Structure Database (LMSD)

Common Name
10-Nitrolinoleic acid
Systematic Name
10-nitro-9Z,12Z-octadecadienoic acid
Synonyms
  • C10-LNO2
LM ID
LMFA01120001
Formula
C18H31NO4
Exact Mass
Calculate m/z
325.225309
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Nitro fatty acids [FA0112]
Unsaturated fatty acids [FA0103]
Octadecanoids [FA02]

Biological Context

10-Nitrolinoleate is a nitrated fatty acid and a peroxisome proliferator-activated receptor γ (PPARγ) agonist.1 It is formed from linoleic acid upon exposure to acidified nitrite.2

This information has been provided by Cayman Chemical

References

1. Woodcock, S.R., Salvatore, S.R., Bonacci, G., et al. Biomimetic nitration of conjugated linoleic acid: Formation and characterization of naturally occurring conjugated nitrodienes. The Journal of Organic Chemistry 79(1), 25-33 (2014).
2. Dunny, E., and Evans, P. Stereocontrolled synthesis of the PPAR-γ agonist 10-nitrolinoleic acid. The Journal of Organic Chemistry 75(15), 5334-5336 (2010).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Red cell membrane and plasma linoleic acid nitration products: synthesis, clinical identification, and quantitation.,
Proc Natl Acad Sci U S A, 2004
Pubmed ID: 15273286

String Representations

InChiKey (Click to copy)
LELVHAQTWXTCLY-XYWKCAQWSA-N
InChi (Click to copy)
InChI=1S/C18H31NO4/c1-2-3-4-5-8-11-14-17(19(22)23)15-12-9-6-7-10-13-16-18(20)21/h8,11,15H,2-7,9-10,12-14,16H2,1H3,(H,20,21)/b11-8-,17-15+
SMILES (Click to copy)
OC(CCCCCCC/C=C(/[N+]([O-])=O)\C/C=C\CCCCC)=O

Other Databases

KEGG ID
C13800
HMDB ID
HMDB0005049
CHEBI ID
34125
PubChem CID
5282259
Cayman ID
10037
PDB ID
LNA

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 0
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 355.56
Topological Polar Surface Area 80.44
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 5
logP 5.49
Molar Refractivity 92.93

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Created at
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Updated at
14th May 2021