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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-05-22 20:46:11 UTC
Update Date2022-03-07 02:49:30 UTC
HMDB IDHMDB0006270
Secondary Accession Numbers
  • HMDB06270
Metabolite Identification
Common NameLinoelaidic acid
DescriptionLinoelaidic acid is an isomer of linoleic acid, or conjugated linoleic acid (CLA), a derivative of a fatty acid linoleic acid. Conjugated linoleic acid (CLA) isomers, a group of positional and geometric isomers of linoleic acid [18:2(n-6)], have been studied extensively due to their ability to modulate cancer, atherosclerosis, obesity, immune function and diabetes in a variety of experimental models. CLA's ability to modulate human obesity remains controversial because data from clinical trials using mixed isomers are conflicting. (PMID 10759137 ). Trans fatty acids are characteristically produced during industrial hydrogenation of plant oils.
Structure
Data?1582752378
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
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point28 - 29 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
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
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]+178.46231661259
DarkChem[M-H]-176.30931661259
DeepCCS[M+H]+176.07730932474
DeepCCS[M-H]-172.53730932474
DeepCCS[M-2H]-208.60230932474
DeepCCS[M+Na]+184.89230932474
AllCCS[M+H]+177.432859911
AllCCS[M+H-H2O]+174.332859911
AllCCS[M+NH4]+180.232859911
AllCCS[M+Na]+181.032859911
AllCCS[M-H]-178.532859911
AllCCS[M+Na-2H]-180.132859911
AllCCS[M+HCOO]-181.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Linoelaidic acidCCCCC\C=C\C\C=C\CCCCCCCC(O)=O3266.3Standard polar33892256
Linoelaidic acidCCCCC\C=C\C\C=C\CCCCCCCC(O)=O2067.0Standard non polar33892256
Linoelaidic acidCCCCC\C=C\C\C=C\CCCCCCCC(O)=O2140.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Linoelaidic acid,1TMS,isomer #1CCCCC/C=C/C/C=C/CCCCCCCC(=O)O[Si](C)(C)C2216.7Semi standard non polar33892256
Linoelaidic acid,1TBDMS,isomer #1CCCCC/C=C/C/C=C/CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2459.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Linoelaidic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9750000000-50d69948d56dd2ba6e422016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Linoelaidic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9631000000-cc93c24bbf14d81ae9b62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Linoelaidic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoelaidic acid ESI-TOF 10V, Negative-QTOFsplash10-0udi-0009000000-4dd23c77f8e48c0ab9ec2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoelaidic acid ESI-TOF 20V, Negative-QTOFsplash10-0udi-0009000000-4dd23c77f8e48c0ab9ec2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoelaidic acid ESI-TOF 10V, Negative-QTOFsplash10-004i-0092000000-b8aabbdc61f9b89ac3592017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoelaidic acid ESI-TOF , Negative-QTOFsplash10-004i-0092000000-b8aabbdc61f9b89ac3592017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoelaidic acid ESI-TOF 30V, Negative-QTOFsplash10-004i-0092000000-b8aabbdc61f9b89ac3592017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoelaidic acid ESI-TOF 10V, Negative-QTOFsplash10-004i-0090000000-dd6cf3859995c0ba8be82017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoelaidic acid ESI-TOF 20V, Negative-QTOFsplash10-004i-0090000000-fdabfebc98e900a3a52b2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoelaidic acid ESI-TOF 10V, Negative-QTOFsplash10-004i-0092000000-b8aabbdc61f9b89ac3592017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoelaidic acid ESI-TOF , Negative-QTOFsplash10-004i-0091000000-d8e32f26b102cfd394572017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoelaidic acid ESI-TOF 30V, Negative-QTOFsplash10-004i-0090000000-e1aa5a6fc5d53c0d0cb62017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoelaidic acid LC-ESI-TOF , negative-QTOFsplash10-004i-0090000000-dd6cf3859995c0ba8be82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoelaidic acid LC-ESI-TOF , negative-QTOFsplash10-004i-0090000000-fdabfebc98e900a3a52b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoelaidic acid LC-ESI-TOF , negative-QTOFsplash10-004i-0090000000-e1aa5a6fc5d53c0d0cb62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoelaidic acid 20V, Positive-QTOFsplash10-004i-0090000000-fdabfebc98e900a3a52b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoelaidic acid 10V, Positive-QTOFsplash10-004i-0090000000-dd6cf3859995c0ba8be82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linoelaidic acid 30V, Positive-QTOFsplash10-004i-0090000000-e1aa5a6fc5d53c0d0cb62021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoelaidic acid 10V, Positive-QTOFsplash10-01q9-0190000000-76fe39ad6bbee3f769e72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoelaidic acid 20V, Positive-QTOFsplash10-0239-5690000000-9af1d7ecbc9ccf182d612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoelaidic acid 40V, Positive-QTOFsplash10-006x-8930000000-0032f23abecb3b362ff22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoelaidic acid 10V, Negative-QTOFsplash10-004i-0090000000-b26f2ec0d32875acf8972016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoelaidic acid 20V, Negative-QTOFsplash10-004r-1090000000-08e28514e79444592bb52016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoelaidic acid 40V, Negative-QTOFsplash10-0a4l-9230000000-d3f27ea65196f222f6cd2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoelaidic acid 10V, Negative-QTOFsplash10-004i-0090000000-03fd7d53d39127d027662021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoelaidic acid 20V, Negative-QTOFsplash10-01t9-1090000000-e5b6404e73269d5a25282021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoelaidic acid 40V, Negative-QTOFsplash10-0006-9210000000-da81d6d1d7b1e626e9052021-09-21Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Lung cancer
details
Associated Disorders and Diseases
Disease References
Lung Cancer
  1. Chen Y, Ma Z, Min L, Li H, Wang B, Zhong J, Dai L: Biomarker identification and pathway analysis by serum metabolomics of lung cancer. Biomed Res Int. 2015;2015:183624. doi: 10.1155/2015/183624. Epub 2015 Apr 16. [PubMed:25961003 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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. MacDonald HB: Conjugated linoleic acid and disease prevention: a review of current knowledge. J Am Coll Nutr. 2000 Apr;19(2 Suppl):111S-118S. [PubMed:10759137 ]