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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2010-05-20 09:42:05 UTC

Update Date

2022-03-07 02:51:33 UTC

HMDB ID

HMDB0013621

Secondary Accession Numbers

HMDB13621

Metabolite Identification

Common Name

16(17)-EpDPE

Description

16(17)-EpETE is the DHA homolog of 14(15)-EpETrE, derived via epoxidation of the 16,17-double bond of docosahexaenoic acid (DHA). The EDHF (endothelium-derived hyperpolarizing factor) activity of 16(17)-EpDPE has not yet been determined. The epoxygenase metabolites of DHA have also been detected in a murine inflammation model (PMID: 12391014 ). EDHF is an unidentified mediator released from vascular endothelial cells in response to acetylcholine and bradykinin which is distinct from the NOS- (nitric oxide) and COX-derived (prostacyclin) vasodilators (PMID: 9504399 , 10519554 ). Cytochrome P450 (CYP450) metabolism of polyunsaturated fatty acids produces epoxides such as 14(15)-EpETrE which are prime candidates for the actual active mediator (PMID: 9401962 ). However, the CYP450 metabolites of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) have been little studied relative to arachidonate epoxygenase metabolites.

Structure

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

HMDB0013621
     RDKit          3D
16(17)-EpDPE
 57 57  0  0  0  0  0  0  0  0999 V2000
    7.1727   -3.4132   -1.9317 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8921   -1.9413   -1.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4399   -1.7128   -1.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6995   -1.3126   -0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1679   -1.0272    0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9047    0.4178    1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2823    0.8605    2.2623 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9107    0.6908    2.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0741    1.9582    1.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3133    1.9348    0.6070 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0111    1.9898    0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1187    2.0878    1.6402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6921    3.3129    1.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0009    3.2849    1.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415    2.0698    1.6394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6903    2.0970    0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6921    1.1752   -0.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8854   -0.0125   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5388   -1.3103   -0.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8139   -1.5522   -0.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9464   -0.6477   -0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8861   -0.7168   -1.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4931   -2.0586   -1.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1795   -2.3638   -2.7630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3130   -2.9774   -0.7219 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0263   -3.4577   -2.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4997   -3.8843   -0.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -3.8943   -2.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2862   -1.6327   -0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4509   -1.3008   -2.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9139   -1.8813   -2.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6177   -1.1642   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4884   -1.6447    1.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1711   -1.3443    0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1578    1.1249    0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4866   -0.1582    2.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7620    2.8630    1.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4524    2.0272    2.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9344    1.8609   -0.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6067    1.9610   -0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6223    1.9211    2.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5608    1.2124    1.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1912    4.3208    1.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5497    4.2738    1.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3569    1.1401    1.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5625    2.2056    2.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3716    2.9625    0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3570    1.3489   -1.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2855    0.0238   -1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0772   -0.0092    0.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8498   -2.2276   -0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0777   -2.6555   -0.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6170   -1.1320    0.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8172    0.3425    0.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6771    0.0378   -1.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3754   -0.5006   -2.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0262   -3.5717   -0.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  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  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  8  6  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 25 57  1  0
M  END


  Mrv0541 02271200282D          

 25 25  0  0  0  0            999 V2000
    5.7051  -10.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4196  -10.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1341  -10.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9591  -10.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6736  -10.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3880  -10.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2130  -10.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8170  -10.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5314  -10.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2459  -10.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9604  -10.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6749  -10.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3894  -10.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1038  -10.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8183  -10.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5328  -10.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2472  -10.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9617  -10.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6762  -10.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3907  -10.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1052  -10.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8197  -10.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5341  -10.6232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8197   -9.3857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8005  -11.3377    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 25  6  1  0  0  0  0
 25  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013621

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C=C/CC1OC1C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O3/c1-2-3-14-17-20-21(25-20)18-15-12-10-8-6-4-5-7-9-11-13-16-19-22(23)24/h3,5-8,11-15,20-21H,2,4,9-10,16-19H2,1H3,(H,23,24)/b7-5-,8-6-,13-11-,14-3-,15-12-

> <INCHI_KEY>
BCTXZWCPBLWCRV-ZYADFMMDSA-N

> <FORMULA>
C22H32O3

> <MOLECULAR_WEIGHT>
344.4877

> <EXACT_MASS>
344.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
40.414479877707194

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoic acid

> <ALOGPS_LOGP>
6.16

> <JCHEM_LOGP>
5.814467922666665

> <ALOGPS_LOGS>
-6.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.885498414696288

> <JCHEM_PKA_STRONGEST_BASIC>
-4.207091543618949

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
109.79350000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.74e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013621
     RDKit          3D
16(17)-EpDPE
 57 57  0  0  0  0  0  0  0  0999 V2000
    7.1727   -3.4132   -1.9317 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8921   -1.9413   -1.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4399   -1.7128   -1.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6995   -1.3126   -0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1679   -1.0272    0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9047    0.4178    1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2823    0.8605    2.2623 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9107    0.6908    2.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0741    1.9582    1.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3133    1.9348    0.6070 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0111    1.9898    0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1187    2.0878    1.6402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6921    3.3129    1.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0009    3.2849    1.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415    2.0698    1.6394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6903    2.0970    0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6921    1.1752   -0.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8854   -0.0125   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5388   -1.3103   -0.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8139   -1.5522   -0.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9464   -0.6477   -0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8861   -0.7168   -1.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4931   -2.0586   -1.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1795   -2.3638   -2.7630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3130   -2.9774   -0.7219 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0263   -3.4577   -2.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4997   -3.8843   -0.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -3.8943   -2.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2862   -1.6327   -0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4509   -1.3008   -2.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9139   -1.8813   -2.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6177   -1.1642   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4884   -1.6447    1.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1711   -1.3443    0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1578    1.1249    0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4866   -0.1582    2.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7620    2.8630    1.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4524    2.0272    2.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9344    1.8609   -0.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6067    1.9610   -0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6223    1.9211    2.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5608    1.2124    1.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1912    4.3208    1.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5497    4.2738    1.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3569    1.1401    1.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5625    2.2056    2.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3716    2.9625    0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3570    1.3489   -1.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2855    0.0238   -1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0772   -0.0092    0.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8498   -2.2276   -0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0777   -2.6555   -0.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6170   -1.1320    0.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8172    0.3425    0.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6771    0.0378   -1.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3754   -0.5006   -2.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0262   -3.5717   -0.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  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  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  8  6  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 25 57  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0      10.650 -19.830   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.983 -19.060   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.317 -19.830   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.857 -19.830   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.191 -19.060   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.524 -19.830   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.064 -19.830   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.192 -19.060   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.525 -19.830   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.859 -19.830   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.193 -19.060   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.526 -19.830   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.860 -19.830   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.194 -19.060   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.527 -19.830   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.861 -19.830   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      32.195 -19.060   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      33.529 -19.830   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      34.862 -19.830   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      36.196 -19.060   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      37.530 -19.830   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      38.863 -19.060   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      40.197 -19.830   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      38.863 -17.520   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      18.294 -21.164   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   25                                                  
CONECT    7    6    8   25                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    6    7                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

COMPND    HMDB0013621
HETATM    1  C1  UNL     1       7.173  -3.413  -1.932  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.892  -1.941  -1.604  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.440  -1.713  -1.716  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.700  -1.313  -0.731  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.168  -1.027   0.630  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.905   0.418   1.013  1.00  0.00           C  
HETATM    7  O1  UNL     1       5.282   0.860   2.262  1.00  0.00           O  
HETATM    8  C7  UNL     1       3.911   0.691   2.036  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.074   1.958   1.857  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.313   1.935   0.607  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.011   1.990   0.455  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.119   2.088   1.640  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.692   3.313   1.625  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.001   3.285   1.625  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.841   2.070   1.639  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.690   2.097   0.413  1.00  0.00           C  
HETATM   17  C16 UNL     1      -3.692   1.175  -0.512  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.885  -0.012  -0.507  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.539  -1.310  -0.508  1.00  0.00           C  
HETATM   20  C19 UNL     1      -4.814  -1.552  -0.472  1.00  0.00           C  
HETATM   21  C20 UNL     1      -5.946  -0.648  -0.413  1.00  0.00           C  
HETATM   22  C21 UNL     1      -6.886  -0.717  -1.607  1.00  0.00           C  
HETATM   23  C22 UNL     1      -7.493  -2.059  -1.731  1.00  0.00           C  
HETATM   24  O2  UNL     1      -8.180  -2.364  -2.763  1.00  0.00           O  
HETATM   25  O3  UNL     1      -7.313  -2.977  -0.722  1.00  0.00           O  
HETATM   26  H1  UNL     1       8.026  -3.458  -2.633  1.00  0.00           H  
HETATM   27  H2  UNL     1       7.500  -3.884  -0.970  1.00  0.00           H  
HETATM   28  H3  UNL     1       6.262  -3.894  -2.328  1.00  0.00           H  
HETATM   29  H4  UNL     1       7.286  -1.633  -0.643  1.00  0.00           H  
HETATM   30  H5  UNL     1       7.451  -1.301  -2.360  1.00  0.00           H  
HETATM   31  H6  UNL     1       4.914  -1.881  -2.680  1.00  0.00           H  
HETATM   32  H7  UNL     1       3.618  -1.164  -0.898  1.00  0.00           H  
HETATM   33  H8  UNL     1       4.488  -1.645   1.308  1.00  0.00           H  
HETATM   34  H9  UNL     1       6.171  -1.344   0.882  1.00  0.00           H  
HETATM   35  H10 UNL     1       5.158   1.125   0.196  1.00  0.00           H  
HETATM   36  H11 UNL     1       3.487  -0.158   2.587  1.00  0.00           H  
HETATM   37  H12 UNL     1       3.762   2.863   1.903  1.00  0.00           H  
HETATM   38  H13 UNL     1       2.452   2.027   2.743  1.00  0.00           H  
HETATM   39  H14 UNL     1       2.934   1.861  -0.324  1.00  0.00           H  
HETATM   40  H15 UNL     1       0.607   1.961  -0.559  1.00  0.00           H  
HETATM   41  H16 UNL     1       0.622   1.921   2.611  1.00  0.00           H  
HETATM   42  H17 UNL     1      -0.561   1.212   1.537  1.00  0.00           H  
HETATM   43  H18 UNL     1      -0.191   4.321   1.613  1.00  0.00           H  
HETATM   44  H19 UNL     1      -2.550   4.274   1.613  1.00  0.00           H  
HETATM   45  H20 UNL     1      -2.357   1.140   1.862  1.00  0.00           H  
HETATM   46  H21 UNL     1      -3.562   2.206   2.537  1.00  0.00           H  
HETATM   47  H22 UNL     1      -4.372   2.963   0.274  1.00  0.00           H  
HETATM   48  H23 UNL     1      -4.357   1.349  -1.389  1.00  0.00           H  
HETATM   49  H24 UNL     1      -2.286   0.024  -1.501  1.00  0.00           H  
HETATM   50  H25 UNL     1      -2.077  -0.009   0.280  1.00  0.00           H  
HETATM   51  H26 UNL     1      -2.850  -2.228  -0.547  1.00  0.00           H  
HETATM   52  H27 UNL     1      -5.078  -2.656  -0.490  1.00  0.00           H  
HETATM   53  H28 UNL     1      -6.617  -1.132   0.442  1.00  0.00           H  
HETATM   54  H29 UNL     1      -5.817   0.343   0.009  1.00  0.00           H  
HETATM   55  H30 UNL     1      -7.677   0.038  -1.485  1.00  0.00           H  
HETATM   56  H31 UNL     1      -6.375  -0.501  -2.562  1.00  0.00           H  
HETATM   57  H32 UNL     1      -8.026  -3.572  -0.337  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4    4   31
CONECT    4    5   32
CONECT    5    6   33   34
CONECT    6    7    8   35
CONECT    7    8
CONECT    8    9   36
CONECT    9   10   37   38
CONECT   10   11   11   39
CONECT   11   12   40
CONECT   12   13   41   42
CONECT   13   14   14   43
CONECT   14   15   44
CONECT   15   16   45   46
CONECT   16   17   17   47
CONECT   17   18   48
CONECT   18   19   49   50
CONECT   19   20   20   51
CONECT   20   21   52
CONECT   21   22   53   54
CONECT   22   23   55   56
CONECT   23   24   24   25
CONECT   25   57
END

HMDB0013621
     RDKit          3D
16(17)-EpDPE
 57 57  0  0  0  0  0  0  0  0999 V2000
    7.1727   -3.4132   -1.9317 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8921   -1.9413   -1.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4399   -1.7128   -1.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6995   -1.3126   -0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1679   -1.0272    0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9047    0.4178    1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2823    0.8605    2.2623 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9107    0.6908    2.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0741    1.9582    1.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3133    1.9348    0.6070 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0111    1.9898    0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1187    2.0878    1.6402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6921    3.3129    1.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0009    3.2849    1.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415    2.0698    1.6394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6903    2.0970    0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6921    1.1752   -0.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8854   -0.0125   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5388   -1.3103   -0.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8139   -1.5522   -0.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9464   -0.6477   -0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8861   -0.7168   -1.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4931   -2.0586   -1.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1795   -2.3638   -2.7630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3130   -2.9774   -0.7219 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0263   -3.4577   -2.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4997   -3.8843   -0.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -3.8943   -2.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2862   -1.6327   -0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4509   -1.3008   -2.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9139   -1.8813   -2.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6177   -1.1642   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4884   -1.6447    1.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1711   -1.3443    0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1578    1.1249    0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4866   -0.1582    2.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7620    2.8630    1.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4524    2.0272    2.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9344    1.8609   -0.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6067    1.9610   -0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6223    1.9211    2.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5608    1.2124    1.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1912    4.3208    1.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5497    4.2738    1.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3569    1.1401    1.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5625    2.2056    2.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3716    2.9625    0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3570    1.3489   -1.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2855    0.0238   -1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0772   -0.0092    0.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8498   -2.2276   -0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0777   -2.6555   -0.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6170   -1.1320    0.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8172    0.3425    0.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6771    0.0378   -1.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3754   -0.5006   -2.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0262   -3.5717   -0.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  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  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  8  6  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 25 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
16(17)-Epoxy-4Z,7Z,10Z,13Z,19Z-docosapentaenoic acid	ChEBI
16,17-EDP	ChEBI
16,17-Epoxydocosapentaenoic acid	ChEBI
16(17)-Epoxy-4Z,7Z,10Z,13Z,19Z-docosapentaenoate	Generator
16,17-Epoxydocosapentaenoate	Generator
16(17)-EpDoPE	HMDB

Chemical Formula

C₂₂H₃₂O₃

Average Molecular Weight

344.4877

Monoisotopic Molecular Weight

344.23514489

IUPAC Name

(4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoic acid

Traditional Name

(4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoic acid

CAS Registry Number

Not Available

SMILES

CC\C=C/CC1OC1C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O

InChI Identifier

InChI=1S/C22H32O3/c1-2-3-14-17-20-21(25-20)18-15-12-10-8-6-4-5-7-9-11-13-16-19-22(23)24/h3,5-8,11-15,20-21H,2,4,9-10,16-19H2,1H3,(H,23,24)/b7-5-,8-6-,13-11-,14-3-,15-12-

InChI Key

BCTXZWCPBLWCRV-ZYADFMMDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Epoxy fatty acid
Heterocyclic fatty acid
Unsaturated fatty acid
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

EpDPE (CHEBI:72855 )
Docosanoids (LMFA04000037 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 20671299)

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0013621)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0013621)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013621)

Source

Endogenous

Endogenous (HMDB: HMDB0013621)

Animal

Animal (HMDB: HMDB0013621)

Exogenous

Food

Food (HMDB: HMDB0013621)

Exogenous (HMDB: HMDB0013621)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0013621)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0013621)

Lipid metabolism pathway (HMDB: HMDB0013621)

Cellular process

Cell signaling (HMDB: HMDB0013621)

Biochemical process

Lipid transport (HMDB: HMDB0013621)

Role

Biological role

Energy source (HMDB: HMDB0013621)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013621)

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	0.00027 g/L	ALOGPS
logP	6.16	ALOGPS
logP	5.81	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	4.89	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	109.79 m³·mol⁻¹	ChemAxon
Polarizability	40.41 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	193.182	31661259
DarkChem	[M-H]-	191.551	31661259
DeepCCS	[M+H]+	188.6	30932474
DeepCCS	[M-H]-	186.242	30932474
DeepCCS	[M-2H]-	219.128	30932474
DeepCCS	[M+Na]+	194.694	30932474
AllCCS	[M+H]+	195.3	32859911
AllCCS	[M+H-H2O]+	192.5	32859911
AllCCS	[M+NH4]+	197.9	32859911
AllCCS	[M+Na]+	198.6	32859911
AllCCS	[M-H]-	191.1	32859911
AllCCS	[M+Na-2H]-	192.9	32859911
AllCCS	[M+HCOO]-	195.0	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.	6.38 minutes	32390414
Predicted by Siyang on May 30, 2022	24.4027 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.97 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	35.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3301.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	524.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	232.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	399.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	697.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1199.3 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	569.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	93.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2288.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	798.9 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	1946.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	874.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	551.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	452.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	593.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
16(17)-EpDPE	CC\C=C/CC1OC1C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O	3994.5	Standard polar	33892256
16(17)-EpDPE	CC\C=C/CC1OC1C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O	2469.6	Standard non polar	33892256
16(17)-EpDPE	CC\C=C/CC1OC1C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O	2700.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
16(17)-EpDPE,1TMS,isomer #1	CC/C=C\CC1OC1C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C	2638.4	Semi standard non polar	33892256
16(17)-EpDPE,1TBDMS,isomer #1	CC/C=C\CC1OC1C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C	2897.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 16(17)-EpDPE GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lr-5391000000-eca8613c027ec77114b9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16(17)-EpDPE GC-MS (1 TMS) - 70eV, Positive	splash10-0rta-9344100000-eae04a555061ea8367e3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16(17)-EpDPE 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 - 16(17)-EpDPE 10V, Positive-QTOF	splash10-004j-1029000000-6aa72f00daadb1ba4c7f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16(17)-EpDPE 20V, Positive-QTOF	splash10-017i-9383000000-5a0d6eec821440733720	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16(17)-EpDPE 40V, Positive-QTOF	splash10-0fe3-9630000000-d10dfa768fb9fefdcdc7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16(17)-EpDPE 10V, Negative-QTOF	splash10-0006-1029000000-2494b8cd0c2c4c4afa84	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16(17)-EpDPE 20V, Negative-QTOF	splash10-002g-3069000000-9ec5ad4d4f5d363b8019	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16(17)-EpDPE 40V, Negative-QTOF	splash10-052f-9020000000-561f45aa1c0eb363a33b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16(17)-EpDPE 10V, Positive-QTOF	splash10-004j-2139000000-6c4dd45859b7c6798121	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16(17)-EpDPE 20V, Positive-QTOF	splash10-0arr-9826000000-b688bc2e69f1c52c2062	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16(17)-EpDPE 40V, Positive-QTOF	splash10-0693-9700000000-06fa0665d1492676af5c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16(17)-EpDPE 10V, Negative-QTOF	splash10-0006-0039000000-c68ec18fd5d4ac034e16	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16(17)-EpDPE 20V, Negative-QTOF	splash10-004l-2149000000-8efe3784e6b394626646	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16(17)-EpDPE 40V, Negative-QTOF	splash10-052f-9031000000-880d8778f1345dabf38d	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000239 +/- 0.000048 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.000368 +/- 0.00043 uM	Adult (>18 years old)	Both	Normal	21359215	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029598

KNApSAcK ID

Not Available

Chemspider ID

21466945

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14392758

PDB ID

Not Available

ChEBI ID

72855

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

Fisslthaler B, Popp R, Kiss L, Potente M, Harder DR, Fleming I, Busse R: Cytochrome P450 2C is an EDHF synthase in coronary arteries. Nature. 1999 Sep 30;401(6752):493-7. [PubMed:10519554 ]
Serhan CN, Hong S, Gronert K, Colgan SP, Devchand PR, Mirick G, Moussignac RL: Resolvins: a family of bioactive products of omega-3 fatty acid transformation circuits initiated by aspirin treatment that counter proinflammation signals. J Exp Med. 2002 Oct 21;196(8):1025-37. [PubMed:12391014 ]
Chataigneau T, Feletou M, Duhault J, Vanhoutte PM: Epoxyeicosatrienoic acids, potassium channel blockers and endothelium-dependent hyperpolarization in the guinea-pig carotid artery. Br J Pharmacol. 1998 Feb;123(3):574-80. [PubMed:9504399 ]
Baron A, Frieden M, Beny JL: Epoxyeicosatrienoic acids activate a high-conductance, Ca(2+)-dependent K + channel on pig coronary artery endothelial cells. J Physiol. 1997 Nov 1;504 ( Pt 3):537-43. [PubMed:9401962 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 16(17)-EpDPE (HMDB0013621)

MOL for HMDB0013621 (16(17)-EpDPE)

3D MOL for HMDB0013621 (16(17)-EpDPE)

3D SDF for HMDB0013621 (16(17)-EpDPE)

3D-SDF for HMDB0013621 (16(17)-EpDPE)

PDB for HMDB0013621 (16(17)-EpDPE)

3D PDB for HMDB0013621 (16(17)-EpDPE)

SMILES for HMDB0013621 (16(17)-EpDPE)

INCHI for HMDB0013621 (16(17)-EpDPE)

Structure for HMDB0013621 (16(17)-EpDPE)

3D Structure for HMDB0013621 (16(17)-EpDPE)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra