15(S)-HPETE (BioCAD00000001964)
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
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).
DBLinks
- CAS Registry Number: 70981-96-3
- PubChem CID: 5280893
- ChEBI: 15628
- HMDB: HMDB0004244
- LipidMaps: LMFA03060014
- KEGG: C05966
- BioCyc:
- NCBI MeSH: 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid
- Wikipedia:
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
- WishartLab ClassyFire: [Eicosanoids] Eicosanoids
- RefMet: [HETE] HETE
- LipidMaps: [Hydroxy/hydroperoxyeicosatetraenoic acids [FA0306]] Hydroxy/hydroperoxyeicosatetraenoic acids [FA0306]
- ChEBI: [CHEBI:15628] 15(S)-HPETE
- Coconut NaturalProduct: [Cardenolides] Cardenolides
- Coconut NaturalProduct: [Androstane steroids] Androstane steroids
- Coconut NaturalProduct: [Hydroxy-hydroperoxyeicosatetraenoic acids] Hydroxy-hydroperoxyeicosatetraenoic acids
| 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 |
Taxonomy Source
- Homo sapiens [ncbi taxid: 9606]
- Mus musculus [ncbi taxid: 10090]
- 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 |