CAS 128914-46-5 (5Z,8Z,11Z,14Z)-16-Hydroxy-5,8,11,14-eicosatetraenoic acid (HCID 6442739)

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Basic information

CAS: 128914-46-5
Standard SMILES: CCCCC(O)/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
InChIKey: JEKNPVYFNMZRJG-UFINWASNSA-N
Molecular formula: C20H32O3
Average molar mass: 320.5 g/mol
Monoisotopic mass: 320.23514488

Overview

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-).

Names & identifiers

Preferred 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
English name: (±)16-HETE
Molecular formula: C20H32O3
Molecular weight: 320.47

Names & synonyms

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

Show more names

(±)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

Database identifiers

Properties

Computed structural properties

XLogP: 4.8
Topological polar surface area: 57.5 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 14
Heavy atoms: 23
Formal charge: 0
Complexity: 392

Experimental & physicochemical properties

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]

Physicochemical properties

Boiling point: 477.276 · 477.276±45.00 °C(Press: 760.00 Torr)(predicted)
Density: 0.984 · 0.984±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
storage temp.: -20 °C · Store at -20°C
solubility: 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)
Symbol(GHS): 2 · GHS02
Signal word: Danger

Safety & regulation

Safety data

Signal word: Danger
Symbol(GHS): GHS02

Chemistry & industry

Pharmacology

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

Applications · 2 items

DescriptionElectrolyte 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.

Uses16-HETE is arachidonic acid metabolite through subterminal hydroxylation by cytochrome P-450. 16-HETE exhibits vasodilatory and PMN inhibitory effects and serves as biomarker for early stages of non-alcoholic fatty liver disease[1][2][3].