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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-10-08 15:56:50 UTC

Update Date

2023-02-21 17:30:33 UTC

HMDB ID

HMDB0061896

Secondary Accession Numbers

HMDB61896

Metabolite Identification

Common Name

2-Methyl-3-hexanone

Description

2-Methyl-3-hexanone belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. 2-Methyl-3-hexanone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₇H₁₄O

Average Molecular Weight

114.1855

Monoisotopic Molecular Weight

114.10446507

IUPAC Name

2-methylhexan-3-one

Traditional Name

2-methyl-3-hexanone

CAS Registry Number

Not Available

SMILES

CCCC(=O)C(C)C

InChI Identifier

InChI=1S/C7H14O/c1-4-5-7(8)6(2)3/h6H,4-5H2,1-3H3

InChI Key

HIGGFWFRAWSMBR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

Excreta

Biofluid or Excreta

Feces (PMID: 21386183)

Source

Exogenous

Exogenous (HMDB: HMDB0061896)

Process

Not Available

Role

Not Available

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	5.68 g/L	ALOGPS
logP	2	ALOGPS
logP	2.49	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	34.62 m³·mol⁻¹	ChemAxon
Polarizability	13.97 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	125.84	31661259
DarkChem	[M-H]-	120.553	31661259
DeepCCS	[M+H]+	129.395	30932474
DeepCCS	[M-H]-	127.168	30932474
DeepCCS	[M-2H]-	163.359	30932474
DeepCCS	[M+Na]+	138.094	30932474
AllCCS	[M+H]+	128.1	32859911
AllCCS	[M+H-H2O]+	123.8	32859911
AllCCS	[M+NH4]+	132.0	32859911
AllCCS	[M+Na]+	133.2	32859911
AllCCS	[M-H]-	131.8	32859911
AllCCS	[M+Na-2H]-	135.1	32859911
AllCCS	[M+HCOO]-	138.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methyl-3-hexanone	CCCC(=O)C(C)C	1129.0	Standard polar	33892256
2-Methyl-3-hexanone	CCCC(=O)C(C)C	805.8	Standard non polar	33892256
2-Methyl-3-hexanone	CCCC(=O)C(C)C	828.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Methyl-3-hexanone,1TMS,isomer #1	CCCC(O[Si](C)(C)C)=C(C)C	1064.6	Semi standard non polar	33892256
2-Methyl-3-hexanone,1TMS,isomer #1	CCCC(O[Si](C)(C)C)=C(C)C	1009.8	Standard non polar	33892256
2-Methyl-3-hexanone,1TMS,isomer #1	CCCC(O[Si](C)(C)C)=C(C)C	1047.6	Standard polar	33892256
2-Methyl-3-hexanone,1TMS,isomer #2	CCC=C(O[Si](C)(C)C)C(C)C	1029.5	Semi standard non polar	33892256
2-Methyl-3-hexanone,1TMS,isomer #2	CCC=C(O[Si](C)(C)C)C(C)C	976.9	Standard non polar	33892256
2-Methyl-3-hexanone,1TMS,isomer #2	CCC=C(O[Si](C)(C)C)C(C)C	1047.9	Standard polar	33892256
2-Methyl-3-hexanone,1TBDMS,isomer #1	CCCC(O[Si](C)(C)C(C)(C)C)=C(C)C	1278.5	Semi standard non polar	33892256
2-Methyl-3-hexanone,1TBDMS,isomer #1	CCCC(O[Si](C)(C)C(C)(C)C)=C(C)C	1206.5	Standard non polar	33892256
2-Methyl-3-hexanone,1TBDMS,isomer #1	CCCC(O[Si](C)(C)C(C)(C)C)=C(C)C	1245.0	Standard polar	33892256
2-Methyl-3-hexanone,1TBDMS,isomer #2	CCC=C(O[Si](C)(C)C(C)(C)C)C(C)C	1236.9	Semi standard non polar	33892256
2-Methyl-3-hexanone,1TBDMS,isomer #2	CCC=C(O[Si](C)(C)C(C)(C)C)C(C)C	1191.9	Standard non polar	33892256
2-Methyl-3-hexanone,1TBDMS,isomer #2	CCC=C(O[Si](C)(C)C(C)(C)C)C(C)C	1238.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methyl-3-hexanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9000000000-833bdecae48d0f3b1c57	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methyl-3-hexanone 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 - 2-Methyl-3-hexanone 10V, Positive-QTOF	splash10-014i-4900000000-558aa97324f4265a2296	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-hexanone 20V, Positive-QTOF	splash10-00di-9200000000-f13decb942509f88d110	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-hexanone 40V, Positive-QTOF	splash10-0596-9000000000-444bd08e37b8d3322303	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-hexanone 10V, Negative-QTOF	splash10-03di-1900000000-8bb0acc3af5af6f6165b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-hexanone 20V, Negative-QTOF	splash10-03di-6900000000-1f1ee6aa65f212bcb720	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-hexanone 40V, Negative-QTOF	splash10-01c0-9000000000-b736e3891021ef45ef87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-hexanone 10V, Positive-QTOF	splash10-0aos-9000000000-1675947f0bd3b3f778ae	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-hexanone 20V, Positive-QTOF	splash10-053r-9000000000-357f5165ed76ae5a0cda	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-hexanone 40V, Positive-QTOF	splash10-0006-9000000000-9df076ce65febaabacf8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-hexanone 10V, Negative-QTOF	splash10-03di-0900000000-87ba7764343ecec4c93f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-hexanone 20V, Negative-QTOF	splash10-03xs-9500000000-86d0873c41af22b863aa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-hexanone 40V, Negative-QTOF	splash10-00kf-9000000000-e99a965d424077c1451e	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

Feces
Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	23454028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23454028	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Both	Normal	21386183	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Nonalcoholic fatty liver disease	23454028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	details

Associated Disorders and Diseases

Disease References

Nonalcoholic fatty liver disease
Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23847

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

Patil VR, Donde KJ, Jadhav SB, Malve SP: Synthesis and antimicrobial activity of 3-hydroxyimino-5-methyl-2-hexanone(HIMH) and its dioxime derivative. Acta Pol Pharm. 2002 May-Jun;59(3):223-5. [PubMed:12230250 ]
Donde KJ, Patil VR, Utekar SS, Malve SP: Synthesis, structural characterization and antimicrobial studies of hydrazone derivatives of 3-hydroxyimino-5-methyl-2-hexanone. Acta Pol Pharm. 2002 Jul-Aug;59(4):291-3. [PubMed:12403304 ]
Kaiser EW, Wallington TJ: Rate constants for the reaction of cl with a series of C4 to C6 ketones using the relative rate method. J Phys Chem A. 2007 Oct 25;111(42):10667-70. Epub 2007 Oct 3. [PubMed:17914780 ]
Tamura H, Fujita A, Steinhaus M, Takahisa E, Watanabe H, Schieberle P: Assessment of the aroma impact of major odor-active thiols in pan-roasted white sesame seeds by calculation of odor activity values. J Agric Food Chem. 2011 Sep 28;59(18):10211-8. doi: 10.1021/jf202183y. Epub 2011 Aug 23. [PubMed:21815692 ]
Pierre-Alain Blanc, 'Oxime as perfuming ingredient.' U.S. Patent US20030069167, issued April 10, 2003. [Link]
Lloyd Berg, Zuyin Yang, 'Separation of methylene chloride from the lower formates by extractive distillation.' U.S. Patent US5094724, issued June, 1980. [Link]
Pierre-Alain Blanc, Piero Fantini, Peter Fankhauser, 'Oxime as perfuming ingredient.' U.S. Patent US06872697, issued March 29, 2005. [Link]
Peter E. A. Teal, Hans T. Alborn, Paul W. Sternberg, Jagan Srinivasan, Arthur S. Edison, Fatma Kaplan, Frank C. Schroeder, 'Ascarosides as nematode sex pheromones.' U.S. Patent US08318146, issued November 27, 2012. [Link]

Showing metabocard for 2-Methyl-3-hexanone (HMDB0061896)

MOL for HMDB0061896 (2-Methyl-3-hexanone)

3D MOL for HMDB0061896 (2-Methyl-3-hexanone)

3D SDF for HMDB0061896 (2-Methyl-3-hexanone)

3D-SDF for HMDB0061896 (2-Methyl-3-hexanone)

PDB for HMDB0061896 (2-Methyl-3-hexanone)

3D PDB for HMDB0061896 (2-Methyl-3-hexanone)

SMILES for HMDB0061896 (2-Methyl-3-hexanone)

INCHI for HMDB0061896 (2-Methyl-3-hexanone)

Structure for HMDB0061896 (2-Methyl-3-hexanone)

3D Structure for HMDB0061896 (2-Methyl-3-hexanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra