11,12-DiHETrE (BioDeep_00000004021)

Main id: BioDeep_00000629480

 

human metabolite Endogenous blood metabolite natural product


代谢物信息卡片


(+/-)-11,12-dihydroxy-5Z,8Z,14Z,17Z-eicosatetraenoic acid

化学式: C20H34O4 (338.2457)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 50%

分子结构信息

SMILES: CCCCC/C=C\CC(C(C/C=C\C/C=C\CCCC(=O)O)O)O
InChI: InChI=1S/C20H34O4/c1-2-3-4-5-9-12-15-18(21)19(22)16-13-10-7-6-8-11-14-17-20(23)24/h6,8-10,12-13,18-19,21-22H,2-5,7,11,14-17H2,1H3,(H,23,24)

描述信息

11,12-DiHETrE is a Cytochrome P450 (P450) eicosanoid. Arachidonic acid may be oxygenated by cytochrome P450 in several ways. Epoxidation of the double bonds leads to the regio- and enantioselective formation of four epoxyeicosatrienoic acids (EETs), which are hydrolyzed by epoxide hydrolase to vicinal diols (DHETs). 11,12-DiHETrE excretion is increased in healthy pregnant women compared with nonpregnant female volunteers, and increased even further in patients with pregnancy-induced hypertension (PIH). The physiological significance of arachidonic acid epoxides has been debated and it is unknown whether they play a role in pregnancy and parturition. Vasodilative effects, inhibition of cyclooxygenase, or inhibition of platelet aggregation by EETs have been observed only at micromolar concentrations. On the other hand, effects on the stimulus-secretion coupling during hormone release have been found in the nanomolar and picomolar range. (PMID: 9440131, 2198572) [HMDB]
11,12-DiHETrE is a Cytochrome P450 (P450) eicosanoid. Arachidonic acid may be oxygenated by cytochrome P450 in several ways. Epoxidation of the double bonds leads to the regio- and enantioselective formation of four epoxyeicosatrienoic acids (EETs), which are hydrolyzed by epoxide hydrolase to vicinal diols (DHETs). 11,12-DiHETrE excretion is increased in healthy pregnant women compared with nonpregnant female volunteers, and increased even further in patients with pregnancy-induced hypertension (PIH). The physiological significance of arachidonic acid epoxides has been debated and it is unknown whether they play a role in pregnancy and parturition. Vasodilative effects, inhibition of cyclooxygenase, or inhibition of platelet aggregation by EETs have been observed only at micromolar concentrations. On the other hand, effects on the stimulus-secretion coupling during hormone release have been found in the nanomolar and picomolar range. (PMID: 9440131, 2198572).

同义名列表

19 个代谢物同义名

(+/-)-11,12-dihydroxy-5Z,8Z,14Z,17Z-eicosatetraenoic acid; (±)11,12-dihydroxy-5Z,8Z,14Z-eicosatrienoic acid; (5Z,8Z,14Z)-11,12-Dihydroxyeicosa-5,8,14-trienoic acid; (+/-)-11,12-dihydroxy-5Z,8Z,14Z,17Z-eicosatetraenoate; (5Z,8Z,14Z)-11,12-Dihydroxyicosa-5,8,14-trienoic acid; (5Z,8Z,14Z)-11,12-Dihydroxyeicosa-5,8,14-trienoate; (5Z,8Z,14Z)-11,12-Dihydroxyicosa-5,8,14-trienoate; 11,12-dihydroxy-5Z,8Z,14Z-eicosatrienoic acid; 11,12-Dihydroxy-5Z,8Z,14Z-eicosatrienoate; 11,12-Dihydroxyicosa-5,8,14-trienoic acid; 12-Dihydroxyicosa-5,8,14-trienoic acid; 12-Dihydroxyicosa-5,8,14-trienoate; 11,12-Dihydroxyeicosatrienoic acid; 11,12-Dihydroxyeicosatrienoate; (±)11,12-DHET; (+/-)11,12-DiHETrE; 11,12-DiHETrE; 11,12-DiHETE; 11,12-DHET



数据库引用编号

15 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

47 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(46)

PharmGKB(0)

9 个相关的物种来源信息

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。

亚细胞结构定位 关联基因列表
Cytoplasm 8 CYP1A1, CYP2C19, CYP2C8, CYP2J2, EGFR, NOS3, PTGS2, TXNRD2
Peripheral membrane protein 3 CYP1A1, CYP1B1, PTGS2
Endosome membrane 1 EGFR
Endoplasmic reticulum membrane 8 CD4, CYP1A1, CYP1B1, CYP2C19, CYP2C8, CYP2J2, EGFR, PTGS2
Nucleus 6 EGFR, GABPA, KLF9, MN1, NOS3, THRB
cytosol 5 AVP, EPHX2, KLF9, NOS3, TXNRD2
dendrite 2 AVP, TXNRD2
nuclear body 1 THRB
nucleoplasm 5 ATP2B1, GABPA, KLF9, NOS3, THRB
RNA polymerase II transcription regulator complex 1 THRB
Cell membrane 5 ATP2B1, CD4, EGFR, KCNMA1, TNF
ruffle membrane 1 EGFR
Early endosome membrane 1 EGFR
Multi-pass membrane protein 2 ATP2B1, KCNMA1
Synapse 1 ATP2B1
cell junction 1 EGFR
cell surface 2 EGFR, TNF
glutamatergic synapse 2 ATP2B1, EGFR
Golgi apparatus 1 NOS3
Golgi membrane 2 EGFR, NOS3
mitochondrial inner membrane 1 CYP1A1
neuronal cell body 2 TNF, TXNRD2
presynaptic membrane 1 ATP2B1
endosome 1 EGFR
plasma membrane 9 ATP2B1, CD4, CYP2C19, CYP2C8, EGFR, KCNMA1, KLF9, NOS3, TNF
synaptic vesicle membrane 1 ATP2B1
Membrane 5 ATP2B1, CYP1B1, CYP2J2, EGFR, KCNMA1
apical plasma membrane 2 EGFR, KCNMA1
axon 1 TXNRD2
basolateral plasma membrane 2 ATP2B1, EGFR
caveola 3 KCNMA1, NOS3, PTGS2
extracellular exosome 3 ATP2B1, CYP2J2, EPHX2
endoplasmic reticulum 1 PTGS2
extracellular space 4 AVP, CRP, EGFR, TNF
perinuclear region of cytoplasm 2 EGFR, NOS3
mitochondrion 3 CYP1A1, CYP1B1, TXNRD2
protein-containing complex 2 EGFR, PTGS2
intracellular membrane-bounded organelle 6 ATP2B1, CYP1A1, CYP1B1, CYP2C19, CYP2C8, CYP2J2
Microsome membrane 4 CYP1A1, CYP1B1, CYP2J2, PTGS2
Single-pass type I membrane protein 2 CD4, EGFR
Secreted 2 AVP, CRP
extracellular region 3 AVP, CRP, TNF
mitochondrial matrix 1 TXNRD2
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
nuclear membrane 1 EGFR
external side of plasma membrane 2 CD4, TNF
Cytoplasm, P-body 1 NOS3
P-body 1 NOS3
Early endosome 1 CD4
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 1 KCNMA1
Mitochondrion inner membrane 1 CYP1A1
Membrane raft 3 CD4, EGFR, TNF
focal adhesion 1 EGFR
Peroxisome 1 EPHX2
intracellular vesicle 1 EGFR
peroxisomal matrix 1 EPHX2
secretory granule 1 AVP
lateral plasma membrane 1 ATP2B1
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 1 EGFR
neuron projection 1 PTGS2
chromatin 3 GABPA, KLF9, THRB
cell projection 1 ATP2B1
phagocytic cup 1 TNF
cytoskeleton 1 NOS3
Basolateral cell membrane 1 ATP2B1
Cytoplasm, Stress granule 1 NOS3
cytoplasmic stress granule 1 NOS3
Presynaptic cell membrane 1 ATP2B1
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
voltage-gated potassium channel complex 1 KCNMA1
endoplasmic reticulum lumen 2 CD4, PTGS2
endocytic vesicle membrane 1 NOS3
immunological synapse 1 ATP2B1
neuronal dense core vesicle 1 AVP
clathrin-coated endocytic vesicle membrane 3 AVP, CD4, EGFR
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
T cell receptor complex 1 CD4
photoreceptor ribbon synapse 1 ATP2B1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


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]
  • Anne Marowsky, Imke Meyer, Kira Erismann-Ebner, Giovanni Pellegrini, Nandkishor Mule, Michael Arand. Beyond detoxification: a role for mouse mEH in the hepatic metabolism of endogenous lipids. Archives of toxicology. 2017 Nov; 91(11):3571-3585. doi: 10.1007/s00204-017-2060-4. [PMID: 28975360]
  • Dina Ripken, Mark van Avesaat, Freddy J Troost, Ad A Masclee, Renger F Witkamp, Henk F Hendriks. Intraileal casein infusion increases plasma concentrations of amino acids in humans: A randomized cross over trial. Clinical nutrition (Edinburgh, Scotland). 2017 02; 36(1):143-149. doi: 10.1016/j.clnu.2016.01.012. [PMID: 26872548]
  • Jinu Kim, Sang Pil Yoon, Myron L Toews, John D Imig, Sung Hee Hwang, Bruce D Hammock, Babu J Padanilam. Pharmacological inhibition of soluble epoxide hydrolase prevents renal interstitial fibrogenesis in obstructive nephropathy. American journal of physiology. Renal physiology. 2015 Jan; 308(2):F131-9. doi: 10.1152/ajprenal.00531.2014. [PMID: 25377915]
  • Yindi Ding, Timo Frömel, Rüdiger Popp, John R Falck, Wolf-Hagen Schunck, Ingrid Fleming. The biological actions of 11,12-epoxyeicosatrienoic acid in endothelial cells are specific to the R/S-enantiomer and require the G(s) protein. The Journal of pharmacology and experimental therapeutics. 2014 Jul; 350(1):14-21. doi: 10.1124/jpet.114.214254. [PMID: 24763066]
  • Mohamed Abukhashim, Glenis J Wiebe, John M Seubert. Regulation of forskolin-induced cAMP production by cytochrome P450 epoxygenase metabolites of arachidonic acid in HEK293 cells. Cell biology and toxicology. 2011 Oct; 27(5):321-32. doi: 10.1007/s10565-011-9190-x. [PMID: 21519968]