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Showing metabocard for (R)-3-Hydroxyisobutyric acid (HMDB0000336)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:55:55 UTC
HMDB IDHMDB0000336
Secondary Accession Numbers
  • HMDB00336
Metabolite Identification
Common Name(R)-3-Hydroxyisobutyric acid
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 ).
Structure
Data?1582752124
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000336 ((R)-3-Hydroxyisobutyric acid)


  Mrv1652307101917012D          

  7  6  0  0  1  0            999 V2000
   18.9558   -4.1704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0981   -4.1704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8124   -2.9330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5268   -4.1704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2413   -3.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5268   -4.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8124   -3.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  7  1  0  0  0  0
  3  7  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  1  0  0  0
  4  7  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000336 ((R)-3-Hydroxyisobutyric acid)

HMDB0000336
     RDKit          3D
(R)-3-Hydroxyisobutyric acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    0.3802    1.5829    0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2283    0.1864   -0.4860 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2372   -0.2358   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5671   -0.1965    0.9586 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0044   -0.7387    0.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6514   -0.3339    1.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0443   -2.1164    0.0836 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4103    1.9279   -0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171    1.5638    1.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3086    2.3115   -0.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5463    0.1549   -1.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8364    0.5362   -0.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3684   -1.2241   -0.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9172   -1.0332    1.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7525   -2.3850   -0.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  6
  3 12  1  0
  3 13  1  0
  4 14  1  0
  7 15  1  0
M  END
Download

3D SDF for HMDB0000336 ((R)-3-Hydroxyisobutyric acid)


  Mrv1652307101917012D          

  7  6  0  0  1  0            999 V2000
   18.9558   -4.1704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0981   -4.1704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8124   -2.9330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5268   -4.1704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2413   -3.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5268   -4.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8124   -3.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  7  1  0  0  0  0
  3  7  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  1  0  0  0
  4  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000336

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C4H8O3

> <MOLECULAR_WEIGHT>
104.1045

> <EXACT_MASS>
104.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
9.982094489313155

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-3-hydroxy-2-methylpropanoic acid

> <ALOGPS_LOGP>
-0.47

> <JCHEM_LOGP>
-0.26059474566666674

> <ALOGPS_LOGS>
0.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.518589741896943

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.365338407814565

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6927927583619056

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
23.6198

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.71e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(R)-3-hydroxyisobutyric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000336 ((R)-3-Hydroxyisobutyric acid)

HMDB0000336
     RDKit          3D
(R)-3-Hydroxyisobutyric acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    0.3802    1.5829    0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2283    0.1864   -0.4860 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2372   -0.2358   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5671   -0.1965    0.9586 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0044   -0.7387    0.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6514   -0.3339    1.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0443   -2.1164    0.0836 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4103    1.9279   -0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171    1.5638    1.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3086    2.3115   -0.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5463    0.1549   -1.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8364    0.5362   -0.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3684   -1.2241   -0.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9172   -1.0332    1.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7525   -2.3850   -0.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  6
  3 12  1  0
  3 13  1  0
  4 14  1  0
  7 15  1  0
M  END
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PDB for HMDB0000336 ((R)-3-Hydroxyisobutyric acid)

HEADER    PROTEIN                                 10-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-JUL-19         0                                  
HETATM    1  O   UNK     0      35.384  -7.785   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      30.050  -7.785   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      31.383  -5.475   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      32.717  -7.785   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      34.050  -7.015   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.717  -9.325   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.383  -7.015   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    7                                                            
CONECT    3    7                                                            
CONECT    4    5    6    7                                                  
CONECT    5    1    4                                                       
CONECT    6    4                                                            
CONECT    7    2    3    4                                                  
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0000336 ((R)-3-Hydroxyisobutyric acid)

COMPND    HMDB0000336
HETATM    1  C1  UNL     1       0.380   1.583   0.071  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.228   0.186  -0.486  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.237  -0.236  -0.386  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.567  -0.196   0.959  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.004  -0.739   0.368  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.651  -0.334   1.371  1.00  0.00           O  
HETATM    7  O3  UNL     1       1.044  -2.116   0.084  1.00  0.00           O  
HETATM    8  H1  UNL     1       1.410   1.928  -0.133  1.00  0.00           H  
HETATM    9  H2  UNL     1       0.217   1.564   1.155  1.00  0.00           H  
HETATM   10  H3  UNL     1      -0.309   2.311  -0.404  1.00  0.00           H  
HETATM   11  H4  UNL     1       0.546   0.155  -1.539  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.836   0.536  -0.923  1.00  0.00           H  
HETATM   13  H6  UNL     1      -1.368  -1.224  -0.849  1.00  0.00           H  
HETATM   14  H7  UNL     1      -1.917  -1.033   1.315  1.00  0.00           H  
HETATM   15  H8  UNL     1       1.752  -2.385  -0.603  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    5   11
CONECT    3    4   12   13
CONECT    4   14
CONECT    5    6    6    7
CONECT    7   15
END
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SMILES for HMDB0000336 ((R)-3-Hydroxyisobutyric acid)

C[C@H](CO)C(O)=O
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INCHI for HMDB0000336 ((R)-3-Hydroxyisobutyric acid)

InChI=1S/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(R)-3-HydroxyisobutyrateGenerator
(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
3R-Hydroxy-isobutyrateHMDB
(2R)-3-Hydroxy-2-methylpropanoic acidHMDB
(2R)-3-Hydroxy-2-methylpropionic acidHMDB
(R)-3-Hydroxy-2-methyl-propanoic acidHMDB
(R)-3-Hydroxy-2-methyl-propionic acidHMDB
(R)-3-Hydroxy-2-methylpropanoic acidHMDB
(±)-3-hydroxy-2-methylpropanoic acidHMDB
(±)-3-hydroxy-2-methylpropionic acidHMDB
2-(Hydroxymethyl)propanoic acidHMDB
2-(Hydroxymethyl)propionic acidHMDB
2-Methyl-3-hydroxypropanoic acidHMDB
2-Methyl-3-hydroxypropionic acidHMDB
3-HIBAHMDB
3-Hydroxy-2-methylpropanoic acidHMDB
3-Hydroxy-2-methylpropionic acidHMDB
3-Hydroxyisobutyric acidHMDB
D-beta-Hydroxyisobutyric acidHMDB
D-Β-hydroxyisobutyric acidHMDB
DL-3-Hydroxyisobutyric acidHMDB
R-3-Hydroxyisobutyric acidHMDB
R-Β-hydroxyisobutyric acidHMDB
beta-Hydroxyisobutyric acidHMDB
Β-hydroxyisobutyric acidHMDB
3-Hydroxy-2-isobutyrateHMDB
3-Hydroxy-2-isobutyric acidHMDB
(R)-3-Hydroxyisobutyric acidHMDB
Chemical FormulaC4H8O3
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
IUPAC Name(2R)-3-hydroxy-2-methylpropanoic acid
Traditional Name(R)-3-hydroxyisobutyric acid
CAS Registry Number1910-47-0
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 KeyDBXBTMSZEOQQDU-GSVOUGTGSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility571 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.62 m³·mol⁻¹ChemAxon
Polarizability9.98 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+120.22331661259
DarkChem[M-H]-115.02931661259
AllCCS[M+H]+126.80532859911
AllCCS[M-H]-124.49432859911
DeepCCS[M+H]+118.48530932474
DeepCCS[M-H]-115.68630932474
DeepCCS[M-2H]-152.14930932474
DeepCCS[M+Na]+126.8730932474
AllCCS[M+H]+126.832859911
AllCCS[M+H-H2O]+122.532859911
AllCCS[M+NH4]+130.832859911
AllCCS[M+Na]+132.032859911
AllCCS[M-H]-124.532859911
AllCCS[M+Na-2H]-128.432859911
AllCCS[M+HCOO]-132.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-3-Hydroxyisobutyric acidC[C@H](CO)C(O)=O2050.5Standard polar33892256
(R)-3-Hydroxyisobutyric acidC[C@H](CO)C(O)=O932.7Standard non polar33892256
(R)-3-Hydroxyisobutyric acidC[C@H](CO)C(O)=O1017.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-3-Hydroxyisobutyric acid,1TMS,isomer #1C[C@H](CO[Si](C)(C)C)C(=O)O1085.9Semi standard non polar33892256
(R)-3-Hydroxyisobutyric acid,1TMS,isomer #2C[C@H](CO)C(=O)O[Si](C)(C)C1020.5Semi standard non polar33892256
(R)-3-Hydroxyisobutyric acid,2TMS,isomer #1C[C@H](CO[Si](C)(C)C)C(=O)O[Si](C)(C)C1170.4Semi standard non polar33892256
(R)-3-Hydroxyisobutyric acid,1TBDMS,isomer #1C[C@H](CO[Si](C)(C)C(C)(C)C)C(=O)O1328.6Semi standard non polar33892256
(R)-3-Hydroxyisobutyric acid,1TBDMS,isomer #2C[C@H](CO)C(=O)O[Si](C)(C)C(C)(C)C1255.6Semi standard non polar33892256
(R)-3-Hydroxyisobutyric acid,2TBDMS,isomer #1C[C@H](CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1592.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxyisobutyric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-00f48b549b40517fc7562017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxyisobutyric acid GC-MS (2 TMS) - 70eV, Positivesplash10-00gr-9720000000-2a61310303ff8f2a7b422017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxyisobutyric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxyisobutyric acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxyisobutyric acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxyisobutyric acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxyisobutyric acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxyisobutyric acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 10V, Positive-QTOFsplash10-052r-9500000000-543c65dad21c233fc8a82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 20V, Positive-QTOFsplash10-052o-9000000000-7b7dcb34e28cb55ddafb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 40V, Positive-QTOFsplash10-0006-9000000000-27deee4c6a386a43ebc32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 10V, Negative-QTOFsplash10-0udi-3900000000-a7aa709e1985355b4bd92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 20V, Negative-QTOFsplash10-0pi0-9200000000-01a40fbe4d19283ef0802016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 40V, Negative-QTOFsplash10-0a4l-9000000000-622de763b5ea31ff4ee62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 10V, Negative-QTOFsplash10-0uki-9700000000-04713faa703ce789efb32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 20V, Negative-QTOFsplash10-0a4r-9100000000-b0202d15bd6411bc7d802021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 40V, Negative-QTOFsplash10-052f-9000000000-d2c32880fd340aac0bad2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 10V, Positive-QTOFsplash10-0ap3-9000000000-6c76b805d02ad21ab06a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 20V, Positive-QTOFsplash10-0aou-9000000000-fc5e7dbe1e224cc87d4f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxyisobutyric acid 40V, Positive-QTOFsplash10-0006-9000000000-021ab3207a43699617f42021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified21.0 +/- 2.0 uMAdult (>18 years old)Both
Normal		 details
Cerebrospinal Fluid (CSF)Detected and Quantified6 +/- 3 uMAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified<95 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified12.33 (5.09-23.56) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified38.0 +/- 5.0 uMAdult (>18 years old)Both
Diabetes 		details
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 2
  1. 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
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021960
KNApSAcK IDNot Available
Chemspider ID9392288
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11217234
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000146
Good Scents IDNot Available
References
Synthesis ReferenceSprecher, 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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]