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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 06:28:20 UTC
Update Date2020-02-26 21:24:49 UTC
HMDB IDHMDB0003876
Secondary Accession Numbers
  • HMDB0002110
  • HMDB02110
  • HMDB03876
Metabolite Identification
Common Name15-HETE
Description15-HETE is a hydroxyeicosatetraenoic acid. Hydroxyeicosatetraenoic acids (HETEs) are formed by the 5-, 12-, and 15-lipoxygenase (LO) pathways. The 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 also has 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 ). 15(S)-HETE is found to be associated with Zellweger syndrome, which is an inborn error of metabolism.
Structure
Data?1582752289
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
15(S)-HETEKegg
(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
15-Hydroxy-5,8,11,13-eicosatetraenoic acidHMDB
15-Hydroxy-5,8,11,13-eicosatetraenoic acid, (S-(e,Z,Z,Z))-isomerHMDB
(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
15S-Hydroxy-5Z,8Z,11Z,13E-eicosatetraenoateHMDB
15S-Hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acidHMDB
(5Z,8Z,11Z,13E,15S)-15-Hydroxyeicosatetraenoic acidHMDB
15(S)-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoic acidHMDB
15(S)-Hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acidHMDB
15-Hydroxyeicosatetraenoic acidHMDB
15S-Hydroxy-5,8,11,13-(Z,Z,Z,e)-eicosatetraenoic acidHMDB
FA(20:4(5Z,8Z,11Z,13E,15-OH))HMDB
FA(20:4(5Z,8Z,11Z,13E,15S-OH))HMDB
15-HETEHMDB, MeSH
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
Description 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
  • 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:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring 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 Solubility0.002 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zml-8392000000-2392d150cc271ce3a20aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00bc-9224200000-28bb287a1a8aa8319f91Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014i-0269000000-6b7e052cfd2bb97562deSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0ldi-0398000000-ff190e7ef4788dc235b4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0pvi-0395000000-5aefff1d8848add1df10Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0pdi-0693000000-f4fd2c47e2e2d4e7686cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-004i-1591000000-9d6de8ee88a3df3306d7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-004i-0920000000-2023bab46b9a229c4bcfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0002-3900000000-133a226bf0eb8235ececSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-052g-3900000000-084e1bd7da1469eba9c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0aq9-5900000000-3d240e182d4edd31c981Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0059000000-c05583912116817f993dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0r99-5393000000-12d4bc503332183deaa1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9740000000-536a9943ef814b845ee2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-c73882d7441506b152edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2169000000-bf33f63d6dfd38c0babfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9130000000-9448e55ece175750c0fbSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 +/- 0.000023 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 Quantified0-0.00000001560 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified0-1.560e-08 umol/mmol creatinineInfant (0-1 year old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.000008113 (0.000005305-0.00001123) umol/mmol creatinineInfant (0-1 year old)BothZellweger syndrome details
Associated Disorders and Diseases
Disease References
Peroxisomal biogenesis defect
  1. Mayatepek E, Lehmann WD: 12- and 15-hydroxyeicosatetraenoic acid are excreted in the urine of peroxisome-deficient patients: evidence for peroxisomal metabolism in vivo. Pediatr Res. 1996 Jan;39(1):146-9. [PubMed:8825400 ]
  2. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Associated OMIM IDs
  • 214100 (Peroxisomal biogenesis defect)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
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 ]
  2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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-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-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-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-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-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-HETE + Waterdetails