Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2005-11-16 15:48:42 UTC |
---|
Update Date | 2023-02-21 17:15:08 UTC |
---|
HMDB ID | HMDB0000747 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Isovalerylalanine |
---|
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. |
---|
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 |
---|
Synonyms | Value | Source |
---|
(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 |
|
---|
Chemical Formula | C8H15NO3 |
---|
Average Molecular Weight | 173.2096 |
---|
Monoisotopic Molecular Weight | 173.105193351 |
---|
IUPAC Name | (2S)-2-(3-methylbutanamido)propanoic acid |
---|
Traditional Name | isovalerylalanine |
---|
CAS Registry Number | 68219-63-6 |
---|
SMILES | CC(C)CC(=O)N[C@@H](C)C(O)=O |
---|
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 |
---|
InChI Key | OJPSNARFDYTAEN-LURJTMIESA-N |
---|
Chemical Taxonomy |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic acids and derivatives |
---|
Class | Carboxylic acids and derivatives |
---|
Sub Class | Amino acids, peptides, and analogues |
---|
Direct Parent | N-acyl-L-alpha-amino acids |
---|
Alternative Parents | |
---|
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
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | Not Available |
---|
Role | Not Available |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
Isovalerylalanine,1TMS,isomer #1 | CC(C)CC(=O)N[C@@H](C)C(=O)O[Si](C)(C)C | 1453.1 | Semi standard non polar | 33892256 | Isovalerylalanine,1TMS,isomer #2 | CC(C)CC(=O)N([C@@H](C)C(=O)O)[Si](C)(C)C | 1477.4 | Semi standard non polar | 33892256 | Isovalerylalanine,2TMS,isomer #1 | CC(C)CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1490.0 | Semi standard non polar | 33892256 | Isovalerylalanine,2TMS,isomer #1 | CC(C)CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1479.7 | Standard non polar | 33892256 | Isovalerylalanine,2TMS,isomer #1 | CC(C)CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1579.8 | Standard polar | 33892256 | Isovalerylalanine,1TBDMS,isomer #1 | CC(C)CC(=O)N[C@@H](C)C(=O)O[Si](C)(C)C(C)(C)C | 1688.3 | Semi standard non polar | 33892256 | Isovalerylalanine,1TBDMS,isomer #2 | CC(C)CC(=O)N([C@@H](C)C(=O)O)[Si](C)(C)C(C)(C)C | 1704.1 | Semi standard non polar | 33892256 | Isovalerylalanine,2TBDMS,isomer #1 | CC(C)CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 1958.2 | Semi standard non polar | 33892256 | Isovalerylalanine,2TBDMS,isomer #1 | CC(C)CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 1909.1 | Standard non polar | 33892256 | Isovalerylalanine,2TBDMS,isomer #1 | CC(C)CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 1901.3 | Standard polar | 33892256 |
|
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylalanine GC-MS (Non-derivatized) - 70eV, Positive | splash10-000f-9200000000-0941d93d8b73095be371 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylalanine GC-MS (1 TMS) - 70eV, Positive | splash10-00bl-9310000000-ff31ec8bcd2f767edd93 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylalanine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylalanine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylalanine GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylalanine GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylalanine GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylalanine 10V, Positive-QTOF | splash10-05i0-4900000000-279a1567e1a63ff40f7b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylalanine 20V, Positive-QTOF | splash10-0006-9200000000-75f940b78c284e853b5c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylalanine 40V, Positive-QTOF | splash10-0a4l-9000000000-84fea44c8d0eeaff9059 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylalanine 10V, Negative-QTOF | splash10-00di-1900000000-c44e3552766c93b10335 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylalanine 20V, Negative-QTOF | splash10-0fki-7900000000-1dbfe9bbc6b7b04d91a6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylalanine 40V, Negative-QTOF | splash10-05g3-9000000000-f37b9b82877a21760d9f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylalanine 10V, Negative-QTOF | splash10-000i-9300000000-bf002906104d17589e4f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylalanine 20V, Negative-QTOF | splash10-000i-9000000000-eee2c525ead39ccdd1b1 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylalanine 40V, Negative-QTOF | splash10-000f-9000000000-8f8a6b36163eb8d3cef2 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylalanine 10V, Positive-QTOF | splash10-0006-9200000000-ac4c7b8b294dbcda8355 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylalanine 20V, Positive-QTOF | splash10-0006-9000000000-49ba66e461e13d06ddf7 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylalanine 40V, Positive-QTOF | splash10-0006-9000000000-7987039666b0de647c54 | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Experimental 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
|
---|
Synthesis Reference | Chen, Shu-Hui; Lamar, Jason; Guo, Deqi; Kohn, Todd; Yang, Hsiu-Chiung; McGee, James; Timm, David; Erickson, Jon; Yip, Yvonne; May, Patrick; McCarthy, James. P3 cap modified Phe*-Ala series BACE inhibitors. Bioorganic & Medicinal Chemistry Letters (2004), 14(1), 245-250. |
---|