17-Octadecynoic acid (BioDeep_00000172969)
human metabolite blood metabolite Volatile Flavor Compounds
代谢物信息卡片
化学式: C18H32O2 (280.2402172)
中文名称: 17-十八炔酸, 17十八碳烯酸
谱图信息:
最多检出来源 Homo sapiens(blood) 94.74%
分子结构信息
SMILES: C#CCCCCCCCCCCCCCCCC(=O)O
InChI: InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h1H,3-17H2,(H,19,20)
描述信息
同义名列表
数据库引用编号
6 个数据库交叉引用编号
- ChEBI: CHEBI:142447
- PubChem: 1449
- HMDB: HMDB0244776
- ChEMBL: CHEMBL182310
- chemspider: 1405
- CAS: 34450-18-5
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 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。
文献列表
- Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
Cell reports.
2021 04; 35(4):109040. doi:
10.1016/j.celrep.2021.109040
. [PMID: 33910017] - Xuesong Li, Yan Li, Meijuan Jiang, Wanjie Wu, Sicong He, Congping Chen, Zhongya Qin, Ben Zhong Tang, Ho Yi Mak, Jianan Y Qu. Quantitative Imaging of Lipid Synthesis and Lipolysis Dynamics in Caenorhabditis elegans by Stimulated Raman Scattering Microscopy.
Analytical chemistry.
2019 02; 91(3):2279-2287. doi:
10.1021/acs.analchem.8b04875
. [PMID: 30589537] - Susie J Zoltewicz, Sooyeon Lee, Vinita G Chittoor, Steven M Freeland, Sunitha Rangaraju, David A Zacharias, Lucia Notterpek. The palmitoylation state of PMP22 modulates epithelial cell morphology and migration.
ASN neuro.
2012 Dec; 4(6):409-21. doi:
10.1042/an20120045
. [PMID: 23127255] - Susana Jerez, Liliana Sierra, María Peral de Bruno. 17-Octadecynoic acid improves contractile response to angiotensin II by releasing vasocontrictor prostaglandins.
Prostaglandins & other lipid mediators.
2012 Jan; 97(1-2):36-42. doi:
10.1016/j.prostaglandins.2011.07.008
. [PMID: 21839852] - Tyler Weeks, Iwan Schie, Laura J den Hartigh, John C Rutledge, Thomas Huser. Lipid-cell interactions in human monocytes investigated by doubly-resonant coherent anti-Stokes Raman scattering microscopy.
Journal of biomedical optics.
2011 Feb; 16(2):021117. doi:
10.1117/1.3544585
. [PMID: 21361680] - Mark N Adams, Melinda E Christensen, Yaowu He, Nigel J Waterhouse, John D Hooper. The role of palmitoylation in signalling, cellular trafficking and plasma membrane localization of protease-activated receptor-2.
PloS one.
2011; 6(11):e28018. doi:
10.1371/journal.pone.0028018
. [PMID: 22140500] - Rui-Min Gu, Lei Yang, Yunhong Zhang, Lijun Wang, Shumin Kong, Chengbiao Zhang, Yuanyuan Zhai, Mingxiao Wang, Peng Wu, Liping Liu, Feng Gu, Jiye Zhang, Wen-Hui Wang. CYP-omega-hydroxylation-dependent metabolites of arachidonic acid inhibit the basolateral 10 pS chloride channel in the rat thick ascending limb.
Kidney international.
2009 Oct; 76(8):849-56. doi:
10.1038/ki.2009.287
. [PMID: 19641481] - Brent R Martin, Benjamin F Cravatt. Large-scale profiling of protein palmitoylation in mammalian cells.
Nature methods.
2009 Feb; 6(2):135-8. doi:
10.1038/nmeth.1293
. [PMID: 19137006] - Zhigang Wang, Xiaobo Tang, Yumei Li, Changlian Leu, Lei Guo, Xiaodong Zheng, Daling Zhu. 20-Hydroxyeicosatetraenoic acid inhibits the apoptotic responses in pulmonary artery smooth muscle cells.
European journal of pharmacology.
2008 Jun; 588(1):9-17. doi:
10.1016/j.ejphar.2008.03.045
. [PMID: 18455723] - Susana Jerez, Liliana Sierra, Alfredo Coviello, Maria Peral de Bruno. Endothelial dysfunction and improvement of the angiotensin II-reactivity in hypercholesterolemic rabbits: role of cyclooxygenase metabolites.
European journal of pharmacology.
2008 Feb; 580(1-2):182-9. doi:
10.1016/j.ejphar.2007.10.037
. [PMID: 18053983] - Carolina Kirchheimer, Carlos F Mendez, Andrea Acquier, Susana Nowicki. Role of 20-HETE in D1/D2 dopamine receptor synergism resulting in the inhibition of Na+-K+-ATPase activity in the proximal tubule.
American journal of physiology. Renal physiology.
2007 May; 292(5):F1435-42. doi:
10.1152/ajprenal.00176.2006
. [PMID: 17264308] - Zhong Jian Cheng, Yan-Fen Jiang, Hong Ding, David Severson, Chris R Triggle. Vascular dysfunction in type 2 diabetic TallyHo mice: role for an increase in the contribution of PGH2/TxA2 receptor activation and cytochrome p450 products.
Canadian journal of physiology and pharmacology.
2007 Mar; 85(3-4):404-12. doi:
10.1139/y07-010
. [PMID: 17612649] - Diana Nieves, Juan José Moreno. Hydroxyeicosatetraenoic acids released through the cytochrome P-450 pathway regulate 3T6 fibroblast growth.
Journal of lipid research.
2006 Dec; 47(12):2681-9. doi:
10.1194/jlr.m600212-jlr200
. [PMID: 16980726] - J C Komen, R J A Wanders. Identification of the cytochrome P450 enzymes responsible for the omega-hydroxylation of phytanic acid.
FEBS letters.
2006 Jul; 580(16):3794-8. doi:
10.1016/j.febslet.2006.05.069
. [PMID: 16782090] - Robert-Jan Sanders, Rob Ofman, Fredoen Valianpour, Stephan Kemp, Ronald J A Wanders. Evidence for two enzymatic pathways for omega-oxidation of docosanoic acid in rat liver microsomes.
Journal of lipid research.
2005 May; 46(5):1001-8. doi:
10.1194/jlr.m400510-jlr200
. [PMID: 15716582] - Xuemei Wang, Morley D Hollenberg, Rodger Loutzenhiser. Redundant signaling mechanisms contribute to the vasodilatory response of the afferent arteriole to proteinase-activated receptor-2.
American journal of physiology. Renal physiology.
2005 Jan; 288(1):F65-75. doi:
10.1152/ajprenal.00194.2004
. [PMID: 15328067] - Toshio Nakamura, Takaaki Ishii, Noriyuki Miyata, Kazuo Taniguchi, Yasumitsu Tomishima, Tomokazu Ueki, Masakazu Sato. Design and synthesis of 1-(4-benzoylphenyl)imidazole derivatives as new potent 20-HETE synthase inhibitors.
Bioorganic & medicinal chemistry letters.
2004 Nov; 14(21):5305-8. doi:
10.1016/j.bmcl.2004.08.025
. [PMID: 15454216] - N Caron, A El Hajjam, A-E Declèves, E Joly, J R Falck, R Kramp. Changes in renal haemodynamics induced by indomethacin in the rat involve cytochrome P450 arachidonic acid-dependent epoxygenases.
Clinical and experimental pharmacology & physiology.
2004 Oct; 31(10):683-90. doi:
10.1111/j.0305-1870.2004.04066.x
. [PMID: 15554908] - A Ikari, K Nakajima, Y Suketa, H Harada, K Takagi. Activation of Na+-independent Mg2+ efflux by 20-hydroxyeicosatetraenoic acid in rat renal epithelial cells.
The Japanese journal of physiology.
2004 Aug; 54(4):415-9. doi:
10.2170/jjphysiol.54.415
. [PMID: 15631697] - Jerzy Bełtowski, Andrzej Marciniak, Anna Jamroz-Wiśniewska, Ewelina Borkowska, Grazyna Wójcicka. Bidirectional regulation of renal cortical Na+,K+-ATPase by protein kinase C.
Acta biochimica Polonica.
2004; 51(3):757-72. doi:
045103757
. [PMID: 15448737] - Akira Ikari, Kumiko Nakajima, Yasunobu Suketa, Hitoshi Harada, Kuniaki Takagi. Arachidonic acid-activated Na+-dependent Mg2+ efflux in rat renal epithelial cells.
Biochimica et biophysica acta.
2003 Dec; 1618(1):1-7. doi:
10.1016/j.bbamem.2003.09.011
. [PMID: 14643927] - Xuemei Wang, Greg Trottier, Rodger Loutzenhiser. Determinants of renal afferent arteriolar actions of bradykinin: evidence that multiple pathways mediate responses attributed to EDHF.
American journal of physiology. Renal physiology.
2003 Sep; 285(3):F540-9. doi:
10.1152/ajprenal.00127.2003
. [PMID: 12734100] - Jay S Grider, Cobern E Ott, Brian A Jackson. Dopamine D1 receptor-dependent inhibition of NaCl transport in the rat thick ascending limb: mechanism of action.
European journal of pharmacology.
2003 Jul; 473(2-3):185-90. doi:
10.1016/s0014-2999(03)01965-4
. [PMID: 12892837] - J Bełtowski, A Marciniak, G Wójcicka, D Górny. Nitric oxide decreases renal medullary Na+, K+-ATPase activity through cyclic GMP-protein kinase G dependent mechanism.
Journal of physiology and pharmacology : an official journal of the Polish Physiological Society.
2003 Jun; 54(2):191-210. doi:
. [PMID: 12832721]
- Jerzy Bełtowski, Andrzej Marciniak, Grazyna Wójcicka, Dionizy Górny. Regulation of renal Na(+),K(+)-ATPase and ouabain-sensitive H(+),K(+)-ATPase by the cyclic AMP-protein kinase A signal transduction pathway.
Acta biochimica Polonica.
2003; 50(1):103-14. doi:
035001103
. [PMID: 12673350] - Magdalena Alonso-Galicia, Kristopher G Maier, Andrew S Greene, Allen W Cowley, Richard J Roman. Role of 20-hydroxyeicosatetraenoic acid in the renal and vasoconstrictor actions of angiotensin II.
American journal of physiology. Regulatory, integrative and comparative physiology.
2002 Jul; 283(1):R60-8. doi:
10.1152/ajpregu.00664.2001
. [PMID: 12069931] - L D Alexander, X L Cui, J R Falck, J G Douglas. Arachidonic acid directly activates members of the mitogen-activated protein kinase superfamily in rabbit proximal tubule cells.
Kidney international.
2001 Jun; 59(6):2039-53. doi:
10.1046/j.1523-1755.2001.00718.x
. [PMID: 11380805] - M P Kunert, R J Roman, M Alonso-Galicia, J R Falck, J H Lombard. Cytochrome P-450 omega-hydroxylase: a potential O(2) sensor in rat arterioles and skeletal muscle cells.
American journal of physiology. Heart and circulatory physiology.
2001 Apr; 280(4):H1840-5. doi:
10.1152/ajpheart.2001.280.4.h1840
. [PMID: 11247799] - J Marchetti, F Praddaude, R Rajerison, J L Ader, F Alhenc-Gelas. Bradykinin attenuates the [Ca(2+)](i) response to angiotensin II of renal juxtamedullary efferent arterioles via an EDHF.
British journal of pharmacology.
2001 Feb; 132(3):749-59. doi:
10.1038/sj.bjp.0703851
. [PMID: 11159728] - R Gu, Y Wei, H Jiang, M Balazy, W Wang. Role of 20-HETE in mediating the effect of dietary K intake on the apical K channels in the mTAL.
American journal of physiology. Renal physiology.
2001 Feb; 280(2):F223-30. doi:
10.1152/ajprenal.2001.280.2.f223
. [PMID: 11208597] - E Brand-Schieber, J F Falck, M Schwartzman. Selective inhibition of arachidonic acid epoxidation in vivo.
Journal of physiology and pharmacology : an official journal of the Polish Physiological Society.
2000 Dec; 51(4 Pt 1):655-72. doi:
NULL
. [PMID: 11192939] - A Sánchez-Mendoza, P López-Sánchez, B Vázquez-Cruz, A Rios, S Martínez-Ayala, B Escalante. Angiotensin II modulates ion transport in rat proximal tubules through CYP metabolites.
Biochemical and biophysical research communications.
2000 Jun; 272(2):423-30. doi:
10.1006/bbrc.2000.2807
. [PMID: 10833430] - J M Lasker, W B Chen, I Wolf, B P Bloswick, P D Wilson, P K Powell. Formation of 20-hydroxyeicosatetraenoic acid, a vasoactive and natriuretic eicosanoid, in human kidney. Role of Cyp4F2 and Cyp4A11.
The Journal of biological chemistry.
2000 Feb; 275(6):4118-26. doi:
10.1074/jbc.275.6.4118
. [PMID: 10660572] - I Messer-Létienne, N Bernard, R J Roman, J Sassard, D Benzoni. 20-Hydroxyeicosatetraenoic acid and renal function in Lyon hypertensive rats.
European journal of pharmacology.
1999 Aug; 378(3):291-7. doi:
10.1016/s0014-2999(99)00470-7
. [PMID: 10493105] - O Ito, R J Roman. Role of 20-HETE in elevating chloride transport in the thick ascending limb of Dahl SS/Jr rats.
Hypertension (Dallas, Tex. : 1979).
1999 Jan; 33(1 Pt 2):419-23. doi:
10.1161/01.hyp.33.1.419
. [PMID: 9931140] - R G Evans, K H Day, R J Roman, K H Hopp, W P Anderson. Effects of intrarenal infusion of 17-octadecynoic acid on renal antihypertensive mechanisms in anesthetized rabbits.
American journal of hypertension.
1998 Jul; 11(7):803-12. doi:
10.1016/s0895-7061(98)00045-4
. [PMID: 9683041] - N R Ferreri, B A Escalante, Y Zhao, S J An, J C McGiff. Angiotensin II induces TNF production by the thick ascending limb: functional implications.
The American journal of physiology.
1998 01; 274(1):F148-55. doi:
10.1152/ajprenal.1998.274.1.f148
. [PMID: 9458834] - M A Carroll, M Balazy, D D Huang, S Rybalova, J R Falck, J C McGiff. Cytochrome P450-derived renal HETEs: storage and release.
Kidney international.
1997 Jun; 51(6):1696-702. doi:
10.1038/ki.1997.234
. [PMID: 9186856] - J S Grider, J C Falcone, E L Kilpatrick, C E Ott, B A Jackson. P450 arachidonate metabolites mediate bradykinin-dependent inhibition of NaCl transport in the rat thick ascending limb.
Canadian journal of physiology and pharmacology.
1997 Feb; 75(2):91-6. doi:
. [PMID: 9114929]
- M Lu, Y Zhu, M Balazy, K M Reddy, J R Falck, W Wang. Effect of angiotensin II on the apical K+ channel in the thick ascending limb of the rat kidney.
The Journal of general physiology.
1996 Dec; 108(6):537-47. doi:
10.1085/jgp.108.6.537
. [PMID: 8972391] - C M Macica, Y Yang, S C Hebert, W H Wang. Arachidonic acid inhibits activity of cloned renal K+ channel, ROMK1.
The American journal of physiology.
1996 Sep; 271(3 Pt 2):F588-94. doi:
10.1152/ajprenal.1996.271.3.f588
. [PMID: 8853420] - W H Wang, M Lu, S C Hebert. Cytochrome P-450 metabolites mediate extracellular Ca(2+)-induced inhibition of apical K+ channels in the TAL.
The American journal of physiology.
1996 Jul; 271(1 Pt 1):C103-11. doi:
10.1152/ajpcell.1996.271.1.c103
. [PMID: 8760035] - A P Zou, E E Muirhead, A W Cowley, D L Mattson, J R Falck, J Jiang, R J Roman. Role of changes in renal hemodynamics and P-450 metabolites of arachidonic acid in the reversal of one-kidney, one clip hypertension.
Journal of hypertension.
1995 May; 13(5):557-66. doi:
10.1097/00004872-199505000-00012
. [PMID: 7561014] - J D Imig, A P Zou, P R Ortiz de Montellano, Z Sui, R J Roman. Cytochrome P-450 inhibitors alter afferent arteriolar responses to elevations in pressure.
The American journal of physiology.
1994 May; 266(5 Pt 2):H1879-85. doi:
10.1152/ajpheart.1994.266.5.h1879
. [PMID: 8203587] - A P Zou, J D Imig, M Kaldunski, P R Ortiz de Montellano, Z Sui, R J Roman. Inhibition of renal vascular 20-HETE production impairs autoregulation of renal blood flow.
The American journal of physiology.
1994 Feb; 266(2 Pt 2):F275-82. doi:
10.1152/ajprenal.1994.266.2.f275
. [PMID: 8141328] - A P Zou, Y H Ma, Z H Sui, P R Ortiz de Montellano, J E Clark, B S Masters, R J Roman. Effects of 17-octadecynoic acid, a suicide-substrate inhibitor of cytochrome P450 fatty acid omega-hydroxylase, on renal function in rats.
The Journal of pharmacology and experimental therapeutics.
1994 Jan; 268(1):474-81. doi:
. [PMID: 8301590]
- D Gebremedhin, Y H Ma, J D Imig, D R Harder, R J Roman. Role of cytochrome P-450 in elevating renal vascular tone in spontaneously hypertensive rats.
Journal of vascular research.
1993 Jan; 30(1):53-60. doi:
10.1159/000158975
. [PMID: 8435472]