Pyridoxal 5'-phosphate (BioDeep_00000001641)

 

Secondary id: BioDeep_00000400288, BioDeep_00000400435

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Chemicals and Drugs


代谢物信息卡片


Phosphoric acid mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester

化学式: C8H10NO6P (247.024573)
中文名称: 磷酸吡哆醛, 磷酸-吡哆醛, 磷酸吡哆醛, 5-磷酸吡哆醛, 磷酸吡哆醛水合物
谱图信息: 最多检出来源 Homo sapiens(blood) 0.1%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

Pyridoxal 5'-phosphate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/pyridoxal_5_-phosphate (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000001641). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC1=NC=C(C(=C1O)C=O)COP(=O)(O)O
InChI: InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)

描述信息

Pyridoxal phosphate, also known as PLP, pyridoxal 5-phosphate or P5P, is the active form of vitamin B6. It is a coenzyme in a variety of enzymatic reactions. Pyridoxal 5-phosphate belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives are compounds containing a pyridoxal moiety, which consists of a pyridine ring substituted at positions 2,3,4, and 5 by a methyl group, a hydroxyl group, a carbaldehyde group, and a hydroxymethyl group, respectively. Pyridoxal 5-phosphate is a drug which is used for nutritional supplementation and for treating dietary shortage or imbalance. Pyridoxal 5-phosphate exists in all living species, ranging from bacteria to humans. In humans, pyridoxal 5-phosphate is involved in glycine and serine metabolism. Outside of the human body, pyridoxal 5-phosphate is found, on average, in the highest concentration within cow milk. Pyridoxal 5-phosphate has also been detected, but not quantified in several different foods, such as soursops, italian sweet red peppers, muscadine grapes, european plums, and blackcurrants. Pyridoxal 5-phosphate, with regard to humans, has been found to be associated with several diseases such as epilepsy, early-onset, vitamin B6-dependent, odontohypophosphatasia, pyridoxamine 5-prime-phosphate oxidase deficiency, and hypophosphatasia. Pyridoxal 5-phosphate has also been linked to the inborn metabolic disorder celiac disease.
This is the active form of vitamin B6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (pyridoxamine). -- Pubchem; Pyridoxal-phosphate (PLP, pyridoxal-5-phosphate) is a cofactor of many enzymatic reactions. It is the active form of vitamin B6 which comprises three natural organic compounds, pyridoxal, pyridoxamine and pyridoxine. -- Wikipedia [HMDB]. Pyridoxal 5-phosphate is found in many foods, some of which are linden, kai-lan, nance, and rose hip.
Acquisition and generation of the data is financially supported in part by CREST/JST.
A - Alimentary tract and metabolism > A11 - Vitamins
D018977 - Micronutrients > D014815 - Vitamins
KEIO_ID P038
Pyridoxal phosphate is the active form of vitamin B6, acts as an inhibitor of reverse transcriptases, and is used for the treatment of tardive dyskinesia.

同义名列表

45 个代谢物同义名

Phosphoric acid mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester; 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphoric acid; Phosphate mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester; 3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde; 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphate; [(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid; Pyridoxal 5-(dihydrogen phosphoric acid); Pyridoxal 5-monophosphoric acid ester; Pyridoxal 5-(dihydrogen phosphate); Pyridoxal-5-phosphate monohydrate; Pyridoxal 5-monophosphate ester; Pyridoxal-5-phosphate hydrate; PYRIDOXAL-5-phosphoric acid; Pyridoxal 5-phosphoric acid; Pyridoxal phosphoric acid; Phosphopyridoxal coenzyme; PYRIDOXAL-5-phosphATE; Pyridoxal 5-phosphate; Pyridoxal 5 phosphate; Phosphate, pyridoxal; Pyridoxyl phosphate; pyridoxal phosphate; Phosphopyridoxal; Codecarboxylase; Hi-pyridoxin; Pyridoxal p; Coenzyme b6; Pyridoxal-p; Vitahexin-p; Hexermin-p; Pidopidon; Sechvitan; Apolon b6; Vitazechs; Pyromijin; Hiadelon; Biosechs; Hairoxal; Pydoxal; Himitan; Piodel; PAL-p; PLP; Pyridoxal 5′-phosphate; Pyridoxal 5'-phosphate



数据库引用编号

39 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(6)

BioCyc(1)

PlantCyc(0)

代谢反应

431 个相关的代谢反应过程信息。

Reactome(25)

BioCyc(4)

WikiPathways(2)

Plant Reactome(387)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(1)

PathBank(11)

  • Vitamin B6 Metabolism: Oxygen + Pyridoxamine 5'-phosphate + Water ⟶ Ammonia + Hydrogen peroxide + Pyridoxal 5'-phosphate
  • Vitamin B6: 2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamic acid ⟶ O-Phospho-4-hydroxy-L-threonine + Oxoglutaric acid
  • Vitamin B6 Metabolism: 4-Pyridoxic acid ⟶ 2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylate
  • Hypophosphatasia: 4-Pyridoxic acid ⟶ 2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylate
  • Vitamin B6 Metabolism: 4-Pyridoxic acid ⟶ 2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylate
  • Hypophosphatasia: 4-Pyridoxic acid ⟶ 2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylate
  • Vitamin B6 Metabolism: 4-Pyridoxic acid ⟶ 2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylate
  • Vitamin B6 Metabolism: 4-Pyridoxic acid ⟶ 2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylate
  • Vitamin B6 Metabolism: 4-Pyridoxic acid ⟶ 2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylate
  • Vitamin B6 Metabolism: 4-Pyridoxic acid ⟶ 2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylate
  • Hypophosphatasia: 4-Pyridoxic acid ⟶ 2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylate

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

  • Qizhen Cui, Qingqing Liu, Yutong Fan, Chenhe Wang, Yufei Li, Shuyuan Li, Jianguo Zhang, Guodong Rao. Functional differentiation of olive PLP_deC genes: insights into metabolite biosynthesis and genetic improvement at the whole-genome level. Plant cell reports. 2024 Apr; 43(5):127. doi: 10.1007/s00299-024-03212-z. [PMID: 38652203]
  • Priscille Steensma, Marion Eisenhut, Maite Colinas, Laise Rosado-Souza, Alisdair R Fernie, Andreas P M Weber, Teresa B Fitzpatrick. PYRIDOX(AM)INE 5'-PHOSPHATE OXIDASE3 of Arabidopsis thaliana maintains carbon/nitrogen balance in distinct environmental conditions. Plant physiology. 2023 09; 193(2):1433-1455. doi: 10.1093/plphys/kiad411. [PMID: 37453131]
  • Jenny U Tran, Breann L Brown. The yeast ALA synthase C-terminus positively controls enzyme structure and function. Protein science : a publication of the Protein Society. 2023 Feb; ?(?):e4600. doi: 10.1002/pro.4600. [PMID: 36807942]
  • Maria Rutkiewicz, Isabel Nogues, Wojciech Witek, Sebastiana Angelaccio, Roberto Contestabile, Milosz Ruszkowski. Insights into the substrate specificity, structure, and dynamics of plant histidinol-phosphate aminotransferase (HISN6). Plant physiology and biochemistry : PPB. 2023 Feb; 196(?):759-773. doi: 10.1016/j.plaphy.2023.02.017. [PMID: 36842242]
  • Kaan Koper, Shogo Hataya, Andrew G Hall, Taichi E Takasuka, Hiroshi A Maeda. Biochemical characterization of plant aromatic aminotransferases. Methods in enzymology. 2023; 680(?):35-83. doi: 10.1016/bs.mie.2022.07.034. [PMID: 36710018]
  • Je Won Ko, Sookyoung Jeon, Young Hye Kwon. Dietary vitamin B6 restriction aggravates neurodegeneration in mice fed a high-fat diet. Life sciences. 2022 Nov; 309(?):121041. doi: 10.1016/j.lfs.2022.121041. [PMID: 36208656]
  • Dennis Schlossarek, Marcin Luzarowski, Ewelina M Sokołowska, Venkatesh P Thirumalaikumar, Lisa Dengler, Lothar Willmitzer, Jennifer C Ewald, Aleksandra Skirycz. Rewiring of the protein-protein-metabolite interactome during the diauxic shift in yeast. Cellular and molecular life sciences : CMLS. 2022 Oct; 79(11):550. doi: 10.1007/s00018-022-04569-8. [PMID: 36242648]
  • Naoufal Lakhssassi, Dounya Knizia, Abdelhalim El Baze, Aicha Lakhssassi, Jonas Meksem, Khalid Meksem. Proteomic, Transcriptomic, Mutational, and Functional Assays Reveal the Involvement of Both THF and PLP Sites at the GmSHMT08 in Resistance to Soybean Cyst Nematode. International journal of molecular sciences. 2022 Sep; 23(19):. doi: 10.3390/ijms231911278. [PMID: 36232579]
  • Yeong-Biau Yu, Douglas O Adams, Shang Fa Yang. Reprint of: 1-Aminocyclopropanecarboxylate Synthase, a Key Enzyme in Ethylene Biosynthesis. Archives of biochemistry and biophysics. 2022 09; 726(?):109238. doi: 10.1016/j.abb.2022.109238. [PMID: 35680445]
  • Joanna L Clasen, Alicia K Heath, Heleen Van Puyvelde, Inge Huybrechts, Jin Young Park, Pietro Ferrari, Ghislaine Scelo, Arve Ulvik, Øivind Midttun, Per Magne Ueland, Kim Overvad, Anne Kirstine Eriksen, Anne Tjønneland, Rudolf Kaaks, Verena Katzke, Matthias B Schulze, Domenico Palli, Claudia Agnoli, Paolo Chiodini, Rosario Tumino, Carlotta Sacerdote, Raul Zamora-Ros, Miguel Rodriguez-Barranco, Carmen Santiuste, Eva Ardanaz, Pilar Amiano, Julie A Schmidt, Elisabete Weiderpass, Marc Gunter, Elio Riboli, Amanda J Cross, Mattias Johansson, David C Muller. Biomarkers of the transsulfuration pathway and risk of renal cell carcinoma in the European Prospective Investigation into Cancer and Nutrition (EPIC) study. International journal of cancer. 2022 09; 151(5):708-716. doi: 10.1002/ijc.34009. [PMID: 35366005]
  • Hao-Hua Deng, Hui-Jing Yang, Kai-Yuan Huang, Yi-Jing Zheng, Ying-Ying Xu, Hua-Ping Peng, Yin-Huan Liu, Wei Chen, Guo-Lin Hong. Antenna effect of pyridoxal phosphate on the fluorescence of mitoxantrone-silicon nanoparticles and its application in alkaline phosphatase assay. Analytical and bioanalytical chemistry. 2022 Jul; 414(17):4877-4884. doi: 10.1007/s00216-022-04110-7. [PMID: 35576012]
  • Chaoran Ma, Qipin Chen, Diane C Mitchell, Muzi Na, Katherine L Tucker, Xiang Gao. Application of the deep learning algorithm in nutrition research - using serum pyridoxal 5'-phosphate as an example. Nutrition journal. 2022 06; 21(1):38. doi: 10.1186/s12937-022-00793-x. [PMID: 35689265]
  • Lei Xu, Yu-Jing Fang, Meng-Meng Che, Alinuer Abulimiti, Chu-Yi Huang, Cai-Xia Zhang. Association of Serum Pyridoxal-5'-Phosphate, Pyridoxal, and PAr with Colorectal Cancer Risk: A Large-Scale Case-Control Study. Nutrients. 2022 Jun; 14(12):. doi: 10.3390/nu14122389. [PMID: 35745119]
  • Hyojung Kim, Evelyn B Enrione, Vijaya Narayanan, Tan Li, Adriana Campa. Associations of Vitamin B6 Intake and Plasma Pyridoxal 5'-Phosphate with Plasma Polyunsaturated Fatty Acids in US Older Adults: Findings from NHANES 2003-2004. Nutrients. 2022 Jun; 14(11):. doi: 10.3390/nu14112336. [PMID: 35684138]
  • Jacqueline Altensell, Ruth Wartenberg, Ilka Haferkamp, Sebastian Hassler, Vanessa Scherer, Priscille Steensma, Teresa B Fitzpatrick, Anurag Sharma, Omar Sandoval-Ibañez, Mathias Pribil, Martin Lehmann, Dario Leister, Tatjana Kleine, H Ekkehard Neuhaus. Loss of a pyridoxal-phosphate phosphatase rescues Arabidopsis lacking an endoplasmic reticulum ATP carrier. Plant physiology. 2022 05; 189(1):49-65. doi: 10.1093/plphys/kiac048. [PMID: 35139220]
  • Zhi-Bin Li, Li-Ying Shi, Yu-Shuai Han, Jing Chen, Shan-Qiang Zhang, Jia-Xi Chen, Jun Liu, Hui-Hui Tu, Qi-Qi Lu, Yi Yu, Ting-Ting Jiang, Ji-Cheng Li. Pyridoxal phosphate, pyridoxamine phosphate, and folic acid based on ceRNA regulatory network as potential biomarkers for the diagnosis of pulmonary tuberculosis. Infection, genetics and evolution : journal of molecular epidemiology and evolutionary genetics in infectious diseases. 2022 04; 99(?):105240. doi: 10.1016/j.meegid.2022.105240. [PMID: 35150890]
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  • Atsushi Okawa, Haruhisa Handa, Eri Yasuda, Masaki Murota, Daizo Kudo, Takashi Tamura, Tomoo Shiba, Kenji Inagaki. Characterization and application of l-methionine γ-lyase Q349S mutant enzyme with an enhanced activity toward l-homocysteine. Journal of bioscience and bioengineering. 2022 Mar; 133(3):213-221. doi: 10.1016/j.jbiosc.2021.11.008. [PMID: 34953671]
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  • Chuxi Pan, Alexandra Zimmer, Megha Shah, Minh Sang Huynh, Christine Chieh-Lin Lai, Brandon Sit, Yogesh Hooda, David M Curran, Trevor F Moraes. Actinobacillus utilizes a binding protein-dependent ABC transporter to acquire the active form of vitamin B6. The Journal of biological chemistry. 2021 09; 297(3):101046. doi: 10.1016/j.jbc.2021.101046. [PMID: 34358566]
  • Mathias D G Van den Eynde, Jean L J M Scheijen, Coen D A Stehouwer, Toshio Miyata, Casper G Schalkwijk. Quantification of the B6 vitamers in human plasma and urine in a study with pyridoxamine as an oral supplement; pyridoxamine as an alternative for pyridoxine. Clinical nutrition (Edinburgh, Scotland). 2021 07; 40(7):4624-4632. doi: 10.1016/j.clnu.2021.05.028. [PMID: 34229268]
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  • Mark M Kushnir, Boya Song, Evelyn Yang, Elizabeth L Frank. Development and Clinical Evaluation of a High-Throughput LC-MS/MS Assay for Vitamin B6 in Human Plasma and Serum. The journal of applied laboratory medicine. 2021 04; 6(3):702-714. doi: 10.1093/jalm/jfaa166. [PMID: 33279978]
  • Peter Cuthbertson, Nicholas J Geraghty, Sam R Adhikary, Sienna Casolin, Debbie Watson, Ronald Sluyter. P2X7 receptor antagonism increases regulatory T cells and reduces clinical and histological graft-versus-host disease in a humanised mouse model. Clinical science (London, England : 1979). 2021 02; 135(3):495-513. doi: 10.1042/cs20201352. [PMID: 33463682]
  • Hyojung Kim, Evelyn B Enrione, Vijaya Narayanan, Tan Li, Adriana Campa. Gender Differences in the Associations of Plasma Pyridoxal 5'-Phosphate with Plasma Polyunsaturated Fatty Acids among US Young and Middle-Aged Adults: NHANES 2003-2004. Nutrients. 2021 Jan; 13(2):. doi: 10.3390/nu13020477. [PMID: 33572554]
  • Qichen Long, Tianqi Qi, Tianjiao Zhang, Jing Wang, Jie Zeng, Ying Yan, Meng Wang, Wei Huang, Haijian Zhao, Wenxiang Chen, Chuanbao Zhang. Commutability Assessment of Candidate External Quality Assessment Materials for Aminotransferase Activity Measurements Based on Different Approaches in China. Annals of laboratory medicine. 2021 01; 41(1):68-76. doi: 10.3343/alm.2021.41.1.68. [PMID: 32829581]
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  • Alexandra Jungert, Helene McNulty, Leane Hoey, Mary Ward, J J Strain, Catherine F Hughes, Liadhan McAnena, Monika Neuhäuser-Berthold, Kristina Pentieva. Riboflavin Is an Important Determinant of Vitamin B-6 Status in Healthy Adults. The Journal of nutrition. 2020 10; 150(10):2699-2706. doi: 10.1093/jn/nxaa225. [PMID: 32805038]
  • Juliette Bouchereau, Manuel Schiff. Inherited Disorders of Lysine Metabolism: A Review. The Journal of nutrition. 2020 10; 150(Suppl 1):2556S-2560S. doi: 10.1093/jn/nxaa112. [PMID: 33000154]
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  • Dinesh Talwar, Anthony Catchpole, John M Wadsworth, Barry J Toole, Donald C McMillan. The relationship between plasma albumin, alkaline phosphatase and pyridoxal phosphate concentrations in plasma and red cells: Implications for assessing vitamin B6 status. Clinical nutrition (Edinburgh, Scotland). 2020 09; 39(9):2824-2831. doi: 10.1016/j.clnu.2019.12.012. [PMID: 31883613]
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