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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:15 UTC

Update Date

2023-02-21 17:20:55 UTC

HMDB ID

HMDB0031593

Secondary Accession Numbers

HMDB31593

Metabolite Identification

Common Name

5-Methyl-2,3-hexanedione

Description

5-Methyl-2,3-hexanedione belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms. 5-Methyl-2,3-hexanedione is a sweet, brown, and butter tasting compound. 5-Methyl-2,3-hexanedione has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, potatos (Solanum tuberosum), and robusta coffees (Coffea canephora). This could make 5-methyl-2,3-hexanedione a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5-Methyl-2,3-hexanedione.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Methylhexa-4,5-dione	HMDB
5-Methylhexane-2,3-dione	HMDB
Acetyl isopentanoyl	HMDB
Acetyl isovaleryl	HMDB
Acetylisopentanoyl	HMDB
Acetylisovaleryl	HMDB
FEMA 3190	HMDB
Isobutyl methyl diketone	HMDB
Isobutylmethylglyoxal	HMDB

Chemical Formula

C₇H₁₂O₂

Average Molecular Weight

128.169

Monoisotopic Molecular Weight

128.083729628

IUPAC Name

5-methylhexane-2,3-dione

Traditional Name

2,3-hexanedione, 5-methyl-

CAS Registry Number

13706-86-0

SMILES

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

InChI Identifier

InChI=1S/C7H12O2/c1-5(2)4-7(9)6(3)8/h5H,4H2,1-3H3

InChI Key

PQCLJXVUAWLNSV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-diketones

Alternative Parents

Substituents

Alpha-diketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031593)
Cytoplasm (HMDB: HMDB0031593)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031593)

Source

Endogenous

Endogenous (HMDB: HMDB0031593)

Plant

Plant (HMDB: HMDB0031593)
Coffea (HMDB: HMDB0031593)

Exogenous

Food

Food (HMDB: HMDB0031593)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Exogenous (HMDB: HMDB0031593)

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	6.61 g/L	ALOGPS
logP	1.27	ALOGPS
logP	1.83	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	16.25	ChemAxon
pKa (Strongest Basic)	-8.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	35.32 m³·mol⁻¹	ChemAxon
Polarizability	14.01 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]+	129.888	31661259
DarkChem	[M-H]-	125.252	31661259
DeepCCS	[M+H]+	137.105	30932474
DeepCCS	[M-H]-	134.877	30932474
DeepCCS	[M-2H]-	171.242	30932474
DeepCCS	[M+Na]+	145.969	30932474
AllCCS	[M+H]+	129.5	32859911
AllCCS	[M+H-H2O]+	125.3	32859911
AllCCS	[M+NH4]+	133.3	32859911
AllCCS	[M+Na]+	134.5	32859911
AllCCS	[M-H]-	130.3	32859911
AllCCS	[M+Na-2H]-	133.1	32859911
AllCCS	[M+HCOO]-	136.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Methyl-2,3-hexanedione	CC(C)CC(=O)C(C)=O	1149.1	Standard polar	33892256
5-Methyl-2,3-hexanedione	CC(C)CC(=O)C(C)=O	804.6	Standard non polar	33892256
5-Methyl-2,3-hexanedione	CC(C)CC(=O)C(C)=O	853.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Methyl-2,3-hexanedione,1TMS,isomer #1	CC(=O)C(=CC(C)C)O[Si](C)(C)C	1117.3	Semi standard non polar	33892256
5-Methyl-2,3-hexanedione,1TMS,isomer #1	CC(=O)C(=CC(C)C)O[Si](C)(C)C	1076.5	Standard non polar	33892256
5-Methyl-2,3-hexanedione,1TMS,isomer #2	C=C(O[Si](C)(C)C)C(=O)CC(C)C	1145.1	Semi standard non polar	33892256
5-Methyl-2,3-hexanedione,1TMS,isomer #2	C=C(O[Si](C)(C)C)C(=O)CC(C)C	1100.9	Standard non polar	33892256
5-Methyl-2,3-hexanedione,2TMS,isomer #1	C=C(O[Si](C)(C)C)C(=CC(C)C)O[Si](C)(C)C	1263.2	Semi standard non polar	33892256
5-Methyl-2,3-hexanedione,2TMS,isomer #1	C=C(O[Si](C)(C)C)C(=CC(C)C)O[Si](C)(C)C	1261.6	Standard non polar	33892256
5-Methyl-2,3-hexanedione,1TBDMS,isomer #1	CC(=O)C(=CC(C)C)O[Si](C)(C)C(C)(C)C	1356.4	Semi standard non polar	33892256
5-Methyl-2,3-hexanedione,1TBDMS,isomer #1	CC(=O)C(=CC(C)C)O[Si](C)(C)C(C)(C)C	1288.3	Standard non polar	33892256
5-Methyl-2,3-hexanedione,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(=O)CC(C)C	1355.2	Semi standard non polar	33892256
5-Methyl-2,3-hexanedione,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(=O)CC(C)C	1281.7	Standard non polar	33892256
5-Methyl-2,3-hexanedione,2TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(=CC(C)C)O[Si](C)(C)C(C)(C)C	1693.5	Semi standard non polar	33892256
5-Methyl-2,3-hexanedione,2TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(=CC(C)C)O[Si](C)(C)C(C)(C)C	1664.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methyl-2,3-hexanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-95394dc7f793985476c5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methyl-2,3-hexanedione 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 - 5-Methyl-2,3-hexanedione 10V, Positive-QTOF	splash10-01t9-3900000000-5e05e379ff4bb7ad56f8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 20V, Positive-QTOF	splash10-0btc-9400000000-2fc37f8e6a8b9c2fd995	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 40V, Positive-QTOF	splash10-0a4i-9000000000-8449854a9e24fc33506f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 10V, Negative-QTOF	splash10-004i-2900000000-f76a0fc23c35bbf490ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 20V, Negative-QTOF	splash10-003i-9400000000-e0e4abb2a6212927d0a9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 40V, Negative-QTOF	splash10-05u6-9100000000-9dc212ff65cb65fdca63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 10V, Positive-QTOF	splash10-000f-9000000000-be00c8c4f145ec495770	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 20V, Positive-QTOF	splash10-0006-9000000000-4c884380c32d7999bfcd	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 40V, Positive-QTOF	splash10-0006-9000000000-2cf92c9ae73e11664fcb	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 10V, Negative-QTOF	splash10-004r-7900000000-fb962e2c9d27f797c84e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 20V, Negative-QTOF	splash10-0006-9000000000-f2f93da260ee7b7c4bee	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 40V, Negative-QTOF	splash10-0006-9000000000-e763a48d243c151a7266	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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

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

FDB008223

KNApSAcK ID

Not Available

Chemspider ID

24415

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

26204

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

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

Showing metabocard for 5-Methyl-2,3-hexanedione (HMDB0031593)

MOL for HMDB0031593 (5-Methyl-2,3-hexanedione)

3D MOL for HMDB0031593 (5-Methyl-2,3-hexanedione)

3D SDF for HMDB0031593 (5-Methyl-2,3-hexanedione)

3D-SDF for HMDB0031593 (5-Methyl-2,3-hexanedione)

PDB for HMDB0031593 (5-Methyl-2,3-hexanedione)

3D PDB for HMDB0031593 (5-Methyl-2,3-hexanedione)

SMILES for HMDB0031593 (5-Methyl-2,3-hexanedione)

INCHI for HMDB0031593 (5-Methyl-2,3-hexanedione)

Structure for HMDB0031593 (5-Methyl-2,3-hexanedione)

3D Structure for HMDB0031593 (5-Methyl-2,3-hexanedione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra