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Showing metabocard for 2-Hydroxy-2-methylbutyric acid (HMDB0001987)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:30 UTC
Update Date2023-02-21 17:16:01 UTC
HMDB IDHMDB0001987
Secondary Accession Numbers
  • HMDB01987
Metabolite Identification
Common Name2-Hydroxy-2-methylbutyric acid
Description2-Hydroxy-2-methylbutyric acid, also known as (+/-)-2-hydroxy-2-methylbutanoate or 2-methyl-2-hydroxybutyric acid, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 2-Hydroxy-2-methylbutyric acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Data?1676999761
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001987 (2-Hydroxy-2-methylbutyric acid)


  Mrv1652305261923542D          

  8  7  0  0  0  0            999 V2000
   15.6916  -13.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4061  -13.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1206  -13.4413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4061  -12.2038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9772  -13.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2627  -13.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6916  -14.2663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6916  -12.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  1  0  0  0  0
M  END
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3D MOL for HMDB0001987 (2-Hydroxy-2-methylbutyric acid)

HMDB0001987
     RDKit          3D
2-Hydroxy-2-methylbutyric acid
 18 17  0  0  0  0  0  0  0  0999 V2000
   -1.9167   -0.3728    0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9229    0.0106   -0.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820    0.1473   -0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5733    1.2248    0.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2481    0.6350   -1.3187 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0730   -1.0873    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670   -1.7213    1.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2163   -1.5781   -0.3593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9041    0.0638   -0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7027    0.0552    1.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1036   -1.4747    0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9224   -0.7622   -1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2158    0.9660   -1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0495    2.0632    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6291    1.5601    0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2357    0.8312    1.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6734    1.2865   -1.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0398   -1.8473    0.1433 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
  3  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  4 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  8 18  1  0
M  END
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3D SDF for HMDB0001987 (2-Hydroxy-2-methylbutyric acid)


  Mrv1652305261923542D          

  8  7  0  0  0  0            999 V2000
   15.6916  -13.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4061  -13.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1206  -13.4413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4061  -12.2038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9772  -13.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2627  -13.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6916  -14.2663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6916  -12.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001987

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H10O3/c1-3-5(2,8)4(6)7/h8H,3H2,1-2H3,(H,6,7)

> <INCHI_KEY>
MBIQENSCDNJOIY-UHFFFAOYSA-N

> <FORMULA>
C5H10O3

> <MOLECULAR_WEIGHT>
118.1311

> <EXACT_MASS>
118.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
11.730470416866911

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-2-methylbutanoic acid

> <ALOGPS_LOGP>
0.13

> <JCHEM_LOGP>
0.483458763

> <ALOGPS_LOGS>
0.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.140030807663564

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.096793172378484

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8451698490140247

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
28.0771

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.49e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-2-methylbutyric acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001987 (2-Hydroxy-2-methylbutyric acid)

HMDB0001987
     RDKit          3D
2-Hydroxy-2-methylbutyric acid
 18 17  0  0  0  0  0  0  0  0999 V2000
   -1.9167   -0.3728    0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9229    0.0106   -0.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820    0.1473   -0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5733    1.2248    0.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2481    0.6350   -1.3187 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0730   -1.0873    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670   -1.7213    1.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2163   -1.5781   -0.3593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9041    0.0638   -0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7027    0.0552    1.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1036   -1.4747    0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9224   -0.7622   -1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2158    0.9660   -1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0495    2.0632    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6291    1.5601    0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2357    0.8312    1.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6734    1.2865   -1.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0398   -1.8473    0.1433 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
  3  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  4 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  8 18  1  0
M  END
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PDB for HMDB0001987 (2-Hydroxy-2-methylbutyric acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      29.291 -25.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      30.625 -24.320   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      31.958 -25.090   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      30.625 -22.780   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      27.957 -24.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.624 -25.090   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      29.291 -26.630   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      29.291 -23.550   0.000  0.00  0.00           C+0
CONECT    1    2    5    7    8                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    1    6                                                       
CONECT    6    5                                                            
CONECT    7    1                                                            
CONECT    8    1                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0001987 (2-Hydroxy-2-methylbutyric acid)

COMPND    HMDB0001987
HETATM    1  C1  UNL     1      -1.917  -0.373   0.273  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.923   0.011  -0.768  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.482   0.147  -0.263  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.573   1.225   0.829  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.248   0.635  -1.319  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.073  -1.087   0.228  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.567  -1.721   1.178  1.00  0.00           O  
HETATM    8  O3  UNL     1       2.216  -1.578  -0.359  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.904   0.064  -0.041  1.00  0.00           H  
HETATM   10  H2  UNL     1      -1.703   0.055   1.283  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.104  -1.475   0.324  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.922  -0.762  -1.552  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.216   0.966  -1.232  1.00  0.00           H  
HETATM   14  H6  UNL     1      -0.050   2.063   0.461  1.00  0.00           H  
HETATM   15  H7  UNL     1       1.629   1.560   0.833  1.00  0.00           H  
HETATM   16  H8  UNL     1       0.236   0.831   1.808  1.00  0.00           H  
HETATM   17  H9  UNL     1       0.673   1.286  -1.827  1.00  0.00           H  
HETATM   18  H10 UNL     1       3.040  -1.847   0.143  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3   12   13
CONECT    3    4    5    6
CONECT    4   14   15   16
CONECT    5   17
CONECT    6    7    7    8
CONECT    8   18
END
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SMILES for HMDB0001987 (2-Hydroxy-2-methylbutyric acid)

CCC(C)(O)C(O)=O
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INCHI for HMDB0001987 (2-Hydroxy-2-methylbutyric acid)

InChI=1S/C5H10O3/c1-3-5(2,8)4(6)7/h8H,3H2,1-2H3,(H,6,7)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-Hydroxy-2-methylbutyrateGenerator
(+/-)-2-hydroxy-2-methylbutanoateHMDB
(+/-)-2-hydroxy-2-methylbutanoic acidHMDB
(+/-)-2-hydroxy-2-methylbutyric acidHMDB
(+/-)-a-hydroxy-a-methylbutyric acidHMDB
(+/-)-alpha-hydroxy-alpha-methylbutyric acidHMDB
2-Hydroxy-2-methyl butyrateHMDB
2-Hydroxy-2-methyl butyric acidHMDB
2-Hydroxy-2-methyl-butanoateHMDB
2-Hydroxy-2-methyl-butanoic acidHMDB
2-Hydroxy-2-methyl-butyrateHMDB, Generator
2-Hydroxy-2-methyl-butyric acidHMDB
2-Hydroxy-2-methyl-N-butyrateHMDB
2-Hydroxy-2-methyl-N-butyric acidHMDB
2-Hydroxy-2-methylbutanoateHMDB
2-Hydroxy-2-methylbutanoic acidHMDB
2-Methyl-2-hydroxybutyric acidHMDB
a-Hydroxy-a-methyl-butyric acidHMDB
a-Hydroxy-a-methylbutyric acidHMDB
alpha-Hydroxy-alpha-methyl-butyric acidHMDB
alpha-Hydroxy-alpha-methylbutyric acidHMDB
2-Hydroxy-2-methylbutyric acidMeSH
Chemical FormulaC5H10O3
Average Molecular Weight118.1311
Monoisotopic Molecular Weight118.062994186
IUPAC Name2-hydroxy-2-methylbutanoic acid
Traditional Name2-hydroxy-2-methylbutyric acid
CAS Registry Number3739-30-8
SMILES
CCC(C)(O)C(O)=O
InChI Identifier
InChI=1S/C5H10O3/c1-3-5(2,8)4(6)7/h8H,3H2,1-2H3,(H,6,7)
InChI KeyMBIQENSCDNJOIY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Tertiary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point74 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility349 g/LALOGPS
logP0.13ALOGPS
logP0.48ChemAxon
logS0.47ALOGPS
pKa (Strongest Acidic)4.1ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.08 m³·mol⁻¹ChemAxon
Polarizability11.73 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]+125.29431661259
DarkChem[M-H]-120.75531661259
DeepCCS[M+H]+127.97730932474
DeepCCS[M-H]-125.17630932474
DeepCCS[M-2H]-161.61230932474
DeepCCS[M+Na]+136.32630932474
AllCCS[M+H]+129.032859911
AllCCS[M+H-H2O]+124.832859911
AllCCS[M+NH4]+132.932859911
AllCCS[M+Na]+134.132859911
AllCCS[M-H]-125.532859911
AllCCS[M+Na-2H]-128.832859911
AllCCS[M+HCOO]-132.532859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.83 minutes32390414
Predicted by Siyang on May 30, 20229.9499 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.88 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid107.0 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1129.8 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid342.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid90.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid195.9 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid56.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid361.2 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid420.5 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)113.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid675.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid217.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid881.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid241.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid247.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate484.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA291.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water168.0 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Hydroxy-2-methylbutyric acidCCC(C)(O)C(O)=O1877.7Standard polar33892256
2-Hydroxy-2-methylbutyric acidCCC(C)(O)C(O)=O942.6Standard non polar33892256
2-Hydroxy-2-methylbutyric acidCCC(C)(O)C(O)=O991.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Hydroxy-2-methylbutyric acid,1TMS,isomer #1CCC(C)(O[Si](C)(C)C)C(=O)O1117.4Semi standard non polar33892256
2-Hydroxy-2-methylbutyric acid,1TMS,isomer #2CCC(C)(O)C(=O)O[Si](C)(C)C1005.9Semi standard non polar33892256
2-Hydroxy-2-methylbutyric acid,2TMS,isomer #1CCC(C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1139.7Semi standard non polar33892256
2-Hydroxy-2-methylbutyric acid,1TBDMS,isomer #1CCC(C)(O[Si](C)(C)C(C)(C)C)C(=O)O1351.3Semi standard non polar33892256
2-Hydroxy-2-methylbutyric acid,1TBDMS,isomer #2CCC(C)(O)C(=O)O[Si](C)(C)C(C)(C)C1243.9Semi standard non polar33892256
2-Hydroxy-2-methylbutyric acid,2TBDMS,isomer #1CCC(C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1608.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-2-methylbutyric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fu-9100000000-c1a485cb07f0e01d496b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-2-methylbutyric acid GC-MS (2 TMS) - 70eV, Positivesplash10-010a-9720000000-17fc3516e0b12dfe88912017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-2-methylbutyric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-0kml-9100000000-e255071f7864eb24d52b2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-0a4m-9000000000-182db94e75153cc5fe7e2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-0a4l-9000000000-0b6fff2f0bd2398fd3da2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid 10V, Negative-QTOFsplash10-00xr-9400000000-2c345c81c4e7d0adda1f2021-09-17HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid 10V, Negative-QTOFsplash10-00xr-9400000000-2c345c81c4e7d0adda1f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid 40V, Negative-QTOFsplash10-0udl-3900000000-e3a36ea2735fe0adee102021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid 10V, Positive-QTOFsplash10-0ab9-9000000000-ca684c90aea7a89788602021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid 20V, Negative-QTOFsplash10-00di-9000000000-7aff4fb32a653cf107652021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid 40V, Positive-QTOFsplash10-052b-9000000000-d95699a47657772ec28b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid 20V, Positive-QTOFsplash10-0a4i-9000000000-dd58382320e8a790d7612021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid 10V, Positive-QTOFsplash10-0gi0-6900000000-8ff2da5d9ad778c414d82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid 20V, Positive-QTOFsplash10-0l9r-9400000000-1c799a2ce1690ef0b9b02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid 40V, Positive-QTOFsplash10-0a4i-9000000000-ab6ea008b1316fb4e28d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid 10V, Negative-QTOFsplash10-014i-6900000000-695acf62fd24b0a8056e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid 20V, Negative-QTOFsplash10-00di-9100000000-8798c599a99d917ff1d92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid 40V, Negative-QTOFsplash10-0ab9-9000000000-4262713c5b9c8e0e7c922017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid 10V, Positive-QTOFsplash10-0ab9-9200000000-339b88bdf89fa18818f02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid 20V, Positive-QTOFsplash10-0a4i-9000000000-23fdf7ac403bc732b18f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid 40V, Positive-QTOFsplash10-0a4i-9000000000-c91f3f5946e47e0898f12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid 10V, Negative-QTOFsplash10-014i-0900000000-0fb707df87ac8f8919b92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid 20V, Negative-QTOFsplash10-014i-3900000000-4ac52ee77b52ef304aa72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2-methylbutyric acid 40V, Negative-QTOFsplash10-0a4i-9000000000-0673811c3ca40c50612c2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
UrineDetected and Quantified2.8 +/- 1.5 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.8(0.4-1.5) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.998 +/- 0.926 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified14.4 +/- 3.9 umol/mmol creatinineAdult (>18 years old)Both
tert-Amyl-methyl ether exposed		 details
UrineDetected and Quantified2.384 +/- 3.843 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified3.961 +/- 6.507 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
tert-Amyl-methyl ether exposed
  1. Amberg A, Rosner E, Dekant W: Biotransformation and kinetics of excretion of tert-amyl-methyl ether in humans and rats after inhalation exposure. Toxicol Sci. 2000 Jun;55(2):274-83. [PubMed:10828258 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022784
KNApSAcK IDC00052118
Chemspider ID86129
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6416
PubChem Compound95433
PDB IDNot Available
ChEBI ID68454
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000361
Good Scents IDNot Available
References
Synthesis ReferenceYoung, Wm. G.; Dillon, Robert T.; Lucas, Howard J. Synthesis of the isomeric 2-butenes. Journal of the American Chemical Society (1929), 51 2528-34.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Holmes E, Foxall PJ, Spraul M, Farrant RD, Nicholson JK, Lindon JC: 750 MHz 1H NMR spectroscopy characterisation of the complex metabolic pattern of urine from patients with inborn errors of metabolism: 2-hydroxyglutaric aciduria and maple syrup urine disease. J Pharm Biomed Anal. 1997 Jul;15(11):1647-59. [PubMed:9260660 ]
  2. Amberg A, Rosner E, Dekant W: Biotransformation and kinetics of excretion of tert-amyl-methyl ether in humans and rats after inhalation exposure. Toxicol Sci. 2000 Jun;55(2):274-83. [PubMed:10828258 ]
  3. Fu X, Kimura M, Iga M, Yamaguchi S: Gas chromatographic-mass spectrometric screening for organic acidemias using dried urine filter paper: determination of alpha-ketoacids. J Chromatogr B Biomed Sci Appl. 2001 Jul 5;758(1):87-94. [PubMed:11482739 ]
  4. Dekant W, Bernauer U, Rosner E, Amberg A: Biotransformation of MTBE, ETBE, and TAME after inhalation or ingestion in rats and humans. Res Rep Health Eff Inst. 2001 May;(102):29-71; discussion 95-109. [PubMed:11504147 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
2-Hydroxy-2-methylbutyric acid → 6-(1-carboxy-1-methylpropoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2-Hydroxy-2-methylbutyric acid → 3,4,5-trihydroxy-6-[(2-hydroxy-2-methylbutanoyl)oxy]oxane-2-carboxylic aciddetails