12-Hydroxyicosa-5,8,10,14-tetraenoic acid
PubChem CID: 1413
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| Compound Synonyms | 12-hydroxyicosa-5,8,10,14-tetraenoic acid, 12-Hete, DTXSID30869349, DTXCID10817343, ZNHVWPKMFKADKW-UHFFFAOYSA-N, HDA33746, WCA03037, PD093583, DB-056600, DB-226145, NS00127274, 12-hydroxyeicosa-5,8,10,14-tetraenoic acid, 12-Hydroxy-5(Z),8(Z),10(E),14(Z)-eicosatetraenoic acid, 100ug/ml in ethanol |
|---|---|
| Topological Polar Surface Area | 57.5 |
| Hydrogen Bond Donor Count | 2.0 |
| Inchi Key | ZNHVWPKMFKADKW-UHFFFAOYSA-N |
| Rotatable Bond Count | 14.0 |
| State | Solid |
| Synonyms | (E,Z,Z,Z)-12-hydroxy-5,8,10,14-Eicosatetraenoate, (E,Z,Z,Z)-12-hydroxy-5,8,10,14-Eicosatetraenoic acid, 12-Hydroxy-5,8,10,14-eicosatetraenoate, 12-Hydroxy-5,8,10,14-eicosatetraenoic acid, 12-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoate, 12-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid, 12-Hydroxyarachidonic acid, 12-hydroxyeicosatetraenoate, 12-hydroxyeicosatetraenoic acid, 5,8,10,14-Eicosatetraenoic acid, 12-hydroxy-, (E,Z,Z,Z)- |
| Heavy Atom Count | 23.0 |
| Compound Name | 12-Hydroxyicosa-5,8,10,14-tetraenoic acid |
| Description | 12-hydroxyeicosatetraenoic acid (12-HETE) is an eicosanoid, a 5-lipoxygenase metabolite of arachidonic acid. 5-Lipoxygenase (LO)-derived leukotrienes are involved in inflammatory glomerular injury. LO product 12-HETE is associated with pathogenesis of hypertension, and may mediate angiotensin II and TGFbeta induced mesengial cell abnormality in diabetic nephropathy. 12-HETE is markedly elevated in the psoriatic lesions. 12-HETE is a vasoconstrictor eicosanoid that contribute to high blood pressure in (renovascular) hypertension and pregnancy-induced hypertension. A significant percentage of patients suffering from a selective increase in plasma LDL cholesterol (type IIa hyperlipoproteinaemia) exhibits increased platelet reactivity. This includes enhanced platelet responsiveness against a variety of platelet-stimulating agents ex vivo and enhanced arachidonic acid metabolism associated with increased generation of arachidonic acid metabolites such as 12-HETE, and secretion of platelet-storage products. (PMID: 7562532, 12480795, 17361113, 8498970,1333255, 2119633). 12-HETE is a highly selective ligand used to label mu-opioid receptors in both membranes and tissue sections. The 12-s-HETE analog has been reported to augment tumour cell metastatic potential through activation of protein kinase c. 12-HETE can be formed either in the 12-S or 12-R configuration. It has a diversity of biological actions and is generated by a number of tissues including the renal glomerulus and the vasculature. 12-HETE is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid. 12-HETE is a neuromodulator that is synthesized during ischemia. Its neuronal effects include attenuation of calcium influx and glutamate release as well as inhibition of AMPA receptor (AMPA-R) activation. 12-HETE is found in corn. |
| Exact Mass | 320.235 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 320.235 |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 392.0 |
| Hydrogen Bond Acceptor Count | 3.0 |
| Molecular Weight | 320.5 |
| Database Name | fooddb_chem_all;pubchem |
| Covalent Unit Count | 1.0 |
| Defined Atom Stereocenter Count | 0.0 |
| Iupac Name | 12-hydroxyicosa-5,8,10,14-tetraenoic acid |
| Total Atom Stereocenter Count | 1.0 |
| Total Bond Stereocenter Count | 4.0 |
| Inchi | InChI=1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23) |
| Smiles | CCCCCC=CCC(C=CC=CCC=CCCCC(=O)O)O |
| Xlogp | 5.2 |
| Defined Bond Stereocenter Count | 0.0 |
| Molecular Formula | C20H32O3 |
- 1. Outgoing r'ship
FOUND_INto/from Zea Mays (Plant) Rel Props:Source_db:fooddb_chem_all