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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2010-05-20 13:47:29 UTC

Update Date

2022-03-07 02:51:34 UTC

HMDB ID

HMDB0013630

Secondary Accession Numbers

HMDB13630

Metabolite Identification

Common Name

20-HETE ethanolamide

Description

20-HETE ethanolamide is an 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 signalling 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


  Mrv1652303291817582D          

 26 25  0  0  0  0            999 V2000
 9995.4803 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1949 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9094 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7347 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4493 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1638 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9891 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7035 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4208 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.2456 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.9610 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.6743 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.4990 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.2144 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.9298 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.6431 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.3585 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.0739 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.7872 9999.7989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.7657 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.0512 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.3364 9999.3866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9992.6218 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.9072 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.1927 9999.7989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.051210000.6233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  2  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
M  END

HMDB0013630
     RDKit          3D
20-HETE ethanolamide
 63 62  0  0  0  0  0  0  0  0999 V2000
    5.8810    0.0424    0.9856 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6791   -0.9182    0.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3270   -2.2276    1.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9001   -2.3338    1.7535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9141   -2.3915    0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9159   -1.2987   -0.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8935   -0.4872   -0.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6531   -0.6319    0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599   -0.8898   -0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5253   -0.1875   -0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7661    1.0291   -0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8505    2.1619   -0.9506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8859    2.9235   -1.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1242    2.7510   -0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2400    2.5189   -1.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0186    1.4639   -1.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8358    0.3526   -0.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1118    0.1607    0.4871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2851   -0.1620   -0.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5262   -0.3401    0.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3538   -1.4530    1.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5674   -1.5384    2.1703 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8759   -0.7933    0.0878 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2923    0.4273   -0.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5568    1.5621    0.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4884    1.9524    1.1887 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6319   -3.0458    0.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9293   -2.3844    2.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7129   -3.2499    2.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6246   -1.4494    2.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9200   -2.7456    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2309   -3.3195   -0.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8093   -1.1804   -0.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9663    0.2987   -1.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5724    0.3816    0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6701   -1.4083    1.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6862   -1.7826   -1.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2846   -0.4797   -1.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6932    0.8268    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0011    1.2041    0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645    2.3200   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8042    3.7367   -1.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0893    2.1162    0.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2847    3.8038    0.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3994    3.3465   -1.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8137    1.4197   -2.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9515    0.3773    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7578   -0.5792   -0.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9533   -0.6886    1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3158    1.1177    1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1151   -1.1457   -0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4368    0.5700   -1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6587    0.6031    1.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4182   -0.5600   -0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1056   -2.3970    0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5936   -1.2339    2.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2837   -1.5406    1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4954   -1.6388   -0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1797    0.2403   -1.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4631    0.7381   -1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9929    2.4399   -0.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3588    1.2439    1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8033    2.3522    2.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  2 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 23 58  1  0
 24 59  1  0
 24 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  0
M  END


  Mrv1652303291817582D          

 26 25  0  0  0  0            999 V2000
 9995.4803 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1949 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9094 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7347 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4493 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1638 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9891 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7035 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4208 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.2456 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.9610 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.6743 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.4990 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.2144 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.9298 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.6431 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.3585 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.0739 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.7872 9999.7989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.7657 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.0512 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.3364 9999.3866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9992.6218 9999.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.9072 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.1927 9999.7989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.051210000.6233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  2  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
M  END
> <DATABASE_ID>
HMDB0013630

> <DATABASE_NAME>
hmdb

> <SMILES>
OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO

> <INCHI_IDENTIFIER>
InChI=1S/C22H37NO3/c24-20-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-22(26)23-19-21-25/h1,3-4,6-7,9-10,12,24-25H,2,5,8,11,13-21H2,(H,23,26)/b3-1-,6-4-,9-7-,12-10-

> <INCHI_KEY>
QRMZDMUHHZLRMH-DTLRTWKJSA-N

> <FORMULA>
C22H37NO3

> <MOLECULAR_WEIGHT>
363.5341

> <EXACT_MASS>
363.277344055

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
44.18547319965994

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,11Z,14Z)-20-hydroxy-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide

> <ALOGPS_LOGP>
4.88

> <JCHEM_LOGP>
3.877123634333334

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.375825066096787

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.435299736387627

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2323639576211178

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
114.89389999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.81e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
20-hete-EA

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013630
     RDKit          3D
20-HETE ethanolamide
 63 62  0  0  0  0  0  0  0  0999 V2000
    5.8810    0.0424    0.9856 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6791   -0.9182    0.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3270   -2.2276    1.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9001   -2.3338    1.7535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9141   -2.3915    0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9159   -1.2987   -0.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8935   -0.4872   -0.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6531   -0.6319    0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599   -0.8898   -0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5253   -0.1875   -0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7661    1.0291   -0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8505    2.1619   -0.9506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8859    2.9235   -1.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1242    2.7510   -0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2400    2.5189   -1.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0186    1.4639   -1.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8358    0.3526   -0.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1118    0.1607    0.4871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2851   -0.1620   -0.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5262   -0.3401    0.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3538   -1.4530    1.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5674   -1.5384    2.1703 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8759   -0.7933    0.0878 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2923    0.4273   -0.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5568    1.5621    0.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4884    1.9524    1.1887 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6319   -3.0458    0.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9293   -2.3844    2.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7129   -3.2499    2.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6246   -1.4494    2.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9200   -2.7456    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2309   -3.3195   -0.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8093   -1.1804   -0.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9663    0.2987   -1.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5724    0.3816    0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6701   -1.4083    1.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6862   -1.7826   -1.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2846   -0.4797   -1.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6932    0.8268    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0011    1.2041    0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645    2.3200   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8042    3.7367   -1.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0893    2.1162    0.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2847    3.8038    0.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3994    3.3465   -1.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8137    1.4197   -2.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9515    0.3773    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7578   -0.5792   -0.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9533   -0.6886    1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3158    1.1177    1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1151   -1.1457   -0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4368    0.5700   -1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6587    0.6031    1.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4182   -0.5600   -0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1056   -2.3970    0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5936   -1.2339    2.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2837   -1.5406    1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4954   -1.6388   -0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1797    0.2403   -1.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4631    0.7381   -1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9929    2.4399   -0.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3588    1.2439    1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8033    2.3522    2.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  2 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 23 58  1  0
 24 59  1  0
 24 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  0
M  END

HEADER    PROTEIN                                 29-MAR-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-MAR-18         0                                  
HETATM    1  C   UNK     0    8658.2308666.291   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8659.5648665.522   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8660.8988666.291   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8662.4388666.291   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8663.7728665.522   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8665.1068666.291   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8666.6468666.291   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8667.9808665.522   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8669.3198666.291   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8670.8588666.291   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8672.1948665.522   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8673.5258666.291   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8675.0658666.291   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8676.4008665.522   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8677.7368666.291   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8679.0678665.522   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8680.4038666.291   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8681.7388665.522   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8683.0698666.291   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    8656.8968665.522   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8655.5628666.291   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0    8654.2288665.522   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0    8652.8948666.291   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8651.5608665.522   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0    8650.2268666.291   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0    8655.5628667.830   0.000  0.00  0.00           O+0
CONECT    1    2   20                                                       
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                                                            
CONECT   20    1   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   21                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

COMPND    HMDB0013630
HETATM    1  O1  UNL     1       5.881   0.042   0.986  1.00  0.00           O  
HETATM    2  C1  UNL     1       6.679  -0.918   0.818  1.00  0.00           C  
HETATM    3  C2  UNL     1       6.327  -2.228   1.422  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.900  -2.334   1.754  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.914  -2.392   0.637  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.916  -1.299  -0.326  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.893  -0.487  -0.483  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.653  -0.632   0.326  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.560  -0.890  -0.634  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.525  -0.188  -0.819  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.766   1.029  -0.007  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.851   2.162  -0.951  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.886   2.924  -1.085  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.124   2.751  -0.303  1.00  0.00           C  
HETATM   15  C14 UNL     1      -4.240   2.519  -1.256  1.00  0.00           C  
HETATM   16  C15 UNL     1      -5.019   1.464  -1.300  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.836   0.353  -0.341  1.00  0.00           C  
HETATM   18  C17 UNL     1      -6.112   0.161   0.487  1.00  0.00           C  
HETATM   19  C18 UNL     1      -7.285  -0.162  -0.378  1.00  0.00           C  
HETATM   20  C19 UNL     1      -8.526  -0.340   0.462  1.00  0.00           C  
HETATM   21  C20 UNL     1      -8.354  -1.453   1.444  1.00  0.00           C  
HETATM   22  O2  UNL     1      -9.567  -1.538   2.170  1.00  0.00           O  
HETATM   23  N1  UNL     1       7.876  -0.793   0.088  1.00  0.00           N  
HETATM   24  C21 UNL     1       8.292   0.427  -0.515  1.00  0.00           C  
HETATM   25  C22 UNL     1       8.557   1.562   0.431  1.00  0.00           C  
HETATM   26  O3  UNL     1       7.488   1.952   1.189  1.00  0.00           O  
HETATM   27  H1  UNL     1       6.632  -3.046   0.726  1.00  0.00           H  
HETATM   28  H2  UNL     1       6.929  -2.384   2.342  1.00  0.00           H  
HETATM   29  H3  UNL     1       4.713  -3.250   2.389  1.00  0.00           H  
HETATM   30  H4  UNL     1       4.625  -1.449   2.413  1.00  0.00           H  
HETATM   31  H5  UNL     1       2.920  -2.746   0.987  1.00  0.00           H  
HETATM   32  H6  UNL     1       4.231  -3.319  -0.016  1.00  0.00           H  
HETATM   33  H7  UNL     1       4.809  -1.180  -0.980  1.00  0.00           H  
HETATM   34  H8  UNL     1       2.966   0.299  -1.218  1.00  0.00           H  
HETATM   35  H9  UNL     1       1.572   0.382   0.836  1.00  0.00           H  
HETATM   36  H10 UNL     1       1.670  -1.408   1.088  1.00  0.00           H  
HETATM   37  H11 UNL     1       0.686  -1.783  -1.262  1.00  0.00           H  
HETATM   38  H12 UNL     1      -1.285  -0.480  -1.578  1.00  0.00           H  
HETATM   39  H13 UNL     1      -1.693   0.827   0.569  1.00  0.00           H  
HETATM   40  H14 UNL     1       0.001   1.204   0.758  1.00  0.00           H  
HETATM   41  H15 UNL     1       0.064   2.320  -1.557  1.00  0.00           H  
HETATM   42  H16 UNL     1      -1.804   3.737  -1.832  1.00  0.00           H  
HETATM   43  H17 UNL     1      -3.089   2.116   0.562  1.00  0.00           H  
HETATM   44  H18 UNL     1      -3.285   3.804   0.159  1.00  0.00           H  
HETATM   45  H19 UNL     1      -4.399   3.347  -1.992  1.00  0.00           H  
HETATM   46  H20 UNL     1      -5.814   1.420  -2.067  1.00  0.00           H  
HETATM   47  H21 UNL     1      -3.952   0.377   0.270  1.00  0.00           H  
HETATM   48  H22 UNL     1      -4.758  -0.579  -0.982  1.00  0.00           H  
HETATM   49  H23 UNL     1      -5.953  -0.689   1.202  1.00  0.00           H  
HETATM   50  H24 UNL     1      -6.316   1.118   1.010  1.00  0.00           H  
HETATM   51  H25 UNL     1      -7.115  -1.146  -0.899  1.00  0.00           H  
HETATM   52  H26 UNL     1      -7.437   0.570  -1.187  1.00  0.00           H  
HETATM   53  H27 UNL     1      -8.659   0.603   1.060  1.00  0.00           H  
HETATM   54  H28 UNL     1      -9.418  -0.560  -0.144  1.00  0.00           H  
HETATM   55  H29 UNL     1      -8.106  -2.397   0.946  1.00  0.00           H  
HETATM   56  H30 UNL     1      -7.594  -1.234   2.244  1.00  0.00           H  
HETATM   57  H31 UNL     1     -10.284  -1.541   1.465  1.00  0.00           H  
HETATM   58  H32 UNL     1       8.495  -1.639  -0.020  1.00  0.00           H  
HETATM   59  H33 UNL     1       9.180   0.240  -1.174  1.00  0.00           H  
HETATM   60  H34 UNL     1       7.463   0.738  -1.232  1.00  0.00           H  
HETATM   61  H35 UNL     1       8.993   2.440  -0.122  1.00  0.00           H  
HETATM   62  H36 UNL     1       9.359   1.244   1.167  1.00  0.00           H  
HETATM   63  H37 UNL     1       7.803   2.352   2.047  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   23
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7    7   33
CONECT    7    8   34
CONECT    8    9   35   36
CONECT    9   10   10   37
CONECT   10   11   38
CONECT   11   12   39   40
CONECT   12   13   13   41
CONECT   13   14   42
CONECT   14   15   43   44
CONECT   15   16   16   45
CONECT   16   17   46
CONECT   17   18   47   48
CONECT   18   19   49   50
CONECT   19   20   51   52
CONECT   20   21   53   54
CONECT   21   22   55   56
CONECT   22   57
CONECT   23   24   58
CONECT   24   25   59   60
CONECT   25   26   61   62
CONECT   26   63
END

HMDB0013630
     RDKit          3D
20-HETE ethanolamide
 63 62  0  0  0  0  0  0  0  0999 V2000
    5.8810    0.0424    0.9856 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6791   -0.9182    0.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3270   -2.2276    1.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9001   -2.3338    1.7535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9141   -2.3915    0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9159   -1.2987   -0.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8935   -0.4872   -0.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6531   -0.6319    0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599   -0.8898   -0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5253   -0.1875   -0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7661    1.0291   -0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8505    2.1619   -0.9506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8859    2.9235   -1.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1242    2.7510   -0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2400    2.5189   -1.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0186    1.4639   -1.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8358    0.3526   -0.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1118    0.1607    0.4871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2851   -0.1620   -0.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5262   -0.3401    0.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3538   -1.4530    1.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5674   -1.5384    2.1703 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8759   -0.7933    0.0878 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2923    0.4273   -0.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5568    1.5621    0.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4884    1.9524    1.1887 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6319   -3.0458    0.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9293   -2.3844    2.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7129   -3.2499    2.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6246   -1.4494    2.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9200   -2.7456    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2309   -3.3195   -0.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8093   -1.1804   -0.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9663    0.2987   -1.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5724    0.3816    0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6701   -1.4083    1.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6862   -1.7826   -1.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2846   -0.4797   -1.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6932    0.8268    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0011    1.2041    0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645    2.3200   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8042    3.7367   -1.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0893    2.1162    0.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2847    3.8038    0.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3994    3.3465   -1.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8137    1.4197   -2.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9515    0.3773    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7578   -0.5792   -0.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9533   -0.6886    1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3158    1.1177    1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1151   -1.1457   -0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4368    0.5700   -1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6587    0.6031    1.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4182   -0.5600   -0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1056   -2.3970    0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5936   -1.2339    2.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2837   -1.5406    1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4954   -1.6388   -0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1797    0.2403   -1.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4631    0.7381   -1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9929    2.4399   -0.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3588    1.2439    1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8033    2.3522    2.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  2 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 23 58  1  0
 24 59  1  0
 24 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
20-HETE-ea	ChEBI
20-HETE-ethanolamine	ChEBI
20-Hydroxy-5,8,11,14-eicosatetraenoic acid ethanolamide	ChEBI
20-Hydroxy-5,8,11,14-icosatetraenoic acid ethanolamide	ChEBI
20-Hydroxyanandamide	ChEBI
20-Hydroxyarachidonic acid ethanolamide	ChEBI
N-(20-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine	ChEBI
N-(20-Hydroxy-5Z,8Z,11Z,14Z-icosatetraenoyl)ethanolamine	ChEBI
N-[5Z,8Z,11Z,14Z-20-Hydroxyicosatetraenoyl]ethanolamine	ChEBI
20-Hydroxy-5,8,11,14-eicosatetraenoate ethanolamide	Generator
20-Hydroxy-5,8,11,14-icosatetraenoate ethanolamide	Generator
20-Hydroxyarachidonate ethanolamide	Generator
20-HETE ea	HMDB
20-Hydroxy aea	HMDB
20-Hydroxy arachidonoyl ethanolamide	HMDB
20-Hydroxyepoxyeicosatrienoate	HMDB
20-Hydroxyepoxyeicosatrienoic acid	HMDB
20-Hydroxyepoxyeicosatrienoic acid ethanolamide	HMDB

Chemical Formula

C₂₂H₃₇NO₃

Average Molecular Weight

363.5341

Monoisotopic Molecular Weight

363.277344055

IUPAC Name

(5Z,8Z,11Z,14Z)-20-hydroxy-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide

Traditional Name

20-hete-EA

CAS Registry Number

942069-11-6

SMILES

OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO

InChI Identifier

InChI=1S/C22H37NO3/c24-20-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-22(26)23-19-21-25/h1,3-4,6-7,9-10,12,24-25H,2,5,8,11,13-21H2,(H,23,26)/b3-1-,6-4-,9-7-,12-10-

InChI Key

QRMZDMUHHZLRMH-DTLRTWKJSA-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

N-acyl ethanolamines (endocannabinoids) (LMFA08040039 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0013630)

Biofluid or Excreta

Blood (HMDB: HMDB0013630)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)

Cellular substructure

Extracellular (HMDB: HMDB0013630)
Membrane (HMDB: HMDB0013630)

Source

Endogenous

Endogenous (HMDB: HMDB0013630)

Exogenous

Food

Food (HMDB: HMDB0013630)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0013630)

Role

Biological role

Energy source (HMDB: HMDB0013630)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013630)

Emulsifier (HMDB: HMDB0013630)

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	0.0028 g/L	ALOGPS
logP	4.88	ALOGPS
logP	3.88	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	15.44	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	114.89 m³·mol⁻¹	ChemAxon
Polarizability	44.19 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	197.207	31661259
DarkChem	[M-H]-	203.001	31661259
DeepCCS	[M+H]+	193.867	30932474
DeepCCS	[M-H]-	191.509	30932474
DeepCCS	[M-2H]-	224.649	30932474
DeepCCS	[M+Na]+	200.056	30932474
AllCCS	[M+H]+	194.1	32859911
AllCCS	[M+H-H2O]+	191.7	32859911
AllCCS	[M+NH4]+	196.4	32859911
AllCCS	[M+Na]+	197.1	32859911
AllCCS	[M-H]-	194.2	32859911
AllCCS	[M+Na-2H]-	196.6	32859911
AllCCS	[M+HCOO]-	199.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
20-HETE ethanolamide	OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO	3642.7	Standard polar	33892256
20-HETE ethanolamide	OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO	2512.6	Standard non polar	33892256
20-HETE ethanolamide	OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO	3136.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
20-HETE ethanolamide,1TMS,isomer #1	C[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO	3172.1	Semi standard non polar	33892256
20-HETE ethanolamide,1TMS,isomer #2	C[Si](C)(C)OCCNC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCO	3141.3	Semi standard non polar	33892256
20-HETE ethanolamide,1TMS,isomer #3	C[Si](C)(C)N(CCO)C(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCO	3060.8	Semi standard non polar	33892256
20-HETE ethanolamide,2TMS,isomer #1	C[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO[Si](C)(C)C	3131.4	Semi standard non polar	33892256
20-HETE ethanolamide,2TMS,isomer #2	C[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO)[Si](C)(C)C	3097.8	Semi standard non polar	33892256
20-HETE ethanolamide,2TMS,isomer #3	C[Si](C)(C)OCCN(C(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCO)[Si](C)(C)C	3107.1	Semi standard non polar	33892256
20-HETE ethanolamide,3TMS,isomer #1	C[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	3115.6	Semi standard non polar	33892256
20-HETE ethanolamide,3TMS,isomer #1	C[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	3157.7	Standard non polar	33892256
20-HETE ethanolamide,3TMS,isomer #1	C[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	3028.3	Standard polar	33892256
20-HETE ethanolamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO	3427.1	Semi standard non polar	33892256
20-HETE ethanolamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCCNC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCO	3378.9	Semi standard non polar	33892256
20-HETE ethanolamide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCO)C(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCO	3301.1	Semi standard non polar	33892256
20-HETE ethanolamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO[Si](C)(C)C(C)(C)C	3648.3	Semi standard non polar	33892256
20-HETE ethanolamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C	3568.0	Semi standard non polar	33892256
20-HETE ethanolamide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCCN(C(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCO)[Si](C)(C)C(C)(C)C	3583.0	Semi standard non polar	33892256
20-HETE ethanolamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3863.0	Semi standard non polar	33892256
20-HETE ethanolamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3660.0	Standard non polar	33892256
20-HETE ethanolamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3149.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 20-HETE ethanolamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0j59-3589000000-3b2241d486c86688ef75	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 20-HETE ethanolamide GC-MS (2 TMS) - 70eV, Positive	splash10-0fdo-5439700000-2ce10d8e6ec266bf7497	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 20-HETE 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 - 20-HETE ethanolamide 10V, Positive-QTOF	splash10-03dj-3019000000-f2029ffb36e80f0831fa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-HETE ethanolamide 20V, Positive-QTOF	splash10-03dl-9023000000-b8b72230e0c2ee44dd70	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-HETE ethanolamide 40V, Positive-QTOF	splash10-03dl-9131000000-46f2377e1f133b01723b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-HETE ethanolamide 10V, Negative-QTOF	splash10-03di-0009000000-f110e36f00b594851805	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-HETE ethanolamide 20V, Negative-QTOF	splash10-03dl-3009000000-83198bcf34c23d1f14af	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-HETE ethanolamide 40V, Negative-QTOF	splash10-0006-9011000000-a8fbb4764172356595f9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-HETE ethanolamide 10V, Negative-QTOF	splash10-03di-0009000000-9e3358e490a06a8fff0c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-HETE ethanolamide 20V, Negative-QTOF	splash10-03di-3119000000-5a324625cccf8671a86f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-HETE ethanolamide 40V, Negative-QTOF	splash10-0006-9003000000-97c2fbd008005d741243	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-HETE ethanolamide 10V, Positive-QTOF	splash10-03di-7219000000-ae8a82a0373146ed1cda	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-HETE ethanolamide 20V, Positive-QTOF	splash10-03dl-9001000000-0044622ae985419b2409	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-HETE ethanolamide 40V, Positive-QTOF	splash10-03di-9300000000-46979c19002f897fe2ed	2021-09-24	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	0.0208 +/- 0.013 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

FDB029607

KNApSAcK ID

Not Available

Chemspider ID

21467685

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

35027640

PDB ID

Not Available

ChEBI ID

136992

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 20-HETE ethanolamide (HMDB0013630)

MOL for HMDB0013630 (20-HETE ethanolamide)

3D MOL for HMDB0013630 (20-HETE ethanolamide)

3D SDF for HMDB0013630 (20-HETE ethanolamide)

3D-SDF for HMDB0013630 (20-HETE ethanolamide)

PDB for HMDB0013630 (20-HETE ethanolamide)

3D PDB for HMDB0013630 (20-HETE ethanolamide)

SMILES for HMDB0013630 (20-HETE ethanolamide)

INCHI for HMDB0013630 (20-HETE ethanolamide)

Structure for HMDB0013630 (20-HETE ethanolamide)

3D Structure for HMDB0013630 (20-HETE ethanolamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra