):1781-91. [PubMed:12692337 ]
Lecour S, Smith RM, Woodward B, Opie LH, Rochette L, Sack MN: Identification of a novel role for sphingolipid signaling in TNF alpha and ischemic preconditioning mediated cardioprotection. J Mol Cell Cardiol. 2002 May;34(5):509-18. [PubMed:12056855 ]
Amadou A, Nawrocki A, Best-Belpomme M, Pavoine C, Pecker F: Arachidonic acid mediates dual effect of TNF-alpha on Ca2+ transients and contraction of adult rat cardiomyocytes. Am J Physiol Cell Physiol. 2002 Jun;282(6):C1339-47. [PubMed:11997249 ]

Showing metabocard for Adrenoyl ethanolamide (HMDB0013626)

MOL for HMDB0013626 (Adrenoyl ethanolamide)

3D MOL for HMDB0013626 (Adrenoyl ethanolamide)

3D SDF for HMDB0013626 (Adrenoyl ethanolamide)

3D-SDF for HMDB0013626 (Adrenoyl ethanolamide)

PDB for HMDB0013626 (Adrenoyl ethanolamide)

3D PDB for HMDB0013626 (Adrenoyl ethanolamide)

SMILES for HMDB0013626 (Adrenoyl ethanolamide)

INCHI for HMDB0013626 (Adrenoyl ethanolamide)

Structure for HMDB0013626 (Adrenoyl ethanolamide)

3D Structure for HMDB0013626 (Adrenoyl ethanolamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra