Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2021-09-14 15:47:52 UTC |
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HMDB ID | HMDB0000726 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Isovalerylglutamic acid |
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Description | Isovalerylglutamic acid is an unusual mtabolite that has been found in the urine of patients with Isovaleric Acidemia due to Isovaleryl-CoA Dehydrogenase Deficiency (OMMBID: The Metabolic and Molecular Bases of Inherited Disease, Ch.93: Branched Chain Organic Acidurias). and in Multiple acyl-Co A dehydrogenation deficiency (MADD) (PMID 6862997 ). Isovalerylglutamate is a biomarker for the consumption of cheese. |
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Structure | CC(C)CC(=O)N[C@@H](CCC(O)=O)C(O)=O InChI=1S/C10H17NO5/c1-6(2)5-8(12)11-7(10(15)16)3-4-9(13)14/h6-7H,3-5H2,1-2H3,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1 |
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Synonyms | Value | Source |
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Isovalerylglutamate | Generator | N-Isovaleryl-DL-glutamate | HMDB | N-Isovaleryl-DL-glutamic acid | HMDB | N-Isovalerylglutamic acid | HMDB | N-IVGA | HMDB | (2S)-2-[(1-Hydroxy-3-methylbutylidene)amino]pentanedioate | HMDB |
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Chemical Formula | C10H17NO5 |
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Average Molecular Weight | 231.2457 |
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Monoisotopic Molecular Weight | 231.110672659 |
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IUPAC Name | (2S)-2-(3-methylbutanamido)pentanedioic acid |
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Traditional Name | isovalerylglutamic acid |
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CAS Registry Number | 80154-63-8 |
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SMILES | CC(C)CC(=O)N[C@@H](CCC(O)=O)C(O)=O |
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InChI Identifier | InChI=1S/C10H17NO5/c1-6(2)5-8(12)11-7(10(15)16)3-4-9(13)14/h6-7H,3-5H2,1-2H3,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1 |
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InChI Key | HCVIJONZMYVLAW-ZETCQYMHSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid 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 | Glutamic acid and derivatives |
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Alternative Parents | |
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Substituents | - Glutamic acid or derivatives
- N-acyl-l-alpha-amino acid
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Branched fatty acid
- Dicarboxylic acid or derivatives
- Fatty amide
- Fatty acyl
- Fatty acid
- N-acyl-amine
- Carboxamide group
- Secondary carboxylic acid amide
- Carboxylic acid
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- 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 | Not Available |
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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 | Solid |
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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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Isovalerylglutamic acid,1TMS,isomer #1 | CC(C)CC(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O | 1909.6 | Semi standard non polar | 33892256 | Isovalerylglutamic acid,1TMS,isomer #2 | CC(C)CC(=O)N[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C | 1901.8 | Semi standard non polar | 33892256 | Isovalerylglutamic acid,1TMS,isomer #3 | CC(C)CC(=O)N([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C | 1905.1 | Semi standard non polar | 33892256 | Isovalerylglutamic acid,2TMS,isomer #1 | CC(C)CC(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1971.9 | Semi standard non polar | 33892256 | Isovalerylglutamic acid,2TMS,isomer #2 | CC(C)CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C | 1945.3 | Semi standard non polar | 33892256 | Isovalerylglutamic acid,2TMS,isomer #3 | CC(C)CC(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1950.4 | Semi standard non polar | 33892256 | Isovalerylglutamic acid,3TMS,isomer #1 | CC(C)CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1981.2 | Semi standard non polar | 33892256 | Isovalerylglutamic acid,3TMS,isomer #1 | CC(C)CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1971.5 | Standard non polar | 33892256 | Isovalerylglutamic acid,3TMS,isomer #1 | CC(C)CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 2099.4 | Standard polar | 33892256 | Isovalerylglutamic acid,1TBDMS,isomer #1 | CC(C)CC(=O)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O | 2152.4 | Semi standard non polar | 33892256 | Isovalerylglutamic acid,1TBDMS,isomer #2 | CC(C)CC(=O)N[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C | 2133.0 | Semi standard non polar | 33892256 | Isovalerylglutamic acid,1TBDMS,isomer #3 | CC(C)CC(=O)N([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C | 2137.6 | Semi standard non polar | 33892256 | Isovalerylglutamic acid,2TBDMS,isomer #1 | CC(C)CC(=O)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2402.7 | Semi standard non polar | 33892256 | Isovalerylglutamic acid,2TBDMS,isomer #2 | CC(C)CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C | 2409.7 | Semi standard non polar | 33892256 | Isovalerylglutamic acid,2TBDMS,isomer #3 | CC(C)CC(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2402.7 | Semi standard non polar | 33892256 | Isovalerylglutamic acid,3TBDMS,isomer #1 | CC(C)CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2619.2 | Semi standard non polar | 33892256 | Isovalerylglutamic acid,3TBDMS,isomer #1 | CC(C)CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2532.3 | Standard non polar | 33892256 | Isovalerylglutamic acid,3TBDMS,isomer #1 | CC(C)CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2519.2 | Standard polar | 33892256 |
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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 - Isovalerylglutamic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-000l-9710000000-d968d94d4e1a6375e82b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (2 TMS) - 70eV, Positive | splash10-00du-9123000000-9bfe7fee7822684dd801 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Isovalerylglutamic acid Quattro_QQQ 10V, N/A-QTOF (Annotated) | splash10-001j-1910000000-19ae59a8eb59a6c5dcf6 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Isovalerylglutamic acid Quattro_QQQ 25V, N/A-QTOF (Annotated) | splash10-053r-9200000000-cc34006618257f6ea5b7 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Isovalerylglutamic acid Quattro_QQQ 40V, N/A-QTOF (Annotated) | splash10-0a59-9000000000-3e27a676a2a4411c2829 | 2012-07-24 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 10V, Positive-QTOF | splash10-03e9-2690000000-c94698b4419e50280bab | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 20V, Positive-QTOF | splash10-0zgr-5910000000-83e9ceaf3666b8af59e4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 40V, Positive-QTOF | splash10-0a4i-9300000000-487a10e7bb58ff39e503 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 10V, Negative-QTOF | splash10-001i-0390000000-8860fc75938c87bad1e0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 20V, Negative-QTOF | splash10-0gx9-2930000000-49505f61212051cf6fb5 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 40V, Negative-QTOF | splash10-0zi3-9700000000-b36d32bd2df0b4eff525 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 10V, Positive-QTOF | splash10-000t-0940000000-f72f7d92a512f7367827 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 20V, Positive-QTOF | splash10-0f89-3900000000-3853c91ba592f8db62da | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 40V, Positive-QTOF | splash10-052u-9200000000-6d93f6efacf39fadd847 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 10V, Negative-QTOF | splash10-003r-0790000000-d24080c90f131f16a12d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 20V, Negative-QTOF | splash10-0ufs-0900000000-74ffc458766b51f8c074 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 40V, Negative-QTOF | splash10-0udl-5900000000-c0aa356dc6adf7a53796 | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
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