Guanosine monophosphate (BioDeep_00000003009)

 

Secondary id: BioDeep_00000398718, BioDeep_00002052733, BioDeep_00002053054

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


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

化学式: C10H14N5O8P (363.05799740000003)
中文名称: 鸟苷酸, 鸟苷-磷酸, 一磷酸鸟苷
谱图信息: 最多检出来源 Homo sapiens(blood) 0.03%

Reviewed

Last reviewed on 2024-06-29.

Cite this Page

Guanosine monophosphate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/guanosine_monophosphate (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000003009). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C([C@@H]1[C@H]([C@H]([C@H](n2cnc3c2nc(N)[nH]c3=O)O1)O)O)OP(=O)(O)O
InChI: InChI=1S/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1

描述信息

Guanosine monophosphate (GMP), also known as 5′-guanidylic acid or guanylic acid (conjugate base guanylate), is a nucleotide that is used as a monomer in RNA. It is an ester of phosphoric acid with the nucleoside guanosine. GMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase guanine; hence it is a ribonucleoside monophosphate. Guanosine monophosphate is commercially produced by microbial fermentation. Guanosine monophosphate, also known as guanylic acid or 5-GMP, belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature. Guanosine monophosphate exists in all living species, ranging from bacteria to humans. Within humans, guanosine monophosphate participates in a number of enzymatic reactions. In particular, guanosine triphosphate and guanosine monophosphate can be biosynthesized from diguanosine tetraphosphate through its interaction with the enzyme bis(5-nucleosyl)-tetraphosphatase [asymmetrical]. In addition, guanosine monophosphate can be biosynthesized from guanosine diphosphate; which is mediated by the enzyme ectonucleoside triphosphate diphosphohydrolase 5. In humans, guanosine monophosphate is involved in the metabolic disorder called the lesch-nyhan syndrome (lns) pathway. Outside of the human body, guanosine monophosphate has been detected, but not quantified in several different foods, such as common cabbages, tea, winter squash, spearmints, and sugar apples.
Guanosine-5-monophosphate, also known as 5-gmp or guanylic acid, 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. Guanosine-5-monophosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Guanosine-5-monophosphate can be found in a number of food items such as mustard spinach, swiss chard, watercress, and colorado pinyon, which makes guanosine-5-monophosphate a potential biomarker for the consumption of these food products. Guanosine-5-monophosphate can be found primarily in blood and saliva, as well as throughout most human tissues. Guanosine-5-monophosphate exists in all living species, ranging from bacteria to humans. In humans, guanosine-5-monophosphate is involved in several metabolic pathways, some of which include clarithromycin action pathway, erythromycin action pathway, minocycline action pathway, and tetracycline action pathway. Guanosine-5-monophosphate is also involved in several metabolic disorders, some of which include gout or kelley-seegmiller syndrome, xanthine dehydrogenase deficiency (xanthinuria), aICA-Ribosiduria, and molybdenum cofactor deficiency.

Guanosine monophosphate is known as E number reference E626.[7] In the form of its salts, such as disodium guanylate (E627), dipotassium guanylate (E628) and calcium guanylate (E629), are food additives used as flavor enhancers to provide the umami taste.[7] It is often used in synergy with disodium inosinate; the combination is known as disodium 5′-ribonucleotides. Disodium guanylate is often found in instant noodles, potato chips and snacks, savoury rice, tinned vegetables, cured meats, and packet soup.

As it is a fairly expensive additive, it is usually not used independently of glutamic acid or monosodium glutamate (MSG), which also contribute umami. If inosinate and guanylate salts are present in a list of ingredients but MSG does not appear to be, the glutamic acid is likely provided as part of another ingredient, such as a processed soy protein complex (hydrolyzed soy protein), autolyzed yeast, or soy sauce.
5'-Guanylic acid (5'-GMP) is involved in several metabolic disorders, including the AICA-ribosiduria pathway, adenosine deaminase deficiency, adenine phosphoribosyltransferase deficiency (aprt), and the 2-hydroxyglutric aciduria pathway.
5'-Guanylic acid (5'-GMP) is involved in several metabolic disorders, including the AICA-ribosiduria pathway, adenosine deaminase deficiency, adenine phosphoribosyltransferase deficiency (aprt), and the 2-hydroxyglutric aciduria pathway.

同义名列表

32 个代谢物同义名

{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid; Guanosine-5-monophosphate disodium salt hydrate from Yeast; Guanidylic acid (guanosine monophosphate); Guanosine 5-monophosphoric acid; Guanosine-5-monophosphoric acid; Guanosine monophosphoric acid; Guanosine 5-phosphoric acid; 5-monoPhosphate, guanosine; Guanosine 5-monophosphate; Guanosine 5 monophosphate; Guanosine-5-monophosphate; monoPhosphate, guanosine; Guanidine monophosphate; Guanosine monophosphate; Guanosine 5-phosphorate; Guanosine-5-phosphate; Guanosine 5-phosphate; Guanosine-phosphate; Acid, 5-guanylic; 5-Guanylic acid; 5 Guanylic acid; Acid, guanylic; Guanylic acid; Guanylate; 5-GMP; e 626; GMP; PG; Guanosine monophosphate (GMP); 5'-GMP; 5'-guanosine monophosphate; 5'-Guanylic acid



数据库引用编号

50 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(9)

PlantCyc(6)

代谢反应

1126 个相关的代谢反应过程信息。

Reactome(37)

BioCyc(10)

WikiPathways(2)

Plant Reactome(0)

INOH(4)

PlantCyc(998)

COVID-19 Disease Map(2)

PathBank(73)

PharmGKB(0)

30 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

  • Xia Li, Wenfang Yin, Junjie Desmond Lin, Yong Zhang, Quan Guo, Gerun Wang, Xiayu Chen, Binbin Cui, Mingfang Wang, Min Chen, Peng Li, Ya-Wen He, Wei Qian, Haibin Luo, Lian-Hui Zhang, Xue-Wei Liu, Shihao Song, Yinyue Deng. Regulation of the physiology and virulence of Ralstonia solanacearum by the second messenger 2',3'-cyclic guanosine monophosphate. Nature communications. 2023 Nov; 14(1):7654. doi: 10.1038/s41467-023-43461-2. [PMID: 37996405]
  • Gulnaz Bibi, Iqra Shafique, Sartaj Ali, Raza Ahmad, Mohammad Maroof Shah, Tatheer Alam Naqvi, Iftikhar Zeb, Frans J M Maathuis, Jamshaid Hussain. Cyclic guanosine monophosphate improves salt tolerance in Solanum lycopersicum. Journal of plant research. 2023 Aug; ?(?):. doi: 10.1007/s10265-023-01487-z. [PMID: 37610631]
  • Maria Godoy-Gallardo, Maria Merino-Gómez, Miguel A Mateos-Timoneda, Ulrich Eckhard, F Javier Gil, Roman A Perez. Advanced Binary Guanosine and Guanosine 5'-Monophosphate Cell-Laden Hydrogels for Soft Tissue Reconstruction by 3D Bioprinting. ACS applied materials & interfaces. 2023 Jun; ?(?):. doi: 10.1021/acsami.2c23277. [PMID: 37319328]
  • Liqian Chen, Xinghong Zhou, Yijian Deng, Ying Yang, Xiaohu Chen, Qinghong Chen, Yanyan Liu, Xiuqiong Fu, Hiu Yee Kwan, Yanting You, Wen Jin, Xiaoshan Zhao. Zhenwu decoction ameliorates cardiac hypertrophy through activating sGC (soluble guanylate cyclase) - cGMP (cyclic guanosine monophosphate) - PKG (protein kinase G) pathway. Journal of ethnopharmacology. 2023 Jan; 300(?):115705. doi: 10.1016/j.jep.2022.115705. [PMID: 36099983]
  • Othman K Qadir, Chris J Seal, Ammar W Ashor, Michele Tassotti, Pedro Mena, Daniele Del Rio, Mario Siervo, Kirsten Brandt. Double-blind controlled dietary cross-over intervention with differentially fertilised intact lettuce leaves shows acute reduction in blood pressure in young adults, associated with faster uptake of nitrate than of phenolics. European journal of nutrition. 2022 Dec; 61(8):4191-4203. doi: 10.1007/s00394-022-02961-5. [PMID: 35871120]
  • Lu Wang, Yuwei Zhang, Yafeng Ren, Xue Yang, Haijing Ben, Fulan Zhao, Sijin Yang, Li Wang, Jie Qing. Pharmacological targeting of cGAS/STING-YAP axis suppresses pathological angiogenesis and ameliorates organ fibrosis. European journal of pharmacology. 2022 Oct; 932(?):175241. doi: 10.1016/j.ejphar.2022.175241. [PMID: 36058291]
  • Quan Guo, Binbin Cui, Mingfang Wang, Xia Li, Huihui Tan, Shihao Song, Jianuan Zhou, Lian-Hui Zhang, Yinyue Deng. Elongation factor P modulates Acinetobacter baumannii physiology and virulence as a cyclic dimeric guanosine monophosphate effector. Proceedings of the National Academy of Sciences of the United States of America. 2022 10; 119(41):e2209838119. doi: 10.1073/pnas.2209838119. [PMID: 36191190]
  • Patrícia Regina Terço Leite, Bethânia Rosa Lorençone, Karyne Garcia Tafarelo Moreno, Katiana Simões Lopes, Aline Aparecida Macedo Marques, Clara Soligo Fortini, Rhanany Alan Calloi Palozi, Mariana Dalmagro, Cândida Aparecida Leite Kassuya, Ariany Carvalho Dos Santos, Marcos José Salvador, Arquimedes Gasparotto Junior. The NO-cGMP-K+ Channel Pathway Participates in Diuretic and Cardioprotective Effects of Blutaparon portulacoides in Spontaneously Hypertensive Rats. Planta medica. 2022 Oct; 88(13):1152-1162. doi: 10.1055/a-1690-3566. [PMID: 35299274]
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  • Nina A Dzhoyashvili, Seethalakshmi R Iyer, Horng H Chen, John C Burnett. MANP (M-Atrial Natriuretic Peptide) Reduces Blood Pressure and Furosemide-Induced Increase in Aldosterone in Hypertension. Hypertension (Dallas, Tex. : 1979). 2022 04; 79(4):750-760. doi: 10.1161/hypertensionaha.121.18837. [PMID: 35045724]
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  • Shun Cao, Xianghui Li, Ting Feng, Yaqing Li, Hongwei Ding, Lin Xie, Quanhong Yang. Hirudin promotes proliferation and osteogenic differentiation of HBMSCs via activation of cyclic guanosine monophosphate (cGMP)/protein kinase-G (PKG) signaling pathway. Bioengineered. 2022 03; 13(3):6061-6069. doi: 10.1080/21655979.2021.2008697. [PMID: 34898364]
  • Haifeng Sha, Bing Yan. One step functional assembly of guanosine monophosphate and terbium ion on metal organic frameworks for determination of alkaline phosphatase activity. Analytica chimica acta. 2022 Feb; 1194(?):339434. doi: 10.1016/j.aca.2022.339434. [PMID: 35063155]
  • Ashleigh Shannon, Véronique Fattorini, Bhawna Sama, Barbara Selisko, Mikael Feracci, Camille Falcou, Pierre Gauffre, Priscila El Kazzi, Adrien Delpal, Etienne Decroly, Karine Alvarez, Cécilia Eydoux, Jean-Claude Guillemot, Adel Moussa, Steven S Good, Paolo La Colla, Kai Lin, Jean-Pierre Sommadossi, Yingxiao Zhu, Xiaodong Yan, Hui Shi, François Ferron, Bruno Canard. A dual mechanism of action of AT-527 against SARS-CoV-2 polymerase. Nature communications. 2022 02; 13(1):621. doi: 10.1038/s41467-022-28113-1. [PMID: 35110538]
  • Chidinma Promise Anyachor, Francis David Sikoki. Assessing the nutritional and biochemical composition of the African catfish (Clarias Gariepinus) exposed to the antifoam polydimethylsiloxane. Environmental science and pollution research international. 2022 Jan; 29(4):5923-5930. doi: 10.1007/s11356-021-15871-6. [PMID: 34435288]
  • Senthil Selvaraj, Brian L Claggett, Milton Packer, Faiez Zannad, Inder S Anand, Burkert Pieske, Ziqiang Zhao, Victor C Shi, Martin P Lefkowitz, John J V McMurray, Scott D Solomon. Effects of Sacubitril/Valsartan on Serum Lipids in Heart Failure With Preserved Ejection Fraction. Journal of the American Heart Association. 2021 09; 10(17):e022069. doi: 10.1161/jaha.121.022069. [PMID: 33998278]
  • Mateusz Kwiatkowski, Aloysius Wong, Anna Kozakiewicz-Piekarz, Christoph Gehring, Krzysztof Jaworski. In Search of Monocot Phosphodiesterases: Identification of a Calmodulin Stimulated Phosphodiesterase from Brachypodium distachyon. International journal of molecular sciences. 2021 Sep; 22(17):. doi: 10.3390/ijms22179654. [PMID: 34502563]
  • Dejan Lazić, Andreas Scheurer, Dušan Ćoćić, Jelena Milovanović, Aleksandar Arsenijević, Bojana Stojanović, Nebojša Arsenijević, Marija Milovanović, Ana Rilak Simović. A new bis-pyrazolylpyridine ruthenium(III) complex as a potential anticancer drug: in vitro and in vivo activity in murine colon cancer. Dalton transactions (Cambridge, England : 2003). 2021 Jun; 50(22):7686-7704. doi: 10.1039/d1dt00185j. [PMID: 33982702]
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