Record Information |
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Version | 1.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2021-08-16 18:04:07 UTC |
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NP-MRD ID | NP0000588 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Isovalerylalanine |
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Description | Isovalerylalanine, also known as isopentanoylalanine, 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. Isovalerylalanine results from the formal condensation of the carboxy group of isovaleric acid with the amino group of L-alanine. Isovalerylalanine is one of the constituents of the organic acid profile in isovaleric acidemia, it is believed to be formed by the action of the enzyme glycine N-acylase on alanine, using isovaleryl-CoA as a substrate (PMID: 6197208 ). Isovaleric acidemia was the first organic acid acidemia to be documented in humans. It is an autosomal recessive inborn error in the metabolism of leucine, caused by a deficiency of the mitochondrial enzyme isovaleryl-CoA dehydrogenase (IVD) that results in the accumulation isovaleryl-CoA derivatives (PMID: 16602101). The excess of isovaleryl-CoA in plasma allows for the formation of condensation derivatives, such as isovalerylalanine which makes it one of the biomarkers for this condition. |
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Structure | CC(C)CC(=O)N[C@@H](C)C(O)=O InChI=1S/C8H15NO3/c1-5(2)4-7(10)9-6(3)8(11)12/h5-6H,4H2,1-3H3,(H,9,10)(H,11,12)/t6-/m0/s1 |
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Synonyms | Value | Source |
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(2S)-2-(3-Methylbutanamido)propanoic acid | ChEBI | Isopentanoylalanine | ChEBI | N-Isopentanoyl-L-alanine | ChEBI | N-Isopentanoylalanine | ChEBI | N-Isovalerylalanine | ChEBI | (2S)-2-(3-Methylbutanamido)propanoate | Generator | N-Isovaleryl-L-alanine | HMDB | Isovalerylalanine | ChEBI |
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Chemical Formula | C8H15NO3 |
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Average Mass | 173.2096 Da |
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Monoisotopic Mass | 173.10519 Da |
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IUPAC Name | (2S)-2-(3-methylbutanamido)propanoic acid |
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Traditional Name | isovalerylalanine |
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CAS Registry Number | 68219-63-6 |
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SMILES | CC(C)CC(=O)N[C@@H](C)C(O)=O |
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InChI Identifier | InChI=1S/C8H15NO3/c1-5(2)4-7(10)9-6(3)8(11)12/h5-6H,4H2,1-3H3,(H,9,10)(H,11,12)/t6-/m0/s1 |
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InChI Key | OJPSNARFDYTAEN-LURJTMIESA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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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
- Alanine or derivatives
- Fatty amide
- N-acyl-amine
- Fatty acyl
- Carboxamide group
- Secondary carboxylic acid amide
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Hydrocarbon derivative
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Organic oxygen compound
- Organic oxide
- Organopnictogen 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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Physical Properties |
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State | Solid |
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Experimental 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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Predicted Properties | |
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General References | - Lehnert W: N-Isovalerylalanine and N-isovalerylsarcosine: two new minor metabolites in isovaleric acidemia. Clin Chim Acta. 1983 Oct 31;134(1-2):207-12. [PubMed:6197208 ]
- Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Patient Version. 2002. [PubMed:34403226 ]
- Authors unspecified: Thyroid Cancer Screening (PDQ(R)): Health Professional Version. 2002. [PubMed:28876831 ]
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- Karikalan M, Chander V, Mahajan S, Deol P, Agrawal RK, Nandi S, Rai SK, Mathur A, Pawde A, Singh KP, Sharma GK: Natural infection of Delta mutant of SARS-CoV-2 in Asiatic Lions of India. Transbound Emerg Dis. 2021 Aug 17. doi: 10.1111/tbed.14290. [PubMed:34404118 ]
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