Structure Database (LMSD)

Common Name
4-hydroxynonenal
Systematic Name
4-hydroxy-2E-nonenal
Synonyms
  • 4-HNE
LM ID
LMFA06000051
Formula
C9H16O2
Exact Mass
Calculate m/z
156.11503
Sum Composition
FAL 9:1;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty aldehydes [FA06]

Biological Context

4-hydroxy Nonenal is a lipid peroxidation product derived from oxidized ω-6 polyunsaturated fatty acids such as arachidonic acid.1,2 4-hydroxy Nonenal is widely used as a marker of lipid peroxidation.2 It exhibits various biological activities such as cytotoxicity, growth inhibiting activity, genotoxicity, and chemotactic activity.1,2,3 4-hydroxy Nonenal inhibits pro-oxidant-induced Ca2+ release from mitochondria at 10-50 µM.2

This information has been provided by Cayman Chemical

References

3. Sodum, R.S., and Chung, F.L. 1,N2-ethenodeoxyguanosine as a potential marker for DNA adduct formation by trans-4-hydroxy-2-nonenal. Cancer Res. 48(2), 320-323 (1988).
1. Pryor, W.A., and Porter, N.A. Suggested mechanisms for the production of 4-hydroxy-2-nonenal from the autoxidation of polyunsaturated fatty acids. Free Radic. Biol. Med. 8(6), 541-543 (1990).
2. Esterbauer, H., Schaur, R.J., and Zoliner, H. Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde, and related aldehydes. Free Radic. Biol. Med. 11(1), 81-128 (1991).

String Representations

InChiKey (Click to copy)
JVJFIQYAHPMBBX-FNORWQNLSA-N
InChi (Click to copy)
InChI=1S/C9H16O2/c1-2-3-4-6-9(11)7-5-8-10/h5,7-9,11H,2-4,6H2,1H3/b7-5+
SMILES (Click to copy)
C(CCCC(O)/C=C/C([H])=O)C

Other Databases

Wikipedia
4-Hydroxynonenal
HMDB ID
HMDB0004362
CHEBI ID
58968
PubChem CID
5283344
Cayman ID
32100
GuidePharm ID
6274

Calculated Physicochemical Properties

Heavy Atoms 11
Rings 0
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 176.56
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 1.97
Molar Refractivity 45.86

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Updated at
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