7,8-Dihydropteroic acid (BioDeep_00000004519)

 

Secondary id: BioDeep_00001868979

human metabolite Endogenous


代谢物信息卡片


4-[[(2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-benzoic acid

化学式: C14H14N6O3 (314.1127334)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(natural_products) 6.95%

分子结构信息

SMILES: C1C(=NC2=C(N1)N=C(NC2=O)N)CNC3=CC=C(C=C3)C(=O)O
InChI: InChI=1S/C14H14N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,16H,5-6H2,(H,22,23)(H4,15,17,19,20,21)

描述信息

In the mammalian host, dihydrofolate biosynthesis occurs via the reduction of folic acid, whereas in plasmodia (e.g. Plasmodium berghei, a malaria parasite) the biosynthesis of 7,8-dihydropteroate, an intermediate product in dihydrofolate synthesis, occurs via the enzymic catalysis of the reaction of 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine pyrophosphate with p-aminobenzoate. Malaria parasites synthesize their folate cofactors de novo and the antimalarial action of sulfonamides is due to their inhibiting the plasmodial dihydropteroate synthesis. The enzymes 6-hydroxymethylpterin pyrophosphokinase (EC 2.7.6.3, HPPK) and dihydropteroate synthase (EC 2.5.1.15, DHPS) catalyze sequential steps in folate biosynthesis. They are present in microorganisms but absent in mammals and therefore are especially suitable targets for antimicrobials. Sulfa drugs (sulfonamides and sulfones) currently are used as antimicrobials targeting DHPS, although resistance to these drugs is increasing. An NADPH-coupled microplate photometric assay could be used for rapid screening of chemical libraries for novel inhibitors of folate biosynthesis as the first step in developing new antimicrobial drugs targeting the folate biosynthetic pathway; in the microplate, the product of the DHPS reaction, 7,8-dihydropteroic acid, is reduced to tetrahydropteroate by excess dihydrofolate reductase (DHFR) using the cofactor NADPH (PMID: 17134675, 4354403, 3546688).
7,8-dihydropteroic acid, also known as dihydropteroinsaeure or h2pte, belongs to pterins and derivatives class of compounds. Those are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one. 7,8-dihydropteroic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 7,8-dihydropteroic acid can be synthesized from pteroic acid. 7,8-dihydropteroic acid can also be synthesized into 2-hydroxy-7,8-dihydropteroic acid. 7,8-dihydropteroic acid can be found in a number of food items such as rice, towel gourd, cauliflower, and silver linden, which makes 7,8-dihydropteroic acid a potential biomarker for the consumption of these food products. 7,8-dihydropteroic acid exists in all living species, ranging from bacteria to humans. In humans, 7,8-dihydropteroic acid is involved in the pterine biosynthesis.

同义名列表

16 个代谢物同义名

4-[[(2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-benzoic acid; 4-[[(2-Amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-benzoic acid; 4-{[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoic acid; 4-(((2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoic acid; p-[[(2-Amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]-benzoic acid; 4-[[(2-Amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-benzoate; 4-[[(2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-benzoate; 4-(((2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoate; p-[[(2-Amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]-benzoate; 7,8-Dihydropteroic acid; Dihydropteroinsaeure; 7,8-Dihydropteroate; Dihydropteroic acid; dihydropteroate; Dihydropterate; H2Pte



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(3)

PlantCyc(0)

代谢反应

335 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(8)

WikiPathways(1)

  • Folate biosynthesis: (2-amino-4-hydroxy-7,8-dihydropteridin- 6-yl)methyl trihydrogen diphosphate ⟶ 7,8-dihydropteroic acid

Plant Reactome(320)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(5)

PharmGKB(0)

2 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

  • Tzu-Chieh Hung, Kuen-Bao Chen, Wen-Yuan Lee, Calvin Yu-Chian Chen. The inhibition of folylpolyglutamate synthetase (folC) in the prevention of drug resistance in Mycobacterium tuberculosis by traditional Chinese medicine. BioMed research international. 2014; 2014(?):635152. doi: 10.1155/2014/635152. [PMID: 25050369]
  • J Enrique Salcedo-Sora, Edwin Ochong, Susan Beveridge, David Johnson, Alexis Nzila, Giancarlo A Biagini, Paul A Stocks, Paul M O'Neill, Sanjeev Krishna, Patrick G Bray, Stephen A Ward. The molecular basis of folate salvage in Plasmodium falciparum: characterization of two folate transporters. The Journal of biological chemistry. 2011 Dec; 286(52):44659-68. doi: 10.1074/jbc.m111.286054. [PMID: 21998306]
  • Maddalena Rossi, Alberto Amaretti, Stefano Raimondi. Folate production by probiotic bacteria. Nutrients. 2011 01; 3(1):118-34. doi: 10.3390/nu3010118. [PMID: 22254078]
  • Paul Francis Morris, Laura Rose Schlosser, Katherine Diane Onasch, Tom Wittenschlaeger, Ryan Austin, Nicholas Provart. Multiple horizontal gene transfer events and domain fusions have created novel regulatory and metabolic networks in the oomycete genome. PloS one. 2009 Jul; 4(7):e6133. doi: 10.1371/journal.pone.0006133. [PMID: 19582169]
  • Valérie de Crécy-Lagard, Basma El Yacoubi, Rocío Díaz de la Garza, Alexandre Noiriel, Andrew D Hanson. Comparative genomics of bacterial and plant folate synthesis and salvage: predictions and validations. BMC genomics. 2007 Jul; 8(?):245. doi: 10.1186/1471-2164-8-245. [PMID: 17645794]
  • Ping Wang, Qi Wang, Paul F G Sims, John E Hyde. Characterisation of exogenous folate transport in Plasmodium falciparum. Molecular and biochemical parasitology. 2007 Jul; 154(1):40-51. doi: 10.1016/j.molbiopara.2007.04.002. [PMID: 17509698]
  • Ralf Stracke, Hirofumi Ishihara, Gunnar Huep, Aiko Barsch, Frank Mehrtens, Karsten Niehaus, Bernd Weisshaar. Differential regulation of closely related R2R3-MYB transcription factors controls flavonol accumulation in different parts of the Arabidopsis thaliana seedling. The Plant journal : for cell and molecular biology. 2007 May; 50(4):660-77. doi: 10.1111/j.1365-313x.2007.03078.x. [PMID: 17419845]
  • Sungano Mharakurwa, Christopher Simoloka, Philip E Thuma, Clive J Shiff, David J Sullivan. PCR detection of Plasmodium falciparum in human urine and saliva samples. Malaria journal. 2006 Nov; 5(?):103. doi: 10.1186/1475-2875-5-103. [PMID: 17092335]
  • Samuel Jabrin, Stéphane Ravanel, Bernadette Gambonnet, Roland Douce, Fabrice Rébeillé. One-carbon metabolism in plants. Regulation of tetrahydrofolate synthesis during germination and seedling development. Plant physiology. 2003 Mar; 131(3):1431-9. doi: 10.1104/pp.016915. [PMID: 12644692]
  • Jean-Marie Mouillon, Stéphane Ravanel, Roland Douce, Fabrice Rébeillé. Folate synthesis in higher-plant mitochondria: coupling between the dihydropterin pyrophosphokinase and the dihydropteroate synthase activities. The Biochemical journal. 2002 Apr; 363(Pt 2):313-9. doi: 10.1042/0264-6021:3630313. [PMID: 11931659]
  • L M Iyer, L Aravind, P Bork, K Hofmann, A R Mushegian, I B Zhulin, E V Koonin. Quod erat demonstrandum? The mystery of experimental validation of apparently erroneous computational analyses of protein sequences. Genome biology. 2001; 2(12):RESEARCH0051. doi: 10.1186/gb-2001-2-12-research0051. [PMID: 11790254]
  • F Rébeillé, D Macherel, J M Mouillon, J Garin, R Douce. Folate biosynthesis in higher plants: purification and molecular cloning of a bifunctional 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase/7,8-dihydropteroate synthase localized in mitochondria. The EMBO journal. 1997 Mar; 16(5):947-57. doi: 10.1093/emboj/16.5.947. [PMID: 9118956]
  • M K Samson, R L Stephens, S Rivkin, M Opipari, T Maloney, C W Groppe, R Fisher. Vinblastine, bleomycin, and cis-dichlorodiammineplatinum(II) in disseminated testicular cancer: preliminary report of a Southwest Oncology Group Study. Cancer treatment reports. 1979 Sep; 63(9-10):1663-7. doi: . [PMID: 91435]
  • J K Seydel, W Butte. P-Aminobenzoic acid derivatives. Mode of action and structure-activity relationships in a cell-free system (Escherichia coli). Journal of medicinal chemistry. 1977 Mar; 20(3):439-47. doi: 10.1021/jm00213a023. [PMID: 321779]