Pipecolic acid (BioDeep_00000001407)

 

Secondary id: BioDeep_00000027635, BioDeep_00000229634, BioDeep_00000399925, BioDeep_00000400367, BioDeep_00000405194, BioDeep_00000412684

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


Pipecolic acid, 14C-labeled CPD, (+,-)-isomer

化学式: C6H11NO2 (129.0789746)
中文名称: 2-哌啶甲酸, L-高脯氨酸, L-2-哌啶酸, S-2-哌啶甲酸盐酸盐, 哌啶酸, DL-哌啶甲酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.34%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Pipecolic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/pipecolic_acid (retrieved 2024-11-03) (BioDeep RN: BioDeep_00000001407). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1CCNC(C1)C(=O)O
InChI: InChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)

描述信息

Pipecolic acid is a metabolite of lysine found in human physiological fluids such as urine, plasma and CSF. However, it is uncertain if pipecolic acid originates directly from food intake or from mammalian or intestinal bacterial enzyme metabolism. Recent studies suggest that plasma pipecolic acid, particularly the D-isomer, originates mainly from the catabolism of dietary lysine by intestinal bacteria rather than by direct food intake. In classic Zellweger syndrome (a cerebro-hepato-renal genetic disorder, OMIM 214100) pipecolic acid accumulate in the plasma of the patients. It is known that plasma pipecolic acid levels are also elevated in patients with chronic liver diseases. Pipecolic acid is moderately elevated in patients with pyridoxine-dependent seizures and might therefore be a possible biochemical marker for selecting candidates for pyridoxine therapy (Plecko et al 2000). Pipecolic acid was also elevated in CSF in these vitamin B6-responsive patients (PMID 12705501). Pipecolic acid is found to be associated with adrenoleukodystrophy, infantile Refsum disease, and peroxisomal biogenesis defect, which are also inborn errors of metabolism. Pipecolic acid is a biomarker for the consumption of dried and cooked beans.
Pipecolic acid is a metabolite of lysine found in human physiological fluids such as urine, plasma and CSF. However, it is uncertain if pipecolic acid originates directly from food intake or from mammalian or intestinal bacterial enzyme metabolism. Recent studies suggest that plasma pipecolic acid, particularly the D-isomer, originates mainly from the catabolism of dietary lysine by intestinal bacteria rather than by direct food intake. In classic Zellweger syndrome (a cerebro-hepato-renal genetic disorder, OMIM 214100) pipecolic acid accumulate in the plasma of the patients. It is known that plasma pipecolic acid levels are also elevated in patients with chronic liver diseases. Pipecolic acid is moderately elevated in patients with pyridoxine-dependent seizures and might therefore be a possible biochemical marker for selecting candidates for pyridoxine therapy (Plecko et al 2000). Pipecolic acid was also elevated in CSF in these vitamin B6-responsive patients. (PMID 12705501) [HMDB]. Pipecolic acid is a biomarker for the consumption of dried and cooked beans.
Acquisition and generation of the data is financially supported in part by CREST/JST.
KEIO_ID P048
L-Pipecolic acid (H-HoPro-OH) is a breakdown product of lysine, accumulates in body fluids of infants with generalized genetic peroxisomal disorders, such as Zellweger syndrome, neonatal adrenoleukodystrophy.
L-Pipecolic acid (H-HoPro-OH) is a breakdown product of lysine, accumulates in body fluids of infants with generalized genetic peroxisomal disorders, such as Zellweger syndrome, neonatal adrenoleukodystrophy.
Pipecolic acid, a metabolite of Lysine, is an important precursor of many useful microbial secondary metabolites. Pipecolic acid can be used as a diagnostic marker of Pyridoxine-dependent epilepsy[1][2].
Pipecolic acid, a metabolite of Lysine, is an important precursor of many useful microbial secondary metabolites. Pipecolic acid can be used as a diagnostic marker of Pyridoxine-dependent epilepsy[1][2].

同义名列表

62 个代谢物同义名

Pipecolic acid, 14C-labeled CPD, (+,-)-isomer; Pipecolic acid hydrochloride, (+-)-isomer; Pipecolic acid, ion(1-), (+,-)-isomer; Pipecolic acid, ion(1-), (S)-isomer; (.+/-.)-2-piperidinecarboxylic acid; (S)-(-)-2-Piperidinecarboxylic acid; Pipecolic acid, monopotassium salt; (+/-)-2-piperidinecarboxylic acid; (RS)-2-Piperidinecarboxylic acid; Acide piperidine-carboxylique-2; ()-Piperidine-2-carboxylic acid; DL-2-Piperidinecarboxylic acid; (+/-)-2-piperidinecarboxylate; 2-Piperidinylcarboxylic acid; (RS)-2-Piperidinecarboxylate; Pipecolic acid, (+,-)-isomer; piperidine-2-carboxylic acid; 2-Piperidinecarboxylic acid; DL-2-Piperidinecarboxylate; hexahydro-2-Picolinic acid; Pipecolic acid, (R)-isomer; Pipecolic acid, (S)-isomer; Pipecolic acid, ion (1-); Pipecolic acid free base; .alpha.-pipecolinic acid; Piperidine-2-carboxylate; 2-Piperidinecarboxylate; Hexahydropicolinic acid; hexahydro-2-Picolinate; (+/-)-pipecolinic acid; alpha-Pipecolinic acid; L(-)-Pipecolinic acid; (+,-)-pipecolic acid; (+/-)-pipecolic acid; Hexahydropicolinate; 2-Carboxypiperidine; DL-Pipecolinic acid; Homopipecolic acid; a-Pipecolinic acid; 2-Pipecolinic acid; alpha-Pipecolinate; (+/-)-pipecolinate; DL-Pipecolic acid; Acide pipecolique; Piperolinic acid; (+/-)-pipecolate; Pipecolinic acid; L-Pipecolic acid; Dihydrobaikiane; L-Pipecolicacid; DL-Pipecolinate; DL-Homoproline; a-Pipecolinate; Pipecolic acid; DL-Pipecolate; L-Homoproline; Pipecolinate; Piperolinate; Homoproline; Pipecolate; Pipecolic acid; H-HoPro-OH



数据库引用编号

45 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(1)

BioCyc(0)

PlantCyc(0)

代谢反应

49 个相关的代谢反应过程信息。

Reactome(26)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(22)

PharmGKB(0)

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

  • Liying Luo, Yuying Cai, Yanyun Jiang, Yingying Gong, Chunyang Cai, Dongwei Lai, Xiao Jin, Zhiqiang Guan, Qinghua Qiu. Pipecolic acid mitigates ferroptosis in diabetic retinopathy by regulating GPX4-YAP signaling. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Dec; 169(?):115895. doi: 10.1016/j.biopha.2023.115895. [PMID: 37984309]
  • Alessandro Brambilla, Miriam Lenk, Andrea Ghirardo, Laura Eccleston, Claudia Knappe, Baris Weber, Birgit Lange, Jafargholi Imani, Anton R Schäffner, Jörg-Peter Schnitzler, A Corina Vlot. Pipecolic acid synthesis is required for systemic acquired resistance and plant-to-plant-induced immunity in barley. Journal of experimental botany. 2023 Mar; ?(?):. doi: 10.1093/jxb/erad095. [PMID: 36905226]
  • Lennart Mohnike, Weijie Huang, Brigitte Worbs, Kirstin Feussner, Yuelin Zhang, Ivo Feussner. N-Hydroxy pipecolic acid methyl ester is involved in Arabidopsis immunity. Journal of experimental botany. 2023 01; 74(1):458-471. doi: 10.1093/jxb/erac422. [PMID: 36260503]
  • Feifei Luo, Guirong Tang, Song Hong, Tianyu Gong, Xiu-Fang Xin, Chengshu Wang. Promotion of Arabidopsis immune responses by a rhizosphere fungus via supply of pipecolic acid to plants and selective augment of phytoalexins. Science China. Life sciences. 2022 Nov; ?(?):. doi: 10.1007/s11427-022-2238-8. [PMID: 36449213]
  • Lei Liu, Jia Wu, Minxin Shi, Fengying Wang, Haimin Lu, Jibing Liu, Weiqin Chen, Guanzhen Yu, Dan Liu, Jing Yang, Qin Luo, Yan Ni, Xing Jin, Xiaoxia Jin, Wen-Lian Chen. New Metabolic Alterations and A Predictive Marker Pipecolic Acid in Sera for Esophageal Squamous Cell Carcinoma. Genomics, proteomics & bioinformatics. 2022 Aug; 20(4):670-687. doi: 10.1016/j.gpb.2021.08.016. [PMID: 35351627]
  • Tarun Keswani, Aisha Obeidallah, Edward Nieves, Simone Sidoli, Melissa Fazzari, Terrie Taylor, Karl Seydel, Johanna P Daily. Pipecolic Acid, a Putative Mediator of the Encephalopathy of Cerebral Malaria and the Experimental Model of Cerebral Malaria. The Journal of infectious diseases. 2022 02; 225(4):705-714. doi: 10.1093/infdis/jiab615. [PMID: 34932816]
  • Tamara Treleaven, Madeleine L M Hardy, Michelle Guttman-Jones, Michael B Morris, Margot L Day. In Vitro Fertilisation of Mouse Oocytes in L-Proline and L-Pipecolic Acid Improves Subsequent Development. Cells. 2021 05; 10(6):. doi: 10.3390/cells10061352. [PMID: 34072568]
  • Eric C Holmes, Yun-Chu Chen, Mary Beth Mudgett, Elizabeth S Sattely. Arabidopsis UGT76B1 glycosylates N-hydroxy-pipecolic acid and inactivates systemic acquired resistance in tomato. The Plant cell. 2021 05; 33(3):750-765. doi: 10.1093/plcell/koaa052. [PMID: 33955491]
  • Lennart Mohnike, Dmitrij Rekhter, Weijie Huang, Kirstin Feussner, Hainan Tian, Cornelia Herrfurth, Yuelin Zhang, Ivo Feussner. The glycosyltransferase UGT76B1 modulates N-hydroxy-pipecolic acid homeostasis and plant immunity. The Plant cell. 2021 05; 33(3):735-749. doi: 10.1093/plcell/koaa045. [PMID: 33955489]
  • Hanna Hõrak. How to achieve immune balance and harmony: glycosyltransferase UGT76B1 inactivates N-hydroxy-pipecolic acid to suppress defense responses. The Plant cell. 2021 05; 33(3):453-454. doi: 10.1093/plcell/koaa053. [PMID: 35234939]
  • S Pazarlar, U Sanver, N Cetinkaya. Exogenous pipecolic acid modulates plant defence responses against Podosphaera xanthii and Pseudomonas syringae pv. lachrymans in cucumber (Cucumis sativus L.). Plant biology (Stuttgart, Germany). 2021 May; 23(3):473-484. doi: 10.1111/plb.13243. [PMID: 33547740]
  • Marta Pastorczyk-Szlenkier, Paweł Bednarek. UGT76B1 controls the growth-immunity trade-off during systemic acquired resistance. Molecular plant. 2021 04; 14(4):544-546. doi: 10.1016/j.molp.2021.03.012. [PMID: 33753308]
  • A Corina Vlot. A quest for long-distance signals: the epidermis as central regulator of pipecolic acid-associated systemic acquired resistance. Journal of experimental botany. 2021 03; 72(7):2266-2268. doi: 10.1093/jxb/eraa606. [PMID: 33779751]
  • Jianghua Cai, Adam Jozwiak, Lara Holoidovsky, Michael M Meijler, Sagit Meir, Ilana Rogachev, Asaph Aharoni. Glycosylation of N-hydroxy-pipecolic acid equilibrates between systemic acquired resistance response and plant growth. Molecular plant. 2021 03; 14(3):440-455. doi: 10.1016/j.molp.2020.12.018. [PMID: 33387676]
  • Sandeep Sharma, Babita Choudhary, Sonam Yadav, Avinash Mishra, Vinod K Mishra, Ramesh Chand, Chen Chen, Shree P Pandey. Metabolite profiling identified pipecolic acid as an important component of peanut seed resistance against Aspergillus flavus infection. Journal of hazardous materials. 2021 02; 404(Pt A):124155. doi: 10.1016/j.jhazmat.2020.124155. [PMID: 33049626]
  • Tomiko Kuhara, Tomoyuki Akiyama, Morimasa Ohse, Takayoshi Koike, Jun Shibasaki, Katsumi Imai, ArthurJ L Cooper. Identification of new biomarkers of pyridoxine-dependent epilepsy by GC/MS-based urine metabolomics. Analytical biochemistry. 2020 09; 604(?):113739. doi: 10.1016/j.ab.2020.113739. [PMID: 32339489]
  • Déborah Mathis, Karin Beese, Carmen Rüegg, Barbara Plecko, Martin Hersberger. LC-MS/MS method for the differential diagnosis of treatable early onset inherited metabolic epilepsies. Journal of inherited metabolic disease. 2020 09; 43(5):1102-1111. doi: 10.1002/jimd.12244. [PMID: 32319100]
  • Mar Garcia-Aloy, Marynka Ulaszewska, Pietro Franceschi, Sheila Estruel-Amades, Christoph H Weinert, Alba Tor-Roca, Mireia Urpi-Sarda, Fulvio Mattivi, Cristina Andres-Lacueva. Discovery of Intake Biomarkers of Lentils, Chickpeas, and White Beans by Untargeted LC-MS Metabolomics in Serum and Urine. Molecular nutrition & food research. 2020 07; 64(13):e1901137. doi: 10.1002/mnfr.201901137. [PMID: 32420683]
  • Dan Li, Ruiying Liu, Deepjyoti Singh, Xinyu Yuan, Pradeep Kachroo, Ramesh Raina. JMJ14 encoded H3K4 demethylase modulates immune responses by regulating defence gene expression and pipecolic acid levels. The New phytologist. 2020 03; 225(5):2108-2121. doi: 10.1111/nph.16270. [PMID: 31622519]
  • Denis S Willett, Camila C Filgueiras, Nicole D Benda, Jing Zhang, Kevin E Kenworthy. Sting nematodes modify metabolomic profiles of host plants. Scientific reports. 2020 02; 10(1):2212. doi: 10.1038/s41598-020-59062-8. [PMID: 32042018]
  • Yongsig Kim, Sarah J Gilmour, Lumen Chao, Sunchung Park, Michael F Thomashow. Arabidopsis CAMTA Transcription Factors Regulate Pipecolic Acid Biosynthesis and Priming of Immunity Genes. Molecular plant. 2020 01; 13(1):157-168. doi: 10.1016/j.molp.2019.11.001. [PMID: 31733370]
  • Tiziana Guerra, Silke Schilling, Katharina Hake, Karin Gorzolka, Fabian-Philipp Sylvester, Benjamin Conrads, Bernhard Westermann, Tina Romeis. Calcium-dependent protein kinase 5 links calcium signaling with N-hydroxy-l-pipecolic acid- and SARD1-dependent immune memory in systemic acquired resistance. The New phytologist. 2020 01; 225(1):310-325. doi: 10.1111/nph.16147. [PMID: 31469917]
  • Francisco Oiram Filho, Ebenézer de Oliveira Silva, Mônica Maria de Almeida Lopes, Paulo Riceli Vasconselos Ribeiro, Andréia Hansen Oster, Jhonyson Arruda Carvalho Guedes, Dávila de Souza Zampieri, Patrícia do Nascimento Bordallo, Guilherme Julião Zocolo. Effect of pulsed light on postharvest disease control-related metabolomic variation in melon (Cucumis melo) artificially inoculated with Fusarium pallidoroseum. PloS one. 2020; 15(4):e0220097. doi: 10.1371/journal.pone.0220097. [PMID: 32310943]
  • Cristina Razquin, Miguel Ruiz-Canela, Clary B Clish, Jun Li, Estefania Toledo, Courtney Dennis, Liming Liang, Albert Salas-Huetos, Kerry A Pierce, Marta Guasch-Ferré, Dolores Corella, Emilio Ros, Ramon Estruch, Enrique Gómez-Gracia, Montse Fitó, Jose Lapetra, Dora Romaguera, Angel Alonso-Gómez, Lluis Serra-Majem, Jordi Salas-Salvadó, Frank B Hu, Miguel A Martínez-González. Lysine pathway metabolites and the risk of type 2 diabetes and cardiovascular disease in the PREDIMED study: results from two case-cohort studies. Cardiovascular diabetology. 2019 11; 18(1):151. doi: 10.1186/s12933-019-0958-2. [PMID: 31722714]
  • Marjo Tuomainen, Olli Kärkkäinen, Jukka Leppänen, Seppo Auriola, Marko Lehtonen, Markku J Savolainen, Kjeld Hermansen, Ulf Risérus, Björn Åkesson, Inga Thorsdottir, Marjukka Kolehmainen, Matti Uusitupa, Kaisa Poutanen, Ursula Schwab, Kati Hanhineva. Quantitative assessment of betainized compounds and associations with dietary and metabolic biomarkers in the randomized study of the healthy Nordic diet (SYSDIET). The American journal of clinical nutrition. 2019 11; 110(5):1108-1118. doi: 10.1093/ajcn/nqz179. [PMID: 31504116]
  • Marion Wenig, Andrea Ghirardo, Jennifer H Sales, Elisabeth S Pabst, Heiko H Breitenbach, Felix Antritter, Baris Weber, Birgit Lange, Miriam Lenk, Robin K Cameron, Joerg-Peter Schnitzler, A Corina Vlot. Systemic acquired resistance networks amplify airborne defense cues. Nature communications. 2019 08; 10(1):3813. doi: 10.1038/s41467-019-11798-2. [PMID: 31444353]
  • Jiao Xue, Junjuan Wang, Pan Gong, Minhang Wu, Wenshuang Yang, Shiju Jiang, Ye Wu, Yuwu Jiang, Yuehua Zhang, Tatiana Yuzyuk, Hong Li, Zhixian Yang. Simultaneous quantification of alpha-aminoadipic semialdehyde, piperideine-6-carboxylate, pipecolic acid and alpha-aminoadipic acid in pyridoxine-dependent epilepsy. Scientific reports. 2019 08; 9(1):11371. doi: 10.1038/s41598-019-47882-2. [PMID: 31388081]
  • Christian Dutton, Hanna Hõrak, Christopher Hepworth, Alice Mitchell, Jurriaan Ton, Lee Hunt, Julie E Gray. Bacterial infection systemically suppresses stomatal density. Plant, cell & environment. 2019 08; 42(8):2411-2421. doi: 10.1111/pce.13570. [PMID: 31042812]
  • Min-Zhi Peng, Yan-Na Cai, Yong-Xian Shao, Lu Zhao, Min-Yan Jiang, Yun-Ting Lin, Xi Yin, Hui-Ying Sheng, Li Liu. Simultaneous quantification of 48 plasma amino acids by liquid chromatography-tandem mass spectrometry to investigate urea cycle disorders. Clinica chimica acta; international journal of clinical chemistry. 2019 Aug; 495(?):406-416. doi: 10.1016/j.cca.2019.05.011. [PMID: 31095934]
  • Shu Wang, Kelei Han, Jiejun Peng, Jinping Zhao, Liangliang Jiang, Yuwen Lu, Hongying Zheng, Lin Lin, Jianping Chen, Fei Yan. NbALD1 mediates resistance to turnip mosaic virus by regulating the accumulation of salicylic acid and the ethylene pathway in Nicotiana benthamiana. Molecular plant pathology. 2019 07; 20(7):990-1004. doi: 10.1111/mpp.12808. [PMID: 31012537]
  • Christina Krönauer, Joachim Kilian, Tina Strauß, Mark Stahl, Thomas Lahaye. Cell Death Triggered by the YUCCA-like Bs3 Protein Coincides with Accumulation of Salicylic Acid and Pipecolic Acid But Not of Indole-3-Acetic Acid. Plant physiology. 2019 07; 180(3):1647-1659. doi: 10.1104/pp.18.01576. [PMID: 31068387]
  • Olli Kärkkäinen, Maria A Lankinen, Marilena Vitale, Jenna Jokkala, Jukka Leppänen, Ville Koistinen, Marko Lehtonen, Rosalba Giacco, Natalia Rosa-Sibakov, Valérie Micard, Angela A A Rivellese, Ursula Schwab, Hannu Mykkänen, Matti Uusitupa, Marjukka Kolehmainen, Gabriele Riccardi, Kaisa Poutanen, Seppo Auriola, Kati Hanhineva. Diets rich in whole grains increase betainized compounds associated with glucose metabolism. The American journal of clinical nutrition. 2018 11; 108(5):971-979. doi: 10.1093/ajcn/nqy169. [PMID: 30256894]
  • Yiming Wang, Stefan Schuck, Jingni Wu, Ping Yang, Anne-Christin Döring, Jürgen Zeier, Kenichi Tsuda. A MPK3/6-WRKY33-ALD1-Pipecolic Acid Regulatory Loop Contributes to Systemic Acquired Resistance. The Plant cell. 2018 10; 30(10):2480-2494. doi: 10.1105/tpc.18.00547. [PMID: 30228125]
  • Veronika Boczonadi, Martin S King, Anthony C Smith, Monika Olahova, Boglarka Bansagi, Andreas Roos, Filmon Eyassu, Christoph Borchers, Venkateswaran Ramesh, Hanns Lochmüller, Tuomo Polvikoski, Roger G Whittaker, Angela Pyle, Helen Griffin, Robert W Taylor, Patrick F Chinnery, Alan J Robinson, Edmund R S Kunji, Rita Horvath. Mitochondrial oxodicarboxylate carrier deficiency is associated with mitochondrial DNA depletion and spinal muscular atrophy-like disease. Genetics in medicine : official journal of the American College of Medical Genetics. 2018 10; 20(10):1224-1235. doi: 10.1038/gim.2017.251. [PMID: 29517768]
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