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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (27) Show 27 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-14 00:02:12 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004673

Secondary Accession Numbers

HMDB0003978
HMDB0010409
HMDB03978
HMDB04673
HMDB10409

Metabolite Identification

Common Name

11,12-Epoxyeicosatrienoic acid

Description

11,12-Epoxyeicosatrienoic acid (CAS: 81276-02-0) is an epoxyeicosatrienoic acid (EET). Induction of CYP2C8 in native coronary artery endothelial cells by beta-naphthoflavone enhances the formation of 11,12-epoxyeicosatrienoic acid, as well as endothelium-derived hyperpolarizing factor-mediated hyperpolarization and relaxation. Transfection of coronary arteries with CYP2C8 antisense oligonucleotides resulted in decreased levels of CYP2C and attenuated the endothelium-derived hyperpolarizing factor-mediated vascular responses. Thus, a CYP-epoxygenase product is an essential component of the endothelium-derived hyperpolarizing factor-mediated relaxation in the porcine coronary artery, and CYP2C8 fulfills the criteria for the coronary endothelium-derived hyperpolarization factor synthase. The role of EETs in the regulation of the cerebral circulation has become more important since it was realized that EETs are produced in another specialized cell type of the brain, the astrocytes. It has become evident that EETs released from astrocytes may mediate cerebral functional hyperemia. Molecular and pharmacological evidence has shown that neurotransmitter release and spillover onto astrocytes can generate EETs. Since these EETs may reach the vasculature via astrocyte foot-processes, they have the same potential as their endothelial counterparts to hyperpolarize and dilate cerebral vessels. P450 enzymes contain heme in their catalytic domain and nitric oxide (NO) appears to bind to these heme moieties and block formation of P450 products, including EETs. Thus, there appears to be crosstalk between P450 enzymes and NO/NO synthase. The role of fatty acid metabolites and cerebral blood flow becomes even more complex in light of data demonstrating that cyclooxygenase products can act as substrates for P450 enzymes (PMID: 17494091 , 17434916 , 17406062 , 17361113 , 15581597 , 11413051 , 10519554 ). EETs function as autocrine and paracrine mediators. During inflammation, a large amount of arachidonic acid (AA) is released into the cellular milieu and cyclooxygenase enzymes convert this AA to prostaglandins that in turn sensitize pain pathways. However, AA is also converted into natural EETs by cytochrome P450 enzymes. Cytochrome P450 (CYP) epoxygenases convert arachidonic acid into four epoxyeicosatrienoic acid (EET) regioisomers, 5,6-, 8,9-, 11,12-, and 14,15-EET. EETs produce vascular relaxation by activating smooth muscle large-conductance Ca2+-activated K+ channels. In particular, 11,12-epoxy-5Z,8Z,14Z-eicosatrienoic acid has been shown to play a role in the recovery of depleted Ca2+ pools in cultured smooth muscle cells (PMID: 9368016 ). In addition, EETs have anti-inflammatory effects on blood vessels and in the kidney, promote angiogenesis, and protect ischemic myocardium and the brain. EET levels are typically regulated by soluble epoxide hydrolase (sEH), the major enzyme degrading EETs. Specifically, soluble epoxide hydrolase (sEH) converts EETs into dihydroxyeicosatrienoic acids.

Structure

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

HMDB0004673
     RDKit          3D
11,12-Epoxyeicosatrienoic acid
 55 55  0  0  0  0  0  0  0  0999 V2000
   -7.5221    0.1478   -1.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7750   -0.6559    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1031   -1.9676    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6456   -2.0678    0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7488   -1.3918    1.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7662    0.0654    1.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6876    0.8213    0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3800    0.2956    0.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696    0.7972   -0.9557 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8645    2.2130   -1.0980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6820    1.3829   -1.1816 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3503    1.6404   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5145    2.2446   -0.7234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7251    1.7492   -0.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0573    0.4698   -0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0844    0.7509    0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2807    0.2020    0.9850 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7600   -0.7341   -0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9632   -0.2289   -0.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1521    0.0897    0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6832   -1.0492    0.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0545   -1.5001    1.7980 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8853   -1.6220    0.4581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3263   -0.4800   -2.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4278    0.7773   -1.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7188    0.8898   -0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7265   -0.0869    1.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9088   -0.9242    0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3967   -2.4227    1.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6279   -2.6733   -0.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2877   -1.7386   -0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3929   -3.1716    0.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7355   -1.8525    0.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1039   -1.7461    2.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6817    0.5910    1.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8507    1.9180    0.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2423   -0.7698    0.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6255    0.7672    1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012    0.3106   -1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2795    1.3711   -2.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1040    2.4488    0.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807    0.8003    0.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3788    3.1953   -1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5478    2.2711   -1.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2056    0.0266    0.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3487   -0.3088   -0.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8260    1.4363    1.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9605    0.4823    1.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1363   -1.6580    0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -1.1270   -0.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6805    0.6600   -1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2516   -1.0078   -1.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9980    0.4686   -0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9607    0.9795    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7296   -1.0787    0.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 11  9  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
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  6
 11 40  1  6
 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


  Mrv1652303192023122D          

 23 23  0  0  0  0            999 V2000
10007.119210006.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.403610006.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.578610006.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.863010006.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.147310006.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.322410006.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.608810006.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.893210006.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.177510006.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.463910006.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.746210006.5076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.463910007.7448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10007.833010006.9192    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10008.664710006.9192    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10008.248910007.6334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10009.379510006.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.094310006.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.919910006.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.634710006.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.349510006.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.064310006.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.779310006.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.496210006.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
 13  1  1  6  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 14 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004673

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-2-3-4-5-9-12-15-18-19(23-18)16-13-10-7-6-8-11-14-17-20(21)22/h6,8-10,12-13,18-19H,2-5,7,11,14-17H2,1H3,(H,21,22)/b8-6-,12-9-,13-10-/t18-,19+/m1/s1

> <INCHI_KEY>
DXOYQVHGIODESM-LZXKBWHHSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.473

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.653715552458905

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z,8Z)-10-[(2S,3R)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid

> <ALOGPS_LOGP>
6.25

> <JCHEM_LOGP>
5.649173906

> <ALOGPS_LOGS>
-5.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771840930504

> <JCHEM_PKA_STRONGEST_BASIC>
-4.207091543707248

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
98.3583

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.27e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5Z,8Z)-10-[(2S,3R)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004673
     RDKit          3D
11,12-Epoxyeicosatrienoic acid
 55 55  0  0  0  0  0  0  0  0999 V2000
   -7.5221    0.1478   -1.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7750   -0.6559    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1031   -1.9676    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6456   -2.0678    0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7488   -1.3918    1.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7662    0.0654    1.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6876    0.8213    0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3800    0.2956    0.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696    0.7972   -0.9557 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8645    2.2130   -1.0980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6820    1.3829   -1.1816 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3503    1.6404   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5145    2.2446   -0.7234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7251    1.7492   -0.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0573    0.4698   -0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0844    0.7509    0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2807    0.2020    0.9850 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7600   -0.7341   -0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9632   -0.2289   -0.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1521    0.0897    0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6832   -1.0492    0.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0545   -1.5001    1.7980 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8853   -1.6220    0.4581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3263   -0.4800   -2.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4278    0.7773   -1.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7188    0.8898   -0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7265   -0.0869    1.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9088   -0.9242    0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3967   -2.4227    1.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6279   -2.6733   -0.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2877   -1.7386   -0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3929   -3.1716    0.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7355   -1.8525    0.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1039   -1.7461    2.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6817    0.5910    1.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8507    1.9180    0.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2423   -0.7698    0.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6255    0.7672    1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012    0.3106   -1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2795    1.3711   -2.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1040    2.4488    0.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807    0.8003    0.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3788    3.1953   -1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5478    2.2711   -1.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2056    0.0266    0.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3487   -0.3088   -0.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8260    1.4363    1.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9605    0.4823    1.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1363   -1.6580    0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -1.1270   -0.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6805    0.6600   -1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2516   -1.0078   -1.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9980    0.4686   -0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9607    0.9795    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7296   -1.0787    0.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 11  9  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
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  6
 11 40  1  6
 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                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0    8679.9568678.814   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8678.6208679.583   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8677.0808679.583   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8675.7448678.814   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8674.4088679.583   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8672.8688679.583   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8671.5368678.814   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8670.2018679.583   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8668.8658678.814   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8667.5338679.583   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8666.1938678.814   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8667.5338681.124   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8681.2888679.583   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8682.8418679.583   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8682.0658680.916   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    8684.1758678.814   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8685.5098679.583   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8687.0508679.583   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8688.3858678.814   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8689.7198679.583   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8691.0538678.814   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8692.3888679.583   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8693.7268678.814   0.000  0.00  0.00           C+0
CONECT    1    2   13                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    1   14   15                                                  
CONECT   14   16   13   15                                                  
CONECT   15   14   13                                                       
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

COMPND    HMDB0004673
HETATM    1  C1  UNL     1      -7.522   0.148  -1.134  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.775  -0.656   0.114  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.103  -1.968   0.177  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.646  -2.068   0.053  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.749  -1.392   1.010  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.766   0.065   1.053  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.688   0.821   0.783  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.380   0.296   0.419  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.970   0.797  -0.956  1.00  0.00           C  
HETATM   10  O1  UNL     1      -1.865   2.213  -1.098  1.00  0.00           O  
HETATM   11  C10 UNL     1      -0.682   1.383  -1.182  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.350   1.640  -0.104  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.514   2.245  -0.723  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.725   1.749  -0.715  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.057   0.470  -0.047  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.084   0.751   0.996  1.00  0.00           C  
HETATM   17  C16 UNL     1       5.281   0.202   0.985  1.00  0.00           C  
HETATM   18  C17 UNL     1       5.760  -0.734  -0.019  1.00  0.00           C  
HETATM   19  C18 UNL     1       6.963  -0.229  -0.783  1.00  0.00           C  
HETATM   20  C19 UNL     1       8.152   0.090   0.056  1.00  0.00           C  
HETATM   21  C20 UNL     1       8.683  -1.049   0.822  1.00  0.00           C  
HETATM   22  O2  UNL     1       8.055  -1.500   1.798  1.00  0.00           O  
HETATM   23  O3  UNL     1       9.885  -1.622   0.458  1.00  0.00           O  
HETATM   24  H1  UNL     1      -7.326  -0.480  -2.007  1.00  0.00           H  
HETATM   25  H2  UNL     1      -8.428   0.777  -1.371  1.00  0.00           H  
HETATM   26  H3  UNL     1      -6.719   0.890  -0.939  1.00  0.00           H  
HETATM   27  H4  UNL     1      -7.726  -0.087   1.040  1.00  0.00           H  
HETATM   28  H5  UNL     1      -8.909  -0.924   0.037  1.00  0.00           H  
HETATM   29  H6  UNL     1      -7.397  -2.423   1.188  1.00  0.00           H  
HETATM   30  H7  UNL     1      -7.628  -2.673  -0.534  1.00  0.00           H  
HETATM   31  H8  UNL     1      -5.288  -1.739  -0.986  1.00  0.00           H  
HETATM   32  H9  UNL     1      -5.393  -3.172   0.034  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.736  -1.853   0.906  1.00  0.00           H  
HETATM   34  H11 UNL     1      -5.104  -1.746   2.055  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.682   0.591   1.334  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.851   1.918   0.855  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.242  -0.770   0.511  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.626   0.767   1.121  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.501   0.311  -1.787  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.280   1.371  -2.214  1.00  0.00           H  
HETATM   41  H18 UNL     1      -0.104   2.449   0.561  1.00  0.00           H  
HETATM   42  H19 UNL     1       0.481   0.800   0.566  1.00  0.00           H  
HETATM   43  H20 UNL     1       1.379   3.195  -1.244  1.00  0.00           H  
HETATM   44  H21 UNL     1       3.548   2.271  -1.209  1.00  0.00           H  
HETATM   45  H22 UNL     1       2.206   0.027   0.501  1.00  0.00           H  
HETATM   46  H23 UNL     1       3.349  -0.309  -0.775  1.00  0.00           H  
HETATM   47  H24 UNL     1       3.826   1.436   1.793  1.00  0.00           H  
HETATM   48  H25 UNL     1       5.960   0.482   1.807  1.00  0.00           H  
HETATM   49  H26 UNL     1       6.136  -1.658   0.533  1.00  0.00           H  
HETATM   50  H27 UNL     1       5.067  -1.127  -0.748  1.00  0.00           H  
HETATM   51  H28 UNL     1       6.680   0.660  -1.378  1.00  0.00           H  
HETATM   52  H29 UNL     1       7.252  -1.008  -1.545  1.00  0.00           H  
HETATM   53  H30 UNL     1       8.998   0.469  -0.595  1.00  0.00           H  
HETATM   54  H31 UNL     1       7.961   0.980   0.729  1.00  0.00           H  
HETATM   55  H32 UNL     1      10.730  -1.079   0.299  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    7   35
CONECT    7    8   36
CONECT    8    9   37   38
CONECT    9   10   11   39
CONECT   10   11
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

HMDB0004673
     RDKit          3D
11,12-Epoxyeicosatrienoic acid
 55 55  0  0  0  0  0  0  0  0999 V2000
   -7.5221    0.1478   -1.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7750   -0.6559    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1031   -1.9676    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6456   -2.0678    0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7488   -1.3918    1.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7662    0.0654    1.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6876    0.8213    0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3800    0.2956    0.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696    0.7972   -0.9557 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8645    2.2130   -1.0980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6820    1.3829   -1.1816 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3503    1.6404   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5145    2.2446   -0.7234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7251    1.7492   -0.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0573    0.4698   -0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0844    0.7509    0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2807    0.2020    0.9850 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7600   -0.7341   -0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9632   -0.2289   -0.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1521    0.0897    0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6832   -1.0492    0.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0545   -1.5001    1.7980 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8853   -1.6220    0.4581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3263   -0.4800   -2.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4278    0.7773   -1.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7188    0.8898   -0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7265   -0.0869    1.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9088   -0.9242    0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3967   -2.4227    1.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6279   -2.6733   -0.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2877   -1.7386   -0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3929   -3.1716    0.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7355   -1.8525    0.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1039   -1.7461    2.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6817    0.5910    1.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8507    1.9180    0.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2423   -0.7698    0.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6255    0.7672    1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012    0.3106   -1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2795    1.3711   -2.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1040    2.4488    0.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807    0.8003    0.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3788    3.1953   -1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5478    2.2711   -1.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2056    0.0266    0.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3487   -0.3088   -0.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8260    1.4363    1.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9605    0.4823    1.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1363   -1.6580    0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -1.1270   -0.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6805    0.6600   -1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2516   -1.0078   -1.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9980    0.4686   -0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9607    0.9795    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7296   -1.0787    0.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 11  9  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
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  6
 11 40  1  6
 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
(11S,12R)-EpETrE	ChEBI
(11S,12R)-Epoxy-(5Z,8Z,14Z)-eicosatrienoic acid	ChEBI
(11S,12R)-Epoxy-(5Z,8Z,14Z)-icosatrienoic acid	ChEBI
11(S),12(R)-EET	ChEBI
11(S),12(R)-EpETrE	ChEBI
11S,12R-EET	ChEBI
11S,12R-EpETrE	ChEBI
11S,12R-Epoxy-5Z,8Z,14Z-eicosatrienoic acid	ChEBI
(11S,12R)-Epoxy-(5Z,8Z,14Z)-eicosatrienoate	Generator
(11S,12R)-Epoxy-(5Z,8Z,14Z)-icosatrienoate	Generator
11S,12R-Epoxy-5Z,8Z,14Z-eicosatrienoate	Generator
11,12-Epoxyeicosatrienoate	Generator
11,12-Epoxy-5,8,14-eicosatrienoic acid, (2alpha(5Z,8Z),3alpha(Z))-isomer	HMDB
11,12-Oxido-5,8,14-eicosatrienoic acid	HMDB
11(12)-Epoxy-5Z,8Z,14Z-eicosatrienoic acid	HMDB
11,12-EET	HMDB
11,12-Epoxy-5,8,14-eicosatrienoic acid	HMDB
(11S,12R)-Oxidoarachidonic acid	HMDB
(5Z,8Z)-10-[(2S,3R)-3-(2Z)-2-Octen-1-yl-2-oxiranyl]-5,8-decadienoic acid	HMDB
(5Z,8Z)-10-[3-(2Z)-2-Octen-1-yl-2-oxiranyl]-5,8-decadienoic acid	HMDB
10-[3-(2-Octen-1-yl)-2-oxiranyl]-5,8-decadienoic acid	HMDB
10-[3-(2-Octenyl)oxiranyl]-5,8-decadienoic acid	HMDB
11(12)-EET	HMDB
11(12)-EpETrE	HMDB
11,12-Epoxyeicosa-5,8,14-trienoic acid	HMDB
cis-11(12)-EpEtrE	HMDB
11,12-Epoxyeicosatrienoic acid	HMDB

Chemical Formula

C₂₀H₃₂O₃

Average Molecular Weight

320.473

Monoisotopic Molecular Weight

320.23514489

IUPAC Name

(5Z,8Z)-10-[(2S,3R)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid

Traditional Name

(5Z,8Z)-10-[(2S,3R)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid

CAS Registry Number

123931-40-8

SMILES

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

InChI Identifier

InChI=1S/C20H32O3/c1-2-3-4-5-9-12-15-18-19(23-18)16-13-10-7-6-8-11-14-17-20(21)22/h6,8-10,12-13,18-19H,2-5,7,11,14-17H2,1H3,(H,21,22)/b8-6-,12-9-,13-10-/t18-,19+/m1/s1

InChI Key

DXOYQVHGIODESM-LZXKBWHHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hepoxilins. These are eicosanoids containing an oxirane group attached to the fatty acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hepoxilins

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Epoxyeicosatrienoic acids (LMFA03080014 )

Ontology

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	0.00033 g/L	ALOGPS
logP	6.25	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	38.65 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
DeepCCS	[M+H]+	190.076	30932474
DeepCCS	[M-H]-	187.718	30932474
DeepCCS	[M-2H]-	220.604	30932474
DeepCCS	[M+Na]+	196.169	30932474
AllCCS	[M+H]+	188.5	32859911
AllCCS	[M+H-H2O]+	185.7	32859911
AllCCS	[M+NH4]+	191.2	32859911
AllCCS	[M+Na]+	191.9	32859911
AllCCS	[M-H]-	187.8	32859911
AllCCS	[M+Na-2H]-	189.4	32859911
AllCCS	[M+HCOO]-	191.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
11,12-Epoxyeicosatrienoic acid	CCCCC\C=C/C[C@H]1O[C@H]1C\C=C/C\C=C/CCCC(O)=O	3694.5	Standard polar	33892256
11,12-Epoxyeicosatrienoic acid	CCCCC\C=C/C[C@H]1O[C@H]1C\C=C/C\C=C/CCCC(O)=O	2331.0	Standard non polar	33892256
11,12-Epoxyeicosatrienoic acid	CCCCC\C=C/C[C@H]1O[C@H]1C\C=C/C\C=C/CCCC(O)=O	2463.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
11,12-Epoxyeicosatrienoic acid,1TMS,isomer #1	CCCCC/C=C\C[C@H]1O[C@H]1C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2496.7	Semi standard non polar	33892256
11,12-Epoxyeicosatrienoic acid,1TBDMS,isomer #1	CCCCC/C=C\C[C@H]1O[C@H]1C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2748.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 11,12-Epoxyeicosatrienoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11,12-Epoxyeicosatrienoic 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 - 11,12-Epoxyeicosatrienoic acid 10V, Negative-QTOF	splash10-014i-0009000000-8a30f962c830a060bbaa	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12-Epoxyeicosatrienoic acid 20V, Negative-QTOF	splash10-0gb9-0419000000-e44cb44d1b9170384b12	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12-Epoxyeicosatrienoic acid 40V, Negative-QTOF	splash10-0006-9761000000-d3c981434cabe5877633	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12-Epoxyeicosatrienoic acid 10V, Positive-QTOF	splash10-0uki-2339000000-dbc9012403da685e17bf	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12-Epoxyeicosatrienoic acid 20V, Positive-QTOF	splash10-0udu-9645000000-0a0c6b80e626735811c5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11,12-Epoxyeicosatrienoic acid 40V, Positive-QTOF	splash10-05po-9200000000-27dc327d0927da0eb208	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)

Tissue Locations

Epidermis

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	0.000303+/- 0.000023 uM	Adult (>18 years old)	Not Specified	Normal	18953024	details
Blood	Detected and Quantified	0.000303 +/- 0.000028 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.00102 +/- 0.0014 uM	Adult (>18 years old)	Both	Normal	21359215	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00001 +/- 0.00002 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

FDB027560

KNApSAcK ID

Not Available

Chemspider ID

23208913

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

40490664

PDB ID

Not Available

ChEBI ID

132276

Food Biomarker Ontology

Not Available

VMH ID

C14770

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sacerdoti D, Gatta A, McGiff JC: Role of cytochrome P450-dependent arachidonic acid metabolites in liver physiology and pathophysiology. Prostaglandins Other Lipid Mediat. 2003 Oct;72(1-2):51-71. [PubMed:14626496 ]
Catella F, Lawson JA, Fitzgerald DJ, FitzGerald GA: Endogenous biosynthesis of arachidonic acid epoxides in humans: increased formation in pregnancy-induced hypertension. Proc Natl Acad Sci U S A. 1990 Aug;87(15):5893-7. [PubMed:2198572 ]
Fang X, Kaduce TL, VanRollins M, Weintraub NL, Spector AA: Conversion of epoxyeicosatrienoic acids (EETs) to chain-shortened epoxy fatty acids by human skin fibroblasts. J Lipid Res. 2000 Jan;41(1):66-74. [PubMed:10627503 ]
Archer SL, Gragasin FS, Wu X, Wang S, McMurtry S, Kim DH, Platonov M, Koshal A, Hashimoto K, Campbell WB, Falck JR, Michelakis ED: Endothelium-derived hyperpolarizing factor in human internal mammary artery is 11,12-epoxyeicosatrienoic acid and causes relaxation by activating smooth muscle BK(Ca) channels. Circulation. 2003 Feb 11;107(5):769-76. [PubMed:12578883 ]
Potente M, Michaelis UR, Fisslthaler B, Busse R, Fleming I: Cytochrome P450 2C9-induced endothelial cell proliferation involves induction of mitogen-activated protein (MAP) kinase phosphatase-1, inhibition of the c-Jun N-terminal kinase, and up-regulation of cyclin D1. J Biol Chem. 2002 May 3;277(18):15671-6. Epub 2002 Feb 26. [PubMed:11867622 ]
Lundblad MS, Stark K, Eliasson E, Oliw E, Rane A: Biosynthesis of epoxyeicosatrienoic acids varies between polymorphic CYP2C enzymes. Biochem Biophys Res Commun. 2005 Feb 25;327(4):1052-7. [PubMed:15652503 ]
Node K, Huo Y, Ruan X, Yang B, Spiecker M, Ley K, Zeldin DC, Liao JK: Anti-inflammatory properties of cytochrome P450 epoxygenase-derived eicosanoids. Science. 1999 Aug 20;285(5431):1276-9. [PubMed:10455056 ]
Luo G, Zeldin DC, Blaisdell JA, Hodgson E, Goldstein JA: Cloning and expression of murine CYP2Cs and their ability to metabolize arachidonic acid. Arch Biochem Biophys. 1998 Sep 1;357(1):45-57. [PubMed:9721182 ]
Schafer W, Werner K, Schweer H, Schneider J, Zahradnik HP: Formation of cytochrome P450 metabolites of arachidonic acid by human placenta. Adv Exp Med Biol. 1997;433:411-3. [PubMed:9561183 ]
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Potente M, Fisslthaler B, Busse R, Fleming I: 11,12-Epoxyeicosatrienoic acid-induced inhibition of FOXO factors promotes endothelial proliferation by down-regulating p27Kip1. J Biol Chem. 2003 Aug 8;278(32):29619-25. Epub 2003 May 28. [PubMed:12773534 ]
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Fukao M, Mason HS, Kenyon JL, Horowitz B, Keef KD: Regulation of BK(Ca) channels expressed in human embryonic kidney 293 cells by epoxyeicosatrienoic acid. Mol Pharmacol. 2001 Jan;59(1):16-23. [PubMed:11125019 ]
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Spiecker M, Liao JK: Vascular protective effects of cytochrome p450 epoxygenase-derived eicosanoids. Arch Biochem Biophys. 2005 Jan 15;433(2):413-20. [PubMed:15581597 ]
Fleming I, Michaelis UR, Bredenkotter D, Fisslthaler B, Dehghani F, Brandes RP, Busse R: Endothelium-derived hyperpolarizing factor synthase (Cytochrome P450 2C9) is a functionally significant source of reactive oxygen species in coronary arteries. Circ Res. 2001 Jan 19;88(1):44-51. [PubMed:11139472 ]
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Fitzpatrick FA, Ennis MD, Baze ME, Wynalda MA, McGee JE, Liggett WF: Inhibition of cyclooxygenase activity and platelet aggregation by epoxyeicosatrienoic acids. Influence of stereochemistry. J Biol Chem. 1986 Nov 15;261(32):15334-8. [PubMed:3095326 ]
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Arima S, Endo Y, Yaoita H, Omata K, Ogawa S, Tsunoda K, Abe M, Takeuchi K, Abe K, Ito S: Possible role of P-450 metabolite of arachidonic acid in vasodilator mechanism of angiotensin II type 2 receptor in the isolated microperfused rabbit afferent arteriole. J Clin Invest. 1997 Dec 1;100(11):2816-23. [PubMed:9389747 ]
Fisslthaler B, Popp R, Kiss L, Potente M, Harder DR, Fleming I, Busse R: Cytochrome P450 2C is an EDHF synthase in coronary arteries. Nature. 1999 Sep 30;401(6752):493-7. [PubMed:10519554 ]
Zhu Y, Schieber EB, McGiff JC, Balazy M: Identification of arachidonate P-450 metabolites in human platelet phospholipids. Hypertension. 1995 Apr;25(4 Pt 2):854-9. [PubMed:7721444 ]
McGee J, Fitzpatrick F: Enzymatic hydration of leukotriene A4. Purification and characterization of a novel epoxide hydrolase from human erythrocytes. J Biol Chem. 1985 Oct 15;260(23):12832-7. [PubMed:2995393 ]
Catella F, Lawson J, Braden G, Fitzgerald DJ, Shipp E, FitzGerald GA: Biosynthesis of P450 products of arachidonic acid in humans: increased formation in cardiovascular disease. Adv Prostaglandin Thromboxane Leukot Res. 1991;21A:193-6. [PubMed:1705382 ]
Michaelis UR, Falck JR, Schmidt R, Busse R, Fleming I: Cytochrome P4502C9-derived epoxyeicosatrienoic acids induce the expression of cyclooxygenase-2 in endothelial cells. Arterioscler Thromb Vasc Biol. 2005 Feb;25(2):321-6. Epub 2004 Nov 29. [PubMed:15569819 ]
Lu T, Hong MP, Lee HC: Molecular determinants of cardiac K(ATP) channel activation by epoxyeicosatrienoic acids. J Biol Chem. 2005 May 13;280(19):19097-104. Epub 2005 Mar 10. [PubMed:15760904 ]
Larsen BT, Miura H, Hatoum OA, Campbell WB, Hammock BD, Zeldin DC, Falck JR, Gutterman DD: Epoxyeicosatrienoic and dihydroxyeicosatrienoic acids dilate human coronary arterioles via BK(Ca) channels: implications for soluble epoxide hydrolase inhibition. Am J Physiol Heart Circ Physiol. 2006 Feb;290(2):H491-9. Epub 2005 Oct 28. [PubMed:16258029 ]
Campbell WB: New role for epoxyeicosatrienoic acids as anti-inflammatory mediators. Trends Pharmacol Sci. 2000 Apr;21(4):125-7. [PubMed:10740283 ]
Wu S, Chen W, Murphy E, Gabel S, Tomer KB, Foley J, Steenbergen C, Falck JR, Moomaw CR, Zeldin DC: Molecular cloning, expression, and functional significance of a cytochrome P450 highly expressed in rat heart myocytes. J Biol Chem. 1997 May 9;272(19):12551-9. [PubMed:9139707 ]
Muller DN, Theuer J, Shagdarsuren E, Kaergel E, Honeck H, Park JK, Markovic M, Barbosa-Sicard E, Dechend R, Wellner M, Kirsch T, Fiebeler A, Rothe M, Haller H, Luft FC, Schunck WH: A peroxisome proliferator-activated receptor-alpha activator induces renal CYP2C23 activity and protects from angiotensin II-induced renal injury. Am J Pathol. 2004 Feb;164(2):521-32. [PubMed:14742258 ]
Karara A, Dishman E, Jacobson H, Falck JR, Capdevila JH: Arachidonic acid epoxygenase. Stereochemical analysis of the endogenous epoxyeicosatrienoic acids of human kidney cortex. FEBS Lett. 1990 Jul 30;268(1):227-30. [PubMed:2384159 ]
Medhora M, Narayanan J, Harder D: Dual regulation of the cerebral microvasculature by epoxyeicosatrienoic acids. Trends Cardiovasc Med. 2001 Jan;11(1):38-42. [PubMed:11413051 ]
Dray F, Vulliez-Le Normand B, Deroussent A, Briquet I, Gabellec MM, Nakamura S, Wahl LM, Gouyette A, Salahuddin ZS: Active metabolism of arachidonic acid by Kaposi sarcoma cells cultured from lung biopsies (KS-3); identification by HPLC and MS/MS of the predominant metabolite secreted as the 11,12-epoxy-eicosatrienoic acid. Biochim Biophys Acta. 1992 Oct 13;1180(1):83-90. [PubMed:1390946 ]
Michaelis UR, Fisslthaler B, Medhora M, Harder D, Fleming I, Busse R: Cytochrome P450 2C9-derived epoxyeicosatrienoic acids induce angiogenesis via cross-talk with the epidermal growth factor receptor (EGFR). FASEB J. 2003 Apr;17(6):770-2. Epub 2003 Feb 5. [PubMed:12586744 ]
Jacobs ER, Zeldin DC: The lung HETEs (and EETs) up. Am J Physiol Heart Circ Physiol. 2001 Jan;280(1):H1-H10. [PubMed:11123211 ]
Kiss L, Schutte H, Mayer K, Grimm H, Padberg W, Seeger W, Grimminger F: Synthesis of arachidonic acid-derived lipoxygenase and cytochrome P450 products in the intact human lung vasculature. Am J Respir Crit Care Med. 2000 Jun;161(6):1917-23. [PubMed:10852767 ]
Honda HM, Leitinger N, Frankel M, Goldhaber JI, Natarajan R, Nadler JL, Weiss JN, Berliner JA: Induction of monocyte binding to endothelial cells by MM-LDL: role of lipoxygenase metabolites. Arterioscler Thromb Vasc Biol. 1999 Mar;19(3):680-6. [PubMed:10073973 ]
Xiao YF, Ke Q, Seubert JM, Bradbury JA, Graves J, Degraff LM, Falck JR, Krausz K, Gelboin HV, Morgan JP, Zeldin DC: Enhancement of cardiac L-type Ca2+ currents in transgenic mice with cardiac-specific overexpression of CYP2J2. Mol Pharmacol. 2004 Dec;66(6):1607-16. Epub 2004 Sep 10. [PubMed:15361551 ]
Node K, Ruan XL, Dai J, Yang SX, Graham L, Zeldin DC, Liao JK: Activation of Galpha s mediates induction of tissue-type plasminogen activator gene transcription by epoxyeicosatrienoic acids. J Biol Chem. 2001 May 11;276(19):15983-9. Epub 2001 Feb 22. [PubMed:11279071 ]
Fleming I, Fisslthaler B, Michaelis UR, Kiss L, Popp R, Busse R: The coronary endothelium-derived hyperpolarizing factor (EDHF) stimulates multiple signalling pathways and proliferation in vascular cells. Pflugers Arch. 2001 Jul;442(4):511-8. [PubMed:11510882 ]
Falck JR, Reddy LM, Reddy YK, Bondlela M, Krishna UM, Ji Y, Sun J, Liao JK: 11,12-epoxyeicosatrienoic acid (11,12-EET): structural determinants for inhibition of TNF-alpha-induced VCAM-1 expression. Bioorg Med Chem Lett. 2003 Nov 17;13(22):4011-4. [PubMed:14592496 ]
Krotz F, Riexinger T, Buerkle MA, Nithipatikom K, Gloe T, Sohn HY, Campbell WB, Pohl U: Membrane-potential-dependent inhibition of platelet adhesion to endothelial cells by epoxyeicosatrienoic acids. Arterioscler Thromb Vasc Biol. 2004 Mar;24(3):595-600. Epub 2004 Jan 8. [PubMed:14715644 ]
Quilley J, McGiff JC: Is EDHF an epoxyeicosatrienoic acid? Trends Pharmacol Sci. 2000 Apr;21(4):121-4. [PubMed:10740282 ]
Treluyer JM, Benech H, Colin I, Pruvost A, Cheron G, Cresteil T: Ontogenesis of CYP2C-dependent arachidonic acid metabolism in the human liver: relationship with sudden infant death syndrome. Pediatr Res. 2000 May;47(5):677-83. [PubMed:10813596 ]
Kotlikoff MI: EDHF redux: EETs, TRPV4, and Ca2+ sparks. Circ Res. 2005 Dec 9;97(12):1209-10. [PubMed:16339490 ]
Mombouli JV, Holzmann S, Kostner GM, Graier WF: Potentiation of Ca2+ signaling in endothelial cells by 11,12-epoxyeicosatrienoic acid. J Cardiovasc Pharmacol. 1999 May;33(5):779-84. [PubMed:10226866 ]
Ulsaker GA, Teien G: Gas chromatographic-mass spectrometric identification of four triene monoepoxides of arachidonic acid in human plasma. Analyst. 1990 Mar;115(3):259-62. [PubMed:2327589 ]
Michaelis UR, Fisslthaler B, Barbosa-Sicard E, Falck JR, Fleming I, Busse R: Cytochrome P450 epoxygenases 2C8 and 2C9 are implicated in hypoxia-induced endothelial cell migration and angiogenesis. J Cell Sci. 2005 Dec 1;118(Pt 23):5489-98. Epub 2005 Nov 15. [PubMed:16291720 ]
Balazy M, Schieber EB, McGiff JC: Identification of arachidonate epoxides in human platelets. Adv Prostaglandin Thromboxane Leukot Res. 1995;23:199-201. [PubMed:7732834 ]
VanRollins M: Epoxygenase metabolites of docosahexaenoic and eicosapentaenoic acids inhibit platelet aggregation at concentrations below those affecting thromboxane synthesis. J Pharmacol Exp Ther. 1995 Aug;274(2):798-804. [PubMed:7636743 ]
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Hao CM, Breyer MD: Physiologic and pathophysiologic roles of lipid mediators in the kidney. Kidney Int. 2007 Jun;71(11):1105-15. Epub 2007 Mar 14. [PubMed:17361113 ]
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Only showing the first 10 proteins. There are 27 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 4A11

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate, myristate and palmitate. Has little activity toward prostaglandins A1 and E1. Oxidizes arachidonic acid to 20-hydroxyeicosatetraenoic acid (20-HETE).
Gene Name:: CYP4A11
Uniprot ID:: Q02928
Molecular weight:: 59347.31

Reactions

Arachidonic acid + Oxygen + NADPH + Hydrogen Ion → 11,12-Epoxyeicosatrienoic acid + NADP + Water	details

Enzyme Details

2. 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

3. 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

4. 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

5. 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

6. 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

7. 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

8. 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

9. 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

10. Cytochrome P450 4X1

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

Only showing the first 10 proteins. There are 27 proteins in total.

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Showing metabocard for 11,12-Epoxyeicosatrienoic acid (HMDB0004673)

MOL for HMDB0004673 (11,12-Epoxyeicosatrienoic acid)

3D MOL for HMDB0004673 (11,12-Epoxyeicosatrienoic acid)

3D SDF for HMDB0004673 (11,12-Epoxyeicosatrienoic acid)

3D-SDF for HMDB0004673 (11,12-Epoxyeicosatrienoic acid)

PDB for HMDB0004673 (11,12-Epoxyeicosatrienoic acid)

3D PDB for HMDB0004673 (11,12-Epoxyeicosatrienoic acid)

SMILES for HMDB0004673 (11,12-Epoxyeicosatrienoic acid)

INCHI for HMDB0004673 (11,12-Epoxyeicosatrienoic acid)

Structure for HMDB0004673 (11,12-Epoxyeicosatrienoic acid)

3D Structure for HMDB0004673 (11,12-Epoxyeicosatrienoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

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