Uridine diphosphategalactose (BioDeep_00000014332)

   

natural product human metabolite PANOMIX_OTCML-2023 Endogenous BioNovoGene_Lab2019 Volatile Flavor Compounds


代谢物信息卡片


[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

化学式: C15H24N2O17P2 (566.0550194)
中文名称: UDP-半乳糖, UDP-GAL(UDP-半乳糖)
谱图信息: 最多检出来源 Homo sapiens(urine) 0.3%

分子结构信息

SMILES: C1=CN(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)OC3C(C(C(C(O3)CO)O)O)O)O)O
InChI: InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8+,9-,10+,11-,12-,13-,14-/m1/s1

描述信息

Uridine diphosphategalactose (UDPgal) is a nucleoside diphosphate sugar which can be epimerized into UDPglucose for entry into the mainstream of carbohydrate metabolism. UDPgal is a pivotal compound in the metabolism of galactose. UDPgal is a product of the galactose-l-phosphate uridyl transferase (EC 2.7.7.10) reaction but may also be made from Glucose-l-P, involving uridine diphosphate galactose-4-epimerase (EC 5.1.3.2). UDPgal is the necessary galactosyl donor of galactose in the metabolism to incorporate it into complex oligosaccharides, glycoproteins and glycolipids (galactosides). Defective galactosylation of complex glycoconjugates exists in tissues from galactosemic patients. There is a tendency for galactosemic red cell UDPgal to be in the low normal range with a high uridine diphosphate glucose to UDP-gal ratio. This may reflect an inability of red cell UDPgal-4-epimerase to maintain a normal ratio and consequently higher levels of UDPgal. In the more complex white blood cells and cultured fibroblasts, the UDPgal content and the uridine diphosphate glucose to UDPgal ratio of galactosemics are normal. Therefore, defective galactosylation observed in galactosemic fibroblasts must result from a defect in the transfer of galactose from UDPgal to these moieties. (PMID: 2122114, 7671968) [HMDB]
Uridine diphosphategalactose (UDPgal) is a nucleoside diphosphate sugar which can be epimerized into UDPglucose for entry into the mainstream of carbohydrate metabolism. UDPgal is a pivotal compound in the metabolism of galactose. UDPgal is a product of the galactose-l-phosphate uridyl transferase (EC 2.7.7.10) reaction but may also be made from Glucose-l-P, involving uridine diphosphate galactose-4-epimerase (EC 5.1.3.2). UDPgal is the necessary galactosyl donor of galactose in the metabolism to incorporate it into complex oligosaccharides, glycoproteins and glycolipids (galactosides). Defective galactosylation of complex glycoconjugates exists in tissues from galactosemic patients. There is a tendency for galactosemic red cell UDPgal to be in the low normal range with a high uridine diphosphate glucose to UDP-gal ratio. This may reflect an inability of red cell UDPgal-4-epimerase to maintain a normal ratio and consequently higher levels of UDPgal. In the more complex white blood cells and cultured fibroblasts, the UDPgal content and the uridine diphosphate glucose to UDPgal ratio of galactosemics are normal. Therefore, defective galactosylation observed in galactosemic fibroblasts must result from a defect in the transfer of galactose from UDPgal to these moieties. (PMID: 2122114, 7671968).
Acquisition and generation of the data is financially supported in part by CREST/JST.
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同义名列表

53 个代谢物同义名

[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid; {[(2R,3S,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid; Uridine 5-[3-(D-galactopyranosyl) dihydrogen diphosphate]; Uridine pyrophosphate alpha-D-galactopyranosyl ester; Uridine 5-(alpha-D-galactopyranosyl pyrophosphate); Uridine 5-pyrophosphate a-D-galactopyranosyl ester; Uridine pyrophosphate a-D-galactopyranosyl ester; Uridine[5]diphospho[1]-α-D-galactopyranose; Uridine 5-pyrophosphate alpha-D-galactosyl ester; Uridine 5’-(α-D-galactopyranosyl pyrophosphate); Uridine 5-(α-D-galactopyranosyl pyrophosphate); Uridine 5-pyrophosphate a-D-galactosyl ester; Uridine 5-pyrophosphate D-galactosyl ester; Uridine-5-diphosphogalactose disodium salt; Uridine diphosphoric acid galactose; Uridine 5’-diphosphate galactose; Uridine 5-diphosphate galactose; Galactose-uridine-5-diphosphate; Uridine diphosphate-D-galactose; Galactose, uridine diphosphate; Diphosphate galactose, uridine; Uridine 5’-diphosphogalactose; Uridine diphosphate-galactose; Uridine-diphosphate-galactose; Pyrophosphogalactose, uridine; Uridine diphosphate galactose; Uridine pyrophosphogalactose; Uridinediphosphate galactose; Uridine 5-diphosphogalactose; Uridine diphosphategalactose; UDP-Galactose disodium salt; Diphosphogalactose, uridine; UDP-alpha-D-Galactopyranose; Uridine diphosphogalactose; Uridinediphosphogalactose; UDP-a-D-Galactopyranose; UDP-α-D-galactopyranose; UDP-D-Galactopyranose; UDP-alpha-D-Galactose; UDP-galactopyranose; UDP-a-D-Galactose; UDP-α-D-Galactose; UDP-D-galactose; Galactose, UDP; UDP Galactose; UDP-Galactose; UDPgalactose; UDP-Gal; Udpgal; GDU; UPG; Uridine diphosphategalactose(UDP-galactose); UDP-alpha-D-galactose



数据库引用编号

36 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(4)

PlantCyc(0)

代谢反应

50 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(7)

WikiPathways(3)

Plant Reactome(0)

INOH(3)

PlantCyc(0)

COVID-19 Disease Map(1)

PathBank(36)

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。



文献列表

  • Lihua Wang-Eckhardt, Ivonne Becker, Matthias Eckhardt. The PGRMC1 Antagonist AG-205 Inhibits Synthesis of Galactosylceramide and Sulfatide. Cells. 2021 12; 10(12):. doi: 10.3390/cells10123520. [PMID: 34944026]
  • Yiyi Gong, Panpan Zhang, Zheng Liu, Jieqiong Li, Hui Lu, Yujie Wang, Bintao Qiu, Mu Wang, Yunyun Fei, Hua Chen, Linyi Peng, Jing Li, Jiaxin Zhou, Qun Shi, Xuan Zhang, Min Shen, Xiaofeng Zeng, Fengchun Zhang, Wen Zhang. UPLC-MS based plasma metabolomics and lipidomics reveal alterations associated with IgG4-related disease. Rheumatology (Oxford, England). 2021 07; 60(7):3252-3261. doi: 10.1093/rheumatology/keaa775. [PMID: 33341881]
  • Chenying Dong, Diange Li, Ru Wang, Jian Chu, Zhongying Gong, Dawei Zhou. Expression, purification, and characterization of a new Glucosyltransferase involved in the third step of O-antigen repeating-unit biosynthesis of Escherichia coli O152. Glycoconjugate journal. 2020 04; 37(2):139-149. doi: 10.1007/s10719-020-09907-1. [PMID: 31974821]
  • Yan Yang, Ying-Ying Wang, Min-Zhi Liu, Zhi-Ying Sun, Wei Wang. cDNA isolation and functional characterization of UDP-glucose 4-epimerase from Davallia divaricate. Journal of Asian natural products research. 2020 Mar; 22(3):271-278. doi: 10.1080/10286020.2019.1703697. [PMID: 31888381]
  • Meng Zhang, Fu-Dong Li, Kai Li, Zi-Long Wang, Yu-Xi Wang, Jun-Bin He, Hui-Fei Su, Zhong-Yi Zhang, Chang-Biao Chi, Xiao-Meng Shi, Cai-Hong Yun, Zhi-Yong Zhang, Zhen-Ming Liu, Liang-Ren Zhang, Dong-Hui Yang, Ming Ma, Xue Qiao, Min Ye. Functional Characterization and Structural Basis of an Efficient Di-C-glycosyltransferase from Glycyrrhiza glabra. Journal of the American Chemical Society. 2020 02; 142(7):3506-3512. doi: 10.1021/jacs.9b12211. [PMID: 31986016]
  • Bobby G Ng, Paulina Sosicka, Satish Agadi, Mohammed Almannai, Carlos A Bacino, Rita Barone, Lorenzo D Botto, Jennifer E Burton, Colleen Carlston, Brian Hon-Yin Chung, Julie S Cohen, David Coman, Katrina M Dipple, Naghmeh Dorrani, William B Dobyns, Abdallah F Elias, Leon Epstein, William A Gahl, Domenico Garozzo, Trine Bjørg Hammer, Jaclyn Haven, Delphine Héron, Matthew Herzog, George E Hoganson, Jesse M Hunter, Mahim Jain, Jane Juusola, Shenela Lakhani, Hane Lee, Joy Lee, Katherine Lewis, Nicola Longo, Charles Marques Lourenço, Christopher C Y Mak, Dianalee McKnight, Bryce A Mendelsohn, Cyril Mignot, Ghayda Mirzaa, Wendy Mitchell, Hiltrud Muhle, Stanley F Nelson, Mariusz Olczak, Christina G S Palmer, Arthur Partikian, Marc C Patterson, Tyler M Pierson, Shane C Quinonez, Brigid M Regan, M Elizabeth Ross, Maria J Guillen Sacoto, Fernando Scaglia, Ingrid E Scheffer, Devorah Segal, Nilika Shah Singhal, Pasquale Striano, Luisa Sturiale, Joseph D Symonds, Sha Tang, Eric Vilain, Mary Willis, Lynne A Wolfe, Hui Yang, Shoji Yano, Zöe Powis, Sharon F Suchy, Jill A Rosenfeld, Andrew C Edmondson, Stephanie Grunewald, Hudson H Freeze. SLC35A2-CDG: Functional characterization, expanded molecular, clinical, and biochemical phenotypes of 30 unreported Individuals. Human mutation. 2019 07; 40(7):908-925. doi: 10.1002/humu.23731. [PMID: 30817854]
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  • Estelle Garénaux, Mayumi Kanagawa, Tomoyuki Tsuchiyama, Kazuki Hori, Takeru Kanazawa, Ami Goshima, Mitsuru Chiba, Hiroshi Yasue, Akemi Ikeda, Yoshiki Yamaguchi, Chihiro Sato, Ken Kitajima. Discovery, primary, and crystal structures and capacitation-related properties of a prostate-derived heparin-binding protein WGA16 from boar sperm. The Journal of biological chemistry. 2015 Feb; 290(9):5484-501. doi: 10.1074/jbc.m114.635268. [PMID: 25568322]
  • Sanna Oikari, Tuula Venäläinen, Markku Tammi. Borate-aided anion exchange high-performance liquid chromatography of uridine diphosphate-sugars in brain, heart, adipose and liver tissues. Journal of chromatography. A. 2014 Jan; 1323(?):82-6. doi: 10.1016/j.chroma.2013.11.004. [PMID: 24309714]
  • René Jørgensen, Thomas Pesnot, Ho Jun Lee, Monica M Palcic, Gerd K Wagner. Base-modified donor analogues reveal novel dynamic features of a glycosyltransferase. The Journal of biological chemistry. 2013 Sep; 288(36):26201-26208. doi: 10.1074/jbc.m113.465963. [PMID: 23836908]
  • Kinnari B Patel, Ewa Ciepichal, Ewa Swiezewska, Miguel A Valvano. The C-terminal domain of the Salmonella enterica WbaP (UDP-galactose:Und-P galactose-1-phosphate transferase) is sufficient for catalytic activity and specificity for undecaprenyl monophosphate. Glycobiology. 2012 Jan; 22(1):116-22. doi: 10.1093/glycob/cwr114. [PMID: 21856724]
  • Changchang Xu, Bin Liu, Bo Hu, Yanfang Han, Lu Feng, John S Allingham, Walter A Szarek, Lei Wang, Inka Brockhausen. Biochemical characterization of UDP-Gal:GlcNAc-pyrophosphate-lipid β-1,4-Galactosyltransferase WfeD, a new enzyme from Shigella boydii type 14 that catalyzes the second step in O-antigen repeating-unit synthesis. Journal of bacteriology. 2011 Jan; 193(2):449-59. doi: 10.1128/jb.00737-10. [PMID: 21057010]
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  • Yusuke Ban, Satoru Kondo, Benjamin Ewa Ubi, Chikako Honda, Hideo Bessho, Takaya Moriguchi. UDP-sugar biosynthetic pathway: contribution to cyanidin 3-galactoside biosynthesis in apple skin. Planta. 2009 Oct; 230(5):871-81. doi: 10.1007/s00425-009-0993-4. [PMID: 19652996]
  • Hyojin Ko, Arijit Das, Rhonda L Carter, Ingrid P Fricks, Yixing Zhou, Andrei A Ivanov, Artem Melman, Bhalchandra V Joshi, Pavol Kovác, Jan Hajduch, Kenneth L Kirk, T Kendall Harden, Kenneth A Jacobson. Molecular recognition in the P2Y(14) receptor: Probing the structurally permissive terminal sugar moiety of uridine-5'-diphosphoglucose. Bioorganic & medicinal chemistry. 2009 Jul; 17(14):5298-311. doi: 10.1016/j.bmc.2009.05.024. [PMID: 19502066]
  • Ingrid P Fricks, Rhonda L Carter, Eduardo R Lazarowski, T Kendall Harden. Gi-dependent cell signaling responses of the human P2Y14 receptor in model cell systems. The Journal of pharmacology and experimental therapeutics. 2009 Jul; 330(1):162-8. doi: 10.1124/jpet.109.150730. [PMID: 19339661]
  • Frédérique Moyrand, Ingrid Lafontaine, Thierry Fontaine, Guilhem Janbon. UGE1 and UGE2 regulate the UDP-glucose/UDP-galactose equilibrium in Cryptococcus neoformans. Eukaryotic cell. 2008 Dec; 7(12):2069-77. doi: 10.1128/ec.00189-08. [PMID: 18820075]
  • Yngve Ostberg, Stefan Berg, Pär Comstedt, Ake Wieslander, Sven Bergström. Functional analysis of a lipid galactosyltransferase synthesizing the major envelope lipid in the Lyme disease spirochete Borrelia burgdorferi. FEMS microbiology letters. 2007 Jul; 272(1):22-9. doi: 10.1111/j.1574-6968.2007.00728.x. [PMID: 17456185]
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  • Hyojin Ko, Ingrid Fricks, Andrei A Ivanov, T Kendall Harden, Kenneth A Jacobson. Structure-activity relationship of uridine 5'-diphosphoglucose analogues as agonists of the human P2Y14 receptor. Journal of medicinal chemistry. 2007 May; 50(9):2030-9. doi: 10.1021/jm061222w. [PMID: 17407275]
  • Johannes Rösti, Christopher J Barton, Sandra Albrecht, Paul Dupree, Markus Pauly, Kim Findlay, Keith Roberts, Georg J Seifert. UDP-glucose 4-epimerase isoforms UGE2 and UGE4 cooperate in providing UDP-galactose for cell wall biosynthesis and growth of Arabidopsis thaliana. The Plant cell. 2007 May; 19(5):1565-79. doi: 10.1105/tpc.106.049619. [PMID: 17496119]
  • Paolo Ciana, Marta Fumagalli, Maria Letizia Trincavelli, Claudia Verderio, Patrizia Rosa, Davide Lecca, Silvia Ferrario, Chiara Parravicini, Valérie Capra, Paolo Gelosa, Uliano Guerrini, Silvia Belcredito, Mauro Cimino, Luigi Sironi, Elena Tremoli, G Enrico Rovati, Claudia Martini, Maria P Abbracchio. The orphan receptor GPR17 identified as a new dual uracil nucleotides/cysteinyl-leukotrienes receptor. The EMBO journal. 2006 Oct; 25(19):4615-27. doi: 10.1038/sj.emboj.7601341. [PMID: 16990797]
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  • Pedro J Montoya-Peleaz, John G Riley, Walter A Szarek, Miguel A Valvano, John S Schutzbach, Inka Brockhausen. Identification of a UDP-Gal: GlcNAc-R galactosyltransferase activity in Escherichia coli VW187. Bioorganic & medicinal chemistry letters. 2005 Feb; 15(4):1205-11. doi: 10.1016/j.bmcl.2004.11.077. [PMID: 15686943]
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