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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 15:07:35 UTC
Update Date2018-05-19 22:24:11 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
Thumb
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
(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-tetraenoateGenerator
15S-HydroperoxyeicosatetraenoateHMDB
15S-Hydroperoxyeicosatetraenoic acidHMDB
14,15-Epoxyarachidonic acidMeSH
15-HPEAMeSH
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (Z,Z,Z,Z)-isomerMeSH
15-Hydroperoxyarachidonic acidMeSH
15-HPAAMeSH
15-HPETEMeSH
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acidMeSH
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (e,Z,Z,Z)-isomerMeSH
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomerMeSH
15-Hydroperoxy-5,8,11,14-eicosatetraenoic acidMeSH
Arachidonic acid 15-hydroperoxideMeSH
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
DescriptionThis compound 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
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
LogPNot AvailableNot Available
Predicted 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
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, Positivesplash10-0296-7691000000-10e52eac953fb64dc1a6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00vr-9343000000-559ae101ce63837aa2c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0129000000-35e1b05b3a271d79d7feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066u-3494000000-dfe60ca573a64c813441View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-9650000000-4e66ed45e98b64d54b28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019000000-21ceecb44bdf804c0c4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01bi-3189000000-29f754a5638ca1b0ae57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9150000000-81504e73ce15d31bbd08View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationNot 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
FoodDB IDFDB023349
KNApSAcK IDC00000400
Chemspider ID4444416
KEGG Compound IDC05966
BioCyc IDNot Available
BiGG ID47085
Wikipedia LinkNot Available
METLIN ID7039
PubChem Compound5280893
PDB IDNot Available
ChEBI ID15628
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(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
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.