UDP-N-acetylmuraminate (BioDeep_00000004552)
Secondary id: BioDeep_00001870050
human metabolite Endogenous
代谢物信息卡片
(2r)-2-{[(2r,3r,4r,5s,6r)-3-(Acetylamino)-2-{[(S)-{[(R)-{[(2r,3s,4r,5r)-5-(2,4-Dioxo-3,4-Dihydropyrimidin-1(2h)-Yl)-3,4-Dihydroxytetrahydrofuran-2-Yl]methoxy}(Hydroxy)phosphoryl]oxy}(Hydroxy)phosphoryl]oxy}-5-Hydroxy-6-(Hydroxymethyl)tetrahydro-2h-Pyran-4-Yl]oxy}propanoic Acid
化学式: C20H31N3O19P2 (679.1027)
中文名称: UDP-N-乙酰胞壁酸
谱图信息:
最多检出来源 Homo sapiens(otcml) 3.72%
Reviewed
Last reviewed on 2024-12-16.
Cite this Page
UDP-N-acetylmuraminate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China.
https://query.biodeep.cn/s/udp-n-acetylmuraminate (retrieved
2024-12-22) (BioDeep RN: BioDeep_00000004552). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
分子结构信息
SMILES: CC(=O)NC1C(OP(=O)(O)OP(=O)(O)OCC2OC(n3ccc(O)nc3=O)C(O)C2O)OC(CO)C(O)C1OC(C)C(=O)O
InChI: InChI=1S/C20H31N3O19P2/c1-7(18(30)31)38-16-12(21-8(2)25)19(40-9(5-24)14(16)28)41-44(35,36)42-43(33,34)37-6-10-13(27)15(29)17(39-10)23-4-3-11(26)22-20(23)32/h3-4,7,9-10,12-17,19,24,27-29H,5-6H2,1-2H3,(H,21,25)(H,30,31)(H,33,34)(H,35,36)(H,22,26,32)
描述信息
UDP-N-acetylmuraminate is a nucleoside diphosphate sugar which is formed from UDP-N-acetylglucosamine and phosphoenolpyruvate. It serves as the building block upon which peptidoglycan is formed.
UDP-N-acetylmuraminate, also known as UDP-MurNAc, is a key molecule in the biosynthesis of bacterial cell walls. It is a nucleotide sugar, which means it consists of a nucleotide (uridine diphosphate, UDP) linked to a sugar molecule (N-acetylmuramic acid, MurNAc). This compound plays a critical role in the formation of peptidoglycan, the essential structural component of the bacterial cell wall.
Here are some key points about UDP-N-acetylmuraminate:
Biosynthesis: UDP-MurNAc is synthesized from UDP-N-acetylglucosamine (UDP-GlcNAc) through a series of enzymatic reactions. The addition of a lactyl group to UDP-GlcNAc forms UDP-MurNAc.
Peptidoglycan Precursor: It serves as a precursor for the synthesis of peptidoglycan, which is a polymer made up of alternating units of N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc). The peptide chains attached to MurNAc units cross-link to provide structural strength to the cell wall.
Enzymatic Processing: UDP-MurNAc is further processed by enzymes such as Mur synthases, which add amino acids to form the pentapeptide chain attached to the MurNAc residue. This pentapeptide is crucial for the cross-linking of peptidoglycan layers.
Target for Antibiotics: Since peptidoglycan synthesis is unique to bacteria, enzymes involved in the biosynthesis and processing of UDP-MurNAc are targets for antibiotics. Inhibiting these enzymes can prevent proper cell wall formation, leading to bacterial cell death.
Importance in Bacterial Growth: The availability of UDP-MurNAc is essential for bacterial growth and cell division, as it is a direct precursor to the building blocks of the cell wall.
Research and Applications: Understanding the biosynthesis and function of UDP-MurNAc is important for developing new antibiotics, as well as for basic research in bacterial cell biology.
UDP-N-acetylmuraminate is a vital molecule in the construction of the bacterial cell wall, and its biosynthesis and function are of significant interest in both basic research and the development of antibacterial therapies.
A nucleoside diphosphate sugar which is formed from UDP-N-acetylglucosamine and phosphoenolpyruvate. It serves as the building block upon which peptidoglycan is formed [HMDB]
同义名列表
12 个代谢物同义名
(2r)-2-{[(2r,3r,4r,5s,6r)-3-(Acetylamino)-2-{[(S)-{[(R)-{[(2r,3s,4r,5r)-5-(2,4-Dioxo-3,4-Dihydropyrimidin-1(2h)-Yl)-3,4-Dihydroxytetrahydrofuran-2-Yl]methoxy}(Hydroxy)phosphoryl]oxy}(Hydroxy)phosphoryl]oxy}-5-Hydroxy-6-(Hydroxymethyl)tetrahydro-2h-Pyran-4-Yl]oxy}propanoic Acid; 2-{[2-({[({[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid; 2-({2-[({[5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl}oxy)propanoic acid; Uridine diphosphate N-acetylmuramic acid; Uridine diphospho-N-acetylmuramic acid; UDP-N-Acetylmuraminic acid; UDP-N-acetylmuramic acid; UDP-N-Acetyl-D-muramate; UDP-N-acetylmuraminate; N-Acetylmuramoyl-UDP; UDP-N-Acetylmuramate; UDP-MurNAc
数据库引用编号
16 个数据库交叉引用编号
- ChEBI: CHEBI:88385
- ChEBI: CHEBI:70765
- KEGG: C01050
- PubChem: 1169
- HMDB: HMDB0011720
- Metlin: METLIN62452
- MeSH: Uridine Diphosphate N-Acetylmuramic Acid
- KNApSAcK: C00019555
- foodb: FDB028404
- chemspider: 1136
- CAS: 18867-75-9
- PMhub: MS000017070
- PDB-CCD: EPZ
- 3DMET: B04759
- NIKKAJI: J710.466I
- RefMet: UDP-N-acetylmuramic acid
分类词条
相关代谢途径
Reactome(0)
BioCyc(2)
PlantCyc(0)
代谢反应
6 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(3)
- peptidoglycan and lipid A precursor biosynthesis:
ATP + UDP-N-acetylmuramate + ala ⟶ ADP + H+ + UDP-N-acetylmuramyl-L-Ala + phosphate - peptidoglycan biosynthesis I (meso-diaminopimelate containing):
ATP + UDP-N-acetylmuramate + ala ⟶ ADP + H+ + UDP-N-acetylmuramyl-L-Ala + phosphate - UDP-N-acetylmuramoyl-pentapeptide biosynthesis III (meso-DAP-containing):
ATP + UDP-N-acetylmuramate + ala ⟶ ADP + H+ + UDP-N-acetylmuramyl-L-Ala + phosphate
WikiPathways(1)
- Peptidoglycan cytoplasmic synthesis and recycling pathways:
D-glucosamine-6-phosphate ⟶ Fructose-6-phosphate
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(2)
- D-Glutamine and D-Glutamate Metabolism:
L-Glutamine + Water ⟶ Ammonia + L-Glutamic acid - D-Glutamine and D-Glutamate Metabolism:
L-Glutamine + Water ⟶ Ammonia + L-Glutamic acid
PharmGKB(0)
1 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
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Biochemistry.
2017 09; 56(37):4992-5001. doi:
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Natural product reports.
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Journal of bioscience and bioengineering.
2017 Mar; 123(3):398-401. doi:
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Scientific reports.
2017 02; 7(?):43306. doi:
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Biochemistry.
2017 01; 56(4):612-622. doi:
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Frontiers in cellular and infection microbiology.
2017; 7(?):353. doi:
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International journal of medical microbiology : IJMM.
2017 Jan; 307(1):1-10. doi:
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Methods in molecular biology (Clifton, N.J.).
2017; 1588(?):59-70. doi:
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Applied microbiology and biotechnology.
2016 Sep; 100(18):7815-25. doi:
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Chemistry (Weinheim an der Bergstrasse, Germany).
2016 Aug; 22(36):12606-16. doi:
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Journal of pharmaceutical and biomedical analysis.
2016 Aug; 127(?):123-8. doi:
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The Journal of biological chemistry.
2016 07; 291(29):15057-68. doi:
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Angewandte Chemie (International ed. in English).
2016 07; 55(29):8401-4. doi:
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Biochemistry.
2016 06; 55(23):3303-14. doi:
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Nature.
2016 05; 533(7604):557-560. doi:
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Biochimica et biophysica acta.
2016 May; 1858(5):958-70. doi:
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Biochimica et biophysica acta.
2016 May; 1858(5):947-57. doi:
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Journal of medicinal chemistry.
2016 Apr; 59(7):3569-74. doi:
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Molecular microbiology.
2016 Apr; 100(1):1-14. doi:
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Journal of industrial microbiology & biotechnology.
2016 Mar; 43(2-3):177-84. doi:
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Scientific reports.
2016 Feb; 6(?):21185. doi:
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The Journal of biological chemistry.
2016 Jan; 291(5):2535-46. doi:
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Biochemistry.
2016 Jan; 55(1):232-7. doi:
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Journal of medicinal chemistry.
2015 Dec; 58(24):9712-21. doi:
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Biochimica et biophysica acta.
2015 Nov; 1848(11 Pt B):3062-71. doi:
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Applied and environmental microbiology.
2015 Aug; 81(16):5335-43. doi:
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Journal of the American Chemical Society.
2015 Jul; 137(29):9382-9. doi:
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Organic & biomolecular chemistry.
2015 Jun; 13(21):5997-6009. doi:
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Proceedings of the National Academy of Sciences of the United States of America.
2015 May; 112(20):6437-42. doi:
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International journal of medical microbiology : IJMM.
2015 Feb; 305(2):190-5. doi:
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Antimicrobial agents and chemotherapy.
2015; 59(6):3683-6. doi:
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Drug design, development and therapy.
2015; 9(?):2383-94. doi:
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Journal of bacteriology.
2014 Dec; 196(23):4111-9. doi:
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Journal of the American Chemical Society.
2014 Oct; 136(42):14678-81. doi:
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Journal of the American Chemical Society.
2014 Aug; 136(31):10874-7. doi:
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Microbiology (Reading, England).
2014 Aug; 160(Pt 8):1628-1636. doi:
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Angewandte Chemie (International ed. in English).
2014 Jul; 53(31):8060-5. doi:
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Science (New York, N.Y.).
2014 Jul; 345(6193):220-2. doi:
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Glycobiology.
2014 Jun; 24(6):564-76. doi:
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The Journal of biological chemistry.
2014 May; 289(21):14707-18. doi:
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Analytical biochemistry.
2014 May; 452(?):67-75. doi:
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Chemistry (Weinheim an der Bergstrasse, Germany).
2014 Apr; 20(16):4554-8. doi:
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Nature communications.
2014 Apr; 5(?):3578. doi:
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Protein and peptide letters.
2014 Apr; 21(4):336-40. doi:
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PloS one.
2014; 9(7):e102246. doi:
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Drug design, development and therapy.
2014; 8(?):1061-4. doi:
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ACS chemical biology.
2013 Dec; 8(12):2688-96. doi:
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Molecular microbiology.
2013 Dec; 90(5):966-82. doi:
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Journal of the American Chemical Society.
2013 Nov; 135(45):17078-89. doi:
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Molecular microbiology.
2013 Nov; 90(3):502-18. doi:
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The Journal of biological chemistry.
2013 Sep; 288(36):25915-25923. doi:
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