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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:41:59 UTC

Update Date

2023-02-21 17:20:13 UTC

HMDB ID

HMDB0031263

Secondary Accession Numbers

HMDB31263

Metabolite Identification

Common Name

2,4-Nonanedione

Description

2,4-Nonanedione, also known as caproylacetone or nonane-2,4-dione, belongs to the class of organic compounds known as beta-diketones. These are organic compounds containing two keto groups separated by a single carbon atom. Based on a literature review very few articles have been published on 2,4-Nonanedione.

Structure

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

COMPND    HMDB0031263
HETATM    1  C1  UNL     1       4.399  -0.237  -0.115  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.915  -0.528  -0.185  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.150   0.610   0.433  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.653   0.410   0.416  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.208   0.275  -0.995  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.250   0.079  -1.153  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.661  -0.037  -2.295  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.205   0.017  -0.032  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.590  -0.188  -0.519  1.00  0.00           C  
HETATM   10  C9  UNL     1      -4.779  -0.294   0.359  1.00  0.00           C  
HETATM   11  O2  UNL     1      -3.760  -0.276  -1.720  1.00  0.00           O  
HETATM   12  H1  UNL     1       4.708  -0.173   0.948  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.986  -1.014  -0.636  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.573   0.770  -0.552  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.704  -1.484   0.299  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.692  -0.588  -1.281  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.536   0.817   1.449  1.00  0.00           H  
HETATM   18  H7  UNL     1       2.370   1.539  -0.162  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.189   1.242   0.962  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.447  -0.536   0.993  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.674  -0.672  -1.399  1.00  0.00           H  
HETATM   22  H11 UNL     1       0.608   1.104  -1.602  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.228   0.974   0.567  1.00  0.00           H  
HETATM   24  H13 UNL     1      -1.976  -0.784   0.696  1.00  0.00           H  
HETATM   25  H14 UNL     1      -5.489  -1.091  -0.008  1.00  0.00           H  
HETATM   26  H15 UNL     1      -4.476  -0.578   1.384  1.00  0.00           H  
HETATM   27  H16 UNL     1      -5.398   0.642   0.351  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7    7    8
CONECT    8    9   23   24
CONECT    9   10   11   11
CONECT   10   25   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Caproylacetone	HMDB
Nonane-2,4-dione	HMDB

Chemical Formula

C₉H₁₆O₂

Average Molecular Weight

156.2221

Monoisotopic Molecular Weight

156.115029756

IUPAC Name

nonane-2,4-dione

Traditional Name

nonane-2,4-dione

CAS Registry Number

6175-23-1

SMILES

CCCCCC(=O)CC(C)=O

InChI Identifier

InChI=1S/C9H16O2/c1-3-4-5-6-9(11)7-8(2)10/h3-7H2,1-2H3

InChI Key

KFBXUKHERGLHLG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta-diketones. These are organic compounds containing two keto groups separated by a single carbon atom.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Beta-diketones

Alternative Parents

Substituents

1,3-diketone
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

Cellular substructure

Extracellular (HMDB: HMDB0031263)
Cytoplasm (HMDB: HMDB0031263)

Source

Endogenous

Endogenous (HMDB: HMDB0031263)

Exogenous

Food

Food (HMDB: HMDB0031263)

Exogenous (HMDB: HMDB0031263)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-18 °C	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	1.43 g/L	ALOGPS
logP	2.34	ALOGPS
logP	2.36	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	8.06	ChemAxon
pKa (Strongest Basic)	-7.2	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	6	ChemAxon
Refractivity	44.52 m³·mol⁻¹	ChemAxon
Polarizability	18.23 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]+	142.292	30932474
DeepCCS	[M-H]-	139.191	30932474
DeepCCS	[M-2H]-	176.514	30932474
DeepCCS	[M+Na]+	151.515	30932474
AllCCS	[M+H]+	138.6	32859911
AllCCS	[M+H-H2O]+	134.5	32859911
AllCCS	[M+NH4]+	142.3	32859911
AllCCS	[M+Na]+	143.4	32859911
AllCCS	[M-H]-	139.3	32859911
AllCCS	[M+Na-2H]-	141.2	32859911
AllCCS	[M+HCOO]-	143.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,4-Nonanedione	CCCCCC(=O)CC(C)=O	1688.9	Standard polar	33892256
2,4-Nonanedione	CCCCCC(=O)CC(C)=O	1153.9	Standard non polar	33892256
2,4-Nonanedione	CCCCCC(=O)CC(C)=O	1163.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,4-Nonanedione,1TMS,isomer #1	CCCCCC(=CC(C)=O)O[Si](C)(C)C	1401.5	Semi standard non polar	33892256
2,4-Nonanedione,1TMS,isomer #1	CCCCCC(=CC(C)=O)O[Si](C)(C)C	1360.8	Standard non polar	33892256
2,4-Nonanedione,1TMS,isomer #2	CCCCC=C(CC(C)=O)O[Si](C)(C)C	1366.8	Semi standard non polar	33892256
2,4-Nonanedione,1TMS,isomer #2	CCCCC=C(CC(C)=O)O[Si](C)(C)C	1358.8	Standard non polar	33892256
2,4-Nonanedione,1TMS,isomer #3	CCCCCC(=O)C=C(C)O[Si](C)(C)C	1385.4	Semi standard non polar	33892256
2,4-Nonanedione,1TMS,isomer #3	CCCCCC(=O)C=C(C)O[Si](C)(C)C	1349.7	Standard non polar	33892256
2,4-Nonanedione,1TMS,isomer #4	C=C(CC(=O)CCCCC)O[Si](C)(C)C	1334.1	Semi standard non polar	33892256
2,4-Nonanedione,1TMS,isomer #4	C=C(CC(=O)CCCCC)O[Si](C)(C)C	1349.2	Standard non polar	33892256
2,4-Nonanedione,2TMS,isomer #1	C=C(C=C(CCCCC)O[Si](C)(C)C)O[Si](C)(C)C	1483.3	Semi standard non polar	33892256
2,4-Nonanedione,2TMS,isomer #1	C=C(C=C(CCCCC)O[Si](C)(C)C)O[Si](C)(C)C	1515.7	Standard non polar	33892256
2,4-Nonanedione,2TMS,isomer #2	CCCCC=C(C=C(C)O[Si](C)(C)C)O[Si](C)(C)C	1550.1	Semi standard non polar	33892256
2,4-Nonanedione,2TMS,isomer #2	CCCCC=C(C=C(C)O[Si](C)(C)C)O[Si](C)(C)C	1528.8	Standard non polar	33892256
2,4-Nonanedione,2TMS,isomer #3	C=C(CC(=CCCCC)O[Si](C)(C)C)O[Si](C)(C)C	1486.9	Semi standard non polar	33892256
2,4-Nonanedione,2TMS,isomer #3	C=C(CC(=CCCCC)O[Si](C)(C)C)O[Si](C)(C)C	1522.4	Standard non polar	33892256
2,4-Nonanedione,1TBDMS,isomer #1	CCCCCC(=CC(C)=O)O[Si](C)(C)C(C)(C)C	1623.9	Semi standard non polar	33892256
2,4-Nonanedione,1TBDMS,isomer #1	CCCCCC(=CC(C)=O)O[Si](C)(C)C(C)(C)C	1563.2	Standard non polar	33892256
2,4-Nonanedione,1TBDMS,isomer #2	CCCCC=C(CC(C)=O)O[Si](C)(C)C(C)(C)C	1580.5	Semi standard non polar	33892256
2,4-Nonanedione,1TBDMS,isomer #2	CCCCC=C(CC(C)=O)O[Si](C)(C)C(C)(C)C	1557.6	Standard non polar	33892256
2,4-Nonanedione,1TBDMS,isomer #3	CCCCCC(=O)C=C(C)O[Si](C)(C)C(C)(C)C	1609.5	Semi standard non polar	33892256
2,4-Nonanedione,1TBDMS,isomer #3	CCCCCC(=O)C=C(C)O[Si](C)(C)C(C)(C)C	1557.3	Standard non polar	33892256
2,4-Nonanedione,1TBDMS,isomer #4	C=C(CC(=O)CCCCC)O[Si](C)(C)C(C)(C)C	1538.1	Semi standard non polar	33892256
2,4-Nonanedione,1TBDMS,isomer #4	C=C(CC(=O)CCCCC)O[Si](C)(C)C(C)(C)C	1541.5	Standard non polar	33892256
2,4-Nonanedione,2TBDMS,isomer #1	C=C(C=C(CCCCC)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1949.9	Semi standard non polar	33892256
2,4-Nonanedione,2TBDMS,isomer #1	C=C(C=C(CCCCC)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1895.1	Standard non polar	33892256
2,4-Nonanedione,2TBDMS,isomer #2	CCCCC=C(C=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2006.4	Semi standard non polar	33892256
2,4-Nonanedione,2TBDMS,isomer #2	CCCCC=C(C=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1913.2	Standard non polar	33892256
2,4-Nonanedione,2TBDMS,isomer #3	C=C(CC(=CCCCC)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1933.2	Semi standard non polar	33892256
2,4-Nonanedione,2TBDMS,isomer #3	C=C(CC(=CCCCC)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1904.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4-Nonanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-9000000000-acfab3fcdd4977d1a0ce	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4-Nonanedione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4-Nonanedione 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 - 2,4-Nonanedione 10V, Positive-QTOF	splash10-0a4r-1900000000-872e882fc73a0812b011	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Nonanedione 20V, Positive-QTOF	splash10-0a4s-9300000000-4224c7266121e95a0384	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Nonanedione 40V, Positive-QTOF	splash10-052f-9000000000-82158f5e4bf7ff9a8493	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Nonanedione 10V, Negative-QTOF	splash10-0a4i-1900000000-e64a718541de563c5d70	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Nonanedione 20V, Negative-QTOF	splash10-0a4i-7900000000-de27b0aa210c55719dfc	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Nonanedione 40V, Negative-QTOF	splash10-0a4i-9100000000-217733c33004bf2ce02d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Nonanedione 10V, Negative-QTOF	splash10-0a4i-1900000000-bcc9a4f563c7014375e0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Nonanedione 20V, Negative-QTOF	splash10-0bt9-9600000000-b1a9ddf4011f168f43c4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Nonanedione 40V, Negative-QTOF	splash10-0a4i-9000000000-51c46e2402ae4881e5f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Nonanedione 10V, Positive-QTOF	splash10-01ow-9200000000-1a92f8948f86c986758c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Nonanedione 20V, Positive-QTOF	splash10-0007-9000000000-eca322af892f17ac3792	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Nonanedione 40V, Positive-QTOF	splash10-0006-9000000000-a61638743121e81afd77	2021-09-22	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

FDB003304

KNApSAcK ID

Not Available

Chemspider ID

72551

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

80314

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 2,4-Nonanedione (HMDB0031263)

MOL for HMDB0031263 (2,4-Nonanedione)

3D MOL for HMDB0031263 (2,4-Nonanedione)

3D SDF for HMDB0031263 (2,4-Nonanedione)

3D-SDF for HMDB0031263 (2,4-Nonanedione)

PDB for HMDB0031263 (2,4-Nonanedione)

3D PDB for HMDB0031263 (2,4-Nonanedione)

SMILES for HMDB0031263 (2,4-Nonanedione)

INCHI for HMDB0031263 (2,4-Nonanedione)

Structure for HMDB0031263 (2,4-Nonanedione)

3D Structure for HMDB0031263 (2,4-Nonanedione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra