Pyrrolidine (BioDeep_00000018398)
human metabolite Endogenous
代谢物信息卡片
Pyrrolidine hydrochloride
化学式: C4H9N (71.0734954)
中文名称: 吡咯烷
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1CCNC1
InChI: InChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2
描述信息
Pyrrolidine is found in alcoholic beverages. Pyrrolidine is widely distributed in foodstuffs in trace amts., presumably as bacterial decarboxylation produced of proline. Pyrrolidine is present in bread, milk, cheese, carrots, celery stalks, beer, spirits, coffee, caviar and fatty fish. Pyrrolidine is a flavouring agent.Pyrrolidine is a clear liquid with an unpleasant odor that is ammoniacal, fishy, shellfish-like and seaweed-like. Pyrrolidine is found naturally in the leaves of tobacco and carrot. The pyrrolidine ring structure is present in numerous natural alkaloids such as nicotine and hygrine. It is found in many pharmaceutical drugs such as procyclidine and bepridil. It also forms the basis for the racetam compounds (e.g. piracetam, aniracetam). Pyrrolidine is a pyrrolidine ring is the central structure of the amino acids proline and hydroxyproline. (Wikipedia) Pyrrolidine has been found to be a metabolite in Xenorhabdus (PMID: 19598185).
Prolamins are a group of plant storage proteins having a high proline content and found in the seeds of cereal grains: wheat (gliadin), barley (hordein), rye (secalin), corn (zein) and as a minor protein, avenin in oats. They are characterised by a high glutamine and proline content and are generally soluble only in strong alcohol solutions. Some prolamins, notably gliadin, and similar proteins found in the tribe Triticeae (see Triticeae glutens) may induce coeliac disease in genetically predisposed individuals.
同义名列表
数据库引用编号
12 个数据库交叉引用编号
- ChEBI: CHEBI:33135
- PubChem: 31268
- HMDB: HMDB0031641
- ChEMBL: CHEMBL22830
- Wikipedia: Pyrrolidine
- foodb: FDB007401
- chemspider: 29008
- CAS: 42403-25-8
- CAS: 89014-29-9
- CAS: 123-75-1
- PMhub: MS000007671
- RefMet: Pyrrolidine
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)
4 个相关的物种来源信息
- 3483 - Cannabis sativa: 10.1021/NP50008A001
- 9606 - Homo sapiens: -
- 13216 - Piper nigrum: 10.1271/BBB1961.45.1257
- 29760 - Vitis vinifera: 10.1021/JF00107A012
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
- Hannah M Parks, Maris A Cinelli, Matthew A Bedewitz, Josh M Grabar, Steven M Hurney, Kevin D Walker, A Daniel Jones, Cornelius S Barry. Redirecting tropane alkaloid metabolism reveals pyrrolidine alkaloid diversity in Atropa belladonna.
The New phytologist.
2023 03; 237(5):1810-1825. doi:
10.1111/nph.18651. [PMID: 36451537] - Shinji Nakamura, Masahiro Kamaura, Yuichiro Akao, Natsuko Nakamura, Atsushi Mizukami, Akihiko Goto, Naoki Furuyama, Nobuo Cho, Shizuo Kasai. Discovery of phenylpyrrolidine derivatives as a novel class of retinol binding protein 4 (RBP4) reducers.
Bioorganic & medicinal chemistry.
2022 01; 54(?):116553. doi:
10.1016/j.bmc.2021.116553. [PMID: 34953340] - Hai-Jiao Chen, Hao-Ran Yang, Ying Zhi, Qing-Qiang Yao, Bo Liu. Evaluation of pyrrolidine-based analog of jaspine B as potential SphK1 inhibitors against rheumatoid arthritis.
Bioorganic & medicinal chemistry letters.
2021 02; 34(?):127754. doi:
10.1016/j.bmcl.2020.127754. [PMID: 33347967] - Gongquan Liu, Weiwei Wang, Fangyuan He, Peng Zhang, Ping Xu, Hongzhi Tang. Structural Insights into 6-Hydroxypseudooxynicotine Amine Oxidase from Pseudomonas geniculata N1, the Key Enzyme Involved in Nicotine Degradation.
Applied and environmental microbiology.
2020 09; 86(19):. doi:
10.1128/aem.01559-20. [PMID: 32737127] - Yabing Gan, Guoxing Yin, Ting Yu, Youyu Zhang, Haitao Li, Peng Yin. A novel fluorescent probe for selective imaging of cellular cysteine with large Stokes shift and high quantum yield.
Talanta.
2020 Apr; 210(?):120612. doi:
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Bioorganic & medicinal chemistry.
2020 01; 28(2):115216. doi:
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Molecules (Basel, Switzerland).
2019 Oct; 24(20):. doi:
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Drug and alcohol dependence.
2019 01; 194(?):487-494. doi:
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Journal of enzyme inhibition and medicinal chemistry.
2018 Dec; 33(1):1460-1471. doi:
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Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology.
2018 11; 43(12):2399-2407. doi:
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European journal of medicinal chemistry.
2018 Apr; 150(?):457-478. doi:
10.1016/j.ejmech.2018.02.086. [PMID: 29547833] - Esra Dilek, Sema Caglar, Kübra Erdogan, Bülent Caglar, Onur Sahin. Synthesis and characterization of four novel palladium(II) and platinum(II) complexes with 1-(2-aminoethyl)pyrrolidine, diclofenac and mefenamic acid: In vitro effect of these complexes on human serum paraoxanase1 activity.
Journal of biochemical and molecular toxicology.
2018 Apr; 32(4):e22043. doi:
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2018 02; 92(4):. doi:
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Bioorganic & medicinal chemistry letters.
2017 10; 27(20):4673-4677. doi:
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European journal of medicinal chemistry.
2017 Sep; 138(?):532-542. doi:
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Bioorganic & medicinal chemistry.
2017 09; 25(17):4701-4714. doi:
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Neurotoxicology and teratology.
2017 Sep; 63(?):9-13. doi:
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Journal of medicinal chemistry.
2017 03; 60(6):2562-2572. doi:
10.1021/acs.jmedchem.7b00070. [PMID: 28231433] - Xin Chao Liu, Daowan Lai, Qi Zhi Liu, Ligang Zhou, Qiyong Liu, Zhi Long Liu. Bioactivities of a New Pyrrolidine Alkaloid from the Root Barks of Orixa japonica.
Molecules (Basel, Switzerland).
2016 Dec; 21(12):. doi:
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Parasitology.
2016 09; 143(11):1421-32. doi:
10.1017/s0031182016000937. [PMID: 27230403] - Wenying Li, Weiping Zhao, Xiaohong Liu, Xiaohua Huang, Omar D Lopez, John E Leet, R Marcus Fancher, Van Nguyen, Jason Goodrich, John Easter, Yang Hong, Janet Caceres-Cortes, Shu Y Chang, Li Ma, Makonen Belema, Lawrence G Hamann, Min Gao, Mingshe Zhu, Yue-Zhong Shu, W Griffith Humphreys, Benjamin M Johnson. Biotransformation of Daclatasvir In Vitro and in Nonclinical Species: Formation of the Main Metabolite by Pyrrolidine δ-Oxidation and Rearrangement.
Drug metabolism and disposition: the biological fate of chemicals.
2016 06; 44(6):809-20. doi:
10.1124/dmd.115.068866. [PMID: 27029743] - Hui-Chun Ku, Shih-Yi Lee, Kai-Chien Yang, Yueh-Hsiung Kuo, Ming-Jai Su. Modification of Caffeic Acid with Pyrrolidine Enhances Antioxidant Ability by Activating AKT/HO-1 Pathway in Heart.
PloS one.
2016; 11(2):e0148545. doi:
10.1371/journal.pone.0148545. [PMID: 26845693] - Jutatip Kongpeth, Sakda Jampasa, Piyasak Chaumpluk, Orawon Chailapakul, Tirayut Vilaivan. Immobilization-free electrochemical DNA detection with anthraquinone-labeled pyrrolidinyl peptide nucleic acid probe.
Talanta.
2016; 146(?):318-25. doi:
10.1016/j.talanta.2015.08.059. [PMID: 26695270] - Hao Yu, Hongzhi Tang, Yangyang Li, Ping Xu. Molybdenum-containing nicotine hydroxylase genes in a nicotine degradation pathway that is a variant of the pyridine and pyrrolidine pathways.
Applied and environmental microbiology.
2015 Dec; 81(24):8330-8. doi:
10.1128/aem.02253-15. [PMID: 26407884] - Nahid Shahabadi, Saba Hadidi. Mechanistic and conformational studies on the interaction of a platinum(II) complex containing an antiepileptic drug, levetiracetam, with bovine serum albumin by optical spectroscopic techniques in aqueous solution.
Applied biochemistry and biotechnology.
2015 Feb; 175(4):1843-57. doi:
10.1007/s12010-014-1423-z. [PMID: 25427597] - Audrey Hottin, Daniel W Wright, Gideon J Davies, Jean-Bernard Behr. Exploiting the hydrophobic terrain in fucosidases with aryl-substituted pyrrolidine iminosugars.
Chembiochem : a European journal of chemical biology.
2015 Jan; 16(2):277-83. doi:
10.1002/cbic.201402509. [PMID: 25427942] - Jing-Yu He, Shu Zhu, Katsuko Komatsu. HPLC/UV analysis of polyacetylenes, phenylpropanoid and pyrrolidine alkaloids in medicinally used Codonopsis species.
Phytochemical analysis : PCA.
2014 May; 25(3):213-9. doi:
10.1002/pca.2494. [PMID: 24453136] - Ren-Yi Yan, Hong-Qing Wang, Jie Kang, Ruo-Yun Chen. Pyrrolidine-type iminosugars from leaves of Suregada glomerulata.
Carbohydrate research.
2014 Jan; 384(?):9-12. doi:
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Journal of medicinal chemistry.
2013 Nov; 56(22):9265-74. doi:
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European journal of medicinal chemistry.
2013 May; 63(?):484-500. doi:
10.1016/j.ejmech.2013.02.033. [PMID: 23524160] - Xueqing Zhao, Jörg Pabel, Georg C Höfner, Klaus T Wanner. Synthesis and biological evaluation of 4-hydroxy-4-(4-methoxyphenyl)-substituted proline and pyrrolidin-2-ylacetic acid derivatives as GABA uptake inhibitors.
Bioorganic & medicinal chemistry.
2013 Jan; 21(2):470-84. doi:
10.1016/j.bmc.2012.11.015. [PMID: 23245753] - Masaki Setoguchi, Shin Iimura, Yuuichi Sugimoto, Yoshiyuki Yoneda, Jun Chiba, Toshiyuki Watanabe, Fumihito Muro, Yutaka Iigo, Gensuke Takayama, Mika Yokoyama, Tomoe Taira, Misato Aonuma, Tohru Takashi, Atsushi Nakayama, Nobuo Machinaga. A novel, potent, and orally active VLA-4 antagonist with good aqueous solubility: trans-4-[1-[[2-(5-Fluoro-2-methylphenylamino)-7-fluoro-6-benzoxazolyl]acetyl]-(5S)-[methoxy(methyl)amino]methyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid.
Bioorganic & medicinal chemistry.
2013 Jan; 21(1):42-61. doi:
10.1016/j.bmc.2012.11.003. [PMID: 23218775] - Raman Sharma, Hao Sun, David W Piotrowski, Tim F Ryder, Shawn D Doran, Haiqing Dai, Chandra Prakash. Metabolism, excretion, and pharmacokinetics of ((3,3-difluoropyrrolidin-1-yl)((2S,4S)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidin-2-yl)methanone, a dipeptidyl peptidase inhibitor, in rat, dog and human.
Drug metabolism and disposition: the biological fate of chemicals.
2012 Nov; 40(11):2143-61. doi:
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Bioorganic & medicinal chemistry letters.
2012 Apr; 22(8):2811-7. doi:
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Toxins.
2012 Apr; 4(4):228-43. doi:
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Molecular diversity.
2012 Feb; 16(1):151-6. doi:
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Bioorganic & medicinal chemistry letters.
2012 Jan; 22(1):658-65. doi:
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PloS one.
2012; 7(6):e38456. doi:
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Molecules (Basel, Switzerland).
2011 Dec; 17(1):15-33. doi:
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European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V.
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International journal of antimicrobial agents.
2011 Oct; 38(4):319-24. doi:
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2011 Aug; 100(8):3482-3494. doi:
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BMC complementary and alternative medicine.
2011 Jul; 11(?):56. doi:
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2011 Jul; 39(7):1161-9. doi:
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Journal of hypertension.
2011 Jun; 29(6):1160-6. doi:
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2011 May; 4(?):137. doi:
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Phytochemistry.
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PloS one.
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PLoS pathogens.
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The Plant cell.
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PloS one.
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BMC plant biology.
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Plant physiology.
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2010 Mar; 73(3):331-7. doi:
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BMC pharmacology.
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PloS one.
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European journal of medicinal chemistry.
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Oxidative medicine and cellular longevity.
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PLoS biology.
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Plant molecular biology.
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Biotechnology and applied biochemistry.
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Chemical & pharmaceutical bulletin.
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Phytochemical analysis : PCA.
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Drug metabolism and disposition: the biological fate of chemicals.
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Drug metabolism and disposition: the biological fate of chemicals.
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American journal of physiology. Lung cellular and molecular physiology.
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2008; 59(11):3099-109. doi:
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Bioorganic & medicinal chemistry.
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Phytochemistry.
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Chemical & pharmaceutical bulletin.
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