Muramyl Dipeptide (BioDeep_00001872289)
代谢物信息卡片
Ac-muramyl-Ala-D-Glu-NH2
化学式: C19H32N4O11 (492.2067482)
中文名称: N-乙酰胞壁酰基-L-丙氨酰基-D-异谷氨酰胺 水合物
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(C(=O)NC(CCC(=O)O)C(=O)N)NC(=O)C(C)OC1C(C(OC(C1O)CO)O)NC(=O)C
InChI: InChI=1S/C19H32N4O11/c1-7(17(30)23-10(16(20)29)4-5-12(26)27)21-18(31)8(2)33-15-13(22-9(3)25)19(32)34-11(6-24)14(15)28/h7-8,10-11,13-15,19,24,28,32H,4-6H2,1-3H3,(H2,20,29)(H,21,31)(H,22,25)(H,23,30)(H,26,27)/t7-,8+,10+,11+,13+,14+,15+,19+/m0/s1
数据库引用编号
6 个数据库交叉引用编号
- ChEBI: CHEBI:59414
- PubChem: 451714
- ChEMBL: CHEMBL369794
- MeSH: Acetylmuramyl-Alanyl-Isoglutamine
- CAS: 53678-77-6
- CAS: 87420-48-2
分类词条
相关代谢途径
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)
0 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
- Giada Botti, Anna Bianchi, Barbara Pavan, Paola Tedeschi, Valentina Albanese, Luca Ferraro, Federico Spizzo, Lucia Del Bianco, Alessandro Dalpiaz. Effects of Microencapsulated Ferulic Acid or Its Prodrug Methyl Ferulate on Neuroinflammation Induced by Muramyl Dipeptide.
International journal of environmental research and public health.
2022 08; 19(17):. doi:
10.3390/ijerph191710609. [PMID: 36078325] - Charles W Hespen, Xiaohui Zhao, Howard C Hang. Membrane targeting enhances muramyl dipeptide binding to NOD2 and Arf6-GTPase in mammalian cells.
Chemical communications (Cambridge, England).
2022 Jun; 58(46):6598-6601. doi:
10.1039/d2cc01903e. [PMID: 35584401] - Yuan Gao, Yajuan Fan, Zai Yang, Qingyan Ma, Binbin Zhao, Xiaoyan He, Fengjie Gao, Li Qian, Wei Wang, Ce Chen, Yunchun Chen, Chengge Gao, Xiancang Ma, Feng Zhu. Systems biological assessment of altered cytokine responses to bacteria and fungi reveals impaired immune functionality in schizophrenia.
Molecular psychiatry.
2022 02; 27(2):1205-1216. doi:
10.1038/s41380-021-01362-0. [PMID: 34728799] - Haifang Wang, Xueying Shen, Xiaojiao Zheng, Ying Pan, Qin Zhang, Zhihua Liu. Intestinal lysozyme releases Nod2 ligand(s) to promote the intestinal mucosal adjuvant activity of cholera toxin.
Science China. Life sciences.
2021 Oct; 64(10):1720-1731. doi:
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International immunopharmacology.
2021 Jan; 90(?):107224. doi:
10.1016/j.intimp.2020.107224. [PMID: 33302036] - Natalia E Moskaleva, Pavel A Markin, Roman M Kuznetsov, Tatiana M Andronova, Svetlana A Appolonova. Determination of the immunostimulatory drug-glucosoaminyl-muramyl-dipeptide-in human plasma using HPLC-MS/MS and its application to a pharmacokinetic study.
Biomedical chromatography : BMC.
2020 Dec; 34(12):e4948. doi:
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Cells.
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Journal of immunology research.
2020; 2020(?):5812743. doi:
10.1155/2020/5812743. [PMID: 32626788] - Guo-Guang Ma, Bin Shi, Xue-Peng Zhang, Yue Qiu, Guo-Wei Tu, Zhe Luo. The pathways and mechanisms of muramyl dipeptide transcellular transport mediated by PepT1 in enterogenous infection.
Annals of translational medicine.
2019 Sep; 7(18):473. doi:
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Drug discoveries & therapeutics.
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Frontiers in immunology.
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Shock (Augusta, Ga.).
2018 11; 50(5):606-612. doi:
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Journal of medicinal chemistry.
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Gut.
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Scientific reports.
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Nature medicine.
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Digestive diseases and sciences.
2015 Nov; 60(11):3264-70. doi:
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Inflammation.
2015 Feb; 38(1):272-7. doi:
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Immunobiology.
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Shock (Augusta, Ga.).
2014 Aug; 42(2):161-7. doi:
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Pediatric blood & cancer.
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Experimental eye research.
2013 Nov; 116(?):324-36. doi:
10.1016/j.exer.2013.10.005. [PMID: 24135297] - Feng You, Jinping Hu, Xue Li, Yan Li. The elimination of MTC-220, a novel anti-tumor agent of conjugate of paclitaxel and muramyl dipeptide analogue, in rats.
Cancer chemotherapy and pharmacology.
2013 Jun; 71(6):1453-62. doi:
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International immunopharmacology.
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Methods in enzymology.
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10.1016/s0076-6879(10)78016-2. [PMID: 20816488] - Shoichi Kusumoto, Koichi Fukase, Tetsuo Shiba. Key structures of bacterial peptidoglycan and lipopolysaccharide triggering the innate immune system of higher animals: chemical synthesis and functional studies.
Proceedings of the Japan Academy. Series B, Physical and biological sciences.
2010; 86(4):322-37. doi:
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Clinical and experimental immunology.
2009 Jun; 156(3):428-33. doi:
10.1111/j.1365-2249.2009.03926.x. [PMID: 19438594] - Noemí Marina-García, Luigi Franchi, Yun-Gi Kim, Yonjun Hu, David E Smith, Geert-Jan Boons, Gabriel Núñez. Clathrin- and dynamin-dependent endocytic pathway regulates muramyl dipeptide internalization and NOD2 activation.
Journal of immunology (Baltimore, Md. : 1950).
2009 Apr; 182(7):4321-7. doi:
10.4049/jimmunol.0802197. [PMID: 19299732] - Oh Yoen Kim, Antoine Monsel, Michèle Bertrand, Jean-Marc Cavaillon, Pierre Coriat, Minou Adib-Conquy. Translocation of bacterial NOD2 agonist and its link with inflammation.
Critical care (London, England).
2009; 13(4):R124. doi:
10.1186/cc7980. [PMID: 19638210] - Emília Dvoroznáková, Jarmila Porubcová, Viliam Snábel, Peter Fedorocko. Imunomodulative effect of liposomized muramyltripeptide phosphatidylethanolamine (L-MTP-PE) on mice with alveolar echinococcosis and treated with albendazole.
Parasitology research.
2008 Sep; 103(4):919-29. doi:
10.1007/s00436-008-1077-2. [PMID: 18587669] - Vanessa Beynon, Sebastian Cotofana, Stephan Brand, Peter Lohse, Anja Mair, Stefanie Wagner, Thomas Mussack, Thomas Ochsenkühn, Matthias Folwaczny, Christian Folwaczny, Jürgen Glas, Helga-Paula Török. NOD2/CARD15 genotype influences MDP-induced cytokine release and basal IL-12p40 levels in primary isolated peripheral blood monocytes.
Inflammatory bowel diseases.
2008 Aug; 14(8):1033-40. doi:
10.1002/ibd.20441. [PMID: 18383179] - H L Rosenzweig, T M Martin, S R Planck, K Galster, M M Jann, M P Davey, K Kobayashi, R A Flavell, J T Rosenbaum. Activation of NOD2 in vivo induces IL-1beta production in the eye via caspase-1 but results in ocular inflammation independently of IL-1 signaling.
Journal of leukocyte biology.
2008 Aug; 84(2):529-36. doi:
10.1189/jlb.0108015. [PMID: 18495787] - Xiao-Li Xu, Raymond Teck Ho Lee, Hao-Ming Fang, Yan-Ming Wang, Rong Li, Hao Zou, Yong Zhu, Yue Wang. Bacterial peptidoglycan triggers Candida albicans hyphal growth by directly activating the adenylyl cyclase Cyr1p.
Cell host & microbe.
2008 Jul; 4(1):28-39. doi:
10.1016/j.chom.2008.05.014. [PMID: 18621008] - Shurong Huang, Ling Zhao, Kihoon Kim, Dong Seok Lee, Daniel H Hwang. Inhibition of Nod2 signaling and target gene expression by curcumin.
Molecular pharmacology.
2008 Jul; 74(1):274-81. doi:
10.1124/mol.108.046169. [PMID: 18413660] - Marcus Mühlbauer, Adam W Cheely, Suresh Yenugu, Christian Jobin. Regulation and functional impact of lipopolysaccharide induced Nod2 gene expression in the murine epididymal epithelial cell line PC1.
Immunology.
2008 Jun; 124(2):256-64. doi:
10.1111/j.1365-2567.2007.02763.x. [PMID: 18284470] - Bas B van Rijn, Arie Franx, Eric A P Steegers, Christianne J M de Groot, Rogier M Bertina, Gerard Pasterkamp, Hieronymus A M Voorbij, Hein W Bruinse, Mark Roest. Maternal TLR4 and NOD2 gene variants, pro-inflammatory phenotype and susceptibility to early-onset preeclampsia and HELLP syndrome.
PloS one.
2008 Apr; 3(4):e1865. doi:
10.1371/journal.pone.0001865. [PMID: 18382655] - Marina Hasiwa, Ondrej Kylián, Thomas Hartung, Francois Rossi. Removal of immune-stimulatory components from surfaces by plasma discharges.
Innate immunity.
2008 Apr; 14(2):89-97. doi:
10.1177/1753425907088243. [PMID: 18713725] - Mohammad S Khalifeh, Wael Hananeh, Raida Al-Rukibat, Omar Okour, Assia Boumezrag. Clinical and histopathological evaluation of MDP/collagen induced arthritis rat model (MCIA) after treatment with Urtica dioica, plantago major and Hypericum perforatum L herbal mixture.
Experimental animals.
2008 Apr; 57(2):101-10. doi:
10.1538/expanim.57.101. [PMID: 18421172] - Oliver Murch, Maha Abdelrahman, Amar Kapoor, Christoph Thiemermann. Muramyl dipeptide enhances the response to endotoxin to cause multiple organ injury in the anesthetized rat.
Shock (Augusta, Ga.).
2008 Mar; 29(3):388-94. doi:
10.1097/shk.0b013e3181453e59. [PMID: 17693945] - Jörg Huwyler, Jürgen Drewe, Stephan Krähenbuhl. Tumor targeting using liposomal antineoplastic drugs.
International journal of nanomedicine.
2008; 3(1):21-9. doi:
10.2147/ijn.s1253. [PMID: 18488413] - Masanori Tohno, Wataru Ueda, Yuko Azuma, Tomoyuki Shimazu, Shinichiro Katoh, Ji Ming Wang, Hisashi Aso, Haruhiko Takada, Yasushi Kawai, Tadao Saito, Haruki Kitazawa. Molecular cloning and functional characterization of porcine nucleotide-binding oligomerization domain-2 (NOD2).
Molecular immunology.
2008 Jan; 45(1):194-203. doi:
10.1016/j.molimm.2007.04.019. [PMID: 17559936] - Matija Hedl, Jing Li, Judy H Cho, Clara Abraham. Chronic stimulation of Nod2 mediates tolerance to bacterial products.
Proceedings of the National Academy of Sciences of the United States of America.
2007 Dec; 104(49):19440-5. doi:
10.1073/pnas.0706097104. [PMID: 18032608] - Andrea A Gust, Raja Biswas, Heike D Lenz, Thomas Rauhut, Stefanie Ranf, Birgit Kemmerling, Friedrich Götz, Erich Glawischnig, Justin Lee, Georg Felix, Thorsten Nürnberger. Bacteria-derived peptidoglycans constitute pathogen-associated molecular patterns triggering innate immunity in Arabidopsis.
The Journal of biological chemistry.
2007 Nov; 282(44):32338-48. doi:
10.1074/jbc.m704886200. [PMID: 17761682] - Martin Philpott, Laura Mackay, Lynnette R Ferguson, Davanea Forbes, Margot Skinner. Cell culture models in developing nutrigenomics foods for inflammatory bowel disease.
Mutation research.
2007 Sep; 622(1-2):94-102. doi:
10.1016/j.mrfmmm.2007.04.013. [PMID: 17568627] - Patrick Lécine, Sophie Esmiol, Jean-Yves Métais, Cendrine Nicoletti, Claire Nourry, Christine McDonald, Gabriel Nunez, Jean-Pierre Hugot, Jean-Paul Borg, Vincent Ollendorff. The NOD2-RICK complex signals from the plasma membrane.
The Journal of biological chemistry.
2007 May; 282(20):15197-207. doi:
10.1074/jbc.m606242200. [PMID: 17355968] - S C Madu, A Faurie, J M Pettifor, H P Laburn. Growth failure after recurrent fever in young guinea pigs.
Physiology & behavior.
2007 Mar; 90(4):656-63. doi:
10.1016/j.physbeh.2006.12.002. [PMID: 17275044] - Neil Cartwright, Oliver Murch, Shaun K McMaster, Mark J Paul-Clark, David A van Heel, Bernhard Ryffel, Valerie F J Quesniaux, Timothy W Evans, Christoph Thiemermann, Jane A Mitchell. Selective NOD1 agonists cause shock and organ injury/dysfunction in vivo.
American journal of respiratory and critical care medicine.
2007 Mar; 175(6):595-603. doi:
10.1164/rccm.200608-1103oc. [PMID: 17234906] - Marlyn P Langford, Jeffrey M Gosslee, Chanping Liang, Dequan Chen, Thomas B Redens, Tomas C Welbourne. Apical localization of glutamate in GLAST-1, glutamine synthetase positive ciliary body nonpigmented epithelial cells.
Clinical ophthalmology (Auckland, N.Z.).
2007 Mar; 1(1):43-53. doi:
. [PMID: 19668465] - Euphemia Leung, Jiwon Hong, Alan Fraser, Geoffrey W Krissansen. Splicing of NOD2 (CARD15) RNA transcripts.
Molecular immunology.
2007 Jan; 44(4):284-94. doi:
10.1016/j.molimm.2006.03.009. [PMID: 16675018] - Manfred G Ismair, Stephan R Vavricka, Gerd A Kullak-Ublick, Michael Fried, Dominique Mengin-Lecreulx, Stephen E Girardin. hPepT1 selectively transports muramyl dipeptide but not Nod1-activating muramyl peptides.
Canadian journal of physiology and pharmacology.
2006 Dec; 84(12):1313-9. doi:
10.1139/y06-076. [PMID: 17487240] - Jaume Pons, Jaume Sauleda, Verónica Regueiro, Carmen Santos, Meritxell López, Joana Ferrer, Alvar G N Agustí, José A Bengoechea. Expression of Toll-like receptor 2 is up-regulated in monocytes from patients with chronic obstructive pulmonary disease.
Respiratory research.
2006 Apr; 7(?):64. doi:
10.1186/1465-9921-7-64. [PMID: 16606450] - Sterghios A Moschos, Vincent W Bramwell, Satyanarayna Somavarapu, H Oya Alpar. Modulating the adjuvanticity of alum by co-administration of muramyl di-peptide (MDP) or Quil-A.
Vaccine.
2006 Feb; 24(8):1081-6. doi:
10.1016/j.vaccine.2005.09.007. [PMID: 16219395] - Eske Voss, Jan Wehkamp, Kai Wehkamp, Eduard F Stange, Jens M Schröder, Jürgen Harder. NOD2/CARD15 mediates induction of the antimicrobial peptide human beta-defensin-2.
The Journal of biological chemistry.
2006 Jan; 281(4):2005-11. doi:
10.1074/jbc.m511044200. [PMID: 16319062] - Marlyn P Langford, Dequan Chen, Jeffrey Gosslee, Raghunath P Misra, Thomas B Redens, Donald E Texada. Intracameral toxicity of bacterial components muramyl dipeptide and staurosporine: ciliary cyst formation, epithelial cell apoptosis and necrosis.
Cutaneous and ocular toxicology.
2006; 25(2):85-101. doi:
10.1080/15569520600695538. [PMID: 16835145] - Hiroyuki Tada, Setsuya Aiba, Ken-Ichiro Shibata, Toshiaki Ohteki, Haruhiko Takada. Synergistic effect of Nod1 and Nod2 agonists with toll-like receptor agonists on human dendritic cells to generate interleukin-12 and T helper type 1 cells.
Infection and immunity.
2005 Dec; 73(12):7967-76. doi:
10.1128/iai.73.12.7967-7976.2005. [PMID: 16299289] - Eva Tavares, Rosario Maldonado, Maria L Ojeda, Francisco J Miñano. Circulating inflammatory mediators during start of fever in differential diagnosis of gram-negative and gram-positive infections in leukopenic rats.
Clinical and diagnostic laboratory immunology.
2005 Sep; 12(9):1085-93. doi:
10.1128/cdli.12.9.1085-1093.2005. [PMID: 16148175] - Yun Yong Wang, Anders E Myhre, Solveig J Pettersen, Maria K Dahle, Simon J Foster, Christoph Thiemermann, Kristin Bjørnland, Ansgar O Aasen, Jacob E Wang. Peptidoglycan of Staphylococcus aureus induces enhanced levels of matrix metalloproteinase-9 in human blood originating from neutrophils.
Shock (Augusta, Ga.).
2005 Sep; 24(3):214-8. doi:
10.1097/01.shk.0000174935.13786.6c. [PMID: 16135959] - Ylva Linderson, Francesca Bresso, Eva Buentke, Sven Pettersson, Mauro D'Amato. Functional interaction of CARD15/NOD2 and Crohn's disease-associated TNFalpha polymorphisms.
International journal of colorectal disease.
2005 Jul; 20(4):305-11. doi:
10.1007/s00384-004-0732-z. [PMID: 15800781] - Dequan Chen, Donald E Texada, Chris Duggan, Chanping Liang, Thomas B Reden, Lakshmana M Kooragayala, Marlyn P Langford. Surface calreticulin mediates muramyl dipeptide-induced apoptosis in RK13 cells.
The Journal of biological chemistry.
2005 Jun; 280(23):22425-36. doi:
10.1074/jbc.m413380200. [PMID: 15817475] - Dimitar B Iliev, Cristina Q Liarte, Simon MacKenzie, Frederick W Goetz. Activation of rainbow trout (Oncorhynchus mykiss) mononuclear phagocytes by different pathogen associated molecular pattern (PAMP) bearing agents.
Molecular immunology.
2005 Jun; 42(10):1215-23. doi:
10.1016/j.molimm.2004.11.023. [PMID: 15829310] - A Uehara, Y Sugawara, S Kurata, Y Fujimoto, K Fukase, S Kusumoto, Y Satta, T Sasano, S Sugawara, H Takada. Chemically synthesized pathogen-associated molecular patterns increase the expression of peptidoglycan recognition proteins via toll-like receptors, NOD1 and NOD2 in human oral epithelial cells.
Cellular microbiology.
2005 May; 7(5):675-86. doi:
10.1111/j.1462-5822.2004.00500.x. [PMID: 15839897] - Jean-Loup Lemesre, Philippe Holzmuller, Mireille Cavaleyra, Rachel Bras Gonçalves, Grégory Hottin, Gérard Papierok. Protection against experimental visceral leishmaniasis infection in dogs immunized with purified excreted secreted antigens of Leishmania infantum promastigotes.
Vaccine.
2005 Apr; 23(22):2825-40. doi:
10.1016/j.vaccine.2004.11.061. [PMID: 15780731] - Sterghios A Moschos, Vincent W Bramwell, Satyanarayna Somavarapu, H Oya Alpar. Comparative immunomodulatory properties of a chitosan-MDP adjuvant combination following intranasal or intramuscular immunisation.
Vaccine.
2005 Mar; 23(16):1923-30. doi:
10.1016/j.vaccine.2004.10.016. [PMID: 15734064] - Koichi S Kobayashi, Mathias Chamaillard, Yasunori Ogura, Octavian Henegariu, Naohiro Inohara, Gabriel Nuñez, Richard A Flavell. Nod2-dependent regulation of innate and adaptive immunity in the intestinal tract.
Science (New York, N.Y.).
2005 Feb; 307(5710):731-4. doi:
10.1126/science.1104911. [PMID: 15692051] - Paul K B Chua, John E Corkill, Poh Sim Hooi, Soo Choon Cheng, Craig Winstanley, C Anthony Hart. Isolation of Waddlia malaysiensis, a novel intracellular bacterium, from fruit bat (Eonycteris spelaea).
Emerging infectious diseases.
2005 Feb; 11(2):271-7. doi:
10.3201/eid1102.040746. [PMID: 15752446] - A Uehara, S Yang, Y Fujimoto, K Fukase, S Kusumoto, K Shibata, S Sugawara, H Takada. Muramyldipeptide and diaminopimelic acid-containing desmuramylpeptides in combination with chemically synthesized Toll-like receptor agonists synergistically induced production of interleukin-8 in a NOD2- and NOD1-dependent manner, respectively, in human monocytic cells in culture.
Cellular microbiology.
2005 Jan; 7(1):53-61. doi:
10.1111/j.1462-5822.2004.00433.x. [PMID: 15617523]