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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:34:15 UTC

Update Date

2021-09-26 22:54:00 UTC

HMDB ID

HMDB0245506

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,5-Hexanedione

Description

2,5-Hexanedione, also known as acetonyl acetone or 2,5-diketohexane, 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. Thus, 2,5-hexanedione is considered to be an oxygenated hydrocarbon. 2,5-Hexanedione is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on 2,5-Hexanedione. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,5-hexanedione is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,5-Hexanedione is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,2-Diacetylethane	ChEBI
2,5-Diketohexane	ChEBI
2,5-Hexadione	ChEBI
Acetonyl acetone	ChEBI
Acetonylacetone	ChEBI
alpha,beta-Diacetylethane	ChEBI
CH3COCH2CH2COCH3	ChEBI
Hexane-2,5-dione	ChEBI
NSC 7621	ChEBI
a,b-Diacetylethane	Generator
Α,β-diacetylethane	Generator
alpha, beta-Diacetylethane	HMDB
Diacetonyl	HMDB
2,5-Dioxohexane	HMDB
Acetone, acetonyl	HMDB

Chemical Formula

C₆H₁₀O₂

Average Molecular Weight

114.1424

Monoisotopic Molecular Weight

114.068079564

IUPAC Name

hexane-2,5-dione

Traditional Name

2,5-hexanedione

CAS Registry Number

Not Available

SMILES

CC(=O)CCC(C)=O

InChI Identifier

InChI=1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3

InChI Key

OJVAMHKKJGICOG-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

methyl ketone (CHEBI:85014 )
diketone (CHEBI:85014 )
Oxygenated hydrocarbons (LMFA12000081 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Cytoplasm (HMDB: HMDB0245506)
Membrane (HMDB: HMDB0245506)
Cell surface (HMDB: HMDB0245506)
Synaptic vesicle (HMDB: HMDB0245506)
Microtubule (HMDB: HMDB0245506)
Microtubule (HMDB: HMDB0245506)
Actin filament (HMDB: HMDB0245506)
Intermediate filament (HMDB: HMDB0245506)
Extracellular (HMDB: HMDB0245506)
Cytosol (HMDB: HMDB0245506)
Perinuclear region (HMDB: HMDB0245506)

Macromolecular complex

Cytoskeleton (HMDB: HMDB0245506)

Organelle

Mitochondrion (HMDB: HMDB0245506)
Endoplasmic reticulum (HMDB: HMDB0245506)

Tissue substructure

Nerve (HMDB: HMDB0245506)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Naturally occurring process

Biological process

Cellular process

Apoptosis (HMDB: HMDB0245506)

Biochemical pathway

Metabolic pathway

Metabolic Pathways (HMDB: HMDB0245506)
Pentose Phosphate Pathway (HMDB: HMDB0245506)

Physiological pathway

DNA replication (HMDB: HMDB0245506)

Biochemical process

Cell cycle (HMDB: HMDB0245506)

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
logP	0.28	ALOGPS
logP	0.26	ChemAxon
logS	-0.35	ALOGPS
pKa (Strongest Acidic)	17.73	ChemAxon
pKa (Strongest Basic)	-7	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	30.64 m³·mol⁻¹	ChemAxon
Polarizability	12.25 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
DeepCCS	[M+H]+	126.152	30932474
DeepCCS	[M-H]-	124.115	30932474
DeepCCS	[M-2H]-	159.845	30932474
DeepCCS	[M+Na]+	134.528	30932474
AllCCS	[M+H]+	126.6	32859911
AllCCS	[M+H-H2O]+	122.2	32859911
AllCCS	[M+NH4]+	130.6	32859911
AllCCS	[M+Na]+	131.8	32859911
AllCCS	[M-H]-	127.3	32859911
AllCCS	[M+Na-2H]-	130.6	32859911
AllCCS	[M+HCOO]-	134.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,5-Hexanedione	CC(=O)CCC(C)=O	1512.3	Standard polar	33892256
2,5-Hexanedione	CC(=O)CCC(C)=O	884.6	Standard non polar	33892256
2,5-Hexanedione	CC(=O)CCC(C)=O	925.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,5-Hexanedione,1TMS,isomer #1	CC(=O)CC=C(C)O[Si](C)(C)C	1153.1	Semi standard non polar	33892256
2,5-Hexanedione,1TMS,isomer #1	CC(=O)CC=C(C)O[Si](C)(C)C	1106.7	Standard non polar	33892256
2,5-Hexanedione,1TMS,isomer #1	CC(=O)CC=C(C)O[Si](C)(C)C	1301.4	Standard polar	33892256
2,5-Hexanedione,1TMS,isomer #2	C=C(CCC(C)=O)O[Si](C)(C)C	1129.2	Semi standard non polar	33892256
2,5-Hexanedione,1TMS,isomer #2	C=C(CCC(C)=O)O[Si](C)(C)C	1101.6	Standard non polar	33892256
2,5-Hexanedione,1TMS,isomer #2	C=C(CCC(C)=O)O[Si](C)(C)C	1334.7	Standard polar	33892256
2,5-Hexanedione,2TMS,isomer #1	CC(=CC=C(C)O[Si](C)(C)C)O[Si](C)(C)C	1368.7	Semi standard non polar	33892256
2,5-Hexanedione,2TMS,isomer #1	CC(=CC=C(C)O[Si](C)(C)C)O[Si](C)(C)C	1274.2	Standard non polar	33892256
2,5-Hexanedione,2TMS,isomer #1	CC(=CC=C(C)O[Si](C)(C)C)O[Si](C)(C)C	1264.6	Standard polar	33892256
2,5-Hexanedione,2TMS,isomer #2	C=C(CC=C(C)O[Si](C)(C)C)O[Si](C)(C)C	1316.3	Semi standard non polar	33892256
2,5-Hexanedione,2TMS,isomer #2	C=C(CC=C(C)O[Si](C)(C)C)O[Si](C)(C)C	1267.3	Standard non polar	33892256
2,5-Hexanedione,2TMS,isomer #2	C=C(CC=C(C)O[Si](C)(C)C)O[Si](C)(C)C	1271.2	Standard polar	33892256
2,5-Hexanedione,2TMS,isomer #3	C=C(CCC(=C)O[Si](C)(C)C)O[Si](C)(C)C	1263.1	Semi standard non polar	33892256
2,5-Hexanedione,2TMS,isomer #3	C=C(CCC(=C)O[Si](C)(C)C)O[Si](C)(C)C	1291.6	Standard non polar	33892256
2,5-Hexanedione,2TMS,isomer #3	C=C(CCC(=C)O[Si](C)(C)C)O[Si](C)(C)C	1290.5	Standard polar	33892256
2,5-Hexanedione,1TBDMS,isomer #1	CC(=O)CC=C(C)O[Si](C)(C)C(C)(C)C	1369.7	Semi standard non polar	33892256
2,5-Hexanedione,1TBDMS,isomer #1	CC(=O)CC=C(C)O[Si](C)(C)C(C)(C)C	1314.8	Standard non polar	33892256
2,5-Hexanedione,1TBDMS,isomer #1	CC(=O)CC=C(C)O[Si](C)(C)C(C)(C)C	1466.4	Standard polar	33892256
2,5-Hexanedione,1TBDMS,isomer #2	C=C(CCC(C)=O)O[Si](C)(C)C(C)(C)C	1341.5	Semi standard non polar	33892256
2,5-Hexanedione,1TBDMS,isomer #2	C=C(CCC(C)=O)O[Si](C)(C)C(C)(C)C	1302.4	Standard non polar	33892256
2,5-Hexanedione,1TBDMS,isomer #2	C=C(CCC(C)=O)O[Si](C)(C)C(C)(C)C	1489.8	Standard polar	33892256
2,5-Hexanedione,2TBDMS,isomer #1	CC(=CC=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1788.2	Semi standard non polar	33892256
2,5-Hexanedione,2TBDMS,isomer #1	CC(=CC=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1717.6	Standard non polar	33892256
2,5-Hexanedione,2TBDMS,isomer #1	CC(=CC=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1582.7	Standard polar	33892256
2,5-Hexanedione,2TBDMS,isomer #2	C=C(CC=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1759.1	Semi standard non polar	33892256
2,5-Hexanedione,2TBDMS,isomer #2	C=C(CC=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1713.9	Standard non polar	33892256
2,5-Hexanedione,2TBDMS,isomer #2	C=C(CC=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1587.8	Standard polar	33892256
2,5-Hexanedione,2TBDMS,isomer #3	C=C(CCC(=C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1690.1	Semi standard non polar	33892256
2,5-Hexanedione,2TBDMS,isomer #3	C=C(CCC(=C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1705.1	Standard non polar	33892256
2,5-Hexanedione,2TBDMS,isomer #3	C=C(CCC(=C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1607.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Hexanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-d92e1919424eac03a7b0	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Hexanedione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-32eba5bb2c4f125d9a03	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Hexanedione 10V, Positive-QTOF	splash10-014j-8900000000-0939439a09c8f7b2e93e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Hexanedione 20V, Positive-QTOF	splash10-014j-9500000000-61e195dbb4527ae29973	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Hexanedione 40V, Positive-QTOF	splash10-0fb9-9000000000-62487cfd16429e9987db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Hexanedione 10V, Negative-QTOF	splash10-03di-1900000000-4f7742ff49533756a116	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Hexanedione 20V, Negative-QTOF	splash10-03di-3900000000-5dd73a1849e09ffe97f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Hexanedione 40V, Negative-QTOF	splash10-0005-9100000000-d506ae3a57d26118dc6f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Hexanedione 10V, Positive-QTOF	splash10-002b-9000000000-c8a6489ae02a5c461b88	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Hexanedione 20V, Positive-QTOF	splash10-004i-9000000000-fdcbb1c7525a2d2b215f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Hexanedione 40V, Positive-QTOF	splash10-004l-9000000000-d90562a5cfb0bfa4edd2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Hexanedione 10V, Negative-QTOF	splash10-03di-3900000000-0eebb1bf4507776306dd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Hexanedione 20V, Negative-QTOF	splash10-0007-9100000000-057abf81800767fcc8ef	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Hexanedione 40V, Negative-QTOF	splash10-0007-9000000000-bbf5a0c5b8967d589b83	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7744

KEGG Compound ID

Not Available

BioCyc ID

CPD-15521

BiGG ID

Not Available

Wikipedia Link

Hexane-2,5-dione

METLIN ID

Not Available

PubChem Compound

8035

PDB ID

Not Available

ChEBI ID

85014

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1132601

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 2,5-Hexanedione (HMDB0245506)

MOL for HMDB0245506 (2,5-Hexanedione)

3D MOL for HMDB0245506 (2,5-Hexanedione)

3D SDF for HMDB0245506 (2,5-Hexanedione)

3D-SDF for HMDB0245506 (2,5-Hexanedione)

PDB for HMDB0245506 (2,5-Hexanedione)

3D PDB for HMDB0245506 (2,5-Hexanedione)

SMILES for HMDB0245506 (2,5-Hexanedione)

INCHI for HMDB0245506 (2,5-Hexanedione)

Structure for HMDB0245506 (2,5-Hexanedione)

3D Structure for HMDB0245506 (2,5-Hexanedione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra