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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:45 UTC

Update Date

2022-09-22 17:43:48 UTC

HMDB ID

HMDB0002265

Secondary Accession Numbers

HMDB0002342
HMDB02265
HMDB02342

Metabolite Identification

Common Name

14,15-DiHETrE

Description

14,15-DiHETrE is a Cytochrome P450 (P450) eicosanoid. Eicosanoids generated from arachidonic acid metabolism by cytochrome P450 (P450) enzymes are important autocrine and paracrine factors that have diverse biological functions. P450 eicosanoids are involved in the regulation of vascular tone, renal tubular transport, cardiac contractility, cellular proliferation, and inflammation. Regulation of P450 eicosanoid levels is determined by many factors, including the induction or repression of the P450 enzymes responsible for their formation. Fibrate drugs are part of a diverse group of compounds known as peroxisome proliferators, which also include herbicides and phthalate ester plasticizers. Peroxisome proliferators act via peroxisome proliferator-activated receptor (PPAR). This receptor is a member of the PPAR nuclear receptor family that also consists of the PPAR and PPAR isoforms. PPAR is mainly expressed in the heart, liver, and kidney, whereas the expression of PPAR is predominantly in the adipose tissue. The biological role of PPAR as a lipid sensor has been well established. 14,15-DiHETrE is a potent activators of PPAR and PPAR, shown to induce the binding of PPAR to a peroxisome proliferator response element (PPRE). Furthermore, 14,15-DiHETrE behaves like peroxisome proliferators in that is able to alter apoA-I and apoA-II mRNA expression. 14,15-DiHETrE is the most potent PPARalpha activator in a COS-7 cell expression system producing a 12-fold increase in PPARalpha-mediated luciferase activity. (PMID: 17431031 , 16113065 ).

Structure

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

HMDB0002265
     RDKit          3D
14,15-DiHETrE
 58 57  0  0  0  0  0  0  0  0999 V2000
   -8.0481    1.2545    0.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2654   -0.2115    0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1187   -1.0937    0.8593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9158   -1.0262    0.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1964    0.2730   -0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9591    0.1467   -0.9837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4125   -0.2400   -2.2402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9445   -0.8064   -0.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5623   -0.3422    0.8226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6577   -0.7401   -1.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0791    0.6019   -1.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1174    0.8383   -0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9865   -0.2200   -0.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2062   -0.2535   -1.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4182   -0.0519   -0.6065 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7079    0.2330    0.8141 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167   -0.8748    1.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8103   -0.6998    1.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4253    0.6070    1.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7011    0.7224    1.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4039    0.5086   -0.4131 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6973    0.6403   -1.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1931    1.7681   -1.3881 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3794   -0.4973   -1.5358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9596    1.7064    1.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2165    1.5706    1.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0675    1.7619   -0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6775   -0.4296   -0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1041   -0.4904    1.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5126   -2.1582    0.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8580   -1.0397    1.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501   -1.7717    0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1857   -1.4320   -1.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8866    0.6771    0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8512    1.0526   -0.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5479    1.2003   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8315    0.5165   -2.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3196   -1.8308   -0.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0817   -0.8391    1.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9772   -1.5572   -1.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9735   -0.9050   -2.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6268    1.4870   -1.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5475    1.8520   -0.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2325    0.1039    0.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5285   -1.2034   -0.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0585   -0.4639   -2.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2321   -0.1049   -1.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8489    0.2701    1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2194    1.2194    0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1935   -1.8836    1.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3667   -1.5882    2.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8021    1.4717    1.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8307    0.6443    2.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1078    1.7390    1.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4025   -0.0429    1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7154    1.2793   -0.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0111   -0.5296   -0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2263   -0.8181   -1.0386 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
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 24 58  1  0
M  END


  Mrv0541 02231219272D          

 24 23  0  0  0  0            999 V2000
   27.9588  -18.0213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2442  -20.0838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9588  -13.0712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6732  -14.3087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9588  -18.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6732  -19.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3877  -18.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2442  -19.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1022  -19.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5298  -18.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8167  -18.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8153  -19.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5312  -19.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1008  -18.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1008  -18.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3863  -17.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2442  -15.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5298  -15.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1008  -16.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3863  -16.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2442  -14.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8153  -15.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1008  -15.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9588  -13.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  8  1  0  0  0  0
  3 24  1  0  0  0  0
  4 24  2  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 20  2  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  1  0  0  0  0
 19 20  1  0  0  0  0
 19 23  1  0  0  0  0
 21 24  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002265

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC(O)C(O)C\C=C/C\C=C/C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O4/c1-2-3-12-15-18(21)19(22)16-13-10-8-6-4-5-7-9-11-14-17-20(23)24/h4,6-7,9-10,13,18-19,21-22H,2-3,5,8,11-12,14-17H2,1H3,(H,23,24)/b6-4-,9-7-,13-10-

> <INCHI_KEY>
SYAWGTIVOGUZMM-ILYOTBPNSA-N

> <FORMULA>
C20H34O4

> <MOLECULAR_WEIGHT>
338.4816

> <EXACT_MASS>
338.245709576

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
39.75268244515042

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,11Z)-14,15-dihydroxyicosa-5,8,11-trienoic acid

> <ALOGPS_LOGP>
5.28

> <JCHEM_LOGP>
4.487470333666667

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.874410364003634

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771840139306

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1485196158174507

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
101.8684

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14,15-DiHETrE

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002265
     RDKit          3D
14,15-DiHETrE
 58 57  0  0  0  0  0  0  0  0999 V2000
   -8.0481    1.2545    0.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2654   -0.2115    0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1187   -1.0937    0.8593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9158   -1.0262    0.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1964    0.2730   -0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9591    0.1467   -0.9837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4125   -0.2400   -2.2402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9445   -0.8064   -0.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5623   -0.3422    0.8226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6577   -0.7401   -1.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0791    0.6019   -1.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1174    0.8383   -0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9865   -0.2200   -0.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2062   -0.2535   -1.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4182   -0.0519   -0.6065 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7079    0.2330    0.8141 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167   -0.8748    1.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8103   -0.6998    1.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4253    0.6070    1.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7011    0.7224    1.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4039    0.5086   -0.4131 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6973    0.6403   -1.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1931    1.7681   -1.3881 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3794   -0.4973   -1.5358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9596    1.7064    1.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2165    1.5706    1.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0675    1.7619   -0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6775   -0.4296   -0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1041   -0.4904    1.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5126   -2.1582    0.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8580   -1.0397    1.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501   -1.7717    0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1857   -1.4320   -1.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8866    0.6771    0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8512    1.0526   -0.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5479    1.2003   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8315    0.5165   -2.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3196   -1.8308   -0.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0817   -0.8391    1.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9772   -1.5572   -1.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9735   -0.9050   -2.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6268    1.4870   -1.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5475    1.8520   -0.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2325    0.1039    0.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5285   -1.2034   -0.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0585   -0.4639   -2.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2321   -0.1049   -1.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8489    0.2701    1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2194    1.2194    0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1935   -1.8836    1.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3667   -1.5882    2.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8021    1.4717    1.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8307    0.6443    2.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1078    1.7390    1.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4025   -0.0429    1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7154    1.2793   -0.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0111   -0.5296   -0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2263   -0.8181   -1.0386 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
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 24 58  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      52.190 -33.640   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      50.856 -37.490   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      52.190 -24.400   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      53.523 -26.710   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      52.190 -35.180   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      53.523 -35.950   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      54.857 -35.180   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      50.856 -35.950   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      56.191 -35.950   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      49.522 -35.180   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      57.525 -35.180   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      48.189 -35.950   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      58.858 -35.950   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      46.855 -35.180   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      46.855 -33.640   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      45.521 -32.870   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      50.856 -28.250   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      49.522 -29.020   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      46.855 -30.560   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      45.521 -31.330   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      50.856 -26.710   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      48.189 -28.250   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      46.855 -29.020   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      52.190 -25.940   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    8                                                            
CONECT    3   24                                                            
CONECT    4   24                                                            
CONECT    5    1    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    9                                                       
CONECT    8    2    5   10                                                  
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   20                                                       
CONECT   17   18   21                                                       
CONECT   18   17   22                                                       
CONECT   19   20   23                                                       
CONECT   20   16   19                                                       
CONECT   21   17   24                                                       
CONECT   22   18   23                                                       
CONECT   23   19   22                                                       
CONECT   24    3    4   21                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0002265
HETATM    1  C1  UNL     1      -8.048   1.254   0.619  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.265  -0.212   0.549  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.119  -1.094   0.859  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.916  -1.026   0.007  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.196   0.273  -0.082  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.959   0.147  -0.984  1.00  0.00           C  
HETATM    7  O1  UNL     1      -4.412  -0.240  -2.240  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.945  -0.806  -0.440  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.562  -0.342   0.823  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.658  -0.740  -1.283  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.079   0.602  -1.269  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.117   0.838  -0.798  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.986  -0.220  -0.238  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.206  -0.254  -1.072  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.418  -0.052  -0.607  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.708   0.233   0.814  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.617  -0.875   1.278  1.00  0.00           C  
HETATM   18  C16 UNL     1       5.810  -0.700   1.750  1.00  0.00           C  
HETATM   19  C17 UNL     1       6.425   0.607   1.891  1.00  0.00           C  
HETATM   20  C18 UNL     1       7.701   0.722   1.060  1.00  0.00           C  
HETATM   21  C19 UNL     1       7.404   0.509  -0.413  1.00  0.00           C  
HETATM   22  C20 UNL     1       8.697   0.640  -1.133  1.00  0.00           C  
HETATM   23  O3  UNL     1       9.193   1.768  -1.388  1.00  0.00           O  
HETATM   24  O4  UNL     1       9.379  -0.497  -1.536  1.00  0.00           O  
HETATM   25  H1  UNL     1      -8.960   1.706   1.139  1.00  0.00           H  
HETATM   26  H2  UNL     1      -7.216   1.571   1.273  1.00  0.00           H  
HETATM   27  H3  UNL     1      -8.067   1.762  -0.376  1.00  0.00           H  
HETATM   28  H4  UNL     1      -8.677  -0.430  -0.468  1.00  0.00           H  
HETATM   29  H5  UNL     1      -9.104  -0.490   1.240  1.00  0.00           H  
HETATM   30  H6  UNL     1      -7.513  -2.158   0.765  1.00  0.00           H  
HETATM   31  H7  UNL     1      -6.858  -1.040   1.966  1.00  0.00           H  
HETATM   32  H8  UNL     1      -5.150  -1.772   0.393  1.00  0.00           H  
HETATM   33  H9  UNL     1      -6.186  -1.432  -1.007  1.00  0.00           H  
HETATM   34  H10 UNL     1      -4.887   0.677   0.898  1.00  0.00           H  
HETATM   35  H11 UNL     1      -5.851   1.053  -0.555  1.00  0.00           H  
HETATM   36  H12 UNL     1      -3.548   1.200  -1.043  1.00  0.00           H  
HETATM   37  H13 UNL     1      -4.831   0.517  -2.724  1.00  0.00           H  
HETATM   38  H14 UNL     1      -3.320  -1.831  -0.444  1.00  0.00           H  
HETATM   39  H15 UNL     1      -3.082  -0.839   1.490  1.00  0.00           H  
HETATM   40  H16 UNL     1      -0.977  -1.557  -1.088  1.00  0.00           H  
HETATM   41  H17 UNL     1      -1.973  -0.905  -2.378  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.627   1.487  -1.659  1.00  0.00           H  
HETATM   43  H19 UNL     1       0.548   1.852  -0.793  1.00  0.00           H  
HETATM   44  H20 UNL     1       1.232   0.104   0.813  1.00  0.00           H  
HETATM   45  H21 UNL     1       0.528  -1.203  -0.111  1.00  0.00           H  
HETATM   46  H22 UNL     1       2.058  -0.464  -2.154  1.00  0.00           H  
HETATM   47  H23 UNL     1       4.232  -0.105  -1.336  1.00  0.00           H  
HETATM   48  H24 UNL     1       2.849   0.270   1.485  1.00  0.00           H  
HETATM   49  H25 UNL     1       4.219   1.219   0.886  1.00  0.00           H  
HETATM   50  H26 UNL     1       4.194  -1.884   1.191  1.00  0.00           H  
HETATM   51  H27 UNL     1       6.367  -1.588   2.050  1.00  0.00           H  
HETATM   52  H28 UNL     1       5.802   1.472   1.751  1.00  0.00           H  
HETATM   53  H29 UNL     1       6.831   0.644   2.968  1.00  0.00           H  
HETATM   54  H30 UNL     1       8.108   1.739   1.185  1.00  0.00           H  
HETATM   55  H31 UNL     1       8.403  -0.043   1.404  1.00  0.00           H  
HETATM   56  H32 UNL     1       6.715   1.279  -0.791  1.00  0.00           H  
HETATM   57  H33 UNL     1       7.011  -0.530  -0.579  1.00  0.00           H  
HETATM   58  H34 UNL     1      10.226  -0.818  -1.039  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7    8   36
CONECT    7   37
CONECT    8    9   10   38
CONECT    9   39
CONECT   10   11   40   41
CONECT   11   12   12   42
CONECT   12   13   43
CONECT   13   14   44   45
CONECT   14   15   15   46
CONECT   15   16   47
CONECT   16   17   48   49
CONECT   17   18   18   50
CONECT   18   19   51
CONECT   19   20   52   53
CONECT   20   21   54   55
CONECT   21   22   56   57
CONECT   22   23   23   24
CONECT   24   58
END

HMDB0002265
     RDKit          3D
14,15-DiHETrE
 58 57  0  0  0  0  0  0  0  0999 V2000
   -8.0481    1.2545    0.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2654   -0.2115    0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1187   -1.0937    0.8593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9158   -1.0262    0.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1964    0.2730   -0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9591    0.1467   -0.9837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4125   -0.2400   -2.2402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9445   -0.8064   -0.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5623   -0.3422    0.8226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6577   -0.7401   -1.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0791    0.6019   -1.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1174    0.8383   -0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9865   -0.2200   -0.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2062   -0.2535   -1.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4182   -0.0519   -0.6065 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7079    0.2330    0.8141 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167   -0.8748    1.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8103   -0.6998    1.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4253    0.6070    1.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7011    0.7224    1.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4039    0.5086   -0.4131 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6973    0.6403   -1.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1931    1.7681   -1.3881 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3794   -0.4973   -1.5358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9596    1.7064    1.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2165    1.5706    1.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0675    1.7619   -0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6775   -0.4296   -0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1041   -0.4904    1.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5126   -2.1582    0.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8580   -1.0397    1.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501   -1.7717    0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1857   -1.4320   -1.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8866    0.6771    0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8512    1.0526   -0.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5479    1.2003   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8315    0.5165   -2.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3196   -1.8308   -0.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0817   -0.8391    1.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9772   -1.5572   -1.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9735   -0.9050   -2.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6268    1.4870   -1.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5475    1.8520   -0.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2325    0.1039    0.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5285   -1.2034   -0.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0585   -0.4639   -2.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2321   -0.1049   -1.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8489    0.2701    1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2194    1.2194    0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1935   -1.8836    1.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3667   -1.5882    2.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8021    1.4717    1.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8307    0.6443    2.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1078    1.7390    1.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4025   -0.0429    1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7154    1.2793   -0.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0111   -0.5296   -0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2263   -0.8181   -1.0386 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
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 24 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z,8Z,11Z)-14,15-Dihydroxyeicosa-5,8,11-trienoic acid	ChEBI
(5Z,8Z,11Z)-14,15-Dihydroxyicosa-5,8,11-trienoic acid	ChEBI
14,15-Dihydroxy-5Z,8Z,11Z-eicosatrienoic acid	ChEBI
14,15-Dihydroxyeicosatrienoic acid	ChEBI
(5Z,8Z,11Z)-14,15-Dihydroxyeicosa-5,8,11-trienoate	Generator
(5Z,8Z,11Z)-14,15-Dihydroxyicosa-5,8,11-trienoate	Generator
14,15-Dihydroxy-5Z,8Z,11Z-eicosatrienoate	Generator
14,15-Dihydroxyeicosatrienoate	Generator
(+/-)14,15-dihetre	HMDB
14,15-DHET	HMDB

Chemical Formula

C₂₀H₃₄O₄

Average Molecular Weight

338.4816

Monoisotopic Molecular Weight

338.245709576

IUPAC Name

(5Z,8Z,11Z)-14,15-dihydroxyicosa-5,8,11-trienoic acid

Traditional Name

14,15-DiHETrE

CAS Registry Number

77667-09-5

SMILES

CCCCCC(O)C(O)C\C=C/C\C=C/C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C20H34O4/c1-2-3-12-15-18(21)19(22)16-13-10-8-6-4-5-7-9-11-14-17-20(23)24/h4,6-7,9-10,13,18-19,21-22H,2-3,5,8,11-12,14-17H2,1H3,(H,23,24)/b6-4-,9-7-,13-10-

InChI Key

SYAWGTIVOGUZMM-ILYOTBPNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosatrienoic acids

Alternative Parents

Substituents

Hydroxyeicosatrienoic acid
Long-chain fatty acid
Hydroxy fatty acid
Unsaturated fatty acid
Fatty acid
Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

DHET (CHEBI:63966 )
Hydroxy/hydroperoxyeicosatrienoic acids (C14775 )
Hydroxy/hydroperoxyeicosatrienoic acids (LMFA03050010 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 20671299)
Cerebrospinal Fluid (CSF) (HMDB: HMDB0002265)

Cellular substructure

Extracellular (HMDB: HMDB0002265)
Membrane (HMDB: HMDB0002265)

Source

Exogenous

Exogenous (HMDB: HMDB0002265)

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: HMDB0002265)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Leukotriene C4 Synthesis Deficiency (PathBank: SMP0120510)

Metabolic pathway

Arachidonic Acid Metabolism (PathBank: SMP0087315)

Drug action pathway

Piroxicam Action Pathway (PathBank: SMP0000077)
Acetylsalicylic Acid Action Pathway (PathBank: SMP0000083)
Etodolac Action Pathway (PathBank: SMP0000084)
Ketoprofen Action Pathway (PathBank: SMP0000085)
Ibuprofen Action Pathway (PathBank: SMP0000086)
Rofecoxib Action Pathway (PathBank: SMP0000087)
Diclofenac Action Pathway (PathBank: SMP0000093)
Sulindac Action Pathway (PathBank: SMP0000094)
Celecoxib Action Pathway (PathBank: SMP0000096)
Ketorolac Action Pathway (PathBank: SMP0000098)
Suprofen Action Pathway (PathBank: SMP0000101)
Bromfenac Action Pathway (PathBank: SMP0000102)
Indomethacin Action Pathway (PathBank: SMP0000104)
Mefenamic Acid Action Pathway (PathBank: SMP0000109)
Oxaprozin Action Pathway (PathBank: SMP0000113)
Nabumetone Action Pathway (PathBank: SMP0000114)
Naproxen Action Pathway (PathBank: SMP0000120)
Diflunisal Action Pathway (PathBank: SMP0000289)
Meloxicam Action Pathway (PathBank: SMP0000106)
Valdecoxib Action Pathway (PathBank: SMP0000116)
Antipyrine Action Pathway (PathBank: SMP0000692)
Antrafenine Action Pathway (PathBank: SMP0000693)
Carprofen Action Pathway (PathBank: SMP0000694)
Etoricoxib Action Pathway (PathBank: SMP0000695)
Fenoprofen Action Pathway (PathBank: SMP0000696)
Flurbiprofen Action Pathway (PathBank: SMP0000697)
Magnesium salicylate Action Pathway (PathBank: SMP0000698)
Lumiracoxib Action Pathway (PathBank: SMP0000699)
Lornoxicam Action Pathway (PathBank: SMP0000700)
Phenylbutazone Action Pathway (PathBank: SMP0000701)
Nepafenac Action Pathway (PathBank: SMP0000702)
Trisalicylate-choline Action Pathway (PathBank: SMP0000703)
Tolmetin Action Pathway (PathBank: SMP0000704)
Tiaprofenic Acid Action Pathway (PathBank: SMP0000705)
Tenoxicam Action Pathway (PathBank: SMP0000706)
Salsalate Action Pathway (PathBank: SMP0000707)
Salicylate-sodium Action Pathway (PathBank: SMP0000708)
Salicylic Acid Action Pathway (PathBank: SMP0000709)
Acetaminophen Action Pathway (PathBank: SMP0000710)

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	0.014 g/L	ALOGPS
logP	5.28	ALOGPS
logP	4.49	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	101.87 m³·mol⁻¹	ChemAxon
Polarizability	39.75 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	188.832	31661259
DarkChem	[M-H]-	189.612	31661259
DeepCCS	[M+H]+	193.31	30932474
DeepCCS	[M-H]-	190.952	30932474
DeepCCS	[M-2H]-	223.838	30932474
DeepCCS	[M+Na]+	199.403	30932474
AllCCS	[M+H]+	192.4	32859911
AllCCS	[M+H-H2O]+	189.6	32859911
AllCCS	[M+NH4]+	194.9	32859911
AllCCS	[M+Na]+	195.6	32859911
AllCCS	[M-H]-	189.2	32859911
AllCCS	[M+Na-2H]-	191.2	32859911
AllCCS	[M+HCOO]-	193.5	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.	7.46 minutes	32390414
Predicted by Siyang on May 30, 2022	17.5904 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.31 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	35.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3018.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	290.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	184.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	209.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	501.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	889.7 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	564.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	112.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1638.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	622.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1718.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	562.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	456.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	358.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	339.0 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
14,15-DiHETrE	CCCCCC(O)C(O)C\C=C/C\C=C/C\C=C/CCCC(O)=O	4230.8	Standard polar	33892256
14,15-DiHETrE	CCCCCC(O)C(O)C\C=C/C\C=C/C\C=C/CCCC(O)=O	2401.0	Standard non polar	33892256
14,15-DiHETrE	CCCCCC(O)C(O)C\C=C/C\C=C/C\C=C/CCCC(O)=O	2609.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
14,15-DiHETrE,1TMS,isomer #1	CCCCCC(O[Si](C)(C)C)C(O)C/C=C\C/C=C\C/C=C\CCCC(=O)O	2810.9	Semi standard non polar	33892256
14,15-DiHETrE,1TMS,isomer #2	CCCCCC(O)C(C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	2818.9	Semi standard non polar	33892256
14,15-DiHETrE,1TMS,isomer #3	CCCCCC(O)C(O)C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2723.7	Semi standard non polar	33892256
14,15-DiHETrE,2TMS,isomer #1	CCCCCC(O[Si](C)(C)C)C(C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	2796.2	Semi standard non polar	33892256
14,15-DiHETrE,2TMS,isomer #2	CCCCCC(O[Si](C)(C)C)C(O)C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2741.7	Semi standard non polar	33892256
14,15-DiHETrE,2TMS,isomer #3	CCCCCC(O)C(C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2752.7	Semi standard non polar	33892256
14,15-DiHETrE,3TMS,isomer #1	CCCCCC(O[Si](C)(C)C)C(C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2735.4	Semi standard non polar	33892256
14,15-DiHETrE,1TBDMS,isomer #1	CCCCCC(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\C/C=C\C/C=C\CCCC(=O)O	3065.3	Semi standard non polar	33892256
14,15-DiHETrE,1TBDMS,isomer #2	CCCCCC(O)C(C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3071.4	Semi standard non polar	33892256
14,15-DiHETrE,1TBDMS,isomer #3	CCCCCC(O)C(O)C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2973.3	Semi standard non polar	33892256
14,15-DiHETrE,2TBDMS,isomer #1	CCCCCC(O[Si](C)(C)C(C)(C)C)C(C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3242.5	Semi standard non polar	33892256
14,15-DiHETrE,2TBDMS,isomer #2	CCCCCC(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3215.9	Semi standard non polar	33892256
14,15-DiHETrE,2TBDMS,isomer #3	CCCCCC(O)C(C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3228.4	Semi standard non polar	33892256
14,15-DiHETrE,3TBDMS,isomer #1	CCCCCC(O[Si](C)(C)C(C)(C)C)C(C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3440.1	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Arachidonic Acid Metabolism
Leukotriene C4 Synthesis Deficiency		Not Available
Piroxicam Action Pathway		Not Available
Acetylsalicylic Acid Action Pathway		Not Available
Etodolac Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00122 +/- 0.000705 uM	Adult (>18 years old)	Not Specified	Normal	Oxygenated lipids...	details
Blood	Detected and Quantified	0.001449 +/- 0.000071 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.000714 +/- 0.000031 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.000603 +/- 0.00018 uM	Adult (>18 years old)	Both	Normal	21359215	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00013 +/- 0.00006 uM	Adult (>18 years old)	Both	Normal	John W. Newman, U...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

FDB022935

KNApSAcK ID

Not Available

Chemspider ID

4446271

KEGG Compound ID

C14775

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283147

PDB ID

Not Available

ChEBI ID

63966

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

Ng VY, Huang Y, Reddy LM, Falck JR, Lin ET, Kroetz DL: Cytochrome P450 eicosanoids are activators of peroxisome proliferator-activated receptor alpha. Drug Metab Dispos. 2007 Jul;35(7):1126-34. Epub 2007 Apr 12. [PubMed:17431031 ]
Fang X, Hu S, Xu B, Snyder GD, Harmon S, Yao J, Liu Y, Sangras B, Falck JR, Weintraub NL, Spector AA: 14,15-Dihydroxyeicosatrienoic acid activates peroxisome proliferator-activated receptor-alpha. Am J Physiol Heart Circ Physiol. 2006 Jan;290(1):H55-63. Epub 2005 Aug 19. [PubMed:16113065 ]

Enzymes

Enzyme Details

1. Bifunctional epoxide hydrolase 2

General function:: Involved in catalytic activity
Specific function:: Bifunctional enzyme. The C-terminal domain has epoxide hydrolase activity and acts on epoxides (alkene oxides, oxiranes) and arene oxides. Plays a role in xenobiotic metabolism by degrading potentially toxic epoxides. Also determines steady-state levels of physiological mediators. The N-terminal domain has lipid phosphatase activity, with the highest activity towards threo-9,10-phosphonooxy-hydroxy-octadecanoic acid, followed by erythro-9,10-phosphonooxy-hydroxy-octadecanoic acid, 12-phosphonooxy-octadec-9Z-enoic acid, 12-phosphonooxy-octadec-9E-enoic acid, and p-nitrophenyl phospate.
Gene Name:: EPHX2
Uniprot ID:: P34913
Molecular weight:: 62615.22

Reactions

14,15-Epoxy-5,8,11-eicosatrienoic acid + Water → 14,15-DiHETrE	details

Showing metabocard for 14,15-DiHETrE (HMDB0002265)

MOL for HMDB0002265 (14,15-DiHETrE)

3D MOL for HMDB0002265 (14,15-DiHETrE)

3D SDF for HMDB0002265 (14,15-DiHETrE)

3D-SDF for HMDB0002265 (14,15-DiHETrE)

PDB for HMDB0002265 (14,15-DiHETrE)

3D PDB for HMDB0002265 (14,15-DiHETrE)

SMILES for HMDB0002265 (14,15-DiHETrE)

INCHI for HMDB0002265 (14,15-DiHETrE)

Structure for HMDB0002265 (14,15-DiHETrE)

3D Structure for HMDB0002265 (14,15-DiHETrE)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions