Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2023-05-30 20:55:55 UTC |
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HMDB ID | HMDB0000336 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (R)-3-Hydroxyisobutyric acid |
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Description | (R)-3-Hydroxyisobutyric acid (3-HIBA) is an organic acid. The chiral metabolites 3-hydroxyisobutyric acid (HIBA) and 3-aminoisobutyric acid (AIBA) are intermediates in the pathways of L-valine and thymine and play an important role in the diagnosis of the very rare inherited metabolic diseases 3-hydroxyisobutyric aciduria (OMIM: 236795 ) and methylmalonic semialdehyde dehydrogenase deficiency (OMIM: 603178 ) (PMID: 10686279 ). (R)-3-Hydroxyisobutyric acid has been identified in the human placenta (PMID: 32033212 ). |
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Structure | InChI=1S/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1 |
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Synonyms | Value | Source |
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(R)-3-Hydroxyisobutyrate | Generator | (R)-3-Hydroxy-2-methylpropionate | HMDB | (R)-3-Hydroxy-2-methylpropionic acid | HMDB | 2-Methyl-(R)-hydracrylate | HMDB | 2-Methyl-(R)-hydracrylic acid | HMDB | 3-Hydroxy-2-methylpropionate | HMDB | D-(-)-3-Hydroxyisobutyrate | HMDB | D-(-)-3-Hydroxyisobutyric acid | HMDB | D-b-Hydroxyisobutyrate | HMDB | D-b-Hydroxyisobutyric acid | HMDB | delta-(-)-3-Hydroxyisobutyrate | HMDB | delta-(-)-3-Hydroxyisobutyric acid | HMDB | delta-beta-Hydroxyisobutyrate | HMDB | delta-beta-Hydroxyisobutyric acid | HMDB | R-b-Hydroxyisobutyrate | HMDB | R-b-Hydroxyisobutyric acid | HMDB | R-beta-Hydroxyisobutyrate | HMDB | R-beta-Hydroxyisobutyric acid | HMDB | 3R-Hydroxy-isobutyrate | HMDB | (2R)-3-Hydroxy-2-methylpropanoic acid | HMDB | (2R)-3-Hydroxy-2-methylpropionic acid | HMDB | (R)-3-Hydroxy-2-methyl-propanoic acid | HMDB | (R)-3-Hydroxy-2-methyl-propionic acid | HMDB | (R)-3-Hydroxy-2-methylpropanoic acid | HMDB | (±)-3-hydroxy-2-methylpropanoic acid | HMDB | (±)-3-hydroxy-2-methylpropionic acid | HMDB | 2-(Hydroxymethyl)propanoic acid | HMDB | 2-(Hydroxymethyl)propionic acid | HMDB | 2-Methyl-3-hydroxypropanoic acid | HMDB | 2-Methyl-3-hydroxypropionic acid | HMDB | 3-HIBA | HMDB | 3-Hydroxy-2-methylpropanoic acid | HMDB | 3-Hydroxy-2-methylpropionic acid | HMDB | 3-Hydroxyisobutyric acid | HMDB | D-beta-Hydroxyisobutyric acid | HMDB | D-Β-hydroxyisobutyric acid | HMDB | DL-3-Hydroxyisobutyric acid | HMDB | R-3-Hydroxyisobutyric acid | HMDB | R-Β-hydroxyisobutyric acid | HMDB | beta-Hydroxyisobutyric acid | HMDB | Β-hydroxyisobutyric acid | HMDB | 3-Hydroxy-2-isobutyrate | HMDB | 3-Hydroxy-2-isobutyric acid | HMDB | (R)-3-Hydroxyisobutyric acid | HMDB |
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Chemical Formula | C4H8O3 |
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Average Molecular Weight | 104.1045 |
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Monoisotopic Molecular Weight | 104.047344122 |
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IUPAC Name | (2R)-3-hydroxy-2-methylpropanoic acid |
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Traditional Name | (R)-3-hydroxyisobutyric acid |
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CAS Registry Number | 1910-47-0 |
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SMILES | C[C@H](CO)C(O)=O |
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InChI Identifier | InChI=1S/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1 |
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InChI Key | DBXBTMSZEOQQDU-GSVOUGTGSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Hydroxy acids and derivatives |
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Sub Class | Beta hydroxy acids and derivatives |
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Direct Parent | Beta hydroxy acids and derivatives |
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Alternative Parents | |
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Substituents | - Beta-hydroxy acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | |
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Disposition | |
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Process | Not Available |
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Role | |
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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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(R)-3-Hydroxyisobutyric acid,1TMS,isomer #1 | C[C@H](CO[Si](C)(C)C)C(=O)O | 1085.9 | Semi standard non polar | 33892256 | (R)-3-Hydroxyisobutyric acid,1TMS,isomer #2 | C[C@H](CO)C(=O)O[Si](C)(C)C | 1020.5 | Semi standard non polar | 33892256 | (R)-3-Hydroxyisobutyric acid,2TMS,isomer #1 | C[C@H](CO[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1170.4 | Semi standard non polar | 33892256 | (R)-3-Hydroxyisobutyric acid,1TBDMS,isomer #1 | C[C@H](CO[Si](C)(C)C(C)(C)C)C(=O)O | 1328.6 | Semi standard non polar | 33892256 | (R)-3-Hydroxyisobutyric acid,1TBDMS,isomer #2 | C[C@H](CO)C(=O)O[Si](C)(C)C(C)(C)C | 1255.6 | Semi standard non polar | 33892256 | (R)-3-Hydroxyisobutyric acid,2TBDMS,isomer #1 | C[C@H](CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1592.3 | Semi standard non polar | 33892256 |
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Spectra |
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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 - (R)-3-Hydroxyisobutyric acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-9000000000-00f48b549b40517fc756 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (R)-3-Hydroxyisobutyric acid GC-MS (2 TMS) - 70eV, Positive | splash10-00gr-9720000000-2a61310303ff8f2a7b42 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (R)-3-Hydroxyisobutyric acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (R)-3-Hydroxyisobutyric acid GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (R)-3-Hydroxyisobutyric acid GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (R)-3-Hydroxyisobutyric acid GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (R)-3-Hydroxyisobutyric acid GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (R)-3-Hydroxyisobutyric acid GC-MS (TBDMS_2_1) - 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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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 10V, Positive-QTOF | splash10-052r-9500000000-543c65dad21c233fc8a8 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 20V, Positive-QTOF | splash10-052o-9000000000-7b7dcb34e28cb55ddafb | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 40V, Positive-QTOF | splash10-0006-9000000000-27deee4c6a386a43ebc3 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 10V, Negative-QTOF | splash10-0udi-3900000000-a7aa709e1985355b4bd9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 20V, Negative-QTOF | splash10-0pi0-9200000000-01a40fbe4d19283ef080 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 40V, Negative-QTOF | splash10-0a4l-9000000000-622de763b5ea31ff4ee6 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 10V, Negative-QTOF | splash10-0uki-9700000000-04713faa703ce789efb3 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 20V, Negative-QTOF | splash10-0a4r-9100000000-b0202d15bd6411bc7d80 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 40V, Negative-QTOF | splash10-052f-9000000000-d2c32880fd340aac0bad | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 10V, Positive-QTOF | splash10-0ap3-9000000000-6c76b805d02ad21ab06a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 20V, Positive-QTOF | splash10-0aou-9000000000-fc5e7dbe1e224cc87d4f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 40V, Positive-QTOF | splash10-0006-9000000000-021ab3207a43699617f4 | 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) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | 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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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Urine
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 21.0 +/- 2.0 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 6 +/- 3 uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | <95 umol/mmol creatinine | Children (1 - 18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 12.33 (5.09-23.56) umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 38.0 +/- 5.0 uM | Adult (>18 years old) | Both | Diabetes | | details |
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Associated Disorders and Diseases |
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Disease References | Diabetes mellitus type 2 |
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- Avogaro A, Bier DM: Contribution of 3-hydroxyisobutyrate to the measurement of 3-hydroxybutyrate in human plasma: comparison of enzymatic and gas-liquid chromatography-mass spectrometry assays in normal and in diabetic subjects. J Lipid Res. 1989 Nov;30(11):1811-7. [PubMed:2614280 ]
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Associated OMIM IDs | - 125853 (Diabetes mellitus type 2)
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB021960 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 9392288 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 11217234 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | MDB00000146 |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Sprecher, M.; Sprinson, David B. Preparation of (R)-b-hydroxyisobutyric acid from threo-3-methyl-L-aspartate. Journal of Biological Chemistry (1966), 241(4), 868-71. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Podebrad F, Heil M, Beck T, Mosandl A, Sewell AC, Bohles H: Stereodifferentiation of 3-hydroxyisobutyric- and 3-aminoisobutyric acid in human urine by enantioselective multidimensional capillary gas chromatography-mass spectrometry. Clin Chim Acta. 2000 Feb 25;292(1-2):93-105. [PubMed:10686279 ]
- Gray RG, Pollitt RJ, Webley J: Methylmalonic semialdehyde dehydrogenase deficiency: demonstration of defective valine and beta-alanine metabolism and reduced malonic semialdehyde dehydrogenase activity in cultured fibroblasts. Biochem Med Metab Biol. 1987 Aug;38(1):121-4. [PubMed:3117077 ]
- Roe CR, Struys E, Kok RM, Roe DS, Harris RA, Jakobs C: Methylmalonic semialdehyde dehydrogenase deficiency: psychomotor delay and methylmalonic aciduria without metabolic decompensation. Mol Genet Metab. 1998 Sep;65(1):35-43. [PubMed:9787093 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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