Structure Database (LMSD)
Common Name
10-nitro-9E-octadecenoic acid
Systematic Name
10-nitro-9E-octadecenoic acid
Synonyms
3D model of 10-nitro-9E-octadecenoic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
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
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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Created at
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Updated at
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