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 16:08:50 UTC |
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Update Date | 2022-09-22 17:44:16 UTC |
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HMDB ID | HMDB0240341 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | N-Acetyl-3-methylhistidine |
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Description | N-Acetyl-3-methylhistidine, an N-acetyl-L-amino acid, belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing histidine or a derivative thereof resulting from a reaction of histidine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-Acetyl-3-methylhistidine is an acetylated derivative of 3-methylhistidine and a very strong basic compound (based on its pKa). N-Acetyl-3-methylhistidine has been found to be associated with prostate cancer (PMID: 28423352 ). |
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Structure | CN1C=NC=C1C[C@H](NC(C)=O)C(O)=O InChI=1S/C9H13N3O3/c1-6(13)11-8(9(14)15)3-7-4-10-5-12(7)2/h4-5,8H,3H2,1-2H3,(H,11,13)(H,14,15)/t8-/m0/s1 |
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Synonyms | Value | Source |
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(2S)-2-Acetamido-3-(1-methyl-1H-imidazol-5-yl)propanoic acid | HMDB | (2S)-2-Acetamido-3-(1-methyl-1H-imidazol-5-yl)propionic acid | HMDB | N-Acetyl-3-methyl-L-histidine | HMDB | N-Acetyl-L-3-methylhistidine | HMDB | N-Acetyl-3-methylhistidine | HMDB |
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Chemical Formula | C9H13N3O3 |
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Average Molecular Weight | 211.221 |
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Monoisotopic Molecular Weight | 211.095691291 |
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IUPAC Name | (2S)-2-acetamido-3-(1-methyl-1H-imidazol-5-yl)propanoic acid |
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Traditional Name | (2S)-2-acetamido-3-(3-methylimidazol-4-yl)propanoic acid |
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CAS Registry Number | 37841-04-6 |
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SMILES | CN1C=NC=C1C[C@H](NC(C)=O)C(O)=O |
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InChI Identifier | InChI=1S/C9H13N3O3/c1-6(13)11-8(9(14)15)3-7-4-10-5-12(7)2/h4-5,8H,3H2,1-2H3,(H,11,13)(H,14,15)/t8-/m0/s1 |
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InChI Key | FKTXRTPBUWLETL-QMMMGPOBSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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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 | Histidine and derivatives |
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Alternative Parents | |
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Substituents | - Histidine or derivatives
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- N-acyl-l-alpha-amino acid
- Imidazolyl carboxylic acid derivative
- N-substituted imidazole
- Azole
- Imidazole
- Acetamide
- Heteroaromatic compound
- Secondary carboxylic acid amide
- Carboxamide group
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Azacycle
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Organic nitrogen compound
- Organic oxide
- Carbonyl group
- Organopnictogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Not Available | 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 SectionsPredictor | Adduct Type | CCS Value (Å2) | Reference |
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DeepCCS | [M+H]+ | 141.406 | 30932474 | DeepCCS | [M-H]- | 139.048 | 30932474 | DeepCCS | [M-2H]- | 174.277 | 30932474 | DeepCCS | [M+Na]+ | 149.531 | 30932474 |
Predicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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N-Acetyl-3-methylhistidine,1TMS,isomer #1 | CC(=O)N[C@@H](CC1=CN=CN1C)C(=O)O[Si](C)(C)C | 2034.5 | Semi standard non polar | 33892256 | N-Acetyl-3-methylhistidine,1TMS,isomer #2 | CC(=O)N([C@@H](CC1=CN=CN1C)C(=O)O)[Si](C)(C)C | 2002.2 | Semi standard non polar | 33892256 | N-Acetyl-3-methylhistidine,2TMS,isomer #1 | CC(=O)N([C@@H](CC1=CN=CN1C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 2009.7 | Semi standard non polar | 33892256 | N-Acetyl-3-methylhistidine,2TMS,isomer #1 | CC(=O)N([C@@H](CC1=CN=CN1C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1992.0 | Standard non polar | 33892256 | N-Acetyl-3-methylhistidine,2TMS,isomer #1 | CC(=O)N([C@@H](CC1=CN=CN1C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 2475.3 | Standard polar | 33892256 | N-Acetyl-3-methylhistidine,1TBDMS,isomer #1 | CC(=O)N[C@@H](CC1=CN=CN1C)C(=O)O[Si](C)(C)C(C)(C)C | 2296.2 | Semi standard non polar | 33892256 | N-Acetyl-3-methylhistidine,1TBDMS,isomer #2 | CC(=O)N([C@@H](CC1=CN=CN1C)C(=O)O)[Si](C)(C)C(C)(C)C | 2259.4 | Semi standard non polar | 33892256 | N-Acetyl-3-methylhistidine,2TBDMS,isomer #1 | CC(=O)N([C@@H](CC1=CN=CN1C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2489.2 | Semi standard non polar | 33892256 | N-Acetyl-3-methylhistidine,2TBDMS,isomer #1 | CC(=O)N([C@@H](CC1=CN=CN1C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2453.8 | Standard non polar | 33892256 | N-Acetyl-3-methylhistidine,2TBDMS,isomer #1 | CC(=O)N([C@@H](CC1=CN=CN1C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2652.3 | 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-Acetyl-3-methylhistidine 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-Acetyl-3-methylhistidine 10V, Negative-QTOF | splash10-014i-2920000000-aced5e819643bac5715d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-3-methylhistidine 20V, Negative-QTOF | splash10-0pb9-6910000000-4ef054c99d313da2b859 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-3-methylhistidine 40V, Negative-QTOF | splash10-0536-9100000000-75f3b2e0f85194d6fcff | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-3-methylhistidine 10V, Positive-QTOF | splash10-03di-0890000000-43c6d11dc317f14bbcdb | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-3-methylhistidine 20V, Positive-QTOF | splash10-0fk9-1900000000-e92aed51b6356c6b5bf9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-3-methylhistidine 40V, Positive-QTOF | splash10-0592-8900000000-46c61afa915f97c0888d | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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 | Predicted 1D NMR | 1H 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 | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Adult (40 years old) | Both | Normal | | details | 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 | Detected but not Quantified | Not Quantified | Elderly (>65 years old) | Male | Renal failure with dialysis | | 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 | 167717 |
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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 | 193270 |
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PDB ID | Not Available |
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ChEBI ID | 133183 |
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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 | - Huang J, Mondul AM, Weinstein SJ, Karoly ED, Sampson JN, Albanes D: Prospective serum metabolomic profile of prostate cancer by size and extent of primary tumor. Oncotarget. 2017 Jul 11;8(28):45190-45199. doi: 10.18632/oncotarget.16775. [PubMed:28423352 ]
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