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14,15-epoxy-20-hydroxy-(5Z,8Z,11Z)-icosatrienoic acid |
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CHEBI:138274 |
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14,15-epoxy-20-hydroxy-(5Z,8Z,11Z)-icosatrienoic acid |
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An epoxy(hydroxy)icosatrienoic acid that is (5Z,8Z,11Z)-icosatrienoic acid having the epoxide group across positions 14-15 and the hydroxy substituent located at position 20. |
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This entity has been manually annotated by the ChEBI Team.
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ChemicalBook:CB21431874, eMolecules:10556188, ZINC000038143761 |
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Molfile
XML
SDF
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InChI=1S/C20H32O4/c21-17-13-9-11-15-19-18(24-19)14-10-7-5-3-1-2-4-6-8-12-16-20(22)23/h1,3-4,6-7,10,18-19,21H,2,5,8-9,11-17H2,(H,22,23)/b3-1-,6-4-,10-7- |
BLHHGTASRFNKLG-TVQVUPQZSA-N |
C(CCCO)CC1C(C/C=C\C/C=C\C/C=C\CCCC(O)=O)O1 |
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Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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View more via ChEBI Ontology
Outgoing
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14,15-epoxy-20-hydroxy-(5Z,8Z,11Z)-icosatrienoic acid
(CHEBI:138274)
has functional parent
arachidonic acid
(CHEBI:15843)
14,15-epoxy-20-hydroxy-(5Z,8Z,11Z)-icosatrienoic acid
(CHEBI:138274)
is a
ω-hydroxy-long-chain fatty acid
(CHEBI:140997)
14,15-epoxy-20-hydroxy-(5Z,8Z,11Z)-icosatrienoic acid
(CHEBI:138274)
is a
epoxy(hydroxy)icosatrienoic acid
(CHEBI:138138)
14,15-epoxy-20-hydroxy-(5Z,8Z,11Z)-icosatrienoic acid
(CHEBI:138274)
is conjugate acid of
14,15-epoxy-20-hydroxy-(5Z,8Z,11Z)-icosatrienoate
(CHEBI:137476)
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Incoming
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14,15-epoxy-20-hydroxy-(5Z,8Z,11Z)-icosatrienoate
(CHEBI:137476)
is conjugate base of
14,15-epoxy-20-hydroxy-(5Z,8Z,11Z)-icosatrienoic acid
(CHEBI:138274)
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(5Z,8Z,11Z)-13-[3-(5-hydroxypentyl)oxiran-2-yl]trideca-5,8,11-trienoic acid
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14,15-epoxy-20-hydroxy-(5Z,8Z,11Z)-eicosatrienoic acid
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ChEBI
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20,14(15)-HEET
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ChEBI
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20-hydroxy-14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoic acid
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ChEBI
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20-hydroxy-14,15-epoxy-(5Z,8Z,11Z)-icosatrienoic acid
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ChEBI
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Le Quéré V, Plée-Gautier E, Potin P, Madec S, Salaün JP (2004) Human CYP4F3s are the main catalysts in the oxidation of fatty acid epoxides. Journal of lipid research 45, 1446-1458 [PubMed:15145985] [show Abstract] CYP4F isoforms are involved in the oxidation of important cellular mediators such as leukotriene B4 (LTB4) and prostaglandins. The proinflammatory agent LTB4 and cytotoxic leukotoxins have been associated with several inflammatory diseases. We present evidence that the hydroxylation of Z 9(10)-epoxyoctadecanoic, Z 9(10)-epoxyoctadec-Z 12-enoic, and Z 12(13)-epoxyoctadec-Z 9-enoic acids and that of monoepoxides from arachidonic acid [epoxyeicosatrienoic acid (EET)] is important in the regulation of leukotoxin and EET activity. These three epoxidized derivatives from the C18 family (C18-epoxides) were converted to 18-hydroxy-C18-epoxides by human hepatic microsomes with apparent Km values of between 27.6 and 175 microM. Among recombinant P450 enzymes, CYP4F2 and CYP4F3B catalyzed mainly the omega-hydroxylation of C18-epoxides with an apparent Vmax of between 0.84 and 15.0 min(-1), whereas the apparent Vmax displayed by CYP4F3A, the isoform found in leukocytes, ranged from 3.0 to 21.2 min(-1). The rate of omega-hydroxylation by CYP4A11 was experimentally found to be between 0.3 and 2.7 min(-1). CYP4F2 and CYP4F3 exhibited preferences for omega-hydroxylation of Z 8(9)-EET, whereas human liver microsomes preferred Z 11(12)-EET and, to a lesser extent, Z 8(9)-EET. Moreover, vicinal diol from both C18-epoxides and EETs were omega-hydroxylated by liver microsomes and by CYP4F2 and CYP4F3. These data support the hypothesis that the human CYP4F subfamily is involved in the omega-hydroxylation of fatty acid epoxides. These findings demonstrate that another pathway besides conversion to vicinal diol or chain shortening by beta-oxidation exists for fatty acid epoxide inactivation. |
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