Structure Database (LMSD)

Common Name
10-nitro-9E-octadecenoic acid
Systematic Name
10-nitro-9E-octadecenoic acid
Synonyms
LM ID
LMFA01120003
Formula
Exact Mass
Calculate m/z
327.240959
Status
Curated

Classification

Biological Context

Nitrated unsaturated fatty acids, such as 10- and 12-nitrolinoleate (LNO2), cholesteryl nitrolinoleate, and nitrohydroxylinoleate, represent a new class of endogenous lipid-derived signalling molecules. LNO2 isomers serve as potent endogenous ligands for PPARγ and can also decompose or be metabolized to release nitric oxide.1,2,3,4 10-Nitrooleate is one of two regioisomers of nitrooleate, the other being 9-nitrooleate (OA-NO2; used for the mixture of isomers), which are formed by nitration of oleic acid in approximately equal proportions in vivo.5 Peroxynitrite, acidified nitrite, and myeloperoxidase in the presence of H2O2 and nitrite, all mediate the nitration of oleic acid. OA-NO2 is found in human plasma as the free acid and esterified in phospholipids at concentrations of 619 ± 52 nM and 302 ± 369 nM, respectively. OA-NO2 activates PPARγ approximately 7-fold at a concentration of 1 µM and effectively promotes differentiation 3T3-L1 preadipocytes to adipocytes at 3 µM.5

This information has been provided by Cayman Chemical

References

5. Baker, P.R., Lin, Y., Schopfer, F.J., et al. Fatty acid transduction of nitric oxide signaling. Multiple nitrated unsaturated acid derivatives exist in human blood and urine serve as endogenous peroxisome proliferator-activated receptor ligands. The Journal of Biological Chemisty 280(51), 42464-42475 (2005).

String Representations

InChiKey (Click to copy)
WRADPCFZZWXOTI-BMRADRMJSA-N
InChi (Click to copy)
InChI=1S/C18H33NO4/c1-2-3-4-5-8-11-14-17(19(22)23)15-12-9-6-7-10-13-16-18(20)21/h15H,2-14,16H2,1H3,(H,20,21)/b17-15+
SMILES (Click to copy)
C(CCCCCCC/C=C(/[N+]([O-])=O)\CCCCCCCC)(=O)O

Other Databases

HMDB ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 0
Aromatic Rings 0
Rotatable Bonds 16
Van der Waals Molecular Volume 358.20
Topological Polar Surface Area 80.44
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 5
logP 5.71
Molar Refractivity 93.03

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Updated at
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