InChI=1S/C20H32O3/c1-2-3-12-15-18-19(23-18)16-13-10-8-6-4-5-7-9-11-14-17-20(21)22/h4,6-7,9-10,13,18-19H,2-3,5,8,11-12,14-17H2,1H3,(H,21,22)/b6-4-,9-7-,13-10-/t18-,19+/m1/s1 |
JBSCUHKPLGKXKH-KZTFMOQPSA-N |
C(CCC)C[C@@H]1[C@H](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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mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via 14,15-EET )
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via EET )
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platelet aggregation inhibitor
A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
(via EET )
anti-inflammatory drug
A substance that reduces or suppresses inflammation.
(via EET )
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View more via ChEBI Ontology
Outgoing
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(14S,15R)-EET
(CHEBI:132274)
is a
14,15-EET
(CHEBI:34157)
(14S,15R)-EET
(CHEBI:132274)
is conjugate acid of
(14S,15R)-EET(1−)
(CHEBI:131964)
(14S,15R)-EET
(CHEBI:132274)
is enantiomer of
(14R,15S)-EET
(CHEBI:132275)
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Incoming
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(14S,15R)-EET(1−)
(CHEBI:131964)
is conjugate base of
(14S,15R)-EET
(CHEBI:132274)
(14R,15S)-EET
(CHEBI:132275)
is enantiomer of
(14S,15R)-EET
(CHEBI:132274)
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(5Z,8Z,11Z)-13-[(2S,3R)-3-pentyloxiran-2-yl]trideca-5,8,11-trienoic acid
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(14S,15R)-EpETrE
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ChEBI
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(14S,15R)-epoxy-(5Z,8Z,11Z)-eicosatrienoic acid
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ChEBI
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(14S,15R)-epoxy-(5Z,8Z,11Z)-icosatrienoic acid
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ChEBI
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14S,15R-EET
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LIPID MAPS
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14S,15R-EpETrE
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LIPID MAPS
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14S,15R-epoxy-5Z,8Z,11Z-eicosatrienoic acid
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LIPID MAPS
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4703442
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Reaxys Registry Number
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Reaxys
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Ladd PA, Du L, Capdevila JH, Mernaugh R, Keeney DS (2003) Epoxyeicosatrienoic acids activate transglutaminases in situ and induce cornification of epidermal keratinocytes. The Journal of biological chemistry 278, 35184-35192 [PubMed:12840027] [show Abstract] The cytochrome P450 CYP2B19 is a keratinocyte-specific arachidonic acid epoxygenase expressed in the granular cell layer of mouse epidermis. In cultured keratinocytes, CYP2B19 mRNAs are up-regulated coordinately with those of profilaggrin, another granular cell-specific marker. We investigated effects of the CYP2B19 metabolites 11,12- and 14,15-epoxyeicosatrienoic acids (EETs) on keratinocyte transglutaminase activities and cornified cell envelope formation. Keratinocytes were differentiated in vitro in the presence of biotinylated cadaverine. Transglutaminases cross-linked this substrate into endogenous proteins in situ; an enzyme-linked immunosorbent assay was used to quantify the biotinylated proteins. Exogenously added or endogenously formed 14,15-EET increased transglutaminase cross-linking activities in cultured human and mouse epidermal keratinocytes in a modified in situ assay. Transglutaminase activities increased approximately 8-fold (p < or = 0.02 versus mock control) in human keratinocytes transduced with adenovirus particles expressing a 14S,15R-EET epoxygenase (P450 BM3v). The physiological transglutaminase substrate involucrin was preferentially biotinylated in situ, determined by immunoblotting and mass spectrometry. P450 BM3v-induced transglutaminase activation was associated with increased 14,15-EET formation (p = 0.002) and spontaneous cell cornification (p < or = 0.001). Preferential involucrin biotinylation and the increased cornified cell envelope formation provided evidence that transglutaminases mediated the P450 BM3v-induced cross-linking activities. These results support a physiological role for 14,15-EET epoxygenases in regulating epidermal cornification, and they have important implications for epidermal barrier functions in vivo. | Keeney DS, Skinner C, Travers JB, Capdevila JH, Nanney LB, King LE, Waterman MR (1998) Differentiating keratinocytes express a novel cytochrome P450 enzyme, CYP2B19, having arachidonate monooxygenase activity. The Journal of biological chemistry 273, 32071-32079 [PubMed:9822682] [show Abstract] The novel cytochrome P450, CYP2B19, is a specific cellular marker of late differentiation in skin keratinocytes. CYP2B19 was discovered in fetal mouse skin where its onset of expression coincides spatially (upper cell layer) and temporally (day 15.5) with the appearance of loricrin-expressing keratinocytes during the stratification stage of fetal epidermis. CYP2B19 is also present postnatally in the differentiated keratinocytes of the epidermis, sebaceous glands, and hair follicles. CYP2B19 mRNA is tightly coupled to the differentiated (granular cell) keratinocyte phenotype in vivo and in vitro. In primary mouse epidermal keratinocytes, it is specifically up-regulated and correlated temporally with calcium-induced differentiation and expression of the late differentiation genes loricrin and profilaggrin. Recombinant CYP2B19 metabolizes arachidonic acid and generates 14,15- and 11, 12-epoxyeicosatrienoic (EET) acids, and 11-, 12-, and 15-hydroxyeicosatetraenoic (HETE) acids (20, 35, 18, 7, and 7% of total metabolites, respectively). Arachidonic acid metabolism was stereoselective for 11S,12R- and 14S,15R-EET, and 11S-, 12R-, and 15R-HETE. The CYP2B19 metabolites 11,12- and 14,15-EET are endogenous constituents of murine epidermis and are present in similar proportions to that generated by the enzyme in vitro, suggesting that CYP2B19 might be the primary enzymatic source of these EETs in murine epidermis. |
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