(5Z,8Z,11Z,14Z)-16-Hydroxy-5,8,11,14-eicosatetraenoic acid

HCID 6442739CAS 128914-46-5

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Grundinformationen

Standard-SMILES: CCCCC(O)/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
InChIKey: JEKNPVYFNMZRJG-UFINWASNSA-N
Summenformel: C20H32O3
Durchschnittliche Molmasse: 320,5 g/mol
Monoisotopische Masse: 320,23514488

Überblick

16-HETE is a HETE that consists of arachidonic acid bearing an additional hydroxy substituent at position 16. It is a secondary allylic alcohol and a HETE. It is functionally related to an icosa-5,8,11,14-tetraenoic acid. It is a conjugate acid of a 16-HETE(1-).

Namen und Bezeichner

Bevorzugter Name: (5Z,8Z,11Z,14Z)-16-Hydroxy-5,8,11,14-eicosatetraenoic acid
IUPAC: (5Z,8Z,11Z,14Z)-16-hydroxyicosa-5,8,11,14-tetraenoic acid
Englischer Name: (±)16-HETE
Summenformel: C20H32O3
Molmasse: 320.47

Namen und Synonyme

16-HETE128914-46-5(5Z,8Z,11Z,14Z)-16-hydroxyicosa-5,8,11,14-tetraenoic acidCHEBI:63994DTXSID50119226316-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid(all-cis)-16-hydroxy-5,8,11,14-eicosatetraenoic acid(all-cis)-16-hydroxy-5,8,11,14-icosatetraenoic acid(5z,8z,11z,14z)-16-hydroxy-5,8,11,14-eicosatetraenoic acid(5Z,8Z,11Z,14Z)-16-hydroxyeicosa-5,8,11,14-tetraenoic acidRefChem:906229DTXCID401623516

Weitere Namen anzeigen

(±)16-HETEJEKNPVYFNMZRJG-UFINWASNSA-N(±)16-HETE, CAS 128914-46-516-hydroxy-5(Z),8(Z),11(Z),14(Z)-ETA16-hydroxy-5(Z),8(Z),11(Z),14(Z)-eicosatetraenoic acid

(+/-)16-HETE5,8,11,14-Eicosatetraenoic acid, 16-hydroxy-, (5Z,8Z,11Z,14Z)-16-hydroxyarachidonic acidSZ82Y6XRG916(RS)-HETEGTPL6923orb1985157SCHEMBL29559016

Datenbank-Bezeichner

CAS: 128914-46-5
PubChem CID: 6442739
DTXSID: DTXSID501192263
ChEBI: CHEBI:63994
UNII: SZ82Y6XRG9
Nikkaji: J608.787F

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 4,8
Polarare Oberfläche (TPSA): 57,5 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 3
Frei drehbare Bindungen: 14
Schwere Atome: 23
Formalladung: 0
Komplexität: 392

Experimentelle und physikochemische Eigenschaften

LipidsFatty Acyls [FA] -> Eicosanoids [FA03] -> Hydroxy/hydroperoxyeicosatetraenoic acids [FA0306]

Collision Cross Section183.4 Å² [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Calculation: Single Field; Dataset: Oxylipins]

Physikochemische Eigenschaften

Siedepunkt: 477.276 · 477.276±45.00 °C(Press: 760.00 Torr)(predicted)
Dichte: 0.984 · 0.984±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
storage temp.: -20 °C · Store at -20°C
Löslichkeit: 0.1 M · 0.1 M Na2CO3: 2 mg/ml; DMF: Miscible; DMSO: Miscible; Ethanol: Miscible; PBS (pH 7.2): 0.8 mg/ml
pka: 4.752 · 4.752±0.10(predicted)

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites16-HETE is a known human metabolite of arachidonic acid.

Anwendungen · 1 Eintrag

BeschreibungElectrolyte 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.