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Showing metabocard for 4-Hydroxynonenal (HMDB0004362)

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enzymes (1) Show 1 protein
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 17:34:02 UTC
Update Date2023-02-21 17:17:00 UTC
HMDB IDHMDB0004362
Secondary Accession Numbers
  • HMDB04362
Metabolite Identification
Common Name4-Hydroxynonenal
Description4-Hydroxynonenal (HNE), one of the major end products of lipid peroxidation, has been shown to be involved in signal transduction and available evidence suggests that it can affect cell cycle events in a concentration-dependent manner. glutathione S-transferases (GSTs) can modulate the intracellular concentrations of HNE by affecting its generation during lipid peroxidation by reducing hydroperoxides and also by converting it into a glutathione conjugate. Overexpression of the Alpha class GSTs in cells leads to lower steady-state levels of HNE, and these cells acquire resistance to apoptosis induced by lipid peroxidation-causing agents such as H(2)O(2), UVA, superoxide anion, and pro-oxidant xenobiotics, suggesting that signaling for apoptosis by these agents is transduced through HNE. Cells with the capacity to exclude HNE from the intracellular environment at a faster rate are relatively more resistant to apoptosis caused by H(2)O(2), UVA, superoxide anion, and pro-oxidant xenobiotics as well as by HNE, suggesting that HNE may be a common denominator in mechanisms of apoptosis caused by oxidative stress. Transfection of adherent cells with HNE-metabolizing GSTs leads to transformation of these cells due to depletion of HNE. (PMID 15288119 ). HNE has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).
Structure
Data?1676999820
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0004362 (4-Hydroxynonenal)


  Mrv0541 02231219562D          

 11 10  0  0  0  0            999 V2000
   14.2567  -10.6475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1131  -12.7102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6858  -11.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9713  -11.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4004  -11.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2567  -11.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1148  -11.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8293  -11.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5422  -11.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8277  -11.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1131  -11.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2 11  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0004362 (4-Hydroxynonenal)

HMDB0004362
     RDKit          3D
4-Hydroxynonenal
 27 26  0  0  0  0  0  0  0  0999 V2000
   -3.6371    0.2426    0.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4356   -0.2530   -0.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1473    0.2867   -1.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144   -0.1888   -0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3293    0.3027   -0.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3795   -0.2174    0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3843   -1.6130    0.2509 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507    0.2077   -0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7477   -0.0131    0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1191    0.3792    0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0562    0.1635    1.1433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6838    0.6557    0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9783    1.0913    1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5021   -0.5702    1.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3088   -0.0441   -1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3430   -1.3626   -0.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0245    0.0384   -2.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1795    1.4117   -1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9752   -1.2961   -0.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1975    0.1541    0.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3532    1.4129   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4939   -0.0881   -1.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1597    0.1409    1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7426   -1.8949    0.9563 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9864    0.6846   -1.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5566   -0.4911    1.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3681    0.8603   -0.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
M  END
Download

3D SDF for HMDB0004362 (4-Hydroxynonenal)


  Mrv0541 02231219562D          

 11 10  0  0  0  0            999 V2000
   14.2567  -10.6475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1131  -12.7102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6858  -11.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9713  -11.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4004  -11.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2567  -11.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1148  -11.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8293  -11.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5422  -11.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8277  -11.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1131  -11.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2 11  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004362

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC(O)\C=C\C=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/b7-5+

> <INCHI_KEY>
JVJFIQYAHPMBBX-FNORWQNLSA-N

> <FORMULA>
C9H16O2

> <MOLECULAR_WEIGHT>
156.2221

> <EXACT_MASS>
156.115029756

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
18.707275407887074

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-4-hydroxynon-2-enal

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.7529982929999997

> <ALOGPS_LOGS>
-1.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.8565322575265

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8615527905579086

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
46.56

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trans-4-hydroxy-2-nonenal

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0004362 (4-Hydroxynonenal)

HMDB0004362
     RDKit          3D
4-Hydroxynonenal
 27 26  0  0  0  0  0  0  0  0999 V2000
   -3.6371    0.2426    0.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4356   -0.2530   -0.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1473    0.2867   -1.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144   -0.1888   -0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3293    0.3027   -0.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3795   -0.2174    0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3843   -1.6130    0.2509 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507    0.2077   -0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7477   -0.0131    0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1191    0.3792    0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0562    0.1635    1.1433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6838    0.6557    0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9783    1.0913    1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5021   -0.5702    1.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3088   -0.0441   -1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3430   -1.3626   -0.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0245    0.0384   -2.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1795    1.4117   -1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9752   -1.2961   -0.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1975    0.1541    0.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3532    1.4129   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4939   -0.0881   -1.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1597    0.1409    1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7426   -1.8949    0.9563 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9864    0.6846   -1.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5566   -0.4911    1.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3681    0.8603   -0.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
M  END
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PDB for HMDB0004362 (4-Hydroxynonenal)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      26.612 -19.875   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      22.611 -23.726   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      29.280 -21.416   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.946 -22.186   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.614 -22.186   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.612 -21.416   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.948 -21.416   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.281 -22.186   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.279 -22.186   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.945 -21.416   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.611 -22.186   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2   11                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    1    4    9                                                  
CONECT    7    5    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11                                                       
CONECT   11    2   10                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for HMDB0004362 (4-Hydroxynonenal)

COMPND    HMDB0004362
HETATM    1  C1  UNL     1      -3.637   0.243   0.888  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.436  -0.253  -0.514  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.147   0.287  -1.091  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.014  -0.189  -0.215  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.329   0.303  -0.713  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.379  -0.217   0.214  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.384  -1.613   0.251  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.751   0.208  -0.182  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.748  -0.013   0.660  1.00  0.00           C  
HETATM   10  C9  UNL     1       5.119   0.379   0.335  1.00  0.00           C  
HETATM   11  O2  UNL     1       6.056   0.164   1.143  1.00  0.00           O  
HETATM   12  H1  UNL     1      -4.684   0.656   0.948  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.978   1.091   1.159  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.502  -0.570   1.632  1.00  0.00           H  
HETATM   15  H4  UNL     1      -4.309  -0.044  -1.167  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.343  -1.363  -0.483  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.025   0.038  -2.142  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.179   1.412  -1.020  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.975  -1.296  -0.202  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.198   0.154   0.818  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.353   1.413  -0.681  1.00  0.00           H  
HETATM   22  H11 UNL     1       0.494  -0.088  -1.741  1.00  0.00           H  
HETATM   23  H12 UNL     1       1.160   0.141   1.244  1.00  0.00           H  
HETATM   24  H13 UNL     1       0.743  -1.895   0.956  1.00  0.00           H  
HETATM   25  H14 UNL     1       2.986   0.685  -1.110  1.00  0.00           H  
HETATM   26  H15 UNL     1       3.557  -0.491   1.608  1.00  0.00           H  
HETATM   27  H16 UNL     1       5.368   0.860  -0.598  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
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SMILES for HMDB0004362 (4-Hydroxynonenal)

CCCCCC(O)\C=C\C=O
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INCHI for HMDB0004362 (4-Hydroxynonenal)

InChI=1S/C9H16O2/c1-2-3-4-6-9(11)7-5-8-10/h5,7-9,11H,2-4,6H2,1H3/b7-5+
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(e)-4-Hydroxy-2-nonenalChEBI
4-Hydroxy-2,3-trans-nonenalChEBI
HNEChEBI
trans-4-Hydroxy-2-nonenalChEBI
4-Hydroxy-2,3-nonenalHMDB
4-Hydroxy-2-nonenalHMDB
4-Hydroxynon-2-enalHMDB
4-Hydroxynonen-2-alHMDB
4-HNE CPDHMDB
4-Hydroxy-2-nonenal, (e)-isomerHMDB
4-HydroxynonenalChEBI
Chemical FormulaC9H16O2
Average Molecular Weight156.2221
Monoisotopic Molecular Weight156.115029756
IUPAC Name(2E)-4-hydroxynon-2-enal
Traditional Nametrans-4-hydroxy-2-nonenal
CAS Registry Number75899-68-2
SMILES
CCCCCC(O)\C=C\C=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/b7-5+
InChI KeyJVJFIQYAHPMBBX-FNORWQNLSA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentFatty 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.08 g/LALOGPS
logP1.87ALOGPS
logP1.75ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)14.86ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity46.56 m³·mol⁻¹ChemAxon
Polarizability18.71 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.5131661259
DarkChem[M-H]-136.1631661259
DeepCCS[M+H]+140.82330932474
DeepCCS[M-H]-137.75530932474
DeepCCS[M-2H]-175.20230932474
DeepCCS[M+Na]+150.21730932474
AllCCS[M+H]+138.832859911
AllCCS[M+H-H2O]+134.832859911
AllCCS[M+NH4]+142.632859911
AllCCS[M+Na]+143.732859911
AllCCS[M-H]-138.932859911
AllCCS[M+Na-2H]-140.832859911
AllCCS[M+HCOO]-143.032859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.4.86 minutes32390414
Predicted by Siyang on May 30, 202211.7676 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.13 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid27.0 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1854.9 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid316.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid141.6 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid201.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid177.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid517.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid528.4 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)94.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1090.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid367.4 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1258.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid331.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid331.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate409.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA382.4 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water13.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-HydroxynonenalCCCCCC(O)\C=C\C=O2226.8Standard polar33892256
4-HydroxynonenalCCCCCC(O)\C=C\C=O1244.8Standard non polar33892256
4-HydroxynonenalCCCCCC(O)\C=C\C=O1308.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxynonenal,1TMS,isomer #1CCCCCC(/C=C/C=O)O[Si](C)(C)C1432.5Semi standard non polar33892256
4-Hydroxynonenal,1TBDMS,isomer #1CCCCCC(/C=C/C=O)O[Si](C)(C)C(C)(C)C1668.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxynonenal GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-9000000000-2b2e86f0d26bfcdbaa7c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxynonenal GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-9800000000-f25e4e5c5bfdea54d97c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxynonenal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxynonenal 10V, Positive-QTOFsplash10-052r-1900000000-9e0485f40ddea525bfb22016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxynonenal 20V, Positive-QTOFsplash10-0abi-9700000000-14b48d43b52506ea875a2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxynonenal 40V, Positive-QTOFsplash10-0a4l-9000000000-c60e1ce771da41f3cef12016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxynonenal 10V, Negative-QTOFsplash10-0a4i-1900000000-963698def33862d38ed82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxynonenal 20V, Negative-QTOFsplash10-0a4i-3900000000-39790f81d0ebc18f6f712016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxynonenal 40V, Negative-QTOFsplash10-0006-9100000000-a4ef5b05613d7c9115282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxynonenal 10V, Negative-QTOFsplash10-03di-0900000000-c09fa78f1a3efa8c0e312021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxynonenal 20V, Negative-QTOFsplash10-0ab9-5900000000-5f46d902d1ecb2e14a932021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxynonenal 40V, Negative-QTOFsplash10-0aor-9100000000-e66e02441083fb8392a52021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxynonenal 10V, Positive-QTOFsplash10-0007-9300000000-9c3d48d2b69a51fb7d632021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxynonenal 20V, Positive-QTOFsplash10-00r6-9000000000-fdc847c35b84e0c9d8942021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxynonenal 40V, Positive-QTOFsplash10-0006-9000000000-d7140511cfc2bca207a82021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
BloodDetected and Quantified0.11 +/- 0.06 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.38 (0.24-0.52) uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified1.3 +/- 0.2 uMElderly (>65 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.00028 +/- 0.000079 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2650.0 +/- 140.0 uMAdult (>18 years old)BothPeripheral arterial disease details
BloodDetected and Quantified0.75 +/- 0.31 uMAdult (>18 years old)Bothuremia details
Cerebrospinal Fluid (CSF)Detected and Quantified1.47 (0.71-2.23) uMAdult (>18 years old)Not SpecifiedParkinson's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.40 +/- 0.030 uMAdult (>18 years old)Not SpecifiedAlzheimer's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.36 +/- 0.03 uMAdult (>18 years old)BothAlzheimer's disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
Associated Disorders and Diseases
Disease References
Peripheral vascular disease
  1. Signorelli SS, Fatuzzo P, Rapisarda F, Neri S, Ferrante M, Oliveri Conti G, Fallico R, Di Pino L, Pennisi G, Celotta G, Massimiliano A: A randomised, controlled clinical trial evaluating changes in therapeutic efficacy and oxidative parameters after treatment with propionyl L-carnitine in patients with peripheral arterial disease requiring haemodialysis. Drugs Aging. 2006;23(3):263-70. [PubMed:16608381 ]
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Parkinson's disease
  1. Selley ML: (E)-4-hydroxy-2-nonenal may be involved in the pathogenesis of Parkinson's disease. Free Radic Biol Med. 1998 Jul 15;25(2):169-74. [PubMed:9667492 ]
Alzheimer's disease
  1. Selley ML, Close DR, Stern SE: The effect of increased concentrations of homocysteine on the concentration of (E)-4-hydroxy-2-nonenal in the plasma and cerebrospinal fluid of patients with Alzheimer's disease. Neurobiol Aging. 2002 May-Jun;23(3):383-8. [PubMed:11959400 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB020986
KNApSAcK IDC00000447
Chemspider ID4446465
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Hydroxynonenal
METLIN IDNot Available
PubChem Compound5283344
PDB IDNot Available
ChEBI ID58968
Food Biomarker OntologyNot Available
VMH IDCE2006
MarkerDB IDMDB00000448
Good Scents IDNot Available
References
Synthesis ReferenceEsterbauer, Hermann; Benedetti, Angelo; Lang, Johanna; Fulceri, Rosella; Fauler, Gunther; Comporti, Mario. Studies on the mechanism of formation of 4-hydroxynonenal during microsomal lipid peroxidation. Biochimica et Biophysica Acta, Lipids and Lipid Metabolism (1986), 876(1), 154-66.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Awasthi YC, Yang Y, Tiwari NK, Patrick B, Sharma A, Li J, Awasthi S: Regulation of 4-hydroxynonenal-mediated signaling by glutathione S-transferases. Free Radic Biol Med. 2004 Sep 1;37(5):607-19. [PubMed:15288119 ]
  2. Selley ML, Close DR, Stern SE: The effect of increased concentrations of homocysteine on the concentration of (E)-4-hydroxy-2-nonenal in the plasma and cerebrospinal fluid of patients with Alzheimer's disease. Neurobiol Aging. 2002 May-Jun;23(3):383-8. [PubMed:11959400 ]
  3. Selley ML: (E)-4-hydroxy-2-nonenal may be involved in the pathogenesis of Parkinson's disease. Free Radic Biol Med. 1998 Jul 15;25(2):169-74. [PubMed:9667492 ]
  4. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]

Enzymes

Enzyme Details
1. Glutathione S-transferase A4
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. This isozyme has a high catalytic efficiency with 4-hydroxyalkenals such as 4-hydroxynonenal (4-HNE).
Gene Name:
GSTA4
Uniprot ID:
O15217
Molecular weight:
25703.905
References
  1. Awasthi YC, Yang Y, Tiwari NK, Patrick B, Sharma A, Li J, Awasthi S: Regulation of 4-hydroxynonenal-mediated signaling by glutathione S-transferases. Free Radic Biol Med. 2004 Sep 1;37(5):607-19. [PubMed:15288119 ]