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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (24) Show 24 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-10-19 12:44:39 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005050

Secondary Accession Numbers

HMDB0004683
HMDB04683
HMDB05050

Metabolite Identification

Common Name

15H-11,12-EETA

Description

15H-11,12-EETA is an epoxyeicosatrienoic acid (EET). The role of EETs in 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 hve 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 , 17468203 , 17434916 , 17406062 , 17361113 , 15581597 , 11413051 , 10519554 , 11893556 ).

Structure

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

HMDB0005050
     RDKit          3D
15H-11,12-EETA
 56 56  0  0  0  0  0  0  0  0999 V2000
    8.1844   -1.1657    0.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8119   -0.7027   -0.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7458    0.7987   -1.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7302    1.4305   -0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3765    0.8756   -0.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3598    1.5201    0.4590 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6553    1.2744    1.7897 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0343    0.9309    0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986    0.3604    1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9952   -0.2237    0.6725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1036   -0.5647    1.6858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2320    0.5909    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2799    0.5516   -0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4866    1.3120    0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6655    0.7583    0.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8417   -0.6972    0.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6957   -1.0341   -1.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8071   -1.7387   -0.9635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3817   -2.3020    0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7330   -1.7982    0.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9250   -0.3640    0.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6979    0.5732   -0.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5224    0.3308   -1.3819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6722    1.9490    0.1576 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7074   -2.1577    0.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8926   -0.4899    0.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2386   -1.3251    0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6118   -1.0642   -1.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8329   -1.1467   -1.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5160    1.0031   -2.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7371    1.2394   -0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9610    1.2175    0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7312    2.5305   -0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0411    1.1135   -1.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3101   -0.2019   -0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3312    2.5957    0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8113    0.3008    1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7352    1.0017   -0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6437    0.3171    2.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9706   -0.9014   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1123    1.5477    1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7565    1.1299   -0.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3569   -0.4491   -0.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4238    2.4120    0.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5433    1.3998    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3991   -1.0083    1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9410   -1.3038    0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4197   -0.6938   -2.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3282   -1.9330   -1.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7634   -2.2413    1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5564   -3.4427    0.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4417   -2.0368   -0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2052   -2.4153    1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2847   -0.0887    1.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9847   -0.2440    1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9102    2.6694   -0.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 12 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  1
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END


  Mrv0541 02231220202D          

 24 24  0  0  1  0            999 V2000
   19.0391  -13.8405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4831  -15.7925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1661  -19.9176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5951  -19.9176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4516  -14.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6266  -14.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1661  -14.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9122  -14.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1977  -14.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4831  -14.9675    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.8807  -14.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7687  -14.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0542  -14.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3398  -14.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5951  -14.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6252  -14.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5951  -15.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9107  -14.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3096  -16.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5951  -17.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3096  -17.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5951  -18.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8807  -18.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8807  -19.5051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  6  1  0  0  0  0
 10  2  1  1  0  0  0
  3 24  1  0  0  0  0
  4 24  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 11 15  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005050

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC[C@H](O)\C=C\C1OC1C\C=C/C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-2-3-9-12-17(21)15-16-19-18(24-19)13-10-7-5-4-6-8-11-14-20(22)23/h4,6-7,10,15-19,21H,2-3,5,8-9,11-14H2,1H3,(H,22,23)/b6-4-,10-7-,16-15+/t17-,18?,19?/m0/s1

> <INCHI_KEY>
GELFSVXLSDZDHE-YZSNCDGGSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.4657

> <EXACT_MASS>
336.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
39.47237820166869

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z)-10-{3-[(1E,3S)-3-hydroxyoct-1-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid

> <ALOGPS_LOGP>
5.35

> <JCHEM_LOGP>
4.574270298999999

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.889240084824817

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771840868329

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8472463869138123

> <JCHEM_POLAR_SURFACE_AREA>
70.06

> <JCHEM_REFRACTIVITY>
99.7198

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5Z,8Z)-10-{3-[(1E,3S)-3-hydroxyoct-1-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005050
     RDKit          3D
15H-11,12-EETA
 56 56  0  0  0  0  0  0  0  0999 V2000
    8.1844   -1.1657    0.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8119   -0.7027   -0.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7458    0.7987   -1.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7302    1.4305   -0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3765    0.8756   -0.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3598    1.5201    0.4590 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6553    1.2744    1.7897 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0343    0.9309    0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986    0.3604    1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9952   -0.2237    0.6725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1036   -0.5647    1.6858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2320    0.5909    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2799    0.5516   -0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4866    1.3120    0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6655    0.7583    0.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8417   -0.6972    0.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6957   -1.0341   -1.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8071   -1.7387   -0.9635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3817   -2.3020    0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7330   -1.7982    0.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9250   -0.3640    0.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6979    0.5732   -0.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5224    0.3308   -1.3819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6722    1.9490    0.1576 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7074   -2.1577    0.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8926   -0.4899    0.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2386   -1.3251    0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6118   -1.0642   -1.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8329   -1.1467   -1.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5160    1.0031   -2.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7371    1.2394   -0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9610    1.2175    0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7312    2.5305   -0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0411    1.1135   -1.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3101   -0.2019   -0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3312    2.5957    0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8113    0.3008    1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7352    1.0017   -0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6437    0.3171    2.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9706   -0.9014   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1123    1.5477    1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7565    1.1299   -0.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3569   -0.4491   -0.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4238    2.4120    0.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5433    1.3998    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3991   -1.0083    1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9410   -1.3038    0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4197   -0.6938   -2.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3282   -1.9330   -1.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7634   -2.2413    1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5564   -3.4427    0.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4417   -2.0368   -0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2052   -2.4153    1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2847   -0.0887    1.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9847   -0.2440    1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9102    2.6694   -0.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 12 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  1
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  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      35.540 -25.836   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      30.768 -29.479   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      37.643 -37.180   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      40.311 -37.180   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      36.310 -27.169   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      34.770 -27.169   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      37.643 -27.939   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.436 -27.939   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.102 -27.169   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.768 -27.939   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      38.977 -27.169   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.435 -27.169   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.101 -27.939   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.768 -27.169   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      40.311 -27.939   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.434 -27.939   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      40.311 -29.479   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.100 -27.169   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      41.645 -30.249   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      40.311 -32.559   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      41.645 -31.789   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      40.311 -34.099   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      38.977 -34.870   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      38.977 -36.410   0.000  0.00  0.00           C+0
CONECT    1    5    6                                                       
CONECT    2   10                                                            
CONECT    3   24                                                            
CONECT    4   24                                                            
CONECT    5    1    6    7                                                  
CONECT    6    1    5    8                                                  
CONECT    7    5   11                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    2    9   12                                                  
CONECT   11    7   15                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   16                                                       
CONECT   15   11   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16                                                            
CONECT   19   17   21                                                       
CONECT   20   21   22                                                       
CONECT   21   19   20                                                       
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24    3    4   23                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0005050
HETATM    1  C1  UNL     1       8.184  -1.166   0.425  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.812  -0.703  -0.950  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.746   0.799  -1.093  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.730   1.431  -0.164  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.376   0.876  -0.468  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.360   1.520   0.459  1.00  0.00           C  
HETATM    7  O1  UNL     1       4.655   1.274   1.790  1.00  0.00           O  
HETATM    8  C7  UNL     1       3.034   0.931   0.087  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.299   0.360   1.018  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.995  -0.224   0.673  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.104  -0.565   1.686  1.00  0.00           O  
HETATM   12  C10 UNL     1      -0.232   0.591   1.025  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.280   0.552  -0.073  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.487   1.312   0.200  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.666   0.758   0.267  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.842  -0.697   0.068  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.696  -1.034  -1.069  1.00  0.00           C  
HETATM   18  C16 UNL     1      -5.807  -1.739  -0.964  1.00  0.00           C  
HETATM   19  C17 UNL     1      -6.382  -2.302   0.266  1.00  0.00           C  
HETATM   20  C18 UNL     1      -7.733  -1.798   0.601  1.00  0.00           C  
HETATM   21  C19 UNL     1      -7.925  -0.364   0.884  1.00  0.00           C  
HETATM   22  C20 UNL     1      -7.698   0.573  -0.191  1.00  0.00           C  
HETATM   23  O3  UNL     1      -7.522   0.331  -1.382  1.00  0.00           O  
HETATM   24  O4  UNL     1      -7.672   1.949   0.158  1.00  0.00           O  
HETATM   25  H1  UNL     1       8.707  -2.158   0.325  1.00  0.00           H  
HETATM   26  H2  UNL     1       8.893  -0.490   0.941  1.00  0.00           H  
HETATM   27  H3  UNL     1       7.239  -1.325   0.999  1.00  0.00           H  
HETATM   28  H4  UNL     1       8.612  -1.064  -1.638  1.00  0.00           H  
HETATM   29  H5  UNL     1       6.833  -1.147  -1.251  1.00  0.00           H  
HETATM   30  H6  UNL     1       7.516   1.003  -2.151  1.00  0.00           H  
HETATM   31  H7  UNL     1       8.737   1.239  -0.825  1.00  0.00           H  
HETATM   32  H8  UNL     1       6.961   1.218   0.901  1.00  0.00           H  
HETATM   33  H9  UNL     1       6.731   2.531  -0.277  1.00  0.00           H  
HETATM   34  H10 UNL     1       5.041   1.113  -1.496  1.00  0.00           H  
HETATM   35  H11 UNL     1       5.310  -0.202  -0.301  1.00  0.00           H  
HETATM   36  H12 UNL     1       4.331   2.596   0.267  1.00  0.00           H  
HETATM   37  H13 UNL     1       4.811   0.301   1.947  1.00  0.00           H  
HETATM   38  H14 UNL     1       2.735   1.002  -0.948  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.644   0.317   2.038  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.971  -0.901  -0.205  1.00  0.00           H  
HETATM   41  H17 UNL     1      -0.112   1.548   1.530  1.00  0.00           H  
HETATM   42  H18 UNL     1      -0.757   1.130  -0.925  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.357  -0.449  -0.462  1.00  0.00           H  
HETATM   44  H20 UNL     1      -2.424   2.412   0.362  1.00  0.00           H  
HETATM   45  H21 UNL     1      -4.543   1.400   0.477  1.00  0.00           H  
HETATM   46  H22 UNL     1      -4.399  -1.008   1.018  1.00  0.00           H  
HETATM   47  H23 UNL     1      -2.941  -1.304   0.106  1.00  0.00           H  
HETATM   48  H24 UNL     1      -4.420  -0.694  -2.084  1.00  0.00           H  
HETATM   49  H25 UNL     1      -6.328  -1.933  -1.943  1.00  0.00           H  
HETATM   50  H26 UNL     1      -5.763  -2.241   1.170  1.00  0.00           H  
HETATM   51  H27 UNL     1      -6.556  -3.443   0.079  1.00  0.00           H  
HETATM   52  H28 UNL     1      -8.442  -2.037  -0.273  1.00  0.00           H  
HETATM   53  H29 UNL     1      -8.205  -2.415   1.425  1.00  0.00           H  
HETATM   54  H30 UNL     1      -7.285  -0.089   1.793  1.00  0.00           H  
HETATM   55  H31 UNL     1      -8.985  -0.244   1.304  1.00  0.00           H  
HETATM   56  H32 UNL     1      -7.910   2.669  -0.507  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7    8   36
CONECT    7   37
CONECT    8    9    9   38
CONECT    9   10   39
CONECT   10   11   12   40
CONECT   11   12
CONECT   12   13   41
CONECT   13   14   42   43
CONECT   14   15   15   44
CONECT   15   16   45
CONECT   16   17   46   47
CONECT   17   18   18   48
CONECT   18   19   49
CONECT   19   20   50   51
CONECT   20   21   52   53
CONECT   21   22   54   55
CONECT   22   23   23   24
CONECT   24   56
END

HMDB0005050
     RDKit          3D
15H-11,12-EETA
 56 56  0  0  0  0  0  0  0  0999 V2000
    8.1844   -1.1657    0.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8119   -0.7027   -0.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7458    0.7987   -1.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7302    1.4305   -0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3765    0.8756   -0.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3598    1.5201    0.4590 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6553    1.2744    1.7897 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0343    0.9309    0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986    0.3604    1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9952   -0.2237    0.6725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1036   -0.5647    1.6858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2320    0.5909    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2799    0.5516   -0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4866    1.3120    0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6655    0.7583    0.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8417   -0.6972    0.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6957   -1.0341   -1.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8071   -1.7387   -0.9635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3817   -2.3020    0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7330   -1.7982    0.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9250   -0.3640    0.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6979    0.5732   -0.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5224    0.3308   -1.3819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6722    1.9490    0.1576 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7074   -2.1577    0.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8926   -0.4899    0.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2386   -1.3251    0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6118   -1.0642   -1.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8329   -1.1467   -1.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5160    1.0031   -2.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7371    1.2394   -0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9610    1.2175    0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7312    2.5305   -0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0411    1.1135   -1.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3101   -0.2019   -0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3312    2.5957    0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8113    0.3008    1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7352    1.0017   -0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6437    0.3171    2.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9706   -0.9014   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1123    1.5477    1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7565    1.1299   -0.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3569   -0.4491   -0.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4238    2.4120    0.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5433    1.3998    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3991   -1.0083    1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9410   -1.3038    0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4197   -0.6938   -2.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3282   -1.9330   -1.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7634   -2.2413    1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5564   -3.4427    0.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4417   -2.0368   -0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2052   -2.4153    1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2847   -0.0887    1.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9847   -0.2440    1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9102    2.6694   -0.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 12 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  1
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
15-Hydroxy-11,12-epoxyeicosatrienoic acid	Kegg
(5Z,8Z,13E)-(15S)-11,12-Epoxy-15-hydroxyeicosa-5,8,13-trienoic acid	Kegg
(5Z,8Z,13E)-(15S)-11,12-Epoxy-15-hydroxyicosa-5,8,13-trienoic acid	Kegg
15-Hydroxy-11,12-epoxyeicosatrienoate	Generator
(5Z,8Z,13E)-(15S)-11,12-Epoxy-15-hydroxyeicosa-5,8,13-trienoate	Generator
(5Z,8Z,13E)-(15S)-11,12-Epoxy-15-hydroxyicosa-5,8,13-trienoate	Generator
(+/-)11,12-ep-15(S)-hetre	HMDB
11,12-Epoxy-15S-hydroxy-5Z,8Z,13E-eicosatrienoate	HMDB
11,12-Epoxy-15S-hydroxy-5Z,8Z,13E-eicosatrienoic acid	HMDB
15-H-11,12-EETA	HMDB

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.4657

Monoisotopic Molecular Weight

336.230059512

IUPAC Name

(5Z,8Z)-10-{3-[(1E,3S)-3-hydroxyoct-1-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid

Traditional Name

(5Z,8Z)-10-{3-[(1E,3S)-3-hydroxyoct-1-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid

CAS Registry Number

877878-78-9

SMILES

CCCCC[C@H](O)\C=C\C1OC1C\C=C/C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C20H32O4/c1-2-3-9-12-17(21)15-16-19-18(24-19)13-10-7-5-4-6-8-11-14-20(22)23/h4,6-7,10,15-19,21H,2-3,5,8-9,11-14H2,1H3,(H,22,23)/b6-4-,10-7-,16-15+/t17-,18?,19?/m0/s1

InChI Key

GELFSVXLSDZDHE-YZSNCDGGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Medium-chain hydroxy acids and derivatives

Direct Parent

Medium-chain hydroxy acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

carbonyl compound (CHEBI:34160 )
Epoxyeicosatrienoic acids (C14781 )
Epoxyeicosatrienoic acids (LMFA03080007 )

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	0.011 g/L	ALOGPS
logP	5.35	ALOGPS
logP	4.57	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.06 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	99.72 m³·mol⁻¹	ChemAxon
Polarizability	39.47 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	187.573	31661259
DarkChem	[M-H]-	187.906	31661259
DeepCCS	[M+H]+	190.859	30932474
DeepCCS	[M-H]-	188.501	30932474
DeepCCS	[M-2H]-	221.387	30932474
DeepCCS	[M+Na]+	196.952	30932474
AllCCS	[M+H]+	191.8	32859911
AllCCS	[M+H-H2O]+	189.0	32859911
AllCCS	[M+NH4]+	194.4	32859911
AllCCS	[M+Na]+	195.1	32859911
AllCCS	[M-H]-	190.1	32859911
AllCCS	[M+Na-2H]-	191.8	32859911
AllCCS	[M+HCOO]-	193.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	7.38 minutes	32390414
Predicted by Siyang on May 30, 2022	17.4001 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.94 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	33.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2974.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	301.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	187.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	211.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	458.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	826.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	530.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	122.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1723.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	598.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1650.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	578.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	450.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	329.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	359.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
15H-11,12-EETA	CCCCC[C@H](O)\C=C\C1OC1C\C=C/C\C=C/CCCC(O)=O	3967.4	Standard polar	33892256
15H-11,12-EETA	CCCCC[C@H](O)\C=C\C1OC1C\C=C/C\C=C/CCCC(O)=O	2382.4	Standard non polar	33892256
15H-11,12-EETA	CCCCC[C@H](O)\C=C\C1OC1C\C=C/C\C=C/CCCC(O)=O	2652.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
15H-11,12-EETA,1TMS,isomer #1	CCCCC[C@@H](/C=C/C1OC1C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	2754.8	Semi standard non polar	33892256
15H-11,12-EETA,1TMS,isomer #2	CCCCC[C@H](O)/C=C/C1OC1C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2659.2	Semi standard non polar	33892256
15H-11,12-EETA,2TMS,isomer #1	CCCCC[C@@H](/C=C/C1OC1C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2706.3	Semi standard non polar	33892256
15H-11,12-EETA,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/C1OC1C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	2996.7	Semi standard non polar	33892256
15H-11,12-EETA,1TBDMS,isomer #2	CCCCC[C@H](O)/C=C/C1OC1C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2910.3	Semi standard non polar	33892256
15H-11,12-EETA,2TBDMS,isomer #1	CCCCC[C@@H](/C=C/C1OC1C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3211.0	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 - 15H-11,12-EETA GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-9882000000-3542c00b22d7a628f998	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15H-11,12-EETA GC-MS (2 TMS) - 70eV, Positive	splash10-00vr-9283200000-71f2061c2c545719c5e4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15H-11,12-EETA GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15H-11,12-EETA 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 - 15H-11,12-EETA 10V, Positive-QTOF	splash10-014i-0119000000-6669e73fed08fa686b6e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15H-11,12-EETA 20V, Positive-QTOF	splash10-0g6r-2923000000-e1ebfd6b5b07ef684222	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15H-11,12-EETA 40V, Positive-QTOF	splash10-0a4u-9820000000-9eb24537f07886109c99	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15H-11,12-EETA 10V, Negative-QTOF	splash10-000i-0019000000-5d21765fe08515872649	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15H-11,12-EETA 20V, Negative-QTOF	splash10-014r-2469000000-e74f5db2ba7aafe7ac69	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15H-11,12-EETA 40V, Negative-QTOF	splash10-052f-9600000000-5f3ccdc5aeb81ec5bee7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15H-11,12-EETA 10V, Negative-QTOF	splash10-00kr-0109000000-a81cf651f2bb9ef3b6b6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15H-11,12-EETA 20V, Negative-QTOF	splash10-00kr-0459000000-b65496bff68de53bdb69	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15H-11,12-EETA 40V, Negative-QTOF	splash10-052f-8941000000-395c49b790cb96398dc2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15H-11,12-EETA 10V, Positive-QTOF	splash10-0gb9-0219000000-4a6493bd003dca0bbd4a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15H-11,12-EETA 20V, Positive-QTOF	splash10-0uxr-5519000000-1d89d8ca3789431e87c2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15H-11,12-EETA 40V, Positive-QTOF	splash10-014l-9600000000-db7302e43cd74c6250d3	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

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

Not Available

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

FDB023612

KNApSAcK ID

Not Available

Chemspider ID

10128337

KEGG Compound ID

C14781

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11954042

PDB ID

Not Available

ChEBI ID

34160

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Lipid Maps (LMFA03080007) [Link]

Only showing the first 10 proteins. There are 24 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 24 proteins in total.

Show all enzymes and transporters

Showing metabocard for 15H-11,12-EETA (HMDB0005050)

MOL for HMDB0005050 (15H-11,12-EETA)

3D MOL for HMDB0005050 (15H-11,12-EETA)

3D SDF for HMDB0005050 (15H-11,12-EETA)

3D-SDF for HMDB0005050 (15H-11,12-EETA)

PDB for HMDB0005050 (15H-11,12-EETA)

3D PDB for HMDB0005050 (15H-11,12-EETA)

SMILES for HMDB0005050 (15H-11,12-EETA)

INCHI for HMDB0005050 (15H-11,12-EETA)

Structure for HMDB0005050 (15H-11,12-EETA)

3D Structure for HMDB0005050 (15H-11,12-EETA)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes