Showing metabocard for Linoelaidic acid (BMDB0006270)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:21:03 UTC
Update Date2020-06-04 22:43:33 UTC
MCDB ID BMDB0006270
Secondary Accession Numbers
  • BMDB06270
Metabolite Identification
Common NameLinoelaidic acid
DescriptionLinoleic acid, also known as linoleate, 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. Linoleic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Linoleic acid exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
18:2, N-6,9 all-transChEBI
9E,12E-Octadecadienoic acidChEBI
C18:2, N-6,9 all-transChEBI
trans-9,trans-12-Linoleic acidChEBI
9E,12E-OctadecadienoateGenerator
trans-9,trans-12-LinoleateGenerator
LinoelaidateGenerator
(9E,12E)-9,12-OctadecadienoateHMDB
(9E,12E)-9,12-Octadecadienoic acidHMDB
9,12-Octadecadienoic acidMeSH, HMDB
Linoleic acidMeSH, HMDB
Linoleic acid, (Z,Z)-isomer, 14C-labeledMeSH, HMDB
Linolelaidic acidMeSH, HMDB
cis,cis-9,12-Octadecadienoic acidMeSH, HMDB
Linoleic acid, (e,e)-isomerMeSH, HMDB
Linoleic acid, (Z,Z)-isomerMeSH, HMDB
Linoleic acid, ammonium salt, (Z,Z)-isomerMeSH, HMDB
Linoleic acid, potassium salt, (Z,Z)-isomerMeSH, HMDB
Linoelaidic acid, (e,Z)-isomerMeSH, HMDB
9 trans,12 trans Octadecadienoic acidMeSH, HMDB
Linoleic acid, sodium salt, (e,e)-isomerMeSH, HMDB
Linoleic acid, sodium salt, (Z,Z)-isomerMeSH, HMDB
Acid, 9,12-octadecadienoicMeSH, HMDB
trans,trans-9,12-Octadecadienoic acidMeSH, HMDB
Linoleic acid, (Z,e)-isomerMeSH, HMDB
9,12 Octadecadienoic acidMeSH, HMDB
Linoleic acid, calcium salt, (Z,Z)-isomerMeSH, HMDB
9-trans,12-trans-Octadecadienoic acidMeSH, HMDB
LinoleateMeSH, HMDB, Generator
Chemical FormulaC18H32O2
Average Molecular Weight280.4455
Monoisotopic Molecular Weight280.240230268
IUPAC Name(9E,12E)-octadeca-9,12-dienoic acid
Traditional Namelinoelaidic acid
CAS Registry Number506-21-8
SMILES
CCCCC\C=C\C\C=C\CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6+,10-9+
InChI KeyOYHQOLUKZRVURQ-AVQMFFATSA-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
  • Fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point28 - 29 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.06ALOGPS
logP6.42ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity88.52 m³·mol⁻¹ChemAxon
Polarizability35.45 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9750000000-50d69948d56dd2ba6e422016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9631000000-cc93c24bbf14d81ae9b62017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ec2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ec2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac3592017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac3592017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac3592017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-dd6cf3859995c0ba8be82017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0090000000-fdabfebc98e900a3a52b2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac3592017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0091000000-d8e32f26b102cfd394572017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-e1aa5a6fc5d53c0d0cb62017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-dd6cf3859995c0ba8be82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-fdabfebc98e900a3a52b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-e1aa5a6fc5d53c0d0cb62017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-fdabfebc98e900a3a52b2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-dd6cf3859995c0ba8be82021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0090000000-e1aa5a6fc5d53c0d0cb62021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0190000000-76fe39ad6bbee3f769e72016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0239-5690000000-9af1d7ecbc9ccf182d612016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-8930000000-0032f23abecb3b362ff22016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-b26f2ec0d32875acf8972016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-1090000000-08e28514e79444592bb52016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-d3f27ea65196f222f6cd2016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-03fd7d53d39127d027662021-09-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1090000000-e5b6404e73269d5a25282021-09-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9210000000-da81d6d1d7b1e626e9052021-09-21View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0006270
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023868
KNApSAcK IDC00036669
Chemspider ID4445609
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2217974
Wikipedia LinkLinoelaidic_acid
METLIN IDNot Available
PubChem Compound5282457
PDB IDNot Available
ChEBI ID75108
References
Synthesis ReferenceGunstone, Frank D.; Lie Ken Jie, M. Fatty acids. 24. Synthesis of ten octadecadiynoic acids and of the related cis,cis- and trans,trans-octadecadienoic acids. Chemistry and Physics of Lipids (1970), 4(1), 1-14.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026. [PubMed:29570652 ]