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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 15:07:35 UTC
Update Date2022-03-07 02:49:20 UTC
HMDB IDHMDB0004244
Secondary Accession Numbers
  • HMDB0006501
  • HMDB04244
  • HMDB06501
Metabolite Identification
Common Name15(S)-HPETE
Description15(S)-hydroperoxyeicosatetraenoic acid (15(S)-HPETE) is the corresponding hydroperoxide of 15(S)-HETE and undergoes homolytic decomposition to the DNA-reactive bifunctional electrophile 4-oxo-2(E)-nonenal, a precursor of heptanone-etheno-2'-deoxyguanosine. Reactive oxygen species convert the omega-6 polyunsaturated fatty acid arachidonic acid into (15-HPETE); vitamin C mediates 15(S)-HPETE decomposition. 15(S)-HPETE initiates apoptosis in vascular smooth muscle cells. 15(S)-HPETE is a lipoxygenase metabolite that affects the expression of cell adhesion molecules (CAMs) involved in the adhesion of leukocytes and/or the accumulation of leukocytes in the vascular endothelium, these being the initial events in endothelial cell injury. 15(S)-HPETE induces a loss of cardiomyocytes membrane integrity. 15-(S)HPETE is a hydroperoxide that enhances the activity of the enzymes lipoxygenase [EC 1.13.11.12] and Na+, K+-ATPase [EC 3.6.3.9] of brain microvessels. Lipoxygenase(s) and Na+-K+-ATPase of brain microvessels may play a significant role in the occurrence of ischemic brain edema. (PMID: 15964853 , 15723435 , 8655602 , 8595608 , 2662983 ).
Structure
Data?1582752304
Synonyms
ValueSource
(5Z,8Z,11Z,13E)-(15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoateChEBI
(5Z,8Z,11Z,13E)-(15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoic acidChEBI
15-HydroperoxyeicosatetraenoateChEBI
15-Hydroperoxyeicosatetraenoic acidChEBI
15-HydroperoxyicosatetraenoateChEBI
15-Hydroperoxyicosatetraenoic acidChEBI
15S-HpETEChEBI
(5Z,8Z,11Z,13E,15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoic acidChEBI, HMDB
(5Z,8Z,11Z,13E,15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoateGenerator, HMDB
15S-HydroperoxyeicosatetraenoateHMDB
15S-Hydroperoxyeicosatetraenoic acidHMDB
14,15-Epoxyarachidonic acidMeSH, HMDB
15-HPEAMeSH, HMDB
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (Z,Z,Z,Z)-isomerMeSH, HMDB
15-Hydroperoxyarachidonic acidMeSH, HMDB
15-HPAAMeSH, HMDB
15-HPETEMeSH, HMDB
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acidMeSH, HMDB
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (e,Z,Z,Z)-isomerMeSH, HMDB
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomerMeSH, HMDB
15-Hydroperoxy-5,8,11,14-eicosatetraenoic acidMeSH, HMDB
Arachidonic acid 15-hydroperoxideMeSH, HMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5Z,8Z,11Z,13E,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoic acid
Traditional Name15(S)-hpete
CAS Registry Number70981-96-3
SMILES
CCCCC[C@H](OO)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-13-16-19(24-23)17-14-11-9-7-5-4-6-8-10-12-15-18-20(21)22/h4-5,8-11,14,17,19,23H,2-3,6-7,12-13,15-16,18H2,1H3,(H,21,22)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1
InChI KeyBFWYTORDSFIVKP-VAEKSGALSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroperoxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and four CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroperoxyeicosatetraenoic acids
Alternative Parents
Substituents
  • Hydroperoxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroperoxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Allylic hydroperoxide
  • Hydroperoxide
  • Carboxylic acid derivative
  • Alkyl hydroperoxide
  • Carboxylic acid
  • Peroxol
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0018 g/LALOGPS
logP5.86ALOGPS
logP5.81ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity102.82 m³·mol⁻¹ChemAxon
Polarizability38.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+191.04931661259
DarkChem[M-H]-190.29731661259
DeepCCS[M+H]+190.10630932474
DeepCCS[M-H]-187.74830932474
DeepCCS[M-2H]-220.63430932474
DeepCCS[M+Na]+196.19930932474
AllCCS[M+H]+190.432859911
AllCCS[M+H-H2O]+187.632859911
AllCCS[M+NH4]+193.032859911
AllCCS[M+Na]+193.832859911
AllCCS[M-H]-188.132859911
AllCCS[M+Na-2H]-190.032859911
AllCCS[M+HCOO]-192.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
15(S)-HPETECCCCC[C@H](OO)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O4175.9Standard polar33892256
15(S)-HPETECCCCC[C@H](OO)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O2411.1Standard non polar33892256
15(S)-HPETECCCCC[C@H](OO)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O2671.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
15(S)-HPETE,1TMS,isomer #1CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)OO2758.5Semi standard non polar33892256
15(S)-HPETE,1TBDMS,isomer #1CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)OO2997.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 15(S)-HPETE GC-MS (Non-derivatized) - 70eV, Positivesplash10-0296-7691000000-10e52eac953fb64dc1a62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15(S)-HPETE GC-MS (1 TMS) - 70eV, Positivesplash10-00vr-9343000000-559ae101ce63837aa2c62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15(S)-HPETE GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15(S)-HPETE GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-HPETE 10V, Positive-QTOFsplash10-014i-0129000000-35e1b05b3a271d79d7fe2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-HPETE 20V, Positive-QTOFsplash10-066u-3494000000-dfe60ca573a64c8134412017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-HPETE 40V, Positive-QTOFsplash10-0abc-9650000000-4e66ed45e98b64d54b282017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-HPETE 10V, Negative-QTOFsplash10-000i-0019000000-21ceecb44bdf804c0c4b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-HPETE 20V, Negative-QTOFsplash10-01bi-3189000000-29f754a5638ca1b0ae572017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-HPETE 40V, Negative-QTOFsplash10-0a4l-9150000000-81504e73ce15d31bbd082017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-HPETE 10V, Negative-QTOFsplash10-0f79-0019000000-b91b825f9248bd953b5b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-HPETE 20V, Negative-QTOFsplash10-0udi-0059000000-c3891e970dfe8176e4a02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-HPETE 40V, Negative-QTOFsplash10-0002-8091000000-62e6f1d45410fc34c98c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-HPETE 10V, Positive-QTOFsplash10-0udr-0359000000-aaf43f18f05b65e0a9492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-HPETE 20V, Positive-QTOFsplash10-0f79-1896000000-b6c85b7e90a53a2752ab2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15(S)-HPETE 40V, Positive-QTOFsplash10-00l6-9810000000-898d59f193fb8d5136782021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00106 +/- 0.00041 uMAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4444416
KEGG Compound IDC05966
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280893
PDB IDNot Available
ChEBI ID15628
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceDussault, Patrick; Lee, In Quen. The total synthesis of 15(S)-HPETE (hydroperoxyeicosatetraenoic acid). Journal of Organic Chemistry (1992), 57(7), 1952-4.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kuitert LM, Newton R, Barnes NC, Adcock IM, Barnes PJ: Eicosanoid mediator expression in mononuclear and polymorphonuclear cells in normal subjects and patients with atopic asthma and cystic fibrosis. Thorax. 1996 Dec;51(12):1223-8. [PubMed:8994519 ]
  2. Terao J, Nagao A, Yuki H, Itoh Y: Reduction of fatty acid hydroperoxides by human parotid saliva. Lipids. 1993 Feb;28(2):121-4. [PubMed:8441337 ]
  3. Lee SH, Williams MV, Dubois RN, Blair IA: Cyclooxygenase-2-mediated DNA damage. J Biol Chem. 2005 Aug 5;280(31):28337-46. Epub 2005 Jun 17. [PubMed:15964853 ]
  4. Williams MV, Lee SH, Blair IA: Liquid chromatography/mass spectrometry analysis of bifunctional electrophiles and DNA adducts from vitamin C mediated decomposition of 15-hydroperoxyeicosatetraenoic acid. Rapid Commun Mass Spectrom. 2005;19(6):849-58. [PubMed:15723435 ]
  5. Sultana C, Shen Y, Rattan V, Kalra VK: Lipoxygenase metabolites induced expression of adhesion molecules and transendothelial migration of monocyte-like HL-60 cells is linked to protein kinase C activation. J Cell Physiol. 1996 Jun;167(3):477-87. [PubMed:8655602 ]
  6. Thollon C, Iliou JP, Cambarrat C, Robin F, Vilaine JP: Nature of the cardiomyocyte injury induced by lipid hydroperoxides. Cardiovasc Res. 1995 Nov;30(5):648-55. [PubMed:8595608 ]
  7. Asano T, Koide T, Gotoh O, Joshita H, Hanamura T, Shigeno T, Takakura K: The role of free radicals and eicosanoids in the pathogenetic mechanism underlying ischemic brain edema. Mol Chem Neuropathol. 1989 Apr;10(2):101-33. [PubMed:2662983 ]

Only showing the first 10 proteins. There are 33 proteins in total.

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
General function:
Involved in metal ion binding
Specific function:
Converts arachidonic acid exclusively to 15S-hydroperoxyeicosatetraenoic acid, while linoleic acid is less well metabolized.
Gene Name:
ALOX15B
Uniprot ID:
O15296
Molecular weight:
72522.25
Reactions
Arachidonic acid + Oxygen → 15(S)-HPETEdetails
General function:
Involved in metal ion binding
Specific function:
Converts arachidonic acid to 15S-hydroperoxyeicosatetraenoic acid. Also acts on C-12 of arachidonate as well as on linoleic acid.
Gene Name:
ALOX15
Uniprot ID:
P16050
Molecular weight:
74803.795
Reactions
Arachidonic acid + Oxygen → 15(S)-HPETEdetails
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585

Only showing the first 10 proteins. There are 33 proteins in total.