Muramic acid (BioDeep_00000001382)

 

Secondary id: BioDeep_00000405911

human metabolite natural product


代谢物信息卡片


(2R)-2-{[(2R,3R,4S,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid

化学式: C9H17NO7 (251.1005)
中文名称: 胞壁酸
谱图信息: 最多检出来源 Mus musculus(plant) 3.01%

Reviewed

Last reviewed on 2024-07-01.

Cite this Page

Muramic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/muramic_acid (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000001382). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC(C(=O)O)OC1C(C(OC(C1O)CO)O)N
InChI: InChI=1S/C9H17NO7/c1-3(8(13)14)16-7-5(10)9(15)17-4(2-11)6(7)12/h3-7,9,11-12,15H,2,10H2,1H3,(H,13,14)/t3-,4-,5-,6-,7+,9-/m1/s1

描述信息

Muramic acid is an amino sugar acid. In terms of chemical composition, it is the ether of lactic acid and glucosamine. It occurs naturally as N-acetylmuramic acid in peptidoglycan, whose primary function is a structural component of many typical bacterial cell walls. Muramic acid, also known as muramate or murexide, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Muramic acid is an amino sugar acid. It occurs naturally as N-acetylmuramic acid in peptidoglycan, whose primary function is a structural component of many typical bacterial cell walls. In terms of chemical composition, it is the ether of lactic acid and glucosamine.
Muramic acid is a marker of bacterial peptidoglycan, in environmental and clinical specimens. (PMID: 10778926) [HMDB]

Muramic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=1114-41-6 (retrieved 2024-07-01) (CAS RN: 1114-41-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

同义名列表

13 个代谢物同义名

(2R)-2-{[(2R,3R,4S,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid; (2R)-2-{[(2R,3R,4S,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoate; 2-Amino-3-O-D-1-carboxyethyl-2-deoxy-D-glucose; 3-O-alpha-Carboxyethyl-delta-glucosamine; 3-O-alpha-Carboxyethyl-D-glucosamine; Muramic acid hydrate; (+)-Muramic acid; Muramic acid; (+)-Muramate; Muramate; Murexide; Muramic acid; Muramic acid



数据库引用编号

33 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)

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 6 AQP1, CAT, FYB1, MVD, NOD1, NOD2
Peripheral membrane protein 1 HSD17B6
Nucleus 2 AQP1, FYB1
cytosol 6 CAT, FYB1, GYPA, MVD, NOD1, NOD2
phagocytic vesicle 2 NOD1, NOD2
nucleoplasm 1 GYPA
Cell membrane 7 AQP1, GYPA, NOD1, NOD2, SLC14A1, SLC4A1, TNF
Lipid-anchor 2 NOD1, NOD2
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 4 AQP1, RHAG, SLC14A1, SLC4A1
cell junction 1 FYB1
cell surface 2 NOD2, TNF
Golgi apparatus 1 NOD2
neuronal cell body 1 TNF
sarcolemma 1 AQP1
plasma membrane 11 AQP1, FYB1, GYPA, GYPB, INSRR, NOD1, NOD2, RHAG, SLC14A1, SLC4A1, TNF
Membrane 8 AQP1, CAT, GYPA, GYPB, INSRR, PGLYRP2, RHAG, SLC4A1
apical plasma membrane 2 AQP1, NOD1
axon 2 AQP1, INSRR
basolateral plasma membrane 5 AQP1, NOD1, NOD2, SLC14A1, SLC4A1
brush border 1 AQP1
caveola 1 AQP1
extracellular exosome 5 AQP1, CAT, LYZ, PGLYRP2, SLC4A1
Lumenal side 1 HSD17B6
endoplasmic reticulum 1 HSD17B6
extracellular space 6 CXCL8, IL10, IL4, IL6, LYZ, TNF
mitochondrion 2 CAT, NOD2
protein-containing complex 3 CAT, FYB1, NOD2
intracellular membrane-bounded organelle 2 CAT, HSD17B6
Microsome membrane 1 HSD17B6
Single-pass type I membrane protein 2 GYPA, INSRR
Secreted 4 CXCL8, IL10, IL4, IL6
extracellular region 8 CAT, CXCL8, IL10, IL4, IL6, LYZ, PGLYRP2, TNF
cytoplasmic side of plasma membrane 1 SLC4A1
Single-pass membrane protein 2 GYPA, GYPB
mitochondrial matrix 1 CAT
anchoring junction 1 FYB1
nuclear membrane 1 AQP1
external side of plasma membrane 1 TNF
actin cytoskeleton 1 FYB1
Z disc 1 SLC4A1
apical part of cell 1 AQP1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 NOD2
Apical cell membrane 1 NOD1
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 1 NOD2
focal adhesion 1 CAT
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
lateral plasma membrane 2 NOD1, SLC14A1
receptor complex 1 INSRR
phagocytic cup 1 TNF
cytoskeleton 1 NOD2
brush border membrane 1 AQP1
blood microparticle 1 SLC4A1
Basolateral cell membrane 4 NOD1, NOD2, SLC14A1, SLC4A1
basal plasma membrane 1 AQP1
[Isoform 3]: Cytoplasm 1 NOD2
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
endoplasmic reticulum lumen 1 IL6
specific granule lumen 1 LYZ
tertiary granule lumen 1 LYZ
azurophil granule lumen 1 LYZ
extrinsic component of plasma membrane 1 NOD2
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
ankyrin-1 complex 5 AQP1, GYPA, GYPB, RHAG, SLC4A1
cortical cytoskeleton 1 SLC4A1
catalase complex 1 CAT
interleukin-6 receptor complex 1 IL6
insulin receptor complex 1 INSRR
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Ashlyn S Hillman, Stephen N Hyland, Kimberly A Wodzanowski, DeVonte L Moore, Sushanta Ratna, Andrew Jemas, Liam-Michael D Sandles, Timothy Chaya, Arit Ghosh, Joseph M Fox, Catherine L Grimes. Minimalist Tetrazine N-Acetyl Muramic Acid Probes for Rapid and Efficient Labeling of Commensal and Pathogenic Peptidoglycans in Living Bacterial Culture and During Macrophage Invasion. Journal of the American Chemical Society. 2024 Mar; 146(10):6817-6829. doi: 10.1021/jacs.3c13644. [PMID: 38427023]
  • Yingde Xu, Liangjie Sun, Xiaodan Gao, Jingkuan Wang. Contrasting response of fungal versus bacterial residue accumulation within soil aggregates to long-term fertilization. Scientific reports. 2022 10; 12(1):17834. doi: 10.1038/s41598-022-22064-9. [PMID: 36284223]
  • Sébastien Crépin, Elizabeth N Ottosen, Katharina Peters, Sara N Smith, Stephanie D Himpsl, Waldemar Vollmer, Harry L T Mobley. The lytic transglycosylase MltB connects membrane homeostasis and in vivo fitness of Acinetobacter baumannii. Molecular microbiology. 2018 09; 109(6):745-762. doi: 10.1111/mmi.14000. [PMID: 29884996]
  • Kingchan Malisorn, Pawina Kanchanasin, Wongsakorn Phongsopitanun, Somboon Tanasupawat. Actinomadura rhizosphaerae sp. nov., isolated from rhizosphere soil of the plant Azadirachta indica. International journal of systematic and evolutionary microbiology. 2018 Sep; 68(9):3012-3016. doi: 10.1099/ijsem.0.002940. [PMID: 30063200]
  • Hathairat Rachniyom, Atsuko Matsumoto, Yuki Inahashi, Akira Take, Yoko Takahashi, Arinthip Thamchaipenet. Actinomadura barringtoniae sp. nov., an endophytic actinomycete isolated from the roots of Barringtonia acutangula (L.) Gaertn. International journal of systematic and evolutionary microbiology. 2018 May; 68(5):1584-1590. doi: 10.1099/ijsem.0.002714. [PMID: 29543147]
  • Margaret E Davidson, Joshua Schaeffer, Maggie L Clark, Sheryl Magzamen, Elizabeth J Brooks, Thomas J Keefe, Mary Bradford, Noa Roman-Muniz, John Mehaffy, Gregory Dooley, Jill A Poole, Frank M Mitloehner, Sue Reed, Marc B Schenker, Stephen J Reynolds. Personal exposure of dairy workers to dust, endotoxin, muramic acid, ergosterol, and ammonia on large-scale dairies in the high plains Western United States. Journal of occupational and environmental hygiene. 2018 03; 15(3):182-193. doi: 10.1080/15459624.2017.1403610. [PMID: 29157144]
  • Melissa E Bell, Kathryn A Bernard, Susan M Harrington, Nisha B Patel, Trudy-Ann Tucker, Maureen G Metcalfe, John R McQuiston. Lawsonella clevelandensis gen. nov., sp. nov., a new member of the suborder Corynebacterineae isolated from human abscesses. International journal of systematic and evolutionary microbiology. 2016 Aug; 66(8):2929-2935. doi: 10.1099/ijsem.0.001122. [PMID: 27130323]
  • Claudia Dalmastri, Luciano Gastaldo, Giorgia Letizia Marcone, Elisa Binda, Terenzio Congiu, Flavia Marinelli. Classification of Nonomuraea sp. ATCC 39727, an actinomycete that produces the glycopeptide antibiotic A40926, as Nonomuraea gerenzanensis sp. nov. International journal of systematic and evolutionary microbiology. 2016 Feb; 66(2):912-921. doi: 10.1099/ijsem.0.000810. [PMID: 26944798]
  • Jun Mao, Jian Wang, Huan-Qin Dai, Zhi-Dong Zhang, Qi-Yong Tang, Biao Ren, Na Yang, Michael Goodfellow, Li-Xin Zhang, Zhi-Heng Liu. Yuhushiella deserti gen. nov., sp. nov., a new member of the suborder Pseudonocardineae. International journal of systematic and evolutionary microbiology. 2011 Mar; 61(Pt 3):621-630. doi: 10.1099/ijs.0.019588-0. [PMID: 20400669]
  • Jaakko Pakarinen, Anne Hyvärinen, Mirja Salkinoja-Salonen, Sirpa Laitinen, Aino Nevalainen, Mika J Mäkelä, Tari Haahtela, Leena von Hertzen. Predominance of Gram-positive bacteria in house dust in the low-allergy risk Russian Karelia. Environmental microbiology. 2008 Dec; 10(12):3317-25. doi: 10.1111/j.1462-2920.2008.01723.x. [PMID: 18707614]
  • Ausra Gaidelyte, Virginija Cvirkaite-Krupovic, Rimantas Daugelavicius, Jaana K H Bamford, Dennis H Bamford. The entry mechanism of membrane-containing phage Bam35 infecting Bacillus thuringiensis. Journal of bacteriology. 2006 Aug; 188(16):5925-34. doi: 10.1128/jb.00107-06. [PMID: 16885461]
  • Ziqiang Guan, Steven D Breazeale, Christian R H Raetz. Extraction and identification by mass spectrometry of undecaprenyl diphosphate-MurNAc-pentapeptide-GlcNAc from Escherichia coli. Analytical biochemistry. 2005 Oct; 345(2):336-9. doi: 10.1016/j.ab.2005.07.002. [PMID: 16118008]
  • Jeya Nadesalingam, Alister W Dodds, Kenneth B M Reid, Nades Palaniyar. Mannose-binding lectin recognizes peptidoglycan via the N-acetyl glucosamine moiety, and inhibits ligand-induced proinflammatory effect and promotes chemokine production by macrophages. Journal of immunology (Baltimore, Md. : 1950). 2005 Aug; 175(3):1785-94. doi: 10.4049/jimmunol.175.3.1785. [PMID: 16034120]
  • Anne Bohin, Franck Bouchart, Colette Richet, Osarath Kol, Yves Leroy, Philippe Timmerman, Guillemette Huet, Jean-Pierre Bohin, Jean-Pierre Zanetta. GC/MS identification and quantification of constituents of bacterial lipids and glycoconjugates obtained after methanolysis as heptafluorobutyrate derivatives. Analytical biochemistry. 2005 May; 340(2):231-44. doi: 10.1016/j.ab.2005.02.017. [PMID: 15840496]
  • Yi-Chueh Lin, Kazunori Uemori, Dominique A de Briel, Vallapa Arunpairojana, Akira Yokota. Zimmermannella helvola gen. nov., sp. nov., Zimmermannella alba sp. nov., Zimmermannella bifida sp. nov., Zimmermannella faecalis sp. nov. and Leucobacter albus sp. nov., novel members of the family Microbacteriaceae. International journal of systematic and evolutionary microbiology. 2004 Sep; 54(Pt 5):1669-1676. doi: 10.1099/ijs.0.02741-0. [PMID: 15388726]
  • Yves Bourne, Corinne Houlès Astoul, Véronique Zamboni, Willy J Peumans, Laurence Menu-Bouaouiche, Els J M Van Damme, Annick Barre, Pierre Rougé. Structural basis for the unusual carbohydrate-binding specificity of jacalin towards galactose and mannose. The Biochemical journal. 2002 May; 364(Pt 1):173-80. doi: 10.1042/bj3640173. [PMID: 11988090]
  • D J Silva, C L Bowe, A A Branstrom, E R Baizman, M J Sofia. Synthesis and biological evaluation of analogues of bacterial lipid I. Bioorganic & medicinal chemistry letters. 2000 Dec; 10(24):2811-3. doi: 10.1016/s0960-894x(00)00583-7. [PMID: 11133098]
  • K Bal, L Larsson. New and simple procedure for the determination of muramic acid in chemically complex environments by gas chromatography-ion trap tandem mass spectrometry. Journal of chromatography. B, Biomedical sciences and applications. 2000 Jan; 738(1):57-65. doi: 10.1016/s0378-4347(99)00494-6. [PMID: 10778926]
  • E Bokma, G A van Koningsveld, M Jeronimus-Stratingh, J J Beintema. Hevamine, a chitinase from the rubber tree Hevea brasiliensis, cleaves peptidoglycan between the C-1 of N-acetylglucosamine and C-4 of N-acetylmuramic acid and therefore is not a lysozyme. FEBS letters. 1997 Jul; 411(2-3):161-3. doi: 10.1016/s0014-5793(97)00682-0. [PMID: 9271197]
  • H Brötz, G Bierbaum, P E Reynolds, H G Sahl. The lantibiotic mersacidin inhibits peptidoglycan biosynthesis at the level of transglycosylation. European journal of biochemistry. 1997 May; 246(1):193-9. doi: 10.1111/j.1432-1033.1997.t01-1-00193.x. [PMID: 9210483]
  • Y Bourne, A Ayouba, P Rougé, C Cambillau. Interaction of a legume lectin with two components of the bacterial cell wall. A crystallographic study. The Journal of biological chemistry. 1994 Apr; 269(13):9429-35. doi: . [PMID: 8144527]
  • M P Hazenberg, H de Visser. Assay for N-acetylmuramyl-L-alanine amidase in serum by determination of muramic acid released from the peptidoglycan of Brevibacterium divaricatum. European journal of clinical chemistry and clinical biochemistry : journal of the Forum of European Clinical Chemistry Societies. 1992 Mar; 30(3):141-4. doi: . [PMID: 1350922]
  • J Kool, J G Ruseler-van Embden, L M van Lieshout, H de Visser, M Y Gerrits-Boeye, W B van den Berg, M P Hazenberg. Induction of arthritis in rats by soluble peptidoglycan-polysaccharide complexes produced by human intestinal flora. Arthritis and rheumatism. 1991 Dec; 34(12):1611-6. doi: 10.1002/art.1780341222. [PMID: 1747146]
  • A Ayouba, C Chatelain, P Rougé. Legume lectins interact with muramic acid and N-acetylmuramic acid. FEBS letters. 1991 Sep; 289(1):102-4. doi: 10.1016/0014-5793(91)80918-s. [PMID: 1893996]
  • A Fox, K Fox. Rapid elimination of a synthetic adjuvant peptide from the circulation after systemic administration and absence of detectable natural muramyl peptides in normal serum at current analytical limits. Infection and immunity. 1991 Mar; 59(3):1202-5. doi: 10.1128/iai.59.3.1202-1205.1991. [PMID: 1997424]
  • H Harz, K Burgdorf, J V Höltje. Isolation and separation of the glycan strands from murein of Escherichia coli by reversed-phase high-performance liquid chromatography. Analytical biochemistry. 1990 Oct; 190(1):120-8. doi: 10.1016/0003-2697(90)90144-x. [PMID: 2285138]
  • R J Kraus, F L Shinnick, J A Marlett. Simultaneous determination of neutral and amino sugars in biological materials. Journal of chromatography. 1990 Jul; 513(?):71-81. doi: 10.1016/s0021-9673(01)89426-7. [PMID: 2229246]
  • M P Hazenberg, A M Pennock-Schröder, F Wensinck, J P Van de Merwe. Effect of a soluble bacterial carbohydrate fraction on the viscosity of intestinal contents in healthy subjects and patients with Crohn's disease. European journal of clinical investigation. 1989 Feb; 19(1):61-4. doi: 10.1111/j.1365-2362.1989.tb00196.x. [PMID: 2499463]
  • D Ljevaković, S Tomić, J Tomasić. Selective pivaloylation of 2-acetamido-2-deoxy sugars. Carbohydrate research. 1988 Nov; 182(2):197-205. doi: 10.1016/0008-6215(88)84003-5. [PMID: 3242804]
  • S J Giovannoni, W Godchaux, E Schabtach, R W Castenholz. Cell wall and lipid composition of Isosphaera pallida, a budding eubacterium from hot springs. Journal of bacteriology. 1987 Jun; 169(6):2702-7. doi: 10.1128/jb.169.6.2702-2707.1987. [PMID: 3584067]
  • N Watanabe. Amperometric detection of muramic acid in high-performance liquid chromatography with a post-column reaction. Journal of chromatography. 1984 Dec; 316(?):495-500. doi: 10.1016/s0021-9673(00)96177-6. [PMID: 6530424]
  • Z Sen, M L Karnovsky. Qualitative detection of muramic acid in normal mammalian tissues. Infection and immunity. 1984 Mar; 43(3):937-41. doi: 10.1128/iai.43.3.937-941.1984. [PMID: 6698613]
  • M J Gehron, J D Davis, G A Smith, D C White. Determination of the gram-positive bacterial content of soils and sediments by analysis of teichoic acid components. Journal of microbiological methods. 1984; 2(?):165-76. doi: 10.1016/0167-7012(84)90005-8. [PMID: 11540813]
  • J R Pappenheimer. Bayliss-Starling Memorial Lecture (1982). Induction of sleep by muramyl peptides. The Journal of physiology. 1983 Mar; 336(?):1-11. doi: 10.1113/jphysiol.1983.sp014561. [PMID: 6875901]
  • T H Maugh. Sleep-promoting factor isolated. Science (New York, N.Y.). 1982 Jun; 216(4553):1400. doi: 10.1126/science.6124035. [PMID: 6124035]
  • M Fevrier, J L Birrien, C Leclerc, L Chedid, P Liacopoulos. The macrophage, target cell of the synthetic adjuvant muramyl dipeptide. European journal of immunology. 1978 Aug; 8(8):558-62. doi: 10.1002/eji.1830080804. [PMID: 359336]
  • L Chedid, F Audibert, P Lefrancier, J Choay, E Lederer. Modulation of the immune response by a synthetic adjuvant and analogs. Proceedings of the National Academy of Sciences of the United States of America. 1976 Jul; 73(7):2472-5. doi: 10.1073/pnas.73.7.2472. [PMID: 1065901]
  • S Kotani, Y Watanabe, T Shimono, K Harada, T Shiba. Correlation between the immunoadjuvant activities and pyrogenicities of synthetic N-acetylmuramyl-peptides or -amino acids. Biken journal. 1976 Mar; 19(1):9-13. doi: NULL. [PMID: 779765]
  • L S Johnston, F C Neuhaus. Initial membrane reaction in the biosynthesis of peptidoglycan. Spin-labeled intermediates as receptors for vancomycin and ristocetin. Biochemistry. 1975 Jun; 14(12):2754-60. doi: 10.1021/bi00683a031. [PMID: 167805]
  • B Z Siegel, S M Siegel. The chemical composition of algal cell walls. CRC critical reviews in microbiology. 1973 Sep; 3(1):1-26. doi: 10.3109/10408417309108743. [PMID: 4356878]
  • R A Morton. Polyprenols, their nature, occurrence and biological roles. Biochemical Society symposium. 1972; ?(35):203-17. doi: NULL. [PMID: 4614801]
  • E Lederer. Correlation of chemical structure and biological activity of mycobacterial cell walls and derived lipids. Biochemical Society symposium. 1972; ?(35):321-31. doi: ". [PMID: 4614808]