2.0 2012-05-31 13:47:16 -0600 2015-06-03 15:53:50 -0600 ECMDB01193 M2MDB000291 5(S)-Hydroperoxyeicosatetraenoic acid 5(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 acid 5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate 5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid 5(S)-Hydroperoxyeicosatetraenoate 5-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate 5-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid C20H32O4 336.4657 336.230059512 (5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid 5-HpETE 71774-08-8 CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](CCCC(O)=O)OO InChI=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/s1 JNUUNUQHXIOFDA-JGKLHWIESA-N Solid Inner membrane Membrane Outer membrane logp 5.92 ALOGPS logs -5.32 ALOGPS solubility 1.61e-03 g/l ALOGPS logp 5.81 ChemAxon pka_strongest_acidic 4.39 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid ChemAxon average_mass 336.4657 ChemAxon mono_mass 336.230059512 ChemAxon smiles CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](CCCC(O)=O)OO ChemAxon formula C20H32O4 ChemAxon inchi InChI=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/s1 ChemAxon inchikey JNUUNUQHXIOFDA-JGKLHWIESA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 102.82 ChemAxon polarizability 39.53 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Arachidonic acid metabolism Delete 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 A1 PW000759 ec00590 Metabolic Specdb::CMs 15703 Specdb::CMs 37968 Specdb::CMs 166454 Specdb::NmrOneD 288075 Specdb::NmrOneD 288076 Specdb::NmrOneD 288077 Specdb::NmrOneD 288078 Specdb::NmrOneD 288079 Specdb::NmrOneD 288080 Specdb::NmrOneD 288081 Specdb::NmrOneD 288082 Specdb::NmrOneD 288083 Specdb::NmrOneD 288084 Specdb::NmrOneD 288085 Specdb::NmrOneD 288086 Specdb::NmrOneD 288087 Specdb::NmrOneD 288088 Specdb::NmrOneD 288089 Specdb::NmrOneD 288090 Specdb::NmrOneD 288091 Specdb::NmrOneD 288092 Specdb::NmrOneD 288093 Specdb::NmrOneD 288094 Specdb::MsMs 24953 Specdb::MsMs 24954 Specdb::MsMs 24955 Specdb::MsMs 31511 Specdb::MsMs 31512 Specdb::MsMs 31513 Specdb::MsMs 3048323 Specdb::MsMs 3048324 Specdb::MsMs 3048325 Specdb::MsMs 3118295 Specdb::MsMs 3118296 Specdb::MsMs 3118297 HMDB01193 5280778 4444340 C05356 15632 6E8Z11Z14Z-5S-5-HYDROPEROXYCOSA-6 Kanehisa, 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. 22080510 Jian, 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. 15777099 Puustinen 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. 3036580 Dussault, 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 BtuE P06610 BTUE_ECOLI btuE http://ecmdb.ca/proteins/P06610.xml 2 Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid <> Glutathione disulfide + 5-HETE + Water R07034