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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2011-07-11 10:54:15 UTC

Update Date

2022-03-07 02:51:34 UTC

HMDB ID

HMDB0013655

Secondary Accession Numbers

HMDB13655

Metabolite Identification

Common Name

O-Arachidonoyl Ethanolamine

Description

Arachidonoyl ethanolamide (AEA) was the first endogenous cannabinoid to be isolated and characterized as an agonist acting on the same receptors (CB1 and CB2) as tetrahydrocannabinols (THC). Since that time, a number of related endocannabinoids have been isolated, most notably 2-arachidonoyl glycerol (2-AG).O-Arachidonoyl ethanolamine hydrochloride (O-AEA) is a recently isolated constituent of human and rat brain wherein the ethanolamine moiety is attached "backwards", as an ester instead of an amide, as in AEA.1,2,4 O-AEA has mixed agonist/antagonist activity at the CB1 receptor and does not appear to be the native endogenous cannabinoid agonist at this receptor. This is in keeping with other observations that 2-AG is the primary endogenous CB1 receptor ligand.

Structure

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

HMDB0013655
     RDKit          3D
O-Arachidonoyl Ethanolamine
 62 61  0  0  0  0  0  0  0  0999 V2000
    8.3501   -0.1709   -1.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9068   -0.3585   -1.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7816   -0.6657    0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3175   -0.8487    0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1863   -1.1671    1.8678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7183   -0.0749    2.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9966    0.5821    3.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5659    0.3075    3.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8282    1.5516    3.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8811    1.6352    2.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4602    0.4477    1.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6190    0.7056    0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5866    0.6177   -0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7883    0.2737   -0.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2046   -0.9558   -0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2067   -0.9827   -1.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0781    0.1515   -1.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5328   -0.2038   -1.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3531    1.0116   -1.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7932    0.8156   -1.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0962    0.9420   -0.3069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7531    0.5190   -2.4308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1126    0.3275   -2.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2709   -0.8338   -1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6605   -1.0877   -0.8760 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5353   -0.4875   -2.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9824   -0.7587   -1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6066    0.8992   -1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5151   -1.2009   -2.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2777    0.5303   -1.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2832   -1.6408    0.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2894    0.0938    0.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7611    0.0862    0.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8772   -1.7115   -0.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1746   -1.4954    2.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8888   -2.0578    1.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8019    0.1998    2.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4850    1.4044    4.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2002   -0.6125    3.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5002    0.1883    4.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1462    2.4453    4.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3716    2.6103    2.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3769    0.3533    2.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8970   -0.5018    2.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5906    0.9764   -0.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7710    0.8255   -1.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9535    0.0127    1.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4395    1.1396   -0.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5791   -1.8370   -0.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4338   -1.9363   -2.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8556    1.0582   -1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1025    0.3760   -3.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5217   -0.4071   -0.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7958   -1.0840   -2.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2537    1.2233   -2.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9935    1.8660   -1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7224    0.1509   -3.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5424    1.2590   -1.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7555   -0.6295   -0.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7987   -1.7258   -1.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6728   -1.6032    0.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2595   -0.2574   -0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
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 14 48  1  0
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 16 50  1  0
 17 51  1  0
 17 52  1  0
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 19 55  1  0
 19 56  1  0
 23 57  1  0
 23 58  1  0
 24 59  1  0
 24 60  1  0
 25 61  1  0
 25 62  1  0
M  END


  Mrv0541 02271200292D          

 25 24  0  0  0  0            999 V2000
    4.9092   -9.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6237   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3382   -9.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0526   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7671   -9.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4816   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1960   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9106   -9.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6250   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3395   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0540   -9.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7684   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4829   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1974   -9.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9119   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6264   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3409   -9.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0553   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7698   -9.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4843   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1987   -9.0777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4843  -10.3152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9132   -9.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6277   -9.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3421   -9.4902    0.0000 N   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
 20 22  2  0  0  0  0
 23 21  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013655

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCCN

> <INCHI_IDENTIFIER>
InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)25-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21,23H2,1H3/b7-6-,10-9-,13-12-,16-15-

> <INCHI_KEY>
DLHLOYYQQGSXCC-DOFZRALJSA-N

> <FORMULA>
C22H37NO2

> <MOLECULAR_WEIGHT>
347.5347

> <EXACT_MASS>
347.282429433

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
42.969143903201186

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-aminoethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate

> <ALOGPS_LOGP>
6.27

> <JCHEM_LOGP>
5.9360810583333325

> <ALOGPS_LOGS>
-6.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.226362426441638

> <JCHEM_POLAR_SURFACE_AREA>
52.32

> <JCHEM_REFRACTIVITY>
112.67289999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.28e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
virodhamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013655
     RDKit          3D
O-Arachidonoyl Ethanolamine
 62 61  0  0  0  0  0  0  0  0999 V2000
    8.3501   -0.1709   -1.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9068   -0.3585   -1.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7816   -0.6657    0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3175   -0.8487    0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1863   -1.1671    1.8678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7183   -0.0749    2.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9966    0.5821    3.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5659    0.3075    3.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8282    1.5516    3.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8811    1.6352    2.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4602    0.4477    1.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6190    0.7056    0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5866    0.6177   -0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7883    0.2737   -0.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2046   -0.9558   -0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2067   -0.9827   -1.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0781    0.1515   -1.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5328   -0.2038   -1.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3531    1.0116   -1.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7932    0.8156   -1.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0962    0.9420   -0.3069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7531    0.5190   -2.4308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1126    0.3275   -2.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2709   -0.8338   -1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6605   -1.0877   -0.8760 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5353   -0.4875   -2.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9824   -0.7587   -1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6066    0.8992   -1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5151   -1.2009   -2.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2777    0.5303   -1.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2832   -1.6408    0.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2894    0.0938    0.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7611    0.0862    0.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8772   -1.7115   -0.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1746   -1.4954    2.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8888   -2.0578    1.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8019    0.1998    2.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4850    1.4044    4.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2002   -0.6125    3.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5002    0.1883    4.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1462    2.4453    4.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3716    2.6103    2.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3769    0.3533    2.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8970   -0.5018    2.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5906    0.9764   -0.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7710    0.8255   -1.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9535    0.0127    1.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4395    1.1396   -0.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5791   -1.8370   -0.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4338   -1.9363   -2.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8556    1.0582   -1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1025    0.3760   -3.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5217   -0.4071   -0.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7958   -1.0840   -2.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2537    1.2233   -2.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9935    1.8660   -1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7224    0.1509   -3.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5424    1.2590   -1.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7555   -0.6295   -0.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7987   -1.7258   -1.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6728   -1.6032    0.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2595   -0.2574   -0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 23 57  1  0
 23 58  1  0
 24 59  1  0
 24 60  1  0
 25 61  1  0
 25 62  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       9.164 -16.945   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.498 -17.715   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.831 -16.945   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.165 -17.715   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.499 -16.945   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.832 -17.715   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.166 -17.715   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.500 -16.945   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.833 -17.715   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.167 -17.715   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.501 -16.945   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.834 -17.715   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.168 -17.715   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.502 -16.945   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.836 -17.715   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.169 -17.715   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      30.503 -16.945   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.837 -17.715   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.170 -16.945   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      34.504 -17.715   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      35.838 -16.945   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      34.504 -19.255   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      37.171 -17.715   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      38.505 -16.945   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      39.839 -17.715   0.000  0.00  0.00           N+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   22                                                  
CONECT   21   20   23                                                       
CONECT   22   20                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

COMPND    HMDB0013655
HETATM    1  C1  UNL     1       8.350  -0.171  -1.882  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.907  -0.358  -1.485  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.782  -0.666   0.002  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.318  -0.849   0.371  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.186  -1.167   1.868  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.718  -0.075   2.679  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.997   0.582   3.552  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.566   0.308   3.829  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.828   1.552   3.534  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.881   1.635   2.653  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.460   0.448   1.853  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.619   0.706   0.402  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.587   0.618  -0.401  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.788   0.274  -0.029  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.205  -0.956  -0.783  1.00  0.00           C  
HETATM   16  C16 UNL     1      -2.207  -0.983  -1.590  1.00  0.00           C  
HETATM   17  C17 UNL     1      -3.078   0.152  -1.894  1.00  0.00           C  
HETATM   18  C18 UNL     1      -4.533  -0.204  -1.501  1.00  0.00           C  
HETATM   19  C19 UNL     1      -5.353   1.012  -1.846  1.00  0.00           C  
HETATM   20  C20 UNL     1      -6.793   0.816  -1.518  1.00  0.00           C  
HETATM   21  O1  UNL     1      -7.096   0.942  -0.307  1.00  0.00           O  
HETATM   22  O2  UNL     1      -7.753   0.519  -2.431  1.00  0.00           O  
HETATM   23  C21 UNL     1      -9.113   0.328  -2.140  1.00  0.00           C  
HETATM   24  C22 UNL     1      -9.271  -0.834  -1.215  1.00  0.00           C  
HETATM   25  N1  UNL     1     -10.661  -1.088  -0.876  1.00  0.00           N  
HETATM   26  H1  UNL     1       8.535  -0.487  -2.930  1.00  0.00           H  
HETATM   27  H2  UNL     1       8.982  -0.759  -1.170  1.00  0.00           H  
HETATM   28  H3  UNL     1       8.607   0.899  -1.727  1.00  0.00           H  
HETATM   29  H4  UNL     1       6.515  -1.201  -2.091  1.00  0.00           H  
HETATM   30  H5  UNL     1       6.278   0.530  -1.740  1.00  0.00           H  
HETATM   31  H6  UNL     1       7.283  -1.641   0.170  1.00  0.00           H  
HETATM   32  H7  UNL     1       7.289   0.094   0.607  1.00  0.00           H  
HETATM   33  H8  UNL     1       4.761   0.086   0.209  1.00  0.00           H  
HETATM   34  H9  UNL     1       4.877  -1.711  -0.164  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.175  -1.495   2.056  1.00  0.00           H  
HETATM   36  H11 UNL     1       5.889  -2.058   1.991  1.00  0.00           H  
HETATM   37  H12 UNL     1       6.802   0.200   2.541  1.00  0.00           H  
HETATM   38  H13 UNL     1       5.485   1.404   4.129  1.00  0.00           H  
HETATM   39  H14 UNL     1       3.200  -0.612   3.427  1.00  0.00           H  
HETATM   40  H15 UNL     1       3.500   0.188   4.980  1.00  0.00           H  
HETATM   41  H16 UNL     1       3.146   2.445   4.136  1.00  0.00           H  
HETATM   42  H17 UNL     1       1.372   2.610   2.490  1.00  0.00           H  
HETATM   43  H18 UNL     1       0.377   0.353   2.080  1.00  0.00           H  
HETATM   44  H19 UNL     1       1.897  -0.502   2.155  1.00  0.00           H  
HETATM   45  H20 UNL     1       2.591   0.976  -0.023  1.00  0.00           H  
HETATM   46  H21 UNL     1       0.771   0.825  -1.480  1.00  0.00           H  
HETATM   47  H22 UNL     1      -0.953   0.013   1.029  1.00  0.00           H  
HETATM   48  H23 UNL     1      -1.440   1.140  -0.225  1.00  0.00           H  
HETATM   49  H24 UNL     1      -0.579  -1.837  -0.587  1.00  0.00           H  
HETATM   50  H25 UNL     1      -2.434  -1.936  -2.099  1.00  0.00           H  
HETATM   51  H26 UNL     1      -2.856   1.058  -1.351  1.00  0.00           H  
HETATM   52  H27 UNL     1      -3.103   0.376  -3.005  1.00  0.00           H  
HETATM   53  H28 UNL     1      -4.522  -0.407  -0.420  1.00  0.00           H  
HETATM   54  H29 UNL     1      -4.796  -1.084  -2.088  1.00  0.00           H  
HETATM   55  H30 UNL     1      -5.254   1.223  -2.914  1.00  0.00           H  
HETATM   56  H31 UNL     1      -4.993   1.866  -1.257  1.00  0.00           H  
HETATM   57  H32 UNL     1      -9.722   0.151  -3.051  1.00  0.00           H  
HETATM   58  H33 UNL     1      -9.542   1.259  -1.672  1.00  0.00           H  
HETATM   59  H34 UNL     1      -8.755  -0.630  -0.259  1.00  0.00           H  
HETATM   60  H35 UNL     1      -8.799  -1.726  -1.703  1.00  0.00           H  
HETATM   61  H36 UNL     1     -10.673  -1.603   0.029  1.00  0.00           H  
HETATM   62  H37 UNL     1     -11.259  -0.257  -0.915  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6   35   36
CONECT    6    7    7   37
CONECT    7    8   38
CONECT    8    9   39   40
CONECT    9   10   10   41
CONECT   10   11   42
CONECT   11   12   43   44
CONECT   12   13   13   45
CONECT   13   14   46
CONECT   14   15   47   48
CONECT   15   16   16   49
CONECT   16   17   50
CONECT   17   18   51   52
CONECT   18   19   53   54
CONECT   19   20   55   56
CONECT   20   21   21   22
CONECT   22   23
CONECT   23   24   57   58
CONECT   24   25   59   60
CONECT   25   61   62
END

HMDB0013655
     RDKit          3D
O-Arachidonoyl Ethanolamine
 62 61  0  0  0  0  0  0  0  0999 V2000
    8.3501   -0.1709   -1.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9068   -0.3585   -1.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7816   -0.6657    0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3175   -0.8487    0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1863   -1.1671    1.8678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7183   -0.0749    2.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9966    0.5821    3.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5659    0.3075    3.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8282    1.5516    3.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8811    1.6352    2.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4602    0.4477    1.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6190    0.7056    0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5866    0.6177   -0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7883    0.2737   -0.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2046   -0.9558   -0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2067   -0.9827   -1.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0781    0.1515   -1.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5328   -0.2038   -1.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3531    1.0116   -1.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7932    0.8156   -1.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0962    0.9420   -0.3069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7531    0.5190   -2.4308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1126    0.3275   -2.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2709   -0.8338   -1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6605   -1.0877   -0.8760 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5353   -0.4875   -2.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9824   -0.7587   -1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6066    0.8992   -1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5151   -1.2009   -2.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2777    0.5303   -1.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2832   -1.6408    0.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2894    0.0938    0.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7611    0.0862    0.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8772   -1.7115   -0.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1746   -1.4954    2.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8888   -2.0578    1.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8019    0.1998    2.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4850    1.4044    4.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2002   -0.6125    3.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5002    0.1883    4.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1462    2.4453    4.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3716    2.6103    2.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3769    0.3533    2.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8970   -0.5018    2.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5906    0.9764   -0.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7710    0.8255   -1.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9535    0.0127    1.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4395    1.1396   -0.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5791   -1.8370   -0.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4338   -1.9363   -2.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8556    1.0582   -1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1025    0.3760   -3.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5217   -0.4071   -0.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7958   -1.0840   -2.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2537    1.2233   -2.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9935    1.8660   -1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7224    0.1509   -3.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5424    1.2590   -1.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7555   -0.6295   -0.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7987   -1.7258   -1.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6728   -1.6032    0.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2595   -0.2574   -0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 23 57  1  0
 23 58  1  0
 24 59  1  0
 24 60  1  0
 25 61  1  0
 25 62  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Arachidonic acid-(2-aminoethyl)-ester	HMDB
O-AEA	HMDB
Virodhamine	HMDB
O-Arachidonyl ethanol amine	MeSH, HMDB
O-Arachidonoyl ethanolamine	MeSH

Chemical Formula

C₂₂H₃₇NO₂

Average Molecular Weight

347.5347

Monoisotopic Molecular Weight

347.282429433

IUPAC Name

2-aminoethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate

Traditional Name

virodhamine

CAS Registry Number

443129-35-9

SMILES

CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCCN

InChI Identifier

InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)25-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21,23H2,1H3/b7-6-,10-9-,13-12-,16-15-

InChI Key

DLHLOYYQQGSXCC-DOFZRALJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Other Fatty Acyls (LMFA00000014 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0013655)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013655)

Source

Endogenous

Endogenous (HMDB: HMDB0013655)

Animal

Animal (HMDB: HMDB0013655)

Exogenous

Food

Food (HMDB: HMDB0013655)

Exogenous (HMDB: HMDB0013655)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0013655)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0013655)

Lipid metabolism pathway (HMDB: HMDB0013655)

Cellular process

Cell signaling (HMDB: HMDB0013655)

Biochemical process

Lipid transport (HMDB: HMDB0013655)

Role

Biological role

Energy source (HMDB: HMDB0013655)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013655)

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	0.00013 g/L	ALOGPS
logP	6.27	ALOGPS
logP	5.94	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Basic)	9.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	112.67 m³·mol⁻¹	ChemAxon
Polarizability	42.97 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]+	197.139	31661259
DarkChem	[M-H]-	196.731	31661259
DeepCCS	[M+H]+	191.643	30932474
DeepCCS	[M-H]-	189.285	30932474
DeepCCS	[M-2H]-	222.469	30932474
DeepCCS	[M+Na]+	197.92	30932474
AllCCS	[M+H]+	193.8	32859911
AllCCS	[M+H-H2O]+	191.2	32859911
AllCCS	[M+NH4]+	196.2	32859911
AllCCS	[M+Na]+	196.9	32859911
AllCCS	[M-H]-	192.1	32859911
AllCCS	[M+Na-2H]-	194.4	32859911
AllCCS	[M+HCOO]-	197.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.16 minutes	32390414
Predicted by Siyang on May 30, 2022	22.5254 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.66 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2911.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	403.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	214.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	285.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	646.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1059.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	582.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	194.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2168.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	722.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1774.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	775.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	502.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	360.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	395.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-Arachidonoyl Ethanolamine	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCCN	3095.1	Standard polar	33892256
O-Arachidonoyl Ethanolamine	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCCN	2378.1	Standard non polar	33892256
O-Arachidonoyl Ethanolamine	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCCN	2653.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
O-Arachidonoyl Ethanolamine,1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN[Si](C)(C)C	2774.4	Semi standard non polar	33892256
O-Arachidonoyl Ethanolamine,1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN[Si](C)(C)C	2737.3	Standard non polar	33892256
O-Arachidonoyl Ethanolamine,1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN[Si](C)(C)C	3064.0	Standard polar	33892256
O-Arachidonoyl Ethanolamine,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN([Si](C)(C)C)[Si](C)(C)C	2978.6	Semi standard non polar	33892256
O-Arachidonoyl Ethanolamine,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN([Si](C)(C)C)[Si](C)(C)C	2895.5	Standard non polar	33892256
O-Arachidonoyl Ethanolamine,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN([Si](C)(C)C)[Si](C)(C)C	2898.3	Standard polar	33892256
O-Arachidonoyl Ethanolamine,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN[Si](C)(C)C(C)(C)C	2971.9	Semi standard non polar	33892256
O-Arachidonoyl Ethanolamine,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN[Si](C)(C)C(C)(C)C	2937.1	Standard non polar	33892256
O-Arachidonoyl Ethanolamine,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN[Si](C)(C)C(C)(C)C	3072.9	Standard polar	33892256
O-Arachidonoyl Ethanolamine,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3412.6	Semi standard non polar	33892256
O-Arachidonoyl Ethanolamine,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3189.2	Standard non polar	33892256
O-Arachidonoyl Ethanolamine,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2938.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - O-Arachidonoyl Ethanolamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9160000000-e4d605556a74c32850b5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Arachidonoyl Ethanolamine 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 - O-Arachidonoyl Ethanolamine 10V, Positive-QTOF	splash10-0005-6159000000-99134b0a76bda27146bc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 20V, Positive-QTOF	splash10-0006-9241000000-24b121d519022021b041	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 40V, Positive-QTOF	splash10-0006-9230000000-34e0714a863ac0a11fe4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 10V, Negative-QTOF	splash10-000b-2049000000-44ec5ce62678fce7c991	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 20V, Negative-QTOF	splash10-000j-5097000000-226c63be9164349ed9bf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 40V, Negative-QTOF	splash10-0006-9030000000-f393ed4f36b8e090cc1a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 10V, Positive-QTOF	splash10-0002-4329000000-2afbe38e34d21b7d29ed	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 20V, Positive-QTOF	splash10-01po-9412000000-2d595dbad447acf1e266	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 40V, Positive-QTOF	splash10-00l6-9500000000-37b7a889796f7361f97e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 10V, Negative-QTOF	splash10-0002-0029000000-6d820b2c37cd6bf13b7e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 20V, Negative-QTOF	splash10-0f7a-5189000000-c237f01fc5e28353b369	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 40V, Negative-QTOF	splash10-0uk9-9385000000-ece22a403f9d3abaf5f1	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029625

KNApSAcK ID

Not Available

Chemspider ID

4650158

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Virodhamine

METLIN ID

Not Available

PubChem Compound

5712057

PDB ID

Not Available

ChEBI ID

418207

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for O-Arachidonoyl Ethanolamine (HMDB0013655)

MOL for HMDB0013655 (O-Arachidonoyl Ethanolamine)

3D MOL for HMDB0013655 (O-Arachidonoyl Ethanolamine)

3D SDF for HMDB0013655 (O-Arachidonoyl Ethanolamine)

3D-SDF for HMDB0013655 (O-Arachidonoyl Ethanolamine)

PDB for HMDB0013655 (O-Arachidonoyl Ethanolamine)

3D PDB for HMDB0013655 (O-Arachidonoyl Ethanolamine)

SMILES for HMDB0013655 (O-Arachidonoyl Ethanolamine)

INCHI for HMDB0013655 (O-Arachidonoyl Ethanolamine)

Structure for HMDB0013655 (O-Arachidonoyl Ethanolamine)

3D Structure for HMDB0013655 (O-Arachidonoyl Ethanolamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra