Human Metabolome Database Version 3.5

Showing metabocard for 15(S)-HPETE (HMDB04244)

Record Information
Version 3.5
Creation Date 2006-08-13 09:07:35 -0600
Update Date 2013-05-29 13:40:04 -0600
HMDB ID HMDB04244
Secondary Accession Numbers
  • HMDB06501
Metabolite Identification
Common Name 15(S)-HPETE
Description 15(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 Link_out, 15723435 Link_out, 8655602 Link_out, 8595608 Link_out, 2662983 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C20H32O4
Average Molecular Weight 336.4657
Monoisotopic Molecular Weight 336.230059512
IUPAC Name (5Z,8Z,11Z,13E,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoic acid
Traditional IUPAC Name 15(S)-hpete
CAS Registry Number 70981-96-3
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 Key BFWYTORDSFIVKP-VAEKSGALSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Hydroperoxyeicosatetraenoic 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 Parent Hydroperoxyeicosatetraenoic Acids
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0018 g/L ALOGPS
LogP 5.86 ALOGPS
LogP 5.81 ChemAxon
LogS -5.27 ALOGPS
pKa (strongest acidic) 4.82 ChemAxon
pKa (strongest basic) -4.2 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 66.76 A2 ChemAxon
Rotatable Bond Count 15 ChemAxon
Refractivity 102.82 ChemAxon
Polarizability 38.42 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Arachidonic Acid Metabolism SMP00075 map00590 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
1.06 +/- 0.41 uM Adult (>18 years old) Not Specified Comment Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023349
KNApSAcK ID Not Available
Chemspider ID 4444416 Link_out
KEGG Compound ID C05966 Link_out
BioCyc ID Not Available
BiGG ID 47085 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB04244 Link_out
Metagene Link HMDB04244 Link_out
METLIN ID 7039 Link_out
PubChem Compound 5280893 Link_out
PDB ID Not Available
ChEBI ID 15628 Link_out
References
Synthesis Reference Dussault, 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: Glutathione peroxidase 7
Reactions:
Glutathione + 15(S)-HPETE unknown Oxidized glutathione + 15(S)-HETE + Water details
Gene Name: GPX7
Uniprot ID: Q96SL4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Epididymal secretory glutathione peroxidase
Reactions:
Glutathione + 15(S)-HPETE unknown Oxidized glutathione + 15(S)-HETE + Water details
Gene Name: GPX5
Uniprot ID: O75715 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glutathione peroxidase 6
Reactions:
Glutathione + 15(S)-HPETE unknown Oxidized glutathione + 15(S)-HETE + Water details
Gene Name: GPX6
Uniprot ID: P59796 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glutathione peroxidase 1
Reactions:
Glutathione + 15(S)-HPETE unknown Oxidized glutathione + 15(S)-HETE + Water details
Gene Name: GPX1
Uniprot ID: P07203 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipid hydroperoxide glutathione peroxidase, mitochondrial
Reactions: Not Available
Gene Name: GPX4
Uniprot ID: P36969 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glutathione peroxidase 3
Reactions:
Glutathione + 15(S)-HPETE unknown Oxidized glutathione + 15(S)-HETE + Water details
Gene Name: GPX3
Uniprot ID: P22352 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glutathione peroxidase 2
Reactions:
Glutathione + 15(S)-HPETE unknown Oxidized glutathione + 15(S)-HETE + Water details
Gene Name: GPX2
Uniprot ID: P18283 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Arachidonate 15-lipoxygenase B
Reactions:
Arachidonic acid + Oxygen unknown 15(S)-HPETE details
Gene Name: ALOX15B
Uniprot ID: O15296 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Arachidonate 15-lipoxygenase
Reactions:
Arachidonic acid + Oxygen unknown 15(S)-HPETE details
Gene Name: ALOX15
Uniprot ID: P16050 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C9
Reactions: Not Available
Gene Name: CYP2C9
Uniprot ID: P11712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C19
Reactions: Not Available
Gene Name: CYP2C19
Uniprot ID: P33261 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2E1
Reactions: Not Available
Gene Name: CYP2E1
Uniprot ID: P05181 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A43
Reactions: Not Available
Gene Name: CYP3A43
Uniprot ID: Q9HB55 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1B1
Reactions: Not Available
Gene Name: CYP1B1
Uniprot ID: Q16678 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C18
Reactions: Not Available
Gene Name: CYP2C18
Uniprot ID: P33260 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2F1
Reactions: Not Available
Gene Name: CYP2F1
Uniprot ID: P24903 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4X1
Reactions: Not Available
Gene Name: CYP4X1
Uniprot ID: Q8N118 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2B6
Reactions: Not Available
Gene Name: CYP2B6
Uniprot ID: P20813 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A5
Reactions: Not Available
Gene Name: CYP3A5
Uniprot ID: P20815 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2A13
Reactions: Not Available
Gene Name: CYP2A13
Uniprot ID: Q16696 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A7
Reactions: Not Available
Gene Name: CYP3A7
Uniprot ID: P24462 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4B1
Reactions: Not Available
Gene Name: CYP4B1
Uniprot ID: P13584 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4Z1
Reactions: Not Available
Gene Name: CYP4Z1
Uniprot ID: Q86W10 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A2
Reactions: Not Available
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 19A1
Reactions: Not Available
Gene Name: CYP19A1
Uniprot ID: P11511 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C8
Reactions: Not Available
Gene Name: CYP2C8
Uniprot ID: P10632 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2S1
Reactions: Not Available
Gene Name: CYP2S1
Uniprot ID: Q96SQ9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2J2
Reactions: Not Available
Gene Name: CYP2J2
Uniprot ID: P51589 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2A7
Reactions: Not Available
Gene Name: CYP2A7
Uniprot ID: P20853 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2A6
Reactions: Not Available
Gene Name: CYP2A6
Uniprot ID: P11509 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450, family 1, subfamily A, polypeptide 1
Reactions: Not Available
Gene Name: CYP1A1
Uniprot ID: A0N0X8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: Q6NWU0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA