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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:46 UTC

Update Date

2022-03-07 02:49:14 UTC

HMDB ID

HMDB0002283

Secondary Accession Numbers

HMDB02283

Metabolite Identification

Common Name

14R,15S-EpETrE

Description

14R,15S-EpETrE is the dominant extracellular metabolite of epoxygenase products of arachidonic acid released from human luteinised granulosa cells. Epoxyeicosatrienoic acids (EpETrEs) have been reported recently having vasodilatory effects and a role of P-450-dependent arachidonic acid monooxygenase metabolites is suggested in vasoregulation. The physiological role of this compound has not been totally established, although in other tissues EpETrEs are mainly involved in hormone production and in the vascular and renal systems. Some studies have implicated epoxygenase metabolites of arachidonic acid in the control of steroidogenesis in luteinised granulosa cells. (PMID: 12749593 , 12361727 , 1650001 ).

Structure

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

HMDB0002283
     RDKit          3D
14R,15S-EpETrE
 55 55  0  0  0  0  0  0  0  0999 V2000
   -8.2830    0.4936   -0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4464   -0.2147    0.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9877   -0.1166    0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8071   -0.7679   -0.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3753   -0.7207   -1.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9595    0.7145   -1.4788 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6275    0.8730   -1.9331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9627    1.3392   -0.6146 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2238    0.5252    0.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2703    1.3200    1.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0266    1.1436    1.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7076    0.0804    0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    0.6394   -0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0307    0.3333   -0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5029   -0.5824    0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1318   -1.7762    0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3776   -2.1657    0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3259   -1.4457    1.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5384   -0.9893    0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2046   -0.0617   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6016    1.2040   -0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4658    1.4788    0.9703 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1711    2.1195   -1.1859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0099    1.1778    0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8884   -0.2065   -0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6666    1.1656   -0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6320    0.2508    1.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7173   -1.2837    0.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3680   -0.6022    1.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7203    0.9504    0.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4337   -0.2584   -1.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1280   -1.8365   -0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3104   -1.1780   -2.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6815   -1.2546   -0.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6547    1.3920   -2.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9989    2.4186   -0.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8225   -0.4168    0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0896    0.1903    1.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6747    2.1604    1.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6344    1.8049    1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9954   -0.8017    1.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0472   -0.3205   -0.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4726    1.3160   -1.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7441    0.7739   -0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7217   -0.8517    1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024   -0.0633    1.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252   -2.4169   -0.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7114   -3.0899   -0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7612   -2.2218    1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9969   -0.6353    1.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1384   -1.8347    0.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1876   -0.4441    1.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5269   -0.5456   -1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1541    0.1447   -1.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0694    3.0930   -0.9413 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  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  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  8  6  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  6
  8 36  1  6
  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
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END


  Mrv0541 02231219282D          

 23 23  0  0  1  0            999 V2000
   17.1745   -2.9290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9054   -7.3560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1910   -8.5934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5870   -3.6435    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.7620   -3.6435    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.3016   -4.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0476   -4.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0161   -3.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7304   -4.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3332   -3.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4448   -3.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6187   -4.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1594   -4.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6187   -4.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9041   -5.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9041   -6.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6187   -6.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0476   -7.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7620   -7.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6187   -7.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3332   -7.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4766   -7.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1910   -7.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2 23  1  0  0  0  0
  3 23  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  1  0  0  0
  5  7  1  1  0  0  0
  6  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 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 20  1  0  0  0  0
 18 19  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 20 21  2  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002283

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC[C@@H]1O[C@@H]1C\C=C/C\C=C/C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-2-3-12-15-18-19(23-18)16-13-10-8-6-4-5-7-9-11-14-17-20(21)22/h4,6-7,9-10,13,18-19H,2-3,5,8,11-12,14-17H2,1H3,(H,21,22)/b6-4-,9-7-,13-10-/t18-,19+/m0/s1

> <INCHI_KEY>
JBSCUHKPLGKXKH-LLZJRKGESA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.4663

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
38.25480278369429

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z,8Z,11Z)-13-[(2R,3S)-3-pentyloxiran-2-yl]trideca-5,8,11-trienoic acid

> <ALOGPS_LOGP>
6.23

> <JCHEM_LOGP>
5.649173906

> <ALOGPS_LOGS>
-6.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771840932639

> <JCHEM_PKA_STRONGEST_BASIC>
-4.204825775212357

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
98.35829999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.19e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14R,15S-EpETrE

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002283
     RDKit          3D
14R,15S-EpETrE
 55 55  0  0  0  0  0  0  0  0999 V2000
   -8.2830    0.4936   -0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4464   -0.2147    0.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9877   -0.1166    0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8071   -0.7679   -0.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3753   -0.7207   -1.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9595    0.7145   -1.4788 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6275    0.8730   -1.9331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9627    1.3392   -0.6146 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2238    0.5252    0.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2703    1.3200    1.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0266    1.1436    1.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7076    0.0804    0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    0.6394   -0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0307    0.3333   -0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5029   -0.5824    0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1318   -1.7762    0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3776   -2.1657    0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3259   -1.4457    1.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5384   -0.9893    0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2046   -0.0617   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6016    1.2040   -0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4658    1.4788    0.9703 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1711    2.1195   -1.1859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0099    1.1778    0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8884   -0.2065   -0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6666    1.1656   -0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6320    0.2508    1.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7173   -1.2837    0.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3680   -0.6022    1.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7203    0.9504    0.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4337   -0.2584   -1.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1280   -1.8365   -0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3104   -1.1780   -2.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6815   -1.2546   -0.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6547    1.3920   -2.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9989    2.4186   -0.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8225   -0.4168    0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0896    0.1903    1.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6747    2.1604    1.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6344    1.8049    1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9954   -0.8017    1.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0472   -0.3205   -0.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4726    1.3160   -1.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7441    0.7739   -0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7217   -0.8517    1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024   -0.0633    1.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252   -2.4169   -0.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7114   -3.0899   -0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7612   -2.2218    1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9969   -0.6353    1.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1384   -1.8347    0.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1876   -0.4441    1.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5269   -0.5456   -1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1541    0.1447   -1.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0694    3.0930   -0.9413 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  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  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  8  6  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  6
  8 36  1  6
  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
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      32.059  -5.467   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      35.290 -13.731   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      33.957 -16.041   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      32.829  -6.801   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      31.289  -6.801   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      34.163  -7.571   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.956  -7.571   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      35.497  -6.801   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      36.830  -7.571   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.622  -6.801   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      38.164  -6.801   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.288  -7.571   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      39.497  -7.571   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.288  -9.111   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.954  -9.881   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.954 -11.421   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.288 -12.191   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.956 -13.731   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      31.289 -14.501   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.288 -13.731   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.622 -14.501   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      32.623 -13.731   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      33.957 -14.501   0.000  0.00  0.00           C+0
CONECT    1    4    5                                                       
CONECT    2   23                                                            
CONECT    3   23                                                            
CONECT    4    1    5    6                                                  
CONECT    5    1    4    7                                                  
CONECT    6    4    8                                                       
CONECT    7    5   10                                                       
CONECT    8    6    9                                                       
CONECT    9    8   11                                                       
CONECT   10    7   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   20                                                       
CONECT   18   19   21                                                       
CONECT   19   18   22                                                       
CONECT   20   17   21                                                       
CONECT   21   18   20                                                       
CONECT   22   19   23                                                       
CONECT   23    2    3   22                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

COMPND    HMDB0002283
HETATM    1  C1  UNL     1      -8.283   0.494  -0.198  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.446  -0.215   0.851  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.988  -0.117   0.457  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.807  -0.768  -0.871  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.375  -0.721  -1.359  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.960   0.715  -1.479  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.628   0.873  -1.933  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.963   1.339  -0.615  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.224   0.525   0.434  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.270   1.320   1.198  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.027   1.144   1.255  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.708   0.080   0.519  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.761   0.639  -0.411  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.031   0.333  -0.280  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.503  -0.582   0.801  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.132  -1.776   0.185  1.00  0.00           C  
HETATM   17  C16 UNL     1       5.378  -2.166   0.361  1.00  0.00           C  
HETATM   18  C17 UNL     1       6.326  -1.446   1.213  1.00  0.00           C  
HETATM   19  C18 UNL     1       7.538  -0.989   0.416  1.00  0.00           C  
HETATM   20  C19 UNL     1       7.205  -0.062  -0.695  1.00  0.00           C  
HETATM   21  C20 UNL     1       6.602   1.204  -0.235  1.00  0.00           C  
HETATM   22  O2  UNL     1       6.466   1.479   0.970  1.00  0.00           O  
HETATM   23  O3  UNL     1       6.171   2.120  -1.186  1.00  0.00           O  
HETATM   24  H1  UNL     1      -9.010   1.178   0.321  1.00  0.00           H  
HETATM   25  H2  UNL     1      -8.888  -0.206  -0.791  1.00  0.00           H  
HETATM   26  H3  UNL     1      -7.667   1.166  -0.834  1.00  0.00           H  
HETATM   27  H4  UNL     1      -7.632   0.251   1.843  1.00  0.00           H  
HETATM   28  H5  UNL     1      -7.717  -1.284   0.865  1.00  0.00           H  
HETATM   29  H6  UNL     1      -5.368  -0.602   1.253  1.00  0.00           H  
HETATM   30  H7  UNL     1      -5.720   0.950   0.476  1.00  0.00           H  
HETATM   31  H8  UNL     1      -6.434  -0.258  -1.613  1.00  0.00           H  
HETATM   32  H9  UNL     1      -6.128  -1.836  -0.765  1.00  0.00           H  
HETATM   33  H10 UNL     1      -4.310  -1.178  -2.367  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.682  -1.255  -0.700  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.655   1.392  -2.040  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.999   2.419  -0.470  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.822  -0.417   0.089  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.090   0.190   1.130  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.675   2.160   1.795  1.00  0.00           H  
HETATM   40  H17 UNL     1       0.634   1.805   1.868  1.00  0.00           H  
HETATM   41  H18 UNL     1       0.995  -0.802   1.065  1.00  0.00           H  
HETATM   42  H19 UNL     1      -0.047  -0.320  -0.258  1.00  0.00           H  
HETATM   43  H20 UNL     1       1.473   1.316  -1.218  1.00  0.00           H  
HETATM   44  H21 UNL     1       3.744   0.774  -0.995  1.00  0.00           H  
HETATM   45  H22 UNL     1       2.722  -0.852   1.499  1.00  0.00           H  
HETATM   46  H23 UNL     1       4.302  -0.063   1.403  1.00  0.00           H  
HETATM   47  H24 UNL     1       3.525  -2.417  -0.489  1.00  0.00           H  
HETATM   48  H25 UNL     1       5.711  -3.090  -0.170  1.00  0.00           H  
HETATM   49  H26 UNL     1       6.761  -2.222   1.938  1.00  0.00           H  
HETATM   50  H27 UNL     1       5.997  -0.635   1.820  1.00  0.00           H  
HETATM   51  H28 UNL     1       8.138  -1.835   0.034  1.00  0.00           H  
HETATM   52  H29 UNL     1       8.188  -0.444   1.135  1.00  0.00           H  
HETATM   53  H30 UNL     1       6.527  -0.546  -1.452  1.00  0.00           H  
HETATM   54  H31 UNL     1       8.154   0.145  -1.249  1.00  0.00           H  
HETATM   55  H32 UNL     1       6.069   3.093  -0.941  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29   30
CONECT    4    5   31   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   51   52
CONECT   20   21   53   54
CONECT   21   22   22   23
CONECT   23   55
END

HMDB0002283
     RDKit          3D
14R,15S-EpETrE
 55 55  0  0  0  0  0  0  0  0999 V2000
   -8.2830    0.4936   -0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4464   -0.2147    0.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9877   -0.1166    0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8071   -0.7679   -0.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3753   -0.7207   -1.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9595    0.7145   -1.4788 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6275    0.8730   -1.9331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9627    1.3392   -0.6146 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2238    0.5252    0.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2703    1.3200    1.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0266    1.1436    1.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7076    0.0804    0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    0.6394   -0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0307    0.3333   -0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5029   -0.5824    0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1318   -1.7762    0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3776   -2.1657    0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3259   -1.4457    1.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5384   -0.9893    0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2046   -0.0617   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6016    1.2040   -0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4658    1.4788    0.9703 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1711    2.1195   -1.1859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0099    1.1778    0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8884   -0.2065   -0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6666    1.1656   -0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6320    0.2508    1.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7173   -1.2837    0.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3680   -0.6022    1.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7203    0.9504    0.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4337   -0.2584   -1.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1280   -1.8365   -0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3104   -1.1780   -2.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6815   -1.2546   -0.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6547    1.3920   -2.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9989    2.4186   -0.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8225   -0.4168    0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0896    0.1903    1.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6747    2.1604    1.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6344    1.8049    1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9954   -0.8017    1.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0472   -0.3205   -0.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4726    1.3160   -1.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7441    0.7739   -0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7217   -0.8517    1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024   -0.0633    1.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252   -2.4169   -0.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7114   -3.0899   -0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7612   -2.2218    1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9969   -0.6353    1.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1384   -1.8347    0.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1876   -0.4441    1.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5269   -0.5456   -1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1541    0.1447   -1.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0694    3.0930   -0.9413 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  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  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  8  6  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  6
  8 36  1  6
  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
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(14R,15S)-EpETrE	ChEBI
(14R,15S)-Epoxy-(5Z,8Z,11Z)-eicosatrienoic acid	ChEBI
(14R,15S)-Epoxy-(5Z,8Z,11Z)-icosatrienoic acid	ChEBI
14(S),15(R)-EET	ChEBI
14R,15S-Epoxy-5Z,8Z,11Z-eicosatrienoic acid	ChEBI
(14R,15S)-Epoxy-(5Z,8Z,11Z)-eicosatrienoate	Generator
(14R,15S)-Epoxy-(5Z,8Z,11Z)-icosatrienoate	Generator
14R,15S-Epoxy-5Z,8Z,11Z-eicosatrienoate	Generator
14(S),15(R)-Epoxy-(5Z,8Z,11Z)-eicosatrienoate	HMDB
14(S),15(R)-Epoxy-(5Z,8Z,11Z)-eicosatrienoic acid	HMDB
14,15-EET	HMDB
14,15-Epoxy-5,8,11-eicosatrienoic acid	HMDB
14,15-Epoxy-5,8,11-eicosatrienoic acid, (2alpha(5Z,8Z,11Z),3alpha)-isomer	HMDB
14,15-Epoxyeicosatrienoic acid	HMDB
14,15-Oxido-5,8,11-eicosatrienoic acid	HMDB
14R,15S-EpETrE	ChEBI

Chemical Formula

C₂₀H₃₂O₃

Average Molecular Weight

320.4663

Monoisotopic Molecular Weight

320.23514489

IUPAC Name

(5Z,8Z,11Z)-13-[(2R,3S)-3-pentyloxiran-2-yl]trideca-5,8,11-trienoic acid

Traditional Name

14R,15S-EpETrE

CAS Registry Number

98103-48-1

SMILES

CCCCC[C@@H]1O[C@@H]1C\C=C/C\C=C/C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C20H32O3/c1-2-3-12-15-18-19(23-18)16-13-10-8-6-4-5-7-9-11-14-17-20(21)22/h4,6-7,9-10,13,18-19H,2-3,5,8,11-12,14-17H2,1H3,(H,21,22)/b6-4-,9-7-,13-10-/t18-,19+/m0/s1

InChI Key

JBSCUHKPLGKXKH-LLZJRKGESA-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

Epoxyeicosatrienoic acids (LMFA03080001 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)
Cerebrospinal Fluid (CSF) (HMDB: HMDB0002283)

Cellular substructure

Extracellular (HMDB: HMDB0002283)
Membrane (HMDB: HMDB0002283)

Source

Exogenous

Exogenous (HMDB: HMDB0002283)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0002283)

Process

Not Available

Role

Not Available

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	0.00032 g/L	ALOGPS
logP	6.23	ALOGPS
logP	5.65	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.82	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	98.36 m³·mol⁻¹	ChemAxon
Polarizability	38.25 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]+	186.564	31661259
DarkChem	[M-H]-	179.531	31661259
DeepCCS	[M+H]+	188.572	30932474
DeepCCS	[M-H]-	186.214	30932474
DeepCCS	[M-2H]-	219.591	30932474
DeepCCS	[M+Na]+	194.818	30932474
AllCCS	[M+H]+	188.3	32859911
AllCCS	[M+H-H2O]+	185.5	32859911
AllCCS	[M+NH4]+	191.0	32859911
AllCCS	[M+Na]+	191.7	32859911
AllCCS	[M-H]-	188.0	32859911
AllCCS	[M+Na-2H]-	189.6	32859911
AllCCS	[M+HCOO]-	191.6	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.	8.25 minutes	32390414
Predicted by Siyang on May 30, 2022	23.9485 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.85 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	3161.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	589.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	242.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	379.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	691.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1173.7 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	635.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	97.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2231.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	715.2 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	1959.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	842.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	529.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	498.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	596.8 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	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
14R,15S-EpETrE	CCCCC[C@@H]1O[C@@H]1C\C=C/C\C=C/C\C=C/CCCC(O)=O	3780.1	Standard polar	33892256
14R,15S-EpETrE	CCCCC[C@@H]1O[C@@H]1C\C=C/C\C=C/C\C=C/CCCC(O)=O	2311.7	Standard non polar	33892256
14R,15S-EpETrE	CCCCC[C@@H]1O[C@@H]1C\C=C/C\C=C/C\C=C/CCCC(O)=O	2448.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
14R,15S-EpETrE,1TMS,isomer #1	CCCCC[C@@H]1O[C@@H]1C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2508.6	Semi standard non polar	33892256
14R,15S-EpETrE,1TBDMS,isomer #1	CCCCC[C@@H]1O[C@@H]1C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2762.4	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 - 14R,15S-EpETrE GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-7390000000-0a6ea9221818f7ca6b61	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 14R,15S-EpETrE GC-MS (1 TMS) - 70eV, Positive	splash10-00bj-9152000000-75e265bfced30aca2f55	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 14R,15S-EpETrE 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 - 14R,15S-EpETrE 10V, Positive-QTOF	splash10-0udi-1139000000-d1b1217f1a0ab449ee76	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 20V, Positive-QTOF	splash10-0f80-9562000000-3a641d61ec600d27001a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 40V, Positive-QTOF	splash10-0f77-9610000000-4d2f2f7c7445ce34caa9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 10V, Negative-QTOF	splash10-014i-1029000000-03d83d003242098cb3c2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 20V, Negative-QTOF	splash10-0gb9-4159000000-4a32a74e26b6a8978859	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 40V, Negative-QTOF	splash10-052f-9120000000-efc218792d62c8df73a5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 10V, Negative-QTOF	splash10-014i-0009000000-fa339ab07ef5a66d93e2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 20V, Negative-QTOF	splash10-0gb9-2149000000-f932d9bc138901e04dad	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 40V, Negative-QTOF	splash10-052f-9140000000-91f3f678f570fc1a1ff6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 10V, Positive-QTOF	splash10-0uki-2259000000-adfdaf1e87da0a4fbf5f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 20V, Positive-QTOF	splash10-0udr-9375000000-fdf50048f25a924a6bb2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 40V, Positive-QTOF	splash10-00mo-9200000000-f15fc52cfe999f85655e	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)

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	0.000134 +/- 0.000053 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000135 +/- 0.00008 uM	Adult (>18 years old)	Both	Normal	John W. Newman, U...	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

FDB022946

KNApSAcK ID

Not Available

Chemspider ID

4446322

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283201

PDB ID

Not Available

ChEBI ID

132275

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Ennis, Michael D.; Baze, Mark E. Asymmetric total synthesis of 14(R),15(S)-, 14(S),15(R)-, 14(R),15(R)-, and 14(S),15(S)-epoxyeicosatrienoic acids. Tetrahedron Letters (1986), 27(50), 6031-4.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Zosmer A, Elder MG, Sullivan MH: The regulation of arachidonic acid metabolism in human first trimester trophoblast by cyclic AMP. Prostaglandins Other Lipid Mediat. 2003 Apr;71(1-2):43-53. [PubMed:12749593 ]
Zosmer A, Elder MG, Sullivan MH: The production of progesterone and 5,6-epoxyeicosatrienoic acid by human granulosa cells. J Steroid Biochem Mol Biol. 2002 Aug;81(4-5):369-76. [PubMed:12361727 ]
Hasunuma K, Terano T, Tamura Y, Yoshida S: Formation of epoxyeicosatrienoic acids from arachidonic acid by cultured rat aortic smooth muscle cell microsomes. Prostaglandins Leukot Essent Fatty Acids. 1991 Mar;42(3):171-5. [PubMed:1650001 ]

Showing metabocard for 14R,15S-EpETrE (HMDB0002283)

MOL for HMDB0002283 (14R,15S-EpETrE)

3D MOL for HMDB0002283 (14R,15S-EpETrE)

3D SDF for HMDB0002283 (14R,15S-EpETrE)

3D-SDF for HMDB0002283 (14R,15S-EpETrE)

PDB for HMDB0002283 (14R,15S-EpETrE)

3D PDB for HMDB0002283 (14R,15S-EpETrE)

SMILES for HMDB0002283 (14R,15S-EpETrE)

INCHI for HMDB0002283 (14R,15S-EpETrE)

Structure for HMDB0002283 (14R,15S-EpETrE)

3D Structure for HMDB0002283 (14R,15S-EpETrE)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra