Record Information
Version3.6
Creation Date2006-08-13 15:07:35 UTC
Update Date2013-05-29 19:40:04 UTC
HMDB IDHMDB04244
Secondary Accession Numbers
  • 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
  1. (5Z,8Z,11Z,13E)-(15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoate
  2. (5Z,8Z,11Z,13E)-(15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid
  3. 15-Hydroperoxyeicosatetraenoate
  4. 15-Hydroperoxyeicosatetraenoic acid
  5. 15-Hydroperoxyicosatetraenoate
  6. 15-Hydroperoxyicosatetraenoic acid
  7. 15S-Hydroperoxyeicosatetraenoate
  8. 15S-Hydroperoxyeicosatetraenoic acid
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 IUPAC 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
KingdomOrganic Compounds
Super ClassLipids
ClassEicosanoids
Sub ClassHydroperoxyeicosatetraenoic Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Hydroperoxy Fatty Acids
  • Organic Compounds
  • Straight Chain Fatty Acids
  • Unsaturated Fatty Acids
Substituents
  • Acyclic Alkene
  • Carboxylic Acid
  • Hydroperoxide
Direct ParentHydroperoxyeicosatetraenoic Acids
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
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
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 area66.76ChemAxon
rotatable bond count15ChemAxon
refractivity102.82ChemAxon
polarizability38.42ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075map00590
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified1.06 +/- 0.41 uMAdult (>18 years old)Not SpecifiedCommentNormal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023349
KNApSAcK IDNot Available
Chemspider ID4444416
KEGG Compound IDC05966
BioCyc IDNot Available
BiGG ID47085
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04244
Metagene LinkHMDB04244
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

Enzymes

Gene Name:
GPX7
Uniprot ID:
Q96SL4
Reactions
Glutathione + 15(S)-HPETE unknown Oxidized glutathione + 15(S)-HETE + Waterdetails
Gene Name:
GPX5
Uniprot ID:
O75715
Reactions
Glutathione + 15(S)-HPETE unknown Oxidized glutathione + 15(S)-HETE + Waterdetails
Gene Name:
GPX6
Uniprot ID:
P59796
Reactions
Glutathione + 15(S)-HPETE unknown Oxidized glutathione + 15(S)-HETE + Waterdetails
Gene Name:
GPX1
Uniprot ID:
P07203
Reactions
Glutathione + 15(S)-HPETE unknown Oxidized glutathione + 15(S)-HETE + Waterdetails
Gene Name:
GPX3
Uniprot ID:
P22352
Reactions
Glutathione + 15(S)-HPETE unknown Oxidized glutathione + 15(S)-HETE + Waterdetails
Gene Name:
GPX2
Uniprot ID:
P18283
Reactions
Glutathione + 15(S)-HPETE unknown Oxidized glutathione + 15(S)-HETE + Waterdetails
Gene Name:
ALOX15B
Uniprot ID:
O15296
Reactions
Arachidonic acid + Oxygen unknown 15(S)-HPETEdetails
Gene Name:
ALOX15
Uniprot ID:
P16050
Reactions
Arachidonic acid + Oxygen unknown 15(S)-HPETEdetails
Gene Name:
CYP3A4
Uniprot ID:
P08684
Gene Name:
CYP2C9
Uniprot ID:
P11712
Gene Name:
CYP2C19
Uniprot ID:
P33261
Gene Name:
CYP2E1
Uniprot ID:
P05181
Gene Name:
CYP3A43
Uniprot ID:
Q9HB55
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Gene Name:
CYP2C18
Uniprot ID:
P33260
Gene Name:
CYP2F1
Uniprot ID:
P24903
Gene Name:
CYP4X1
Uniprot ID:
Q8N118
Gene Name:
CYP2B6
Uniprot ID:
P20813
Gene Name:
CYP3A5
Uniprot ID:
P20815
Gene Name:
CYP2A13
Uniprot ID:
Q16696
Gene Name:
CYP3A7
Uniprot ID:
P24462
Gene Name:
CYP4B1
Uniprot ID:
P13584
Gene Name:
CYP4Z1
Uniprot ID:
Q86W10
Gene Name:
CYP1A2
Uniprot ID:
P05177
Gene Name:
CYP19A1
Uniprot ID:
P11511
Gene Name:
CYP2C8
Uniprot ID:
P10632
Gene Name:
CYP2S1
Uniprot ID:
Q96SQ9
Gene Name:
CYP2J2
Uniprot ID:
P51589
Gene Name:
CYP2A7
Uniprot ID:
P20853
Gene Name:
CYP2A6
Uniprot ID:
P11509
Gene Name:
CYP2D6
Uniprot ID:
Q6NWU0