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Record Information
Version3.6
Creation Date2006-10-19 10:22:39 UTC
Update Date2016-02-11 01:07:03 UTC
HMDB IDHMDB05049
Secondary Accession NumbersNone
Metabolite Identification
Common Name10-Nitrolinoleic acid
DescriptionNitrolinoleic acid is a nitrated fatty acid (or nitroalkene, a class of cell signaling mediators generated by Nitric Oxide (NO) and fatty acid-dependent redox reactions). Nitrated fatty acids such as 10- and 12-nitro-9,12-octadecadienoic acid exhibit pluripotent antiinflammatory cell signaling properties. (PMID 16537525 ).
Structure
Thumb
Synonyms
ValueSource
10-nitro-9-cis,12-cis-Octadecadienoic acidKegg
10-nitro-9-cis,12-cis-OctadecadienoateKegg
(9E,12Z)-10-Nitrooctadeca-9,12-dienoateGenerator
10-nitro-9,12-OctadecadienoateHMDB
10-nitro-9,12-Octadecadienoic acidHMDB
12-nitro-9,12-OctadecadienoateHMDB
12-nitro-9,12-Octadecadienoic acidHMDB
LNO2HMDB
Chemical FormulaC18H31NO4
Average Molecular Weight325.443
Monoisotopic Molecular Weight325.225308485
IUPAC Name(9E,12Z)-10-nitrooctadeca-9,12-dienoic acid
Traditional Name9-hode
CAS Registry Number774603-04-2
SMILES
CCCCC\C=C/C\C(=C/CCCCCCCC(O)=O)[N+]([O-])=O
InChI Identifier
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+
InChI KeyInChIKey=LELVHAQTWXTCLY-XYWKCAQWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassLineolic acids and derivatives
Sub ClassNot Available
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • Nitro fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Organic nitro compound
  • Organic nitrite
  • C-nitro compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic zwitterion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0014 mg/mLALOGPS
logP5.28ALOGPS
logP5.6ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.12 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity94.89 m3·mol-1ChemAxon
Polarizability38.04 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.079 +/- 0.035 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023611
KNApSAcK IDNot Available
Chemspider ID4445433
KEGG Compound IDC13800
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB05049
Metagene LinkHMDB05049
METLIN IDNot Available
PubChem Compound5282259
PDB IDLNA
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wright MM, Schopfer FJ, Baker PR, Vidyasagar V, Powell P, Chumley P, Iles KE, Freeman BA, Agarwal A: Fatty acid transduction of nitric oxide signaling: nitrolinoleic acid potently activates endothelial heme oxygenase 1 expression. Proc Natl Acad Sci U S A. 2006 Mar 14;103(11):4299-304. Epub 2006 Mar 6. [16537525 ]