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Showing metabocard for Methyl 3-hydroxyisovalerate (HMDB0303162)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-23 23:52:44 UTC
Update Date2021-09-23 23:52:44 UTC
HMDB IDHMDB0303162
Secondary Accession NumbersNone
Metabolite Identification
Common NameMethyl 3-hydroxyisovalerate
DescriptionMethyl 3-hydroxyisovalerate is a member of the class of compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group. Methyl 3-hydroxyisovalerate is soluble (in water) and an extremely weak acidic compound (based on its pKa). Methyl 3-hydroxyisovalerate can be found in bilberry and black walnut, which makes methyl 3-hydroxyisovalerate a potential biomarker for the consumption of these food products.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0303162 (Methyl 3-hydroxyisovalerate)


  Mrv0541 02241220042D          

  9  8  0  0  0  0            999 V2000
    1.4562   -0.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0651    0.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3632    0.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3632    0.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0651    0.6291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7915    0.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6316   -0.5488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7915    0.5442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3877   -0.6291    0.0000 O   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  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
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3D MOL for HMDB0303162 (Methyl 3-hydroxyisovalerate)

HMDB0303162
     RDKit          3D
Methyl 3-hydroxyisovalerate
 21 20  0  0  0  0  0  0  0  0999 V2000
    3.5914   -0.0520    0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4491   -0.2945   -0.5719 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2002    0.0035   -0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1743    0.4890    1.1088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0442   -0.2460   -0.8410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2180    0.1941    0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5252   -0.0094   -0.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2086   -0.5454    1.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963    1.5745    0.2485 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4096   -0.0194    1.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0857    0.9192   -0.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3508   -0.8337   -0.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1362   -1.2796   -1.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0077    0.4825   -1.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0399   -0.9503   -0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2144    0.8169   -0.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4308   -0.0160   -1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3541   -1.2488    1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2286    0.1909    2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1311   -1.1454    1.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7261    1.9700    0.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  5 14  1  0
  7 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
M  END
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3D SDF for HMDB0303162 (Methyl 3-hydroxyisovalerate)


  Mrv0541 02241220042D          

  9  8  0  0  0  0            999 V2000
    1.4562   -0.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0651    0.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3632    0.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3632    0.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0651    0.6291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7915    0.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6316   -0.5488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7915    0.5442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3877   -0.6291    0.0000 O   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  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303162

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O3/c1-6(2,8)4-5(7)9-3/h8H,4H2,1-3H3

> <INCHI_KEY>
JNURPEZKOSMRMZ-UHFFFAOYSA-N

> <FORMULA>
C6H12O3

> <MOLECULAR_WEIGHT>
132.1577

> <EXACT_MASS>
132.07864425

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
13.823760275379193

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 3-hydroxy-3-methylbutanoate

> <ALOGPS_LOGP>
0.48

> <JCHEM_LOGP>
0.039464725000000034

> <ALOGPS_LOGS>
-0.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.12964791089275

> <JCHEM_PKA_STRONGEST_BASIC>
-2.742092003775509

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
32.8714

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-hydroxy-3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0303162 (Methyl 3-hydroxyisovalerate)

HMDB0303162
     RDKit          3D
Methyl 3-hydroxyisovalerate
 21 20  0  0  0  0  0  0  0  0999 V2000
    3.5914   -0.0520    0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4491   -0.2945   -0.5719 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2002    0.0035   -0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1743    0.4890    1.1088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0442   -0.2460   -0.8410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2180    0.1941    0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5252   -0.0094   -0.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2086   -0.5454    1.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963    1.5745    0.2485 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4096   -0.0194    1.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0857    0.9192   -0.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3508   -0.8337   -0.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1362   -1.2796   -1.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0077    0.4825   -1.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0399   -0.9503   -0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2144    0.8169   -0.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4308   -0.0160   -1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3541   -1.2488    1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2286    0.1909    2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1311   -1.1454    1.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7261    1.9700    0.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  5 14  1  0
  7 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
M  END
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PDB for HMDB0303162 (Methyl 3-hydroxyisovalerate)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.718  -1.070   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.988   0.286   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.678   1.095   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.678   0.365   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.988   1.174   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.344   0.444   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.179  -1.024   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.344   1.016   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.724  -1.174   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7    8                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    2                                                            
CONECT    8    2                                                            
CONECT    9    4                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0303162 (Methyl 3-hydroxyisovalerate)

COMPND    HMDB0303162
HETATM    1  C1  UNL     1       3.591  -0.052   0.186  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.449  -0.294  -0.572  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.200   0.004  -0.051  1.00  0.00           C  
HETATM    4  O2  UNL     1       1.174   0.489   1.109  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.044  -0.246  -0.841  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.218   0.194   0.035  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.525  -0.009  -0.656  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.209  -0.545   1.344  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.996   1.574   0.248  1.00  0.00           O  
HETATM   10  H1  UNL     1       3.410  -0.019   1.277  1.00  0.00           H  
HETATM   11  H2  UNL     1       4.086   0.919  -0.075  1.00  0.00           H  
HETATM   12  H3  UNL     1       4.351  -0.834  -0.077  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.136  -1.280  -1.173  1.00  0.00           H  
HETATM   14  H5  UNL     1      -0.008   0.483  -1.688  1.00  0.00           H  
HETATM   15  H6  UNL     1      -3.040  -0.950  -0.305  1.00  0.00           H  
HETATM   16  H7  UNL     1      -3.214   0.817  -0.337  1.00  0.00           H  
HETATM   17  H8  UNL     1      -2.431  -0.016  -1.769  1.00  0.00           H  
HETATM   18  H9  UNL     1      -0.354  -1.249   1.433  1.00  0.00           H  
HETATM   19  H10 UNL     1      -1.229   0.191   2.174  1.00  0.00           H  
HETATM   20  H11 UNL     1      -2.131  -1.145   1.433  1.00  0.00           H  
HETATM   21  H12 UNL     1      -1.726   1.970   0.778  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   13   14
CONECT    6    7    8    9
CONECT    7   15   16   17
CONECT    8   18   19   20
CONECT    9   21
END
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SMILES for HMDB0303162 (Methyl 3-hydroxyisovalerate)

COC(=O)CC(C)(C)O
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INCHI for HMDB0303162 (Methyl 3-hydroxyisovalerate)

InChI=1S/C6H12O3/c1-6(2,8)4-5(7)9-3/h8H,4H2,1-3H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Methyl 3-hydroxy-3-methylbutanoic acidGenerator
Methyl 3-hydroxyisovaleric acidGenerator
Chemical FormulaC6H12O3
Average Molecular Weight132.1577
Monoisotopic Molecular Weight132.07864425
IUPAC Namemethyl 3-hydroxy-3-methylbutanoate
Traditional Namemethyl 3-hydroxy-3-methylbutanoate
CAS Registry NumberNot Available
SMILES
COC(=O)CC(C)(C)O
InChI Identifier
InChI=1S/C6H12O3/c1-6(2,8)4-5(7)9-3/h8H,4H2,1-3H3
InChI KeyJNURPEZKOSMRMZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid methyl esters
Alternative Parents
Substituents
  • Fatty acid methyl ester
  • Methyl ester
  • Tertiary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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
logP0.48ALOGPS
logP0.039ChemAxon
logS-0.1ALOGPS
pKa (Strongest Acidic)15.13ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity32.87 m³·mol⁻¹ChemAxon
Polarizability13.82 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
AllCCS[M+H]+130.88632859911
AllCCS[M+H-H2O]+126.81232859911
AllCCS[M+Na]+135.77732859911
AllCCS[M+NH4]+134.68232859911
AllCCS[M-H]-129.50332859911
AllCCS[M+Na-2H]-132.40832859911
AllCCS[M+HCOO]-135.63932859911
DeepCCS[M+H]+133.830932474
DeepCCS[M-H]-130.81630932474
DeepCCS[M-2H]-167.54630932474
DeepCCS[M+Na]+142.88130932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxyisovalerate 10V, Positive-QTOFsplash10-0159-3900000000-909d7e2b09d4ae6296a82016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxyisovalerate 20V, Positive-QTOFsplash10-0159-7900000000-6968d99e73d135abb2d92016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxyisovalerate 40V, Positive-QTOFsplash10-00lg-9100000000-80f6f1e3d015aa2313b92016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxyisovalerate 10V, Negative-QTOFsplash10-001i-5900000000-7f7d83856d291bd1e98d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxyisovalerate 20V, Negative-QTOFsplash10-001j-9800000000-42644eef5c0224cd864a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxyisovalerate 40V, Negative-QTOFsplash10-001i-9100000000-21f526d75e69c3edcef12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxyisovalerate 10V, Positive-QTOFsplash10-00kf-9300000000-322dbbc3312a561806d72021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxyisovalerate 20V, Positive-QTOFsplash10-052f-9000000000-29352bba917358fbcefb2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxyisovalerate 40V, Positive-QTOFsplash10-0006-9000000000-4741669da972be98d6942021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxyisovalerate 10V, Negative-QTOFsplash10-0532-9400000000-82ede3e57bec8ea3d46d2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxyisovalerate 20V, Negative-QTOFsplash10-0a4l-9000000000-2bbc51590eddee0efb642021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 3-hydroxyisovalerate 40V, Negative-QTOFsplash10-052f-9000000000-6e7366e4d035d665b7062021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008102
KNApSAcK IDNot Available
Chemspider ID455331
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound521979
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available