Record Information |
---|
Version | 2.0 |
---|
Creation Date | 2012-05-31 13:47:16 -0600 |
---|
Update Date | 2015-06-03 15:53:50 -0600 |
---|
Secondary Accession Numbers | |
---|
Identification |
---|
Name: | 5(S)-Hydroperoxyeicosatetraenoic acid |
---|
Description | 5(S)-Hydroperoxyeicosatetraenoic acid is a lipid hydroperoxide precursor of leukotrienes. The first step of biosynthesis of leukotrienes is conversion of arachidonic acid into 5(S)-hydroperoxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid [5(S)-HpETE] by 5- lipoxygenases (5-LOX). Lipid hydroperoxides undergo homolytic decomposition into bifunctional electrophiles, which react with DNA bases to form DNA adducts. 5-LOX, the enzyme responsible for the formation of 5(S)-HpETE in vivo, is expressed primarily in leukocytes, including monocytes and macrophages. (PMID: 15777099) |
---|
Structure | |
---|
Synonyms: | - (6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
- (6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoic acid
- 5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate
- 5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid
- 5(S)-Hydroperoxyeicosatetraenoate
- 5-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate
- 5-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid
|
---|
Chemical Formula: | C20H32O4 |
---|
Weight: | Average: 336.4657 Monoisotopic: 336.230059512 |
---|
InChI Key: | JNUUNUQHXIOFDA-JGKLHWIESA-N |
---|
InChI: | InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1 |
---|
CAS number: | 71774-08-8 |
---|
IUPAC Name: | (5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid |
---|
Traditional IUPAC Name: | 5-HpETE |
---|
SMILES: | CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](CCCC(O)=O)OO |
---|
Chemical Taxonomy |
---|
Description | belongs to the class of organic compounds known as hydroperoxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and four CC double bonds. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Fatty Acyls |
---|
Sub Class | Eicosanoids |
---|
Direct Parent | Hydroperoxyeicosatetraenoic acids |
---|
Alternative Parents | |
---|
Substituents | - Hydroperoxyeicosatetraenoic acid
- Long-chain fatty acid
- Hydroperoxy fatty acid
- Fatty acid
- Unsaturated fatty acid
- Allylic hydroperoxide
- Hydroperoxide
- Carboxylic acid derivative
- Alkyl hydroperoxide
- Carboxylic acid
- Peroxol
- Monocarboxylic acid or derivatives
- Carbonyl group
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Physical Properties |
---|
State: | Solid |
---|
Charge: | -1 |
---|
Melting point: | Not Available |
---|
Experimental Properties: | |
---|
Predicted Properties | |
---|
Biological Properties |
---|
Cellular Locations: | Membrane |
---|
Reactions: | |
---|
SMPDB Pathways: | |
---|
KEGG Pathways: | - Arachidonic acid metabolism ec00590
|
---|
EcoCyc Pathways: | Not Available |
---|
Concentrations |
---|
| Not Available |
---|
Spectra |
---|
Spectra: | Spectrum Type | Description | Splash Key | |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ufv-7293000000-1f097659cf0dcff9bef9 | View in MoNA |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00bl-9145000000-04747e5703a025ef8f4f | View in MoNA |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0119000000-5146d59d15dbfb1648ac | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000l-5895000000-636edd63bf1c315085fb | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f96-7970000000-59e419db47612aac9e21 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0029000000-27b34dc78df443e7b2e7 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0fri-4189000000-4d5ecf358e00eaff1450 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9160000000-7865a2863663a5eb39ab | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0009000000-4313d8567d98daeec5be | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0k9i-2069000000-56e8fbe6c944c9901664 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9330000000-a6266812ce67a6e4e4f6 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-1369000000-fdc7ed645955c857b4f6 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00li-6924000000-769a1698f7fc3038abd9 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05nf-9300000000-13e0c97d67ef1cdf5fc0 | View in MoNA |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
|
---|
References |
---|
References: | - Jian, W., Lee, S. H., Arora, J. S., Silva Elipe, M. V., Blair, I. A. (2005). "Unexpected formation of etheno-2'-deoxyguanosine adducts from 5(S)-hydroperoxyeicosatetraenoic acid: evidence for a bis-hydroperoxide intermediate." Chem Res Toxicol 18:599-610. Pubmed: 15777099
- Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- Puustinen T, Scheffer MM, Samuelsson B: Endogenously generated 5-hydroperoxyeicosatetraenoic acid is the preferred substrate for human leukocyte leukotriene A4 synthase activity. FEBS Lett. 1987 Jun 15;217(2):265-8. Pubmed: 3036580
|
---|
Synthesis Reference: | Dussault, Patrick; Lee, In Quen. A Chemoenzymic Approach to Hydroperoxyeicosatetraenoic Acids. Total Synthesis of 5(S)-HPETE. Journal of Organic Chemistry (1995), 60(1), 218-26. |
---|
Material Safety Data Sheet (MSDS) | Not Available |
---|
Links |
---|
External Links: | |
---|