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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:31:56 UTC

Update Date

2023-02-21 17:25:22 UTC

HMDB ID

HMDB0036396

Secondary Accession Numbers

HMDB36396

Metabolite Identification

Common Name

3-Methylbutyl 3-oxobutanoate

Description

3-Methylbutyl 3-oxobutanoate belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom. 3-Methylbutyl 3-oxobutanoate is a sweet, ethereal, and fermented tasting compound. Based on a literature review very few articles have been published on 3-Methylbutyl 3-oxobutanoate.

Structure

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

HEADER    PROTEIN                                 08-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-JAN-13         0                                  
HETATM    1  C   UNK     0       1.359   2.578   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.026   3.347   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       1.359   1.039   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.693   3.347   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.027   2.578   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.027   1.039   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.361   3.347   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.308   2.578   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.642   3.347   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.976   2.578   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.310   3.347   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.976   1.039   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    8                                                       
CONECT    3    1                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

COMPND    HMDB0036396
HETATM    1  C1  UNL     1       4.992  -0.451  -0.614  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.734   0.219  -0.170  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.781   1.375   0.196  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.461  -0.569  -0.197  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.312   0.264   0.217  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.058   1.348  -0.348  1.00  0.00           O  
HETATM    7  O3  UNL     1       0.446  -0.086   1.241  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.611   0.707   1.599  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.669   0.976   0.597  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.383  -0.243   0.090  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.074  -1.024   1.148  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.429   0.170  -0.959  1.00  0.00           C  
HETATM   13  H1  UNL     1       5.340  -1.216   0.102  1.00  0.00           H  
HETATM   14  H2  UNL     1       4.890  -0.928  -1.596  1.00  0.00           H  
HETATM   15  H3  UNL     1       5.814   0.302  -0.705  1.00  0.00           H  
HETATM   16  H4  UNL     1       2.509  -1.481   0.410  1.00  0.00           H  
HETATM   17  H5  UNL     1       2.334  -0.889  -1.278  1.00  0.00           H  
HETATM   18  H6  UNL     1      -1.053   0.335   2.567  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.187   1.715   1.893  1.00  0.00           H  
HETATM   20  H8  UNL     1      -2.424   1.629   1.083  1.00  0.00           H  
HETATM   21  H9  UNL     1      -1.244   1.594  -0.220  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.701  -0.920  -0.465  1.00  0.00           H  
HETATM   23  H11 UNL     1      -2.862  -2.114   1.059  1.00  0.00           H  
HETATM   24  H12 UNL     1      -2.836  -0.723   2.186  1.00  0.00           H  
HETATM   25  H13 UNL     1      -4.174  -0.942   1.058  1.00  0.00           H  
HETATM   26  H14 UNL     1      -4.046  -0.666  -1.280  1.00  0.00           H  
HETATM   27  H15 UNL     1      -4.094   0.971  -0.537  1.00  0.00           H  
HETATM   28  H16 UNL     1      -2.881   0.650  -1.801  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    3    4
CONECT    4    5   16   17
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   18   19
CONECT    9   10   20   21
CONECT   10   11   12   22
CONECT   11   23   24   25
CONECT   12   26   27   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Methylbutyl 3-oxobutanoic acid	Generator
3-Methylbutyl acetoacetate	HMDB
3-Methylbutyl beta-ketobutyrate	HMDB
Acetoacetic acid isoamyl ester	HMDB
Acetoacetic acid, isopentyl ester	HMDB
Butanoic acid, 3-oxo-, 3-methylbutyl ester	HMDB
FEMA 3551	HMDB
Isoamyl 3-oxobutanoate	HMDB
Isoamyl acetoacetate	HMDB
Isoamyl acetylacetate	HMDB
Isoamyl beta-ketobutyrate	HMDB
Isopentyl 3-oxobutanoate	HMDB
Isopentyl acetoacetate	HMDB
Isopentyl beta-ketobutyrate	HMDB

Chemical Formula

C₉H₁₆O₃

Average Molecular Weight

172.2215

Monoisotopic Molecular Weight

172.109944378

IUPAC Name

3-methylbutyl 3-oxobutanoate

Traditional Name

3-methylbutyl 3-oxobutanoate

CAS Registry Number

2308-18-1

SMILES

CC(C)CCOC(=O)CC(C)=O

InChI Identifier

InChI=1S/C9H16O3/c1-7(2)4-5-12-9(11)6-8(3)10/h7H,4-6H2,1-3H3

InChI Key

XHRGPLDMNNGHCX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Beta-keto acids and derivatives

Direct Parent

Beta-keto acids and derivatives

Alternative Parents

Substituents

Fatty acid ester
Beta-keto acid
Fatty acyl
1,3-dicarbonyl compound
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
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

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	89.00 to 91.00 °C. @ 6.00 mm Hg	The Good Scents Company Information System
Water Solubility	5708 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.740 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.27 g/L	ALOGPS
logP	1.34	ALOGPS
logP	1.76	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	9.93	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	45.73 m³·mol⁻¹	ChemAxon
Polarizability	19.1 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]+	140.05	31661259
DarkChem	[M-H]-	136.314	31661259
DeepCCS	[M+H]+	145.81	30932474
DeepCCS	[M-H]-	142.648	30932474
DeepCCS	[M-2H]-	179.827	30932474
DeepCCS	[M+Na]+	155.1	30932474
AllCCS	[M+H]+	141.0	32859911
AllCCS	[M+H-H2O]+	137.2	32859911
AllCCS	[M+NH4]+	144.4	32859911
AllCCS	[M+Na]+	145.4	32859911
AllCCS	[M-H]-	141.3	32859911
AllCCS	[M+Na-2H]-	143.2	32859911
AllCCS	[M+HCOO]-	145.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methylbutyl 3-oxobutanoate	CC(C)CCOC(=O)CC(C)=O	1703.4	Standard polar	33892256
3-Methylbutyl 3-oxobutanoate	CC(C)CCOC(=O)CC(C)=O	1135.5	Standard non polar	33892256
3-Methylbutyl 3-oxobutanoate	CC(C)CCOC(=O)CC(C)=O	1215.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methylbutyl 3-oxobutanoate,1TMS,isomer #1	CC(=CC(=O)OCCC(C)C)O[Si](C)(C)C	1385.7	Semi standard non polar	33892256
3-Methylbutyl 3-oxobutanoate,1TMS,isomer #1	CC(=CC(=O)OCCC(C)C)O[Si](C)(C)C	1376.7	Standard non polar	33892256
3-Methylbutyl 3-oxobutanoate,1TMS,isomer #2	C=C(CC(=O)OCCC(C)C)O[Si](C)(C)C	1340.3	Semi standard non polar	33892256
3-Methylbutyl 3-oxobutanoate,1TMS,isomer #2	C=C(CC(=O)OCCC(C)C)O[Si](C)(C)C	1352.0	Standard non polar	33892256
3-Methylbutyl 3-oxobutanoate,1TBDMS,isomer #1	CC(=CC(=O)OCCC(C)C)O[Si](C)(C)C(C)(C)C	1606.3	Semi standard non polar	33892256
3-Methylbutyl 3-oxobutanoate,1TBDMS,isomer #1	CC(=CC(=O)OCCC(C)C)O[Si](C)(C)C(C)(C)C	1571.2	Standard non polar	33892256
3-Methylbutyl 3-oxobutanoate,1TBDMS,isomer #2	C=C(CC(=O)OCCC(C)C)O[Si](C)(C)C(C)(C)C	1549.9	Semi standard non polar	33892256
3-Methylbutyl 3-oxobutanoate,1TBDMS,isomer #2	C=C(CC(=O)OCCC(C)C)O[Si](C)(C)C(C)(C)C	1546.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-Methylbutyl 3-oxobutanoate EI-B (Non-derivatized)	splash10-006x-9000000000-ea4087a7ea2378ba8ee9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Methylbutyl 3-oxobutanoate EI-B (Non-derivatized)	splash10-006x-9000000000-ea4087a7ea2378ba8ee9	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methylbutyl 3-oxobutanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-b5a7a7f3fd77fcc5bcd5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methylbutyl 3-oxobutanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methylbutyl 3-oxobutanoate 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 - 3-Methylbutyl 3-oxobutanoate 10V, Positive-QTOF	splash10-05fr-5900000000-5b85793e472e00da5a90	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 20V, Positive-QTOF	splash10-00di-9200000000-4b18b4fb8aefc4c94e58	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 40V, Positive-QTOF	splash10-0603-9000000000-9911f00c3fa9b49f25f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 10V, Negative-QTOF	splash10-00e9-8900000000-4832666a5ea86a738fb0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 20V, Negative-QTOF	splash10-0pc0-9400000000-5bddb9d4b2cecd4370cb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 40V, Negative-QTOF	splash10-0a59-9000000000-948f0c139308a9081b89	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 10V, Positive-QTOF	splash10-01bl-9400000000-9689ba6ae00740f4837e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 20V, Positive-QTOF	splash10-0006-9000000000-6a313710ef1adbcb0afd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 40V, Positive-QTOF	splash10-052f-9000000000-99bc67acbfcc650aa92c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 10V, Negative-QTOF	splash10-000i-9200000000-085ef9d84ed34f106b8c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 20V, Negative-QTOF	splash10-0a4u-9400000000-5535ebb435ed224d3af4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylbutyl 3-oxobutanoate 40V, Negative-QTOF	splash10-0a4i-9000000000-13316bf37cae9760e5be	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

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

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB015275

KNApSAcK ID

Not Available

Chemspider ID

55235

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61296

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1003181

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 3-Methylbutyl 3-oxobutanoate (HMDB0036396)

MOL for HMDB0036396 (3-Methylbutyl 3-oxobutanoate)

3D MOL for HMDB0036396 (3-Methylbutyl 3-oxobutanoate)

3D SDF for HMDB0036396 (3-Methylbutyl 3-oxobutanoate)

3D-SDF for HMDB0036396 (3-Methylbutyl 3-oxobutanoate)

PDB for HMDB0036396 (3-Methylbutyl 3-oxobutanoate)

3D PDB for HMDB0036396 (3-Methylbutyl 3-oxobutanoate)

SMILES for HMDB0036396 (3-Methylbutyl 3-oxobutanoate)

INCHI for HMDB0036396 (3-Methylbutyl 3-oxobutanoate)

Structure for HMDB0036396 (3-Methylbutyl 3-oxobutanoate)

3D Structure for HMDB0036396 (3-Methylbutyl 3-oxobutanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra