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Human Metabolome Database Version 3.5

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Showing metabocard for 5-HETE (HMDB11134)

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
  • HMDB02218
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 Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 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
Substituents
  • Acyclic Alkene
  • Allyl Alcohol
  • Carboxylic Acid
  • Secondary Alcohol
Direct Parent Hydroxyeicosatetraenoic Acids
Ontology
Status Detected 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
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
Predicted Properties
Property Value Source
Water Solubility 0.0015 g/L ALOGPS
LogP 5.88 ALOGPS
LogP 5.36 ChemAxon
LogS -5.32 ALOGPS
pKa (strongest acidic) 4.58 ChemAxon
pKa (strongest basic) -1.5 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 57.53 A2 ChemAxon
Rotatable Bond Count 14 ChemAxon
Refractivity 101.47 ChemAxon
Polarizability 38.13 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Arachidonic Acid Metabolism SMP00075 map00590 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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0.0119 +/- 0.0014 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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0.001598 +/- 0.000958 uM Adult (>18 years old) Both Normal Oxygenated lipids were quantified by Theresa L....
Blood Detected and Quantified
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0.159 +/- 0.037 uM Adult (>18 years old) Both Normal After in vitro stimulation of whole blood at...
Blood Detected and Quantified
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0.25 +/- 0.09 uM Adult (>18 years old) Both Normal Quantified by GC/SIM in serum (n=10)
Blood Detected and Quantified
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0.07 +/- 0.02 uM Adult (>18 years old) Both Normal Quantified by GC/SIM in plasma (n=10)
Blood Detected and Quantified
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3.51 +/- 0.57 uM Adult (>18 years old) Both Normal Serum stimulated with 2 mM arachidonic acid and...
Blood Detected and Quantified
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0.901 +/- 0.029 uM Adult (>18 years old) Not Specified Normal HM Replicate Plasma (n=3)
Blood Detected and Quantified
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1.02 +/- 0.79 uM Adult (>18 years old) Not Specified Normal Pennington Plasma (n=70)
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.00039 +/- 0.00016 uM Adult (>18 years old) Both Normal Measured via MS/MS techniques from 4 pooled CSF...
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
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...
Blood Detected and Quantified
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0.600 +/- 0.097 uM Adult (>18 years old) Both Rheumatoid arthritis After in vitro stimulation of whole blood at...
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 Link_out
    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 Link_out
      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 Link_out
        Associated OMIM IDs
        DrugBank ID Not Available
        Phenol Explorer Compound ID Not Available
        Phenol Explorer Metabolite ID Not Available
        FoodDB ID FDB001434
        KNApSAcK ID C00000423 Link_out
        Chemspider ID 4444314 Link_out
        KEGG Compound ID C04805 Link_out
        BioCyc ID Not Available
        BiGG ID Not Available
        Wikipedia Link 5-Hydroxyeicosatetraenoic acid Link_out
        NuGOwiki Link HMDB11134 Link_out
        Metagene Link HMDB11134 Link_out
        METLIN ID 6554 Link_out
        PubChem Compound 5280733 Link_out
        PDB ID Not Available
        ChEBI ID 28209 Link_out
        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
        1. 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 Link_out
        2. 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 Link_out
        3. 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 Link_out
        4. 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 Link_out
        5. 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 Link_out
        6. 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 Link_out
        7. 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 Link_out
        8. Bigby TD, Meslier N: Transcellular lipoxygenase metabolism between monocytes and platelets. J Immunol. 1989 Sep 15;143(6):1948-54. Pubmed: 2550547 Link_out
        9. 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 Link_out
        10. Soter NA: The skin in mastocytosis. J Invest Dermatol. 1991 Mar;96(3):32S-38S; discussion 38S-39S. Pubmed: 1672136 Link_out
        11. 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 Link_out
        12. 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 Link_out
        13. 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 Link_out
        14. Goetzl EJ: Vitamin E modulates the lipoxygenation of arachidonic acid in leukocytes. Nature. 1980 Nov 13;288(5787):183-5. Pubmed: 6253824 Link_out
        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 Link_out
        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 Link_out
        Enzymes
        Name: Glutathione peroxidase 7
        Reactions:
        • 2 glutathione + H2O2 = glutathione disulfide + 2 H2O [RN:R00274]
        Gene Name: GPX7
        Uniprot ID: Q96SL4 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Epididymal secretory glutathione peroxidase
        Reactions:
        • 2 glutathione + H2O2 = glutathione disulfide + 2 H2O [RN:R00274]
        Gene Name: GPX5
        Uniprot ID: O75715 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Glutathione peroxidase 6
        Reactions:
        • 2 glutathione + H2O2 = glutathione disulfide + 2 H2O [RN:R00274]
        Gene Name: GPX6
        Uniprot ID: P59796 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Glutathione peroxidase 1
        Reactions:
        • 2 glutathione + H2O2 = glutathione disulfide + 2 H2O [RN:R00274]
        Gene Name: GPX1
        Uniprot ID: P07203 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Phospholipid hydroperoxide glutathione peroxidase, mitochondrial
        Reactions:
        • 2 glutathione + a lipid hydroperoxide = glutathione disulfide + lipid + 2 H2O [RN:R03167]
        Gene Name: GPX4
        Uniprot ID: P36969 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Glutathione peroxidase 3
        Reactions:
        • 2 glutathione + H2O2 = glutathione disulfide + 2 H2O [RN:R00274]
        Gene Name: GPX3
        Uniprot ID: P22352 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Glutathione peroxidase 2
        Reactions:
        • 2 glutathione + H2O2 = glutathione disulfide + 2 H2O [RN:R00274]
        Gene Name: GPX2
        Uniprot ID: P18283 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA