| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-05-26 05:49:40 UTC |
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| Update Date | 2016-11-09 01:21:19 UTC |
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| Accession Number | CHEM035504 |
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| Identification |
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| Common Name | Muramic acid |
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| Class | Small Molecule |
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| Description | |
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| Contaminant Sources | |
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| Contaminant Type | Not Available |
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| Muramate | Generator | | (+)-Muramate | HMDB | | (+)-Muramic acid | HMDB | | 3-O-alpha-Carboxyethyl-D-glucosamine | HMDB | | 3-O-alpha-Carboxyethyl-delta-glucosamine | HMDB | | Muramic acid hydrate | HMDB | | Murexide | HMDB | | (2R)-2-{[(2R,3R,4S,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoate | Generator, HMDB |
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| Chemical Formula | C9H17NO7 |
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| Average Molecular Mass | 251.234 g/mol |
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| Monoisotopic Mass | 251.101 g/mol |
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| CAS Registry Number | 1114-41-6 |
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| IUPAC Name | (2R)-2-{[(2R,3R,4S,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid |
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| Traditional Name | (2R)-2-{[(2R,3R,4S,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid |
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| SMILES | C[C@@H](O[C@H]1[C@@H](N)[C@H](O)O[C@H](CO)[C@H]1O)C(O)=O |
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| InChI Identifier | 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 |
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| InChI Key | MSFSPUZXLOGKHJ-LEISLEKSSA-N |
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| Chemical Taxonomy |
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| Description | 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Carbohydrates and carbohydrate conjugates |
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| Direct Parent | Sugar acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Muramic_acid
- Hexose monosaccharide
- Amino saccharide
- Sugar acid
- Monosaccharide
- Oxane
- Amino acid or derivatives
- Hemiacetal
- Amino acid
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Dialkyl ether
- Ether
- Monocarboxylic acid or derivatives
- Oxacycle
- Organoheterocyclic compound
- Primary aliphatic amine
- Organic oxide
- Organopnictogen compound
- Organic nitrogen compound
- Amine
- Carbonyl group
- Hydrocarbon derivative
- Organonitrogen compound
- Alcohol
- Primary alcohol
- Primary amine
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | Not Available |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Not Available |
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| Cellular Locations | Not Available |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Appearance | Not Available |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-003r-9520000000-91bf5f5e77865f5b146f | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-00fr-5722490000-e41bf810e5d7a6b7be4b | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0f89-0190000000-d990980701f630613360 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01q9-5950000000-a7012f82e4f7a8356db2 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01xx-9500000000-9b72e362c6da0556143a | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udr-7390000000-24dfc3347bddf790ce96 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0019-9830000000-eac28b7b8efa7e1d642a | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-007d-9400000000-8a1ef61dfc5b55d91d45 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9000000000-8ffd847778e88673df79 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-007c-9000000000-bb66080cf35469c7116f | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000f-9000000000-dec404b78b57490bbf3a | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0ue9-0190000000-2826fd1498ec2b1ac21d | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0il0-2940000000-9cd55fcc2e559c11de76 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fxx-9800000000-6d882558ee7ae32f13f8 | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | Not Available |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | Not Available |
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| Uses/Sources | Not Available |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB0003254 |
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| FooDB ID | FDB023131 |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | C00019555 |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | 3381 |
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| PDB ID | Not Available |
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| Wikipedia Link | Muramic acid |
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| Chemspider ID | 17216223 |
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| ChEBI ID | 28118 |
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| PubChem Compound ID | 22833605 |
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| Kegg Compound ID | C06470 |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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| General References | | 1. Kozar MP, Krahmer MT, Fox A, Gray BM: Failure To detect muramic acid in normal rat tissues but detection in cerebrospinal fluids from patients with Pneumococcal meningitis. Infect Immun. 2000 Aug;68(8):4688-98. | | 2. Fox A, Fox K, Christensson B, Harrelson D, Krahmer M: Absolute identification of muramic acid, at trace levels, in human septic synovial fluids in vivo and absence in aseptic fluids. Infect Immun. 1996 Sep;64(9):3911-5. | | 3. Christensson B, Gilbart J, Fox A, Morgan SL: Mass spectrometric quantitation of muramic acid, a bacterial cell wall component, in septic synovial fluids. Arthritis Rheum. 1989 Oct;32(10):1268-72. | | 4. Mollner S, Braun V: Murein hydrolase (N-acetyl-muramyl-L-alanine amidase) in human serum. Arch Microbiol. 1984 Dec;140(2-3):171-7. | | 5. Chen T, Rimpilainen M, Luukkainen R, Mottonen T, Yli-Jama T, Jalava J, Vainio O, Toivanen P: Bacterial components in the synovial tissue of patients with advanced rheumatoid arthritis or osteoarthritis: analysis with gas chromatography-mass spectrometry and pan-bacterial polymerase chain reaction. Arthritis Rheum. 2003 Jun 15;49(3):328-34. | | 6. Hoijer MA, Melief MJ, van Helden-Meeuwsen CG, Eulderink F, Hazenberg MP: Detection of muramic acid in a carbohydrate fraction of human spleen. Infect Immun. 1995 May;63(5):1652-7. | | 7. Bal K, Larsson L: New and simple procedure for the determination of muramic acid in chemically complex environments by gas chromatography-ion trap tandem mass spectrometry. J Chromatogr B Biomed Sci Appl. 2000 Jan 28;738(1):57-65. |
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