Epoxyeicosatetraenoic acid

Epoxyeicosatetraenoic acid
17,18-EEQ
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • 67155383
  • (5S,6R)-EEQ: InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h3-4,6-7,9-10,12-13,18-19H,2,5,8,11,14-17H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-
    Key: AKBOADNSBQNXRS-LTKCOYKYSA-N
  • (8S,9R)-EEQ: InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-12-15-18-19(23-18)16-13-10-11-14-17-20(21)22/h3-4,6-7,9-10,12-13,18-19H,2,5,8,11,14-17H2,1H3,(H,21,22)/b4-3-,7-6-,12-9-,13-10-
    Key: YKIOHMXLFWMWKD-JJUYGIQRSA-N
  • (11S,12R)-EEQ: InChI=1S/C20H30O3/c1-2-3-4-5-9-12-15-18-19(23-18)16-13-10-7-6-8-11-14-17-20(21)22/h3-4,6,8-10,12-13,18-19H,2,5,7,11,14-17H2,1H3,(H,21,22)/b4-3-,8-6-,12-9-,13-10-
    Key: QHOKDYBJJBDJGY-BVILWSOJSA-N
  • (14S,15R)-EEQ: InChI=1S/C20H30O3/c1-2-3-12-15-18-19(23-18)16-13-10-8-6-4-5-7-9-11-14-17-20(21)22/h3-4,6-7,9-10,12-13,18-19H,2,5,8,11,14-17H2,1H3,(H,21,22)/b6-4-,9-7-,12-3-,13-10-
    Key: RGZIXZYRGZWDMI-QXBXTPPVSA-N
  • (17S,18R)-EEQ: InChI=1S/C20H30O3/c1-2-18-19(23-18)16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-20(21)22/h3,5-6,8-9,11-12,14,18-19H,2,4,7,10,13,15-17H2,1H3,(H,21,22)/b5-3-,8-6-,11-9-,14-12-/t18-,19+/m1/s1
    Key: GPQVVJQEBXAKBJ-YQLHGUCYSA-N
  • (5R,6S)-EEQ: CC/C=C\C/C=C\C/C=C\C/C=C\CC1[C@H](O1)CCCC(=O)O
  • (5S,6R)-EEQ: CC/C=C\C/C=C\C/C=C\C/C=C\CC1O[C@H]1CCCC(=O)O
  • (8S,9R)-EEQ: CC/C=C\C/C=C\C/C=C\CC1O[C@H]1C/C=C\CCCC(=O)O
  • (11S,12R)-EEQ: CC/C=C\C/C=C\CC1O[C@H]1C/C=C\C/C=C\CCCC(=O)O
  • (14S,15R)-EEQ: CC/C=C\CC1O[C@H]1C/C=C\C/C=C\C/C=C\CCCC(=O)O
  • (17S,18R)-EEQ: CCC1O[C@H]1C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
Properties
C20H30O3
Molar mass 318.457 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Epoxyeicosatetraenoic acids (EEQs or EpETEs) are a set of biologically active epoxides that various cell types make by metabolizing the omega 3 fatty acid, eicosapentaenoic acid (EPA), with certain cytochrome P450 epoxygenases. These epoxygenases can metabolize EPA to as many as 10 epoxides that differ in the site and/or stereoisomer of the epoxide formed; however, the formed EEQs, while differing in potency, often have similar bioactivities and are commonly considered together.

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