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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:37:09 UTC

Update Date

2023-02-21 17:24:21 UTC

HMDB ID

HMDB0034716

Secondary Accession Numbers

HMDB34716

Metabolite Identification

Common Name

4-Oxononanal

Description

4-Oxononanal belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. 4-Oxononanal has been detected, but not quantified in, fats and oils and fruits. This could make 4-oxononanal a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 4-Oxononanal.

Structure

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

COMPND    HMDB0034716
HETATM    1  C1  UNL     1       4.192  -0.472  -0.460  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.791  -0.528   0.170  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.181   0.841   0.006  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.804   0.905   0.595  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.083  -0.081  -0.075  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.481  -0.043   0.492  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.712   0.762   1.356  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.465  -1.009  -0.062  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.546  -0.201  -0.763  1.00  0.00           C  
HETATM   10  C9  UNL     1      -4.255   0.717   0.134  1.00  0.00           C  
HETATM   11  O2  UNL     1      -5.389   0.460   0.515  1.00  0.00           O  
HETATM   12  H1  UNL     1       4.048  -0.002  -1.463  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.792   0.196   0.201  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.635  -1.482  -0.573  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.203  -1.320  -0.315  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.887  -0.781   1.257  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.841   1.627   0.483  1.00  0.00           H  
HETATM   18  H7  UNL     1       2.196   1.106  -1.075  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.868   0.634   1.673  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.415   1.946   0.575  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.259  -1.124   0.090  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.220   0.085  -1.165  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.904  -1.652   0.736  1.00  0.00           H  
HETATM   24  H13 UNL     1      -1.980  -1.640  -0.826  1.00  0.00           H  
HETATM   25  H14 UNL     1      -4.239  -0.919  -1.260  1.00  0.00           H  
HETATM   26  H15 UNL     1      -3.030   0.338  -1.589  1.00  0.00           H  
HETATM   27  H16 UNL     1      -3.807   1.636   0.485  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   25   26
CONECT   10   11   11   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Oxononan-1-al	HMDB

Chemical Formula

C₉H₁₆O₂

Average Molecular Weight

156.2221

Monoisotopic Molecular Weight

156.115029756

IUPAC Name

4-oxononanal

Traditional Name

4-oxononanal

CAS Registry Number

74327-29-0

SMILES

CCCCCC(=O)CCC=O

InChI Identifier

InChI=1S/C9H16O2/c1-2-3-4-6-9(11)7-5-8-10/h8H,2-7H2,1H3

InChI Key

MGOKSQNXXRPCMD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Medium-chain aldehydes

Alternative Parents

Substituents

Medium-chain aldehyde
Alpha-hydrogen aldehyde
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

Membrane (HMDB: HMDB0034716)
Cell membrane (HMDB: HMDB0034716)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034716)

Source

Exogenous

Exogenous (HMDB: HMDB0034716)

Food

Food (HMDB: HMDB0034716)

Fruit

Fruits (FooDB: FOOD00871)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0034716)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034716)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	238.22 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	6438 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.582 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.13 g/L	ALOGPS
logP	2.74	ALOGPS
logP	1.81	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	12.46	ChemAxon
pKa (Strongest Basic)	-6.8	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	7	ChemAxon
Refractivity	44.59 m³·mol⁻¹	ChemAxon
Polarizability	18.37 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]+	137.833	31661259
DarkChem	[M-H]-	136.305	31661259
DeepCCS	[M+H]+	140.325	30932474
DeepCCS	[M-H]-	137.648	30932474
DeepCCS	[M-2H]-	174.593	30932474
DeepCCS	[M+Na]+	149.542	30932474
AllCCS	[M+H]+	138.8	32859911
AllCCS	[M+H-H2O]+	134.9	32859911
AllCCS	[M+NH4]+	142.5	32859911
AllCCS	[M+Na]+	143.6	32859911
AllCCS	[M-H]-	140.1	32859911
AllCCS	[M+Na-2H]-	142.0	32859911
AllCCS	[M+HCOO]-	144.2	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.	5.36 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9134 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.16 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1900.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	444.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	270.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	330.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	553.2 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	615.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	89.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1232.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	387.7 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	1259.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	346.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	348.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	414.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	408.8 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	48.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Oxononanal	CCCCCC(=O)CCC=O	1814.1	Standard polar	33892256
4-Oxononanal	CCCCCC(=O)CCC=O	1175.8	Standard non polar	33892256
4-Oxononanal	CCCCCC(=O)CCC=O	1238.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Oxononanal,1TMS,isomer #1	CCCCCC(=CCC=O)O[Si](C)(C)C	1434.1	Semi standard non polar	33892256
4-Oxononanal,1TMS,isomer #1	CCCCCC(=CCC=O)O[Si](C)(C)C	1434.7	Standard non polar	33892256
4-Oxononanal,1TMS,isomer #2	CCCCC=C(CCC=O)O[Si](C)(C)C	1438.6	Semi standard non polar	33892256
4-Oxononanal,1TMS,isomer #2	CCCCC=C(CCC=O)O[Si](C)(C)C	1399.8	Standard non polar	33892256
4-Oxononanal,1TMS,isomer #3	CCCCCC(=O)CC=CO[Si](C)(C)C	1454.4	Semi standard non polar	33892256
4-Oxononanal,1TMS,isomer #3	CCCCCC(=O)CC=CO[Si](C)(C)C	1391.4	Standard non polar	33892256
4-Oxononanal,2TMS,isomer #1	CCCCCC(=CC=CO[Si](C)(C)C)O[Si](C)(C)C	1653.2	Semi standard non polar	33892256
4-Oxononanal,2TMS,isomer #1	CCCCCC(=CC=CO[Si](C)(C)C)O[Si](C)(C)C	1598.9	Standard non polar	33892256
4-Oxononanal,2TMS,isomer #2	CCCCC=C(CC=CO[Si](C)(C)C)O[Si](C)(C)C	1599.8	Semi standard non polar	33892256
4-Oxononanal,2TMS,isomer #2	CCCCC=C(CC=CO[Si](C)(C)C)O[Si](C)(C)C	1582.3	Standard non polar	33892256
4-Oxononanal,1TBDMS,isomer #1	CCCCCC(=CCC=O)O[Si](C)(C)C(C)(C)C	1667.6	Semi standard non polar	33892256
4-Oxononanal,1TBDMS,isomer #1	CCCCCC(=CCC=O)O[Si](C)(C)C(C)(C)C	1637.0	Standard non polar	33892256
4-Oxononanal,1TBDMS,isomer #2	CCCCC=C(CCC=O)O[Si](C)(C)C(C)(C)C	1662.4	Semi standard non polar	33892256
4-Oxononanal,1TBDMS,isomer #2	CCCCC=C(CCC=O)O[Si](C)(C)C(C)(C)C	1598.6	Standard non polar	33892256
4-Oxononanal,1TBDMS,isomer #3	CCCCCC(=O)CC=CO[Si](C)(C)C(C)(C)C	1670.4	Semi standard non polar	33892256
4-Oxononanal,1TBDMS,isomer #3	CCCCCC(=O)CC=CO[Si](C)(C)C(C)(C)C	1608.1	Standard non polar	33892256
4-Oxononanal,2TBDMS,isomer #1	CCCCCC(=CC=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2106.8	Semi standard non polar	33892256
4-Oxononanal,2TBDMS,isomer #1	CCCCCC(=CC=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1973.4	Standard non polar	33892256
4-Oxononanal,2TBDMS,isomer #2	CCCCC=C(CC=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2040.6	Semi standard non polar	33892256
4-Oxononanal,2TBDMS,isomer #2	CCCCC=C(CC=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1979.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Oxononanal GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9000000000-1910490080180d490f91	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Oxononanal 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 - 4-Oxononanal 10V, Positive-QTOF	splash10-0a4i-1900000000-e1dedc2be1f9e0ed140a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxononanal 20V, Positive-QTOF	splash10-0a4i-9300000000-86a44f5873a5032d3e55	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxononanal 40V, Positive-QTOF	splash10-0a4l-9000000000-7267663893d3d33669a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxononanal 10V, Negative-QTOF	splash10-0a4i-1900000000-2fd1227f076d7cca08b6	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxononanal 20V, Negative-QTOF	splash10-0a4l-9800000000-7d6c71c214a93c57012d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxononanal 40V, Negative-QTOF	splash10-0006-9000000000-6ea0def9f33f3cfc4630	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxononanal 10V, Positive-QTOF	splash10-05we-9200000000-f4ff33d5fdcdcc44a6cb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxononanal 20V, Positive-QTOF	splash10-00dm-9000000000-6dd7d88c08d2c690d281	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxononanal 40V, Positive-QTOF	splash10-0006-9000000000-6517f3f5c49a41fa6272	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxononanal 10V, Negative-QTOF	splash10-03di-0900000000-b38de3f944c197cb8e25	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxononanal 20V, Negative-QTOF	splash10-08fu-9700000000-b125e5475c4c885cf456	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxononanal 40V, Negative-QTOF	splash10-052f-9000000000-bc92bc879d16efca25f9	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

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

FDB013252

KNApSAcK ID

Not Available

Chemspider ID

137628

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156288

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1128051

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 4-Oxononanal (HMDB0034716)

MOL for HMDB0034716 (4-Oxononanal)

3D MOL for HMDB0034716 (4-Oxononanal)

3D SDF for HMDB0034716 (4-Oxononanal)

3D-SDF for HMDB0034716 (4-Oxononanal)

PDB for HMDB0034716 (4-Oxononanal)

3D PDB for HMDB0034716 (4-Oxononanal)

SMILES for HMDB0034716 (4-Oxononanal)

INCHI for HMDB0034716 (4-Oxononanal)

Structure for HMDB0034716 (4-Oxononanal)

3D Structure for HMDB0034716 (4-Oxononanal)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra