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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (25) Show 25 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 15:33:17 UTC

Update Date

2022-03-07 02:49:20 UTC

HMDB ID

HMDB0004264

Secondary Accession Numbers

HMDB0011138
HMDB04264
HMDB11138

Metabolite Identification

Common Name

14,15-Epoxy-5,8,11-eicosatrienoic acid

Description

14,15-epoxy-5,8,11-eicosatrienoic acid is an epoxyeicosatrienoic acid (EET), a metabolite of arachidonic acid. The P450 eicosanoids epoxyeicosatrienoic acids (EETs) are endogenous lipid mediators produced by P450 epoxygenases and metabolized through multiple pathways including soluble epoxide hydrolase (sEH). The cytochrome P-450 (P450) monooxygenase pathway includes enzymes of the CYP1A, CYP2B, CYP2C, CYP2E, and CYP2J subfamilies that catalyze the formation of four regioisomeric products, 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid. EETs are produced in brain and perform important biological functions, including protection from ischemic injury. Both light flashes and direct glial stimulation produce vasodilatation mediated by EETs. EETs may be involved in the development of hypertension and endothelial dysfunction in DOCA-salt rats, but not in excessive collagen deposition or electrophysiological abnormalities. EETs have vasodilator and natriuretic effect. Blockade of EET formation is associated with salt-sensitive hypertension. Four regioisomeric cis-EET are primary products of arachidonic acid metabolism by cytochrome P450 epoxygenases. Upon hydration by soluble epoxide hydrolase (sEH), EET are metabolized to dihydroxyeicosatrienoic acids (DHET). These hydration products are more stable and less biologically active than EETs. (PMID: 17494091 , 17468203 , 17434916 , 17406062 , 17361113 , 15581597 ).

Structure

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

HMDB0004264
     RDKit          3D
14,15-Epoxy-5,8,11-eicosatrienoic acid
 55 55  0  0  0  0  0  0  0  0999 V2000
    8.9562    0.9680    0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5806    0.8825   -0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4896    1.1870    0.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1497    1.1096    0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9434   -0.2649   -0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5761   -0.3132   -1.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4372   -1.7205   -1.6726 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -1.0895   -0.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1175   -0.8822   -1.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6318    0.4661   -1.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3663    0.9273   -0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248    0.1238    0.4131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1562   -1.3184    0.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0318   -2.1524    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2886   -1.8336   -0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3752   -2.4235    0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3396   -1.7268    0.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5012   -0.2827    0.5605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8398   -0.0407   -0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1326    1.4005   -0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2271    2.1638    0.9210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3428    3.4187    0.8200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2022    1.6336    2.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8465    1.6535    1.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6828    1.3843   -0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2226   -0.0244    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5129   -0.1351   -0.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5333    1.6152   -1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5484    0.4310    1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6347    2.1734    1.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0616    1.9036   -0.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3859    1.2610    0.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9064   -1.0285    0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6691   -0.5626   -1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4751    0.3419   -2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068   -1.6890    0.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2484   -0.9322   -2.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5409   -1.7467   -1.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2568    1.2726   -1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5118    2.0542   -0.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3705    0.4382    0.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3264    0.5697    1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2298   -1.7267    1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8100   -3.2346    0.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2183   -2.3907   -1.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3826   -0.7938   -0.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3663   -3.4958    0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1372   -2.2354    1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7035    0.2994    0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6309    0.1014    1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8905   -0.6018   -1.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6768   -0.4671    0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0512    1.4877   -0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3224    1.8380   -0.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7879    2.0069    2.9534 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  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
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END


  Mrv0541 02231219552D          

 23 23  0  0  0  0            999 V2000
   23.5551  -10.9636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2861  -15.3907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5716  -16.6282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9677  -11.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1426  -11.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6822  -12.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4282  -12.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3967  -11.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1111  -12.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7137  -11.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8256  -11.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9992  -12.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5401  -12.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9992  -12.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2847  -13.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2847  -14.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9992  -14.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4282  -15.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1426  -15.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9992  -15.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7137  -15.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8572  -15.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5716  -15.8032    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  0  0  0  0
  5  7  1  0  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>
HMDB0004264

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC1OC1C\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-

> <INCHI_KEY>
JBSCUHKPLGKXKH-ILYOTBPNSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.4663

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
38.475903901287786

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z,8Z,11Z)-13-(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>
14,15-epoxyeicosatrienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004264
     RDKit          3D
14,15-Epoxy-5,8,11-eicosatrienoic acid
 55 55  0  0  0  0  0  0  0  0999 V2000
    8.9562    0.9680    0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5806    0.8825   -0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4896    1.1870    0.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1497    1.1096    0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9434   -0.2649   -0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5761   -0.3132   -1.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4372   -1.7205   -1.6726 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -1.0895   -0.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1175   -0.8822   -1.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6318    0.4661   -1.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3663    0.9273   -0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248    0.1238    0.4131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1562   -1.3184    0.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0318   -2.1524    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2886   -1.8336   -0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3752   -2.4235    0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3396   -1.7268    0.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5012   -0.2827    0.5605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8398   -0.0407   -0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1326    1.4005   -0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2271    2.1638    0.9210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3428    3.4187    0.8200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2022    1.6336    2.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8465    1.6535    1.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6828    1.3843   -0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2226   -0.0244    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5129   -0.1351   -0.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5333    1.6152   -1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5484    0.4310    1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6347    2.1734    1.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0616    1.9036   -0.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3859    1.2610    0.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9064   -1.0285    0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6691   -0.5626   -1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4751    0.3419   -2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068   -1.6890    0.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2484   -0.9322   -2.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5409   -1.7467   -1.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2568    1.2726   -1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5118    2.0542   -0.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3705    0.4382    0.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3264    0.5697    1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2298   -1.7267    1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8100   -3.2346    0.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2183   -2.3907   -1.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3826   -0.7938   -0.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3663   -3.4958    0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1372   -2.2354    1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7035    0.2994    0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6309    0.1014    1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8905   -0.6018   -1.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6768   -0.4671    0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0512    1.4877   -0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3224    1.8380   -0.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7879    2.0069    2.9534 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  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
 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      43.970 -20.465   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      47.201 -28.729   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      45.867 -31.039   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      44.740 -21.799   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      43.200 -21.799   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      46.073 -22.569   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      41.866 -22.569   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      47.407 -21.799   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      48.741 -22.569   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      40.532 -21.799   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      50.074 -21.799   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      39.199 -22.569   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      51.408 -22.569   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      39.199 -24.109   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      37.865 -24.879   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      37.865 -26.419   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      39.199 -27.189   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      41.866 -28.729   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      43.200 -29.499   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      39.199 -28.729   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      40.532 -29.499   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      44.533 -28.729   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      45.867 -29.499   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    HMDB0004264
HETATM    1  C1  UNL     1       8.956   0.968   0.450  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.581   0.882  -0.226  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.490   1.187   0.750  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.150   1.110   0.067  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.943  -0.265  -0.474  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.576  -0.313  -1.154  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.437  -1.720  -1.673  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.530  -1.089  -0.683  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.117  -0.882  -1.247  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.632   0.466  -1.017  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.366   0.927  -0.347  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.325   0.124   0.413  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.156  -1.318   0.506  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.032  -2.152   0.044  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.289  -1.834  -0.625  1.00  0.00           C  
HETATM   16  C15 UNL     1      -4.375  -2.423   0.169  1.00  0.00           C  
HETATM   17  C16 UNL     1      -5.340  -1.727   0.684  1.00  0.00           C  
HETATM   18  C17 UNL     1      -5.501  -0.283   0.561  1.00  0.00           C  
HETATM   19  C18 UNL     1      -6.840  -0.041  -0.127  1.00  0.00           C  
HETATM   20  C19 UNL     1      -7.133   1.400  -0.325  1.00  0.00           C  
HETATM   21  C20 UNL     1      -7.227   2.164   0.921  1.00  0.00           C  
HETATM   22  O2  UNL     1      -7.343   3.419   0.820  1.00  0.00           O  
HETATM   23  O3  UNL     1      -7.202   1.634   2.192  1.00  0.00           O  
HETATM   24  H1  UNL     1       8.846   1.653   1.330  1.00  0.00           H  
HETATM   25  H2  UNL     1       9.683   1.384  -0.275  1.00  0.00           H  
HETATM   26  H3  UNL     1       9.223  -0.024   0.826  1.00  0.00           H  
HETATM   27  H4  UNL     1       7.513  -0.135  -0.621  1.00  0.00           H  
HETATM   28  H5  UNL     1       7.533   1.615  -1.064  1.00  0.00           H  
HETATM   29  H6  UNL     1       6.548   0.431   1.588  1.00  0.00           H  
HETATM   30  H7  UNL     1       6.635   2.173   1.256  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.062   1.904  -0.685  1.00  0.00           H  
HETATM   32  H9  UNL     1       4.386   1.261   0.876  1.00  0.00           H  
HETATM   33  H10 UNL     1       4.906  -1.029   0.324  1.00  0.00           H  
HETATM   34  H11 UNL     1       5.669  -0.563  -1.265  1.00  0.00           H  
HETATM   35  H12 UNL     1       3.475   0.342  -2.052  1.00  0.00           H  
HETATM   36  H13 UNL     1       2.607  -1.689   0.250  1.00  0.00           H  
HETATM   37  H14 UNL     1       1.248  -0.932  -2.413  1.00  0.00           H  
HETATM   38  H15 UNL     1       0.541  -1.747  -1.054  1.00  0.00           H  
HETATM   39  H16 UNL     1       1.257   1.273  -1.528  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.512   2.054  -0.348  1.00  0.00           H  
HETATM   41  H18 UNL     1      -2.370   0.438   0.102  1.00  0.00           H  
HETATM   42  H19 UNL     1      -1.326   0.570   1.495  1.00  0.00           H  
HETATM   43  H20 UNL     1      -0.230  -1.727   1.042  1.00  0.00           H  
HETATM   44  H21 UNL     1      -1.810  -3.235   0.165  1.00  0.00           H  
HETATM   45  H22 UNL     1      -3.218  -2.391  -1.640  1.00  0.00           H  
HETATM   46  H23 UNL     1      -3.383  -0.794  -0.877  1.00  0.00           H  
HETATM   47  H24 UNL     1      -4.366  -3.496   0.331  1.00  0.00           H  
HETATM   48  H25 UNL     1      -6.137  -2.235   1.280  1.00  0.00           H  
HETATM   49  H26 UNL     1      -4.703   0.299   0.138  1.00  0.00           H  
HETATM   50  H27 UNL     1      -5.631   0.101   1.616  1.00  0.00           H  
HETATM   51  H28 UNL     1      -6.890  -0.602  -1.081  1.00  0.00           H  
HETATM   52  H29 UNL     1      -7.677  -0.467   0.498  1.00  0.00           H  
HETATM   53  H30 UNL     1      -8.051   1.488  -0.947  1.00  0.00           H  
HETATM   54  H31 UNL     1      -6.322   1.838  -0.983  1.00  0.00           H  
HETATM   55  H32 UNL     1      -7.788   2.007   2.953  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

HMDB0004264
     RDKit          3D
14,15-Epoxy-5,8,11-eicosatrienoic acid
 55 55  0  0  0  0  0  0  0  0999 V2000
    8.9562    0.9680    0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5806    0.8825   -0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4896    1.1870    0.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1497    1.1096    0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9434   -0.2649   -0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5761   -0.3132   -1.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4372   -1.7205   -1.6726 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -1.0895   -0.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1175   -0.8822   -1.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6318    0.4661   -1.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3663    0.9273   -0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248    0.1238    0.4131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1562   -1.3184    0.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0318   -2.1524    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2886   -1.8336   -0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3752   -2.4235    0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3396   -1.7268    0.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5012   -0.2827    0.5605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8398   -0.0407   -0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1326    1.4005   -0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2271    2.1638    0.9210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3428    3.4187    0.8200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2022    1.6336    2.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8465    1.6535    1.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6828    1.3843   -0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2226   -0.0244    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5129   -0.1351   -0.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5333    1.6152   -1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5484    0.4310    1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6347    2.1734    1.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0616    1.9036   -0.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3859    1.2610    0.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9064   -1.0285    0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6691   -0.5626   -1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4751    0.3419   -2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068   -1.6890    0.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2484   -0.9322   -2.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5409   -1.7467   -1.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2568    1.2726   -1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5118    2.0542   -0.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3705    0.4382    0.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3264    0.5697    1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2298   -1.7267    1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8100   -3.2346    0.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2183   -2.3907   -1.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3826   -0.7938   -0.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3663   -3.4958    0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1372   -2.2354    1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7035    0.2994    0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6309    0.1014    1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8905   -0.6018   -1.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6768   -0.4671    0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0512    1.4877   -0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3224    1.8380   -0.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7879    2.0069    2.9534 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  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
 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
(+/-)14,15-epetre	ChEBI
(5Z,8Z,11Z)-14,15-Epoxyeicosa-5.8.11-trienoic acid	ChEBI
(5Z,8Z,11Z)-14,15-Epoxyicosa-5.8.11-trienoic acid	ChEBI
14(15)-EpETrE	ChEBI
14,15-EpETrE	ChEBI
14,15-Epoxy-5Z,8Z,11Z-eicosatrienoic acid	ChEBI
14,15-Epoxy-5Z,8Z,11Z-icosatrienoic acid	ChEBI
all-cis-14,15-Epoxyeicosa-5,8,11-trienoic acid	ChEBI
(5Z,8Z,11Z)-14,15-Epoxyeicosa-5.8.11-trienoate	Generator
(5Z,8Z,11Z)-14,15-Epoxyicosa-5.8.11-trienoate	Generator
14,15-Epoxy-5Z,8Z,11Z-eicosatrienoate	Generator
14,15-Epoxy-5Z,8Z,11Z-icosatrienoate	Generator
all-cis-14,15-Epoxyeicosa-5,8,11-trienoate	Generator
14,15-Epoxy-5,8,11-eicosatrienoate	Generator
14(15)-EpETrE-ea	HMDB
14,15-EET	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

Chemical Formula

C₂₀H₃₂O₃

Average Molecular Weight

320.4663

Monoisotopic Molecular Weight

320.23514489

IUPAC Name

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

Traditional Name

14,15-epoxyeicosatrienoic acid

CAS Registry Number

81276-03-1

SMILES

CCCCCC1OC1C\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-

InChI Key

JBSCUHKPLGKXKH-ILYOTBPNSA-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

EET (CHEBI:34157 )
Hydroxy/hydroperoxyeicosatrienoic acids (C14771 )
Epoxyeicosatrienoic acids (LMFA03080005 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)
Cerebrospinal Fluid (CSF) (HMDB: HMDB0004264)

Cellular substructure

Extracellular (HMDB: HMDB0004264)
Membrane (HMDB: HMDB0004264)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Arachidonic Acid Metabolism (HMDB: HMDB0004264)

Disease pathway

Leukotriene C4 Synthesis Deficiency (PathBank: SMP0000353)

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	187.6	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001865
[M+H]+	Not Available	182.433	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001865

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	38.48 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]+	185.162	31661259
DarkChem	[M-H]-	186.046	31661259
DeepCCS	[M+H]+	185.535	30932474
DeepCCS	[M-H]-	183.177	30932474
DeepCCS	[M-2H]-	216.062	30932474
DeepCCS	[M+Na]+	191.628	30932474
AllCCS	[M+H]+	188.4	32859911
AllCCS	[M+H-H2O]+	185.6	32859911
AllCCS	[M+NH4]+	191.1	32859911
AllCCS	[M+Na]+	191.8	32859911
AllCCS	[M-H]-	188.0	32859911
AllCCS	[M+Na-2H]-	189.6	32859911
AllCCS	[M+HCOO]-	191.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
14,15-Epoxy-5,8,11-eicosatrienoic acid	CCCCCC1OC1C\C=C/C\C=C/C\C=C/CCCC(O)=O	3707.6	Standard polar	33892256
14,15-Epoxy-5,8,11-eicosatrienoic acid	CCCCCC1OC1C\C=C/C\C=C/C\C=C/CCCC(O)=O	2265.0	Standard non polar	33892256
14,15-Epoxy-5,8,11-eicosatrienoic acid	CCCCCC1OC1C\C=C/C\C=C/C\C=C/CCCC(O)=O	2490.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
14,15-Epoxy-5,8,11-eicosatrienoic acid,1TMS,isomer #1	CCCCCC1OC1C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2465.1	Semi standard non polar	33892256
14,15-Epoxy-5,8,11-eicosatrienoic acid,1TBDMS,isomer #1	CCCCCC1OC1C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2716.6	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 - 14,15-Epoxy-5,8,11-eicosatrienoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-7390000000-0a6ea9221818f7ca6b61	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 14,15-Epoxy-5,8,11-eicosatrienoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00bj-9152000000-75e265bfced30aca2f55	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 14,15-Epoxy-5,8,11-eicosatrienoic acid 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 - 14,15-Epoxy-5,8,11-eicosatrienoic acid 10V, Positive-QTOF	splash10-0udi-1139000000-d1b1217f1a0ab449ee76	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14,15-Epoxy-5,8,11-eicosatrienoic acid 20V, Positive-QTOF	splash10-0f80-9562000000-3a641d61ec600d27001a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14,15-Epoxy-5,8,11-eicosatrienoic acid 40V, Positive-QTOF	splash10-0f77-9610000000-4d2f2f7c7445ce34caa9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14,15-Epoxy-5,8,11-eicosatrienoic acid 10V, Negative-QTOF	splash10-014i-1029000000-03d83d003242098cb3c2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14,15-Epoxy-5,8,11-eicosatrienoic acid 20V, Negative-QTOF	splash10-0gb9-4159000000-4a32a74e26b6a8978859	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14,15-Epoxy-5,8,11-eicosatrienoic acid 40V, Negative-QTOF	splash10-052f-9120000000-efc218792d62c8df73a5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14,15-Epoxy-5,8,11-eicosatrienoic acid 10V, Positive-QTOF	splash10-0uki-2259000000-adfdaf1e87da0a4fbf5f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14,15-Epoxy-5,8,11-eicosatrienoic acid 20V, Positive-QTOF	splash10-0udr-9375000000-fdf50048f25a924a6bb2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14,15-Epoxy-5,8,11-eicosatrienoic acid 40V, Positive-QTOF	splash10-00mo-9200000000-f15fc52cfe999f85655e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14,15-Epoxy-5,8,11-eicosatrienoic acid 10V, Negative-QTOF	splash10-014i-0009000000-fa339ab07ef5a66d93e2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14,15-Epoxy-5,8,11-eicosatrienoic acid 20V, Negative-QTOF	splash10-0gb9-2149000000-f932d9bc138901e04dad	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 14,15-Epoxy-5,8,11-eicosatrienoic acid 40V, Negative-QTOF	splash10-052f-9140000000-91f3f678f570fc1a1ff6	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)

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	0.000134 +/- 0.000053 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	0.00175 +/- 0.000043 uM	Adult (>18 years old)	Both	Normal	20671299	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000135 +/- 0.00006 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

FDB023356

KNApSAcK ID

Not Available

Chemspider ID

4446326

KEGG Compound ID

C14771

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283205

PDB ID

Not Available

ChEBI ID

34157

Food Biomarker Ontology

Not Available

VMH ID

C14771

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Only showing the first 10 proteins. There are 25 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

Enzyme Details

4. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

Enzyme Details

5. Cytochrome P450 3A43

General function:: Involved in monooxygenase activity
Specific function:: Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:: CYP3A43
Uniprot ID:: Q9HB55
Molecular weight:: 57756.285

Enzyme Details

6. Cytochrome P450 1B1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:: CYP1B1
Uniprot ID:: Q16678
Molecular weight:: 60845.33

Enzyme Details

7. Cytochrome P450 2C18

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP2C18
Uniprot ID:: P33260
Molecular weight:: 55710.075

Enzyme Details

8. Cytochrome P450 2F1

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: May be involved in the metabolism of various pneumotoxicants including naphthalene. Is able to dealkylate ethoxycoumarin, propoxycoumarin, and pentoxyresorufin but possesses no activity toward ethoxyresorufin and only trace dearylation activity toward benzyloxyresorufin. Bioactivates 3-methylindole (3MI) by dehydrogenation to the putative electrophile 3-methylene-indolenine.
Gene Name:: CYP2F1
Uniprot ID:: P24903
Molecular weight:: 55500.64

Enzyme Details

9. Cytochrome P450 4X1

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: CYP4X1
Uniprot ID:: Q8N118
Molecular weight:: 58874.62

Enzyme Details

10. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

Only showing the first 10 proteins. There are 25 proteins in total.

Show all enzymes and transporters

Showing metabocard for 14,15-Epoxy-5,8,11-eicosatrienoic acid (HMDB0004264)

MOL for HMDB0004264 (14,15-Epoxy-5,8,11-eicosatrienoic acid)

3D MOL for HMDB0004264 (14,15-Epoxy-5,8,11-eicosatrienoic acid)

3D SDF for HMDB0004264 (14,15-Epoxy-5,8,11-eicosatrienoic acid)

3D-SDF for HMDB0004264 (14,15-Epoxy-5,8,11-eicosatrienoic acid)

PDB for HMDB0004264 (14,15-Epoxy-5,8,11-eicosatrienoic acid)

3D PDB for HMDB0004264 (14,15-Epoxy-5,8,11-eicosatrienoic acid)

SMILES for HMDB0004264 (14,15-Epoxy-5,8,11-eicosatrienoic acid)

INCHI for HMDB0004264 (14,15-Epoxy-5,8,11-eicosatrienoic acid)

Structure for HMDB0004264 (14,15-Epoxy-5,8,11-eicosatrienoic acid)

3D Structure for HMDB0004264 (14,15-Epoxy-5,8,11-eicosatrienoic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes