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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-09 21:16:06 UTC

Update Date

2023-02-21 17:29:49 UTC

HMDB ID

HMDB0060287

Secondary Accession Numbers

HMDB60287

Metabolite Identification

Common Name

4-Hydroperoxy-2-nonenal

Description

4-Hydroperoxy-2-nonenal 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. Thus, 4-hydroperoxy-2-nonenal is considered to be a fatty aldehyde lipid molecule. 4-Hydroperoxy-2-nonenal is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

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

HEADER    PROTEIN                                 09-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.850   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.470   6.668   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.620   5.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.930   6.668   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.240   8.002   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.160   5.335   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.470   9.336   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       6.160   2.667   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.930   4.001   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    6                                                       
CONECT    5    7    8                                                       
CONECT    6    4    9                                                       
CONECT    7    5    9                                                       
CONECT    8    5   10                                                       
CONECT    9    6    7   12                                                  
CONECT   10    8                                                            
CONECT   11   12                                                            
CONECT   12    9   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

COMPND    HMDB0060287
HETATM    1  C1  UNL     1      -3.769   0.241   0.801  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.463  -0.555  -0.443  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.091  -0.216  -0.983  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.997  -0.505   0.006  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.318  -0.138  -0.618  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.485  -0.405   0.331  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.764  -0.028  -0.326  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.396   1.116  -0.029  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.645   1.475  -0.676  1.00  0.00           C  
HETATM   10  O1  UNL     1       5.209   0.761  -1.537  1.00  0.00           O  
HETATM   11  O2  UNL     1       1.314   0.215   1.549  1.00  0.00           O  
HETATM   12  O3  UNL     1       1.238  -0.645   2.547  1.00  0.00           O  
HETATM   13  H1  UNL     1      -3.038   1.053   0.865  1.00  0.00           H  
HETATM   14  H2  UNL     1      -4.809   0.650   0.785  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.731  -0.437   1.702  1.00  0.00           H  
HETATM   16  H4  UNL     1      -3.541  -1.645  -0.264  1.00  0.00           H  
HETATM   17  H5  UNL     1      -4.206  -0.259  -1.213  1.00  0.00           H  
HETATM   18  H6  UNL     1      -1.939  -0.827  -1.892  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.107   0.852  -1.282  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.149   0.059   0.941  1.00  0.00           H  
HETATM   21  H9  UNL     1      -1.025  -1.578   0.262  1.00  0.00           H  
HETATM   22  H10 UNL     1       0.351   0.947  -0.841  1.00  0.00           H  
HETATM   23  H11 UNL     1       0.520  -0.676  -1.543  1.00  0.00           H  
HETATM   24  H12 UNL     1       1.513  -1.515   0.531  1.00  0.00           H  
HETATM   25  H13 UNL     1       3.227  -0.665  -1.066  1.00  0.00           H  
HETATM   26  H14 UNL     1       2.911   1.728   0.711  1.00  0.00           H  
HETATM   27  H15 UNL     1       5.118   2.405  -0.406  1.00  0.00           H  
HETATM   28  H16 UNL     1       1.854  -1.407   2.414  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4   18   19
CONECT    4    5   20   21
CONECT    5    6   22   23
CONECT    6    7   11   24
CONECT    7    8    8   25
CONECT    8    9   26
CONECT    9   10   10   27
CONECT   11   12
CONECT   12   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Hydroxyperoxy-trans-2-nonenal	HMDB

Chemical Formula

C₉H₁₆O₃

Average Molecular Weight

172.2215

Monoisotopic Molecular Weight

172.109944378

IUPAC Name

(2E)-4-hydroperoxynon-2-enal

Traditional Name

(2E)-4-hydroperoxynon-2-enal

CAS Registry Number

Not Available

SMILES

CCCCCC(OO)\C=C\C=O

InChI Identifier

InChI=1S/C9H16O3/c1-2-3-4-6-9(12-11)7-5-8-10/h5,7-9,11H,2-4,6H2,1H3/b7-5+

InChI Key

TVNYLRYVAZWBEH-FNORWQNLSA-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
Allylic hydroperoxide
Enal
Alpha,beta-unsaturated aldehyde
Hydroperoxide
Alkyl hydroperoxide
Peroxol
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Fatty aldehydes (LMFA06000253 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0060287)

Source

Exogenous

Exogenous (HMDB: HMDB0060287)

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	2.18 g/L	ALOGPS
logP	1.91	ALOGPS
logP	2.2	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	11.71	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	47.91 m³·mol⁻¹	ChemAxon
Polarizability	19.52 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	143.559	31661259
DarkChem	[M-H]-	141.079	31661259
DeepCCS	[M+H]+	141.234	30932474
DeepCCS	[M-H]-	138.019	30932474
DeepCCS	[M-2H]-	175.613	30932474
DeepCCS	[M+Na]+	150.719	30932474
AllCCS	[M+H]+	142.7	32859911
AllCCS	[M+H-H2O]+	138.8	32859911
AllCCS	[M+NH4]+	146.4	32859911
AllCCS	[M+Na]+	147.5	32859911
AllCCS	[M-H]-	141.6	32859911
AllCCS	[M+Na-2H]-	143.2	32859911
AllCCS	[M+HCOO]-	145.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroperoxy-2-nonenal	CCCCCC(OO)\C=C\C=O	2431.4	Standard polar	33892256
4-Hydroperoxy-2-nonenal	CCCCCC(OO)\C=C\C=O	1310.9	Standard non polar	33892256
4-Hydroperoxy-2-nonenal	CCCCCC(OO)\C=C\C=O	1381.2	Semi 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-Hydroperoxy-2-nonenal GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-6900000000-c9402f289b5f4bad794b	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroperoxy-2-nonenal 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-Hydroperoxy-2-nonenal 10V, Positive-QTOF	splash10-00di-0900000000-5a43df684b29e2f408ef	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 20V, Positive-QTOF	splash10-0ab9-9700000000-29995493f38834cf5ef2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 40V, Positive-QTOF	splash10-0a4l-9000000000-62b7d7120cfa223d614f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 10V, Negative-QTOF	splash10-00di-1900000000-bdc2ca77ce700e7c97a6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 20V, Negative-QTOF	splash10-00di-3900000000-2e68a262c61bbd134019	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 40V, Negative-QTOF	splash10-0006-9200000000-bd6fe6d216c0f47210f7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 10V, Positive-QTOF	splash10-05fu-9300000000-f69c1cfbffe3ccd2fc2f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 20V, Positive-QTOF	splash10-0a4i-9000000000-2d20026b54da8a35bddb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 40V, Positive-QTOF	splash10-0a4u-9000000000-9826012832cebf72b697	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 10V, Negative-QTOF	splash10-00fr-1900000000-03fb0e183eba59f939cc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 20V, Negative-QTOF	splash10-05n3-3900000000-387e37aaabf071c724f3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 40V, Negative-QTOF	splash10-07c7-9100000000-a203720b38bc6bde126a	2021-10-12	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+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 (predicted from logP)

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

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

6435432

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

Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]

Showing metabocard for 4-Hydroperoxy-2-nonenal (HMDB0060287)

MOL for HMDB0060287 (4-Hydroperoxy-2-nonenal)

3D MOL for HMDB0060287 (4-Hydroperoxy-2-nonenal)

3D SDF for HMDB0060287 (4-Hydroperoxy-2-nonenal)

3D-SDF for HMDB0060287 (4-Hydroperoxy-2-nonenal)

PDB for HMDB0060287 (4-Hydroperoxy-2-nonenal)

3D PDB for HMDB0060287 (4-Hydroperoxy-2-nonenal)

SMILES for HMDB0060287 (4-Hydroperoxy-2-nonenal)

INCHI for HMDB0060287 (4-Hydroperoxy-2-nonenal)

Structure for HMDB0060287 (4-Hydroperoxy-2-nonenal)

3D Structure for HMDB0060287 (4-Hydroperoxy-2-nonenal)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra