Barbituric acid (BioDeep_00000004486)

 

Secondary id: BioDeep_00001868375

human metabolite Endogenous


代谢物信息卡片


2,4,6(1H,3H,5H)-Pyrimidinetrione (acd/name 4.0)

化学式: C4H4N2O3 (128.0222)
中文名称: 巴比妥酸
谱图信息: 最多检出来源 Homo sapiens(plant) 9.57%

分子结构信息

SMILES: C1C(=O)NC(=O)NC1=O
InChI: InChI=1S/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)

描述信息

Barbituric acid or malonylurea or 6-hydroxyuracil is an organic compound based on a pyrimidine heterocyclic skeleton. It is an odorless powder soluble in water. Barbituric acid is the parent compound of barbiturate drugs, although barbituric acid itself is not pharmacologically active. The compound was discovered by the German chemist Adolf von Baeyer on December 4, 1864, the feast of Saint Barbara (who gave the compound its namesake), by combining urea and malonic acid in a condensation reaction. Malonic acid has since been replaced by diethyl malonate, as using the ester avoids the problem of having to deal with the acidity of the carboxylic acid and its unreactive carboxylate.

同义名列表

25 个代谢物同义名

2,4,6(1H,3H,5H)-Pyrimidinetrione (acd/name 4.0); 4,6-dihydroxy-2,5-dihydropyrimidin-2-one; N,N-(1,3-dioxo-1,3-propanediyl)-urea; NN-(1,3-Dioxo-1,3-propanediyl)-urea; 2,4,6-(1H,3H,5H)-Pyrimidinetrione; Pyrimidine-2,4,6(1H,3H,5H)-trione; 2,4,6(1H,3H,5H)-Pyrimidinetrione; 2,4,6-Pyrimidinetrione(1H,3H,5H); Barbituric acid, monosodium salt; 2,4,6-Trioxohexahydropyrimidine; 2,4,6-Trihydroxypyrimidine; 2,4,6-Pyrimidinetriol; sodium barbiturate; Pyrimidinetrione; Malonylharnstoff; BARBITURIC ACID; 6-HYDROXYURACIL; Barbitursaeure; Barbitursaure; Barbitic acid; Barbiturate; Malonylurea; Barbitate; Barbiturate; Barbituric acid



数据库引用编号

15 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

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 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 7 ALB, AXIN2, CA1, PMP2, POMC, PPARG, PTGS2
Peripheral membrane protein 1 PTGS2
Endosome membrane 1 CLCN5
Endoplasmic reticulum membrane 1 PTGS2
Nucleus 5 ALB, AXIN2, PMP2, PPARG, TCEA1
cytosol 8 ALB, AXIN2, CA1, CLCN5, GPT, PMP2, PPARG, PRKCQ
centrosome 2 ALB, AXIN2
nucleoplasm 2 PPARG, TCEA1
RNA polymerase II transcription regulator complex 1 PPARG
Cell membrane 3 CLCN5, GRID1, OPRD1
Multi-pass membrane protein 4 CACNA1I, CLCN5, GRID1, OPRD1
Golgi apparatus membrane 1 CLCN5
Synapse 1 TAC1
glutamatergic synapse 1 GRID1
Golgi apparatus 2 ALB, CLCN5
Golgi membrane 2 CLCN5, INS
lysosomal membrane 2 CLCN5, GAA
neuronal cell body 1 TAC1
presynaptic membrane 1 OPRD1
synaptic vesicle 1 CLCN5
Lysosome 1 GAA
plasma membrane 9 AXIN2, CACNA1I, CLCN5, GAA, GCG, GRID1, KNG1, OPRD1, PRKCQ
synaptic vesicle membrane 1 OPRD1
Membrane 4 CACNA1I, CLCN5, GAA, OPRD1
axon 1 TAC1
caveola 1 PTGS2
extracellular exosome 7 ALB, CA1, GAA, GPT, GRID1, KNG1, PMP2
Lysosome membrane 1 GAA
endoplasmic reticulum 2 ALB, PTGS2
extracellular space 6 ALB, GCG, INS, KNG1, POMC, TAC1
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 1 PPARG
protein-containing complex 2 ALB, PTGS2
intracellular membrane-bounded organelle 2 GAA, PPARG
Microsome membrane 1 PTGS2
Secreted 6 ALB, GAA, GCG, INS, POMC, TRH
extracellular region 8 ALB, GAA, GCG, INS, KNG1, POMC, TAC1, TRH
anchoring junction 1 ALB
centriolar satellite 1 PRKCQ
beta-catenin destruction complex 1 AXIN2
nucleolus 1 TCEA1
Early endosome 1 CLCN5
apical part of cell 1 CLCN5
postsynaptic membrane 1 GRID1
GABA-ergic synapse 1 GRID1
collagen-containing extracellular matrix 1 KNG1
secretory granule 2 POMC, TRH
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Postsynaptic cell membrane 1 GRID1
receptor complex 1 PPARG
neuron projection 2 OPRD1, PTGS2
ciliary basal body 1 ALB
chromatin 1 PPARG
centriole 1 ALB
Secreted, extracellular space 1 KNG1
spindle pole 1 ALB
blood microparticle 2 ALB, KNG1
endosome lumen 1 INS
tertiary granule membrane 1 GAA
myelin sheath 1 PMP2
secretory granule lumen 3 GCG, INS, POMC
Golgi lumen 1 INS
endoplasmic reticulum lumen 5 ALB, GCG, INS, KNG1, PTGS2
transcription factor TFIID complex 1 TCEA1
platelet alpha granule lumen 2 ALB, KNG1
axon terminus 1 OPRD1
voltage-gated calcium channel complex 1 CACNA1I
transport vesicle 1 INS
azurophil granule membrane 1 GAA
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
postsynaptic density membrane 2 GRID1, OPRD1
immunological synapse 1 PRKCQ
neuronal dense core vesicle 1 OPRD1
aggresome 1 PRKCQ
ficolin-1-rich granule membrane 1 GAA
dendrite membrane 1 OPRD1
[Glucagon-like peptide 1]: Secreted 1 GCG
autolysosome lumen 1 GAA
spine apparatus 1 OPRD1
ciliary transition fiber 1 ALB


文献列表

  • Seon-Mi Seo, Hyo-Rim Lee, Ji-Eun Lee, Yong-Chul Jeong, Hyung-Wook Kwon, Joon-Kwan Moon, Mark G Moloney, Il-Kwon Park. Larvicidal and Nematicidal Activities of 3-Acylbarbituric Acid Analogues against Asian Tiger Mosquito, Aedes albopictus, and Pine Wood Nematode, Bursaphelenchus xylophilus. Molecules (Basel, Switzerland). 2017 Jul; 22(7):. doi: 10.3390/molecules22071196. [PMID: 28714917]
  • Joshua E Raizman, Penny D Colbourne, Donald F LeGatt, Darren Chow, Lyric Rudolph. Glistening Urine Sample from a Patient with Delirium. Clinical chemistry. 2017 07; 63(7):1306-1307. doi: 10.1373/clinchem.2017.272377. [PMID: 28659400]
  • Veysel T Yilmaz, Ceyda Icsel, Feruza Suyunova, Muhittin Aygun, Nazlihan Aztopal, Engin Ulukaya. Ni(ii)/Cu(ii)/Zn(ii) 5,5-diethylbarbiturate complexes with 1,10-phenanthroline and 2,2'-dipyridylamine: synthesis, structures, DNA/BSA binding, nuclease activity, molecular docking, cellular uptake, cytotoxicity and the mode of cell death. Dalton transactions (Cambridge, England : 2003). 2016 Jun; 45(25):10466-79. doi: 10.1039/c6dt01726f. [PMID: 27263797]
  • Yong-Chul Jeong, Mark G Moloney. Antibacterial barbituric acid analogues inspired from natural 3-acyltetramic acids; synthesis, tautomerism and structure and physicochemical property-antibacterial activity relationships. Molecules (Basel, Switzerland). 2015 Feb; 20(3):3582-627. doi: 10.3390/molecules20033582. [PMID: 25710842]
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  • Sergio Hidalgo-Figueroa, Juan J Ramírez-Espinosa, Samuel Estrada-Soto, Julio C Almanza-Pérez, Rubén Román-Ramos, Francisco J Alarcón-Aguilar, Jesús V Hernández-Rosado, Hermenegilda Moreno-Díaz, Daniel Díaz-Coutiño, Gabriel Navarrete-Vázquez. Discovery of thiazolidine-2,4-dione/biphenylcarbonitrile hybrid as dual PPAR α/γ modulator with antidiabetic effect: in vitro, in silico and in vivo approaches. Chemical biology & drug design. 2013 Apr; 81(4):474-83. doi: 10.1111/cbdd.12102. [PMID: 23289972]
  • Igor Botello, Francesc Borrull, Marta Calull, Carme Aguilar. Electrokinetic supercharging in CE for the separation and preconcentration of barbiturate drugs in urine samples. Journal of separation science. 2013 Feb; 36(3):524-31. doi: 10.1002/jssc.201200690. [PMID: 23303599]
  • Peter Ballard, Malcolm Rowland. Correction for nonspecific binding to various components of ultrafiltration apparatus and impact on estimating in vivo rat clearance for a congeneric series of 5-ethyl, 5-n-alkyl barbituric acids. Drug metabolism and disposition: the biological fate of chemicals. 2011 Dec; 39(12):2165-8. doi: 10.1124/dmd.111.040683. [PMID: 21880830]
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  • Hao Zheng, Shilin Li, Liang Ma, Ling Cheng, Chongyang Deng, Zhizhi Chen, Caifeng Xie, Mingli Xiang, Wei Jiang, Lijuan Chen. A novel agonist of PPAR-γ based on barbituric acid alleviates the development of non-alcoholic fatty liver disease by regulating adipocytokine expression and preventing insulin resistance. European journal of pharmacology. 2011 Jun; 659(2-3):244-51. doi: 10.1016/j.ejphar.2011.03.033. [PMID: 21463618]
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  • Amit Kumar Patel, Piyush Sindhu Sharma, Bhim Bali Prasad. Voltammetric sensor for barbituric acid based on a sol-gel derivated molecularly imprinted polymer brush grafted to graphite electrode. International journal of pharmaceutics. 2009 Apr; 371(1-2):47-55. doi: 10.1016/j.ijpharm.2008.12.016. [PMID: 19135515]
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