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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-10-29 12:41:32 UTC
Update Date2017-12-07 02:29:12 UTC
HMDB IDHMDB0011134
Secondary Accession Numbers
  • HMDB02218
  • HMDB11134
Metabolite Identification
Common Name5-HETE
Description5-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
Thumb
Synonyms
ValueSource
(5S,6E,8Z,11Z,14Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoic acidChEBI
(6E,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoic acidChEBI
(S)-(e,Z,Z,Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoic acidChEBI
5(S)-Hydroxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoic acidChEBI
5(S)-Hydroxyeicosatetraenoic acidChEBI
5-HydroxyeicosatetraenoateChEBI
5S-HETEChEBI
(5S,6E,8Z,11Z,14Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoateGenerator
(6E,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoateGenerator
(S)-(e,Z,Z,Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoateGenerator
5(S)-Hydroxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoateGenerator
5(S)-HydroxyeicosatetraenoateGenerator
5-Hydroxyeicosatetraenoic acidGenerator
5(S)-HETEHMDB
5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoateHMDB
5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoic acidHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoateHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acidHMDB
5-L-Hydroxy-6,8,11,14-eicosatetraenoateHMDB
5-L-Hydroxy-6,8,11,14-eicosatetraenoic acidHMDB
5S-Hydroxy-6,8,11,14-eicosatetraenoateHMDB
5S-Hydroxy-6,8,11,14-eicosatetraenoic acidHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,e,Z,Z)-isomerMeSH
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,Z,Z,Z)-(+-)-isomerMeSH
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomerMeSH
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,Z,Z,Z)-isomerMeSH
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, R-(e,Z,Z,Z)-isomerMeSH
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid
Traditional Name5-hydroxyeicosatetraenoic acid
CAS Registry Number70608-72-9
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 KeyKGIJOOYOSFUGPC-JGKLHWIESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentHydroxyeicosatetraenoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0015 g/LALOGPS
logP5.88ALOGPS
logP5.36ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.58ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.47 m³·mol⁻¹ChemAxon
Polarizability38.13 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-7293000000-4000067abc9684c2e653View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-056s-9117300000-40397121b4b937950f9dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0ldi-0079000000-52dac491931feca303a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0pvi-0196000000-b7a43328bfcf1b860873View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-1000-0293000000-6e834102b17e5bbec6fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-1000-0390000000-61ebc99aa5f8333b07d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-03di-1930000000-b877c0d03861ddd2728dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0aor-9620000000-8cfab24155dae08cc2caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014i-0910000000-90f71c96ff730ececc7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-08fr-4900000000-e0a2e06154c966bbfcc8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0a4i-9000000000-a54cdd357529bdc9f5e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0149000000-eb17d14c7966577fd391View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-4693000000-a850cad35b2bb6dbc176View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9880000000-8e15d5e341c49c793973View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-eb6fa786699adba566beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ldi-2179000000-3bed63121486cd2b2630View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9150000000-29ad65a68f2ec87b590fView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Acetaminophen Action PathwayPw000687Pw000687 greyscalePw000687 simpleNot Available
Acetylsalicylic Acid PathwayPw000128Pw000128 greyscalePw000128 simpleNot Available
Antipyrine Action PathwayPw000669Pw000669 greyscalePw000669 simpleNot Available
Antrafenine Action PathwayPw000670Pw000670 greyscalePw000670 simpleNot Available
Arachidonic Acid MetabolismPw000044Pw000044 greyscalePw000044 simpleMap00590
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0119 +/- 0.0014 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.001598 +/- 0.000958 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.159 +/- 0.037 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.25 +/- 0.09 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.07 +/- 0.02 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified3.51 +/- 0.57 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000901 +/- 0.000029 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00102 +/- 0.00079 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00039 +/- 0.00016 uMAdult (>18 years old)Both
Normal
    • John W. Newman, U...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.787 +/- 0.056 uMAdult (>18 years old)Both
Rhinitis
details
BloodDetected and Quantified1.605 +/- 0.209 uMAdult (>18 years old)Both
Asthma
details
BloodDetected and Quantified0.600 +/- 0.097 uMAdult (>18 years old)Both
Rheumatoid arthritis
details
Associated Disorders and Diseases
Disease References
Asthma
  1. 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
  1. 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 ]
Rhinitis
  1. 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 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001434
KNApSAcK IDC00000423
Chemspider ID4444314
KEGG Compound IDC04805
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link5-Hydroxyeicosatetraenoic acid
METLIN ID6554
PubChem Compound5280733
PDB IDNot Available
ChEBI ID28209
References
Synthesis ReferenceNicolaou, 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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. Bigby TD, Meslier N: Transcellular lipoxygenase metabolism between monocytes and platelets. J Immunol. 1989 Sep 15;143(6):1948-54. [PubMed:2550547 ]
  10. 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 ]
  11. Soter NA: The skin in mastocytosis. J Invest Dermatol. 1991 Mar;96(3):32S-38S; discussion 38S-39S. [PubMed:1672136 ]
  12. 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 ]
  13. 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 ]
  14. Goetzl EJ: Vitamin E modulates the lipoxygenation of arachidonic acid in leukocytes. Nature. 1980 Nov 13;288(5787):183-5. [PubMed:6253824 ]
  15. 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 ]
  16. 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 ]
  17. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  18. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  19. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  20. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  21. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in glutathione peroxidase activity
Specific function:
It protects esophageal epithelia from hydrogen peroxide-induced oxidative stress. It suppresses acidic bile acid-induced reactive oxigen species (ROS) and protects against oxidative DNA damage and double-strand breaks.
Gene Name:
GPX7
Uniprot ID:
Q96SL4
Molecular weight:
20995.88
Reactions
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Waterdetails
General function:
Involved in glutathione peroxidase activity
Specific function:
Protects cells and enzymes from oxidative damage, by catalyzing the reduction of hydrogen peroxide, lipid peroxides and organic hydroperoxide, by glutathione. May constitute a glutathione peroxidase-like protective system against peroxide damage in sperm membrane lipids.
Gene Name:
GPX5
Uniprot ID:
O75715
Molecular weight:
25202.14
Reactions
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Waterdetails
General function:
Involved in glutathione peroxidase activity
Specific function:
Not Available
Gene Name:
GPX6
Uniprot ID:
P59796
Molecular weight:
24970.46
Reactions
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Waterdetails
General function:
Involved in glutathione peroxidase activity
Specific function:
Protects the hemoglobin in erythrocytes from oxidative breakdown.
Gene Name:
GPX1
Uniprot ID:
P07203
Molecular weight:
22087.94
Reactions
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Waterdetails
General function:
Involved in glutathione peroxidase activity
Specific function:
Protects cells against membrane lipid peroxidation and cell death. Required for normal sperm development and male fertility. Could play a major role in protecting mammals from the toxicity of ingested lipid hydroperoxides. Essential for embryonic development. Protects from radiation and oxidative damage (By similarity).
Gene Name:
GPX4
Uniprot ID:
P36969
Molecular weight:
25046.57
General function:
Involved in glutathione peroxidase activity
Specific function:
Protects cells and enzymes from oxidative damage, by catalyzing the reduction of hydrogen peroxide, lipid peroxides and organic hydroperoxide, by glutathione.
Gene Name:
GPX3
Uniprot ID:
P22352
Molecular weight:
25552.185
Reactions
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Waterdetails
General function:
Involved in glutathione peroxidase activity
Specific function:
Could play a major role in protecting mammals from the toxicity of ingested organic hydroperoxides. Tert-butyl hydroperoxide, cumene hydroperoxide and linoleic acid hydroperoxide but not phosphatidycholine hydroperoxide, can act as acceptors.
Gene Name:
GPX2
Uniprot ID:
P18283
Molecular weight:
21953.835
Reactions
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Waterdetails