BioPAX pathway converted from "Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE)" in the Reactome database. Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE) This event has been computationally inferred from an event that has been demonstrated in another species.<p>The inference is based on the homology mapping from PANTHER. Briefly, reactions for which all involved PhysicalEntities (in input, output and catalyst) have a mapped orthologue/paralogue (for complexes at least 75% of components must have a mapping) are inferred to the other species. High level events are also inferred for these events to allow for easier navigation.<p><a href='/electronic_inference_compara.html' target = 'NEW'>More details and caveats of the event inference in Reactome.</a> For details on PANTHER see also: <a href='http://www.pantherdb.org/about.jsp' target='NEW'>http://www.pantherdb.org/about.jsp</a> LEFT-TO-RIGHT Arachidonic acid is hydroxylated to 19-HETE by CYP(2) This event has been computationally inferred from an event that has been demonstrated in another species.<p>The inference is based on the homology mapping from PANTHER. Briefly, reactions for which all involved PhysicalEntities (in input, output and catalyst) have a mapped orthologue/paralogue (for complexes at least 75% of components must have a mapping) are inferred to the other species. High level events are also inferred for these events to allow for easier navigation.<p><a href='/electronic_inference_compara.html' target = 'NEW'>More details and caveats of the event inference in Reactome.</a> For details on PANTHER see also: <a href='http://www.pantherdb.org/about.jsp' target='NEW'>http://www.pantherdb.org/about.jsp</a> O2 Oxygen dioxygen Reactome DB_ID: 113534 endoplasmic reticulum lumen GENE ONTOLOGY GO:0005788 dioxygen [ChEBI:15379] dioxygen ChEBI CHEBI:15379 Reactome Database ID Release 82 113534 Database identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser?DB=gk_current&ID=113534 Reactome R-ALL-113534 3 Reactome stable identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser_st_id?ST_ID=R-ALL-113534.3 Reactome http://www.reactome.org COMPOUND C00007 additional information MI MI:0361 TPNH NADPH Reactome DB_ID: 113601 NADPH [ChEBI:16474] NADPH TPNH ChEBI CHEBI:16474 Reactome Database ID Release 82 113601 Database identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser?DB=gk_current&ID=113601 Reactome R-ALL-113601 2 Reactome stable identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser_st_id?ST_ID=R-ALL-113601.2 COMPOUND C00005 H+ hydron Reactome DB_ID: 156540 hydron [ChEBI:15378] hydron ChEBI CHEBI:15378 Reactome Database ID Release 82 156540 Database identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser?DB=gk_current&ID=156540 Reactome R-ALL-156540 3 Reactome stable identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser_st_id?ST_ID=R-ALL-156540.3 COMPOUND C00080 AA arachidonic acid Reactome DB_ID: 140356 arachidonate [ChEBI:32395] arachidonate (20:4n6) (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate (5Z,8Z,11Z,14Z)-eicosatetraenoate ChEBI CHEBI:32395 Reactome Database ID Release 82 140356 Database identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser?DB=gk_current&ID=140356 Reactome R-ALL-140356 4 Reactome stable identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser_st_id?ST_ID=R-ALL-140356.4 H2O water Reactome DB_ID: 113519 water [ChEBI:15377] water ChEBI CHEBI:15377 Reactome Database ID Release 82 113519 Database identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser?DB=gk_current&ID=113519 Reactome R-ALL-113519 3 Reactome stable identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser_st_id?ST_ID=R-ALL-113519.3 COMPOUND C00001 TPN NADP+ NADP NADP(+) Nicotinamide adenine dinucleotide phosphate beta-Nicotinamide adenine dinucleotide phosphate Triphosphopyridine nucleotide Reactome DB_ID: 113564 NADP(+) [ChEBI:18009] NADP(+) ChEBI CHEBI:18009 Reactome Database ID Release 82 113564 Database identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser?DB=gk_current&ID=113564 Reactome R-ALL-113564 3 Reactome stable identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser_st_id?ST_ID=R-ALL-113564.3 COMPOUND C00006 19-HETE Reactome DB_ID: 2142836 19-HETE [ChEBI:63998] 19-HETE ChEBI CHEBI:63998 Reactome Database ID Release 82 2142836 Database identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser?DB=gk_current&ID=2142836 Reactome R-ALL-2142836 2 Reactome stable identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser_st_id?ST_ID=R-ALL-2142836.2 ACTIVATION Converted from EntitySet in Reactome Homologues of CYP2U1 Reactome DB_ID: 10679705 CYP2U1 Q95078 Reactome DB_ID: 10679698 endoplasmic reticulum membrane GENE ONTOLOGY GO:0005789 UniProt:Q95078 Drosophila melanogaster NCBI Taxonomy 7227 UniProt Q95078 1 EQUAL 544 EQUAL Reactome Database ID Release 82 10679698 Database identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser?DB=gk_current&ID=10679698 Reactome R-DME-2142802 1 Reactome stable identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser_st_id?ST_ID=R-DME-2142802.1 CYP2U1 Q9VWR5 Reactome DB_ID: 10679703 UniProt:Q9VWR5 UniProt Q9VWR5 1 EQUAL 544 EQUAL Reactome Database ID Release 82 10679703 Database identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser?DB=gk_current&ID=10679703 Reactome R-DME-2142802-2 1 Reactome stable identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser_st_id?ST_ID=R-DME-2142802-2.1 Reactome Database ID Release 82 10679705 Database identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser?DB=gk_current&ID=10679705 Reactome R-DME-2142802-3 1 Reactome stable identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser_st_id?ST_ID=R-DME-2142802-3.1 GENE ONTOLOGY GO:0004497 gene ontology term for cellular function MI MI:0355 Same Catalyst Activity Reactome Database ID Release 82 10679706 Database identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser?DB=gk_current&ID=10679706 Reactome Database ID Release 82 10704949 Database identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser?DB=gk_current&ID=10704949 Reactome R-DME-2161814 1 Reactome stable identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser_st_id?ST_ID=R-DME-2161814.1 Several cytochrome P450s (CYPs) convert arachidonic acid to 19-hydroxyeicosatetraenoic acid (19-HETE). The CYPs and their references are as follows: CYP2C8 (Bylund et al. 1998); CYP2C9 (Bylund et al. 1998); CYP2C19 (Bylund et al. 1998); CYP4A11 (Gainer et al. 2005); CYP2U1 (Chuang et al. 2004); CYP1A1, CYP1A2, CYP1B1 (Choudhary et al. 2004). 9435160 Pubmed 1998 Cytochromes P450 with bisallylic hydroxylation activity on arachidonic and linoleic acids studied with human recombinant enzymes and with human and rat liver microsomes Bylund, J Kunz, T Valmsen, K Oliw, EH J Pharmacol Exp Ther 284:51-60 15611369 Pubmed 2005 Functional variant of CYP4A11 20-hydroxyeicosatetraenoic acid synthase is associated with essential hypertension Gainer, JV Bellamine, A Dawson, EP Womble, KE Grant, SW Wang, Y Cupples, LA Guo, CY Demissie, S O'Donnell, CJ Brown, NJ Waterman, MR Capdevila, JH Circulation 111:63-9 14660610 Pubmed 2004 CYP2U1, a novel human thymus- and brain-specific cytochrome P450, catalyzes omega- and (omega-1)-hydroxylation of fatty acids Chuang, SS Helvig, C Taimi, M Ramshaw, HA Collop, AH Amad, M White, JA Petkovich, M Jones, G Korczak, B J Biol Chem 279:6305-14 15258110 Pubmed 2004 Metabolism of retinoids and arachidonic acid by human and mouse cytochrome P450 1b1 Choudhary, D Jansson, I Stoilov, I Sarfarazi, M Schenkman, JB Drug Metab Dispos 32:840-7 inferred from electronic annotation EVIDENCE CODE ECO:0000203 LEFT-TO-RIGHT Arachidonic acid is hydroxylated to 20-HETE by CYP(3) This event has been computationally inferred from an event that has been demonstrated in another species.<p>The inference is based on the homology mapping from PANTHER. Briefly, reactions for which all involved PhysicalEntities (in input, output and catalyst) have a mapped orthologue/paralogue (for complexes at least 75% of components must have a mapping) are inferred to the other species. High level events are also inferred for these events to allow for easier navigation.<p><a href='/electronic_inference_compara.html' target = 'NEW'>More details and caveats of the event inference in Reactome.</a> For details on PANTHER see also: <a href='http://www.pantherdb.org/about.jsp' target='NEW'>http://www.pantherdb.org/about.jsp</a> 20-HETE Reactome DB_ID: 2142780 20-HETE [ChEBI:34306] 20-HETE (5Z,8Z,11Z,14Z)-20-Hydroxyicosa-5,8,11,14-tetraenoic acid 20-Hydroxy arachidonic acid 20-Hydroxyeicosatetraenoic acid 20-Hydroxyicosatetraenoic acid ChEBI CHEBI:34306 Reactome Database ID Release 82 2142780 Database identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser?DB=gk_current&ID=2142780 Reactome R-ALL-2142780 2 Reactome stable identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser_st_id?ST_ID=R-ALL-2142780.2 ACTIVATION Reactome Database ID Release 82 10704951 Database identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser?DB=gk_current&ID=10704951 Reactome R-DME-2161940 1 Reactome stable identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser_st_id?ST_ID=R-DME-2161940.1 Several cytochrome P450s (CYPs) convert arachidonic acid to 20-hydroxyeicosatetraenoic acid (20-HETE). The CYPs and their references are as follows: CYP4A11 (Gainer et al. 2005, Powell 1998); CYP4F2 (Powell et al. 1998, Kikuta et al. 2002); CYP2U1 (Chuang et al. 2004); CYP1A1, CYP1A2, CYP1B1 (Choudhary et al. 2004). 12432928 Pubmed 2002 Prostaglandin and leukotriene omega-hydroxylases Kikuta, Y Kusunose, E Kusunose, M Prostaglandins Other Lipid Mediat 68:345-62 9618440 Pubmed 1998 Metabolism of arachidonic acid to 20-hydroxy-5,8,11, 14-eicosatetraenoic acid by P450 enzymes in human liver: involvement of CYP4F2 and CYP4A11 Powell, PK Wolf, I Jin, R Lasker, JM J Pharmacol Exp Ther 285:1327-36 Reactome Database ID Release 82 10742109 Database identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser?DB=gk_current&ID=10742109 Reactome R-DME-2142816 1 Reactome stable identifier. Use this URL to connect to the web page of this instance in Reactome: http://www.reactome.org/cgi-bin/eventbrowser_st_id?ST_ID=R-DME-2142816.1 GENE ONTOLOGY GO:0097267 gene ontology term for cellular process MI MI:0359 Similar to the lipoxygenases, cytochrome P450 (CYP) enzymes catalyse the hydroxylation and epoxygenation of arachidonic acid. However, whereas lipoxygenases use an active non-heme iron to abstract hydrogen directly from arachidonic acid, CYPs contain a heme-iron active site that oxidizes its substrate by a different mechanism. They hydroxylate arachidonic acid between C-5 and C-15 to produce lipoxygenase-like hydroxyeicosatetraenoic acids (HETEs) and add a hydroxyl moiety to the sp3-hybridized omega-carbons to form a unique class of HETEs. The transfer of oxygen to the unstable arachidonic acid intermediate terminates the reaction by forming HETE or epoxy-eicosatrienoic acid (EETs), respectively (Capdevila et al. 2000, Buczynski et al. 2009, Vance & Vance 2008). 10681399 Pubmed 2000 Cytochrome P450 and arachidonic acid bioactivation. Molecular and functional properties of the arachidonate monooxygenase Capdevila, JH Falck, JR Harris, RC J Lipid Res 41:163-81 19244215 Pubmed 2009 Thematic Review Series: Proteomics. An integrated omics analysis of eicosanoid biology Buczynski, MW Dumlao, DS Dennis, EA J Lipid Res 50:1015-38 978-0-444-53219-0 ISBN 2008 The eicosanoids: cyclooxygenase, lipoxygenase, and epoxygenase pathways Smith, William L Murphy, RC Biochemistry of Lipids, Lipoproteins and Membranes, 5th Edition (Book): 331-362