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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 06:28:20 UTC
Update Date2022-03-07 02:49:19 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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.405Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+187.37731661259
DarkChem[M-H]-187.49231661259
DeepCCS[M+H]+190.57630932474
DeepCCS[M-H]-188.21830932474
DeepCCS[M-2H]-221.10430932474
DeepCCS[M+Na]+196.66930932474
AllCCS[M+H]+186.832859911
AllCCS[M+H-H2O]+183.932859911
AllCCS[M+NH4]+189.532859911
AllCCS[M+Na]+190.332859911
AllCCS[M-H]-185.732859911
AllCCS[M+Na-2H]-187.532859911
AllCCS[M+HCOO]-189.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
15-HETECCCCC[C@H](O)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O4190.4Standard polar33892256
15-HETECCCCC[C@H](O)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O2385.7Standard non polar33892256
15-HETECCCCC[C@H](O)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O2587.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
15-HETE,1TMS,isomer #1CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C2736.5Semi standard non polar33892256
15-HETE,1TMS,isomer #2CCCCC[C@H](O)/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2634.4Semi standard non polar33892256
15-HETE,2TMS,isomer #1CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2711.7Semi standard non polar33892256
15-HETE,1TBDMS,isomer #1CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C2978.6Semi standard non polar33892256
15-HETE,1TBDMS,isomer #2CCCCC[C@H](O)/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2876.5Semi standard non polar33892256
15-HETE,2TBDMS,isomer #1CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3200.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 15-HETE GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zml-8392000000-2392d150cc271ce3a20a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15-HETE GC-MS (2 TMS) - 70eV, Positivesplash10-00bc-9224200000-28bb287a1a8aa8319f912017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15-HETE GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 15-HETE LC-ESI-QIT , negative-QTOFsplash10-014i-0269000000-6b7e052cfd2bb97562de2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 15-HETE LC-ESI-QIT , negative-QTOFsplash10-0ldi-0398000000-ff190e7ef4788dc235b42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 15-HETE LC-ESI-QIT , negative-QTOFsplash10-0pvi-0395000000-5aefff1d8848add1df102017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 15-HETE LC-ESI-QIT , negative-QTOFsplash10-0pdi-0693000000-f4fd2c47e2e2d4e7686c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 15-HETE LC-ESI-QIT , negative-QTOFsplash10-004i-1591000000-9d6de8ee88a3df3306d72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 15-HETE LC-ESI-QIT , negative-QTOFsplash10-004i-0920000000-2023bab46b9a229c4bcf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 15-HETE LC-ESI-QIT , negative-QTOFsplash10-0002-3900000000-133a226bf0eb8235ecec2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 15-HETE LC-ESI-QIT , negative-QTOFsplash10-052g-3900000000-084e1bd7da1469eba9c32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 15-HETE LC-ESI-QIT , negative-QTOFsplash10-0aq9-5900000000-3d240e182d4edd31c9812017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-HETE 10V, Positive-QTOFsplash10-0uk9-0059000000-c05583912116817f993d2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-HETE 20V, Positive-QTOFsplash10-0r99-5393000000-12d4bc503332183deaa12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-HETE 40V, Positive-QTOFsplash10-0ab9-9740000000-536a9943ef814b845ee22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-HETE 10V, Negative-QTOFsplash10-014i-0019000000-c73882d7441506b152ed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-HETE 20V, Negative-QTOFsplash10-014i-2169000000-bf33f63d6dfd38c0babf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-HETE 40V, Negative-QTOFsplash10-0a4l-9130000000-9448e55ece175750c0fb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-HETE 10V, Positive-QTOFsplash10-0udi-0459000000-f09ca4984311e76513532021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-HETE 20V, Positive-QTOFsplash10-0f79-1973000000-22e0f4adf8c461582eab2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-HETE 40V, Positive-QTOFsplash10-015c-9710000000-f42bad5d652833e0ca312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-HETE 10V, Negative-QTOFsplash10-0gb9-0009000000-f96c871128e9efc2ab452021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-HETE 20V, Negative-QTOFsplash10-0uxr-1249000000-87b24140b02466ab64c82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-HETE 40V, Negative-QTOFsplash10-052f-9130000000-3363d939385a8427ba5e2021-09-22Wishart LabView Spectrum
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
MarkerDB IDMDB00000433
Good Scents 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