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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:17:09 UTC

Update Date

2023-02-21 17:25:17 UTC

HMDB ID

HMDB0036230

Secondary Accession Numbers

HMDB36230

Metabolite Identification

Common Name

1-Methyl-2-oxopropyl butyrate

Description

1-Methyl-2-oxopropyl butyrate 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 small amount of articles have been published on 1-Methyl-2-oxopropyl butyrate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Methyl-2-oxopropyl butyric acid	Generator
1-Methyl-2-oxopropyl butanoate	HMDB
2-Ketobutan-3-yl butanoate	HMDB
Acetoin butanoate	HMDB
Acetoyl butyrate	HMDB
Butan-3-one-2-yl butanoate	HMDB
Butanoic acid, 1-methyl-2-oxopropyl ester	HMDB
FEMA 3332	HMDB
Acetoin butyric acid	Generator

Chemical Formula

C₈H₁₄O₃

Average Molecular Weight

158.195

Monoisotopic Molecular Weight

158.094294314

IUPAC Name

3-oxobutan-2-yl butanoate

Traditional Name

3-oxobutan-2-yl butanoate

CAS Registry Number

84642-61-5

SMILES

CCCC(=O)OC(C)C(C)=O

InChI Identifier

InChI=1S/C8H14O3/c1-4-5-8(10)11-7(3)6(2)9/h7H,4-5H2,1-3H3

InChI Key

LJDWJXUIGKSETE-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

Alpha-acyloxy ketone
Fatty acid ester
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

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0036230)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036230)

Source

Endogenous

Endogenous (HMDB: HMDB0036230)

Animal

Animal (HMDB: HMDB0036230)

Exogenous

Food

Food (HMDB: HMDB0036230)

Exogenous (HMDB: HMDB0036230)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036230)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036230)

Lipid metabolism pathway (HMDB: HMDB0036230)

Cellular process

Cell signaling (HMDB: HMDB0036230)

Biochemical process

Lipid transport (HMDB: HMDB0036230)

Role

Biological role

Energy source (HMDB: HMDB0036230)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036230)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0036230)

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	7.18 g/L	ALOGPS
logP	1.09	ALOGPS
logP	1.44	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	17.63	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	5	ChemAxon
Refractivity	40.77 m³·mol⁻¹	ChemAxon
Polarizability	17.06 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	136.362	31661259
DarkChem	[M-H]-	133.606	31661259
DeepCCS	[M+H]+	136.086	30932474
DeepCCS	[M-H]-	132.787	30932474
DeepCCS	[M-2H]-	169.913	30932474
DeepCCS	[M+Na]+	144.955	30932474
AllCCS	[M+H]+	138.6	32859911
AllCCS	[M+H-H2O]+	134.8	32859911
AllCCS	[M+NH4]+	142.2	32859911
AllCCS	[M+Na]+	143.2	32859911
AllCCS	[M-H]-	136.8	32859911
AllCCS	[M+Na-2H]-	138.9	32859911
AllCCS	[M+HCOO]-	141.3	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.	4.35 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9847 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.32 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1938.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	447.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	161.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	277.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	119.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	530.3 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	622.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	81.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1105.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	409.7 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	1327.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	362.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	425.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	416.0 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	36.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Methyl-2-oxopropyl butyrate	CCCC(=O)OC(C)C(C)=O	1455.0	Standard polar	33892256
1-Methyl-2-oxopropyl butyrate	CCCC(=O)OC(C)C(C)=O	1000.4	Standard non polar	33892256
1-Methyl-2-oxopropyl butyrate	CCCC(=O)OC(C)C(C)=O	1072.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Methyl-2-oxopropyl butyrate,1TMS,isomer #1	CCCC(=O)OC(C)=C(C)O[Si](C)(C)C	1286.4	Semi standard non polar	33892256
1-Methyl-2-oxopropyl butyrate,1TMS,isomer #1	CCCC(=O)OC(C)=C(C)O[Si](C)(C)C	1275.9	Standard non polar	33892256
1-Methyl-2-oxopropyl butyrate,1TMS,isomer #2	C=C(O[Si](C)(C)C)C(C)OC(=O)CCC	1205.6	Semi standard non polar	33892256
1-Methyl-2-oxopropyl butyrate,1TMS,isomer #2	C=C(O[Si](C)(C)C)C(C)OC(=O)CCC	1230.5	Standard non polar	33892256
1-Methyl-2-oxopropyl butyrate,1TBDMS,isomer #1	CCCC(=O)OC(C)=C(C)O[Si](C)(C)C(C)(C)C	1498.8	Semi standard non polar	33892256
1-Methyl-2-oxopropyl butyrate,1TBDMS,isomer #1	CCCC(=O)OC(C)=C(C)O[Si](C)(C)C(C)(C)C	1481.6	Standard non polar	33892256
1-Methyl-2-oxopropyl butyrate,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(C)OC(=O)CCC	1422.6	Semi standard non polar	33892256
1-Methyl-2-oxopropyl butyrate,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(C)OC(=O)CCC	1433.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyl-2-oxopropyl butyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-30f14717685f4d674863	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyl-2-oxopropyl butyrate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyl-2-oxopropyl butyrate 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 - 1-Methyl-2-oxopropyl butyrate 10V, Positive-QTOF	splash10-05fu-9600000000-25de2321a17b10709be3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-2-oxopropyl butyrate 20V, Positive-QTOF	splash10-0fk9-9000000000-014d9a19db4ec2db1c7d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-2-oxopropyl butyrate 40V, Positive-QTOF	splash10-0fkc-9000000000-c36439812a67fd4f8b4a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-2-oxopropyl butyrate 10V, Negative-QTOF	splash10-052r-9600000000-dcc31fe147f337cef74e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-2-oxopropyl butyrate 20V, Negative-QTOF	splash10-00kr-9100000000-94581dff2b1e93723dd9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-2-oxopropyl butyrate 40V, Negative-QTOF	splash10-014u-9000000000-77d817bbaaab10b176ef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-2-oxopropyl butyrate 10V, Positive-QTOF	splash10-00dl-9000000000-244cb8044dbab21fd427	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-2-oxopropyl butyrate 20V, Positive-QTOF	splash10-006x-9000000000-9d7dd035281ba4f6426a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-2-oxopropyl butyrate 40V, Positive-QTOF	splash10-0006-9000000000-ef2d1b9e8e3a90ec98c8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-2-oxopropyl butyrate 10V, Negative-QTOF	splash10-000i-9000000000-c7be123fdea8cce640ab	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-2-oxopropyl butyrate 20V, Negative-QTOF	splash10-000i-9000000000-180de4a46000e0ff15c2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-2-oxopropyl butyrate 40V, Negative-QTOF	splash10-014u-9000000000-55f5b38038364313c210	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

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

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

FDB015088

KNApSAcK ID

Not Available

Chemspider ID

461248

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

529253

PDB ID

Not Available

ChEBI ID

Not Available

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 1-Methyl-2-oxopropyl butyrate (HMDB0036230)

MOL for HMDB0036230 (1-Methyl-2-oxopropyl butyrate)

3D MOL for HMDB0036230 (1-Methyl-2-oxopropyl butyrate)

3D SDF for HMDB0036230 (1-Methyl-2-oxopropyl butyrate)

3D-SDF for HMDB0036230 (1-Methyl-2-oxopropyl butyrate)

PDB for HMDB0036230 (1-Methyl-2-oxopropyl butyrate)

3D PDB for HMDB0036230 (1-Methyl-2-oxopropyl butyrate)

SMILES for HMDB0036230 (1-Methyl-2-oxopropyl butyrate)

INCHI for HMDB0036230 (1-Methyl-2-oxopropyl butyrate)

Structure for HMDB0036230 (1-Methyl-2-oxopropyl butyrate)

3D Structure for HMDB0036230 (1-Methyl-2-oxopropyl butyrate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra