Showing metabocard for alpha-Hydroxyisobutyric acid (MMDBc0000814)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 22:03:38 UTC
Update Date2024-10-15 21:25:24 UTC
Metabolite IDMMDBc0000814
Metabolite Identification
Common Namealpha-Hydroxyisobutyric acid
Descriptionalpha-Hydroxyisobutyric acid is a metabolite of methyl tert-butyl ether (MTBE). MTBE may be obtained through environmental exposure. MTBE is rapidly eliminated from the body, mainly through expired air as the unchanged compound. MTBE is to some extent metabolized to t-butyl alcohol (TBA) and formaldehyde and oxidized to 2-methyl-1,2-propanediol and alpha-hydroxyisobutyric acid. alpha-Hydroxyisobutyric acid has been used as an aerial bactericide.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdaf5b12a10>


  Mrv1652305271900022D          

  7  6  0  0  0  0            999 V2000
   -1.7435    0.7444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580   -0.4930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5096   -1.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5518   -1.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7489   -0.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3119   -0.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0264   -0.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  4  1  0  0  0  0
  7  5  1  0  0  0  0
  5  1  2  0  0  0  0
  5  2  1  0  0  0  0
  7  3  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fdaf5b12a10>

HMDB0000729
     RDKit          3D
alpha-Hydroxyisobutyric acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -0.2535    1.4434    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1765   -0.0224    0.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9877   -0.7766   -0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7586   -0.1556    1.6328 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1951   -0.5442    0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6721   -1.0199    1.4050 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9445   -0.5077   -0.7955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2460    2.0958    0.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5393    1.7310   -0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2153    1.6634   -0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7601   -0.2726   -1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7450   -1.8514   -0.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0559   -0.5829   -0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -1.1098    1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8560   -0.0904   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  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
  3 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  7 15  1  0
M  END
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3D SDF for #<Metabolite:0x00007fdaf5b12a10>


  Mrv1652305271900022D          

  7  6  0  0  0  0            999 V2000
   -1.7435    0.7444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580   -0.4930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5096   -1.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5518   -1.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7489   -0.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3119   -0.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0264   -0.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  4  1  0  0  0  0
  7  5  1  0  0  0  0
  5  1  2  0  0  0  0
  5  2  1  0  0  0  0
  7  3  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000814

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)(O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O3/c1-4(2,7)3(5)6/h7H,1-2H3,(H,5,6)

> <INCHI_KEY>
BWLBGMIXKSTLSX-UHFFFAOYSA-N

> <FORMULA>
C4H8O3

> <MOLECULAR_WEIGHT>
104.1045

> <EXACT_MASS>
104.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
9.872501504091092

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-2-methylpropanoic acid

> <ALOGPS_LOGP>
-0.37

> <JCHEM_LOGP>
-0.039063632000000056

> <ALOGPS_LOGS>
0.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.40275140597527

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.948421773706818

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7355605250234243

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
23.5531

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.78e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetonate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fdaf5b12a10>

HMDB0000729
     RDKit          3D
alpha-Hydroxyisobutyric acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -0.2535    1.4434    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1765   -0.0224    0.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9877   -0.7766   -0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7586   -0.1556    1.6328 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1951   -0.5442    0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6721   -1.0199    1.4050 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9445   -0.5077   -0.7955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2460    2.0958    0.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5393    1.7310   -0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2153    1.6634   -0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7601   -0.2726   -1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7450   -1.8514   -0.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0559   -0.5829   -0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -1.1098    1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8560   -0.0904   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  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
  3 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  7 15  1  0
M  END
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PDB for #<Metabolite:0x00007fdaf5b12a10>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      -3.255   1.390   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -4.588  -0.920   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -0.951  -2.123   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.897  -2.105   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.265  -0.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.582  -0.148   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.916  -0.918   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    5                                                            
CONECT    3    7                                                            
CONECT    4    7                                                            
CONECT    5    7    1    2                                                  
CONECT    6    7                                                            
CONECT    7    6    4    5    3                                             
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for #<Metabolite:0x00007fdaf5b12a10>

COMPND    HMDB0000729
HETATM    1  C1  UNL     1      -0.254   1.443   0.001  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.176  -0.022   0.363  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.988  -0.777  -0.685  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.759  -0.156   1.633  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.195  -0.544   0.356  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.672  -1.020   1.405  1.00  0.00           O  
HETATM    7  O3  UNL     1       1.944  -0.508  -0.796  1.00  0.00           O  
HETATM    8  H1  UNL     1      -0.246   2.096   0.916  1.00  0.00           H  
HETATM    9  H2  UNL     1       0.539   1.731  -0.721  1.00  0.00           H  
HETATM   10  H3  UNL     1      -1.215   1.663  -0.513  1.00  0.00           H  
HETATM   11  H4  UNL     1      -0.760  -0.273  -1.656  1.00  0.00           H  
HETATM   12  H5  UNL     1      -0.745  -1.851  -0.709  1.00  0.00           H  
HETATM   13  H6  UNL     1      -2.056  -0.583  -0.437  1.00  0.00           H  
HETATM   14  H7  UNL     1      -1.009  -1.110   1.731  1.00  0.00           H  
HETATM   15  H8  UNL     1       2.856  -0.090  -0.889  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    4    5
CONECT    3   11   12   13
CONECT    4   14
CONECT    5    6    6    7
CONECT    7   15
END
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SMILES for #<Metabolite:0x00007fdaf5b12a10>

CC(C)(O)C(O)=O
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INCHI for #<Metabolite:0x00007fdaf5b12a10>

InChI=1S/C4H8O3/c1-4(2,7)3(5)6/h7H,1-2H3,(H,5,6)
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Synonyms
ValueSource
2-Hydroxy-2-methylpropionic acidChEBI
2-Hydroxy-2-methylpropionsaeureChEBI
2-Methyl-2-hydroxypropanoic acidChEBI
2-Methyl-2-hydroxypropionsaeureChEBI
2-Methyllactic acidChEBI
Acetonic acidChEBI
Acide 2-hydroxy-2-methylpropanoiqueChEBI
Acido 2-hidroxi-2-metilpropionicoChEBI
alpha-Hydroxy-alpha-methylpropanoic acidChEBI
alpha-Hydroxy-alpha-methylpropionic acidChEBI
alpha-Hydroxyisobutanoic acidChEBI
HIBAChEBI
Hydroxydimethylacetic acidChEBI
2-Hydroxy-2-methylpropionateGenerator
2-Methyl-2-hydroxypropanoateGenerator
2-MethyllactateGenerator
AcetonateGenerator
a-Hydroxy-a-methylpropanoateGenerator
a-Hydroxy-a-methylpropanoic acidGenerator
alpha-Hydroxy-alpha-methylpropanoateGenerator
Α-hydroxy-α-methylpropanoateGenerator
Α-hydroxy-α-methylpropanoic acidGenerator
a-Hydroxy-a-methylpropionateGenerator
a-Hydroxy-a-methylpropionic acidGenerator
alpha-Hydroxy-alpha-methylpropionateGenerator
Α-hydroxy-α-methylpropionateGenerator
Α-hydroxy-α-methylpropionic acidGenerator
a-HydroxyisobutanoateGenerator
a-Hydroxyisobutanoic acidGenerator
alpha-HydroxyisobutanoateGenerator
Α-hydroxyisobutanoateGenerator
Α-hydroxyisobutanoic acidGenerator
HydroxydimethylacetateGenerator
a-HydroxyisobutyrateGenerator
a-Hydroxyisobutyric acidGenerator
alpha-HydroxyisobutyrateGenerator
Α-hydroxyisobutyrateGenerator
Α-hydroxyisobutyric acidGenerator
a-Hydroxy-isobutyrateHMDB
a-Hydroxy-isobutyric acidHMDB
alpha-Hydroxy-isobutyrateHMDB
Α-hydroxy-isobutyrateHMDB
Α-hydroxy-isobutyric acidHMDB
(CH3)2cohcoohHMDB
2-Hydroxy-2-methylpropanoateHMDB
2-Hydroxy-2-methylpropanoic acidHMDB
2-HydroxyisobutyrateHMDB
2-Hydroxyisobutyric acidHMDB
a-HIBHMDB
alpha-HIBHMDB
HydroxyisobutyrateHMDB
L-2-MethyllactateHMDB
L-2-Methyllactic acidHMDB
2-Hydroxyisobutyric acid, lead saltHMDB
Lead 2-hydroxyisobutyric acidHMDB
alpha-Hydroxyisobutyric acidChEBI
Molecular FormulaC4H8O3
Average Mass104.1045
Monoisotopic Mass104.047344122
IUPAC Name2-hydroxy-2-methylpropanoic acid
Traditional Nameacetonate
CAS Registry NumberNot Available
SMILES
CC(C)(O)C(O)=O
InChI Identifier
InChI=1S/C4H8O3/c1-4(2,7)3(5)6/h7H,1-2H3,(H,5,6)
InChI KeyBWLBGMIXKSTLSX-UHFFFAOYSA-N