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Epoxyeicosatetraenoic acid information


Epoxyeicosatetraenoic acid

17,18-EEQ
Identifiers
CAS Number
  • 17,18-EEQ: 131339-23-6
3D model (JSmol)
  • 5,6-EEQ: Interactive image
  • 8,9-EEQ: Interactive image
  • 11,12-EEQ: Interactive image
  • 14,15-EEQ: Interactive image
  • 17,18-EEQ: Interactive image
ChEBI
  • generic: CHEBI:72852
  • 8,9-EEQ: CHEBI:137193
  • 11,12-EEQ: CHEBI:137267
  • 14,15-EEQ: CHEBI:137269
  • 17,18-EEQ: CHEBI:72853
PubChem CID
  • 17,18-EEQ: 16061089
InChI
  • 5,6-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
  • 8,9-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
  • 11,12-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
  • 14,15-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
  • 17,18-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-
    Key: GPQVVJQEBXAKBJ-JPURVOHMSA-N
SMILES
  • 5,6-EEQ: CC/C=C\C/C=C\C/C=C\C/C=C\CC1C(O1)CCCC(=O)O
  • 8,9-EEQ: CC/C=C\C/C=C\C/C=C\CC1C(O1)C/C=C\CCCC(=O)O
  • 11,12-EEQ: CC/C=C\C/C=C\CC1C(O1)C/C=C\C/C=C\CCCC(=O)O
  • 14,15-EEQ: CC/C=C\CC1C(O1)C/C=C\C/C=C\C/C=C\CCCC(=O)O
  • 17,18-EEQ: CCC1C(O1)C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
Properties
Chemical formula
 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.[1][2]

  1. ^ Spector AA (2009). "Arachidonic acid cytochrome P450 epoxygenase pathway". The Journal of Lipid Research. 50 Suppl (Suppl): S52–6. doi:10.1194/jlr.R800038-JLR200. PMC 2674692. PMID 18952572.
  2. ^ Cite error: The named reference Prostaglandins Other Lipid Mediat 2014. p 18 was invoked but never defined (see the help page).

and 20 Related for: Epoxyeicosatetraenoic acid information

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Epoxyeicosatetraenoic acid

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Epoxyeicosatetraenoic acids (EEQs or EpETEs) are a set of biologically active epoxides that various cell types make by metabolizing the omega 3 fatty...

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Eicosanoid

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14,15-EEQ, and 17,18-EEQ (see Epoxyeicosatetraenoic acid); c) Dihomo-γ-linolenic acid viz., 8,9-epoxy-eicosadienoic acid (8,9-EpEDE), 11,12-EpEDE, and...

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CYP2C9

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epoxydocosapentaenoic acids (EDPs; primarily 19,20-epoxy-eicosapentaenoic acid isomers [i.e. 10,11-EDPs]) and eicosapentaenoic acid to epoxyeicosatetraenoic acids (EEQs...

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CYP1A2

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not been demonstrated. The EDP (epoxydocosapentaenoic acid) and EEQ (epoxyeicosatetraenoic acid) metabolites have a broad range of activities. In various...

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Epoxygenase

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its 17,18-epoxy metabolite (see epoxyeicosatetraenoic acid). 4(Z),7(Z),10(Z),13(Z),16(Z),19(Z)-docosahexaenoic acid (DHA) is metabolized by the same...

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CYP1A1

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not been demonstrated. The EDP (epoxydocosapentaenoic acid) and EEQ (epoxyeicosatetraenoic acid) metabolites have a broad range of activities. In various...

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CYP3A4

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activities including the promotion of certain types of cancers (see epoxyeicosatetraenoic acid). CYP3A4 promotes the growth of various types of human cancer...

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Epoxide

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epoxyeicosatrienoic acids which act as signalling molecules. and similar epoxydocosapentaenoic acids, and epoxyeicosatetraenoic acids.) Ring-opening reactions...

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CYP2E1

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not been demonstrated. The EDP (epoxydocosapentaenoic acid) and EEQ (epoxyeicosatetraenoic acid) metabolites have a broad range of activities. In various...

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Epoxydocosapentaenoic acid

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metabolizes the 20-carbon omega-3 fatty acid, eicosapentaenoic acid (EPA), to epoxyeicosatetraenoic acids (EEQs). CYP epoxygenases similarly convert various other...

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Epoxide hydrolase

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of converting epoxyeicosatrienoic acids (EETs), epoxyeicosatetraenoic acids (EPAs), and epoxydocosapentaenoic acids (DPAs) to their corresponding diols...

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CYP4F12

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(see 20-Hydroxyeicosatetraenoic acid). The EDPs (see Epoxydocosapentaenoic acid) and EEQs (see epoxyeicosatetraenoic acid) have a broad range of activities...

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Regorafenib

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epoxyeicosatrienoic acids (EETs), epoxydocosapentaenoic acids (EDPs), epoxyeicosatetraenoic acids (EEQs), and other epoxy polyunsaturated fatty acids that are made...

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CYP2C8

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epoxydocosapentaenoic acids (also termed EDPs); and 4) eicosapentaenoic acid to various epoxyeicosatetraenoic acids (also termed EEQs). Along with CYP2C8, CYP2C9, CYP2C19...

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CYP2C19

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epoxydocosapentaenoic acids (also termed EDPs); and eicosapentaenoic acid to various epoxyeicosatetraenoic acids (also termed EEQs). Along with CYP2C19, CYP2C8, CYP2C9...

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CYP4A11

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cancer growth (see 20-Hydroxyeicosatetraenoic acid, Epoxyeicosatetraenoic acid, and Epoxydocosapentaenoic acid sections on activities and clinical significance)...

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CYP4F8

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eicosapentaenoic acid, (EPA) to their corresponding epoxides, the epoxydocosapentaenoic acids (EDPs) and epoxyeicosatetraenoic acids (EEQs), respectively...

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CYP2S1

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polyunsaturated fatty acids to their epoxides; for example, the enzyme may metabolize eicosapentaenoic acid to epoxyeicosatetraenoic acids (also termed EEQs)...

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CYP2J2

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epoxydocosapentaenoic acids (also termed EDPs); and eicosapentaenoic acid to various epoxyeicosatetraenoic acids (also termed EEQs). CYP2J2, along with CYP219, CYP2C8...

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CYP2C18

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epoxydocosapentaenoic acids (also termed EDPs); and 4) eicosapentaenoic acid to various epoxyeicosatetraenoic acids (also termed EEQs). While CYP2C19, CYP2C8, CYP2C9, CYP2J2...

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