| Record Information |
| Version |
3.5 |
| Creation Date |
2008-10-29 06:41:32 -0600 |
| Update Date |
2013-02-08 17:25:44 -0700 |
| HMDB ID |
HMDB11134 |
| Secondary Accession Numbers |
|
| Metabolite Identification |
| Common Name |
5-HETE |
| Description |
5-hydroxyeicosatetraenoic acid (5-HETE) is an endogenous eicosanoid. 5-HETE is an intermediate in arachidonic acid metabolism. It is converted from 5(S)-HPETE via the enzyme glutathione peroxidase (EC 1.11.1.9)and then converted to 5-OxoETE. It is also involved in the pathway of leukotriene synthesis. In addition, it is a modulator of tubuloglomerular feedback. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 5(S)-HETE
- 5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoate
- 5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoic acid
- 5(S)-Hydroxyeicosatetraenoate
- 5(S)-Hydroxyeicosatetraenoic acid
- 5-HETE
- 5-Hydroxy-6,8,11,14-eicosatetraenoate
- 5-Hydroxy-6,8,11,14-eicosatetraenoic acid
- 5-Hydroxyeicosatetraenoate
- 5-Hydroxyeicosatetraenoic acid
- 5-L-Hydroxy-6,8,11,14-eicosatetraenoate
- 5-L-Hydroxy-6,8,11,14-eicosatetraenoic acid
- 5S-Hydroxy-6,8,11,14-eicosatetraenoate
- 5S-Hydroxy-6,8,11,14-eicosatetraenoic acid
|
| Chemical Formula |
C20H32O3 |
| Average Molecular Weight |
320.4663 |
| Monoisotopic Molecular Weight |
320.23514489 |
| IUPAC Name |
(5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid |
| Traditional IUPAC Name |
5(S)-hete |
| CAS Registry Number |
70608-72-9 |
| SMILES |
CCCCC\C=C/C\C=C/C\C=C/C=C/[C@@H](O)CCCC(O)=O |
| InChI Identifier |
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1 |
| InChI Key |
KGIJOOYOSFUGPC-JGKLHWIESA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Eicosanoids |
| Sub Class |
Hydroxyeicosatetraenoic Acids |
| Other Descriptors |
- Aliphatic Acyclic Compounds
- HETE(ChEBI)
- Hydroxy Fatty Acids
- Hydroxy/hydroperoxyeicosatetraenoic acids(KEGG)
- Hydroxy/hydroperoxyeicosatetraenoic acids(Lipidmaps)
- Organic Compounds
- Straight Chain Fatty Acids
- Unsaturated Fatty Acids
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| Substituents |
- Acyclic Alkene
- Allyl Alcohol
- Carboxylic Acid
- Secondary Alcohol
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| Direct Parent |
Hydroxyeicosatetraenoic Acids |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
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| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
- Extracellular
- Membrane (predicted from logP)
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| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
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| Predicted Properties |
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| Spectra |
|
Not Available
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| Biological Properties |
| Cellular Locations |
- Extracellular
- Membrane (predicted from logP)
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| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
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| Tissue Location |
Not Available
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| Pathways |
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| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
0.0119 +/- 0.0014 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
0.001598 +/- 0.000958 uM |
Adult (>18 years old) |
Both |
Normal |
Oxygenated lipids were quantified by Theresa L....
|
| Blood |
Detected and Quantified |
|
0.159 +/- 0.037 uM |
Adult (>18 years old) |
Both |
Normal |
After in vitro stimulation of whole blood at...
|
| Blood |
Detected and Quantified |
|
0.25 +/- 0.09 uM |
Adult (>18 years old) |
Both |
Normal |
Quantified by GC/SIM in serum (n=10)
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| Blood |
Detected and Quantified |
|
0.07 +/- 0.02 uM |
Adult (>18 years old) |
Both |
Normal |
Quantified by GC/SIM in plasma (n=10)
|
| Blood |
Detected and Quantified |
|
3.51 +/- 0.57 uM |
Adult (>18 years old) |
Both |
Normal |
Serum stimulated with 2 mM arachidonic acid and...
|
| Blood |
Detected and Quantified |
|
0.901 +/- 0.029 uM |
Adult (>18 years old) |
Not Specified |
Normal |
HM Replicate Plasma (n=3)
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| Blood |
Detected and Quantified |
|
1.02 +/- 0.79 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Pennington Plasma (n=70)
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| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.00039 +/- 0.00016 uM |
Adult (>18 years old) |
Both |
Normal |
Measured via MS/MS techniques from 4 pooled CSF...
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| Abnormal Concentrations |
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| Blood |
Detected and Quantified |
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0.787 +/- 0.056 uM |
Adult (>18 years old) |
Both |
Rhinitis patients |
After in vitro stimulation of whole blood at...
|
| Blood |
Detected and Quantified |
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1.605 +/- 0.209 uM |
Adult (>18 years old) |
Both |
Asthma |
Untreated asthmatic patients
After in vitro...
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| Blood |
Detected and Quantified |
|
0.600 +/- 0.097 uM |
Adult (>18 years old) |
Both |
Rheumatoid arthritis |
After in vitro stimulation of whole blood at...
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| Associated Disorders and Diseases |
| Disease References |
| Rhinitis |
- Chavis C, Fraissinet L, Chanez P, Thomas E, Bousquet J: A method for the measurement of plasma hydroxyeicosatetraenoic acid levels. Anal Biochem. 1999 Jun 15;271(1):105-8.
Pubmed: 10361015
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| Asthma |
- Chavis C, Fraissinet L, Chanez P, Thomas E, Bousquet J: A method for the measurement of plasma hydroxyeicosatetraenoic acid levels. Anal Biochem. 1999 Jun 15;271(1):105-8.
Pubmed: 10361015
|
| Rheumatoid arthritis |
- Chavis C, Fraissinet L, Chanez P, Thomas E, Bousquet J: A method for the measurement of plasma hydroxyeicosatetraenoic acid levels. Anal Biochem. 1999 Jun 15;271(1):105-8.
Pubmed: 10361015
|
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| Associated OMIM IDs |
|
| External Links |
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB001434 |
| KNApSAcK ID |
C00000423  |
| Chemspider ID |
4444314  |
| KEGG Compound ID |
C04805  |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
5-Hydroxyeicosatetraenoic acid  |
| NuGOwiki Link |
HMDB11134  |
| Metagene Link |
HMDB11134  |
| METLIN ID |
6554  |
| PubChem Compound |
5280733  |
| PDB ID |
Not Available |
| ChEBI ID |
28209  |
| References |
| Synthesis Reference |
Nicolaou, K. C.; Ladduwahetty, T.; Taffer, I. M.; Zipkin, R. E. A general strategy for the synthesis of monohydroxyeicosatetraenoic acids. Total synthesis of 5(S)-hydroxy-6(E),8,11,14(Z)-eicosatetraenoic acid (5-HETE) and 12(S)-hydroxy-5,8,14(Z),10(E)-eicosatetraenoic acid (12-HETE). Synthesis (1986), (4), 344-7. |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
- Kragballe K, Desjarlais L, Duell EA, Voorhees JJ: In vitro synthesis of 12-hydroxy-eicosatetraenoic acid is increased in uninvolved psoriatic epidermis. J Invest Dermatol. 1986 Jul;87(1):47-52.
Pubmed: 3088130
- Kanaji K, Okuma M, Sugiyama T, Sensaki S, Ushikubi F, Uchino H: Requirement of free arachidonic acid for leukotriene B4 biosynthesis by 12-hydroperoxyeicosatetraenoic acid-stimulated neutrophils. Biochem Biophys Res Commun. 1986 Jul 31;138(2):589-95.
Pubmed: 3017333
- Pawlowski NA, Kaplan G, Hamill AL, Cohn ZA, Scott WA: Arachidonic acid metabolism by human monocytes. Studies with platelet-depleted cultures. J Exp Med. 1983 Aug 1;158(2):393-412.
Pubmed: 6411852
- Sasaki T, Asano T, Takakura K, Sano K, Nakamura T, Suzuki N, Imabayashi S, Ishikawa Y: [Cerebral vasospasm and lipid peroxidation--lipid peroxides in the cerebrospinal fluid after subarachnoid hemorrhage] No To Shinkei. 1982 Dec;34(12):1191-6.
Pubmed: 7159548
- Hoffman T, Lizzio EF, Suissa J, Rotrosen D, Sullivan JA, Mandell GL, Bonvini E: Dual stimulation of phospholipase activity in human monocytes. Role of calcium-dependent and calcium-independent pathways in arachidonic acid release and eicosanoid formation. J Immunol. 1988 Jun 1;140(11):3912-8.
Pubmed: 2836505
- Powell WS, Rokach J: Biochemistry, biology and chemistry of the 5-lipoxygenase product 5-oxo-ETE. Prog Lipid Res. 2005 Mar-May;44(2-3):154-83. Epub 2005 Apr 20.
Pubmed: 15893379
- Sud'ina GF, Kobel'kov GM, Barskii OA, Varfolomeev SD: [A kinetic scheme of human neutrophil 5-lipoxygenase activity] Biokhimiia. 1990 Oct;55(10):1795-811.
Pubmed: 1964097
- Bigby TD, Meslier N: Transcellular lipoxygenase metabolism between monocytes and platelets. J Immunol. 1989 Sep 15;143(6):1948-54.
Pubmed: 2550547
- Brinkman HJ, van Buul-Wortelboer MF, van Mourik JA: Selective conversion and esterification of monohydroxyeicosatetraenoic acids by human vascular smooth muscle cells: relevance to smooth muscle cell proliferation. Exp Cell Res. 1991 Jan;192(1):87-92.
Pubmed: 1984423
- Soter NA: The skin in mastocytosis. J Invest Dermatol. 1991 Mar;96(3):32S-38S; discussion 38S-39S.
Pubmed: 1672136
- Chabannes B, Poubelle PE, Moliere P, De Medicis R, Lussier A, Lagarde M: Platelets abrogate leukotriene B(4) generation by human blood neutrophils stimulated with monosodium urate monohydrate or f-Met-Leu-Phe in vitro. Lab Invest. 2003 Apr;83(4):491-9.
Pubmed: 12695552
- Hosni M, Meskini N, Prigent AF, Anker G, Joulain C, el Habib R, Lagarde M: Diethyldithiocarbamate (ditiocarb sodium) effect on arachidonic acid metabolism in human mononuclear cells. Glutathione peroxidase-like activity. Biochem Pharmacol. 1992 Mar 17;43(6):1319-29.
Pubmed: 1314059
- Maderna P, Colli S, Caruso D, Eligini S, Toia A, Galli G, Tremoli E: Quantitative changes of hydroxyacid formation during platelet-neutrophil interaction. J Lab Clin Med. 1993 Mar;121(3):406-14.
Pubmed: 8383163
- Goetzl EJ: Vitamin E modulates the lipoxygenation of arachidonic acid in leukocytes. Nature. 1980 Nov 13;288(5787):183-5.
Pubmed: 6253824
- Marcus AJ, Safier LB, Broekman MJ, Ullman HL, Islam N, Sorrell TC, Serhan CN, Weissmann G, Oglesby TD, Gorman RR: Production of metabolic products of arachidonic acid during cell-cell interactions. J Allergy Clin Immunol. 1984 Sep;74(3 Pt 2):338-42.
Pubmed: 6088611
- Dahinden CA, Clancy RM, Gross M, Chiller JM, Hugli TE: Leukotriene C4 production by murine mast cells: evidence of a role for extracellular leukotriene A4. Proc Natl Acad Sci U S A. 1985 Oct;82(19):6632-6.
Pubmed: 2995976
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