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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 17:34:02 UTC
Update Date2017-10-23 19:04:11 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 ).
Structure
Thumb
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-alMeSH
4-HNE CPDMeSH
4-Hydroxy-2-nonenal, (e)-isomerMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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:

  Health condition:

    Gastrointestinal disorders:

    Psychiatric disorders:

    Renal and urinary disorders:

    Nervous system disorders:

  Observation:

    Investigations:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Parenteral:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Role

Indirect biological role:

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-9000000000-2b2e86f0d26bfcdbaa7cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-9800000000-f25e4e5c5bfdea54d97cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-1900000000-9e0485f40ddea525bfb2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abi-9700000000-14b48d43b52506ea875aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-c60e1ce771da41f3cef1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-963698def33862d38ed8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3900000000-39790f81d0ebc18f6f71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-a4ef5b05613d7c911528View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.11 +/- 0.06 uMAdult (>18 years old)BothNormal details
BloodExpected but not Quantified Not AvailableNot Available
Normal
    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
    UrineDetected and Quantified0.00028 +/- 0.000079 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    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
    Associated Disorders and Diseases
    Disease References
    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 ]
    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 ]
    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 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB001438
    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
    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 ]

    Enzymes

    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 ]