Piperidine (BioDeep_00000003051)

 

Secondary id: BioDeep_00000400257, BioDeep_00000860671

natural product human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


Piperidine ON rasta resin

化学式: C5H11N (85.0891446)
中文名称: 六氢吡啶, 六氢吡啶
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 0.33%

分子结构信息

SMILES: C(C1)CCNC1
InChI: InChI=1/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2

描述信息

Piperidine (Azinane after the Hantzsch Widman nomenclature) is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene units and one nitrogen atom. It is a colorless fuming liquid with an odor described as ammoniacal, pepper-like; the name comes from the genus name Piper, which is the Latin word for pepper. Piperidine is found in barley, black pepper (Piper nigrum). Piperidine has been found to be a microbial metabolite. Piperidine is a flavouring agent and it is also widely used as a building block and chemical reagent in the synthesis of organic compounds, including pharmaceuticals. Piperidine is a widely used secondary amine. It is used to convert ketones to enamines. Enamines derived from piperidine can be used in the Stork enamine alkylation reaction. Piperidine is used as a solvent and as a base. The same is true for certain derivatives: N-formylpiperidine is a polar aprotic solvent with better hydrocarbon solubility than other amide solvents, and 2,2,6,6-tetramethylpiperidine is highly sterically hindered base, useful because of its low nucleophilicity and high solubility in organic solvents.
Acquisition and generation of the data is financially supported in part by CREST/JST.
D002317 - Cardiovascular Agents > D002121 - Calcium Channel Blockers
Present in black pepper (Piper nigrum). Flavouring agent
D000077264 - Calcium-Regulating Hormones and Agents
CONFIDENCE standard compound; INTERNAL_ID 8371
D049990 - Membrane Transport Modulators
KEIO_ID P034

同义名列表

16 个代谢物同义名

Piperidine ON rasta resin; Pentamethyleneamine; Pentamethyleneimine; Pentamethylenimine; hexahydro-Pyridine; Hexahydropyridine; Perhydropyridine; Azacyclohexane; Cyclopentimine; Piperidine; Piperidin; FEMA 2908; Cypentil; Hexazane; Azinane; pip



数据库引用编号

31 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

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)

6 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

  • Kazuki Hashiba, Masamitsu Taguchi, Sachiko Sakamoto, Ayaka Otsu, Yoshiki Maeda, Hirofumi Ebe, Arimichi Okazaki, Hideyoshi Harashima, Yusuke Sato. Overcoming thermostability challenges in mRNA-lipid nanoparticle systems with piperidine-based ionizable lipids. Communications biology. 2024 May; 7(1):556. doi: 10.1038/s42003-024-06235-0. [PMID: 38730092]
  • Lav Singh, Atul K Upadhyay, Pooja Dixit, Arpit Singh, Divyanshu Yadav, Apurv Chhavi, Suraj Konar, Ravi Prakash Srivastava, Shivaraman Pandey, Hari Prasad Devkota, Praveen C Verma, Gauri Saxena. A Review of Chemistry and Pharmacology of Piperidine Alkaloids of Pinus and Related Genera. Current pharmaceutical biotechnology. 2022; 23(9):1132-1141. doi: 10.2174/1389201022666210812123815. [PMID: 34387162]
  • Adedamola A Opalade, Elizabeth N Grotemeyer, Timothy A Jackson. Mimicking Elementary Reactions of Manganese Lipoxygenase Using Mn-hydroxo and Mn-alkylperoxo Complexes. Molecules (Basel, Switzerland). 2021 Nov; 26(23):. doi: 10.3390/molecules26237151. [PMID: 34885729]
  • Botao Cheng, Heng Guo, Haoyang Wang, Qunfei Zhao, Wen Liu. Dissection of the Enzymatic Process for Forming a Central Imidazopiperidine Heterocycle in the Biosynthesis of a Series c Thiopeptide Antibiotic. Journal of the American Chemical Society. 2021 09; 143(34):13790-13797. doi: 10.1021/jacs.1c05956. [PMID: 34405994]
  • Ryan S Nett, Yaereen Dho, Yun-Yee Low, Elizabeth S Sattely. A metabolic regulon reveals early and late acting enzymes in neuroactive Lycopodium alkaloid biosynthesis. Proceedings of the National Academy of Sciences of the United States of America. 2021 06; 118(24):. doi: 10.1073/pnas.2102949118. [PMID: 34112718]
  • Sylvia Richard-Bildstein, Hamed Aissaoui, Julien Pothier, Gabriel Schäfer, Carmela Gnerre, Eleanor Lindenberg, François Lehembre, Laetitia Pouzol, Philippe Guerry. Discovery of the Potent, Selective, Orally Available CXCR7 Antagonist ACT-1004-1239. Journal of medicinal chemistry. 2020 12; 63(24):15864-15882. doi: 10.1021/acs.jmedchem.0c01588. [PMID: 33314938]
  • Elisa Bonandi, Giada Tedesco, Dario Perdicchia, Daniele Passarella. Total Synthesis of (-)-Anaferine: A Further Ramification in a Diversity-Oriented Approach. Molecules (Basel, Switzerland). 2020 Feb; 25(5):. doi: 10.3390/molecules25051057. [PMID: 32120931]
  • Michela Di Napoli, Mario Varcamonti, Adriana Basile, Maurizio Bruno, Filippo Maggi, Anna Zanfardino. Anti-Pseudomonas aeruginosa activity of hemlock (Conium maculatum, Apiaceae) essential oil. Natural product research. 2019 Dec; 33(23):3436-3440. doi: 10.1080/14786419.2018.1477151. [PMID: 29781307]
  • Christopher L Cioffi, Boglarka Racz, Andras Varadi, Emily E Freeman, Michael P Conlon, Ping Chen, Lei Zhu, Douglas B Kitchen, Keith D Barnes, William H Martin, Paul G Pearson, Graham Johnson, William S Blaner, Konstantin Petrukhin. Design, Synthesis, and Preclinical Efficacy of Novel Nonretinoid Antagonists of Retinol-Binding Protein 4 in the Mouse Model of Hepatic Steatosis. Journal of medicinal chemistry. 2019 06; 62(11):5470-5500. doi: 10.1021/acs.jmedchem.9b00352. [PMID: 31079449]
  • Lisa M Broad, Helen E Sanger, Adrian J Mogg, Ellen M Colvin, Ruud Zwart, David A Evans, Francesca Pasqui, Emanuele Sher, Graham N Wishart, Vanessa N Barth, Christian C Felder, Paul J Goldsmith. Identification and pharmacological profile of SPP1, a potent, functionally selective and brain penetrant agonist at muscarinic M1 receptors. British journal of pharmacology. 2019 01; 176(1):110-126. doi: 10.1111/bph.14510. [PMID: 30276808]
  • Rosimeire Borges Moreira Lacerda, Thamires Rodrigues Freitas, Mário Machado Martins, Thaise Lara Teixeira, Cláudio Vieira da Silva, Pamela Aparecida Candido, Ronaldo Junio de Oliveira, Claudio Viegas Júnior, Vanderlan da Silva Bolzani, Amanda Danuello, Marcos Pivatto. Isolation, leishmanicidal evaluation and molecular docking simulations of piperidine alkaloids from Senna spectabilis. Bioorganic & medicinal chemistry. 2018 12; 26(22):5816-5823. doi: 10.1016/j.bmc.2018.10.032. [PMID: 30413343]
  • Hidekazu Tokuhara, Yasuhiro Imaeda, Yoshiyuki Fukase, Koichi Iwanaga, Naohiro Taya, Koji Watanabe, Ray Kanagawa, Keisuke Matsuda, Yumiko Kajimoto, Keiji Kusumoto, Mitsuyo Kondo, Gyorgy Snell, Craig A Behnke, Takanobu Kuroita. Discovery of benzimidazole derivatives as orally active renin inhibitors: Optimization of 3,5-disubstituted piperidine to improve pharmacokinetic profile. Bioorganic & medicinal chemistry. 2018 07; 26(12):3261-3286. doi: 10.1016/j.bmc.2018.04.051. [PMID: 29754833]
  • Qi-Bin Chen, Jie Gao, Guo-An Zou, Xue-Lei Xin, Haji Akber Aisa. Piperidine Alkaloids with Diverse Skeletons from Anacyclus pyrethrum. Journal of natural products. 2018 06; 81(6):1474-1482. doi: 10.1021/acs.jnatprod.8b00239. [PMID: 29775308]
  • Xuebo Zhang, Peng Lei, Tengda Sun, Xiaoyu Jin, Xinling Yang, Yun Ling. Design, Synthesis, and Fungicidal Activity of Novel Thiosemicarbazide Derivatives Containing Piperidine Fragments. Molecules (Basel, Switzerland). 2017 Dec; 22(12):. doi: 10.3390/molecules22122085. [PMID: 29232885]
  • Jian-Cheng Ni, Jian-Ting Shi, Qing-Wei Tan, Qi-Jian Chen. Phenylpropionamides, Piperidine, and Phenolic Derivatives from the Fruit of Ailanthus altissima. Molecules (Basel, Switzerland). 2017 Dec; 22(12):. doi: 10.3390/molecules22122107. [PMID: 29207525]
  • Surya N Meena, Mahesh S Majik, Sanjeev C Ghadi, Santosh G Tilve. Quick Identification of Piperidine Alkaloid from Roots of Grewia nervosa and Their Glucosidase Inhibitory Activity. Chemistry & biodiversity. 2017 Dec; 14(12):. doi: 10.1002/cbdv.201700400. [PMID: 29044865]
  • Ken Yamada, Margaret Brousseau, Wataru Honma, Akiko Iimura, Hidetomo Imase, Yuki Iwaki, Toshio Kawanami, Daniel LaSala, Guiqing Liang, Hironobu Mitani, Kazuhiko Nonomura, Osamu Ohmori, Meihui Pan, Dean F Rigel, Ichiro Umemura, Kayo Yasoshima, Guoming Zhu, Muneto Mogi. Discovery of a Novel Piperidine-Based Inhibitor of Cholesteryl Ester Transfer Protein (CETP) That Retains Activity in Hypertriglyceridemic Plasma. Journal of medicinal chemistry. 2017 10; 60(20):8466-8481. doi: 10.1021/acs.jmedchem.7b00900. [PMID: 29035537]
  • Ting Zhao, Wenling Jin, Hui Pan, Haizhou Li, Yang Zhao, Yang Feng. Rosbin, a synthetic small molecule, induces A549 cells apoptosis through a ROS-mediated pathway. Cell biology international. 2017 Feb; 41(2):221-226. doi: 10.1002/cbin.10714. [PMID: 27981650]
  • Rangxiao Zhuang, Lixin Gao, Xiaoqing Lv, Jianjun Xi, Li Sheng, Yanmei Zhao, Ruoyu He, Xiaobei Hu, Yidan Shao, Xuwang Pan, Shourong Liu, Weiwei Huang, Yubo Zhou, Jia Li, Jiankang Zhang. Exploration of novel piperazine or piperidine constructed non-covalent peptidyl derivatives as proteasome inhibitors. European journal of medicinal chemistry. 2017 Jan; 126(?):1056-1070. doi: 10.1016/j.ejmech.2016.12.034. [PMID: 28027531]
  • Somnuk Bunsupa, Mami Yamazaki, Kazuki Saito. Lysine-derived Alkaloids: Overview and Update on Biosynthesis and Medicinal Applications with Emphasis on Quinolizidine Alkaloids. Mini reviews in medicinal chemistry. 2017; 17(12):1002-1012. doi: 10.2174/1389557516666160506151213. [PMID: 27151143]
  • Victor D A Silva, Carlos Cuevas, Patricia Muñoz, Monica Villa, Ulises Ahumada-Castro, Sandro Huenchuguala, Cleonice C Dos Santos, Fillipe M DE Araujo, Rafael S Ferreira, Vanessa B DA Silva, Juliana H C E Silva, Érica N Soares, Eudes S Velozo, Juan Segura-Aguilar, Silvia L Costa. Autophagy protects against neural cell death induced by piperidine alkaloids present in Prosopis juliflora (Mesquite). Anais da Academia Brasileira de Ciencias. 2017 Jan; 89(1):247-261. doi: 10.1590/0001-3765201720160477. [PMID: 28423083]
  • Suresh Paudel, Yongkai Cao, Shuohan Guo, Byeongkwan An, Kyeong-Man Kim, Seung Hoon Cheon. Design and synthesis of 4-benzylpiperidine carboxamides as dual serotonin and norepinephrine reuptake inhibitors. Bioorganic & medicinal chemistry. 2015 Oct; 23(19):6418-26. doi: 10.1016/j.bmc.2015.08.022. [PMID: 26337019]
  • F Ivy Carroll, Moses G Gichinga, Chad M Kormos, Rangan Maitra, Scott P Runyon, James B Thomas, S Wayne Mascarella, Ann M Decker, Hernán A Navarro. Design, synthesis, and pharmacological evaluation of JDTic analogs to examine the significance of the 3- and 4-methyl substituents. Bioorganic & medicinal chemistry. 2015 Oct; 23(19):6379-88. doi: 10.1016/j.bmc.2015.08.025. [PMID: 26342544]
  • P Patrizia Mangione, Stéphanie Deroo, Stephan Ellmerich, Vittorio Bellotti, Simon Kolstoe, Stephen P Wood, Carol V Robinson, Martin D Smith, Glenys A Tennent, Robert J Broadbridge, Claire E Council, Joanne R Thurston, Victoria A Steadman, Antonio K Vong, Christopher J Swain, Mark B Pepys, Graham W Taylor. Bifunctional crosslinking ligands for transthyretin. Open biology. 2015 Sep; 5(9):150105. doi: 10.1098/rsob.150105. [PMID: 26400472]
  • Philip N Collier, David Messersmith, Arnaud Le Tiran, Upul K Bandarage, Christina Boucher, Jon Come, Kevin M Cottrell, Veronique Damagnez, John D Doran, James P Griffith, Suvarna Khare-Pandit, Elaine B Krueger, Mark W Ledeboer, Brian Ledford, Yusheng Liao, Sudipta Mahajan, Cameron S Moody, Setu Roday, Tiansheng Wang, Jinwang Xu, Alex M Aronov. Discovery of Highly Isoform Selective Thiazolopiperidine Inhibitors of Phosphoinositide 3-Kinase γ. Journal of medicinal chemistry. 2015 Jul; 58(14):5684-8. doi: 10.1021/acs.jmedchem.5b00498. [PMID: 26121481]
  • Guoxin Wang, Longjian Chen, Tongmei Xian, Yujie Liang, Xintao Zhang, Zhen Yang, Ming Luo. Discovery and SAR study of piperidine-based derivatives as novel influenza virus inhibitors. Organic & biomolecular chemistry. 2014 Oct; 12(40):8048-60. doi: 10.1039/c4ob01079e. [PMID: 25184371]
  • Patrick R Gentry, Masaya Kokubo, Thomas M Bridges, Meredith J Noetzel, Hyekyung P Cho, Atin Lamsal, Emery Smith, Peter Chase, Peter S Hodder, Colleen M Niswender, J Scott Daniels, P Jeffrey Conn, Craig W Lindsley, Michael R Wood. Development of a highly potent, novel M5 positive allosteric modulator (PAM) demonstrating CNS exposure: 1-((1H-indazol-5-yl)sulfoneyl)-N-ethyl-N-(2-(trifluoromethyl)benzyl)piperidine-4-carboxamide (ML380). Journal of medicinal chemistry. 2014 Sep; 57(18):7804-10. doi: 10.1021/jm500995y. [PMID: 25147929]
  • Christopher L Cioffi, Nicoleta Dobri, Emily E Freeman, Michael P Conlon, Ping Chen, Douglas G Stafford, Daniel M C Schwarz, Kathy C Golden, Lei Zhu, Douglas B Kitchen, Keith D Barnes, Boglarka Racz, Qiong Qin, Enrique Michelotti, Charles L Cywin, William H Martin, Paul G Pearson, Graham Johnson, Konstantin Petrukhin. Design, synthesis, and evaluation of nonretinoid retinol binding protein 4 antagonists for the potential treatment of atrophic age-related macular degeneration and Stargardt disease. Journal of medicinal chemistry. 2014 Sep; 57(18):7731-57. doi: 10.1021/jm5010013. [PMID: 25210858]
  • Virpi Virjamo, Sirkka Sutinen, Riitta Julkunen-Tiitto. Combined effect of elevated UVB, elevated temperature and fertilization on growth, needle structure and phytochemistry of young Norway spruce (Picea abies) seedlings. Global change biology. 2014 Jul; 20(7):2252-60. doi: 10.1111/gcb.12464. [PMID: 24804850]
  • Carrie K Jones, Douglas J Sheffler, Richard Williams, Sataya B Jadhav, Andrew S Felts, Ryan D Morrison, Colleen M Niswender, J Scott Daniels, P Jeffrey Conn, Craig W Lindsley. Novel GlyT1 inhibitor chemotypes by scaffold hopping. Part 1: development of a potent and CNS penetrant [3.1.0]-based lead. Bioorganic & medicinal chemistry letters. 2014 Feb; 24(4):1067-70. doi: 10.1016/j.bmcl.2014.01.013. [PMID: 24461352]
  • Douglas J Sheffler, Michael T Nedelcovych, Richard Williams, Stephen C Turner, Brittany B Duerk, Megan R Robbins, Sataya B Jadhav, Colleen M Niswender, Carrie K Jones, P Jeffrey Conn, R Nathan Daniels, Craig W Lindsley. Novel GlyT1 inhibitor chemotypes by scaffold hopping. Part 2: development of a [3.3.0]-based series and other piperidine bioisosteres. Bioorganic & medicinal chemistry letters. 2014 02; 24(4):1062-6. doi: 10.1016/j.bmcl.2014.01.011. [PMID: 24462664]
  • Benedict T Green, Stephen T Lee, Kevin D Welch, Kip E Panter. Plant alkaloids that cause developmental defects through the disruption of cholinergic neurotransmission. Birth defects research. Part C, Embryo today : reviews. 2013 Dec; 99(4):235-46. doi: 10.1002/bdrc.21049. [PMID: 24339035]
  • Sandeep B Rajput, S Mohan Karuppayil. Small molecules inhibit growth, viability and ergosterol biosynthesis in Candida albicans. SpringerPlus. 2013 Dec; 2(1):26. doi: 10.1186/2193-1801-2-26. [PMID: 23449869]
  • Yu Tang, Yan Fu, Juan Xiong, Ming Li, Guang-Lei Ma, Guo-Xun Yang, Bang-Guo Wei, Yun Zhao, Hai-Yan Zhang, Jin-Feng Hu. Casuarinines A-J, lycodine-type alkaloids from Lycopodiastrum casuarinoides. Journal of natural products. 2013 Aug; 76(8):1475-84. doi: 10.1021/np4003355. [PMID: 23941108]
  • Benedict T Green, Kevin D Welch, Kip E Panter, Stephen T Lee. Plant toxins that affect nicotinic acetylcholine receptors: a review. Chemical research in toxicology. 2013 Aug; 26(8):1129-38. doi: 10.1021/tx400166f. [PMID: 23848825]
  • Niina Aaltonen, Juha R Savinainen, Casandra Riera Ribas, Jani Rönkkö, Anne Kuusisto, Jani Korhonen, Dina Navia-Paldanius, Jukka Häyrinen, Piia Takabe, Heikki Käsnänen, Tatu Pantsar, Tuomo Laitinen, Marko Lehtonen, Sanna Pasonen-Seppänen, Antti Poso, Tapio Nevalainen, Jarmo T Laitinen. Piperazine and piperidine triazole ureas as ultrapotent and highly selective inhibitors of monoacylglycerol lipase. Chemistry & biology. 2013 Mar; 20(3):379-90. doi: 10.1016/j.chembiol.2013.01.012. [PMID: 23521796]
  • Katarzyna Cieślik-Boczula, Rafał Michał Petrus, Gottfried Köhler, Tadeusz Lis, Aleksander Koll. Interaction of piperidin derivative of Mannich base with DPPC liposomes. The journal of physical chemistry. B. 2013 Mar; 117(10):2938-46. doi: 10.1021/jp311825h. [PMID: 23425432]
  • Yosuke Nakatani, Michiyuki Suzuki, Masaki Tokunaga, Jun Maeda, Miyuki Sakai, Hiroki Ishihara, Takashi Yoshinaga, Osamu Takenaka, Ming-Rong Zhang, Tetsuya Suhara, Makoto Higuchi. A small-animal pharmacokinetic/pharmacodynamic PET study of central serotonin 1A receptor occupancy by a potential therapeutic agent for overactive bladder. PloS one. 2013; 8(9):e75040. doi: 10.1371/journal.pone.0075040. [PMID: 24086433]
  • Shezeng Li, Xixuan Jin, Jian Chen. Effects of piperidine and piperideine alkaloids from the venom of red imported fire ants, Solenopsis invicta Buren, on Pythium ultimum Trow growth in vitro and the application of piperideine alkaloids to control cucumber damping-off in the greenhouse. Pest management science. 2012 Dec; 68(12):1546-52. doi: 10.1002/ps.3337. [PMID: 22685059]
  • Guang Hui Gao, Min Jung Park, Yi Li, Geun Ho Im, Jae-Hoon Kim, Hun Nyun Kim, Jae Won Lee, Pyoung Jeon, Oh Young Bang, Jung Hee Lee, Doo Sung Lee. The use of pH-sensitive positively charged polymeric micelles for protein delivery. Biomaterials. 2012 Dec; 33(35):9157-64. doi: 10.1016/j.biomaterials.2012.09.016. [PMID: 23000386]
  • Li Hong Zhang, Zhi Yong Zheng, Shu-Lian Jiang, Ma-Lin Cui, Li Jiao, Xuan Lin, Wen-Lian Cai, Shao-Qin Lin, Jia-Ming Liu. Coupling technique of self-ordered ring and phosphorimetry for the determination of alkaline phosphatase and diseases prediction. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2012 Nov; 97(?):639-47. doi: 10.1016/j.saa.2012.07.003. [PMID: 22858611]
  • Marek Bajda, Kamil J Kuder, Dorota Lażewska, Katarzyna Kieć-Kononowicz, Anna Więckowska, Michalina Ignasik, Natalia Guzior, Jakub Jończyk, Barbara Malawska. Dual-acting diether derivatives of piperidine and homopiperidine with histamine H(3) receptor antagonistic and anticholinesterase activity. Archiv der Pharmazie. 2012 Aug; 345(8):591-7. doi: 10.1002/ardp.201200018. [PMID: 22549828]
  • Federica Vacondio, Claudia Silva, Lisa Flammini, Vigilio Ballabeni, Elisabetta Barocelli, Marco Mor. Brain pharmacokinetics of non-imidazole biphenyl H3 receptor antagonists: a liquid chromatography/electrospray-mass spectrometry and ex vivo binding study in rats. Chemistry & biodiversity. 2012 Jul; 9(7):1231-9. doi: 10.1002/cbdv.201100242. [PMID: 22782872]
  • Rong Jiang, Xinyi Song, Purva Bali, Anthony Smith, Claudia Ruiz Bayona, Li Lin, Michael D Cameron, Patricia H McDonald, Paul J Kenny, Theodore M Kamenecka. Disubstituted piperidines as potent orexin (hypocretin) receptor antagonists. Bioorganic & medicinal chemistry letters. 2012 Jun; 22(12):3890-4. doi: 10.1016/j.bmcl.2012.04.122. [PMID: 22617492]
  • Benedict T Green, Stephen T Lee, Kip E Panter, David R Brown. Piperidine alkaloids: human and food animal teratogens. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2012 Jun; 50(6):2049-55. doi: 10.1016/j.fct.2012.03.049. [PMID: 22449544]
  • Javier Sastre Toraño, Thierry L Delatte, Henriette Schluepmann, Sjef C M Smeekens, Gerhardus J de Jong, Govert W Somsen. Determination of trehalose-6-phosphate in Arabidopsis thaliana seedlings by hydrophilic-interaction liquid chromatography-mass spectrometry. Analytical and bioanalytical chemistry. 2012 May; 403(5):1353-60. doi: 10.1007/s00216-012-5928-4. [PMID: 22451176]
  • Daniel Cook, Stephen T Lee, James A Pfister, Clint A Stonecipher, Kevin D Welch, Benedict T Green, Kip E Panter. Alkaloid Profiling as an Approach to Differentiate Lupinus garfieldensis, Lupinus sabinianus and Lupinus sericeus. Phytochemical analysis : PCA. 2012 May; 23(3):278-84. doi: 10.1002/pca.1355. [PMID: 21953740]
  • Ishrat Jabeen, Karin Pleban, Uwe Rinner, Peter Chiba, Gerhard F Ecker. Structure-activity relationships, ligand efficiency, and lipophilic efficiency profiles of benzophenone-type inhibitors of the multidrug transporter P-glycoprotein. Journal of medicinal chemistry. 2012 Apr; 55(7):3261-73. doi: 10.1021/jm201705f. [PMID: 22452412]
  • Adlin Afzan, Noor Rain Abdullah, Siti Zaleha Halim, Badrul Amini Rashid, Raja Hazlini Raja Semail, Noordini Abdullah, Ibrahim Jantan, Hussin Muhammad, Zakiah Ismail. Repeated dose 28-days oral toxicity study of Carica papaya L. leaf extract in Sprague Dawley rats. Molecules (Basel, Switzerland). 2012 Apr; 17(4):4326-42. doi: 10.3390/molecules17044326. [PMID: 22491681]
  • Zhuang Miao, Hao Sun, Jennifer Liras, Chandra Prakash. Excretion, metabolism, and pharmacokinetics of 1-(8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl)-4-(ethylamino)piperidine-4-carboxamide, a selective cannabinoid receptor antagonist, in healthy male volunteers. Drug metabolism and disposition: the biological fate of chemicals. 2012 Mar; 40(3):568-78. doi: 10.1124/dmd.111.043273. [PMID: 22187487]
  • A Ulu, Se Appt, C Morisseau, S H Hwang, P D Jones, T E Rose, H Dong, J Lango, J Yang, H J Tsai, C Miyabe, C Fortenbach, M R Adams, B D Hammock. Pharmacokinetics and in vivo potency of soluble epoxide hydrolase inhibitors in cynomolgus monkeys. British journal of pharmacology. 2012 Mar; 165(5):1401-12. doi: 10.1111/j.1476-5381.2011.01641.x. [PMID: 21880036]
  • Patrick M Dansette, Julien Rosi, Gildas Bertho, Daniel Mansuy. Cytochromes P450 catalyze both steps of the major pathway of clopidogrel bioactivation, whereas paraoxonase catalyzes the formation of a minor thiol metabolite isomer. Chemical research in toxicology. 2012 Feb; 25(2):348-56. doi: 10.1021/tx2004085. [PMID: 22103858]
  • Ki Chang Ahn, Takeo Kasagami, Hsing-Ju Tsai, Nils Helge Schebb, Temitope Ogunyoku, Shirley J Gee, Thomas M Young, Bruce D Hammock. An immunoassay to evaluate human/environmental exposure to the antimicrobial triclocarban. Environmental science & technology. 2012 Jan; 46(1):374-81. doi: 10.1021/es202494d. [PMID: 22077920]
  • Somnuk Bunsupa, Mami Yamazaki, Kazuki Saito. Quinolizidine alkaloid biosynthesis: recent advances and future prospects. Frontiers in plant science. 2012; 3(?):239. doi: 10.3389/fpls.2012.00239. [PMID: 23112802]
  • Amad M Al-Azzawi, Ekbal Al-Khateeb, Kulood Al-Sameraei, Alyaa G Al-Juboori. Antibacterial activity and the histopathological study of crude extracts and isolated tecomine from Tecoma stans Bignoniaceae in Iraq. Pharmacognosy research. 2012 Jan; 4(1):37-43. doi: 10.4103/0974-8490.91033. [PMID: 22224060]
  • Weili Sun, Shakeel Modak. Emerging treatment options for the treatment of neuroblastoma: potential role of perifosine. OncoTargets and therapy. 2012; 5(?):21-9. doi: 10.2147/ott.s14578. [PMID: 22419878]
  • Rushika Perera, Catherine Riley, Giorgis Isaac, Amber S Hopf-Jannasch, Ronald J Moore, Karl W Weitz, Ljiljana Pasa-Tolic, Thomas O Metz, Jiri Adamec, Richard J Kuhn. Dengue virus infection perturbs lipid homeostasis in infected mosquito cells. PLoS pathogens. 2012; 8(3):e1002584. doi: 10.1371/journal.ppat.1002584. [PMID: 22457619]
  • Irina I Koleva, Teris A van Beek, Ans E M F Soffers, Birgit Dusemund, Ivonne M C M Rietjens. Alkaloids in the human food chain--natural occurrence and possible adverse effects. Molecular nutrition & food research. 2012 Jan; 56(1):30-52. doi: 10.1002/mnfr.201100165. [PMID: 21823220]
  • Shaopeng Wei, Wenjun Wu, Zhiqin Ji. Synthesis and antibacterial activities of 1-alkyl-3-methacryloyl (acryloyl) of benzimidazolone (thione) derivatives. International journal of molecular sciences. 2012; 13(4):4819-4830. doi: 10.3390/ijms13044819. [PMID: 22606011]
  • Sangeeta Ray Banerjee, Mrudula Pullambhatla, Hassan Shallal, Ala Lisok, Ronnie C Mease, Martin G Pomper. A modular strategy to prepare multivalent inhibitors of prostate-specific membrane antigen (PSMA). Oncotarget. 2011 Dec; 2(12):1244-53. doi: 10.18632/oncotarget.415. [PMID: 22207391]
  • Deepak K Aneja, Poonam Lohan, Sanjiv Arora, Chetan Sharma, Kamal R Aneja, Om Prakash. Synthesis of new pyrazolyl-2, 4-thiazolidinediones as antibacterial and antifungal agents. Organic and medicinal chemistry letters. 2011 Nov; 1(1):15. doi: 10.1186/2191-2858-1-15. [PMID: 22373217]
  • Han Sung Kang, Seok Cheol Lee, Young Seung Park, Young Eun Jeon, Jeong Hwa Lee, So-Youn Jung, In Hae Park, Seok Hoon Jang, Hye Min Park, Chong Woo Yoo, Seok Hee Park, Sang Yun Han, Kwang Pyo Kim, Young Hwan Kim, Jungsil Ro, Hark Kyun Kim. Protein and lipid MALDI profiles classify breast cancers according to the intrinsic subtype. BMC cancer. 2011 Oct; 11(?):465. doi: 10.1186/1471-2407-11-465. [PMID: 22029885]
  • Sylvia Worbs, Kernt Köhler, Diana Pauly, Marc-André Avondet, Martin Schaer, Martin B Dorner, Brigitte G Dorner. Ricinus communis intoxications in human and veterinary medicine-a summary of real cases. Toxins. 2011 10; 3(10):1332-72. doi: 10.3390/toxins3101332. [PMID: 22069699]
  • Kyung Jin Kim, Myoung-Su Lee, Keunae Jo, Jae-Kwan Hwang. Piperidine alkaloids from Piper retrofractum Vahl. protect against high-fat diet-induced obesity by regulating lipid metabolism and activating AMP-activated protein kinase. Biochemical and biophysical research communications. 2011 Jul; 411(1):219-25. doi: 10.1016/j.bbrc.2011.06.153. [PMID: 21741367]
  • Qi Tang, Xiaojun Ma, Changming Mo, Iain W Wilson, Cai Song, Huan Zhao, Yanfang Yang, Wei Fu, Deyou Qiu. An efficient approach to finding Siraitia grosvenorii triterpene biosynthetic genes by RNA-seq and digital gene expression analysis. BMC genomics. 2011 Jul; 12(?):343. doi: 10.1186/1471-2164-12-343. [PMID: 21729270]
  • Geoffrey S Dow, Erin Milner, Ian Bathurst, Jayendra Bhonsle, Diana Caridha, Sean Gardner, Lucia Gerena, Michael Kozar, Charlotte Lanteri, Anne Mannila, William McCalmont, Jay Moon, Kevin D Read, Suzanne Norval, Norma Roncal, David M Shackleford, Jason Sousa, Jessica Steuten, Karen L White, Qiang Zeng, Susan A Charman. Central nervous system exposure of next generation quinoline methanols is reduced relative to mefloquine after intravenous dosing in mice. Malaria journal. 2011 Jun; 10(?):150. doi: 10.1186/1475-2875-10-150. [PMID: 21645370]
  • T L Delatte, H Schluepmann, S C M Smeekens, G J de Jong, G W Somsen. Capillary electrophoresis-mass spectrometry analysis of trehalose-6-phosphate in Arabidopsis thaliana seedlings. Analytical and bioanalytical chemistry. 2011 May; 400(4):1137-44. doi: 10.1007/s00216-011-4837-2. [PMID: 21394451]
  • Shreya S Shah, Gaurang B Shah, Satbeer D Singh, Priyanshi V Gohil, Kajal Chauhan, Khyati A Shah, Mehul Chorawala. Effect of piperine in the regulation of obesity-induced dyslipidemia in high-fat diet rats. Indian journal of pharmacology. 2011 May; 43(3):296-9. doi: 10.4103/0253-7613.81516. [PMID: 21713094]
  • An Choudhary, Ms Kohli, A Kumar, A Joshi. Synthesis of tryptoline-3-carboxylic Acid derivatives a novel antidiabetic agent. Journal of young pharmacists : JYP. 2011 Apr; 3(2):132-7. doi: 10.4103/0975-1483.80302. [PMID: 21731359]
  • Colleen E McGrath, Keri A Tallman, Ned A Porter, Lawrence J Marnett. Structure-activity analysis of diffusible lipid electrophiles associated with phospholipid peroxidation: 4-hydroxynonenal and 4-oxononenal analogues. Chemical research in toxicology. 2011 Mar; 24(3):357-70. doi: 10.1021/tx100323m. [PMID: 21291287]
  • Steffen Fischer, Christian Wiese, Eva Grosse Maestrup, Achim Hiller, Winnie Deuther-Conrad, Matthias Scheunemann, Dirk Schepmann, Jörg Steinbach, Bernhard Wünsch, Peter Brust. Molecular imaging of σ receptors: synthesis and evaluation of the potent σ1 selective radioligand [18F]fluspidine. European journal of nuclear medicine and molecular imaging. 2011 Mar; 38(3):540-51. doi: 10.1007/s00259-010-1658-z. [PMID: 21072511]
  • Poonam Yadav, Nalini V Purohit. Synthesis and biological evaluation of some novel 3,4-disubstituted isocoumarins. Indian journal of pharmaceutical sciences. 2011 Mar; 73(2):171-8. doi: 10.4103/0250-474x.91586. [PMID: 22303060]
  • Susanna Nencetti, Maria R Mazzoni, Gabriella Ortore, Annalina Lapucci, Janette Giuntini, Elisabetta Orlandini, Irene Banti, Elisa Nuti, Antonio Lucacchini, Gino Giannaccini, Armando Rossello. Synthesis, molecular docking and binding studies of selective serotonin transporter inhibitors. European journal of medicinal chemistry. 2011 Mar; 46(3):825-34. doi: 10.1016/j.ejmech.2010.12.018. [PMID: 21272963]
  • Marja Hakala-Yatkin, Esa Tyystjärvi. Inhibition of Photosystem II by the singlet oxygen sensor compounds TEMP and TEMPD. Biochimica et biophysica acta. 2011 Mar; 1807(3):243-50. doi: 10.1016/j.bbabio.2010.11.014. [PMID: 21130069]
  • Hong C Shen, Fa-Xiang Ding, Changyou Zhou, Yusheng Xiong, Andreas Verras, Renee M Chabin, Suoyu Xu, Xinchun Tong, Dan Xie, Michael E Lassman, Urmi R Bhatt, Margarita M Garcia-Calvo, Wayne Geissler, Zhu Shen, Dunlu Chen, Ranabir Sinharoy, Jeffery J Hale, James R Tata, Shirly Pinto, Dong-Ming Shen, Steven L Colletti. Discovery of benzimidazole pyrrolidinyl amides as prolylcarboxypeptidase inhibitors. Bioorganic & medicinal chemistry letters. 2011 Mar; 21(5):1299-305. doi: 10.1016/j.bmcl.2011.01.090. [PMID: 21315588]
  • Marco Miele, Susan Costantini, Giovanni Colonna. Structural and functional similarities between osmotin from Nicotiana tabacum seeds and human adiponectin. PloS one. 2011 Feb; 6(2):e16690. doi: 10.1371/journal.pone.0016690. [PMID: 21311758]
  • Xiaodong Bai, Loren Rivera-Vega, Praveen Mamidala, Pierluigi Bonello, Daniel A Herms, Omprakash Mittapalli. Transcriptomic signatures of ash (Fraxinus spp.) phloem. PloS one. 2011 Jan; 6(1):e16368. doi: 10.1371/journal.pone.0016368. [PMID: 21283712]
  • Mouhssin Oufir, Leslie R Bisset, Stefan R K Hoffmann, Gongda Xue, Stephan Klauser, Bianca Bergamaschi, Alain Gervaix, Jürg Böni, Jörg Schüpbach, Bernd Gutte. Artificial 64-Residue HIV-1 Enhancer-Binding Peptide Is a Potent Inhibitor of Viral Replication in HIV-1-Infected Cells. Advances in virology. 2011; 2011(?):165871. doi: 10.1155/2011/165871. [PMID: 22312334]
  • Pradipto Mukhopadhyay, Malireddy K Reddy, Sneh Lata Singla-Pareek, Sudhir K Sopory. Transcriptional downregulation of rice rpL32 gene under abiotic stress is associated with removal of transcription factors within the promoter region. PloS one. 2011; 6(11):e28058. doi: 10.1371/journal.pone.0028058. [PMID: 22132208]
  • Frank C Mng'ong'o, Joseph J Sambali, Eustachkius Sabas, Justine Rubanga, Jaka Magoma, Alex J Ntamatungiro, Elizabeth L Turner, Daniel Nyogea, Jeroen H J Ensink, Sarah J Moore. Repellent plants provide affordable natural screening to prevent mosquito house entry in tropical rural settings--results from a pilot efficacy study. PloS one. 2011; 6(10):e25927. doi: 10.1371/journal.pone.0025927. [PMID: 22022471]
  • Atsushi Fukushima, Miyako Kusano, Henning Redestig, Masanori Arita, Kazuki Saito. Metabolomic correlation-network modules in Arabidopsis based on a graph-clustering approach. BMC systems biology. 2011 Jan; 5(?):1. doi: 10.1186/1752-0509-5-1. [PMID: 21194489]
  • Sébastien Verne, Barry Jaquish, Rick White, Carol Ritland, Kermit Ritland. Global transcriptome analysis of constitutive resistance to the white pine weevil in spruce. Genome biology and evolution. 2011; 3(?):851-67. doi: 10.1093/gbe/evr069. [PMID: 21852250]
  • Ryan E Pavlovicz, Brandon J Henderson, Andrew B Bonnell, R Thomas Boyd, Dennis B McKay, Chenglong Li. Identification of a negative allosteric site on human α4β2 and α3β4 neuronal nicotinic acetylcholine receptors. PloS one. 2011; 6(9):e24949. doi: 10.1371/journal.pone.0024949. [PMID: 21949802]
  • Beata Jasiewicz, Marzena Wojciechowska-Nowak, Władysław Boczoń, Elżbieta Wyrzykiewicz. Electron ionization mass spectral study of oxo- and thio derivatives of minor tobacco alkaloids. European journal of mass spectrometry (Chichester, England). 2011; 17(3):227-35. doi: 10.1255/ejms.1131. [PMID: 21828414]
  • Binfeng Xia, Desuo Wang, Laura M Fox. Preclinical pharmacokinetics and metabolism of MNP001, a piperidine analog of 3-carbamyl compounds. Biopharmaceutics & drug disposition. 2011 Jan; 32(1):25-37. doi: 10.1002/bdd.736. [PMID: 21162117]
  • Angela M Delucia, David A Six, Ruth E Caughlan, Patricia Gee, Ian Hunt, Joseph S Lam, Charles R Dean. Lipopolysaccharide (LPS) inner-core phosphates are required for complete LPS synthesis and transport to the outer membrane in Pseudomonas aeruginosa PAO1. mBio. 2011; 2(4):. doi: 10.1128/mbio.00142-11. [PMID: 21810964]
  • Joel S Goldberg. Low Molecular Weight Opioid Peptide Esters Could be Developed as a New Class of Analgesics. Perspectives in medicinal chemistry. 2011; 5(?):19-26. doi: 10.4137/pmc.s6803. [PMID: 21863129]
  • Koichiro Aya, Go Suzuki, Keita Suwabe, Tokunori Hobo, Hirokazu Takahashi, Katsuhiro Shiono, Kentaro Yano, Nobuhiro Tsutsumi, Mikio Nakazono, Yoshiaki Nagamura, Makoto Matsuoka, Masao Watanabe. Comprehensive network analysis of anther-expressed genes in rice by the combination of 33 laser microdissection and 143 spatiotemporal microarrays. PloS one. 2011; 6(10):e26162. doi: 10.1371/journal.pone.0026162. [PMID: 22046259]
  • Sung Soo Kim, Etienne Grienenberger, Benjamin Lallemand, Che C Colpitts, Sun Young Kim, Clarice de Azevedo Souza, Pierrette Geoffroy, Dimitri Heintz, Daniel Krahn, Markus Kaiser, Erich Kombrink, Thierry Heitz, Dae-Yeon Suh, Michel Legrand, Carl J Douglas. LAP6/POLYKETIDE SYNTHASE A and LAP5/POLYKETIDE SYNTHASE B encode hydroxyalkyl α-pyrone synthases required for pollen development and sporopollenin biosynthesis in Arabidopsis thaliana. The Plant cell. 2010 Dec; 22(12):4045-66. doi: 10.1105/tpc.110.080028. [PMID: 21193570]
  • Fu-Wei Zhao, Min Luo, Yue-Hu Wang, Ma-Lin Li, Gui-Hua Tang, Chun-Lin Long. A piperidine alkaloid and limonoids from Arisaema decipiens, a traditional antitumor herb used by the Dong people. Archives of pharmacal research. 2010 Nov; 33(11):1735-9. doi: 10.1007/s12272-010-1104-6. [PMID: 21116775]
  • Teagen D Quilichini, Michael C Friedmann, A Lacey Samuels, Carl J Douglas. ATP-binding cassette transporter G26 is required for male fertility and pollen exine formation in Arabidopsis. Plant physiology. 2010 Oct; 154(2):678-90. doi: 10.1104/pp.110.161968. [PMID: 20732973]
  • Brandon J Henderson, Ryan E Pavlovicz, Jerad D Allen, Tatiana F González-Cestari, Crina M Orac, Andrew B Bonnell, Michael X Zhu, R Thomas Boyd, Chenglong Li, Stephen C Bergmeier, Dennis B McKay. Negative allosteric modulators that target human alpha4beta2 neuronal nicotinic receptors. The Journal of pharmacology and experimental therapeutics. 2010 Sep; 334(3):761-74. doi: 10.1124/jpet.110.168211. [PMID: 20551292]
  • Yoshihiro Kojima, Toshiyuki Kimura, Kiyotaka Nakagawa, Akira Asai, Keiji Hasumi, Shinichi Oikawa, Teruo Miyazawa. Effects of mulberry leaf extract rich in 1-deoxynojirimycin on blood lipid profiles in humans. Journal of clinical biochemistry and nutrition. 2010 Sep; 47(2):155-61. doi: 10.3164/jcbn.10-53. [PMID: 20838571]
  • Dasheng Zhang, Wanqi Liang, Changsong Yin, Jie Zong, Fangwei Gu, Dabing Zhang. OsC6, encoding a lipid transfer protein, is required for postmeiotic anther development in rice. Plant physiology. 2010 Sep; 154(1):149-62. doi: 10.1104/pp.110.158865. [PMID: 20610705]
  • Jeffrey G Varnes, Janet M Forst, Tiffany N Hoerter, Christopher R Holmquist, Deidre E Wilkins, Gaochao Tian, Gerald Jonak, Xia Wang, William M Potts, Michael W Wood, Cristóbal Alhambra, Todd A Brugel, Jeffrey S Albert. Identification of N-(2-(azepan-1-yl)-2-phenylethyl)-benzenesulfonamides as novel inhibitors of GlyT1. Bioorganic & medicinal chemistry letters. 2010 Aug; 20(16):4878-81. doi: 10.1016/j.bmcl.2010.06.085. [PMID: 20637614]
  • Guanghou Shui, Xue Li Guan, Pradeep Gopalakrishnan, Yangkui Xue, Joyce Sze Yuin Goh, Hongyuan Yang, Markus R Wenk. Characterization of substrate preference for Slc1p and Cst26p in Saccharomyces cerevisiae using lipidomic approaches and an LPAAT activity assay. PloS one. 2010 Aug; 5(8):e11956. doi: 10.1371/journal.pone.0011956. [PMID: 20694142]
  • Anjanirina Rahantamalala, Philippe Rech, Yves Martinez, Nicole Chaubet-Gigot, Jacqueline Grima-Pettenati, Valérie Pacquit. Coordinated transcriptional regulation of two key genes in the lignin branch pathway--CAD and CCR--is mediated through MYB- binding sites. BMC plant biology. 2010 Jun; 10(?):130. doi: 10.1186/1471-2229-10-130. [PMID: 20584286]
  • Hsing-Ju Tsai, Sung Hee Hwang, Christophe Morisseau, Jun Yang, Paul D Jones, Takeo Kasagami, In-Hae Kim, Bruce D Hammock. Pharmacokinetic screening of soluble epoxide hydrolase inhibitors in dogs. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2010 Jun; 40(3):222-38. doi: 10.1016/j.ejps.2010.03.018. [PMID: 20359531]
  • Hai-Li Liu, Xiao-Yin Huang, Mei-Ling Dong, Guo-Rong Xin, Yue-Wei Guo. Piperidine alkaloids from Chinese mangrove Sonneratia hainanensis. Planta medica. 2010 Jun; 76(9):920-2. doi: 10.1055/s-0029-1240811. [PMID: 20108179]