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Record Information
Version3.6
Creation Date2006-08-13 06:28:20 UTC
Update Date2016-02-11 01:06:27 UTC
HMDB IDHMDB03876
Secondary Accession Numbers
  • HMDB02110
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
(5Z,8Z,11Z,13E,15S)-15-Hydroxyicosa-5,8,11,13-tetraenoateGenerator
(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
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 KeyInChIKey=JSFATNQSLKRBCI-VAEKSGALSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatetraenoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.47 m3·mol-1ChemAxon
Polarizability38.15 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Acetaminophen Action PathwaySMP00710Not Available
Acetylsalicylic Acid PathwaySMP00083Not Available
Antipyrine Action PathwaySMP00692Not Available
Antrafenine Action PathwaySMP00693Not Available
Arachidonic Acid MetabolismSMP00075map00590
Bromfenac PathwaySMP00102Not Available
Carprofen Action PathwaySMP00694Not Available
Celecoxib PathwaySMP00096Not Available
Diclofenac PathwaySMP00093Not Available
Diflunisal PathwaySMP00289Not Available
Etodolac PathwaySMP00084Not Available
Etoricoxib Action PathwaySMP00695Not Available
Fenoprofen Action PathwaySMP00696Not Available
Flurbiprofen Action PathwaySMP00697Not Available
Ibuprofen PathwaySMP00086Not Available
Indomethacin PathwaySMP00104Not Available
Ketoprofen PathwaySMP00085Not Available
Ketorolac PathwaySMP00098Not Available
Leukotriene C4 Synthesis DeficiencySMP00353Not Available
Lornoxicam Action PathwaySMP00700Not Available
Lumiracoxib Action PathwaySMP00699Not Available
Magnesium salicylate Action PathwaySMP00698Not Available
Mefanamic Acid PathwaySMP00109Not Available
Meloxicam PathwaySMP00106Not Available
Nabumetone PathwaySMP00114Not Available
Naproxen PathwaySMP00120Not Available
Nepafenac Action PathwaySMP00702Not Available
Oxaprozin PathwaySMP00113Not Available
Phenylbutazone Action PathwaySMP00701Not Available
Piroxicam PathwaySMP00077Not Available
Rofecoxib PathwaySMP00087Not Available
Salicylate-sodium Action PathwaySMP00708Not Available
Salicylic Acid Action PathwaySMP00709Not Available
Salsalate Action PathwaySMP00707Not Available
Sulindac PathwaySMP00094Not Available
Suprofen PathwaySMP00101Not Available
Tenoxicam Action PathwaySMP00706Not Available
Tiaprofenic Acid Action PathwaySMP00705Not Available
Tolmetin Action PathwaySMP00704Not Available
Trisalicylate-choline Action PathwaySMP00703Not Available
Valdecoxib PathwaySMP00116Not Available
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
  1. MetaGene [Link]
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
NuGOwiki LinkHMDB03876
Metagene LinkHMDB03876
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. [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