Dihomo-alpha-linolenic acid (BioDeep_00000002831)
Secondary id: BioDeep_00001872029
human metabolite Endogenous blood metabolite
代谢物信息卡片
化学式: C20H34O2 (306.2559)
中文名称: 11Z,14Z,17Z-二十碳三烯酸, 顺式-11,14,17-二十碳三烯酸
谱图信息:
最多检出来源 Homo sapiens(lipidomics) 34.65%
分子结构信息
SMILES: C(CCCCCCCCC/C=C\C/C=C\C/C=C\CC)(=O)O
InChI: InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10H,2,5,8,11-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-
描述信息
Dihomolinolenic acid, also known as 11,14,17-eicosatrienoic acid or (11z,14z,17z)-eicosa-11,14,17-trienoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, dihomolinolenic acid is considered to be a fatty acid lipid molecule. Dihomolinolenic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Dihomolinolenic acid can be found in evening primrose, which makes dihomolinolenic acid a potential biomarker for the consumption of this food product. Dihomolinolenic acid can be found primarily in blood and feces.
Dihomo-alpha-linolenic acid, also known as 11,14,17-eicosatrienoic acid, is a rare polyunsaturated fatty acid of the omega-3 series. In normal humans, it represents less than 0.25\\% of serum phospholipid fatty acids. However, it is one of the most active essential fatty acids when assayed for the inhibition of fatty acid elongation/desaturation reactions which convert dietary C-18 fatty acids to C-20 eicosanoid precursors. (http://www.caymanchem.com)
同义名列表
60 个代谢物同义名
11,14,17-Eicosatrienoic acid, (Z,Z,Z)-isomer; (11Z,14Z,17Z)-Eicosa-11,14,17-trienoic acid; (11Z,14Z,17Z)-Icosa-11,14,17-trienoic acid; cis,cis,cis-11,14,17-Eicosatrienoic acid; (11Z,14Z,17Z)-Eicosa-11,14,17-trienoate; (11Z,14Z,17Z)-Icosa-11,14,17-trienoate; all-cis-Eicosa-11,14,17-trienoic acid; 11(Z),14(Z),17(Z)-Eicosatrienoic Acid; (Z,Z,Z)-11,14,17-Eicosatrienoic acid; cis,cis,cis-11,14,17-Eicosatrienoate; all-cis-11,14,17-Eicosatrienoic acid; Dihomo-α-linolenic acid (20:3(n-3)); all-cis-Eicosa-11,14,17-triensaeure; all-cis-Eicosa-11,14,17-trienoate; all-cis-11,14,17-Eicosatrienoate; Eicosa-11Z,14Z,17Z-trienoic acid; (Z,Z,Z)-11,14,17-Eicosatrienoate; cis-11,14,17-Eicosatrienoic acid; 11Z,14Z,17Z-eicosatrienoic acid; 11C,14C,17C-Eicosatrienoic acid; eicosa-11,14,17-trienoic acid; 11C,14C,17C-Eicosatriensaeure; Eicosa-11Z,14Z,17Z-trienoate; 11,14,17-eicosatrienoic acid; Bishomo-alpha-linolenic acid; Dihomo-alpha-linolenic acid; 11C,14C,17C-Eicosatrienoate; 11,14,17-Icosatrienoic acid; Homo-alpha-linolenic acid; Bishomo-alpha-linolenate; Bishomo-α-linolenic acid; 11,14,17-Eicosatrienoate; Bishomo-a-linolenic acid; 11,14,17-Icosatrienoate; Dihomo-alpha-linolenate; Dihomo-α-linolenic acid; Dihomo-a-linolenic acid; C20:3, N-3,6,9 all-cis; 20:3, N-3,6,9 all-cis; Homo-α-linolenic acid; FA(20:3(11Z,14Z,17Z)); Dihomo-linolenic acid; Dihomolinolenic acid; Bishomo-α-linolenate; Bishomo-a-linolenate; Eicosatrienoic acid; ETrE(11Z, 14Z, 17Z); Dihomo-α-linolenate; Dihomo-a-linolenate; Icosatrienoic acid; Dihomo-linolenate; Dihomolinolenate; Eicosatrienoate; C20:3n-3,6,9; FA(20:3n3); FA 20:3; ETE; ETA; 11Z,14Z,17Z-Eicosatrienoic Acid; Icosatrienoic acid
数据库引用编号
15 个数据库交叉引用编号
- ChEBI: CHEBI:53460
- KEGG: C16522
- PubChem: 5312529
- PubChem: 3210
- HMDB: HMDB0060039
- Metlin: METLIN35042
- ChEMBL: CHEMBL453991
- LipidMAPS: LMFA01030378
- foodb: FDB006293
- chemspider: 4471954
- CAS: 17046-59-2
- PMhub: MS000006328
- PubChem: 51090851
- NIKKAJI: J323.446K
- KNApSAcK: 53460
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)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
2 个相关的物种来源信息
- 51953 - Elaeis guineensis: 10.1016/S0031-9422(00)85489-8
- 9606 - Homo sapiens: -
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.
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Biochimica et biophysica acta.
2012 Jul; 1821(7):1022-30. doi:
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2011 May; 59(9):4629-36. doi:
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2011 May; 46(5):435-41. doi:
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2011 Jan; 10(?):18. doi:
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PloS one.
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AoB PLANTS.
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2009 Mar; 20(3):513-23. doi:
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Diabetes care.
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2008 Nov; 47(5):635-44. doi:
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Prostaglandins, leukotrienes, and essential fatty acids.
2008 Jul; 79(1-2):47-53. doi:
10.1016/j.plefa.2008.07.005. [PMID: 18757191] - ZhiJian Wang, Yuan Wei, John R Falck, Krishnam Raju Atcha, Wen-Hui Wang. Arachidonic acid inhibits basolateral K channels in the cortical collecting duct via cytochrome P-450 epoxygenase-dependent metabolic pathways.
American journal of physiology. Renal physiology.
2008 Jun; 294(6):F1441-7. doi:
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Animal : an international journal of animal bioscience.
2008 May; 2(5):800-11. doi:
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Zhonghua xin xue guan bing za zhi.
2008 Mar; 36(3):232-5. doi:
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Clinical chemistry.
2008 Feb; 54(2):388-95. doi:
10.1373/clinchem.2007.094623. [PMID: 18089657] - 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] - Christopher Beermann, Michael Möbius, Nadine Winterling, Joachim J Schmitt, Günther Boehm. sn-position determination of phospholipid-linked fatty acids derived from erythrocytes by liquid chromatography electrospray ionization ion-trap mass spectrometry.
Lipids.
2005 Feb; 40(2):211-8. doi:
10.1007/s11745-005-1377-1. [PMID: 15884770] - Eric D Bruder, Ping C Lee, Hershel Raff. Metabolic consequences of hypoxia from birth and dexamethasone treatment in the neonatal rat: comprehensive hepatic lipid and fatty acid profiling.
Endocrinology.
2004 Nov; 145(11):5364-72. doi:
10.1210/en.2004-0582. [PMID: 15271879] - Thomas Colin Michael Fraser, Baoxiu Qi, Salah Elhussein, Sunantha Chatrattanakunchai, Allan Keith Stobart, Colin Michael Lazarus. Expression of the Isochrysis C18-delta9 polyunsaturated fatty acid specific elongase component alters Arabidopsis glycerolipid profiles.
Plant physiology.
2004 Jun; 135(2):859-66. doi:
10.1104/pp.104.038984. [PMID: 15173563] - V L Heyd, A R Eynard. Effects of eicosatrienoic acid (20:3 n-9, Mead's acid) on some promalignant-related properties of three human cancer cell lines.
Prostaglandins & other lipid mediators.
2003 Jul; 71(3-4):177-88. doi:
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The journal of nutrition, health & aging.
2002; 6(6):370-4. doi:
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Prostaglandins & other lipid mediators.
2001 Sep; 66(2):109-20. doi:
10.1016/s0090-6980(01)00152-6. [PMID: 11534547] - A Colquhoun, R I Schumacher. Modifications in mitochondrial metabolism and ultrastructure and their relationship to tumour growth inhibition by gamma-linolenic acid.
Molecular and cellular biochemistry.
2001 Feb; 218(1-2):13-20. doi:
10.1023/a:1007243922393. [PMID: 11330827] - N Nakano, N Shirasaka, M Kurihara, M Takamatsu, T Murakami, H Yoshizumi, R Tsuboi, H Ogawa. Competitive incorporation of arachidonic acid analogs by cultured rat keratinocytes.
Journal of nutritional science and vitaminology.
2001 Feb; 47(1):69-77. doi:
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Journal of natural products.
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