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Showing metabocard for (R)-2,3-Dihydroxy-3-methylvalerate (HMDB0012140)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:19:53 UTC
Update Date2023-02-21 17:17:39 UTC
HMDB IDHMDB0012140
Secondary Accession Numbers
  • HMDB12140
Metabolite Identification
Common Name(R)-2,3-Dihydroxy-3-methylvalerate
Description(R)-2,3-Dihydroxy-methylvalerate is an intermediate in valine, leucine, and isoleucine biosynthesis. The pathway of valine biosynthesis is a four-step pathway that shares all of its steps with the parallel pathway of isoleucine biosynthesis. These entwined pathways are part of the superpathway of leucine, valine, and isoleucine biosynthesis, which generates not only isoleucine and valine but also leucine. (R)-2,3-Dihydroxy-methylvalerate is generated from 3-hydroxy-3-methyl-2-oxopentanoic acid via the enzyme ketol-acid reductoisomerase (EC 1.1.1.86). It is converted into (S)-3-methyl-2-oxopentanoic via the dihydroxy-acid dehydratase (EC 4.2.1.9).
Structure
Data?1676999859
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0012140 ((R)-2,3-Dihydroxy-3-methylvalerate)


  Mrv1652309042000342D          

 10  9  0  0  1  0            999 V2000
   15.4113  -13.3962    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1244  -13.8112    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.6949  -13.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8150  -12.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9967  -12.6836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8407  -13.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1206  -14.7118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9860  -13.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5462  -13.8112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8370  -12.5703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  1  5  1  1  0  0  0
  2  6  1  0  0  0  0
  2  7  1  6  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  2  0  0  0  0
M  END
Download

3D MOL for HMDB0012140 ((R)-2,3-Dihydroxy-3-methylvalerate)

HMDB0012140
     RDKit          3D
(R)-2,3-Dihydroxy-3-methylvalerate
 22 21  0  0  0  0  0  0  0  0999 V2000
   -2.2884    0.5495    0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8048    0.6478    0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0785   -0.3710   -0.2662 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6332   -1.7409    0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2911   -0.1214   -1.6108 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3986   -0.4143    0.0219 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9202   -1.4577   -0.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1101    0.8216   -0.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0012    0.8609   -1.2524 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7972    2.0157    0.2643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6067    1.3367   -0.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5824   -0.4279   -0.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8672    0.6931    1.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6281    0.3612    1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5117    1.6878    0.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1734   -2.5134    0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4430   -2.0697   -0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9113   -1.6879    1.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3959    0.8710   -1.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6062   -0.6796    1.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6721   -1.2133   -1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3633    2.8517    0.1824 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  6
  3  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  4 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  6 20  1  1
  7 21  1  0
 10 22  1  0
M  END
Download

3D SDF for HMDB0012140 ((R)-2,3-Dihydroxy-3-methylvalerate)


  Mrv1652309042000342D          

 10  9  0  0  1  0            999 V2000
   15.4113  -13.3962    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1244  -13.8112    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.6949  -13.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8150  -12.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9967  -12.6836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8407  -13.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1206  -14.7118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9860  -13.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5462  -13.8112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8370  -12.5703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  1  5  1  1  0  0  0
  2  6  1  0  0  0  0
  2  7  1  6  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012140

> <DATABASE_NAME>
hmdb

> <SMILES>
CC[C@@](C)(O)[C@@H](O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O4/c1-3-6(2,10)4(7)5(8)9/h4,7,10H,3H2,1-2H3,(H,8,9)/t4-,6+/m0/s1

> <INCHI_KEY>
PDGXJDXVGMHUIR-UJURSFKZSA-N

> <FORMULA>
C6H12O4

> <MOLECULAR_WEIGHT>
148.1571

> <EXACT_MASS>
148.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
14.433750785635485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-2,3-dihydroxy-3-methylpentanoic acid

> <ALOGPS_LOGP>
-0.44

> <JCHEM_LOGP>
-0.2990653966666666

> <ALOGPS_LOGS>
0.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.109092933547867

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.930562552523404

> <JCHEM_PKA_STRONGEST_BASIC>
-3.320314291594766

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
33.9645

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.86e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2,3-dihydroxy-3-methylpentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0012140 ((R)-2,3-Dihydroxy-3-methylvalerate)

HMDB0012140
     RDKit          3D
(R)-2,3-Dihydroxy-3-methylvalerate
 22 21  0  0  0  0  0  0  0  0999 V2000
   -2.2884    0.5495    0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8048    0.6478    0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0785   -0.3710   -0.2662 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6332   -1.7409    0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2911   -0.1214   -1.6108 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3986   -0.4143    0.0219 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9202   -1.4577   -0.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1101    0.8216   -0.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0012    0.8609   -1.2524 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7972    2.0157    0.2643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6067    1.3367   -0.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5824   -0.4279   -0.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8672    0.6931    1.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6281    0.3612    1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5117    1.6878    0.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1734   -2.5134    0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4430   -2.0697   -0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9113   -1.6879    1.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3959    0.8710   -1.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6062   -0.6796    1.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6721   -1.2133   -1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3633    2.8517    0.1824 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  6
  3  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  4 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  6 20  1  1
  7 21  1  0
 10 22  1  0
M  END
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PDB for HMDB0012140 ((R)-2,3-Dihydroxy-3-methylvalerate)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      28.768 -25.006   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      30.099 -25.781   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      27.430 -25.781   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.521 -23.676   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      27.994 -23.676   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      31.436 -25.006   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      30.092 -27.462   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      26.107 -25.020   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      32.753 -25.781   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      31.429 -23.465   0.000  0.00  0.00           O+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6    7                                                  
CONECT    3    1    8                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    2    9   10                                                  
CONECT    7    2                                                            
CONECT    8    3                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0012140 ((R)-2,3-Dihydroxy-3-methylvalerate)

COMPND    HMDB0012140
HETATM    1  C1  UNL     1      -2.288   0.550   0.289  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.805   0.648   0.579  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.078  -0.371  -0.266  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.633  -1.741   0.131  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.291  -0.121  -1.611  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.399  -0.414   0.022  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.920  -1.458  -0.772  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.110   0.822  -0.367  1.00  0.00           C  
HETATM    9  O3  UNL     1       3.001   0.861  -1.252  1.00  0.00           O  
HETATM   10  O4  UNL     1       1.797   2.016   0.264  1.00  0.00           O  
HETATM   11  H1  UNL     1      -2.607   1.337  -0.449  1.00  0.00           H  
HETATM   12  H2  UNL     1      -2.582  -0.428  -0.130  1.00  0.00           H  
HETATM   13  H3  UNL     1      -2.867   0.693   1.228  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.628   0.361   1.650  1.00  0.00           H  
HETATM   15  H5  UNL     1      -0.512   1.688   0.364  1.00  0.00           H  
HETATM   16  H6  UNL     1       0.173  -2.513   0.065  1.00  0.00           H  
HETATM   17  H7  UNL     1      -1.443  -2.070  -0.537  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.911  -1.688   1.196  1.00  0.00           H  
HETATM   19  H9  UNL     1      -0.396   0.871  -1.706  1.00  0.00           H  
HETATM   20  H10 UNL     1       1.606  -0.680   1.071  1.00  0.00           H  
HETATM   21  H11 UNL     1       1.672  -1.213  -1.703  1.00  0.00           H  
HETATM   22  H12 UNL     1       2.363   2.852   0.182  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14   15
CONECT    3    4    5    6
CONECT    4   16   17   18
CONECT    5   19
CONECT    6    7    8   20
CONECT    7   21
CONECT    8    9    9   10
CONECT   10   22
END
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SMILES for HMDB0012140 ((R)-2,3-Dihydroxy-3-methylvalerate)

CC[C@@](C)(O)[C@@H](O)C(O)=O
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INCHI for HMDB0012140 ((R)-2,3-Dihydroxy-3-methylvalerate)

InChI=1S/C6H12O4/c1-3-6(2,10)4(7)5(8)9/h4,7,10H,3H2,1-2H3,(H,8,9)/t4-,6+/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(2R,3R)-2,3-Dihydroxy-3-methylvaleric acidChEBI
(2R,3R)-2,3-Dihydroxy-3-methylpentanoateKegg
(2R,3R)-2,3-Dihydroxy-3-methylvalerateGenerator
(2R,3R)-2,3-Dihydroxy-3-methylpentanoic acidGenerator
(R)-2,3-Dihydroxy-3-methylvaleric acidGenerator
(R) 2,3-Dihydroxy-3-methylvaleric acidGenerator, HMDB
(R)-2,3-Dihydroxy-3-methylpentanoateHMDB
(R)-2,3-Dihydroxy-3-methylpentanoic acidHMDB
(R)-2,3-Dihydroxy-3-methylvalerateHMDB, KEGG
1-keto-2-MethylvalerateHMDB
2,3-Dihydroxy-3-methyl-valeric acidHMDB
2,3-Dihydroxy-3-methylpentanoateHMDB
2,3-Dihydroxy-3-methylpentanoic acidHMDB
2,3-Dihydroxy-valerianic acidHMDB
4,5-Dideoxy-3-C-methyl-pentonic acidHMDB
alpha,beta-Dihydroxy-beta-methylvaleric acidHMDB
CID8HMDB
DMVHMDB
Chemical FormulaC6H12O4
Average Molecular Weight148.1571
Monoisotopic Molecular Weight148.073558872
IUPAC Name(2R,3R)-2,3-dihydroxy-3-methylpentanoic acid
Traditional Name(2R,3R)-2,3-dihydroxy-3-methylpentanoic acid
CAS Registry Number562-43-6
SMILES
CC[C@@](C)(O)[C@@H](O)C(O)=O
InChI Identifier
InChI=1S/C6H12O4/c1-3-6(2,10)4(7)5(8)9/h4,7,10H,3H2,1-2H3,(H,8,9)/t4-,6+/m0/s1
InChI KeyPDGXJDXVGMHUIR-UJURSFKZSA-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
  • Methyl-branched fatty acid
  • Short-chain hydroxy acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Tertiary alcohol
  • 1,2-diol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial 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 Solubility486 g/LALOGPS
logP-0.44ALOGPS
logP-0.3ChemAxon
logS0.52ALOGPS
pKa (Strongest Acidic)3.93ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity33.96 m³·mol⁻¹ChemAxon
Polarizability14.43 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]+132.09931661259
DarkChem[M-H]-127.87331661259
DeepCCS[M+H]+129.09830932474
DeepCCS[M-H]-126.47830932474
DeepCCS[M-2H]-162.1830932474
DeepCCS[M+Na]+137.54630932474
AllCCS[M+H]+135.132859911
AllCCS[M+H-H2O]+131.132859911
AllCCS[M+NH4]+138.932859911
AllCCS[M+Na]+139.932859911
AllCCS[M-H]-129.332859911
AllCCS[M+Na-2H]-131.732859911
AllCCS[M+HCOO]-134.332859911

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. 1.43 minutes32390414
Predicted by Siyang on May 30, 202210.2675 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.56 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid118.2 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1088.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid328.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid77.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid180.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid57.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid338.6 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 Acid358.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)110.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid676.5 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid204.3 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid980.8 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid216.0 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid260.5 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate446.4 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA268.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water191.4 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-2,3-Dihydroxy-3-methylvalerateCC[C@@](C)(O)[C@@H](O)C(O)=O2416.1Standard polar33892256
(R)-2,3-Dihydroxy-3-methylvalerateCC[C@@](C)(O)[C@@H](O)C(O)=O1174.6Standard non polar33892256
(R)-2,3-Dihydroxy-3-methylvalerateCC[C@@](C)(O)[C@@H](O)C(O)=O1244.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-2,3-Dihydroxy-3-methylvalerate,1TMS,isomer #1CC[C@@](C)(O[Si](C)(C)C)[C@@H](O)C(=O)O1346.4Semi standard non polar33892256
(R)-2,3-Dihydroxy-3-methylvalerate,1TMS,isomer #2CC[C@@](C)(O)[C@@H](O[Si](C)(C)C)C(=O)O1320.4Semi standard non polar33892256
(R)-2,3-Dihydroxy-3-methylvalerate,1TMS,isomer #3CC[C@@](C)(O)[C@@H](O)C(=O)O[Si](C)(C)C1246.6Semi standard non polar33892256
(R)-2,3-Dihydroxy-3-methylvalerate,2TMS,isomer #1CC[C@@](C)(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O1421.4Semi standard non polar33892256
(R)-2,3-Dihydroxy-3-methylvalerate,2TMS,isomer #2CC[C@@](C)(O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C1382.9Semi standard non polar33892256
(R)-2,3-Dihydroxy-3-methylvalerate,2TMS,isomer #3CC[C@@](C)(O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1324.9Semi standard non polar33892256
(R)-2,3-Dihydroxy-3-methylvalerate,3TMS,isomer #1CC[C@@](C)(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1458.7Semi standard non polar33892256
(R)-2,3-Dihydroxy-3-methylvalerate,1TBDMS,isomer #1CC[C@@](C)(O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O1600.4Semi standard non polar33892256
(R)-2,3-Dihydroxy-3-methylvalerate,1TBDMS,isomer #2CC[C@@](C)(O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O1562.3Semi standard non polar33892256
(R)-2,3-Dihydroxy-3-methylvalerate,1TBDMS,isomer #3CC[C@@](C)(O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C1482.8Semi standard non polar33892256
(R)-2,3-Dihydroxy-3-methylvalerate,2TBDMS,isomer #1CC[C@@](C)(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O1863.2Semi standard non polar33892256
(R)-2,3-Dihydroxy-3-methylvalerate,2TBDMS,isomer #2CC[C@@](C)(O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C1827.9Semi standard non polar33892256
(R)-2,3-Dihydroxy-3-methylvalerate,2TBDMS,isomer #3CC[C@@](C)(O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1805.4Semi standard non polar33892256
(R)-2,3-Dihydroxy-3-methylvalerate,3TBDMS,isomer #1CC[C@@](C)(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2102.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9000000000-d382043e81321879e92e2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate GC-MS (3 TMS) - 70eV, Positivesplash10-00tb-9464000000-0280de9eaa4c123339972017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 10V, Positive-QTOFsplash10-05aj-7900000000-ed4255c918254a1dc4622015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 20V, Positive-QTOFsplash10-0kar-9600000000-420faa83ea76001db2e92015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 40V, Positive-QTOFsplash10-0pb9-9000000000-393b15b5811231e326932015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 10V, Negative-QTOFsplash10-0udj-2900000000-d582074beb8b89338fa52015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 20V, Negative-QTOFsplash10-00di-9400000000-5ee3e425ebda8358d3372015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 40V, Negative-QTOFsplash10-05g0-9000000000-db72ead6bd87a129b3252015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 10V, Positive-QTOFsplash10-0h32-2900000000-0dc4c2a3c02313bed77c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 20V, Positive-QTOFsplash10-0a4i-9000000000-431db2e8dea59bdd5c382021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 40V, Positive-QTOFsplash10-0a4i-9000000000-349f8877717c1418480e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 10V, Negative-QTOFsplash10-0002-0900000000-81689c0553421abfcd882021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 20V, Negative-QTOFsplash10-004i-9100000000-d9815468ea9acf930e9e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 40V, Negative-QTOFsplash10-052f-9100000000-f894bf4ab44aaac795012021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)2022-02-11FELIX 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+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 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 IDDB03675
Phenol Explorer Compound IDNot Available
FooDB IDFDB028798
KNApSAcK IDNot Available
Chemspider ID395044
KEGG Compound IDC06007
BioCyc ID1-KETO-2-METHYLVALERATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound448154
PDB IDDMV
ChEBI ID27512
Food Biomarker OntologyNot Available
VMH ID23DHMP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.