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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2011-07-12 10:28:56 UTC

Update Date

2022-03-07 02:51:34 UTC

HMDB ID

HMDB0013659

Secondary Accession Numbers

HMDB13659

Metabolite Identification

Common Name

(±)8(9)-EET Ethanolamide

Description

(±)8(9)-EET ethanolamide is a cytochrome P450 (CYP450) metabolite of arachidonoyl ethanolamide (AEA), although specific stereochemistry rather than a racemic mixture would likely ensue from enzymatic metabolism (PMID: 17272674 ). AEA is an endogenous lipid neurotransmitter with cannabingeric activity, binding to both the central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors (PMID: 8395053 , 16078824 ). Fatty acid amide hydrolase (FAAH) is the enzyme responsible for the hydrolysis and inactivation of AEA (PMID: 12052036 ). Metabolism of AEA by COX-2, lipoxygenases, and CYP450 enzymes has also been documented (PMID: 12052037 , 17272674 ). Human liver microsomes metabolize AEA to 5,6-, 8,9-, 11,12-, and 14,15-EET ethanolamides in a time and protein concentration dependent manner (PMID: 17272674 ). (±)8(9)-EET reduces glomerular filtration rate through cyclooxygenase dependent preglomerular vasoconstriction (PMID: 1928373 ). The physiological actions of (±)8(9)-EET ethanolamide have not been examined.

Structure

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


  Mrv0541 02271200292D          

 26 26  0  0  0  0            999 V2000
    3.2890  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0035  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7179  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4324  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1469  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8613  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5758  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2903  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0048  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7193  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4337  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1482  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9732  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5771  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2917  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0061  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7206  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4351  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1496  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8640  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5785  -10.6879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8640  -11.9255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5607  -11.8149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2930  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0075  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7220  -11.1004    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  1  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 12  1  0  0  0  0
 13 23  1  0  0  0  0
 24 21  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
M  END

HMDB0013659
     RDKit          3D
(±)8(9)-EET Ethanolamide
 63 63  0  0  0  0  0  0  0  0999 V2000
    8.1061   -1.4382    2.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5570   -0.0991    2.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3670    0.2998    1.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7896    0.4020    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5379    0.8111   -0.6140 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1183    2.1001   -0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9501    2.2915    0.4654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9172    1.2512    0.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7422    1.7223   -0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209    1.0927   -1.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7624   -0.1560   -1.6481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6583   -1.2205   -1.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5154   -0.8817   -2.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6378   -0.7835   -0.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5267   -1.8209   -0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9365   -2.8433   -1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1778   -3.1084   -1.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3573   -2.4036   -0.9642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1593   -1.7096   -2.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3582   -0.9865   -1.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0318    0.0774   -0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8375    0.3650   -0.2549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0497    0.8199    0.0984 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7384    1.8719    1.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0389    2.4645    1.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8240    3.4838    2.4621 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3015   -2.1441    1.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8016   -1.2422    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6971   -1.9017    2.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3129    0.6963    2.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2138   -0.1757    3.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5328   -0.4440    1.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9855    1.2532    2.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1231   -0.6121   -0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5733    1.1558    0.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8968    0.8985   -1.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8713   -0.0285   -0.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8737    2.9171   -0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6906    3.2809    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6032    1.2965    1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2178    0.2262    0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3011    2.6736    0.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3163    1.4840   -1.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112   -0.5129   -1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8981   -0.0323   -2.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9571   -2.2739   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6885    0.2106   -0.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3238   -1.3158    0.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929   -2.3032    0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1109   -3.4131   -1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103   -3.9136   -2.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1823   -1.8296   -0.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0461   -3.2517   -0.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5423   -2.4876   -2.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5277   -1.0340   -2.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8756   -0.5307   -2.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0105   -1.7272   -0.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0530    0.5792   -0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1319    1.4767    1.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1693    2.6535    0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5994    1.6579    2.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5864    2.8200    0.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3655    4.2918    2.2654 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  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 14 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 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


  Mrv0541 02271200292D          

 26 26  0  0  0  0            999 V2000
    3.2890  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0035  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7179  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4324  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1469  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8613  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5758  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2903  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0048  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7193  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4337  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1482  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9732  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5771  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2917  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0061  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7206  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4351  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1496  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8640  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5785  -10.6879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8640  -11.9255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5607  -11.8149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2930  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0075  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7220  -11.1004    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  1  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 12  1  0  0  0  0
 13 23  1  0  0  0  0
 24 21  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013659

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(=O)NCCO

> <INCHI_IDENTIFIER>
InChI=1S/C22H37NO3/c1-2-3-4-5-6-7-8-9-12-15-20-21(26-20)16-13-10-11-14-17-22(25)23-18-19-24/h6-7,9-10,12-13,20-21,24H,2-5,8,11,14-19H2,1H3,(H,23,25)/b7-6-,12-9-,13-10-

> <INCHI_KEY>
BXHPMUQFGGSDAK-TYAUOURKSA-N

> <FORMULA>
C22H37NO3

> <MOLECULAR_WEIGHT>
363.5341

> <EXACT_MASS>
363.277344055

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
44.214987275229404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-N-(2-hydroxyethyl)-7-{3-[(2Z,5Z)-undeca-2,5-dien-1-yl]oxiran-2-yl}hept-5-enamide

> <ALOGPS_LOGP>
5.42

> <JCHEM_LOGP>
4.375805346

> <ALOGPS_LOGS>
-5.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.18168867576705

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.333100730572678

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3385882153718186

> <JCHEM_POLAR_SURFACE_AREA>
61.86

> <JCHEM_REFRACTIVITY>
111.36949999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.51e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8(9)-EpETrE-EA

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013659
     RDKit          3D
(±)8(9)-EET Ethanolamide
 63 63  0  0  0  0  0  0  0  0999 V2000
    8.1061   -1.4382    2.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5570   -0.0991    2.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3670    0.2998    1.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7896    0.4020    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5379    0.8111   -0.6140 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1183    2.1001   -0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9501    2.2915    0.4654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9172    1.2512    0.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7422    1.7223   -0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209    1.0927   -1.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7624   -0.1560   -1.6481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6583   -1.2205   -1.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5154   -0.8817   -2.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6378   -0.7835   -0.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5267   -1.8209   -0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9365   -2.8433   -1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1778   -3.1084   -1.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3573   -2.4036   -0.9642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1593   -1.7096   -2.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3582   -0.9865   -1.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0318    0.0774   -0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8375    0.3650   -0.2549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0497    0.8199    0.0984 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7384    1.8719    1.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0389    2.4645    1.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8240    3.4838    2.4621 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3015   -2.1441    1.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8016   -1.2422    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6971   -1.9017    2.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3129    0.6963    2.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2138   -0.1757    3.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5328   -0.4440    1.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9855    1.2532    2.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1231   -0.6121   -0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5733    1.1558    0.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8968    0.8985   -1.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8713   -0.0285   -0.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8737    2.9171   -0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6906    3.2809    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6032    1.2965    1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2178    0.2262    0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3011    2.6736    0.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3163    1.4840   -1.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112   -0.5129   -1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8981   -0.0323   -2.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9571   -2.2739   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6885    0.2106   -0.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3238   -1.3158    0.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929   -2.3032    0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1109   -3.4131   -1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103   -3.9136   -2.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1823   -1.8296   -0.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0461   -3.2517   -0.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5423   -2.4876   -2.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5277   -1.0340   -2.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8756   -0.5307   -2.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0105   -1.7272   -0.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0530    0.5792   -0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1319    1.4767    1.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1693    2.6535    0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5994    1.6579    2.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5864    2.8200    0.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3655    4.2918    2.2654 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  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 14 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 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                                 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       6.139 -19.951   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.473 -20.721   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.807 -19.951   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.140 -20.721   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.474 -19.951   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.808 -20.721   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.141 -20.721   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.475 -19.951   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.809 -20.721   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.143 -20.721   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.476 -19.951   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.810 -20.721   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.350 -20.721   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.477 -19.951   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.811 -20.721   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.145 -20.721   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.478 -19.951   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.812 -20.721   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.146 -19.951   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      31.479 -20.721   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      32.813 -19.951   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0      31.479 -22.261   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      21.580 -22.054   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      34.147 -20.721   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      35.481 -19.951   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      36.814 -20.721   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   23                                                  
CONECT   13   12   14   23                                                  
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   24                                                       
CONECT   22   20                                                            
CONECT   23   12   13                                                       
CONECT   24   21   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

COMPND    HMDB0013659
HETATM    1  C1  UNL     1       8.106  -1.438   2.062  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.557  -0.099   2.504  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.367   0.300   1.664  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.790   0.402   0.193  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.538   0.811  -0.614  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.118   2.100  -0.065  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.950   2.292   0.465  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.917   1.251   0.578  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.742   1.722  -0.145  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.221   1.093  -1.146  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.762  -0.156  -1.648  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.658  -1.220  -1.519  1.00  0.00           C  
HETATM   13  O1  UNL     1      -0.515  -0.882  -2.268  1.00  0.00           O  
HETATM   14  C13 UNL     1      -0.638  -0.783  -0.897  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.527  -1.821  -0.244  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.937  -2.843  -1.208  1.00  0.00           C  
HETATM   17  C16 UNL     1      -3.178  -3.108  -1.532  1.00  0.00           C  
HETATM   18  C17 UNL     1      -4.357  -2.404  -0.964  1.00  0.00           C  
HETATM   19  C18 UNL     1      -5.159  -1.710  -2.049  1.00  0.00           C  
HETATM   20  C19 UNL     1      -6.358  -0.986  -1.501  1.00  0.00           C  
HETATM   21  C20 UNL     1      -6.032   0.077  -0.541  1.00  0.00           C  
HETATM   22  O2  UNL     1      -4.837   0.365  -0.255  1.00  0.00           O  
HETATM   23  N1  UNL     1      -7.050   0.820   0.098  1.00  0.00           N  
HETATM   24  C21 UNL     1      -6.738   1.872   1.047  1.00  0.00           C  
HETATM   25  C22 UNL     1      -8.039   2.464   1.545  1.00  0.00           C  
HETATM   26  O3  UNL     1      -7.824   3.484   2.462  1.00  0.00           O  
HETATM   27  H1  UNL     1       7.302  -2.144   1.787  1.00  0.00           H  
HETATM   28  H2  UNL     1       8.802  -1.242   1.208  1.00  0.00           H  
HETATM   29  H3  UNL     1       8.697  -1.902   2.872  1.00  0.00           H  
HETATM   30  H4  UNL     1       8.313   0.696   2.393  1.00  0.00           H  
HETATM   31  H5  UNL     1       7.214  -0.176   3.552  1.00  0.00           H  
HETATM   32  H6  UNL     1       5.533  -0.444   1.770  1.00  0.00           H  
HETATM   33  H7  UNL     1       5.985   1.253   2.040  1.00  0.00           H  
HETATM   34  H8  UNL     1       7.123  -0.612  -0.096  1.00  0.00           H  
HETATM   35  H9  UNL     1       7.573   1.156   0.131  1.00  0.00           H  
HETATM   36  H10 UNL     1       5.897   0.899  -1.683  1.00  0.00           H  
HETATM   37  H11 UNL     1       4.871  -0.029  -0.534  1.00  0.00           H  
HETATM   38  H12 UNL     1       5.874   2.917  -0.132  1.00  0.00           H  
HETATM   39  H13 UNL     1       3.691   3.281   0.863  1.00  0.00           H  
HETATM   40  H14 UNL     1       2.603   1.296   1.693  1.00  0.00           H  
HETATM   41  H15 UNL     1       3.218   0.226   0.455  1.00  0.00           H  
HETATM   42  H16 UNL     1       1.301   2.674   0.212  1.00  0.00           H  
HETATM   43  H17 UNL     1       0.316   1.484  -1.680  1.00  0.00           H  
HETATM   44  H18 UNL     1       2.711  -0.513  -1.299  1.00  0.00           H  
HETATM   45  H19 UNL     1       1.898  -0.032  -2.775  1.00  0.00           H  
HETATM   46  H20 UNL     1       0.957  -2.274  -1.513  1.00  0.00           H  
HETATM   47  H21 UNL     1      -0.688   0.211  -0.403  1.00  0.00           H  
HETATM   48  H22 UNL     1      -2.324  -1.316   0.313  1.00  0.00           H  
HETATM   49  H23 UNL     1      -0.893  -2.303   0.563  1.00  0.00           H  
HETATM   50  H24 UNL     1      -1.111  -3.413  -1.675  1.00  0.00           H  
HETATM   51  H25 UNL     1      -3.310  -3.914  -2.278  1.00  0.00           H  
HETATM   52  H26 UNL     1      -4.182  -1.830  -0.070  1.00  0.00           H  
HETATM   53  H27 UNL     1      -5.046  -3.252  -0.633  1.00  0.00           H  
HETATM   54  H28 UNL     1      -5.542  -2.488  -2.743  1.00  0.00           H  
HETATM   55  H29 UNL     1      -4.528  -1.034  -2.660  1.00  0.00           H  
HETATM   56  H30 UNL     1      -6.876  -0.531  -2.387  1.00  0.00           H  
HETATM   57  H31 UNL     1      -7.011  -1.727  -0.995  1.00  0.00           H  
HETATM   58  H32 UNL     1      -8.053   0.579  -0.141  1.00  0.00           H  
HETATM   59  H33 UNL     1      -6.132   1.477   1.901  1.00  0.00           H  
HETATM   60  H34 UNL     1      -6.169   2.653   0.525  1.00  0.00           H  
HETATM   61  H35 UNL     1      -8.599   1.658   2.072  1.00  0.00           H  
HETATM   62  H36 UNL     1      -8.586   2.820   0.643  1.00  0.00           H  
HETATM   63  H37 UNL     1      -8.365   4.292   2.265  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   30   31
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6   36   37
CONECT    6    7    7   38
CONECT    7    8   39
CONECT    8    9   40   41
CONECT    9   10   10   42
CONECT   10   11   43
CONECT   11   12   44   45
CONECT   12   13   14   46
CONECT   13   14
CONECT   14   15   47
CONECT   15   16   48   49
CONECT   16   17   17   50
CONECT   17   18   51
CONECT   18   19   52   53
CONECT   19   20   54   55
CONECT   20   21   56   57
CONECT   21   22   22   23
CONECT   23   24   58
CONECT   24   25   59   60
CONECT   25   26   61   62
CONECT   26   63
END

HMDB0013659
     RDKit          3D
(±)8(9)-EET Ethanolamide
 63 63  0  0  0  0  0  0  0  0999 V2000
    8.1061   -1.4382    2.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5570   -0.0991    2.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3670    0.2998    1.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7896    0.4020    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5379    0.8111   -0.6140 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1183    2.1001   -0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9501    2.2915    0.4654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9172    1.2512    0.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7422    1.7223   -0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209    1.0927   -1.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7624   -0.1560   -1.6481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6583   -1.2205   -1.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5154   -0.8817   -2.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6378   -0.7835   -0.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5267   -1.8209   -0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9365   -2.8433   -1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1778   -3.1084   -1.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3573   -2.4036   -0.9642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1593   -1.7096   -2.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3582   -0.9865   -1.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0318    0.0774   -0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8375    0.3650   -0.2549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0497    0.8199    0.0984 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7384    1.8719    1.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0389    2.4645    1.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8240    3.4838    2.4621 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3015   -2.1441    1.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8016   -1.2422    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6971   -1.9017    2.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3129    0.6963    2.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2138   -0.1757    3.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5328   -0.4440    1.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9855    1.2532    2.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1231   -0.6121   -0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5733    1.1558    0.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8968    0.8985   -1.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8713   -0.0285   -0.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8737    2.9171   -0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6906    3.2809    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6032    1.2965    1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2178    0.2262    0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3011    2.6736    0.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3163    1.4840   -1.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112   -0.5129   -1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8981   -0.0323   -2.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9571   -2.2739   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6885    0.2106   -0.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3238   -1.3158    0.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929   -2.3032    0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1109   -3.4131   -1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103   -3.9136   -2.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1823   -1.8296   -0.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0461   -3.2517   -0.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5423   -2.4876   -2.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5277   -1.0340   -2.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8756   -0.5307   -2.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0105   -1.7272   -0.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0530    0.5792   -0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1319    1.4767    1.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1693    2.6535    0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5994    1.6579    2.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5864    2.8200    0.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3655    4.2918    2.2654 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  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 14 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 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
8(9)-EET-ea	ChEBI
8(9)-EpETrE-ea	ChEBI
8,9-EET-ea	ChEBI
N-(8,9-Epoxy-5Z,11Z,14Z-eicosatrienoyl)-ethanolamine	ChEBI
N-(8,9-Epoxy-5Z,11Z,14Z-icosatrienoyl)ethanolamine	ChEBI
(+/-)8(9)-epetre ethanolamide	HMDB

Chemical Formula

C₂₂H₃₇NO₃

Average Molecular Weight

363.5341

Monoisotopic Molecular Weight

363.277344055

IUPAC Name

(5Z)-N-(2-hydroxyethyl)-7-{3-[(2Z,5Z)-undeca-2,5-dien-1-yl]oxiran-2-yl}hept-5-enamide

Traditional Name

8(9)-EpETrE-EA

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(=O)NCCO

InChI Identifier

InChI=1S/C22H37NO3/c1-2-3-4-5-6-7-8-9-12-15-20-21(26-20)16-13-10-11-14-17-22(25)23-18-19-24/h6-7,9-10,12-13,20-21,24H,2-5,8,11,14-19H2,1H3,(H,23,25)/b7-6-,12-9-,13-10-

InChI Key

BXHPMUQFGGSDAK-TYAUOURKSA-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
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Organopnictogen compound
Alcohol
Organic oxygen compound
Organooxygen compound
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acyl ethanolamines (endocannabinoids) (LMFA08040033 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0013659)

Cellular substructure

Extracellular (HMDB: HMDB0013659)
Membrane (HMDB: HMDB0013659)

Source

Endogenous

Endogenous (HMDB: HMDB0013659)

Exogenous

Food

Food (HMDB: HMDB0013659)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0013659)

Role

Biological role

Energy source (HMDB: HMDB0013659)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013659)

Emulsifier (HMDB: HMDB0013659)

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	0.00085 g/L	ALOGPS
logP	5.42	ALOGPS
logP	4.38	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	15.33	ChemAxon
pKa (Strongest Basic)	-0.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	61.86 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	111.37 m³·mol⁻¹	ChemAxon
Polarizability	44.21 Å³	ChemAxon
Number of Rings	1	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]+	195.751	31661259
DarkChem	[M-H]-	193.713	31661259
DeepCCS	[M+H]+	192.204	30932474
DeepCCS	[M-H]-	189.846	30932474
DeepCCS	[M-2H]-	222.878	30932474
DeepCCS	[M+Na]+	198.376	30932474
AllCCS	[M+H]+	198.8	32859911
AllCCS	[M+H-H2O]+	196.3	32859911
AllCCS	[M+NH4]+	201.1	32859911
AllCCS	[M+Na]+	201.7	32859911
AllCCS	[M-H]-	196.2	32859911
AllCCS	[M+Na-2H]-	198.4	32859911
AllCCS	[M+HCOO]-	201.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(??)8(9)-EET Ethanolamide	CCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(=O)NCCO	3254.4	Standard polar	33892256
(??)8(9)-EET Ethanolamide	CCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(=O)NCCO	2678.0	Standard non polar	33892256
(??)8(9)-EET Ethanolamide	CCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(=O)NCCO	3011.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(??)8(9)-EET Ethanolamide,1TMS,isomer #1	CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)NCCO[Si](C)(C)C	2985.7	Semi standard non polar	33892256
(??)8(9)-EET Ethanolamide,1TMS,isomer #2	CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)N(CCO)[Si](C)(C)C	2911.3	Semi standard non polar	33892256
(±)8(9)-EET Ethanolamide,2TMS,isomer #1	CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2940.6	Semi standard non polar	33892256
(±)8(9)-EET Ethanolamide,2TMS,isomer #1	CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	3020.2	Standard non polar	33892256
(±)8(9)-EET Ethanolamide,2TMS,isomer #1	CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	3097.0	Standard polar	33892256
(??)8(9)-EET Ethanolamide,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)NCCO[Si](C)(C)C(C)(C)C	3220.9	Semi standard non polar	33892256
(??)8(9)-EET Ethanolamide,1TBDMS,isomer #2	CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C	3139.1	Semi standard non polar	33892256
(±)8(9)-EET Ethanolamide,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3430.2	Semi standard non polar	33892256
(±)8(9)-EET Ethanolamide,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3367.9	Standard non polar	33892256
(±)8(9)-EET Ethanolamide,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3151.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (±)8(9)-EET Ethanolamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6t-7975000000-138caba1cc10d88b3acb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)8(9)-EET Ethanolamide GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-8895200000-ff0d605a4780f0fe8a9b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)8(9)-EET 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 - (±)8(9)-EET Ethanolamide 10V, Positive-QTOF	splash10-03di-4219000000-6a4153a00d35175f07cc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 20V, Positive-QTOF	splash10-03di-9501000000-49546729e6f1fc39fbde	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 40V, Positive-QTOF	splash10-03di-9300000000-e83b610335b0f604ffa2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 10V, Negative-QTOF	splash10-03di-0209000000-ecb21063dfd7ef100dad	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 20V, Negative-QTOF	splash10-03dl-5309000000-6e6597f4aa6f9be887a1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 40V, Negative-QTOF	splash10-01ox-9400000000-a6384c85eb3f6a786050	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 10V, Positive-QTOF	splash10-03di-5209000000-53d5fe289aac0a214cf6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 20V, Positive-QTOF	splash10-03dm-9103000000-2718f725d05698a31a6a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 40V, Positive-QTOF	splash10-000x-9100000000-3f90e9cfac2f10988867	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 10V, Negative-QTOF	splash10-03di-0009000000-98c48b1fa4d3ad780022	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 20V, Negative-QTOF	splash10-03dl-2129000000-908411b9c58743953841	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 40V, Negative-QTOF	splash10-0596-9202000000-f292ca66393a75a3a56a	2021-09-22	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

FDB029629

KNApSAcK ID

Not Available

Chemspider ID

17220861

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16061182

PDB ID

Not Available

ChEBI ID

136989

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

Kozak KR, Marnett LJ: Oxidative metabolism of endocannabinoids. Prostaglandins Leukot Essent Fatty Acids. 2002 Feb-Mar;66(2-3):211-20. [PubMed:12052037 ]
Snider NT, Kornilov AM, Kent UM, Hollenberg PF: Anandamide metabolism by human liver and kidney microsomal cytochrome p450 enzymes to form hydroxyeicosatetraenoic and epoxyeicosatrienoic acid ethanolamides. J Pharmacol Exp Ther. 2007 May;321(2):590-7. Epub 2007 Feb 1. [PubMed:17272674 ]
Felder CC, Briley EM, Axelrod J, Simpson JT, Mackie K, Devane WA: Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc Natl Acad Sci U S A. 1993 Aug 15;90(16):7656-60. [PubMed:8395053 ]
Lambert DM, Fowler CJ: The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications. J Med Chem. 2005 Aug 11;48(16):5059-87. [PubMed:16078824 ]
Deutsch DG, Ueda N, Yamamoto S: The fatty acid amide hydrolase (FAAH). Prostaglandins Leukot Essent Fatty Acids. 2002 Feb-Mar;66(2-3):201-10. [PubMed:12052036 ]
Katoh T, Takahashi K, Capdevila J, Karara A, Falck JR, Jacobson HR, Badr KF: Glomerular stereospecific synthesis and hemodynamic actions of 8,9-epoxyeicosatrienoic acid in rat kidney. Am J Physiol. 1991 Oct;261(4 Pt 2):F578-86. [PubMed:1928373 ]

Showing metabocard for (±)8(9)-EET Ethanolamide (HMDB0013659)

MOL for HMDB0013659 ((±)8(9)-EET Ethanolamide)

3D MOL for HMDB0013659 ((±)8(9)-EET Ethanolamide)

3D SDF for HMDB0013659 ((±)8(9)-EET Ethanolamide)

3D-SDF for HMDB0013659 ((±)8(9)-EET Ethanolamide)

PDB for HMDB0013659 ((±)8(9)-EET Ethanolamide)

3D PDB for HMDB0013659 ((±)8(9)-EET Ethanolamide)

SMILES for HMDB0013659 ((±)8(9)-EET Ethanolamide)

INCHI for HMDB0013659 ((±)8(9)-EET Ethanolamide)

Structure for HMDB0013659 ((±)8(9)-EET Ethanolamide)

3D Structure for HMDB0013659 ((±)8(9)-EET Ethanolamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra