| Common Name |
(R)-3-Hydroxyisobutyric acid
| Description |
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 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(R)-3-Hydroxy-2-methylpropionateHMDB
(R)-3-Hydroxy-2-methylpropionic acidHMDB
2-Methyl-(R)-hydracrylateHMDB
2-Methyl-(R)-hydracrylic acidHMDB
3-Hydroxy-2-methylpropionateHMDB
D-(-)-3-HydroxyisobutyrateHMDB
D-(-)-3-Hydroxyisobutyric acidHMDB
D-b-HydroxyisobutyrateHMDB
D-b-Hydroxyisobutyric acidHMDB
delta-(-)-3-HydroxyisobutyrateHMDB
delta-(-)-3-Hydroxyisobutyric acidHMDB
delta-beta-HydroxyisobutyrateHMDB
delta-beta-Hydroxyisobutyric acidHMDB
R-b-HydroxyisobutyrateHMDB
R-b-Hydroxyisobutyric acidHMDB
R-beta-HydroxyisobutyrateHMDB
R-beta-Hydroxyisobutyric acidHMDB
| Chemical Formlia |
C4H8O3
| Average Molecliar Weight |
104.1045
| Monoisotopic Molecliar Weight |
104.047344122
| IUPAC Name |
(2R)-3-hydroxy-2-methylpropanoic acid
| Traditional Name |
(R)-3-hydroxyisobutyric acid
| CAS Registry Number |
1910-47-0
| SMILES |
C[C@H](CO)C(O)=O
| InChI Identifier |
InChI=1S/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1
| InChI Key |
DBXBTMSZEOQQDU-GSVOUGTGSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic acids and derivatives
| Sub Class |
Hydroxy acids and derivatives
| Direct Parent |
Beta hydroxy acids and derivatives
| Alternative Parents |
Monocarboxylic acids and derivatives
Carboxylic acids
Primary alcohols
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| 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
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
Hydroxy fatty acids (LMFA01050382 )
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Not Available
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility571.0 mg/mLALOGPS
logP-0.47ALOGPS
logP-0.26ChemAxon
logS0.74ALOGPS
pKa (Strongest Acidic)4.37ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.62 m3·mol-1ChemAxon
Polarizability9.98 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Not Available
| Biofluid Locations |
Blood
Cerebrospinal Fluid (CSF)
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified21.0 +/- 2.0 uMAdlit (>18 years old)Both
Normal
2614280
details
Cerebrospinal Fluid (CSF)Detected and Quantified6 +/- 3 uMAdlit (>18 years old)BothNormal
18502700
details
UrineDetected but not Quantified Adlit (>18 years old)Both
Normal
24023812
details
UrineDetected and Quantified<95 umol/mmol creatinineChildren (1 – 18 years old)Both
Normal
BC Children's Hos…
details
|
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified38.0 +/- 5.0 uMAdlit (>18 years old)Both
Diabetes
2614280
details
| Associated Disorders and Diseases |
| Disease References |
| Diabetes mellitus type 2 |
- 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 ]
| Associated OMIM IDs |
125853 (Diabetes mellitus type 2)
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB021960
| KNApSAcK ID |
Not Available
| Chemspider ID |
9392288
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00336
| Metagene Link |
HMDB00336
| METLIN ID |
Not Available
| PubChem Compound |
11217234
| PDB ID |
HIU
| ChEBI ID |
Not Available
Product: PF-06840003
References |
| 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. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| 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 ]
|
PMID: 7812607