Picolinic acid (BioDeep_00000001406)

 

Secondary id: BioDeep_00000405522

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019 natural product


代谢物信息卡片


5-Aminopyridine-2-carboxylic acid

化学式: C6H5NO2 (123.032)
中文名称: 2-吡啶甲酸, 吡啶甲酸
谱图信息: 最多检出来源 Homo sapiens(blood) 23.03%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Picolinic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/picolinic_acid (retrieved 2024-12-23) (BioDeep RN: BioDeep_00000001406). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1=CC=NC(=C1)C(=O)O
InChI: InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)

描述信息

Picolinic acid is a metabolite of the tryptophan catabolism. Picolinic acid is produced under inflammatory conditions and a costimulus with interferon-gamma (IFNgamma) of macrophage (Mphi) effector functions, is a selective inducer of the Mphi inflammatory protein-1alpha (MIP-1alpha) and -1beta (MIPs), two chemokines/cytokines involved in the elicitation of the inflammatory reactions and in the development of the Th1 responses. IFNgamma and picolinic acid have reciprocal effects on the production of MIPs chemokines and the expression of their receptor. The concerted action of IFNgamma and picolinic acid on MIP-1alpha/beta chemokine/receptor system is likely to be of pathophysiological significance and to represent an important regulatory mechanism for leukocyte recruitment and distribution into damaged tissues during inflammatory responses. Picolinic acid has an effect on the production of L-arginine-derived reactive nitrogen intermediates in macrophages, by augmenting IFN-gamma-induced NO2- production, and acts synergistically with IFN-gamma in activating macrophages. Children with acrodermatitis enteropathica (AE) are treated with oral zinc dipicolinate (zinc-PA). The concentration of picolinic acid in the plasma of asymptomatic children with AE was significantly less than that of normal children. However, oral treatment with PA alone is ineffective. The results support the hypothesis that the genetic defect in AE is in the tryptophan pathway, although the role of PA in zinc metabolism remains to be defined. (PMID:15206716, 8473748, 1701787, 6694049).
Picolinic acid is a metabolite of the tryptophan catabolism. Picolinic acid is produced under inflammatory conditions and a costimulus with interferon-gamma (IFNgamma) of macrophage (Mphi) effector functions, is a selective inducer of the Mphi inflammatory protein-1alpha (MIP-1alpha) and -1beta (MIPs), two chemokines/cytokines involved in the elicitation of the inflammatory reactions and in the development of the Th1 responses. IFNgamma and picolinic acid have reciprocal effects on the production of MIPs chemokines and the expression of their receptor. The concerted action of IFNgamma and picolinic acid on MIP-1alpha/beta chemokine/receptor system is likely to be of pathophysiological significance and to represent an important regulatory mechanism for leukocyte recruitment and distribution into damaged tissues during inflammatory responses. Picolinic acid has an effect on the production of L-arginine-derived reactive nitrogen intermediates in macrophages, by augmenting IFN-gamma-induced NO2- production, and acts synergistically with IFN-gamma in activating macrophages.
D064449 - Sequestering Agents > D002614 - Chelating Agents > D007502 - Iron Chelating Agents
[Raw Data] CBA16_Picolinic-acid_pos_10eV_1-8_01_816.txt
[Raw Data] CBA16_Picolinic-acid_pos_20eV_1-8_01_817.txt
KEIO_ID P045
Picolinic acid (PCL 016) is a topical antiviral agent, which inhibits adenovirus replication in rabbits.

同义名列表

49 个代谢物同义名

5-Aminopyridine-2-carboxylic acid; 5-amino-2-Pyridinecarboxylic acid; Calcium dipicolinate trihydrate; Phenyl-(2-pyridyl)acetonitrile; alpha-Pyridinecarboxylic acid; Picolinic acid, hydrochloride; Pyridinecarboxylic acid-(2); 6-Methoxy-pyridin-3-ylamine; Picolinic acid, sodium salt; PYRIDINE-2-carboxylIC ACID; 2-Pyridine carboxylic acid; a-Pyridinecarboxylic acid; O-Pyridinecarboxylic acid; 2-Pyridinecarboxylic acid; Α-pyridinecarboxylic acid; 4,5-Dehydropipecolic acid; 2-Methoxy-5-aminopyridine; alpha-Pyridinecarboxylate; 5-amino-2-Methoxypyridine; 5-Amino-2-fluoropyridine; Pyridine-carboxylique-2; PYRIDINE-2-carboxylate; 5-Aminopicolinic acid; O-Pyridinecarboxylate; 2-Pyridinecarboxylate; a-Pyridinecarboxylate; Α-pyridinecarboxylate; Iron(III) picolinate; alpha-Picolinic acid; Chromium Picolinate; 2-Carboxypyridine; alpha-Picolinate; 2-Picolinic acid; a-Picolinic acid; Α-picolinic acid; Acide picolique; Zinc Picolinate; picolinic acid; Α-picolinate; 2-Picolinate; a-Picolinate; Picolinate; L-Baikiain; 2-Picolate; PLA; Picolinic acid; PCL 016; Picolinic acid; Picolinic acid



数据库引用编号

30 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

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(2)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

43 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
Cytoplasm 9 ACMSD, ALB, CHAT, CYP1A1, DBH, IDO1, MTOR, NOS2, PPARG
Peripheral membrane protein 2 CYP1A1, MTOR
Endosome membrane 1 TF
Endoplasmic reticulum membrane 2 CYP1A1, MTOR
Nucleus 5 ALB, CHAT, MTOR, NOS2, PPARG
cytosol 10 ACMSD, ALB, CHAT, IDO1, KMO, MTOR, NOS2, NRK, PPARG, TDO2
dendrite 1 MTOR
phagocytic vesicle 1 MTOR
centrosome 1 ALB
nucleoplasm 3 MTOR, NOS2, PPARG
RNA polymerase II transcription regulator complex 1 PPARG
Cell membrane 1 TNF
Cytoplasmic side 1 MTOR
Multi-pass membrane protein 1 KMO
Golgi apparatus membrane 1 MTOR
Synapse 2 CHAT, DBH
cell surface 2 TF, TNF
Golgi apparatus 1 ALB
Golgi membrane 1 MTOR
lysosomal membrane 1 MTOR
mitochondrial inner membrane 1 CYP1A1
neuronal cell body 1 TNF
Cytoplasm, cytosol 2 IDO1, NOS2
Lysosome 1 MTOR
plasma membrane 4 IFNLR1, NOS2, TF, TNF
Membrane 6 ACMSD, DBH, IFNLR1, KMO, MTOR, NRK
apical plasma membrane 1 TF
extracellular exosome 2 ALB, TF
Lysosome membrane 1 MTOR
endoplasmic reticulum 2 ALB, DBH
extracellular space 10 ALB, CRP, DBH, IL10, IL2, IL4, IL6, KMO, TF, TNF
perinuclear region of cytoplasm 3 NOS2, PPARG, TF
mitochondrion 2 CYP1A1, KMO
protein-containing complex 1 ALB
intracellular membrane-bounded organelle 3 CYP1A1, DBH, PPARG
Microsome membrane 2 CYP1A1, MTOR
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 1 IFNLR1
Secreted 8 ALB, CRP, DBH, IL10, IL2, IL4, IL6, TF
extracellular region 9 ALB, CRP, DBH, IL10, IL2, IL4, IL6, TF, TNF
Mitochondrion outer membrane 2 KMO, MTOR
mitochondrial outer membrane 2 KMO, MTOR
basal part of cell 1 TF
anchoring junction 1 ALB
centriolar satellite 1 DBH
external side of plasma membrane 1 TNF
cytoplasmic vesicle 1 TF
Cytoplasm, P-body 1 NOS2
P-body 1 NOS2
Early endosome 1 TF
clathrin-coated pit 1 TF
recycling endosome 2 TF, TNF
Single-pass type II membrane protein 2 DBH, TNF
vesicle 1 TF
Cytoplasm, perinuclear region 1 NOS2
Mitochondrion inner membrane 1 CYP1A1
Membrane raft 1 TNF
Peroxisome 1 NOS2
peroxisomal matrix 1 NOS2
Nucleus, PML body 1 MTOR
PML body 1 MTOR
Late endosome 1 TF
receptor complex 1 PPARG
neuron projection 1 CHAT
ciliary basal body 1 ALB
chromatin 1 PPARG
stereocilium bundle 1 IDO1
phagocytic cup 1 TNF
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 2 ALB, TF
nuclear envelope 1 MTOR
Endomembrane system 1 MTOR
basal plasma membrane 1 TF
secretory granule lumen 2 DBH, TF
HFE-transferrin receptor complex 1 TF
secretory granule membrane 1 DBH
endoplasmic reticulum lumen 3 ALB, IL6, TF
platelet alpha granule lumen 1 ALB
endocytic vesicle 1 TF
clathrin-coated endocytic vesicle membrane 1 TF
Cytoplasmic vesicle, secretory vesicle membrane 1 DBH
Cytoplasmic vesicle, phagosome 1 MTOR
vesicle coat 1 TF
Cytoplasmic vesicle, secretory vesicle, chromaffin granule lumen 1 DBH
chromaffin granule lumen 1 DBH
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
transport vesicle membrane 1 DBH
cortical cytoskeleton 1 NOS2
interleukin-6 receptor complex 1 IL6
[Soluble dopamine beta-hydroxylase]: Cytoplasmic vesicle, secretory vesicle lumen 1 DBH
Cytoplasmic vesicle, secretory vesicle, chromaffin granule membrane 1 DBH
chromaffin granule membrane 1 DBH
smooth muscle contractile fiber 1 IDO1
ciliary transition fiber 1 ALB
dense body 1 TF
interleukin-28 receptor complex 1 IFNLR1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Yu Li, Lu Wei, Pengfei Zhang, Juan Xiao, Zhiqiang Guo, Qiongyao Fu. Bioaccumulation of dietary CrPic, Cr(III) and Cr(VI) in juvenile coral trout (Plectropomus leopardus). Ecotoxicology and environmental safety. 2022 Jul; 240(?):113692. doi: 10.1016/j.ecoenv.2022.113692. [PMID: 35636236]
  • Vivekananda Mandal, Narendra Nath Ghosh, Prashanta Kumar Mitra, Sukhendu Mandal, Vivekananda Mandal. Production and characterization of a broad-spectrum antimicrobial 5-butyl-2-pyridine carboxylic acid from Aspergillus fumigatus nHF-01. Scientific reports. 2022 04; 12(1):6006. doi: 10.1038/s41598-022-09925-z. [PMID: 35397665]
  • Murat Cihan, Özlem Doğan, Ceyhan Ceran Serdar, Arzu Altunçekiç Yıldırım, Celali Kurt, Muhittin A Serdar. Kynurenine pathway in Coronavirus disease (COVID-19): Potential role in prognosis. Journal of clinical laboratory analysis. 2022 Mar; 36(3):e24257. doi: 10.1002/jcla.24257. [PMID: 35092710]
  • Hassan Mozaffari-Khosravi, Sara Jambarsan, Fazad Karimpour, Seyyed Ebrahim Hosseini, Behrooz Ebrahimzadeh Kour. Study Protocol for a Randomized Controlled Trial Evaluating the Effectof Chromium Picolinate Supplementation on Gene Expression of TumorNecrosis Factor-α and DNA Damage in Metabolic Syndrome Patients. Saudi journal of kidney diseases and transplantation : an official publication of the Saudi Center for Organ Transplantation, Saudi Arabia. 2021 Nov; 32(6):1671-1678. doi: 10.4103/1319-2442.352428. [PMID: 35946280]
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  • Katarzyna Ognik, Wojciech Dworzański, Iwona Sembratowicz, Bartosz Fotschki, Ewelina Cholewińska, Piotr Listos, Jerzy Juśkiewicz. The effect of the high-fat diet supplemented with various forms of chromium on rats body composition, liver metabolism and organ histology Cr in liver metabolism and histology of selected organs. Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS). 2021 Mar; 64(?):126705. doi: 10.1016/j.jtemb.2020.126705. [PMID: 33383354]
  • Alexandra N Kovács, Norbert Varga, Ádám Juhász, Edit Csapó. Serum protein-hyaluronic acid complex nanocarriers: Structural characterisation and encapsulation possibilities. Carbohydrate polymers. 2021 Jan; 251(?):117047. doi: 10.1016/j.carbpol.2020.117047. [PMID: 33142605]
  • Fardin Moradi, Fateme Kooshki, Forough Nokhostin, Manouchehr Khoshbaten, Hadi Bazyar, Bahram Pourghassem Gargari. A pilot study of the effects of chromium picolinate supplementation on serum fetuin-A, metabolic and inflammatory factors in patients with nonalcoholic fatty liver disease: A double-blind, placebo-controlled trial. Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS). 2021 Jan; 63(?):126659. doi: 10.1016/j.jtemb.2020.126659. [PMID: 33045675]
  • Yang Hai, Mengbin Chen, Arthur Huang, Yi Tang. Biosynthesis of Mycotoxin Fusaric Acid and Application of a PLP-Dependent Enzyme for Chemoenzymatic Synthesis of Substituted l-Pipecolic Acids. Journal of the American Chemical Society. 2020 11; 142(46):19668-19677. doi: 10.1021/jacs.0c09352. [PMID: 33155797]
  • Ferenc Tömösi, Gábor Kecskeméti, Edina Katalin Cseh, Elza Szabó, Cecília Rajda, Róbert Kormány, Zoltán Szabó, László Vécsei, Tamás Janáky. A validated UHPLC-MS method for tryptophan metabolites: Application in the diagnosis of multiple sclerosis. Journal of pharmaceutical and biomedical analysis. 2020 Jun; 185(?):113246. doi: 10.1016/j.jpba.2020.113246. [PMID: 32182446]
  • Thomas I Kostelnik, Xiaozhu Wang, Lily Southcott, Hannah K Wagner, Manja Kubeil, Holger Stephan, María de Guadalupe Jaraquemada-Peláez, Chris Orvig. Rapid Thermodynamically Stable Complex Formation of [nat/111In]In3+, [nat/90Y]Y3+, and [nat/177Lu]Lu3+ with H6dappa. Inorganic chemistry. 2020 May; 59(10):7238-7251. doi: 10.1021/acs.inorgchem.0c00671. [PMID: 32337985]
  • Kehong Ding, Meghan E McGee-Lawrence, Helen Kaiser, Anuj K Sharma, Jessica L Pierce, Debra L Irsik, Wendy B Bollag, Jianrui Xu, Qing Zhong, William Hill, Xing-Ming Shi, Sadanand Fulzele, Eileen J Kennedy, Mohammed Elsalanty, Mark W Hamrick, Carlos M Isales. Picolinic acid, a tryptophan oxidation product, does not impact bone mineral density but increases marrow adiposity. Experimental gerontology. 2020 05; 133(?):110885. doi: 10.1016/j.exger.2020.110885. [PMID: 32088397]
  • Praveen K Kathare, Sunethra Dharmasiri, Eric D Vincill, Pratyush Routray, Idrees Ahmad, Daniel M Roberts, Nihal Dharmasiri. Arabidopsis PIC30 encodes a major facilitator superfamily transporter responsible for the uptake of picolinate herbicides. The Plant journal : for cell and molecular biology. 2020 04; 102(1):18-33. doi: 10.1111/tpj.14608. [PMID: 31710151]
  • Shan Shan Qi, Hong Xing Zheng, Hai Jiang, Li Ping Yuan, Le Chen Dong. Protective Effects of Chromium Picolinate Against Diabetic-Induced Renal Dysfunction and Renal Fibrosis in Streptozotocin-Induced Diabetic Rats. Biomolecules. 2020 03; 10(3):. doi: 10.3390/biom10030398. [PMID: 32143429]
  • Ragip Pala, Mehmet Akif Sari, Fusun Erten, Besir Er, Mehmet Tuzcu, Cemal Orhan, Patrick Brice Defo Deeh, Nurhan Sahin, Vedat Cinar, James R Komorowski, Kazim Sahin. The effects of chromium picolinate on glucose and lipid metabolism in running rats. Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS). 2020 Mar; 58(?):126434. doi: 10.1016/j.jtemb.2019.126434. [PMID: 31778961]
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  • Patrick Heilman, Matthew N Hill, Mary Coussons-Read, Lena Brundin, Emil F Coccaro. Role of the kynurenine pathway and the endocannabinoid system as modulators of inflammation and personality traits. Psychoneuroendocrinology. 2019 12; 110(?):104434. doi: 10.1016/j.psyneuen.2019.104434. [PMID: 31525567]
  • Carlos Eduardo Aucique-Pérez, Renata Sousa Resende, Lara Beatriz Cruz Neto, Fernanda Dornelas, Fábio Murilo DaMatta, Fabrício Ávila Rodrigues. Picolinic acid spray stimulates the antioxidative metabolism and minimizes impairments on photosynthesis on wheat leaves infected by Pyricularia oryzae. Physiologia plantarum. 2019 Dec; 167(4):628-644. doi: 10.1111/ppl.12917. [PMID: 30628091]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
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  • Diana Ciubotariu, Mihai Nechifor, Gabriel Dimitriu. Chromium picolinate reduces morphine-dependence in rats, while increasing brain serotonin levels. Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS). 2018 Dec; 50(?):676-683. doi: 10.1016/j.jtemb.2018.06.025. [PMID: 30269760]
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  • Mohamed Mahmoud Elseweidy, Rawia Sarhan Amin, Hebatallah Husseini Atteia, Maha Abdo Aly. Nigella sativa Oil and Chromium Picolinate Ameliorate Fructose-Induced Hyperinsulinemia by Enhancing Insulin Signaling and Suppressing Insulin-Degrading Enzyme in Male Rats. Biological trace element research. 2018 Jul; 184(1):119-126. doi: 10.1007/s12011-017-1167-z. [PMID: 28975521]
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  • Noha M Shafik, Amal Baalash, Abla M Ebeid. Synergistic Cardioprotective Effects of Combined Chromium Picolinate and Atorvastatin Treatment in Triton X-100-Induced Hyperlipidemia in Rats: Impact on Some Biochemical Markers. Biological trace element research. 2017 Dec; 180(2):255-264. doi: 10.1007/s12011-017-1010-6. [PMID: 28409410]
  • Zhigang Wang, Shuhan Tang, Masao Hattori, Hailong Zhang, Xiuhong Wu. Simultaneous determination of paeonilactone A and paeonilactone B in rat plasma after oral administration of albiflorin by UPLC/TOF/MS following picolinoyl derivatization. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Sep; 1061-1062(?):327-333. doi: 10.1016/j.jchromb.2017.07.047. [PMID: 28783562]
  • Rituparna Ganguly, Soumyadip Sahu, Vahagn Ohanyan, Rebecca Haney, Ronaldo J Chavez, Shivani Shah, Siri Yalamanchili, Priya Raman. Oral chromium picolinate impedes hyperglycemia-induced atherosclerosis and inhibits proatherogenic protein TSP-1 expression in STZ-induced type 1 diabetic ApoE-/- mice. Scientific reports. 2017 03; 7(?):45279. doi: 10.1038/srep45279. [PMID: 28345659]
  • Tianzhu Zang, Daniel Tamae, Clementina Mesaros, Qingqing Wang, Meng Huang, Ian A Blair, Trevor M Penning. Simultaneous quantitation of nine hydroxy-androgens and their conjugates in human serum by stable isotope dilution liquid chromatography electrospray ionization tandem mass spectrometry. The Journal of steroid biochemistry and molecular biology. 2017 01; 165(Pt B):342-355. doi: 10.1016/j.jsbmb.2016.08.001. [PMID: 27531846]
  • Emil F Coccaro, Royce Lee, Jennifer R Fanning, Dietmar Fuchs, Michel Goiny, Sophie Erhardt, Kyle Christensen, Lena Brundin, Mary Coussons-Read. Tryptophan, kynurenine, and kynurenine metabolites: Relationship to lifetime aggression and inflammatory markers in human subjects. Psychoneuroendocrinology. 2016 09; 71(?):189-96. doi: 10.1016/j.psyneuen.2016.04.024. [PMID: 27318828]
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