Record Information |
---|
Version | 1.0 |
---|
Creation date | 2015-05-07 19:24:28 UTC |
---|
Update date | 2019-11-26 03:21:47 UTC |
---|
Primary ID | FDB030510 |
---|
Secondary Accession Numbers | |
---|
Chemical Information |
---|
FooDB Name | 4-methyl-2-oxopentanoate |
---|
Description | Ketoleucine, also known as alpha-ketoisocaproic acid or 2-oxoisocaproate, belongs to short-chain keto acids and derivatives class of compounds. Those are keto acids with an alkyl chain the contains less than 6 carbon atoms. Ketoleucine is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Ketoleucine can be found in a number of food items such as arctic blackberry, sesame, sea-buckthornberry, and soft-necked garlic, which makes ketoleucine a potential biomarker for the consumption of these food products. Ketoleucine can be found primarily in most biofluids, including saliva, blood, cerebrospinal fluid (CSF), and urine, as well as in human muscle, neuron and prostate tissues. Ketoleucine exists in all living species, ranging from bacteria to humans. In humans, ketoleucine is involved in the valine, leucine and isoleucine degradation. Ketoleucine is also involved in several metabolic disorders, some of which include methylmalonate semialdehyde dehydrogenase deficiency, propionic acidemia, 3-methylglutaconic aciduria type IV, and 3-methylglutaconic aciduria type I. Ketoleucine is a non-carcinogenic (not listed by IARC) potentially toxic compound. Ketoleucine is a metabolite that accumulates in Maple Syrup Urine Disease (MSUD) and shown to compromise brain energy metabolism by blocking the respiratory chain (T3DB). |
---|
CAS Number | 816-66-0 |
---|
Structure | |
---|
Synonyms | |
---|
Predicted Properties | |
---|
Chemical Formula | C6H10O3 |
---|
IUPAC name | 4-methyl-2-oxopentanoic acid |
---|
InChI Identifier | InChI=1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9) |
---|
InChI Key | BKAJNAXTPSGJCU-UHFFFAOYSA-N |
---|
Isomeric SMILES | CC(C)CC(=O)C(O)=O |
---|
Average Molecular Weight | 130.1418 |
---|
Monoisotopic Molecular Weight | 130.062994186 |
---|
Classification |
---|
Description | Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic acids and derivatives |
---|
Class | Keto acids and derivatives |
---|
Sub Class | Short-chain keto acids and derivatives |
---|
Direct Parent | Short-chain keto acids and derivatives |
---|
Alternative Parents | |
---|
Substituents | - Branched fatty acid
- Methyl-branched fatty acid
- Short-chain keto acid
- Alpha-keto acid
- Fatty acyl
- Alpha-hydroxy ketone
- Ketone
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Carbonyl group
- Hydrocarbon derivative
- Organic oxygen compound
- Organooxygen compound
- Organic oxide
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Physiological effect | Health effect: |
---|
Disposition | Route of exposure: Source: Biological location: |
---|
Process | Naturally occurring process: |
---|
Role | Indirect biological role: Biological role: Industrial application: |
---|
Physico-Chemical Properties |
---|
Physico-Chemical Properties - Experimental | |
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
GC-MS | 4-Methyl-2-oxopentanoic acid, 3 TMS, GC-MS Spectrum | splash10-000i-9400000000-49d055f04bfe1877ac5b | Spectrum | GC-MS | 4-Methyl-2-oxopentanoic acid, 3 TMS, GC-MS Spectrum | splash10-029j-8930000000-c6c54bf6ee2995a2195b | Spectrum | GC-MS | 4-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrum | splash10-0002-1910000000-0ba38257e25873312809 | Spectrum | GC-MS | 4-Methyl-2-oxopentanoic acid, 2 TMS, GC-MS Spectrum | splash10-0a5c-4930000000-61247369a805fa2a77a7 | Spectrum | GC-MS | 4-Methyl-2-oxopentanoic acid, 1 MEOX; 1 TMS, GC-MS Spectrum | splash10-000i-9510000000-8bfc5a54e29f65edf361 | Spectrum | GC-MS | 4-Methyl-2-oxopentanoic acid, 1 MEOX; 1 TMS, GC-MS Spectrum | splash10-00lj-9620000000-aa8409ceb2359d903f38 | Spectrum | GC-MS | 4-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrum | splash10-000i-9400000000-49d055f04bfe1877ac5b | Spectrum | GC-MS | 4-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrum | splash10-029j-8930000000-c6c54bf6ee2995a2195b | Spectrum | GC-MS | 4-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrum | splash10-0002-1910000000-0ba38257e25873312809 | Spectrum | GC-MS | 4-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrum | splash10-0a5c-4930000000-61247369a805fa2a77a7 | Spectrum | GC-MS | 4-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrum | splash10-000i-9510000000-8bfc5a54e29f65edf361 | Spectrum | GC-MS | 4-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrum | splash10-00lj-9620000000-aa8409ceb2359d903f38 | Spectrum | GC-MS | 4-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrum | splash10-00ks-7930000000-4e9cfd715fa884d30e7f | Spectrum | GC-MS | 4-Methyl-2-oxopentanoic acid, non-derivatized, GC-MS Spectrum | splash10-000i-9500000000-709ebcb57f006703c269 | Spectrum | Predicted GC-MS | 4-Methyl-2-oxopentanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9000000000-e410bce23706f826f8dd | Spectrum | Predicted GC-MS | 4-Methyl-2-oxopentanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9400000000-c4f06cea1e27a2b24660 | Spectrum | Predicted GC-MS | 4-Methyl-2-oxopentanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 4-Methyl-2-oxopentanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 4-Methyl-2-oxopentanoic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 4-Methyl-2-oxopentanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 4-Methyl-2-oxopentanoic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0006-9000000000-bed7ac074a60210971e3 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-014i-9200000000-2fa08d2b4df406cf63ea | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-014j-9000000000-045be8e8dca3f93d45ba | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-004i-0900000000-237fa8ad6bfb929be31e | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-004r-9700000000-8d38d24fce78b1ff13e6 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0a59-9000000000-759cfc0817917283d1a5 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0a4l-9000000000-2a068ada71fbe0a5a988 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0a4l-9000000000-58e61e31f3c96d84d799 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-0900000000-237fa8ad6bfb929be31e | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004r-9700000000-8d38d24fce78b1ff13e6 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a59-9000000000-759cfc0817917283d1a5 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4l-9000000000-2a068ada71fbe0a5a988 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4l-9000000000-58e61e31f3c96d84d799 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-004i-0900000000-556a0d1cf568609752d1 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-004r-5900000000-20f6923c8ed45e9fa088 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-004i-0900000000-b66d521478c92e2d77d0 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-9c3a698d9f28af574ef6 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-03di-9000000000-47ced70de4860e900283 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-03xr-7900000000-0461a5a56e36a03fe522 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-08gr-7900000000-31021fda89eb6535185f | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0btm-9200000000-3bf5df4b557ef87267f4 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-37839bf70647d24b94a4 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-4900000000-796467909d1d4c087a07 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01ri-9400000000-0abcd021721f32c10e42 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-015l-9000000000-5c33a47dfeb09a182983 | 2015-05-27 | View Spectrum |
|
---|
NMR | Type | Description | | View |
---|
1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
|
---|
External Links |
---|
ChemSpider ID | Not Available |
---|
ChEMBL ID | Not Available |
---|
KEGG Compound ID | Not Available |
---|
Pubchem Compound ID | Not Available |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | Not Available |
---|
HMDB ID | Not Available |
---|
CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | Not Available |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | Not Available |
---|
HET ID | Not Available |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | Not Available |
---|
GoodScent ID | Not Available |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Not Available |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | Not Available |
---|
Enzymes | Not Available |
---|
Pathways | Not Available |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Not Available |
---|
Files |
---|
MSDS | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
Content Reference | |
---|