Pyridoxamine 5'-phosphate (BioDeep_00000001419)

 

Secondary id: BioDeep_00001868472

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite natural product Volatile Flavor Compounds


代谢物信息卡片


{[4-(aminomethyl)-5-hydroxy-6-methylpyridin-3-yl]methoxy}phosphonic acid

化学式: C8H13N2O5P (248.05620580000001)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 0.03%

分子结构信息

SMILES: CC1=NC=C(C(=C1O)CN)COP(=O)(O)O
InChI: InChI=1S/C8H13N2O5P/c1-5-8(11)7(2-9)6(3-10-5)4-15-16(12,13)14/h3,11H,2,4,9H2,1H3,(H2,12,13,14)

描述信息

Pyridoxamine 5-phosphate belongs to the class of organic compounds known as pyridoxamine 5-phosphates. These are heterocyclic aromatic compounds containing a pyridoxamine that carries a phosphate group at the 5-position. Vitamin B6 is a water-soluble compound that was discovered in 1930s during nutrition studies on rats. The vitamin was named pyridoxine to indicate its structural homology to pyridine. Later it was shown that vitamin B6 could exist in two other, slightly different, chemical forms, termed pyridoxal and pyridoxamine. All three forms of vitamin B6 are precursors of an activated compound known as pyridoxal 5-phosphate (PLP), which plays a vital role as the cofactor of a large number of essential enzymes in the human body. Vitamin B6 is a water-soluble vitamin. The three major forms of vitamin B6 are pyridoxine (also known as pyridoxol), pyridoxal, and pyridoxamine, which are all converted in the liver to pyridoxal 5-phosphate (PLP) a cofactor in many reactions of amino acid metabolism. PLP also is necessary for the enzymatic reaction governing the release of glucose from glycogen.
Vitamin B6 is a water-soluble compound that was discovered in 1930s during nutrition studies on rats. The vitamin was named pyridoxine to indicate its structural homology to pyridine. Later it was shown that vitamin B6 could exist in two other, slightly different, chemical forms, termed pyridoxal and pyridoxamine. All three forms of vitamin B6 are precursors of an activated compound known as pyridoxal 5-phosphate (PLP), which plays a vital role as the cofactor of a large number of essential enzymes in the human body.
KEIO_ID P113; [MS3] KO009146
KEIO_ID P113; [MS2] KO009143
KEIO_ID P113

同义名列表

18 个代谢物同义名

{[4-(aminomethyl)-5-hydroxy-6-methylpyridin-3-yl]methoxy}phosphonic acid; 4-Aminomethyl-5-hydroxy-6-methyl-3-pyridylmethyl phosphate; 4’-Deoxy-4’-aminopyridoxal-5’-phosphoric acid; Pyridoxamine 5-(dihydrogen phosphoric acid); 4-Deoxy-4-aminopyridoxal-5-phosphoric acid; 4’-Deoxy-4’-aminopyridoxal-5’-phosphate; Pyridoxamine 5-(dihydrogen phosphate); 4-Deoxy-4-aminopyridoxal-5-phosphate; Pyridoxamine 5-phosphoric acid; Pyridoxamine phosphoric acid; Pyridoxamine 5’-phosphate; pyridoxamine-5-phosphate; Pyridoxamine 5-phosphate; Pyridoxamine 5-phospate; pyridoxamine phosphate; Pyridoxamine-P; PMP; Pyridoxamine phosphate



数据库引用编号

35 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(0)

PlantCyc(0)

代谢反应

330 个相关的代谢反应过程信息。

Reactome(72)

BioCyc(2)

WikiPathways(1)

Plant Reactome(243)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(11)

  • 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: Oxygen + Pyridoxamine 5'-phosphate + Water ⟶ Ammonia + Hydrogen peroxide + Pyridoxal 5'-phosphate
  • 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)

24 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

  • 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]
  • Ghada Rashad Ibrahim, Iltaf Shah, Salah Gariballa, Javed Yasin, James Barker, Syed Salman Ashraf. Significantly Elevated Levels of Plasma Nicotinamide, Pyridoxal, and Pyridoxamine Phosphate Levels in Obese Emirati Population: A Cross-Sectional Study. Molecules (Basel, Switzerland). 2020 Aug; 25(17):. doi: 10.3390/molecules25173932. [PMID: 32872122]
  • 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]
  • Maite Colinas, Marion Eisenhut, Takayuki Tohge, Marta Pesquera, Alisdair R Fernie, Andreas P M Weber, Teresa B Fitzpatrick. Balancing of B6 Vitamers Is Essential for Plant Development and Metabolism in Arabidopsis. The Plant cell. 2016 Feb; 28(2):439-53. doi: 10.1105/tpc.15.01033. [PMID: 26858304]
  • Shannon C K Straub, Mark Fishbein, Tatyana Livshultz, Zachary Foster, Matthew Parks, Kevin Weitemier, Richard C Cronn, Aaron Liston. Building a model: developing genomic resources for common milkweed (Asclepias syriaca) with low coverage genome sequencing. BMC genomics. 2011 May; 12(?):211. doi: 10.1186/1471-2164-12-211. [PMID: 21542930]
  • Hsin-Yueh Chang, Jason T C Tzen, Su-Jen Lin, Yi-Ting Wu, En-Pei Isabel Chiang. Long-term prednisolone treatments increase bioactive vitamin B6 synthesis in vivo. The Journal of pharmacology and experimental therapeutics. 2011 Apr; 337(1):102-9. doi: 10.1124/jpet.110.174839. [PMID: 21205917]
  • Martin Busch, Andrea Göbert, Sybille Franke, Undine Ott, Jens Gerth, Andreas Müller, Günter Stein, Roland Bitsch, Gunter Wolf. Vitamin B6 metabolism in chronic kidney disease--relation to transsulfuration, advanced glycation and cardiovascular disease. Nephron. Clinical practice. 2010; 114(1):c38-46. doi: 10.1159/000245068. [PMID: 19816042]
  • Michel Havaux, Brigitte Ksas, Agnieszka Szewczyk, Dominique Rumeau, Fabrice Franck, Stefano Caffarri, Christian Triantaphylidès. Vitamin B6 deficient plants display increased sensitivity to high light and photo-oxidative stress. BMC plant biology. 2009 Nov; 9(?):130. doi: 10.1186/1471-2229-9-130. [PMID: 19903353]
  • Marcin L Marszałł, Anna Lebiedzińska, Wojciech Czarnowski, Ryszard Makarowski, Mateusz Kłos, Piotr Szefer. Application of the high-performance liquid chromatography method with coulometric detection for determination of vitamin B(6) in human plasma and serum. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2009 Oct; 877(27):3151-8. doi: 10.1016/j.jchromb.2009.08.014. [PMID: 19733133]
  • Jasmina Saric, Jia V Li, Yulan Wang, Jennifer Keiser, Jake G Bundy, Elaine Holmes, Jürg Utzinger. Metabolic profiling of an Echinostoma caproni infection in the mouse for biomarker discovery. PLoS neglected tropical diseases. 2008 Jul; 2(7):e254. doi: 10.1371/journal.pntd.0000254. [PMID: 18596973]
  • Yuying Sang, Jose M Barbosa, Hongzhuan Wu, Robert D Locy, Narendra K Singh. Identification of a pyridoxine (pyridoxamine) 5'-phosphate oxidase from Arabidopsis thaliana. FEBS letters. 2007 Feb; 581(3):344-8. doi: 10.1016/j.febslet.2006.12.028. [PMID: 17224143]
  • Vikrant M Bhor, Sagarika Dev, Ganga Ramu Vasanthakumar, Avadhesha Surolia. Spectral and kinetic characterization of 7,8-diaminopelargonic acid synthase from Mycobacterium tuberculosis. IUBMB life. 2006 Apr; 58(4):225-33. doi: 10.1080/15216540600746997. [PMID: 16754301]
  • Karina R Lora, David W Giraud, Sarah R Davy, Judy A Driskell. Children of Latino immigrants, 4-8 years, in rural Nebraska are adequate in vitamin B-6. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition. 2006 Mar; 76(2):47-56. doi: 10.1024/0300-9831.76.2.47. [PMID: 16941415]
  • Edward W T Tsang, Zhiyuan Hu, Qing Chang, D Ian McGregor, Wilfred A Keller. Expression of a Brassic napus glutamate 1-semialdehyde aminotransferase in Escherichia coli and characterization of the recombinant protein. Protein expression and purification. 2003 Jun; 29(2):193-201. doi: 10.1016/s1046-5928(03)00010-x. [PMID: 12767809]
  • Brian W Noland, Janet M Newman, Jörg Hendle, John Badger, Jon A Christopher, Jason Tresser, Michelle D Buchanan, Tobi A Wright, Marc E Rutter, Wendy E Sanderson, Hans Joachim Müller-Dieckmann, Ketan S Gajiwala, Sean G Buchanan. Structural studies of Salmonella typhimurium ArnB (PmrH) aminotransferase: a 4-amino-4-deoxy-L-arabinose lipopolysaccharide-modifying enzyme. Structure (London, England : 1993). 2002 Nov; 10(11):1569-80. doi: 10.1016/s0969-2126(02)00879-1. [PMID: 12429098]
  • T T Nguyen, T Hayakawa, H Tsuge. Effect of vitamin B6 deficiency on the synthesis and accumulation of S-adenosylhomocysteine and S-adenosylmethionine in rat tissues. Journal of nutritional science and vitaminology. 2001 Jun; 47(3):188-94. doi: 10.3177/jnsv.47.188. [PMID: 11575573]
  • C M Hansen, T D Shultz, H K Kwak, H S Memon, J E Leklem. Assessment of vitamin B-6 status in young women consuming a controlled diet containing four levels of vitamin B-6 provides an estimated average requirement and recommended dietary allowance. The Journal of nutrition. 2001 Jun; 131(6):1777-86. doi: 10.1093/jn/131.6.1777. [PMID: 11385067]
  • J A Driskell, D W Giraud, S H Mitmesser. Vitamin B-6 intakes and plasma B-6 vitamer concentrations of men and women, 19-50 years of age. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition. 2000 Sep; 70(5):221-5. doi: 10.1024/0300-9831.70.5.221. [PMID: 11068702]
  • S C Bai, Q R Rogers, D L Wong, D A Sampson, J G Morris. Vitamin B-6 deficiency and level of dietary protein affect hepatic tyrosine aminotransferase activity in cats. The Journal of nutrition. 1998 Nov; 128(11):1995-2000. doi: 10.1093/jn/128.11.1995. [PMID: 9808655]
  • D W Giraud, H D Martin, J A Driskell. Erythrocyte and plasma B-6 vitamer concentrations of long-term tobacco smokers, chewers, and nonusers. The American journal of clinical nutrition. 1995 Jul; 62(1):104-9. doi: 10.1093/ajcn/62.1.104. [PMID: 7598051]
  • J Zempleni, W Kübler. The utilization of intravenously infused pyridoxine in humans. Clinica chimica acta; international journal of clinical chemistry. 1994 Sep; 229(1-2):27-36. doi: 10.1016/0009-8981(94)90226-7. [PMID: 7988052]
  • H Tsuge, M Maeno, K Nagae, C Nohisa, T Hayakawa. Change in blood levels of vitamin B-6 derivatives in pregnant and lactating rats. Journal of nutritional science and vitaminology. 1994 Jun; 40(3):239-49. doi: 10.3177/jnsv.40.239. [PMID: 7965213]
  • S K Sharma, K Dakshinamurti. Determination of vitamin B6 vitamers and pyridoxic acid in biological samples. Journal of chromatography. 1992 Jul; 578(1):45-51. doi: 10.1016/0378-4347(92)80223-d. [PMID: 1400785]
  • B I Yang, D J Harris. Determination of pyridoxamine 5'-phosphate in human blood plasma. Analytical biochemistry. 1991 Nov; 199(1):18-24. doi: 10.1016/0003-2697(91)90263-s. [PMID: 1807157]
  • D Furth-Walker, D Leibman, A Smolen. Relationship between blood, liver and brain pyridoxal phosphate and pyridoxamine phosphate concentrations in mice. The Journal of nutrition. 1990 Nov; 120(11):1338-43. doi: 10.1093/jn/120.11.1338. [PMID: 2231022]
  • D Leibman, D Furth-Walker, T N Smolen, A Smolen. Pyridoxal 5'-phosphate and pyridoxamine 5'-phosphate concentrations in blood and tissues of mice fed ethanol-containing liquid diets. Alcohol (Fayetteville, N.Y.). 1990 Jan; 7(1):61-8. doi: 10.1016/0741-8329(90)90061-g. [PMID: 2310505]
  • J E Churchich. Reaction of pyridoxamine-5-P with pyrroloquinoline quinone (coenzyme PQQ). BioFactors (Oxford, England). 1989 Dec; 2(2):113-6. doi: . [PMID: 2560372]
  • D Furth-Walker, D Leibman, A Smolen. Changes in pyridoxal phosphate and pyridoxamine phosphate in blood, liver and brain in the pregnant mouse. The Journal of nutrition. 1989 May; 119(5):750-6. doi: 10.1093/jn/119.5.750. [PMID: 2723825]
  • H Van den Berg, J J Bogaards. Vitamin B-6 metabolism in the pregnant rat: effect of progesterone on the (re)distribution in maternal vitamin B-6 stores. The Journal of nutrition. 1987 Nov; 117(11):1866-74. doi: 10.1093/jn/117.11.1866. [PMID: 3681477]
  • M B Chuvykin, M P Pavlova. [Pyridoxal and pyridoxamine phosphate levels in the plasma and bone marrow of children with acute leukemia]. Pediatriia. 1987; ?(11):104-5. doi: NULL. [PMID: 3431993]
  • A Lui, L Lumeng, G R Aronoff, T K Li. Relationship between body store of vitamin B6 and plasma pyridoxal-P clearance: metabolic balance studies in humans. The Journal of laboratory and clinical medicine. 1985 Nov; 106(5):491-7. doi: NULL. [PMID: 4056565]
  • A Minelli, C Borri Voltattorni, P Grant, J M Basford, R A John. The reaction of pyridoxal phosphate with holoenzymes in the pyridoxamine phosphate form. Progress in clinical and biological research. 1984; 144A(?):289-94. doi: NULL. [PMID: 6374674]
  • B Shane. Vitamin B-6 metabolism and turnover in the ethanol-fed rat. The Journal of nutrition. 1982 Apr; 112(4):610-8. doi: 10.1093/jn/112.4.610. [PMID: 7200128]
  • I B Zavodnik, N I Stepuro. [Fluorescence study of pyridoxamine-5'-phosphate and pyridoxamine covalently bound to serum albumin]. Izvestiia Akademii nauk SSSR. Seriia biologicheskaia. 1981 Jul; ?(4):536-42. doi: NULL. [PMID: 6792248]
  • J T Vanderslice, C E Maire, G R Beecher. B6 vitamer analysis in human plasma by high performance liquid chromatography: a preliminary report. The American journal of clinical nutrition. 1981 May; 34(5):947-50. doi: 10.1093/ajcn/34.5.947. [PMID: 7234721]
  • M S Chauhan, K Dakshinamurti. Fluorometric assay of B6 vitamers in biological material. Clinica chimica acta; international journal of clinical chemistry. 1981 Jan; 109(2):159-67. doi: 10.1016/0009-8981(81)90330-2. [PMID: 7471494]
  • T Sakurai, M Abe, S Hori, M Matsuda. The effects of administration of semicarbazide and aminooxyacetic acid on B6 vitamer levels in subcellular fractions of mouse brain. Journal of nutritional science and vitaminology. 1981; 27(6):529-38. doi: 10.3177/jnsv.27.529. [PMID: 7334424]
  • L Lumeng, A Lui, T K Li. Plasma content of B6 vitamers and its relationship to hepatic vitamin B6 metabolism. The Journal of clinical investigation. 1980 Oct; 66(4):688-95. doi: 10.1172/jci109906. [PMID: 7419716]