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

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:43 UTC

Update Date

2022-03-07 02:49:14 UTC

HMDB ID

HMDB0002232

Secondary Accession Numbers

HMDB0004672
HMDB02232
HMDB04672

Metabolite Identification

Common Name

8,9-Epoxyeicosatrienoic acid

Description

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

Structure

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

HMDB0002232
     RDKit          3D
8,9-Epoxyeicosatrienoic acid
 55 55  0  0  0  0  0  0  0  0999 V2000
    6.5063    3.0810   -0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2356    2.1453    0.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5081    0.9250    0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728    0.1364   -0.6229 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3752   -1.0605   -0.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1016   -0.6111   -1.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9363   -0.8561   -1.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6981   -1.6424    0.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9932   -0.8057    1.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8158   -1.1117    1.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0889   -2.2947    1.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2234   -1.7811    0.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9441   -1.0037    1.6170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5063   -2.1302    0.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6557   -1.8067   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6816   -0.3652   -0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7148    0.3871    0.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9463   -0.1181    0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1340    0.1161   -0.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5199    1.5126   -0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5735    2.3646   -1.2029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2182    3.4720   -0.6997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0331    2.0140   -2.4205 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7838    4.0776    0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3435    2.6681   -0.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5704    3.1600   -0.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2211    1.8608    1.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5968    2.6801    1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5218    1.2194    0.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3340    0.2289    1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5072    0.7465   -1.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1607   -0.3102   -0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3850   -1.7060   -0.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9321   -1.5288   -1.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1635   -0.0062   -2.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.4689   -1.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7132   -1.8313    0.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3123   -2.6441   -0.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5435    0.1027    1.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3078   -0.4559    2.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1757   -2.8627    2.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4960   -2.9618    0.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9889   -1.1232   -0.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7126   -3.0266    1.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3060   -2.2843   -0.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5813   -2.2999    0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7945    0.1065   -0.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6007    1.4504   -0.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9033   -1.1474    1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1334    0.5178    1.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0099   -0.4258    0.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0134   -0.4864   -1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4825    1.4491   -1.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8987    2.0052    0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7039    2.7293   -3.0786 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  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  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
 14 12  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  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END


  Mrv0541 02231219262D          

 23 23  0  0  0  0            999 V2000
   17.0095   -2.9290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9944   -7.3560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7089   -6.1185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4220   -3.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5970   -3.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1366   -4.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8826   -4.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8511   -3.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1682   -3.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5654   -4.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4537   -4.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5654   -4.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4537   -4.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2798   -5.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4537   -7.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7391   -5.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4537   -6.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1682   -7.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2798   -6.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7391   -6.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1682   -8.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8826   -9.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9944   -6.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2 23  1  0  0  0  0
  3 23  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 16  1  0  0  0  0
 14 19  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 16 20  2  0  0  0  0
 17 20  1  0  0  0  0
 18 21  1  0  0  0  0
 19 23  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002232

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-12-15-18-19(23-18)16-13-10-11-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)/b7-6-,12-9-,13-10-

> <INCHI_KEY>
DBWQSCSXHFNTMO-TYAUOURKSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.4663

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
38.54958923105813

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z)-7-{3-[(2Z,5Z)-undeca-2,5-dien-1-yl]oxiran-2-yl}hept-5-enoic acid

> <ALOGPS_LOGP>
6.25

> <JCHEM_LOGP>
5.649173906

> <ALOGPS_LOGS>
-6.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.460725440501144

> <JCHEM_PKA_STRONGEST_BASIC>
-4.207091544372091

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
98.35829999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.20e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8,9-epoxyeicosatrienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002232
     RDKit          3D
8,9-Epoxyeicosatrienoic acid
 55 55  0  0  0  0  0  0  0  0999 V2000
    6.5063    3.0810   -0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2356    2.1453    0.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5081    0.9250    0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728    0.1364   -0.6229 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3752   -1.0605   -0.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1016   -0.6111   -1.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9363   -0.8561   -1.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6981   -1.6424    0.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9932   -0.8057    1.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8158   -1.1117    1.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0889   -2.2947    1.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2234   -1.7811    0.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9441   -1.0037    1.6170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5063   -2.1302    0.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6557   -1.8067   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6816   -0.3652   -0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7148    0.3871    0.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9463   -0.1181    0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1340    0.1161   -0.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5199    1.5126   -0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5735    2.3646   -1.2029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2182    3.4720   -0.6997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0331    2.0140   -2.4205 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7838    4.0776    0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3435    2.6681   -0.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5704    3.1600   -0.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2211    1.8608    1.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5968    2.6801    1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5218    1.2194    0.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3340    0.2289    1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5072    0.7465   -1.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1607   -0.3102   -0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3850   -1.7060   -0.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9321   -1.5288   -1.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1635   -0.0062   -2.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.4689   -1.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7132   -1.8313    0.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3123   -2.6441   -0.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5435    0.1027    1.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3078   -0.4559    2.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1757   -2.8627    2.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4960   -2.9618    0.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9889   -1.1232   -0.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7126   -3.0266    1.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3060   -2.2843   -0.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5813   -2.2999    0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7945    0.1065   -0.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6007    1.4504   -0.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9033   -1.1474    1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1334    0.5178    1.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0099   -0.4258    0.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0134   -0.4864   -1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4825    1.4491   -1.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8987    2.0052    0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7039    2.7293   -3.0786 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  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  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
 14 12  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  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      31.751  -5.467   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      39.189 -13.731   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      40.523 -11.421   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      32.521  -6.801   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.981  -6.801   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.855  -7.571   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.648  -7.571   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      35.189  -6.801   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      28.314  -6.801   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      36.522  -7.571   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.980  -7.571   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      36.522  -9.111   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.980  -9.111   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.856  -9.881   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.980 -13.731   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.646  -9.881   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.980 -12.191   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.314 -14.501   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      37.856 -11.421   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.646 -11.421   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.314 -16.041   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      29.648 -16.811   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      39.189 -12.191   0.000  0.00  0.00           C+0
CONECT    1    4    5                                                       
CONECT    2   23                                                            
CONECT    3   23                                                            
CONECT    4    1    5    6                                                  
CONECT    5    1    4    7                                                  
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   16                                                       
CONECT   14   12   19                                                       
CONECT   15   17   18                                                       
CONECT   16   13   20                                                       
CONECT   17   15   20                                                       
CONECT   18   15   21                                                       
CONECT   19   14   23                                                       
CONECT   20   16   17                                                       
CONECT   21   18   22                                                       
CONECT   22   21                                                            
CONECT   23    2    3   19                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

COMPND    HMDB0002232
HETATM    1  C1  UNL     1       6.506   3.081  -0.283  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.236   2.145   0.884  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.508   0.925   0.406  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.273   0.136  -0.623  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.375  -1.060  -0.993  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.102  -0.611  -1.545  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.936  -0.856  -1.053  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.698  -1.642   0.169  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.993  -0.806   1.143  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.816  -1.112   1.595  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.089  -2.295   1.188  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.223  -1.781   0.555  1.00  0.00           C  
HETATM   13  O1  UNL     1      -1.944  -1.004   1.617  1.00  0.00           O  
HETATM   14  C13 UNL     1      -2.506  -2.130   0.950  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.656  -1.807  -0.015  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.682  -0.365  -0.237  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.715   0.387   0.064  1.00  0.00           C  
HETATM   18  C17 UNL     1      -5.946  -0.118   0.648  1.00  0.00           C  
HETATM   19  C18 UNL     1      -7.134   0.116  -0.207  1.00  0.00           C  
HETATM   20  C19 UNL     1      -7.520   1.513  -0.502  1.00  0.00           C  
HETATM   21  C20 UNL     1      -6.573   2.365  -1.203  1.00  0.00           C  
HETATM   22  O2  UNL     1      -6.218   3.472  -0.700  1.00  0.00           O  
HETATM   23  O3  UNL     1      -6.033   2.014  -2.421  1.00  0.00           O  
HETATM   24  H1  UNL     1       6.784   4.078   0.093  1.00  0.00           H  
HETATM   25  H2  UNL     1       7.343   2.668  -0.856  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.570   3.160  -0.879  1.00  0.00           H  
HETATM   27  H4  UNL     1       7.221   1.861   1.326  1.00  0.00           H  
HETATM   28  H5  UNL     1       5.597   2.680   1.611  1.00  0.00           H  
HETATM   29  H6  UNL     1       4.522   1.219   0.008  1.00  0.00           H  
HETATM   30  H7  UNL     1       5.334   0.229   1.265  1.00  0.00           H  
HETATM   31  H8  UNL     1       6.507   0.747  -1.502  1.00  0.00           H  
HETATM   32  H9  UNL     1       7.161  -0.310  -0.132  1.00  0.00           H  
HETATM   33  H10 UNL     1       5.385  -1.706  -0.130  1.00  0.00           H  
HETATM   34  H11 UNL     1       5.932  -1.529  -1.869  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.164  -0.006  -2.471  1.00  0.00           H  
HETATM   36  H13 UNL     1       2.031  -0.469  -1.551  1.00  0.00           H  
HETATM   37  H14 UNL     1       3.713  -1.831   0.641  1.00  0.00           H  
HETATM   38  H15 UNL     1       2.312  -2.644  -0.016  1.00  0.00           H  
HETATM   39  H16 UNL     1       2.543   0.103   1.460  1.00  0.00           H  
HETATM   40  H17 UNL     1       0.308  -0.456   2.334  1.00  0.00           H  
HETATM   41  H18 UNL     1      -0.176  -2.863   2.135  1.00  0.00           H  
HETATM   42  H19 UNL     1       0.496  -2.962   0.451  1.00  0.00           H  
HETATM   43  H20 UNL     1      -0.989  -1.123  -0.320  1.00  0.00           H  
HETATM   44  H21 UNL     1      -2.713  -3.027   1.574  1.00  0.00           H  
HETATM   45  H22 UNL     1      -3.306  -2.284  -0.991  1.00  0.00           H  
HETATM   46  H23 UNL     1      -4.581  -2.300   0.241  1.00  0.00           H  
HETATM   47  H24 UNL     1      -2.794   0.106  -0.674  1.00  0.00           H  
HETATM   48  H25 UNL     1      -4.601   1.450  -0.140  1.00  0.00           H  
HETATM   49  H26 UNL     1      -5.903  -1.147   1.068  1.00  0.00           H  
HETATM   50  H27 UNL     1      -6.133   0.518   1.593  1.00  0.00           H  
HETATM   51  H28 UNL     1      -8.010  -0.426   0.279  1.00  0.00           H  
HETATM   52  H29 UNL     1      -7.013  -0.486  -1.169  1.00  0.00           H  
HETATM   53  H30 UNL     1      -8.482   1.449  -1.112  1.00  0.00           H  
HETATM   54  H31 UNL     1      -7.899   2.005   0.451  1.00  0.00           H  
HETATM   55  H32 UNL     1      -5.704   2.729  -3.079  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   10   39
CONECT   10   11   40
CONECT   11   12   41   42
CONECT   12   13   14   43
CONECT   13   14
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

HMDB0002232
     RDKit          3D
8,9-Epoxyeicosatrienoic acid
 55 55  0  0  0  0  0  0  0  0999 V2000
    6.5063    3.0810   -0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2356    2.1453    0.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5081    0.9250    0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728    0.1364   -0.6229 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3752   -1.0605   -0.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1016   -0.6111   -1.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9363   -0.8561   -1.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6981   -1.6424    0.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9932   -0.8057    1.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8158   -1.1117    1.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0889   -2.2947    1.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2234   -1.7811    0.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9441   -1.0037    1.6170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5063   -2.1302    0.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6557   -1.8067   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6816   -0.3652   -0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7148    0.3871    0.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9463   -0.1181    0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1340    0.1161   -0.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5199    1.5126   -0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5735    2.3646   -1.2029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2182    3.4720   -0.6997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0331    2.0140   -2.4205 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7838    4.0776    0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3435    2.6681   -0.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5704    3.1600   -0.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2211    1.8608    1.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5968    2.6801    1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5218    1.2194    0.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3340    0.2289    1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5072    0.7465   -1.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1607   -0.3102   -0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3850   -1.7060   -0.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9321   -1.5288   -1.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1635   -0.0062   -2.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.4689   -1.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7132   -1.8313    0.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3123   -2.6441   -0.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5435    0.1027    1.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3078   -0.4559    2.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1757   -2.8627    2.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4960   -2.9618    0.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9889   -1.1232   -0.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7126   -3.0266    1.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3060   -2.2843   -0.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5813   -2.2999    0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7945    0.1065   -0.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6007    1.4504   -0.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9033   -1.1474    1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1334    0.5178    1.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0099   -0.4258    0.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0134   -0.4864   -1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4825    1.4491   -1.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8987    2.0052    0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7039    2.7293   -3.0786 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  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  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
 14 12  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  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 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
(+/-)8,9-epetre	ChEBI
(5Z,11Z,14Z)-8,9-Epoxyeicosa-5,11,14-trienoic acid	ChEBI
(5Z,11Z,14Z)-8,9-Epoxyicosa-5,11,14-trienoic acid	ChEBI
8,9-Epoxy-5Z,11Z,14Z-eicosatrienoic acid	ChEBI
8,9-Epoxy-5Z,11Z,14Z-icosatrienoic acid	ChEBI
8,9-Epoxyicosatrienoic acid	ChEBI
(5Z,11Z,14Z)-8,9-Epoxyeicosa-5,11,14-trienoate	Generator
(5Z,11Z,14Z)-8,9-Epoxyicosa-5,11,14-trienoate	Generator
8,9-Epoxy-5Z,11Z,14Z-eicosatrienoate	Generator
8,9-Epoxy-5Z,11Z,14Z-icosatrienoate	Generator
8,9-Epoxyicosatrienoate	Generator
8,9-Epoxyeicosatrienoate	Generator
8,9-Eet	HMDB
8,9-Epoxyeicosatrienoic acid, (2alpha(Z),3alpha(2Z,5Z))-isomer	HMDB

Chemical Formula

C₂₀H₃₂O₃

Average Molecular Weight

320.4663

Monoisotopic Molecular Weight

320.23514489

IUPAC Name

(5Z)-7-{3-[(2Z,5Z)-undeca-2,5-dien-1-yl]oxiran-2-yl}hept-5-enoic acid

Traditional Name

8,9-epoxyeicosatrienoic acid

CAS Registry Number

81246-85-7

SMILES

CCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-12-15-18-19(23-18)16-13-10-11-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)/b7-6-,12-9-,13-10-

InChI Key

DBWQSCSXHFNTMO-TYAUOURKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

EET (CHEBI:34490 )
Hydroxy/hydroperoxyeicosatrienoic acids (C14769 )
Epoxyeicosatrienoic acids (LMFA03080003 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)

Cellular substructure

Extracellular (HMDB: HMDB0002232)
Membrane (HMDB: HMDB0002232)

Source

Exogenous

Exogenous (HMDB: HMDB0002232)

Food

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0002232)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Leukotriene C4 Synthesis Deficiency (PathBank: SMP0120510)

Metabolic pathway

Arachidonic Acid Metabolism (PathBank: SMP0087315)

Drug action pathway

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

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	184.633	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001862

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00032 g/L	ALOGPS
logP	6.25	ALOGPS
logP	5.65	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.46	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	38.55 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	185.81	31661259
DarkChem	[M-H]-	185.008	31661259
DeepCCS	[M+H]+	185.327	30932474
DeepCCS	[M-H]-	182.969	30932474
DeepCCS	[M-2H]-	215.855	30932474
DeepCCS	[M+Na]+	191.42	30932474
AllCCS	[M+H]+	188.7	32859911
AllCCS	[M+H-H2O]+	185.9	32859911
AllCCS	[M+NH4]+	191.4	32859911
AllCCS	[M+Na]+	192.1	32859911
AllCCS	[M-H]-	187.8	32859911
AllCCS	[M+Na-2H]-	189.4	32859911
AllCCS	[M+HCOO]-	191.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	8.21 minutes	32390414
Predicted by Siyang on May 30, 2022	23.1633 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	33.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3134.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	557.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	232.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	341.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	668.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1121.2 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	586.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	105.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2176.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	697.8 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	1890.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	815.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	526.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	484.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	600.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8,9-Epoxyeicosatrienoic acid	CCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(O)=O	3593.7	Standard polar	33892256
8,9-Epoxyeicosatrienoic acid	CCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(O)=O	2300.3	Standard non polar	33892256
8,9-Epoxyeicosatrienoic acid	CCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(O)=O	2499.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8,9-Epoxyeicosatrienoic acid,1TMS,isomer #1	CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)O[Si](C)(C)C	2480.2	Semi standard non polar	33892256
8,9-Epoxyeicosatrienoic acid,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2724.0	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 - 8,9-Epoxyeicosatrienoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000g-6980000000-07a990c3a66cfc7764e5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8,9-Epoxyeicosatrienoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-002r-9553000000-120e27beab70feb84ed6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8,9-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 - 8,9-Epoxyeicosatrienoic acid 10V, Positive-QTOF	splash10-0udi-0229000000-4a7644f998116e5959aa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 20V, Positive-QTOF	splash10-0wn9-4921000000-727677e385ebbb995864	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 40V, Positive-QTOF	splash10-015d-9500000000-903e4e69e6bda087561b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 10V, Negative-QTOF	splash10-014i-0219000000-80c9ec974d3aaabbc8b9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 20V, Negative-QTOF	splash10-0gdi-1539000000-c3f531539781dda28168	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 40V, Negative-QTOF	splash10-052f-9800000000-a8abb16134374c498d9d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 10V, Positive-QTOF	splash10-0uk9-4429000000-e15c713039784fb91bd6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 20V, Positive-QTOF	splash10-0fsi-9413000000-c06fd94936bbbdd11dd3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 40V, Positive-QTOF	splash10-05qc-9200000000-fd86608717f334cda9ba	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 10V, Negative-QTOF	splash10-014i-0009000000-5afdb8d651d23c147e45	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 20V, Negative-QTOF	splash10-014i-0329000000-417e0056d0fd313e5a7b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Epoxyeicosatrienoic acid 40V, Negative-QTOF	splash10-052f-9311000000-bae1c492ade35c452642	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

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

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	<0.0002 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.000627 +/- 0.00071 uM	Adult (>18 years old)	Both	Normal	21359215	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

FDB022920

KNApSAcK ID

Not Available

Chemspider ID

4446324

KEGG Compound ID

C14769

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283203

PDB ID

Not Available

ChEBI ID

34490

Food Biomarker Ontology

Not Available

VMH ID

C14769

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Fritscher LG, Post M, Rodrigues MT, Silverman F, Balter M, Chapman KR, Zamel N: Profile of eicosanoids in breath condensate in asthma and COPD. J Breath Res. 2012 Jun;6(2):026001. doi: 10.1088/1752-7155/6/2/026001. Epub 2012 Mar 27. [PubMed:22451217 ]

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

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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

Enzyme Details

2. Cytochrome P450 2C9

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

Enzyme Details

3. Cytochrome P450 2C19

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

Enzyme Details

4. Cytochrome P450 2E1

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

Enzyme Details

5. Cytochrome P450 3A43

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

Enzyme Details

6. Cytochrome P450 1B1

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

Enzyme Details

7. Cytochrome P450 2C18

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

Enzyme Details

8. Cytochrome P450 2F1

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

Enzyme Details

9. Cytochrome P450 4X1

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

Enzyme Details

10. Cytochrome P450 2B6

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

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

Show all enzymes and transporters

Showing metabocard for 8,9-Epoxyeicosatrienoic acid (HMDB0002232)

MOL for HMDB0002232 (8,9-Epoxyeicosatrienoic acid)

3D MOL for HMDB0002232 (8,9-Epoxyeicosatrienoic acid)

3D SDF for HMDB0002232 (8,9-Epoxyeicosatrienoic acid)

3D-SDF for HMDB0002232 (8,9-Epoxyeicosatrienoic acid)

PDB for HMDB0002232 (8,9-Epoxyeicosatrienoic acid)

3D PDB for HMDB0002232 (8,9-Epoxyeicosatrienoic acid)

SMILES for HMDB0002232 (8,9-Epoxyeicosatrienoic acid)

INCHI for HMDB0002232 (8,9-Epoxyeicosatrienoic acid)

Structure for HMDB0002232 (8,9-Epoxyeicosatrienoic acid)

3D Structure for HMDB0002232 (8,9-Epoxyeicosatrienoic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes