Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2022-09-09 20:34:10 UTC |
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Update Date | 2022-09-22 18:34:49 UTC |
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HMDB ID | HMDB0341345 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | N-Acetyl-DL-leucine |
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Description | Acetylleucine, also known as tanganil, belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Acetylleucine is also being developed as a possible treatment for several neurological disorders by IntraBio Inc. IntraBio is also investigating acetylleucine for the treatment of common inherited and acquired neurological diseases including Lewy body dementia, amyotrophic lateral sclerosis, restless legs syndrome, multiple sclerosis, and migraine Acetylleucine has received orphan drug designations from the U.S. Food & Drug Administration (FDA) and the European Commission. Acetylleucine is an extremely weak basic (essentially neutral) compound (based on its pKa). Acetylleucine is a modified amino acid used in the treatment of vertigo and cerebellar ataxia. Clinical trials with acetylleucine for the treatment of three orphan, fatal, neurodegenerative disorders are underway: Niemann-Pick disease type C, GM2 gangliosidoses (Tay-Sachs and Sandhoff diseases),, and ataxia–telangiectasia. |
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Structure | InChI=1S/C8H15NO3/c1-5(2)4-7(8(11)12)9-6(3)10/h5,7H,4H2,1-3H3,(H,9,10)(H,11,12) |
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Synonyms | Value | Source |
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Tanganil | Kegg | Lasdol | MeSH | N-Acetyl-L-leucine | MeSH | N-Acetylleucine | MeSH | Acetyl-DL-leucine | MeSH | 2-[(1-Hydroxyethylidene)amino]-4-methylpentanoate | Generator |
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Chemical Formula | C8H15NO3 |
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Average Molecular Weight | 173.212 |
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Monoisotopic Molecular Weight | 173.105193347 |
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IUPAC Name | 2-acetamido-4-methylpentanoic acid |
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Traditional Name | acetylleucine |
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CAS Registry Number | Not Available |
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SMILES | CC(C)CC(NC(C)=O)C(O)=O |
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InChI Identifier | InChI=1S/C8H15NO3/c1-5(2)4-7(8(11)12)9-6(3)10/h5,7H,4H2,1-3H3,(H,9,10)(H,11,12) |
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InChI Key | WXNXCEHXYPACJF-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine 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 | Leucine and derivatives |
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Alternative Parents | |
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Substituents | - Leucine or derivatives
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Branched fatty acid
- Methyl-branched fatty acid
- Fatty acyl
- Fatty acid
- Acetamide
- Carboxamide group
- Secondary carboxylic acid amide
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organonitrogen compound
- Organic oxide
- Organopnictogen compound
- Organic nitrogen compound
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- Hydrocarbon derivative
- 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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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 Kovats Retention IndicesNot Available |
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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-DL-leucine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9100000000-4999ecbfbc380c7cad3a | 2017-08-28 | 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-DL-leucine 10V, Positive-QTOF | splash10-00e9-1900000000-a7e7f933b2155a59555c | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-DL-leucine 20V, Positive-QTOF | splash10-001r-9800000000-f0cf22f10972ee728fe4 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-DL-leucine 40V, Positive-QTOF | splash10-0a4i-9100000000-598d0e4c77dbf9794ee1 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-DL-leucine 10V, Negative-QTOF | splash10-00di-1900000000-15626e7c74e213c4fb23 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-DL-leucine 20V, Negative-QTOF | splash10-05ai-4900000000-5a450ad57fd8bd9d9f69 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-DL-leucine 40V, Negative-QTOF | splash10-052f-9200000000-f0db45895855a83c4418 | 2017-07-26 | Wishart Lab | View Spectrum |
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General References | - Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]
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