N-Hydroxy-N'-(4-butyl-2-methylphenyl)formamidine (BioDeep_00000174166)
human metabolite blood metabolite
代谢物信息卡片
N-(4-butyl-2-methylphenyl)-N-hydroxymethanimidamide
化学式: C12H18N2O (206.1419)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCCCC1=CC(=C(C=C1)N=CNO)C
InChI: InChI=1S/C12H18N2O/c1-3-4-5-11-6-7-12(10(2)8-11)13-9-14-15/h6-9,15H,3-5H2,1-2H3,(H,13,14)
数据库引用编号
6 个数据库交叉引用编号
- ChEBI: CHEBI:172333
- PubChem: 2727594
- HMDB: HMDB0246170
- ChEMBL: CHEMBL267865
- chemspider: 2009610
- CAS: 339068-25-6
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。
| 亚细胞结构定位 | 关联基因列表 |
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文献列表
- Huiting Jia, Bjoern Brixius, Caleb Bocianoski, Sutapa Ray, David R Koes, Simone Brixius-Anderko. Deciphering the Role of Fatty Acid-Metabolizing CYP4F11 in Lung Cancer and Its Potential As a Drug Target.
Drug metabolism and disposition: the biological fate of chemicals.
2024 Jan; 52(2):69-79. doi:
10.1124/dmd.123.001463. [PMID: 37973374] - Nadja Kampschulte, Tim Berking, Ibrahim E Çelik, Stefan F Kirsch, Nils Helge Schebb. Inhibition of cytochrome P450 monooxygenase-catalyzed oxylipin formation by flavonoids: Evaluation of structure-activity relationship towards CYP4F2-selective inhibitors.
European journal of medicinal chemistry.
2022 Aug; 238(?):114332. doi:
10.1016/j.ejmech.2022.114332. [PMID: 35576701] - Mercedes Muñoz, Elvira López-Oliva, Estéfano Pinilla, Claudia Rodríguez, María Pilar Martínez, Cristina Contreras, Alfonso Gómez, Sara Benedito, Javier Sáenz-Medina, Luis Rivera, Dolores Prieto. Differential contribution of renal cytochrome P450 enzymes to kidney endothelial dysfunction and vascular oxidative stress in obesity.
Biochemical pharmacology.
2022 01; 195(?):114850. doi:
10.1016/j.bcp.2021.114850. [PMID: 34822809] - Zhihong Yang, Rana V Smalling, Yi Huang, Yanchao Jiang, Praveen Kusumanchi, Will Bogaert, Li Wang, Don A Delker, Nicholas J Skill, Sen Han, Ting Zhang, Jing Ma, Nazmul Huda, Suthat Liangpunsakul. The role of SHP/REV-ERBα/CYP4A axis in the pathogenesis of alcohol-associated liver disease.
JCI insight.
2021 08; 6(16):. doi:
10.1172/jci.insight.140687. [PMID: 34423788] - Wenxing Cui, Xun Wu, Yingwu Shi, Wei Guo, Jianing Luo, Haixiao Liu, Longlong Zheng, Yong Du, Ping Wang, Qiang Wang, Dayun Feng, Shunnan Ge, Yan Qu. 20-HETE synthesis inhibition attenuates traumatic brain injury-induced mitochondrial dysfunction and neuronal apoptosis via the SIRT1/PGC-1α pathway: A translational study.
Cell proliferation.
2021 Feb; 54(2):e12964. doi:
10.1111/cpr.12964. [PMID: 33314534] - Zhibo Gai, Ting Gui, Irina Alecu, Museer A Lone, Thorsten Hornemann, Qingfa Chen, Michele Visentin, Christian Hiller, Stephanie Hausler, Gerd A Kullak-Ublick. Farnesoid X receptor activation induces the degradation of hepatotoxic 1-deoxysphingolipids in non-alcoholic fatty liver disease.
Liver international : official journal of the International Association for the Study of the Liver.
2020 04; 40(4):844-859. doi:
10.1111/liv.14340. [PMID: 31883408] - Shumei Ding, Jiajun Huang, Hongmei Qiu, Rongchun Chen, Jie Zhang, Bo Huang, Oumei Cheng, Qingsong Jiang. Effects of PPARs/20-HETE on the renal impairment under diabetic conditions.
Experimental cell research.
2019 09; 382(1):111455. doi:
10.1016/j.yexcr.2019.05.036. [PMID: 31163124] - Shumei Ding, Hongmei Qiu, Jiajun Huang, Rongchun Chen, Jie Zhang, Bo Huang, Xunliang Zou, Oumei Cheng, Qingsong Jiang. Activation of 20-HETE/PPARs involved in reno-therapeutic effect of naringenin on diabetic nephropathy.
Chemico-biological interactions.
2019 Jul; 307(?):116-124. doi:
10.1016/j.cbi.2019.05.004. [PMID: 31063766] - Satoshi Yamaori, Noriyuki Araki, Mio Shionoiri, Kurumi Ikehata, Shinobu Kamijo, Shigeru Ohmori, Kazuhito Watanabe. A Specific Probe Substrate for Evaluation of CYP4A11 Activity in Human Tissue Microsomes and a Highly Selective CYP4A11 Inhibitor: Luciferin-4A and Epalrestat.
The Journal of pharmacology and experimental therapeutics.
2018 09; 366(3):446-457. doi:
10.1124/jpet.118.249557. [PMID: 29976573] - Jessica L Faulkner, Nicole L Plenty, Kedra Wallace, Lorena M Amaral, Mark W Cunningham, Sydney Murphy, Babbette LaMarca. Selective inhibition of 20-hydroxyeicosatetraenoic acid lowers blood pressure in a rat model of preeclampsia.
Prostaglandins & other lipid mediators.
2018 01; 134(?):108-113. doi:
10.1016/j.prostaglandins.2017.09.004. [PMID: 28951260] - Feifei Huang, Yang Liu, Xia Yang, Di Che, Kaifeng Qiu, Bruce D Hammock, Jingfeng Wang, Mong-Heng Wang, Jie Chen, Hui Huang. Shexiang Baoxin pills promotes angiogenesis in myocardial infarction rats via up-regulation of 20-HETE-mediated endothelial progenitor cells mobilization.
Atherosclerosis.
2017 08; 263(?):184-191. doi:
10.1016/j.atherosclerosis.2017.06.012. [PMID: 28646793] - Jin Li, Dao Li, Chaorong Tie, Ji Wu, Qiong Wu, Qixiong Li. Cisplatin-mediated cytotoxicity through inducing CYP4A 11 expression in human renal tubular epithelial cells.
The Journal of toxicological sciences.
2015 Dec; 40(6):895-900. doi:
10.2131/jts.40.895. [PMID: 26558470] - Guangrui Lai, Jingjing Wu, Xiaoliang Liu, Yanyan Zhao. 20-HETE induces hyperglycemia through the cAMP/PKA-PhK-GP pathway.
Molecular endocrinology (Baltimore, Md.).
2012 Nov; 26(11):1907-16. doi:
10.1210/me.2012-1139. [PMID: 22918876] - Abdulaziz M S Alsaad, Beshay N M Zordoky, Ahmed A El-Sherbeni, Ayman O S El-Kadi. Chronic doxorubicin cardiotoxicity modulates cardiac cytochrome P450-mediated arachidonic acid metabolism in rats.
Drug metabolism and disposition: the biological fate of chemicals.
2012 Nov; 40(11):2126-35. doi:
10.1124/dmd.112.046631. [PMID: 22867862] - Maria M Federik Fernandez, Daniel Gonzalez, Jan M Williams, Richard J Roman, Susana Nowicki. Inhibitors of 20-hydroxyeicosatetraenoic acid (20-HETE) formation attenuate the natriuretic effect of dopamine.
European journal of pharmacology.
2012 Jul; 686(1-3):97-103. doi:
10.1016/j.ejphar.2012.04.039. [PMID: 22575524] - Ting Tian, Jin Li, Meng-Ying Wang, Xian-Fei Xie, Qi-Xiong Li. Protective effect of 20-hydroxyeicosatetraenoic acid (20-HETE) on adriamycin-induced toxicity of human renal tubular epithelial cell (HK-2).
European journal of pharmacology.
2012 May; 683(1-3):246-51. doi:
10.1016/j.ejphar.2012.03.001. [PMID: 22421401] - Alexandra Sporková, Libor Kopkan, Sárka Varcabová, Zuzana Husková, Sung Hee Hwang, Bruce D Hammock, John D Imig, Herbert J Kramer, Ludek Cervenka. Role of cytochrome P-450 metabolites in the regulation of renal function and blood pressure in 2-kidney 1-clip hypertensive rats.
American journal of physiology. Regulatory, integrative and comparative physiology.
2011 Jun; 300(6):R1468-75. doi:
10.1152/ajpregu.00215.2010. [PMID: 21411763] - I J Tsai, K D Croft, I B Puddey, L J Beilin, A Barden. 20-Hydroxyeicosatetraenoic acid synthesis is increased in human neutrophils and platelets by angiotensin II and endothelin-1.
American journal of physiology. Heart and circulatory physiology.
2011 Apr; 300(4):H1194-200. doi:
10.1152/ajpheart.00733.2010. [PMID: 21239640] - Komal Sodhi, Cheng-Chia Wu, Jennifer Cheng, Katherine Gotlinger, Kazuyoshi Inoue, Mohan Goli, John R Falck, Nader G Abraham, Michal L Schwartzman. CYP4A2-induced hypertension is 20-hydroxyeicosatetraenoic acid- and angiotensin II-dependent.
Hypertension (Dallas, Tex. : 1979).
2010 Nov; 56(5):871-8. doi:
10.1161/hypertensionaha.110.154559. [PMID: 20837888] - Mariko Nakano, Edward J Kelly, Allan E Rettie. Expression and characterization of CYP4V2 as a fatty acid omega-hydroxylase.
Drug metabolism and disposition: the biological fate of chemicals.
2009 Nov; 37(11):2119-22. doi:
10.1124/dmd.109.028530. [PMID: 19661213] - Anna Alexanian, Victoriya A Rufanova, Bradley Miller, Averia Flasch, Richard J Roman, Andrey Sorokin. Down-regulation of 20-HETE synthesis and signaling inhibits renal adenocarcinoma cell proliferation and tumor growth.
Anticancer research.
2009 Oct; 29(10):3819-24. doi:
NULL. [PMID: 19846914] - Yi Zhang, Jason H Y Wu, Janine J Vickers, Sharon L H Ong, Suzanna E L Temple, Trevor A Mori, Kevin D Croft, Judith A Whitworth. The role of 20-hydroxyeicosatetraenoic acid in adrenocorticotrophic hormone and dexamethasone-induced hypertension.
Journal of hypertension.
2009 Aug; 27(8):1609-16. doi:
10.1097/hjh.0b013e32832cc56c. [PMID: 19458537] - Suyi Cao, Liang-Chao Wang, Herman Kwansa, Richard J Roman, David R Harder, Raymond C Koehler. Endothelin rather than 20-HETE contributes to loss of pial arteriolar dilation during focal cerebral ischemia with and without polymeric hemoglobin transfusion.
American journal of physiology. Regulatory, integrative and comparative physiology.
2009 May; 296(5):R1412-8. doi:
10.1152/ajpregu.00003.2009. [PMID: 19261918] - O Tornavaca, G Pascual, M L Barreiro, M T Grande, A Carretero, M Riera, E Garcia-Arumi, B Bardaji, M González-Núñez, M A Montero, J M López-Novoa, A Meseguer. Kidney androgen-regulated protein transgenic mice show hypertension and renal alterations mediated by oxidative stress.
Circulation.
2009 Apr; 119(14):1908-17. doi:
10.1161/circulationaha.108.808543. [PMID: 19332469] - Frank Park, William E Sweeney, Guangfu Jia, Talha Akbulut, Benjamin Mueller, J Russell Falck, Saritha Birudaraju, Richard J Roman, Ellis D Avner. Chronic blockade of 20-HETE synthesis reduces polycystic kidney disease in an orthologous rat model of ARPKD.
American journal of physiology. Renal physiology.
2009 Mar; 296(3):F575-82. doi:
10.1152/ajprenal.90705.2008. [PMID: 19129252] - M H M Yousif, I F Benter, K M J Dunn, A J Dahly-Vernon, S Akhtar, R J Roman. Role of 20-hydroxyeicosatetraenoic acid in altering vascular reactivity in diabetes.
Autonomic & autacoid pharmacology.
2009 Jan; 29(1-2):1-12. doi:
10.1111/j.1474-8673.2009.00426.x. [PMID: 19302551] - Frank Park, William E Sweeney, Guangfu Jia, Richard J Roman, Ellis D Avner. 20-HETE mediates proliferation of renal epithelial cells in polycystic kidney disease.
Journal of the American Society of Nephrology : JASN.
2008 Oct; 19(10):1929-39. doi:
10.1681/asn.2007070771. [PMID: 18596124] - Zhaohui Gao, Satoshi Koba, Lawrence Sinoway, Jianhua Li. 20-HETE increases renal sympathetic nerve activity via activation of chemically and mechanically sensitive muscle afferents.
The Journal of physiology.
2008 May; 586(10):2581-91. doi:
10.1113/jphysiol.2008.150730. [PMID: 18372304] - Jan Michael Williams, Mukut Sharma, Siddam Anjaiahh, John R Falck, Richard J Roman. Role of endogenous CYP450 metabolites of arachidonic acid in maintaining the glomerular protein permeability barrier.
American journal of physiology. Renal physiology.
2007 Aug; 293(2):F501-5. doi:
10.1152/ajprenal.00131.2007. [PMID: 17507602] - Jan M Williams, Albert Sarkis, Bernardo Lopez, Robert P Ryan, Averia K Flasch, Richard J Roman. Elevations in renal interstitial hydrostatic pressure and 20-hydroxyeicosatetraenoic acid contribute to pressure natriuresis.
Hypertension (Dallas, Tex. : 1979).
2007 Mar; 49(3):687-94. doi:
10.1161/01.hyp.0000255753.89363.47. [PMID: 17210834] - Samuel M Poloyac, Yuqing Zhang, Robert R Bies, Patrick M Kochanek, Steven H Graham. Protective effect of the 20-HETE inhibitor HET0016 on brain damage after temporary focal ischemia.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism.
2006 Dec; 26(12):1551-61. doi:
10.1038/sj.jcbfm.9600309. [PMID: 16570075] - M Kuczeriszka, B Badzyńska, E Kompanowska-Jezierska. Cytochrome P-450 monooxygenases in control of renal haemodynamics and arterial pressure in anaesthetized rats.
Journal of physiology and pharmacology : an official journal of the Polish Physiological Society.
2006 Nov; 57 Suppl 11(?):179-85. doi:
. [PMID: 17244949] - E Joly, R Seqqat, B Flamion, N Caron, A Michel, J D Imig, R Kramp. Increased renal vascular reactivity to ANG II after unilateral nephrectomy in the rat involves 20-HETE.
American journal of physiology. Regulatory, integrative and comparative physiology.
2006 Oct; 291(4):R977-86. doi:
10.1152/ajpregu.00401.2005. [PMID: 16675634] - Ahmad Blanton, Rami Nsaif, Hantz Hercule, Adebayo Oyekan. Nitric oxide/cytochrome P450 interactions in cyclosporin A-induced effects in the rat.
Journal of hypertension.
2006 Sep; 24(9):1865-72. doi:
10.1097/01.hjh.0000242412.88653.f2. [PMID: 16915037] - 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] - Kimberly M Hoagland, Averia K Flasch, Richard J Roman. Inhibitors of 20-HETE formation promote salt-sensitive hypertension in rats.
Hypertension (Dallas, Tex. : 1979).
2003 Oct; 42(4):669-73. doi:
10.1161/01.hyp.0000084634.97353.1a. [PMID: 12874093] - M Sato, T Ishii, Y Kobayashi-Matsunaga, H Amada, K Taniguchi, N Miyata, K Kameo. Discovery of a N'-hydroxyphenylformamidine derivative HET0016 as a potent and selective 20-HETE synthase inhibitor.
Bioorganic & medicinal chemistry letters.
2001 Dec; 11(23):2993-5. doi:
10.1016/s0960-894x(01)00614-x. [PMID: 11714595] - B López, C Moreno, M G Salom, R J Roman, F J Fenoy. Role of guanylyl cyclase and cytochrome P-450 on renal response to nitric oxide.
American journal of physiology. Renal physiology.
2001 Sep; 281(3):F420-7. doi:
10.1152/ajprenal.2001.281.3.f420. [PMID: 11502591] - N Miyata, K Taniguchi, T Seki, T Ishimoto, M Sato-Watanabe, Y Yasuda, M Doi, S Kametani, Y Tomishima, T Ueki, M Sato, K Kameo. HET0016, a potent and selective inhibitor of 20-HETE synthesizing enzyme.
British journal of pharmacology.
2001 Jun; 133(3):325-9. doi:
10.1038/sj.bjp.0704101. [PMID: 11375247] - 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.
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