12,13-DiHOME (BioDeep_00000002665)
Secondary id: BioDeep_00001872290
human metabolite Endogenous blood metabolite natural product
代谢物信息卡片
化学式: C18H34O4 (314.2457)
中文名称: 12,13-二羟基-9-十八碳烯酸
谱图信息:
最多检出来源 Homo sapiens(plant) 35.64%
Last reviewed on 2024-09-13.
Cite this Page
12,13-DiHOME. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China.
https://query.biodeep.cn/s/12,13-dihome (retrieved
2024-12-22) (BioDeep RN: BioDeep_00000002665). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
分子结构信息
SMILES: CCCCCC(C(C/C=C\CCCCCCCC(=O)O)O)O
InChI: InChI=1S/C18H34O4/c1-2-3-10-13-16(19)17(20)14-11-8-6-4-5-7-9-12-15-18(21)22/h8,11,16-17,19-20H,2-7,9-10,12-15H2,1H3,(H,21,22)
描述信息
12,13-DHOME (CAS: 263399-35-5), also known as 12,13-dihydroxy-9-octadecenoic acid or 12,13-DiHOME, is the epoxide hydrolase metabolite of the leukotoxin 12,13-EpOME. 12,13-EpOME acts as a protoxin, with the corresponding epoxide hydrolase 12,13-DHOME specifically exerting toxicity. Both the EpOME and the DHOME are shown to have neutrophil chemotactic activity. 12,13-DHOME suppress the neutrophil respiratory burst by a mechanism distinct from that of respiratory burst inhibitors such as cyclosporin H or lipoxin A4, which inhibit multiple aspects of neutrophil activation. 12,13-DHOME is a derivative of the linoleic acid diol that has been reported to be toxic in human tissue preparations. 12,13-DHOME is a naturally occurring proliferator-activated receptor (PPAR) gamma2 ligand, which stimulates adipocytes and inhibits osteoblast differentiation (PMID: 17435320, 12021203, 12127265).
12,13-DHOME is the epoxide hydrolase metabolite of the leukotoxin12,13-EpOME. 12,13-EpOMEs act as a protoxin, with the corresponding epoxide hydrolase 12,13-DiHOME specifically exerting toxicity. Both the EpOME and the DiHOME are shown to have neutrophil chemotactic activity. 12,13-DiHOME suppress the neutrophil respiratory burst by a mechanism distinct from that of respiratory burst inhibitors such as cyclosporin H or lipoxin A4,which inhibit multiple aspects of neutrophil activation. 12,13-DHOME is a derivative of linoleic acid diol that have been reported to be toxic in humans tissue preparations. 12,13-DHOME is a naturally occurring proliferator-activated receptor (PPAR) gamma2 ligand, which stimulates adipocytes and inhibits osteoblast differentiation. (PMID: 17435320, 12021203, 12127265) [HMDB]
同义名列表
15 个代谢物同义名
(9Z,12S,13S)-12,13-dihydroxyoctadec-9-enoic acid; (9Z,12S,13S)-12,13-Dihydroxy-9-octadecenoic acid; (9Z)-12,13-Dihydroxy-9-octadecenoic acid; (9Z)-12,13-Dihydroxyoctadec-9-enoic acid; 12,13-dihydroxy-9Z-octadecenoic acid; (9Z)-12,13-Dihydroxyoctadec-9-enoate; 12,13-dihydroxyoctadec-9-enoic acid; (-)-Threo-12,13-dihydroxyoleic acid; FA(18:1(9Z,12S-OH,13S-OH)); 12,13-Dihydroxyoleate; FA(18:1(9Z,12S,13S)); 12,13-DiHOME; 12,13-DHOME; 12,13-DHOA; FA 18:1;O2
数据库引用编号
18 个数据库交叉引用编号
- ChEBI: CHEBI:167825
- ChEBI: CHEBI:72665
- KEGG: C14829
- PubChem: 25320870
- PubChem: 10236635
- PubChem: 53394649
- HMDB: HMDB0004705
- Metlin: METLIN35698
- LipidMAPS: LMFA02000230
- MetaCyc: CPD-13086
- foodb: FDB023416
- chemspider: 26324122
- CAS: 263399-35-5
- PMhub: MS000004348
- PubChem: 17395827
- NIKKAJI: J470.613G
- RefMet: 12,13-DiHOME
- LOTUS: LTS0211698
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
2 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(2)
- Linoleic acid oxylipin metabolism:
12(13)-EpOME ⟶ 12,13-DiHOME - Octadecanoid formation from linoleic acid:
10-HODA ⟶ 9(Z)-OME Oleic Acid
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
11 个相关的物种来源信息
- 4118 - Convolvulaceae: LTS0211698
- 7227 - Drosophila melanogaster: 10.1038/S41467-019-11933-Z
- 2759 - Eukaryota: LTS0211698
- 9606 - Homo sapiens: -
- 4119 - Ipomoea: LTS0211698
- 35883 - Ipomoea nil: 10.3987/COM-07-11291
- 35883 - Ipomoea nil: LTS0211698
- 3398 - Magnoliopsida: LTS0211698
- 35493 - Streptophyta: LTS0211698
- 58023 - Tracheophyta: LTS0211698
- 33090 - Viridiplantae: LTS0211698
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics.
Scientific reports.
2018 07; 8(1):10056. doi:
10.1038/s41598-018-28477-9. [PMID: 29968805] - Lindsay M Edwards, Nathan G Lawler, Sonja B Nikolic, James M Peters, James Horne, Richard Wilson, Noel W Davies, James E Sharman. Metabolomics reveals increased isoleukotoxin diol (12,13-DHOME) in human plasma after acute Intralipid infusion.
Journal of lipid research.
2012 Sep; 53(9):1979-86. doi:
10.1194/jlr.p027706. [PMID: 22715155] - Ching T Hou. New bioactive fatty acids.
Asia Pacific journal of clinical nutrition.
2008; 17 Suppl 1(?):192-5. doi:
. [PMID: 18296335]
