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Record Information
Version4.0
Creation Date2006-08-13 06:28:20 UTC
Update Date2017-10-23 19:04:09 UTC
HMDB IDHMDB0003876
Secondary Accession Numbers
  • HMDB02110
  • HMDB03876
Metabolite Identification
Common Name15(S)-HETE
Description15(S)-HETE is a hydroxyeicosatetraenoic acid. Hydroxyeicosatetraenoic acids (HETEs) are formed by the 5-, 12- and 15-lipoxygenase (LO) pathways. 5- and 12-LO products are mainly proinflammatory in the skin whereas the main 15-LO product 15-HETE has antiinflammatory capacities. In vitro 15-HETE has been shown to inhibit LTB4 formation, 12-HETE formation and specifically inhibits the neutrophil chemotactic effect of LTB4. The inhibition of LTB4 formation is probably due to modulation of the 5-LO because no changes in PGE2 formation have been determined. In vivo, 15-HETE inhibits LTB4-induced erythema and edema, and reduces LTB4 in the synovial fluid of carragheenan-induced experimental arthritis in dogs. 15-HETE has also some immunomodulatory effects. It inhibits the mixed lymphocyte reaction, induces generation of murine cytotoxic suppressor T cells, and it decreases interferon production by murine lymphoma cells. Furthermore, IL-4 and IL-13 have recently been shown to be potent activators of the 15-LO in mononuclear cells. (PMID: 11104340 ).
Structure
Thumb
Synonyms
ValueSource
(15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoateChEBI
(15S)-15-Hydroxy-5,8,11-cis-13-trans-icosatetraenoateChEBI
(15S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acidChEBI
(15S)-Hydroxyeicosa-(5Z,8Z,11Z,13E)-tetraenoic acidChEBI
(5Z,8Z,11Z,13E)-(15S)-15-Hydroxyicosa-5,8,11,13-tetraenoic acidChEBI
(5Z,8Z,11Z,13E,15S)-15-Hydroxy-5,8,11,13-eicosatetraenoic acidChEBI
(5Z,8Z,11Z,13E,15S)-15-Hydroxyeicosa-5,8,11,13-tetraenoic acidChEBI
15(S)-Hydroxyeicosatetraenoic acidChEBI
15S-HETEChEBI
IcomucretChEBI
(15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoic acidGenerator
(15S)-15-Hydroxy-5,8,11-cis-13-trans-icosatetraenoic acidGenerator
(15S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateGenerator
(15S)-Hydroxyeicosa-(5Z,8Z,11Z,13E)-tetraenoateGenerator
(5Z,8Z,11Z,13E)-(15S)-15-Hydroxyicosa-5,8,11,13-tetraenoateGenerator
(5Z,8Z,11Z,13E,15S)-15-Hydroxy-5,8,11,13-eicosatetraenoateGenerator
(5Z,8Z,11Z,13E,15S)-15-Hydroxyeicosa-5,8,11,13-tetraenoateGenerator
15(S)-HydroxyeicosatetraenoateGenerator
(15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosic acidHMDB
(15S,5Z,8Z,11Z,13E)-15-HydroxyeicosatetraenoateHMDB
(15S,5Z,8Z,11Z,13E)-15-Hydroxyeicosatetraenoic acidHMDB
(S)-15-HETEHMDB
15 HeteHMDB
15(S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateHMDB
15(S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acidHMDB
15-HETEHMDB
15S-Hydroxy-5Z,8Z,11Z,13E-eicosatetraenoateHMDB
15S-Hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acidHMDB
15-Hydroxy-5,8,11,13-eicosatetraenoic acidMeSH
15-Hydroxy-5,8,11,13-eicosatetraenoic acid, (S-(e,Z,Z,Z))-isomerMeSH
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5Z,8Z,11Z,13E,15S)-15-hydroxyicosa-5,8,11,13-tetraenoic acid
Traditional Name15 hete
CAS Registry Number54845-95-3
SMILES
CCCCC[C@H](O)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1
InChI KeyJSFATNQSLKRBCI-VAEKSGALSA-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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

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
LogP4.405Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0019 g/LALOGPS
logP5.82ALOGPS
logP5.36ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.47 m³·mol⁻¹ChemAxon
Polarizability38.15 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, Positivesplash10-0zml-8392000000-2392d150cc271ce3a20aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00bc-9224200000-28bb287a1a8aa8319f91View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014i-0269000000-6b7e052cfd2bb97562deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0ldi-0398000000-ff190e7ef4788dc235b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0pvi-0395000000-5aefff1d8848add1df10View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0pdi-0693000000-f4fd2c47e2e2d4e7686cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-004i-1591000000-9d6de8ee88a3df3306d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-004i-0920000000-2023bab46b9a229c4bcfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0002-3900000000-133a226bf0eb8235ececView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-052g-3900000000-084e1bd7da1469eba9c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0aq9-5900000000-3d240e182d4edd31c981View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0059000000-c05583912116817f993dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0r99-5393000000-12d4bc503332183deaa1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9740000000-536a9943ef814b845ee2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-c73882d7441506b152edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2169000000-bf33f63d6dfd38c0babfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9130000000-9448e55ece175750c0fbView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
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
Displaying entries 1 - 5 of 41 in total
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.02 +/- 0.01 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.07 +/- 0.03 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified1.12 +/- 0.42 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0018 +/- 0.000098 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00243 +/- 0.00148 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00204 +/- 0.0012 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0008 +/- 2.3E-5 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00048 +/- 0.00024 uMAdult (>18 years old)Both
Normal
    • John W. Newman, U...
details
UrineDetected and Quantified0.000000078 (0.00-0.000000156) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.000014 (0.00000905-0.000019) umol/mmol creatinineChildren (1-13 years old)BothZellweger syndrome details
Associated Disorders and Diseases
Disease References
Peroxisomal biogenesis defect
    MetaGene
Associated OMIM IDs
  • 214100 (Peroxisomal biogenesis defect)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023242
KNApSAcK IDNot Available
Chemspider ID4444307
KEGG Compound IDC04742
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280724
PDB IDNot Available
ChEBI ID15558
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Fogh K, Kragballe K: Eicosanoids in inflammatory skin diseases. Prostaglandins Other Lipid Mediat. 2000 Nov;63(1-2):43-54. [PubMed:11104340 ]

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 + 15(S)-HPETE → Oxidized glutathione + 15(S)-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 + 15(S)-HPETE → Oxidized glutathione + 15(S)-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 + 15(S)-HPETE → Oxidized glutathione + 15(S)-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 + 15(S)-HPETE → Oxidized glutathione + 15(S)-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 + 15(S)-HPETE → Oxidized glutathione + 15(S)-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 + 15(S)-HPETE → Oxidized glutathione + 15(S)-HETE + Waterdetails