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9-Nitrooleate

CAT: 0931-T36830-02Size: 100 µgDry Ice: NoHazardous: No
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CAT#:0931-T36830-02Size:100 µg
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CAS Number
875685-44-2
Target
Others, PPAR
Related Pathways
Others, Metabolism, DNA Damage/DNA Repair
Bioactivity
Nitrated unsaturated fatty acids, such as 10- and 12-nitrolinoleate , 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. 9-Nitrooleate is one of two regioisomers of nitrooleate, the other being 10-nitrooleate (OA-NO2; used for the mixture of isomers), which are formed by nitration of oleic acid in approximately equal proportions in vivo. 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.
Smiles
CCCCCCCC\C=C(/CCCCCCCC(O)=O)N(=O)=O
Molecular Formula
C18H33NO4
Molecular Weight
327.465
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

9-Nitrooleic acid

(9E)-9-nitrooctadecenoic acid is a nitro fatty acid that is (9E)-octadec-9-enoic (elaidic) acid substituted by a nitro group at position 9. It has a role as a human metabolite. It is a long-chain fatty acid, a monounsaturated fatty acid and a nitro fatty acid. It is functionally related to an elaidic acid.

CAS Number875685-44-2
PubChem CID11645581
IUPAC Name(E)-9-nitrooctadec-9-enoic acid
Molecular FormulaC18H33NO4
Molecular Weight327.5
XLogP6.7
Topological Polar Surface Area83.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count15
Heavy Atom Count23
Formal Charge0
Complexity347
SMILES
CCCCCCCC/C=C(\CCCCCCCC(=O)O)/[N+](=O)[O-]
InChI
InChI=1S/C18H33NO4/c1-2-3-4-5-6-8-11-14-17(19(22)23)15-12-9-7-10-13-16-18(20)21/h14H,2-13,15-16H2,1H3,(H,20,21)/b17-14+
InChIKey
CQOAKBVRRVHWKV-SAPNQHFASA-N
Chemical Structure
2D Structure
2D structure of 9-Nitrooleic acid
CAS: 875685-44-2
CID: 11645581
Formula: C18H33NO4
MW: 327.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight327.5
XLogP36.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count15
Exact Mass327.24095853
Monoisotopic Mass327.24095853
Topological Polar Surface Area83.1 Ų
Heavy Atom Count23
Formal Charge0
Complexity347
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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