5-Hydroxyicosatetraenoic acid

5-Hydroxyeicosatetraenoic acid

Names
IUPAC name (5S,6E,8Z,11Z,14Z)-5-Hydroxyicosa-6,8,11,14-tetraenoic acid
Other names 5-HETE, 5(S)-HETE
Identifiers
CAS Number	70608-72-9 N
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:28209 Y
ChemSpider	4444314 Y
ECHA InfoCard	100.161.309
IUPHAR/BPS	3390
PubChem CID	5280733
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 Y Key: KGIJOOYOSFUGPC-JGKLHWIESA-N Y InChI=1/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 Key: KGIJOOYOSFUGPC-JGKLHWIEBQ
SMILES CCCCC/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O)O O=C(O)CCC[C@H](O)/C=C/C=C\C\C=C/C\C=C/CCCCC
Properties
Chemical formula	C20H32O3
Molar mass	320.47 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

5-Hydroxyicosatetraenoic acid (5-HETE, 5(S)-HETE, or 5S-HETE) is an eicosanoid, i.e. a metabolite of arachidonic acid, made by a wide variety of cell types of mammals and other animal species. It along with several closely related metabolites are hormone-like and paracrine signalling agents. In these roles, the 5-HETE family metabolites can amplify or dampen inflammation and allergy responses to disturbances in various animal species. Similar functions in humans, while strongly suggested by animal and tissue studies, requires further translational research.

5-Hydroxyicosatetraenoic acid is more properly termed 5(S)-hydroxyicosatetraenoic acid or 5(S)-HETE) to signify the (S) stereochemical configuration of its 5-hydroxy residue as opposed to its 5(R)-hydroxyicosatetraenoic acid (i.e., 5(R)-HETE) stereoisomer. Since 5(R)-HETE was rarely detected in studies of animals including humans, much of the older and some of the newer literature refers to 5(S)-HETE as 5-HETE. Its IUPAC name, (5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid, defines 5(S)-HETE's structure unambiguously by notating not only its S-hydroxyl chirality but also the cis–trans isomerism geometry for each of its 4 double bonds; E signifies trans and Z signifies cis double bond geometry. The literature commonly uses an alternate but still unambiguous name for 5(S)-HETE viz., 5(S)-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid.

The Nobel laureate, Bengt I. Samuelsson, and colleagues first described 5(S)-HETE in 1976 as a metabolite of arachidonic acid made by rabbit neutrophils. Biological activity was linked to it several years later when it was found to stimulate human neutrophil rises in cytosolic calcium, chemotaxis, and increases in their cell surface adhesiveness as indicated by their aggregation to each other. Since a previously discovered arachidonic acid metabolite made by neutrophils, leukotriene B4 (LTB₄), also stimulates human neutrophil calcium rises, chemotaxis, and auto-aggregation and is structurally similar to 5(S)-HETE in being a 5-(S)-hydroxy-eicosateraenoate, it was assumed that 5-(S)-HETE stimulated cells through the same cell surface receptors as those used by (LTB₄) viz., the leukotriene B4 receptors. However, further studies in neutrophils indicated that 5-(S)-HETE acted through a receptor distinct from that used by LTB₄ as well as various other neutrophil stimuli, the oxoeicosanoid receptor 1 (OXER1).