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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:48:46 UTC

Update Date

2022-03-07 02:53:17 UTC

HMDB ID

HMDB0032258

Secondary Accession Numbers

HMDB32258

Metabolite Identification

Common Name

(+/-)-Ethyl 3-acetoxy-2-methylbutyrate

Description

(+/-)-Ethyl 3-acetoxy-2-methylbutyrate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Based on a literature review a significant number of articles have been published on (+/-)-Ethyl 3-acetoxy-2-methylbutyrate.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0032258
     RDKit          3D
(+/-)-Ethyl 3-acetoxy-2-methylbutyrate
 29 28  0  0  0  0  0  0  0  0999 V2000
    2.9652    2.3158   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2601    1.0150    0.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4183   -0.0341    0.1535 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0446   -0.0348    0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5160    0.9776    0.8014 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2516   -1.1992   -0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -2.4302    0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2051   -1.0600    0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8813   -2.3223   -0.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8076    0.0202   -0.6132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4903    0.9951    0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1468    2.1600   -0.5687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5291    0.8476    1.3499 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9930    2.1818   -1.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9973    2.6922    0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417    3.0423    0.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2801    1.1615    1.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3045    0.7116    0.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4745   -1.4391   -1.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4878   -3.3626    0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209   -2.3558    0.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2441   -2.4674    1.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3665   -0.9797    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8633   -3.0522    0.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461   -2.7292   -1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9233   -2.1004   -0.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1682    1.9036   -0.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5086    2.6125   -1.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2904    2.9302    0.2257 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
  4  5  2  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 12 27  1  0
 12 28  1  0
 12 29  1  0
M  END

HMDB0032258
     RDKit          3D
(+/-)-Ethyl 3-acetoxy-2-methylbutyrate
 29 28  0  0  0  0  0  0  0  0999 V2000
    2.9652    2.3158   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2601    1.0150    0.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4183   -0.0341    0.1535 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0446   -0.0348    0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5160    0.9776    0.8014 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2516   -1.1992   -0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -2.4302    0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2051   -1.0600    0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8813   -2.3223   -0.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8076    0.0202   -0.6132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4903    0.9951    0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1468    2.1600   -0.5687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5291    0.8476    1.3499 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9930    2.1818   -1.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9973    2.6922    0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417    3.0423    0.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2801    1.1615    1.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3045    0.7116    0.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4745   -1.4391   -1.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4878   -3.3626    0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209   -2.3558    0.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2441   -2.4674    1.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3665   -0.9797    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8633   -3.0522    0.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461   -2.7292   -1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9233   -2.1004   -0.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1682    1.9036   -0.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5086    2.6125   -1.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2904    2.9302    0.2257 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
  4  5  2  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 12 27  1  0
 12 28  1  0
 12 29  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -6.724  -3.231   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.389  -1.691   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.055  -5.541   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.946  -3.231   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.390  -4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.389  -3.231   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.055  -4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.612  -4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.723  -4.001   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.612  -5.541   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.723  -5.541   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.056  -3.231   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.278  -3.231   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3    7                                                            
CONECT    4    8                                                            
CONECT    5    1   12                                                       
CONECT    6    2    7    9                                                  
CONECT    7    3    6   13                                                  
CONECT    8    4   10   13                                                  
CONECT    9    6   11   12                                                  
CONECT   10    8                                                            
CONECT   11    9                                                            
CONECT   12    5    9                                                       
CONECT   13    7    8                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

COMPND    HMDB0032258
HETATM    1  C1  UNL     1       2.965   2.316  -0.124  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.260   1.015   0.565  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.418  -0.034   0.153  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.045  -0.035   0.280  1.00  0.00           C  
HETATM    5  O2  UNL     1       0.516   0.978   0.801  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.252  -1.199  -0.189  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.727  -2.430   0.595  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.205  -1.060   0.071  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.881  -2.322  -0.463  1.00  0.00           C  
HETATM   10  O3  UNL     1      -1.808   0.020  -0.613  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.490   0.995   0.100  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.147   2.160  -0.569  1.00  0.00           C  
HETATM   13  O4  UNL     1      -2.529   0.848   1.350  1.00  0.00           O  
HETATM   14  H1  UNL     1       2.993   2.182  -1.225  1.00  0.00           H  
HETATM   15  H2  UNL     1       1.997   2.692   0.228  1.00  0.00           H  
HETATM   16  H3  UNL     1       3.742   3.042   0.189  1.00  0.00           H  
HETATM   17  H4  UNL     1       3.280   1.161   1.662  1.00  0.00           H  
HETATM   18  H5  UNL     1       4.304   0.712   0.277  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.475  -1.439  -1.255  1.00  0.00           H  
HETATM   20  H7  UNL     1       0.488  -3.363   0.081  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.821  -2.356   0.745  1.00  0.00           H  
HETATM   22  H9  UNL     1       0.244  -2.467   1.593  1.00  0.00           H  
HETATM   23  H10 UNL     1      -1.367  -0.980   1.172  1.00  0.00           H  
HETATM   24  H11 UNL     1      -1.863  -3.052   0.346  1.00  0.00           H  
HETATM   25  H12 UNL     1      -1.346  -2.729  -1.348  1.00  0.00           H  
HETATM   26  H13 UNL     1      -2.923  -2.100  -0.814  1.00  0.00           H  
HETATM   27  H14 UNL     1      -4.168   1.904  -0.930  1.00  0.00           H  
HETATM   28  H15 UNL     1      -2.509   2.613  -1.345  1.00  0.00           H  
HETATM   29  H16 UNL     1      -3.290   2.930   0.226  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   17   18
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    8   19
CONECT    7   20   21   22
CONECT    8    9   10   23
CONECT    9   24   25   26
CONECT   10   11
CONECT   11   12   13   13
CONECT   12   27   28   29
END

HMDB0032258
     RDKit          3D
(+/-)-Ethyl 3-acetoxy-2-methylbutyrate
 29 28  0  0  0  0  0  0  0  0999 V2000
    2.9652    2.3158   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2601    1.0150    0.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4183   -0.0341    0.1535 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0446   -0.0348    0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5160    0.9776    0.8014 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2516   -1.1992   -0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -2.4302    0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2051   -1.0600    0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8813   -2.3223   -0.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8076    0.0202   -0.6132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4903    0.9951    0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1468    2.1600   -0.5687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5291    0.8476    1.3499 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9930    2.1818   -1.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9973    2.6922    0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417    3.0423    0.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2801    1.1615    1.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3045    0.7116    0.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4745   -1.4391   -1.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4878   -3.3626    0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209   -2.3558    0.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2441   -2.4674    1.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3665   -0.9797    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8633   -3.0522    0.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461   -2.7292   -1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9233   -2.1004   -0.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1682    1.9036   -0.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5086    2.6125   -1.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2904    2.9302    0.2257 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
  4  5  2  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 12 27  1  0
 12 28  1  0
 12 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+/-)-ethyl 3-acetoxy-2-methylbutyric acid	Generator

Chemical Formula

C₉H₁₆O₄

Average Molecular Weight

188.2209

Monoisotopic Molecular Weight

188.104859

IUPAC Name

ethyl 3-(acetyloxy)-2-methylbutanoate

Traditional Name

ethyl 3-(acetyloxy)-2-methylbutanoate

CAS Registry Number

139564-43-5

SMILES

CCOC(=O)C(C)C(C)OC(C)=O

InChI Identifier

InChI=1S/C9H16O4/c1-5-12-9(11)6(2)7(3)13-8(4)10/h6-7H,5H2,1-4H3

InChI Key

KYWLAHNPWLJLDJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Odor

Fruity

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0032258)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032258)

Source

Endogenous

Endogenous (HMDB: HMDB0032258)

Animal

Animal (HMDB: HMDB0032258)

Exogenous

Food

Food (HMDB: HMDB0032258)

Exogenous (HMDB: HMDB0032258)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0032258)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0032258)

Lipid metabolism pathway (HMDB: HMDB0032258)

Cellular process

Cell signaling (HMDB: HMDB0032258)

Biochemical process

Lipid transport (HMDB: HMDB0032258)

Role

Biological role

Energy source (HMDB: HMDB0032258)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032258)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.6 g/L	ALOGPS
logP	1.62	ALOGPS
logP	1.1	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	46.71 m³·mol⁻¹	ChemAxon
Polarizability	19.78 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	144.311	31661259
DarkChem	[M-H]-	139.807	31661259
DeepCCS	[M+H]+	147.687	30932474
DeepCCS	[M-H]-	143.86	30932474
DeepCCS	[M-2H]-	180.85	30932474
DeepCCS	[M+Na]+	156.512	30932474
AllCCS	[M+H]+	143.9	32859911
AllCCS	[M+H-H2O]+	140.3	32859911
AllCCS	[M+NH4]+	147.2	32859911
AllCCS	[M+Na]+	148.2	32859911
AllCCS	[M-H]-	144.1	32859911
AllCCS	[M+Na-2H]-	145.7	32859911
AllCCS	[M+HCOO]-	147.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	5.36 minutes	32390414
Predicted by Siyang on May 30, 2022	13.1175 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.65 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1909.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	374.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	125.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	200.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	63.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	454.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	511.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	73.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	976.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	412.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1394.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	305.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	319.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	427.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	311.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	65.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+/-)-Ethyl 3-acetoxy-2-methylbutyrate	CCOC(=O)C(C)C(C)OC(C)=O	1641.2	Standard polar	33892256
(+/-)-Ethyl 3-acetoxy-2-methylbutyrate	CCOC(=O)C(C)C(C)OC(C)=O	1148.6	Standard non polar	33892256
(+/-)-Ethyl 3-acetoxy-2-methylbutyrate	CCOC(=O)C(C)C(C)OC(C)=O	1174.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (+/-)-Ethyl 3-acetoxy-2-methylbutyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0173-9600000000-3c1b7bd3c8b625eecac0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+/-)-Ethyl 3-acetoxy-2-methylbutyrate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+/-)-Ethyl 3-acetoxy-2-methylbutyrate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 3-acetoxy-2-methylbutyrate 10V, Positive-QTOF	splash10-000i-1900000000-52560a3924f37666893f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 3-acetoxy-2-methylbutyrate 20V, Positive-QTOF	splash10-0fbm-3900000000-dcb8cf69ea185f7decb5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 3-acetoxy-2-methylbutyrate 40V, Positive-QTOF	splash10-0kmi-9300000000-e1a941b087a80fccc831	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 3-acetoxy-2-methylbutyrate 10V, Negative-QTOF	splash10-000i-1900000000-f68520c9ff6634255293	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 3-acetoxy-2-methylbutyrate 20V, Negative-QTOF	splash10-05mw-7900000000-bc76868261cfd9f173d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 3-acetoxy-2-methylbutyrate 40V, Negative-QTOF	splash10-05fr-9300000000-c50009f3fb7fc791c8aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 3-acetoxy-2-methylbutyrate 10V, Negative-QTOF	splash10-0a4i-9200000000-f10953a6633b17f5b7bc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 3-acetoxy-2-methylbutyrate 20V, Negative-QTOF	splash10-0a4i-9000000000-37ca757a00c1316bc087	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 3-acetoxy-2-methylbutyrate 40V, Negative-QTOF	splash10-0a4i-9000000000-d84e8a96e967cb27ada9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 3-acetoxy-2-methylbutyrate 10V, Positive-QTOF	splash10-053i-9400000000-515049cf95730733fdd6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 3-acetoxy-2-methylbutyrate 20V, Positive-QTOF	splash10-0pc0-9400000000-388de09cfb52c164f8ed	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 3-acetoxy-2-methylbutyrate 40V, Positive-QTOF	splash10-0a4i-9000000000-e868ee0efcc19eeee490	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB009370

KNApSAcK ID

Not Available

Chemspider ID

231585

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

263620

PDB ID

Not Available

ChEBI ID

143033

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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 ]
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 ]
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 ]
(). EAFUS: Everything Added to Food in the United States.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (+/-)-Ethyl 3-acetoxy-2-methylbutyrate (HMDB0032258)

MOL for HMDB0032258 ((+/-)-Ethyl 3-acetoxy-2-methylbutyrate)

3D MOL for HMDB0032258 ((+/-)-Ethyl 3-acetoxy-2-methylbutyrate)

3D SDF for HMDB0032258 ((+/-)-Ethyl 3-acetoxy-2-methylbutyrate)

3D-SDF for HMDB0032258 ((+/-)-Ethyl 3-acetoxy-2-methylbutyrate)

PDB for HMDB0032258 ((+/-)-Ethyl 3-acetoxy-2-methylbutyrate)

3D PDB for HMDB0032258 ((+/-)-Ethyl 3-acetoxy-2-methylbutyrate)

SMILES for HMDB0032258 ((+/-)-Ethyl 3-acetoxy-2-methylbutyrate)

INCHI for HMDB0032258 ((+/-)-Ethyl 3-acetoxy-2-methylbutyrate)

Structure for HMDB0032258 ((+/-)-Ethyl 3-acetoxy-2-methylbutyrate)

3D Structure for HMDB0032258 ((+/-)-Ethyl 3-acetoxy-2-methylbutyrate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra