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Showing NP-Card for 4-Hydroxy-2E-nonenal (NP0045559)

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Record Information
Version2.0
Created at2022-03-17 19:31:50 UTC
Updated at2022-03-17 19:31:50 UTC
NP-MRD IDNP0045559
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Hydroxy-2E-nonenal
Description4-Hydroxynonenal, also known as 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. Thus, 4-hydroxynonenal is considered to be a fatty aldehyde lipid molecule. 4-Hydroxynonenal is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 4-Hydroxynonenal has been detected, but not quantified in, several different foods, such as acerola, oriental wheats, giant butterburs, cupuaçus, and squashberries. This could make 4-hydroxynonenal a potential biomarker for the consumption of these foods. 4-Hydroxynonenal is a potentially toxic compound. 4-Hydroxy-2E-nonenal was first documented in 1998 (PMID: 9667492). The E (trans) stereoisomer of 4-hydroxynon-2-enal; it is the primary alpha,beta-unsaturated hydroxyalkenal produced by lipid peroxidation in cells (PMID: 11959400) (PMID: 26800898) (PMID: 15288119) (PMID: 16603628) (PMID: 17189262).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0045559 (4-Hydroxy-2E-nonenal)


  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
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3D MOL for NP0045559 (4-Hydroxy-2E-nonenal)

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3D SDF for NP0045559 (4-Hydroxy-2E-nonenal)

  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>
NP0045559

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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3D-SDF for NP0045559 (4-Hydroxy-2E-nonenal)
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PDB for NP0045559 (4-Hydroxy-2E-nonenal)
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 NP0045559 (4-Hydroxy-2E-nonenal)
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SMILES for NP0045559 (4-Hydroxy-2E-nonenal)
CCCCCC(O)\C=C\C=O
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INCHI for NP0045559 (4-Hydroxy-2E-nonenal)
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 JSmol
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 Mass156.2221 Da
Monoisotopic Mass156.11503 Da
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Vicia fabaFooDB
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0004362  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
General References
  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  ] 
  2. Khan F, Moinuddin, Mir AR, Islam S, Alam K, Ali A: Immunochemical studies on HNE-modified HSA: Anti-HNE-HSA antibodies as a probe for HNE damaged albumin in SLE. Int J Biol Macromol. 2016 May;86:145-54. doi: 10.1016/j.ijbiomac.2016.01.053. Epub 2016 Jan 19. [PubMed:26800898  ] 
  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. doi: 10.1016/s0891-5849(98)00021-5. [PubMed:9667492  ] 
  4. 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. doi: 10.1016/j.freeradbiomed.2004.05.033. [PubMed:15288119  ] 
  5. Akagawa M, Ito S, Toyoda K, Ishii Y, Tatsuda E, Shibata T, Yamaguchi S, Kawai Y, Ishino K, Kishi Y, Adachi T, Tsubata T, Takasaki Y, Hattori N, Matsuda T, Uchida K: Bispecific abs against modified protein and DNA with oxidized lipids. Proc Natl Acad Sci U S A. 2006 Apr 18;103(16):6160-5. doi: 10.1073/pnas.0600865103. Epub 2006 Apr 7. [PubMed:16603628  ] 
  6. Qin Z, Hu D, Han S, Reaney SH, Di Monte DA, Fink AL: Effect of 4-hydroxy-2-nonenal modification on alpha-synuclein aggregation. J Biol Chem. 2007 Feb 23;282(8):5862-70. doi: 10.1074/jbc.M608126200. Epub 2006 Dec 21. [PubMed:17189262  ]