Xanthylic acid (BioDeep_00000003533)

 

Secondary id: BioDeep_00000400267, BioDeep_00001868819

natural product human metabolite PANOMIX_OTCML-2023 Endogenous BioNovoGene_Lab2019


代谢物信息卡片


{[(2R,3S,4R,5R)-5-(2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

化学式: C10H13N4O9P (364.042)
中文名称: 黄嘌呤5'-磷酸, 5\'-黄苷酸
谱图信息: 最多检出来源 Homo sapiens(natural_products) 8.46%

分子结构信息

SMILES: C([C@@H]1[C@H]([C@H]([C@H](n2cnc3c2[nH]c(=O)[nH]c3=O)O1)O)O)OP(=O)(O)O
InChI: InChI=1S/C10H13N4O9P/c15-5-3(1-22-24(19,20)21)23-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H2,19,20,21)(H2,12,13,17,18)

描述信息

Xanthylic acid, also known as xmp or (9-D-ribosylxanthine)-5-phosphate, is a member of the class of compounds known as purine ribonucleoside monophosphates. Purine ribonucleoside monophosphates are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Xanthylic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Xanthylic acid can be found in a number of food items such as common grape, black-eyed pea, java plum, and wild rice, which makes xanthylic acid a potential biomarker for the consumption of these food products. Xanthylic acid exists in all living species, ranging from bacteria to humans. In humans, xanthylic acid is involved in several metabolic pathways, some of which include azathioprine action pathway, glutamate metabolism, mercaptopurine action pathway, and purine metabolism. Xanthylic acid is also involved in several metabolic disorders, some of which include purine nucleoside phosphorylase deficiency, succinic semialdehyde dehydrogenase deficiency, xanthine dehydrogenase deficiency (xanthinuria), and molybdenum cofactor deficiency. Xanthosine monophosphate is an intermediate in purine metabolism. It is a ribonucleoside monophosphate. It is formed from IMP via the action of IMP dehydrogenase, and it forms GMP via the action of GMP synthaseand is) also, XMP can be released from XTP by enzyme deoxyribonucleoside triphosphate pyrophosphohydrolase containing (d)XTPase activity .
Xanthylic acid is an important metabolic intermediate in the Purine Metabolism, and is a product or substrate of the enzymes Inosine monophosphate dehydrogenase (EC 1.1.1.205), Hypoxanthine phosphoribosyltransferase (EC 2.4.2.8), Xanthine phosphoribosyltransferase (EC 2.4.2.22), 5-Ribonucleotide phosphohydrolase (EC 3.1.3.5), Ap4A hydrolase (EC 3.6.1.17), Nucleoside-triphosphate diphosphatase (EC 3.6.1.19), Phosphoribosylamine-glycine ligase (EC 6.3.4.1), and glutamine amidotransferase (EC 6.3.5.2). (KEGG) Xanthylic acid can also be used in quantitative measurements of the Inosine monophosphate dehydrogenase enzyme activities in purine metabolism. This measurement is important for optimal thiopurine therapy for children with acute lymphoblastic leukaemia (ALL). (PMID: 16725387).
Acquisition and generation of the data is financially supported in part by CREST/JST.
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同义名列表

23 个代谢物同义名

{[(2R,3S,4R,5R)-5-(2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid; [(2R,3S,4R,5R)-5-(2,6-dioxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate; Xanthosine-5′-monophosphate disodium salt; Xanthosine monophosphate, 8-(14)C-labeled; (9-D-Ribosylxanthine)-5-phosphoric acid; (9-D-Ribosylxanthine)-5-phosphate; Xanthosine monophosphoric acid; 5-Xanthonylate monophosphate; Xanthosine 5-phosphoric acid; Xanthosine 5’-monophosphate; Xanthosine-5-monophosphate; Xanthosine 5-monophosphate; XANTHOSINE-MONOPHOSPHATE; Xanthosine monophosphate; Xanthosine 5’-phosphate; Xanthosine-5-phosphate; Xanthosine 5-phosphate; Xanthosine-5-P; Xanthylic acid; Xanthylate; XMP; Xanthosine 5'-phosphate(XMP); Xanthosine 5'-phosphate



数据库引用编号

32 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(7)

PlantCyc(0)

代谢反应

337 个相关的代谢反应过程信息。

Reactome(18)

BioCyc(8)

WikiPathways(1)

Plant Reactome(234)

INOH(2)

PlantCyc(0)

COVID-19 Disease Map(1)

PathBank(73)

PharmGKB(0)

3 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 8 ADA, EMP2, G6PD, HPRT1, ITPA, NT5C2, TPMT, XDH
Peripheral membrane protein 3 ADA, G6PD, HSD17B6
Endoplasmic reticulum membrane 2 CD4, TKT
Nucleus 1 EMP2
cytosol 13 ADA, ADSL, ATIC, G6PD, GLS, GMPR, GMPS, HPRT1, ITPA, NT5C2, TKT, TPMT, XDH
nuclear body 1 TKT
nucleoplasm 3 CD2, ITPA, TKT
Cell membrane 5 ADA, CD2, CD4, EMP2, TKT
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 1 EMP2
Golgi apparatus membrane 1 EMP2
Synapse 1 GLS
cell junction 1 ADA
cell surface 4 ADA, CD2, EMP2, MSLN
Golgi apparatus 3 CD2, EMP2, MSLN
Golgi membrane 1 EMP2
Cytoplasm, cytosol 5 ATIC, G6PD, GLS, GMPS, NT5C2
Lysosome 1 ADA
plasma membrane 7 ADA, ATIC, CD2, CD4, EMP2, MSLN, TKT
Membrane 5 ADA, ATIC, EMP2, G6PD, MSLN
apical plasma membrane 2 EMP2, TKT
extracellular exosome 4 ATIC, G6PD, HPRT1, TKT
Lumenal side 1 HSD17B6
endoplasmic reticulum 1 HSD17B6
extracellular space 1 XDH
perinuclear region of cytoplasm 1 EMP2
mitochondrion 1 GLS
protein-containing complex 2 ADSL, CD2
intracellular membrane-bounded organelle 3 G6PD, HSD17B6, ITPA
Microsome membrane 1 HSD17B6
Single-pass type I membrane protein 3 CD2, CD4, TKT
extracellular region 2 CD2, MSLN
cytoplasmic side of plasma membrane 2 CD2, G6PD
mitochondrial matrix 1 GLS
Extracellular side 1 ADA
Cytoplasmic vesicle lumen 1 ADA
anchoring junction 1 ADA
centriolar satellite 1 G6PD
external side of plasma membrane 3 ADA, CD2, CD4
actin cytoskeleton 1 TKT
cytoplasmic vesicle 1 EMP2
Early endosome 1 CD4
apical part of cell 1 EMP2
cell-cell junction 1 CD2
vesicle 1 TKT
Apical cell membrane 1 EMP2
Cytoplasm, perinuclear region 1 EMP2
Membrane raft 2 CD4, EMP2
focal adhesion 1 TKT
Peroxisome 2 TKT, XDH
sarcoplasmic reticulum 1 XDH
receptor complex 1 TKT
[Isoform 1]: Mitochondrion 1 GLS
side of membrane 1 MSLN
endoplasmic reticulum lumen 2 CD4, MSLN
clathrin-coated endocytic vesicle membrane 1 CD4
[Isoform 3]: Mitochondrion 1 GLS
[Glutaminase kidney isoform, mitochondrial 68 kDa chain]: Mitochondrion matrix 1 GLS
[Glutaminase kidney isoform, mitochondrial 65 kDa chain]: Mitochondrion matrix 1 GLS
T cell receptor complex 1 CD4
GMP reductase complex 1 GMPR


文献列表

  • Katharina J Heinemann, Sun-Young Yang, Henryk Straube, Nieves Medina-Escobar, Marina Varbanova-Herde, Marco Herde, Sangkee Rhee, Claus-Peter Witte. Initiation of cytosolic plant purine nucleotide catabolism involves a monospecific xanthosine monophosphate phosphatase. Nature communications. 2021 11; 12(1):6846. doi: 10.1038/s41467-021-27152-4. [PMID: 34824243]
  • Yasuaki Mino, Takafumi Naito, Kumiko Shimoyama, Noriyoshi Ogawa, Junichi Kawakami. Mycophenolic acid exposure and complement fraction C3 influence inosine 5'-monophosphate dehydrogenase activity in systemic lupus erythematosus. Annals of clinical biochemistry. 2017 Jul; 54(4):490-494. doi: 10.1177/0004563216667753. [PMID: 27538768]
  • T Maiguma, T Yosida, K Otsubo, Y Okabe, A Sugitani, M Tanaka, R Oishi, D Teshima. Evaluation of inosin-5'-monophosphate dehydrogenase activity during maintenance therapy with tacrolimus. Journal of clinical pharmacy and therapeutics. 2010 Feb; 35(1):79-85. doi: 10.1111/j.1365-2710.2009.01072.x. [PMID: 20175815]