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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-10-19 10:22:39 UTC
Update Date2022-03-07 02:49:25 UTC
HMDB IDHMDB0005049
Secondary Accession Numbers
  • HMDB05049
Metabolite Identification
Common Name10-Nitrolinoleic acid
Description10-Nitrolinoleic acid, also known as 10-nitrolinoleate or LNO2, 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. Based on a literature review a significant number of articles have been published on 10-Nitrolinoleic acid.
Structure
Data?1582752343
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
(9E,12Z)-10-Nitrooctadeca-9,12-dienoateGenerator
10-NitrolinoleateGenerator
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 acidHMDB
LNO2 CPDHMDB
Nitrolinoleic acidHMDB
10-Nitro,9Z,12Z-octadecadienoateHMDB
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
Description 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
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0014 g/LALOGPS
logP5.28ALOGPS
logP5.6ChemAxon
logS-5.4ALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+187.08931661259
DarkChem[M-H]-188.69631661259
DeepCCS[M+H]+187.82330932474
DeepCCS[M-H]-184.11930932474
DeepCCS[M-2H]-220.34730932474
DeepCCS[M+Na]+196.63830932474
AllCCS[M+H]+187.032859911
AllCCS[M+H-H2O]+184.232859911
AllCCS[M+NH4]+189.632859911
AllCCS[M+Na]+190.432859911
AllCCS[M-H]-185.832859911
AllCCS[M+Na-2H]-187.432859911
AllCCS[M+HCOO]-189.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
10-Nitrolinoleic acidCCCCC\C=C/C\C(=C/CCCCCCCC(O)=O)[N+]([O-])=O4024.4Standard polar33892256
10-Nitrolinoleic acidCCCCC\C=C/C\C(=C/CCCCCCCC(O)=O)[N+]([O-])=O2374.9Standard non polar33892256
10-Nitrolinoleic acidCCCCC\C=C/C\C(=C/CCCCCCCC(O)=O)[N+]([O-])=O2561.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
10-Nitrolinoleic acid,1TMS,isomer #1CCCCC/C=C\C/C(=C\CCCCCCCC(=O)O[Si](C)(C)C)[N+](=O)[O-]2580.9Semi standard non polar33892256
10-Nitrolinoleic acid,1TBDMS,isomer #1CCCCC/C=C\C/C(=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)[N+](=O)[O-]2827.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 10-Nitrolinoleic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7590000000-15b51f04c1a46072a0592017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 10-Nitrolinoleic acid GC-MS (1 TMS) - 70eV, Positivesplash10-077r-9646000000-20378331671847790b1b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 10-Nitrolinoleic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 10-Nitrolinoleic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-Nitrolinoleic acid 10V, Positive-QTOFsplash10-0a4i-0039000000-a0145ec33f7a3be2829d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-Nitrolinoleic acid 20V, Positive-QTOFsplash10-066r-3973000000-91a3d8e47d9c6c518ff82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-Nitrolinoleic acid 40V, Positive-QTOFsplash10-06rf-9240000000-d685c15c05ff5bdc936e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-Nitrolinoleic acid 10V, Negative-QTOFsplash10-05fr-0109000000-30e8f320a0693166640b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-Nitrolinoleic acid 20V, Negative-QTOFsplash10-0600-0936000000-5a28718ffca2d1ea0d3d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-Nitrolinoleic acid 40V, Negative-QTOFsplash10-0a4i-9320000000-6f461338a4c0126222182017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-Nitrolinoleic acid 10V, Negative-QTOFsplash10-00dj-3009000000-e77f8aad60e2394da5b12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-Nitrolinoleic acid 20V, Negative-QTOFsplash10-0002-9001000000-505f88f8006edd6f8a602021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-Nitrolinoleic acid 40V, Negative-QTOFsplash10-0002-9000000000-a0441e6336543cb884232021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-Nitrolinoleic acid 10V, Positive-QTOFsplash10-0a6r-1529000000-05090783185a6f4238b92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-Nitrolinoleic acid 20V, Positive-QTOFsplash10-0a4i-9557000000-ebb6c7e7374c05b886862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10-Nitrolinoleic acid 40V, Positive-QTOFsplash10-0aor-9200000000-9c5f80591993399939e82021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Phenol Explorer Compound IDNot Available
FooDB 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 ID34125
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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 ]