Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2019-04-04 16:09:12 UTC |
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Update Date | 2022-09-22 18:34:32 UTC |
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HMDB ID | HMDB0240343 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | N-Acetylmethionine sulfoxide |
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Description | N-Acetylmethionine sulfoxide (CAS: 3054-51-1), also known as N-ACMSO or 2-(acetylamino)-4-(methylsulfinyl)butanoic acid, belongs to the class of organic compounds known as N-acyl-L-alpha-amino acids. These are N-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. N-Acetylmethionine sulfoxide has been identified in the human placenta (PMID: 32033212 ). |
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Structure | CC(=O)N[C@@H](CCS(C)=O)C(O)=O InChI=1S/C7H13NO4S/c1-5(9)8-6(7(10)11)3-4-13(2)12/h6H,3-4H2,1-2H3,(H,8,9)(H,10,11)/t6-,13?/m0/s1 |
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Synonyms | Value | Source |
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(2S)-2-[(1-Hydroxyethylidene)amino]-4-methanesulfinylbutanoate | Generator | (2S)-2-[(1-Hydroxyethylidene)amino]-4-methanesulphinylbutanoate | Generator | (2S)-2-[(1-Hydroxyethylidene)amino]-4-methanesulphinylbutanoic acid | Generator | N-ACMSO | MeSH | N-Acetylmethionine sulfoxide | MeSH | (2S)-2-(Acetylamino)-4-(methylsulfinyl)butanoic acid | HMDB | (2S)-2-Acetamido-4-(methylsulfinyl)butanoic acid | HMDB | (2S)-2-Acetamido-4-methanesulfinylbutanoic acid | HMDB | (2S)-2-Acetamido-4-methylsulfinylbutanoic acid | HMDB | 2-(Acetylamino)-4-(methylsulfinyl)butanoic acid | HMDB | N-Acetyl-L-methionine sulfoxide | HMDB |
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Chemical Formula | C7H13NO4S |
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Average Molecular Weight | 207.24 |
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Monoisotopic Molecular Weight | 207.056529077 |
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IUPAC Name | (2S)-2-acetamido-4-methanesulfinylbutanoic acid |
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Traditional Name | (2S)-2-acetamido-4-methanesulfinylbutanoic acid |
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CAS Registry Number | 108646-71-5 |
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SMILES | CC(=O)N[C@@H](CCS(C)=O)C(O)=O |
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InChI Identifier | InChI=1S/C7H13NO4S/c1-5(9)8-6(7(10)11)3-4-13(2)12/h6H,3-4H2,1-2H3,(H,8,9)(H,10,11)/t6-,13?/m0/s1 |
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InChI Key | NPIMMZJBURSMON-YLTHGKPTSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | N-acyl-L-alpha-amino acids |
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Alternative Parents | |
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Substituents | - N-acyl-l-alpha-amino acid
- Thia fatty acid
- Fatty acid
- Fatty acyl
- Acetamide
- Carboxamide group
- Secondary carboxylic acid amide
- Sulfoxide
- Sulfinyl compound
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Organic oxygen compound
- Carbonyl group
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Hydrocarbon derivative
- Organic nitrogen compound
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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N-Acetylmethionine sulfoxide,1TMS,isomer #1 | CC(=O)N[C@@H](CCS(C)=O)C(=O)O[Si](C)(C)C | 1734.6 | Semi standard non polar | 33892256 | N-Acetylmethionine sulfoxide,1TMS,isomer #2 | CC(=O)N([C@@H](CCS(C)=O)C(=O)O)[Si](C)(C)C | 1736.6 | Semi standard non polar | 33892256 | N-Acetylmethionine sulfoxide,2TMS,isomer #1 | CC(=O)N([C@@H](CCS(C)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1754.9 | Semi standard non polar | 33892256 | N-Acetylmethionine sulfoxide,2TMS,isomer #1 | CC(=O)N([C@@H](CCS(C)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 2073.8 | Standard non polar | 33892256 | N-Acetylmethionine sulfoxide,2TMS,isomer #1 | CC(=O)N([C@@H](CCS(C)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 2133.5 | Standard polar | 33892256 | N-Acetylmethionine sulfoxide,1TBDMS,isomer #1 | CC(=O)N[C@@H](CCS(C)=O)C(=O)O[Si](C)(C)C(C)(C)C | 1963.9 | Semi standard non polar | 33892256 | N-Acetylmethionine sulfoxide,1TBDMS,isomer #2 | CC(=O)N([C@@H](CCS(C)=O)C(=O)O)[Si](C)(C)C(C)(C)C | 1967.9 | Semi standard non polar | 33892256 | N-Acetylmethionine sulfoxide,2TBDMS,isomer #1 | CC(=O)N([C@@H](CCS(C)=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2240.7 | Semi standard non polar | 33892256 | N-Acetylmethionine sulfoxide,2TBDMS,isomer #1 | CC(=O)N([C@@H](CCS(C)=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2615.3 | Standard non polar | 33892256 | N-Acetylmethionine sulfoxide,2TBDMS,isomer #1 | CC(=O)N([C@@H](CCS(C)=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2347.1 | Standard polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - N-Acetylmethionine sulfoxide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Acetylmethionine sulfoxide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetylmethionine sulfoxide 10V, Positive-QTOF | splash10-014i-0910000000-93ffaabee484f7cd67a4 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetylmethionine sulfoxide 20V, Positive-QTOF | splash10-0f6t-7900000000-0ea877575dff1139e961 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetylmethionine sulfoxide 40V, Positive-QTOF | splash10-03di-9100000000-7b0e97a852e51236a59b | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetylmethionine sulfoxide 10V, Negative-QTOF | splash10-03di-7950000000-3b5c400fe303c2551109 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetylmethionine sulfoxide 20V, Negative-QTOF | splash10-03di-9400000000-3b4399cf013a7bb28812 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetylmethionine sulfoxide 40V, Negative-QTOF | splash10-01ox-9000000000-87fb4d29772a0579d39c | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Cancer patients undergoing total body irradiation | | details | Urine | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Cancer patients undergoing total body irradiation | | details |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 19354090 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | Not Available |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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