9(10)-EpOME (BioCAD00000005675)
Metabolite Card
Formula: C18H32O3 (296.2351)
SMILES: CCCCC\C=C/CC1OC1CCCCCCCC(O)=O
Synonyms [en]
9(10)-EpOME; Coronaric acid; (9R,10S)-(12Z)-9,10-Epoxyoctadecenoic acid; 9R,10S-EpOME; 9R,10S-epoxy-12Z-octadecenoic acid; 9,10-epoxy-12Z-octadecenoic acid
Last reviewed on 2024-06-28.
Cite this Page
9(10)-EpOME. 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: BioCAD00000005675). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
9,10-Epoxyoctadecenoic acid (9,10-EOA) is a peroxidation product of linoleic acid (LA). 9,10-EOA is a naturally occurring component of oxidized low density lipoprotein (LDL), the level of which increases with aging, atherosclerosis, and rheumatoid arthritis, perhaps due to an increase in 15-lipoxygenase and free oxygen radicals. 9,10-EOA is a proliferator-activated receptors (PPAR) gamma2 ligand, that is antiosteogenic without stimulating adipocyte differentiation. Studies in dogs suggest that 9,10-EOA has toxic cardiovascular effects. (PMID: 12665667, 12021203, 10667371).
DBLinks
- CAS Registry Number: 16833-56-0
- PubChem CID: 6246154
- ChEBI: 86022
- HMDB: HMDB0004701
- LipidMaps: LMFA02000037
- KEGG: C14825
- BioCyc:
- NCBI MeSH: leukotoxin
- Wikipedia: Coronaric_acid
Other DBLinks
- CAS Registry Number: 126639-25-6
- CAS Registry Number: 16833-56-0
- CAS Registry Number: 61949-82-4
- CAS Registry Number: NA
- PubChem: 5316080
- PubChem: 6246154
- ChEBI: ChEBI:34494
- ChEBI: ChEBI:86022
- HMDB: HMDB0004701
- HMDB: HMDB04701
- LipidMaps: LMFA02000037
- LipidMaps: LMFA02000283
- KEGG: C14825
- NCBI MeSH: leukotoxin
- Wikipedia: Coronaric_acid
- RefMet: RM0136956
- RefMet: RM0153718
- MoNA: IA000103
- MoNA: IA000104
- MoNA: IA000105
- MoNA: IA000277
- MoNA: IA000278
- MoNA: IA000279
- MoNA: IA000412
- MoNA: IA000413
- MoNA: IA000414
- Metlin: METLIN_43441
- Coconut NaturalProduct: CNP0251605.1
- Coconut NaturalProduct: CNP0251605.3
Class / Ontology
- WishartLab ClassyFire: [Fatty acids and conjugates] Fatty acids and conjugates
- RefMet: [EpOME] EpOME
- LipidMaps: [Other Octadecanoids [FA0200]] Other Octadecanoids [FA0200]
- ChEBI: [CHEBI:34494] 9(10)-EpOME
- ChEBI: [CHEBI:86022] (9R,10S)-9(10)-EpOME
- Coconut NaturalProduct: [Epoxy fatty acids] Epoxy fatty acids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R07055 | 1.14.14.1 | C01595 + C00007 + C00005 + C00080<=>C14825 + C00006 + C00001 |
| KEGG:R07122 | 3.3.2.- | 9(10)-EpOME hydrolase |
Taxonomy Source
Pathway Synthetic
| pathway id | name |
|---|---|
| WikiPathways:WP5324 | Octadecanoid formation from linoleic acid |