Record Information
Version3.6
Creation Date2008-10-29 12:41:32 UTC
Update Date2013-02-09 00:25:44 UTC
HMDB IDHMDB11134
Secondary Accession Numbers
  • HMDB02218
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
  1. 5(S)-HETE
  2. 5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoate
  3. 5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoic acid
  4. 5(S)-Hydroxyeicosatetraenoate
  5. 5(S)-Hydroxyeicosatetraenoic acid
  6. 5-HETE
  7. 5-Hydroxy-6,8,11,14-eicosatetraenoate
  8. 5-Hydroxy-6,8,11,14-eicosatetraenoic acid
  9. 5-Hydroxyeicosatetraenoate
  10. 5-Hydroxyeicosatetraenoic acid
  11. 5-L-Hydroxy-6,8,11,14-eicosatetraenoate
  12. 5-L-Hydroxy-6,8,11,14-eicosatetraenoic acid
  13. 5S-Hydroxy-6,8,11,14-eicosatetraenoate
  14. 5S-Hydroxy-6,8,11,14-eicosatetraenoic acid
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 IUPAC Name5(S)-hete
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
KingdomOrganic Compounds
Super ClassLipids
ClassEicosanoids
Sub ClassHydroxyeicosatetraenoic 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
Substituents
  • Acyclic Alkene
  • Allyl Alcohol
  • Carboxylic Acid
  • Secondary Alcohol
Direct ParentHydroxyeicosatetraenoic Acids
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
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 area57.53ChemAxon
rotatable bond count14ChemAxon
refractivity101.47ChemAxon
polarizability38.13ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075map00590
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.0119 +/- 0.0014 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified0.001598 +/- 0.000958 uMAdult (>18 years old)BothCommentNormal
BloodDetected and Quantified0.159 +/- 0.037 uMAdult (>18 years old)BothCommentNormal
BloodDetected and Quantified0.25 +/- 0.09 uMAdult (>18 years old)BothCommentNormal
BloodDetected and Quantified0.07 +/- 0.02 uMAdult (>18 years old)BothCommentNormal
BloodDetected and Quantified3.51 +/- 0.57 uMAdult (>18 years old)BothCommentNormal
BloodDetected and Quantified0.901 +/- 0.029 uMAdult (>18 years old)Not SpecifiedCommentNormal
BloodDetected and Quantified1.02 +/- 0.79 uMAdult (>18 years old)Not SpecifiedCommentNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.00039 +/- 0.00016 uMAdult (>18 years old)BothCommentNormal
  • John W. Newm...
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.787 +/- 0.056 uMAdult (>18 years old)BothCommentRhinitis patients
BloodDetected and Quantified1.605 +/- 0.209 uMAdult (>18 years old)BothCommentAsthma
BloodDetected and Quantified0.600 +/- 0.097 uMAdult (>18 years old)BothCommentRheumatoid arthritis
Associated Disorders and Diseases
Disease References
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
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
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
NuGOwiki LinkHMDB11134
Metagene LinkHMDB11134
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

Enzymes

Gene Name:
GPX7
Uniprot ID:
Q96SL4
Reactions
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid unknown Oxidized glutathione + 5-HETE + Waterdetails
Gene Name:
GPX5
Uniprot ID:
O75715
Reactions
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid unknown Oxidized glutathione + 5-HETE + Waterdetails
Gene Name:
GPX6
Uniprot ID:
P59796
Reactions
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid unknown Oxidized glutathione + 5-HETE + Waterdetails
Gene Name:
GPX1
Uniprot ID:
P07203
Reactions
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid unknown Oxidized glutathione + 5-HETE + Waterdetails
Gene Name:
GPX3
Uniprot ID:
P22352
Reactions
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid unknown Oxidized glutathione + 5-HETE + Waterdetails
Gene Name:
GPX2
Uniprot ID:
P18283
Reactions
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid unknown Oxidized glutathione + 5-HETE + Waterdetails