(5Z,8Z,11Z,14Z)-16-Hydroxy-5,8,11,14-eicosatetraenoic acid
16-HETE · (±)16-HETE · JEKNPVYFNMZRJG-UFINWASNSA-N · (±)16-HETE, CAS 128914-46-5 · 16-hydroxy-5(Z),8(Z),11(Z),14(Z)-ETA · 16-hydroxy-5(Z),8(Z),11(Z),14(Z)-eicosatetraenoic acid · 5,8,11,14-Eicosatetraenoic acid, 16-hydroxy-, (5Z,8Z,11Z,14Z)-
Identifikatoren & physikalische Daten
| CAS No. | 128914-46-5 |
|---|---|
| Summenformel | C20H32O3 |
| Durchschnittliche Molmasse | 320,5 g/mol |
| Monoisotopische Masse | 320,23514488 g/mol |
| SMILES | CCCCC(O)/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O |
| InChIKey | JEKNPVYFNMZRJG-UFINWASNSA-N |
| PubChem CID | 6442739 |
| ChEBI | CHEBI:63994 |
| DTXSID | DTXSID501192263 |
Chemische & physikalische Eigenschaften
| XLogP | 4,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 57,5 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 14 |
| Schwere Atome | 23 |
| Formalladung | 0 |
| Komplexität | 392 |
| Lipide | Fatty Acyls [FA] -> Eicosanoids [FA03] -> Hydroxy/hydroperoxyeicosatetraenoic acids [FA0306] |
| Collision Cross Section | 183.4 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Calculation: Single FieldDataset: Oxylipins] |
| Siedepunkt | 477.276±45.00 °C(Press: 760.00 Torr)(predicted) |
| Dichte | 0.984±0.06 g/cm3(Temp: 25 °CPress: 760 Torr)(predicted) |
| Lagerbedingungen | Store at -20°C |
| Löslichkeit | 0.1 M Na2CO3: 2 mg/mlDMF: MiscibleDMSO: MiscibleEthanol: MisciblePBS (pH 7.2): 0.8 mg/ml |
| pKa (Säurekonstante) | 4.752±0.10(predicted) |
Anwendungen & Verwendung
Beschreibung
Electrolyte and fluid transport in the kidney are regulated in part by arachidonic acid and its metabolites. (±)16-HETE is the racemic version of a minor CYP450 metabolite of arachidonic acid released by the kidney upon angiotensin II stimulation. The biological activity of 16-HETE is stereospecific. 16(R)-HETE dose-dependently stimulates vasodilation of the rabbit kidney, however 16(S)-HETE does not affect perfusion pressure. At a concentration of 2 μM the (S)-enantiomer of 16-HETE inhibits proximal tubule ATPase activity by as much as 60%, whereas the (R)-isomer has negligible effects on ATPase activity.