15(S)-HPETE (BioCAD00000001964)

blood

Metabolite Card

Formula: C20H32O4 (336.23)
SMILES: CCCCC[C@H](OO)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O

Synonyms [en]

15(S)-HPETE; 15S-HpETE; 15-Hydroperoxyicosatetraenoate; 15-Hydroperoxyeicosatetraenoic acid; 15-Hydroperoxyicosatetraenoic acid; (5Z,8Z,11Z,13E)-(15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

15(S)-HPETE. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000001964). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

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, 15723435, 8655602, 8595608, 2662983).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 126873-50-5
  • CAS Registry Number: 70981-96-3
  • PubChem: 5280893
  • ChEBI: ChEBI:15628
  • HMDB: HMDB0004244
  • LipidMaps: LMFA03060014
  • KEGG: C05966
  • NCBI MeSH: 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid
  • RefMet: RM0152260
  • Metlin: METLIN_36283
  • Metlin: METLIN_3846
  • Coconut NaturalProduct: CNP0026600.1
  • Coconut NaturalProduct: CNP0026600.2
  • Coconut NaturalProduct: CNP0026600.3
  • Coconut NaturalProduct: CNP0026600.4
  • Coconut NaturalProduct: CNP0193711.1
  • Coconut NaturalProduct: CNP0193711.3
  • Coconut NaturalProduct: CNP0193711.4
  • Coconut NaturalProduct: CNP0296175.2
  • Coconut NaturalProduct: CNP0310864.1
  • Coconut NaturalProduct: CNP0310864.2
  • Coconut NaturalProduct: CNP0310864.3
  • Coconut NaturalProduct: CNP0310864.4

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R01593 1.13.11.33 arachidonate:oxygen 15-oxidoreductase
KEGG:R07035 1.11.1.12 glutathione: 15-HPETE oxidoreductase
KEGG:R07042 1.14.14.1 C05966<=>C14781
KEGG:R07043 1.14.14.1 C05966<=>C14813
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Organism Source

Taxonomy Source

  1. Homo sapiens [ncbi taxid: 9606]
  2. Mus musculus [ncbi taxid: 10090]
  3. Saprolegnia parasitica [ncbi taxid: 101203]

Pathway Synthetic

pathway id name
WikiPathways:WP4721 Eicosanoid metabolism via lipooxygenases (LOX)
WikiPathways:WP4348 Eicosanoid metabolism via lipoxygenases (LOX)
WikiPathways:WP167 Eicosanoid synthesis
PathBank:SMP0120730 Leukotriene C4 Synthesis Deficiency
PathBank:SMP0000083 Acetylsalicylic Acid Action Pathway
PathBank:SMP0000087 Rofecoxib Action Pathway
PathBank:SMP0000094 Sulindac Action Pathway
PathBank:SMP0000104 Indomethacin Action Pathway
PathBank:SMP0000120 Naproxen Action Pathway
PathBank:SMP0000106 Meloxicam Action Pathway
PathBank:SMP0000693 Antrafenine Action Pathway
PathBank:SMP0000697 Flurbiprofen Action Pathway
PathBank:SMP0000701 Phenylbutazone Action Pathway
PathBank:SMP0000705 Tiaprofenic Acid Action Pathway
PathBank:SMP0000709 Salicylic Acid Action Pathway
PathBank:SMP0000075 Arachidonic Acid Metabolism
PathBank:SMP0000086 Ibuprofen Action Pathway
PathBank:SMP0000093 Diclofenac Action Pathway
PathBank:SMP0000098 Ketorolac Action Pathway
PathBank:SMP0000102 Bromfenac Action Pathway
View All Pathways