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Record Information
Version4.0
Creation Date2006-10-19 10:22:39 UTC
Update Date2017-09-27 08:24:33 UTC
HMDB IDHMDB0005049
Secondary Accession Numbers
  • HMDB05049
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-dienoic acidKegg
10-NitrolinoleateGenerator
(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
9-Nitrolinoleic acidMeSH
LNO2 CPDMeSH
Nitrolinoleic acidMeSH
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 KeyLELVHAQTWXTCLY-XYWKCAQWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • Nitro fatty acid
  • Unsaturated fatty acid
  • Fatty acid
  • Organic nitro compound
  • C-nitro compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organopnictogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Role

Industrial application:

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity94.89 m³·mol⁻¹ChemAxon
Polarizability38.04 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0039000000-a0145ec33f7a3be2829dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-3973000000-91a3d8e47d9c6c518ff8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06rf-9240000000-d685c15c05ff5bdc936eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-0109000000-30e8f320a0693166640bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0600-0936000000-5a28718ffca2d1ea0d3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9320000000-6f461338a4c012622218View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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
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. [PubMed:16537525 ]