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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:21:28 UTC

Update Date

2021-09-26 22:53:38 UTC

HMDB ID

HMDB0245269

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-Nonenal, 4-hydroxy-, (2E,4R)-

Description

4-hydroxynon-2-enal, also known as 4-HNE, belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Based on a literature review a significant number of articles have been published on 4-hydroxynon-2-enal. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2-nonenal, 4-hydroxy-, (2e,4r)- is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2-Nonenal, 4-hydroxy-, (2E,4R)- 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

COMPND    HMDB0245269
HETATM    1  C1  UNL     1       2.834   0.513   1.280  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.851  -0.715   0.389  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.460  -1.116  -0.037  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.769  -0.021  -0.808  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.613  -0.402  -1.240  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.516  -0.728  -0.067  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.801  -1.082  -0.462  1.00  0.00           O  
HETATM    8  C7  UNL     1      -1.606   0.338   0.938  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.333   1.425   0.838  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.140   1.673  -0.320  1.00  0.00           C  
HETATM   11  O2  UNL     1      -3.823   2.732  -0.371  1.00  0.00           O  
HETATM   12  H1  UNL     1       2.001   0.423   2.014  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.796   0.585   1.828  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.732   1.455   0.701  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.520  -0.552  -0.464  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.290  -1.532   0.995  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.569  -1.983  -0.720  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.891  -1.466   0.843  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.822   0.949  -0.304  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.367   0.103  -1.759  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.575  -1.332  -1.862  1.00  0.00           H  
HETATM   22  H11 UNL     1      -1.069   0.375  -1.875  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.106  -1.634   0.486  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.737  -1.475  -1.384  1.00  0.00           H  
HETATM   25  H14 UNL     1      -1.026   0.265   1.883  1.00  0.00           H  
HETATM   26  H15 UNL     1      -2.333   2.168   1.650  1.00  0.00           H  
HETATM   27  H16 UNL     1      -3.224   1.033  -1.169  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    8   23
CONECT    7   24
CONECT    8    9    9   25
CONECT    9   10   26
CONECT   10   11   11   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-HNE	ChEBI
4-Hydroxy-2,3-nonenal	ChEBI
4-Hydroxy-2-nonenal	ChEBI
4-Hydroxynonenal	ChEBI
HNE	ChEBI
4-HNE CPD	MeSH
4-Hydroxy-2-nonenal, (e)-isomer	MeSH
4-Hydroxynonen-2-al	MeSH

Chemical Formula

C₉H₁₆O₂

Average Molecular Weight

156.225

Monoisotopic Molecular Weight

156.115029755

IUPAC Name

4-hydroxynon-2-enal

Traditional Name

4 hydroxynonenal

CAS Registry Number

Not Available

SMILES

CCCCCC(O)C=CC=O

InChI Identifier

InChI=1S/C9H16O2/c1-2-3-4-6-9(11)7-5-8-10/h5,7-9,11H,2-4,6H2,1H3

InChI Key

JVJFIQYAHPMBBX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Fatty alcohols

Alternative Parents

Substituents

Fatty alcohol
Medium-chain aldehyde
Enal
Alpha,beta-unsaturated aldehyde
Secondary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

enal (CHEBI:32585 )
hydroxyaldehyde (CHEBI:32585 )
a small molecule (CPD-10806 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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
logP	1.87	ALOGPS
logP	1.75	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	14.86	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	46.56 m³·mol⁻¹	ChemAxon
Polarizability	18.5 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]+	136.555	30932474
DeepCCS	[M-H]-	133.614	30932474
DeepCCS	[M-2H]-	170.58	30932474
DeepCCS	[M+Na]+	145.523	30932474
AllCCS	[M+H]+	138.8	32859911
AllCCS	[M+H-H2O]+	134.8	32859911
AllCCS	[M+NH4]+	142.6	32859911
AllCCS	[M+Na]+	143.7	32859911
AllCCS	[M-H]-	138.9	32859911
AllCCS	[M+Na-2H]-	140.8	32859911
AllCCS	[M+HCOO]-	143.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.7676 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.13 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1854.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	316.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	141.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	201.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	177.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	517.3 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	528.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	94.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1090.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	367.4 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	1258.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	331.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	331.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	409.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	382.4 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	13.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Nonenal, 4-hydroxy-, (2E,4R)-	CCCCCC(O)C=CC=O	2226.8	Standard polar	33892256
2-Nonenal, 4-hydroxy-, (2E,4R)-	CCCCCC(O)C=CC=O	1244.8	Standard non polar	33892256
2-Nonenal, 4-hydroxy-, (2E,4R)-	CCCCCC(O)C=CC=O	1308.9	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 - 2-Nonenal, 4-hydroxy-, (2E,4R)- GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-9000000000-2b2e86f0d26bfcdbaa7c	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Nonenal, 4-hydroxy-, (2E,4R)- GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Nonenal, 4-hydroxy-, (2E,4R)- GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Nonenal, 4-hydroxy-, (2E,4R)- GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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-Nonenal, 4-hydroxy-, (2E,4R)- 10V, Positive-QTOF	splash10-052r-1900000000-997dfee0032c5ef2b75c	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenal, 4-hydroxy-, (2E,4R)- 20V, Positive-QTOF	splash10-0abi-9700000000-290a0dc6619a8e7e5025	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenal, 4-hydroxy-, (2E,4R)- 40V, Positive-QTOF	splash10-0a4l-9000000000-5674db6df3edf2ab9b9d	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenal, 4-hydroxy-, (2E,4R)- 10V, Negative-QTOF	splash10-0a4i-1900000000-53cd5cf35c25a6123298	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenal, 4-hydroxy-, (2E,4R)- 20V, Negative-QTOF	splash10-0a4i-3900000000-c82d3554dcf75b415ef6	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenal, 4-hydroxy-, (2E,4R)- 40V, Negative-QTOF	splash10-0006-9100000000-9454ca801295202b0a1d	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenal, 4-hydroxy-, (2E,4R)- 10V, Positive-QTOF	splash10-0007-9300000000-9c3d48d2b69a51fb7d63	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenal, 4-hydroxy-, (2E,4R)- 20V, Positive-QTOF	splash10-00r6-9000000000-fdc847c35b84e0c9d894	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenal, 4-hydroxy-, (2E,4R)- 40V, Positive-QTOF	splash10-0006-9000000000-d7140511cfc2bca207a8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenal, 4-hydroxy-, (2E,4R)- 10V, Negative-QTOF	splash10-03di-0900000000-c09fa78f1a3efa8c0e31	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenal, 4-hydroxy-, (2E,4R)- 20V, Negative-QTOF	splash10-0ab9-5900000000-5f46d902d1ecb2e14a93	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Nonenal, 4-hydroxy-, (2E,4R)- 40V, Negative-QTOF	splash10-0aor-9100000000-e66e02441083fb8392a5	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

1630

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4-Hydroxynonenal

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

32585

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1491211

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-Nonenal, 4-hydroxy-, (2E,4R)- (HMDB0245269)

MOL for HMDB0245269 (2-Nonenal, 4-hydroxy-, (2E,4R)-)

3D MOL for HMDB0245269 (2-Nonenal, 4-hydroxy-, (2E,4R)-)

3D SDF for HMDB0245269 (2-Nonenal, 4-hydroxy-, (2E,4R)-)

3D-SDF for HMDB0245269 (2-Nonenal, 4-hydroxy-, (2E,4R)-)

PDB for HMDB0245269 (2-Nonenal, 4-hydroxy-, (2E,4R)-)

3D PDB for HMDB0245269 (2-Nonenal, 4-hydroxy-, (2E,4R)-)

SMILES for HMDB0245269 (2-Nonenal, 4-hydroxy-, (2E,4R)-)

INCHI for HMDB0245269 (2-Nonenal, 4-hydroxy-, (2E,4R)-)

Structure for HMDB0245269 (2-Nonenal, 4-hydroxy-, (2E,4R)-)

3D Structure for HMDB0245269 (2-Nonenal, 4-hydroxy-, (2E,4R)-)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra