Dihomolinoleate (20:2n6) (BioDeep_00000002832)

 

Secondary id: BioDeep_00000628818

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite natural product


代谢物信息卡片


(11Z,14Z)-icosa-11,14-dienoic acid

化学式: C20H36O2 (308.2715)
中文名称: 顺-11,14-二十碳二烯酸, 二十碳二烯酸
谱图信息: 最多检出来源 Homo sapiens(not specific) 10.5%

Reviewed

Last reviewed on 2024-09-25.

Cite this Page

Dihomolinoleate (20:2n6). BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/dihomolinoleate_(20:2n6) (retrieved 2024-12-27) (BioDeep RN: BioDeep_00000002832). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CCCCC/C=C/C/C=C/CCCCCCCCCC(O)=O
InChI: InChI=1S/C20H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10H,2-5,8,11-19H2,1H3,(H,21,22)/b7-6-,10-9-

描述信息

Eicosadienoic acid is an omega-6 fatty acid found in human milk (PMID: 15256803). Omega-6 fatty acids are a family of unsaturated fatty acids which have in common a carbon-carbon double bond in the n−6 position; that is, the sixth bond from the end of the fatty acid. The biological effects of the omega−6 fatty acids are largely mediated by their conversion to n-6 eicosanoids that bind to diverse receptors found in every tissue of the body. Eicosadienoic acid has been identified in the human placenta (PMID: 32033212).
Isolated from lipids of Ginkgo biloba (ginkgo)
Eicosadienoic acid is a rare, naturally occurring n-6 polyunsaturated fatty acid found mainly in animal tissues[1][2].
Eicosadienoic acid is a rare, naturally occurring n-6 polyunsaturated fatty acid found mainly in animal tissues[1][2].

同义名列表

57 个代谢物同义名

Eicosa-11,14-dienoic acid, (Z,Z)-isomer; cis,cis-delta11,14-Eicosadienoic acid; (11Z,14Z)-Eicosa-11,14-dienoic acid; (11Z,14Z)-Icosa-11,14-dienoic acid; (11Z,14Z)-11,14-Eicosadienoic acid; cis,cis-Eicosa-11,14-dienoic acid; (11Z,14Z)-11,14-Eicosadienic acid; cis,cis-Δ11,14-eicosadienoic acid; cis,cis-delta11,14-Eicosadienoate; 11-cis,14-cis-Eicosadienoic acid; 11,14-all-cis-Eicosadienoic acid; cis-11,cis-14-Eicosadienoic acid; all-cis-11,14-Eicosadienoic acid; (11Z,14Z)-Eicosa-11,14-dienoate; (11Z,14Z)-Icosa-11,14-dienoate; (11Z,14Z)-11,14-Eicosadienoate; 11,14-trans-Eicosadienoic acid; (Z,Z)-11,14-Eicosadienoic acid; (11Z,14Z)-11,14-Eicosadienate; Dihomo-linoleic acid (20:2n6); delta11,14-Eicosadienoic acid; cis,cis-Eicosa-11,14-dienoate; cis,cis-Δ11,14-eicosadienoate; cis-11,cis-14-Eicosadienoate; (11Z,14Z)-Eicosadienoic acid; 11-cis,14-cis-Eicosadienoate; all-cis-11,14-Eicosadienoate; 11,14-all-cis-Eicosadienoate; Δ11,14-eicosadienoic acid; Dihomo-linoleate (20:2n6); delta11,14-Eicosadienoate; eicosa-11,14-dienoic acid; 11, 14-icosadienoic acid; Homo-gamma-linoleic acid; 11,14-eicosadienoic acid; (11Z,14Z)-Eicosadienoate; (11Z,14Z)-Icosadienoate; 11,14-Icosadienoic acid; N-6 Eicosadienoic acid; Δ11,14-eicosadienoate; Homo-γ-linoleic acid; Bishomolinoleic acid; 11,14-Eicosadienoate; Homo-gamma-linoleate; 11, 14-Icosadienoate; 11,14-Icosadienoate; Eicosadienoic acid; FA(20:2(11Z,14Z)); Icosadienoic acid; Homo-γ-linoleate; Bishomolinoleate; delta11,14-20:2; Dihomolinoleate; Eicosadienoate; FA(20:2n6); 11(Z),14(Z)-Eicosadienoic Acid; icosa-11,14-dienoic acid



数据库引用编号

18 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

1 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(0)

PharmGKB(0)

20 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 7 ACE2, FASN, NAMPT, PLA2G12A, PRKAA2, SIRT1, SREBF1
Endoplasmic reticulum membrane 6 ELOVL2, FADS1, FADS2, FADS3, SCD, SREBF1
Nucleus 7 FABP2, NAMPT, NMNAT1, PARP1, PRKAA2, SIRT1, SREBF1
cytosol 7 FABP2, FASN, NAMPT, PARP1, PRKAA2, SIRT1, SREBF1
dendrite 2 ELOVL2, PRKAA2
nuclear body 2 NMNAT1, PARP1
nucleoplasm 5 NMNAT1, PARP1, PRKAA2, SIRT1, SREBF1
Cell membrane 2 ACE2, TNF
Multi-pass membrane protein 7 ELOVL2, FADS1, FADS2, FADS3, SCD, SREBF1, UCP1
Golgi apparatus membrane 1 SREBF1
cell junction 1 NAMPT
cell surface 2 ACE2, TNF
Golgi apparatus 2 FASN, PRKAA2
Golgi membrane 2 INS, SREBF1
mitochondrial inner membrane 1 UCP1
neuronal cell body 3 ELOVL2, PRKAA2, TNF
Cytoplasm, cytosol 1 PARP1
plasma membrane 4 ACE2, FADS2, FASN, TNF
Membrane 9 ACE2, ELOVL2, FADS1, FADS2, FADS3, FASN, PARP1, PRKAA2, SCD
apical plasma membrane 1 ACE2
axon 1 PRKAA2
extracellular exosome 3 ACE2, FASN, NAMPT
endoplasmic reticulum 3 ELOVL2, SCD, SREBF1
extracellular space 6 ACE2, IL10, IL6, INS, NAMPT, TNF
mitochondrion 4 FADS1, PARP1, SIRT1, UCP1
protein-containing complex 2 PARP1, SREBF1
intracellular membrane-bounded organelle 1 FADS1
chromatin silencing complex 1 SIRT1
Single-pass type I membrane protein 1 ACE2
Secreted 6 ACE2, IL10, IL6, INS, NAMPT, PLA2G12A
extracellular region 6 ACE2, IL10, IL6, INS, PLA2G12A, TNF
transcription regulator complex 1 PARP1
Cell projection, cilium 1 ACE2
external side of plasma membrane 1 TNF
nucleolus 3 PARP1, SCD, SIRT1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Apical cell membrane 1 ACE2
Mitochondrion inner membrane 1 UCP1
heterochromatin 1 SIRT1
Membrane raft 2 ACE2, TNF
Nucleus, PML body 1 SIRT1
PML body 1 SIRT1
nuclear speck 2 NAMPT, PRKAA2
nuclear inner membrane 1 SIRT1
cilium 1 ACE2
chromatin 4 NMNAT1, PARP1, SIRT1, SREBF1
phagocytic cup 1 TNF
Chromosome 1 PARP1
brush border membrane 1 ACE2
Nucleus, nucleolus 1 PARP1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
site of double-strand break 1 PARP1
fibrillar center 1 SIRT1
nuclear envelope 3 PARP1, SIRT1, SREBF1
endosome lumen 1 INS
microvillus 1 FABP2
[Isoform 1]: Endoplasmic reticulum membrane 1 FADS1
Cytoplasmic vesicle membrane 1 SREBF1
Cell projection, dendrite 1 ELOVL2
Melanosome 1 FASN
cytoplasmic stress granule 1 PRKAA2
euchromatin 1 SIRT1
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 ACE2, IL6, INS
endocytic vesicle membrane 1 ACE2
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
ER to Golgi transport vesicle membrane 1 SREBF1
protein-DNA complex 1 PARP1
eNoSc complex 1 SIRT1
rDNA heterochromatin 1 SIRT1
nucleotide-activated protein kinase complex 1 PRKAA2
[Isoform 2]: Endoplasmic reticulum membrane 1 FADS1
Cytoplasmic vesicle, COPII-coated vesicle membrane 1 SREBF1
site of DNA damage 1 PARP1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
interleukin-6 receptor complex 1 IL6
apical cortex 1 FABP2
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
[Sterol regulatory element-binding protein 1]: Endoplasmic reticulum membrane 1 SREBF1
[Processed sterol regulatory element-binding protein 1]: Nucleus 1 SREBF1
[Isoform SREBP-1aDelta]: Nucleus 1 SREBF1
[Isoform SREBP-1cDelta]: Nucleus 1 SREBF1
dendritic tree 1 ELOVL2
glycogen granule 1 FASN
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
[SirtT1 75 kDa fragment]: Cytoplasm 1 SIRT1
[Processed angiotensin-converting enzyme 2]: Secreted 1 ACE2
[Isoform 2]: Apical cell membrane 1 ACE2


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]
  • C Leigh Broadhurst, Walter F Schmidt, Moon S Kim, Julie K Nguyen, Jianwei Qin, Kuanglin Chao, Gary L Bauchan, Daniel R Shelton. Continuous gradient temperature Raman spectroscopy of N-6DPA and DHA from -100 to 20°C. Chemistry and physics of lipids. 2016 10; 200(?):1-10. doi: 10.1016/j.chemphyslip.2016.06.003. [PMID: 27326703]
  • Helen G Gika, Ian D Wilson. Global metabolic profiling for the study of alcohol-related disorders. Bioanalysis. 2014 Jan; 6(1):59-77. doi: 10.4155/bio.13.301. [PMID: 24341495]
  • Jie Fu, Xue-Wei Zhang, Kai Liu, Qing-Shan Li, Li-Rong Zhang, Xian-Hui Yang, Zhi-Ming Zhang, Chang-Zhu Li, Yin Luo, Zhen-Xiang He, Hai-Liang Zhu. Hypolipidemic activity in Sprague-Dawley rats and constituents of a novel natural vegetable oil from Cornus wilsoniana fruits. Journal of food science. 2012 Aug; 77(8):H160-9. doi: 10.1111/j.1750-3841.2012.02786.x. [PMID: 22747885]
  • Saima Amin, Showkat R Mir, Kanchan Kohli, Babar Ali, Mohd Ali. A study of the chemical composition of black cumin oil and its effect on penetration enhancement from transdermal formulations. Natural product research. 2010 Jul; 24(12):1151-7. doi: 10.1080/14786410902940909. [PMID: 20582810]
  • Mukut Sharma, Ellen T McCarthy, D Sudarshan Reddy, Paresh K Patel, Virginia J Savin, Meetha Medhora, John R Falck. 8,9-Epoxyeicosatrienoic acid protects the glomerular filtration barrier. Prostaglandins & other lipid mediators. 2009 Jun; 89(1-2):43-51. doi: 10.1016/j.prostaglandins.2009.04.004. [PMID: 19480064]
  • Woo Jung Park, Kumar S D Kothapalli, Peter Lawrence, Cynthia Tyburczy, J Thomas Brenna. An alternate pathway to long-chain polyunsaturates: the FADS2 gene product Delta8-desaturates 20:2n-6 and 20:3n-3. Journal of lipid research. 2009 Jun; 50(6):1195-202. doi: 10.1194/jlr.m800630-jlr200. [PMID: 19202133]
  • Y Angela Liou, Sheila M Innis. Dietary linoleic acid has no effect on arachidonic acid, but increases n-6 eicosadienoic acid, and lowers dihomo-gamma-linolenic and eicosapentaenoic acid in plasma of adult men. Prostaglandins, leukotrienes, and essential fatty acids. 2009 Apr; 80(4):201-6. doi: 10.1016/j.plefa.2009.02.003. [PMID: 19356914]
  • Wei Zhang, Yin Wang, Chao-Wei Chen, Kuiyi Xing, S Vivekanandan, Marjorie F Lou. The positive feedback role of arachidonic acid in the platelet-derived growth factor-induced signaling in lens epithelial cells. Molecular vision. 2006 Jul; 12(?):821-31. doi: . [PMID: 16902399]
  • Heliana C Salles, Evelyn Cristina F R Volsi, Maurício R Marques, Bibiana M Souza, Lucilene D dos Santos, Cláudio F Tormena, Maria A Mendes, Mario S Palma. The venomous secrets of the web droplets from the viscid spiral of the orb-weaver spider Nephila clavipes (Araneae, Tetragnatidae). Chemistry & biodiversity. 2006 Jul; 3(7):727-41. doi: 10.1002/cbdv.200690075. [PMID: 17193305]
  • D Wang, T J Girard, T P Kasten, R M LaChance, M A Miller-Wideman, R C Durley. Inhibitory activity of unsaturated fatty acids and anacardic acids toward soluble tissue factor-factor VIIa complex. Journal of natural products. 1998 Nov; 61(11):1352-5. doi: 10.1021/np980117p. [PMID: 9834151]
  • M J Steinbeck, J M Robinson, M J Karnovsky. Activation of the neutrophil NADPH-oxidase by free fatty acids requires the ionized carboxyl group and partitioning into membrane lipid. Journal of leukocyte biology. 1991 Apr; 49(4):360-8. doi: 10.1002/jlb.49.4.360. [PMID: 1848271]