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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2011-07-07 10:24:13 UTC

Update Date

2022-03-07 02:51:34 UTC

HMDB ID

HMDB0013652

Secondary Accession Numbers

HMDB13652

Metabolite Identification

Common Name

(±)11(12)-EET Ethanolamide

Description

(±)11(12)-EET ethanolamide is a potential cytochrome P450 (CYP450) metabolite of arachidonoyl ethanolamide (AEA; anandamide), although specific stereochemistry rather than a racemic mixture would likely ensue from enzymatic metabolism. AEA is an endogenous lipid neurotransmitter with cannibingeric 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 cyclooxygenase-2, leading to formation of prostaglandin ethanolamides, and by lipoxygenases has also been documented (PMID: 12052037 ). CYP450 metabolism of AEA may be particularly relevant under conditions of FAAH inhibition. Evidence for the formation of 11(12)-EET ethanolamide in vivo has not been documented.

Structure

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


  Mrv0541 02271200292D          

 26 26  0  0  0  0            999 V2000
   17.6251   -4.0087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4501   -4.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8626   -4.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6877   -4.7231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1002   -5.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9252   -5.4376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6877   -6.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1002   -6.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6877   -7.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1002   -8.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6877   -9.0100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8626   -9.0100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4501   -9.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6251   -9.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2126   -9.0100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3876   -9.0100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6732   -9.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2607  -10.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4356  -10.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0231  -10.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6732   -8.5975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4356  -11.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0231  -12.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1981  -12.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7856  -12.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9606  -12.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  2  0  0  0  0
 21 16  1  0  0  0  0
 21 17  1  0  0  0  0
 22 20  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
M  END

HMDB0013652
     RDKit          3D
(±)11(12)-EET Ethanolamide
 63 63  0  0  0  0  0  0  0  0999 V2000
  -10.4499   -0.3874   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1300    0.3263   -0.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3534   -0.4606   -1.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0264    0.1418   -1.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1299    0.2240   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8981   -1.1064    0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7206   -1.6104    0.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3829   -1.1614    0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9791    0.1765   -0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2253    1.3307    0.5436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9114    0.9432    0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8890    1.7516   -0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1081    0.9016   -1.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1915    0.7120   -1.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0663    1.3885   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7838    0.3301    0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0738    0.2232    0.6745 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9891    1.1316   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8973    1.8485    0.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7507    0.9601    1.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6948    0.1915    0.8890 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8078    0.4195   -0.3363 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5025   -0.8315    1.4579 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4345   -1.6493    0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8065   -2.5308   -0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1497   -1.8419   -1.2489 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1677    0.3923    0.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2647   -1.1573    0.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7441   -0.8181   -0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6289    0.3994    0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2579    1.3479   -0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9518   -0.4275   -2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2892   -1.5441   -1.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5372   -0.4587   -2.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1841    1.1572   -1.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2060    0.6298   -0.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6763    0.8740    0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8228   -1.7241    0.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7991   -2.6806    0.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952   -1.3561    1.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7837   -1.8967   -0.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415    0.3142   -1.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5627    0.5081    1.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4465    2.5220   -0.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3107    2.3296    0.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6505    0.3365   -1.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6653    0.0426   -1.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6952    2.0900   -0.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4759    1.9372    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1743   -0.3943    1.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5066   -0.6003    1.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6332    0.4711   -0.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5179    1.8185   -0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5841    2.4712    0.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2673    2.5347    1.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2825    1.5648    2.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1555    0.2026    2.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3729   -0.9808    2.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9771   -2.2995    1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1660   -0.9936    0.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6360   -3.1245   -0.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1020   -3.2402    0.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7647   -1.6685   -1.9969 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  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
 11  9  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
 11 43  1  0
 12 44  1  0
 12 45  1  0
 13 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
   17.6251   -4.0087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4501   -4.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8626   -4.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6877   -4.7231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1002   -5.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9252   -5.4376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6877   -6.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1002   -6.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6877   -7.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1002   -8.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6877   -9.0100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8626   -9.0100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4501   -9.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6251   -9.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2126   -9.0100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3876   -9.0100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6732   -9.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2607  -10.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4356  -10.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0231  -10.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6732   -8.5975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4356  -11.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0231  -12.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1981  -12.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7856  -12.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9606  -12.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  2  0  0  0  0
 21 16  1  0  0  0  0
 21 17  1  0  0  0  0
 22 20  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013652

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H37NO3/c1-2-3-4-5-9-12-15-20-21(26-20)16-13-10-7-6-8-11-14-17-22(25)23-18-19-24/h6,8-10,12-13,20-21,24H,2-5,7,11,14-19H2,1H3,(H,23,25)/b8-6-,12-9-,13-10-

> <INCHI_KEY>
TYRRSRADDAROSO-KROJNAHFSA-N

> <FORMULA>
C22H37NO3

> <MOLECULAR_WEIGHT>
363.5341

> <EXACT_MASS>
363.277344055

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
44.04780659593334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z)-N-(2-hydroxyethyl)-10-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienamide

> <ALOGPS_LOGP>
5.43

> <JCHEM_LOGP>
4.375805346

> <ALOGPS_LOGS>
-5.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.375825066097118

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.435299736387666

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3385882709143132

> <JCHEM_POLAR_SURFACE_AREA>
61.86

> <JCHEM_REFRACTIVITY>
111.3695

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.84e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5Z,8Z)-N-(2-hydroxyethyl)-10-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013652
     RDKit          3D
(±)11(12)-EET Ethanolamide
 63 63  0  0  0  0  0  0  0  0999 V2000
  -10.4499   -0.3874   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1300    0.3263   -0.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3534   -0.4606   -1.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0264    0.1418   -1.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1299    0.2240   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8981   -1.1064    0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7206   -1.6104    0.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3829   -1.1614    0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9791    0.1765   -0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2253    1.3307    0.5436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9114    0.9432    0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8890    1.7516   -0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1081    0.9016   -1.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1915    0.7120   -1.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0663    1.3885   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7838    0.3301    0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0738    0.2232    0.6745 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9891    1.1316   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8973    1.8485    0.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7507    0.9601    1.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6948    0.1915    0.8890 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8078    0.4195   -0.3363 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5025   -0.8315    1.4579 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4345   -1.6493    0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8065   -2.5308   -0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1497   -1.8419   -1.2489 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1677    0.3923    0.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2647   -1.1573    0.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7441   -0.8181   -0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6289    0.3994    0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2579    1.3479   -0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9518   -0.4275   -2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2892   -1.5441   -1.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5372   -0.4587   -2.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1841    1.1572   -1.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2060    0.6298   -0.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6763    0.8740    0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8228   -1.7241    0.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7991   -2.6806    0.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952   -1.3561    1.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7837   -1.8967   -0.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415    0.3142   -1.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5627    0.5081    1.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4465    2.5220   -0.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3107    2.3296    0.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6505    0.3365   -1.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6653    0.0426   -1.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6952    2.0900   -0.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4759    1.9372    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1743   -0.3943    1.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5066   -0.6003    1.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6332    0.4711   -0.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5179    1.8185   -0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5841    2.4712    0.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2673    2.5347    1.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2825    1.5648    2.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1555    0.2026    2.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3729   -0.9808    2.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9771   -2.2995    1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1660   -0.9936    0.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6360   -3.1245   -0.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1020   -3.2402    0.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7647   -1.6685   -1.9969 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  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
 11  9  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
 11 43  1  0
 12 44  1  0
 12 45  1  0
 13 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  O   UNK     0      32.900  -7.483   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      34.440  -7.483   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      35.210  -8.816   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      36.750  -8.816   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      37.520 -10.150   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      39.060 -10.150   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      36.750 -11.484   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      37.520 -12.817   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      36.750 -14.151   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      37.520 -15.485   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      36.750 -16.819   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.210 -16.819   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.440 -18.152   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      32.900 -18.152   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.130 -16.819   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.590 -16.819   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.257 -17.589   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.487 -18.922   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.946 -18.922   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.176 -20.256   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      29.257 -16.049   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      26.946 -21.590   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.176 -22.923   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      24.636 -22.923   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      23.866 -24.257   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.326 -24.257   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    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   21                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   22                                                       
CONECT   21   16   17                                                       
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

COMPND    HMDB0013652
HETATM    1  C1  UNL     1     -10.450  -0.387  -0.017  1.00  0.00           C  
HETATM    2  C2  UNL     1      -9.130   0.326  -0.241  1.00  0.00           C  
HETATM    3  C3  UNL     1      -8.353  -0.461  -1.273  1.00  0.00           C  
HETATM    4  C4  UNL     1      -7.026   0.142  -1.584  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.130   0.224  -0.323  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.898  -1.106   0.230  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.721  -1.610   0.418  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.383  -1.161   0.216  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.979   0.176  -0.204  1.00  0.00           C  
HETATM   10  O1  UNL     1      -3.225   1.331   0.544  1.00  0.00           O  
HETATM   11  C10 UNL     1      -1.911   0.943   0.579  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.889   1.752  -0.210  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.108   0.902  -1.122  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.191   0.712  -1.125  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.066   1.388  -0.132  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.784   0.330   0.645  1.00  0.00           C  
HETATM   17  C16 UNL     1       4.074   0.223   0.674  1.00  0.00           C  
HETATM   18  C17 UNL     1       4.989   1.132  -0.056  1.00  0.00           C  
HETATM   19  C18 UNL     1       5.897   1.848   0.913  1.00  0.00           C  
HETATM   20  C19 UNL     1       6.751   0.960   1.726  1.00  0.00           C  
HETATM   21  C20 UNL     1       7.695   0.191   0.889  1.00  0.00           C  
HETATM   22  O2  UNL     1       7.808   0.419  -0.336  1.00  0.00           O  
HETATM   23  N1  UNL     1       8.503  -0.831   1.458  1.00  0.00           N  
HETATM   24  C21 UNL     1       9.435  -1.649   0.774  1.00  0.00           C  
HETATM   25  C22 UNL     1       8.806  -2.531  -0.256  1.00  0.00           C  
HETATM   26  O3  UNL     1       8.150  -1.842  -1.249  1.00  0.00           O  
HETATM   27  H1  UNL     1     -11.168   0.392   0.322  1.00  0.00           H  
HETATM   28  H2  UNL     1     -10.265  -1.157   0.765  1.00  0.00           H  
HETATM   29  H3  UNL     1     -10.744  -0.818  -0.988  1.00  0.00           H  
HETATM   30  H4  UNL     1      -8.629   0.399   0.724  1.00  0.00           H  
HETATM   31  H5  UNL     1      -9.258   1.348  -0.643  1.00  0.00           H  
HETATM   32  H6  UNL     1      -8.952  -0.428  -2.208  1.00  0.00           H  
HETATM   33  H7  UNL     1      -8.289  -1.544  -1.003  1.00  0.00           H  
HETATM   34  H8  UNL     1      -6.537  -0.459  -2.374  1.00  0.00           H  
HETATM   35  H9  UNL     1      -7.184   1.157  -1.994  1.00  0.00           H  
HETATM   36  H10 UNL     1      -5.206   0.630  -0.746  1.00  0.00           H  
HETATM   37  H11 UNL     1      -6.676   0.874   0.374  1.00  0.00           H  
HETATM   38  H12 UNL     1      -6.823  -1.724   0.506  1.00  0.00           H  
HETATM   39  H13 UNL     1      -4.799  -2.681   0.855  1.00  0.00           H  
HETATM   40  H14 UNL     1      -2.795  -1.356   1.204  1.00  0.00           H  
HETATM   41  H15 UNL     1      -2.784  -1.897  -0.454  1.00  0.00           H  
HETATM   42  H16 UNL     1      -2.841   0.314  -1.316  1.00  0.00           H  
HETATM   43  H17 UNL     1      -1.563   0.508   1.526  1.00  0.00           H  
HETATM   44  H18 UNL     1      -1.447   2.522  -0.847  1.00  0.00           H  
HETATM   45  H19 UNL     1      -0.311   2.330   0.484  1.00  0.00           H  
HETATM   46  H20 UNL     1      -0.651   0.337  -1.916  1.00  0.00           H  
HETATM   47  H21 UNL     1       1.665   0.043  -1.869  1.00  0.00           H  
HETATM   48  H22 UNL     1       2.695   2.090  -0.662  1.00  0.00           H  
HETATM   49  H23 UNL     1       1.476   1.937   0.662  1.00  0.00           H  
HETATM   50  H24 UNL     1       2.174  -0.394   1.222  1.00  0.00           H  
HETATM   51  H25 UNL     1       4.507  -0.600   1.285  1.00  0.00           H  
HETATM   52  H26 UNL     1       5.633   0.471  -0.722  1.00  0.00           H  
HETATM   53  H27 UNL     1       4.518   1.818  -0.765  1.00  0.00           H  
HETATM   54  H28 UNL     1       6.584   2.471   0.273  1.00  0.00           H  
HETATM   55  H29 UNL     1       5.267   2.535   1.526  1.00  0.00           H  
HETATM   56  H30 UNL     1       7.282   1.565   2.505  1.00  0.00           H  
HETATM   57  H31 UNL     1       6.155   0.203   2.316  1.00  0.00           H  
HETATM   58  H32 UNL     1       8.373  -0.981   2.524  1.00  0.00           H  
HETATM   59  H33 UNL     1       9.977  -2.299   1.508  1.00  0.00           H  
HETATM   60  H34 UNL     1      10.166  -0.994   0.230  1.00  0.00           H  
HETATM   61  H35 UNL     1       9.636  -3.124  -0.752  1.00  0.00           H  
HETATM   62  H36 UNL     1       8.102  -3.240   0.252  1.00  0.00           H  
HETATM   63  H37 UNL     1       8.765  -1.668  -1.997  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   11   42
CONECT   10   11
CONECT   11   12   43
CONECT   12   13   44   45
CONECT   13   14   14   46
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

HMDB0013652
     RDKit          3D
(±)11(12)-EET Ethanolamide
 63 63  0  0  0  0  0  0  0  0999 V2000
  -10.4499   -0.3874   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1300    0.3263   -0.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3534   -0.4606   -1.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0264    0.1418   -1.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1299    0.2240   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8981   -1.1064    0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7206   -1.6104    0.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3829   -1.1614    0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9791    0.1765   -0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2253    1.3307    0.5436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9114    0.9432    0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8890    1.7516   -0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1081    0.9016   -1.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1915    0.7120   -1.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0663    1.3885   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7838    0.3301    0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0738    0.2232    0.6745 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9891    1.1316   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8973    1.8485    0.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7507    0.9601    1.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6948    0.1915    0.8890 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8078    0.4195   -0.3363 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5025   -0.8315    1.4579 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4345   -1.6493    0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8065   -2.5308   -0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1497   -1.8419   -1.2489 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1677    0.3923    0.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2647   -1.1573    0.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7441   -0.8181   -0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6289    0.3994    0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2579    1.3479   -0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9518   -0.4275   -2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2892   -1.5441   -1.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5372   -0.4587   -2.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1841    1.1572   -1.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2060    0.6298   -0.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6763    0.8740    0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8228   -1.7241    0.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7991   -2.6806    0.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952   -1.3561    1.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7837   -1.8967   -0.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415    0.3142   -1.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5627    0.5081    1.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4465    2.5220   -0.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3107    2.3296    0.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6505    0.3365   -1.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6653    0.0426   -1.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6952    2.0900   -0.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4759    1.9372    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1743   -0.3943    1.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5066   -0.6003    1.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6332    0.4711   -0.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5179    1.8185   -0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5841    2.4712    0.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2673    2.5347    1.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2825    1.5648    2.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1555    0.2026    2.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3729   -0.9808    2.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9771   -2.2995    1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1660   -0.9936    0.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6360   -3.1245   -0.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1020   -3.2402    0.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7647   -1.6685   -1.9969 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  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
 11  9  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
 11 43  1  0
 12 44  1  0
 12 45  1  0
 13 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
11(12)-EET-ea	ChEBI
11(12)-EpETrE-ea	ChEBI
11,12-EET-ea	ChEBI
N-(11,12-Epoxy-5Z,8Z,14Z-eicosatrienoyl)-ethanolamine	ChEBI
N-(11,12-Epoxy-5Z,8Z,14Z-icosatrienoyl)ethanolamine	ChEBI
(+/-)11(12)-epetre ethanolamide	HMDB

Chemical Formula

C₂₂H₃₇NO₃

Average Molecular Weight

363.5341

Monoisotopic Molecular Weight

363.277344055

IUPAC Name

(5Z,8Z)-N-(2-hydroxyethyl)-10-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienamide

Traditional Name

(5Z,8Z)-N-(2-hydroxyethyl)-10-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienamide

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H37NO3/c1-2-3-4-5-9-12-15-20-21(26-20)16-13-10-7-6-8-11-14-17-22(25)23-18-19-24/h6,8-10,12-13,20-21,24H,2-5,7,11,14-19H2,1H3,(H,23,25)/b8-6-,12-9-,13-10-

InChI Key

TYRRSRADDAROSO-KROJNAHFSA-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) (LMFA08040034 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0013652)

Exogenous

Food

Food (HMDB: HMDB0013652)

Exogenous (HMDB: HMDB0013652)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0013652)

Role

Biological role

Energy source (HMDB: HMDB0013652)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013652)

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	0.00088 g/L	ALOGPS
logP	5.43	ALOGPS
logP	4.38	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	15.44	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	44.05 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
DeepCCS	[M+H]+	193.288	30932474
DeepCCS	[M-H]-	190.93	30932474
DeepCCS	[M-2H]-	224.013	30932474
DeepCCS	[M+Na]+	199.465	30932474
AllCCS	[M+H]+	198.7	32859911
AllCCS	[M+H-H2O]+	196.2	32859911
AllCCS	[M+NH4]+	201.0	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 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.	7.42 minutes	32390414
Predicted by Siyang on May 30, 2022	19.4078 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.2 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	34.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3082.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	313.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	207.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	221.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	568.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	915.6 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	537.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	165.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1859.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	646.9 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	1808.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	647.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	500.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	340.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	379.2 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	8.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(??)11(12)-EET Ethanolamide	CCCCC\C=C/CC1OC1C\C=C/C\C=C/CCCC(=O)NCCO	3253.5	Standard polar	33892256
(??)11(12)-EET Ethanolamide	CCCCC\C=C/CC1OC1C\C=C/C\C=C/CCCC(=O)NCCO	2677.6	Standard non polar	33892256
(??)11(12)-EET Ethanolamide	CCCCC\C=C/CC1OC1C\C=C/C\C=C/CCCC(=O)NCCO	3012.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(??)11(12)-EET Ethanolamide,1TMS,isomer #1	CCCCC/C=C\CC1OC1C/C=C\C/C=C\CCCC(=O)NCCO[Si](C)(C)C	2979.3	Semi standard non polar	33892256
(??)11(12)-EET Ethanolamide,1TMS,isomer #2	CCCCC/C=C\CC1OC1C/C=C\C/C=C\CCCC(=O)N(CCO)[Si](C)(C)C	2907.6	Semi standard non polar	33892256
(±)11(12)-EET Ethanolamide,2TMS,isomer #1	CCCCC/C=C\CC1OC1C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2940.0	Semi standard non polar	33892256
(±)11(12)-EET Ethanolamide,2TMS,isomer #1	CCCCC/C=C\CC1OC1C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	3019.4	Standard non polar	33892256
(±)11(12)-EET Ethanolamide,2TMS,isomer #1	CCCCC/C=C\CC1OC1C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	3097.0	Standard polar	33892256
(??)11(12)-EET Ethanolamide,1TBDMS,isomer #1	CCCCC/C=C\CC1OC1C/C=C\C/C=C\CCCC(=O)NCCO[Si](C)(C)C(C)(C)C	3216.7	Semi standard non polar	33892256
(??)11(12)-EET Ethanolamide,1TBDMS,isomer #2	CCCCC/C=C\CC1OC1C/C=C\C/C=C\CCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C	3136.6	Semi standard non polar	33892256
(±)11(12)-EET Ethanolamide,2TBDMS,isomer #1	CCCCC/C=C\CC1OC1C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3427.4	Semi standard non polar	33892256
(±)11(12)-EET Ethanolamide,2TBDMS,isomer #1	CCCCC/C=C\CC1OC1C/C=C\C/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
(±)11(12)-EET Ethanolamide,2TBDMS,isomer #1	CCCCC/C=C\CC1OC1C/C=C\C/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 - (±)11(12)-EET Ethanolamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-8694000000-6d3847325b2b7040cee2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)11(12)-EET Ethanolamide GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-8796300000-08d23c6d3b184e010dae	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)11(12)-EET Ethanolamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)11(12)-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 - (±)11(12)-EET Ethanolamide 10V, Positive-QTOF	splash10-03di-4129000000-910d6ee245580b6ad5cc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)11(12)-EET Ethanolamide 20V, Positive-QTOF	splash10-03di-9311000000-c066370e8bc76292f791	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)11(12)-EET Ethanolamide 40V, Positive-QTOF	splash10-03kc-9400000000-719f47ab5fde92ea853e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)11(12)-EET Ethanolamide 10V, Negative-QTOF	splash10-03di-0119000000-aee82aac64e21c8ff5e7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)11(12)-EET Ethanolamide 20V, Negative-QTOF	splash10-03dl-5219000000-5757c2d1716a1ad61a24	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)11(12)-EET Ethanolamide 40V, Negative-QTOF	splash10-01ox-9300000000-dac6a7b4529aa109cd72	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)11(12)-EET Ethanolamide 10V, Negative-QTOF	splash10-03di-0009000000-ea75254cd356aac3e606	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)11(12)-EET Ethanolamide 20V, Negative-QTOF	splash10-03di-3129000000-a8f779297baa545ea5be	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)11(12)-EET Ethanolamide 40V, Negative-QTOF	splash10-0006-9133000000-18b69b4fe133f3d381a9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)11(12)-EET Ethanolamide 10V, Positive-QTOF	splash10-03di-9117000000-938cc0536a78351d1651	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)11(12)-EET Ethanolamide 20V, Positive-QTOF	splash10-0006-9001000000-f9d2451870ca0ec8533f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)11(12)-EET Ethanolamide 40V, Positive-QTOF	splash10-0006-9100000000-2f1ee6d42f6b011c032e	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

FDB029622

KNApSAcK ID

Not Available

Chemspider ID

17220862

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16061183

PDB ID

Not Available

ChEBI ID

136990

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 ]
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 ]

Showing metabocard for (±)11(12)-EET Ethanolamide (HMDB0013652)

MOL for HMDB0013652 ((±)11(12)-EET Ethanolamide)

3D MOL for HMDB0013652 ((±)11(12)-EET Ethanolamide)

3D SDF for HMDB0013652 ((±)11(12)-EET Ethanolamide)

3D-SDF for HMDB0013652 ((±)11(12)-EET Ethanolamide)

PDB for HMDB0013652 ((±)11(12)-EET Ethanolamide)

3D PDB for HMDB0013652 ((±)11(12)-EET Ethanolamide)

SMILES for HMDB0013652 ((±)11(12)-EET Ethanolamide)

INCHI for HMDB0013652 ((±)11(12)-EET Ethanolamide)

Structure for HMDB0013652 ((±)11(12)-EET Ethanolamide)

3D Structure for HMDB0013652 ((±)11(12)-EET Ethanolamide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra