2.02012-05-31 13:47:16 -06002015-06-03 15:53:50 -0600ECMDB01193M2MDB0002915(S)-Hydroperoxyeicosatetraenoic acid5(S)-Hydroperoxyeicosatetraenoic acid is a lipid hydroperoxide precursor of leukotrienes. The first step of biosynthesis of leukotrienes is conversion of arachidonic acid into 5(S)-hydroperoxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid [5(S)-HpETE] by 5- lipoxygenases (5-LOX). Lipid hydroperoxides undergo homolytic decomposition into bifunctional electrophiles, which react with DNA bases to form DNA adducts. 5-LOX, the enzyme responsible for the formation of 5(S)-HpETE in vivo, is expressed primarily in leukocytes, including monocytes and macrophages. (PMID: 15777099)(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoic acid5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid5(S)-Hydroperoxyeicosatetraenoate5-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate5-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acidC20H32O4336.4657336.230059512(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid5-HpETE71774-08-8CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](CCCC(O)=O)OOInChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1JNUUNUQHXIOFDA-JGKLHWIESA-NSolidInner membraneMembraneOuter membranelogp5.92logs-5.32solubility1.61e-03 g/llogp5.81pka_strongest_acidic4.39pka_strongest_basic-4.2iupac(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acidaverage_mass336.4657mono_mass336.230059512smilesCCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](CCCC(O)=O)OOformulaC20H32O4inchiInChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1inchikeyJNUUNUQHXIOFDA-JGKLHWIESA-Npolar_surface_area66.76refractivity102.82polarizability39.53rotatable_bond_count15acceptor_count4donor_count2physiological_charge-1formal_charge0Arachidonic acid metabolismDelete Pathway
Arachidonate (arachidonic acid) is a polyunsaturated ω-6 fatty acid with a 20-carbon chain and four cis-double bonds. It is produced at high levels by mosses, some plants, and by some marine bacteria.
Mammals cannot synthesize arachidonate de novo, but most mammals are able to synthesize it from simpler unsaturated fatty acids.
In addition to being involved in cellular signaling as a lipid second messenger, arachidonate is also a key inflammatory intermediate and can also act as a vasodilator.
Like other fatty acids, arachidonate is rarely found in its free form. It is usually found either as arachidonoyl-CoA or incorporated into a lipid.
It is produced from phosphatidylcholine through a phospholipase A1PW000759ec00590MetabolicSpecdb::CMs15703Specdb::CMs37968Specdb::CMs166454Specdb::NmrOneD288075Specdb::NmrOneD288076Specdb::NmrOneD288077Specdb::NmrOneD288078Specdb::NmrOneD288079Specdb::NmrOneD288080Specdb::NmrOneD288081Specdb::NmrOneD288082Specdb::NmrOneD288083Specdb::NmrOneD288084Specdb::NmrOneD288085Specdb::NmrOneD288086Specdb::NmrOneD288087Specdb::NmrOneD288088Specdb::NmrOneD288089Specdb::NmrOneD288090Specdb::NmrOneD288091Specdb::NmrOneD288092Specdb::NmrOneD288093Specdb::NmrOneD288094Specdb::MsMs24953Specdb::MsMs24954Specdb::MsMs24955Specdb::MsMs31511Specdb::MsMs31512Specdb::MsMs31513Specdb::MsMs3048323Specdb::MsMs3048324Specdb::MsMs3048325Specdb::MsMs3118295Specdb::MsMs3118296Specdb::MsMs3118297HMDB0119352807784444340C05356156326E8Z11Z14Z-5S-5-HYDROPEROXYCOSA-6Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510Jian, W., Lee, S. H., Arora, J. S., Silva Elipe, M. V., Blair, I. A. (2005). "Unexpected formation of etheno-2'-deoxyguanosine adducts from 5(S)-hydroperoxyeicosatetraenoic acid: evidence for a bis-hydroperoxide intermediate." Chem Res Toxicol 18:599-610.15777099Puustinen T, Scheffer MM, Samuelsson B: Endogenously generated 5-hydroperoxyeicosatetraenoic acid is the preferred substrate for human leukocyte leukotriene A4 synthase activity. FEBS Lett. 1987 Jun 15;217(2):265-8.3036580Dussault, Patrick; Lee, In Quen. A Chemoenzymic Approach to Hydroperoxyeicosatetraenoic Acids. Total Synthesis of 5(S)-HPETE. Journal of Organic Chemistry (1995), 60(1), 218-26.Vitamin B12 transport periplasmic protein BtuEP06610BTUE_ECOLIbtuEhttp://ecmdb.ca/proteins/P06610.xml2 Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid <> Glutathione disulfide + 5-HETE + WaterR07034