1.0 2016-10-03 18:13:23 UTC 2020-05-11 20:42:13 UTC BMDB0011134 BMDB11134 5-HETE 5-Hydroxyeicosatetraenoate (6E,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoic acid 5-Hydroxyeicosatetraenoic acid (6E,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoate (5S,6E,8Z,11Z,14Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoic acid (S)-(e,Z,Z,Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoic acid 5(S)-Hydroxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoic acid 5(S)-Hydroxyeicosatetraenoic acid 5S-HETE (5S,6E,8Z,11Z,14Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoate (S)-(e,Z,Z,Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoate 5(S)-Hydroxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoate 5(S)-Hydroxyeicosatetraenoate 5(S)-HETE 5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoate 5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoic acid 5-Hydroxy-6,8,11,14-eicosatetraenoate 5-Hydroxy-6,8,11,14-eicosatetraenoic acid 5-L-Hydroxy-6,8,11,14-eicosatetraenoate 5-L-Hydroxy-6,8,11,14-eicosatetraenoic acid 5S-Hydroxy-6,8,11,14-eicosatetraenoate 5S-Hydroxy-6,8,11,14-eicosatetraenoic acid 5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,e,Z,Z)-isomer 5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,Z,Z,Z)-(+-)-isomer 5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomer 5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,Z,Z,Z)-isomer 5-Hydroxy-6,8,11,14-eicosatetraenoic acid, R-(e,Z,Z,Z)-isomer (5S,6E,8Z,11Z,14Z)-5-Hydroxy-6,8,11,14-eicosatetraenoic acid 5S-Hydroxy-6,8,11,14-(e,Z,Z,Z)-eicosatetraenoic acid FA(20:4(5-OH,6E,8Z,11Z,14Z)) FA(20:4(5S-OH,6E,8Z,11Z,14Z)) 5-HETE C20H32O3 320.4663 320.23514489 (5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid 5-hydroxyeicosatetraenoic acid 70608-72-9 CCCCC\C=C/C\C=C/C\C=C/C=C/[C@@H](O)CCCC(O)=O InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1 KGIJOOYOSFUGPC-JGKLHWIESA-N belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds. Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Hydroxyeicosatetraenoic acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroxy fatty acids Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Secondary alcohols Unsaturated fatty acids Alcohol Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Hydroxy fatty acid Hydroxyeicosatetraenoic acid Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Unsaturated fatty acid Aliphatic acyclic compounds HETE Hydroxy/hydroperoxyeicosatetraenoic acids Hydroxy/hydroperoxyeicosatetraenoic acids Solid logp 5.88 ALOGPS logs -5.32 ALOGPS logp 5.36 ChemAxon pka_strongest_acidic 4.58 ChemAxon pka_strongest_basic -1.5 ChemAxon iupac (5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid ChemAxon average_mass 320.4663 ChemAxon mono_mass 320.23514489 ChemAxon smiles CCCCC\C=C/C\C=C/C\C=C/C=C/[C@@H](O)CCCC(O)=O ChemAxon formula C20H32O3 ChemAxon inchi InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1 ChemAxon inchikey KGIJOOYOSFUGPC-JGKLHWIESA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 101.47 ChemAxon polarizability 38.13 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Arachidonic Acid Metabolism SMP0087220 Specdb::NmrOneD 270738 Specdb::NmrOneD 270739 Specdb::NmrOneD 270740 Specdb::NmrOneD 270741 Specdb::NmrOneD 270742 Specdb::NmrOneD 270743 Specdb::NmrOneD 270744 Specdb::NmrOneD 270745 Specdb::NmrOneD 270746 Specdb::NmrOneD 270747 Specdb::NmrOneD 270748 Specdb::NmrOneD 270749 Specdb::NmrOneD 270750 Specdb::NmrOneD 270751 Specdb::NmrOneD 270752 Specdb::NmrOneD 270753 Specdb::NmrOneD 270754 Specdb::NmrOneD 270755 Specdb::NmrOneD 270756 Specdb::NmrOneD 270757 Specdb::MsMs 94239 Specdb::MsMs 94240 Specdb::MsMs 94241 Specdb::MsMs 158256 Specdb::MsMs 158257 Specdb::MsMs 158258 Specdb::MsMs 435467 Specdb::MsMs 435468 Specdb::MsMs 435469 Specdb::MsMs 435470 Specdb::MsMs 435471 Specdb::MsMs 435472 Specdb::MsMs 435473 Specdb::MsMs 435474 Specdb::MsMs 435475 Specdb::MsMs 2792864 Specdb::MsMs 2792865 Specdb::MsMs 2792866 Specdb::MsMs 2916458 Specdb::MsMs 2916459 Specdb::MsMs 2916460 Specdb::CMs 10783 Specdb::CMs 39556 Specdb::CMs 156865 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 5280733 4444314 28209 C04805 FDB001434 C00000423 5-Hydroxyeicosatetraenoic_acid 6554 Nicolaou, K. C.; Ladduwahetty, T.; Taffer, I. M.; Zipkin, R. E. A general strategy for the synthesis of monohydroxyeicosatetraenoic acids. Total synthesis of 5(S)-hydroxy-6(E),8,11,14(Z)-eicosatetraenoic acid (5-HETE) and 12(S)-hydroxy-5,8,14(Z),10(E)-eicosatetraenoic acid (12-HETE). Synthesis (1986), (4), 344-7.