Record Information
Version1.0
Creation Date2016-07-13 19:47:22 UTC
Update Date2016-09-23 18:45:11 UTC
LmdbLMDB00326
Secondary Accession NumbersNone
Metabolite Identification
Common NameAlpha-Linolenic acid
DescriptionAlpha-linolenic acid (ALA) is a polyunsaturated fatty acid (PUFA). It is a member of the group of essential fatty acids called omega-3 fatty acids. Alpha-linolenic acid, in particular, is not synthesized by mammals and therefore is an essential dietary requirement for all mammals. Certain nuts (English walnuts) and vegetable oils (canola, soybean, flaxseed/linseed, olive) are particularly rich in alpha-linolenic acid (ALA). Omega-3 fatty acids get their name based on the location of one of their first double bond. In all omega-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). Although animals and other mammals can synthesize saturated and some monounsaturated fatty acids from carbon groups in carbohydrates and proteins, they lack the enzymes necessary to insert a cis double bond at the n-6 or the n-3 position of a fatty acid. Omega-3 fatty acids like a-linolenic acid are important structural components of cell membranes. When incorporated into phospholipids, they affect cell membrane properties such as fluidity, flexibility, permeability and the activity of membrane bound enzymes. Omega-3 fatty acids can modulate the expression of a number of genes, including those involved with fatty acid metabolism and inflammation. Alpha linolenic acid and other omega 3 fatty acids may regulate gene expression by interacting with specific transcription factors, including peroxisome proliferator activated receptors (PPARs) and liver X receptors (LXRs).
Structure
Thumb
Synonyms
ValueSource
(9,12,15)-Linolenic acidChEBI
(9Z,12Z,15Z)-Octadecatrienoic acidChEBI
(Z,Z,Z)-9,12,15-Octadecatrienoic acidChEBI
9,12,15-Octadecatrienoic acidChEBI
9-cis,12-cis,15-cis-Octadecatrienoic acidChEBI
ALAChEBI
all-cis-9,12,15-Octadecatrienoic acidChEBI
cis,cis,cis-9,12,15-Octadecatrienoic acidChEBI
cis-Delta(9,12,15)-Octadecatrienoic acidChEBI
Linolenic acidChEBI
LinolenateKegg
alpha-LinolenateKegg
(9,12,15)-LinolenateGenerator
(9Z,12Z,15Z)-OctadecatrienoateGenerator
(Z,Z,Z)-9,12,15-OctadecatrienoateGenerator
9,12,15-OctadecatrienoateGenerator
9-cis,12-cis,15-cis-OctadecatrienoateGenerator
all-cis-9,12,15-OctadecatrienoateGenerator
cis,cis,cis-9,12,15-OctadecatrienoateGenerator
cis-delta(9,12,15)-OctadecatrienoateGenerator
cis-Δ(9,12,15)-octadecatrienoateGenerator
cis-Δ(9,12,15)-octadecatrienoic acidGenerator
a-LinolenateGenerator
a-Linolenic acidGenerator
Α-linolenateGenerator
Α-linolenic acidGenerator
alpha Linolenic acidHMDB
cis-9,12,15-OctadecatrienoateHMDB
cis-9,12,15-Octadecatrienoic acidHMDB
Industrene 120HMDB
FA(18:3(9Z,12Z,15Z))HMDB
FA(18:3n3)HMDB
Chemical FormulaC18H30O2
Average Molecular Weight278.4296
Monoisotopic Molecular Weight278.224580204
IUPAC Name(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
Traditional Nameα linolenic acid
CAS Registry Number463-40-1
SMILES
CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-
InChI KeyDTOSIQBPPRVQHS-PDBXOOCHSA-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
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.62ALOGPS
logP6.06ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity89.64 m³·mol⁻¹ChemAxon
Polarizability34.98 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-052f-7900000000-8765cf82603feb1b448fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-004i-9300000000-302519a616eaed5fcc59Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-005c-9800000000-2d44b3c70e2992b9a812Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052f-7900000000-8765cf82603feb1b448fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-9300000000-302519a616eaed5fcc59Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-005c-9800000000-2d44b3c70e2992b9a812Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052f-5900000000-28710ea35f196c595e03Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052e-6950000000-27037263e74c8119ead0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ds-6931000000-657fa0cc66a206a36409Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-004i-0190000000-aee97e9ea2c7f0783adfSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-05nb-9500000000-fb92aefc701027239359Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0aru-9100000000-a5dddfe6f629d1371facSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-2b7bea03a685454dd135Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0090000000-53ddfaed6ce13c37d957Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0090000000-e5350a66361bc63d1071Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-5731aa5e301022c06813Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0091010000-6922411e48d747e592b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-001i-0090000000-a18b573ad888d048efa6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-2b7bea03a685454dd135Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-e5350a66361bc63d1071Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-5731aa5e301022c06813Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-004i-0090000000-1d391027db3704d71cb9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-00lr-9210000000-41acd8a55f52afec6d79Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-014i-9000000000-a976b4a80a07eb2c4641Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-497eddf5d738a45f83fbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-0c00ca98901526cb2e26Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004i-1090000000-35ffce9343fe0d15ea0dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004i-0090000000-373584fbab950d6676ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0090000000-ae1f482177d0e208165eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00o0-5690000000-20804c8382f14ff0ccf4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-8930000000-9d5e342b1351adc71c20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-4d3e8d1180800a7b4ed5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1090000000-67ab14c068a142dd3c30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9230000000-403c610d63380e63109aSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Follicular Fluid
  • Milk
  • Muscle
  • Oocyte
  • Oocyte (zona-intact oocytes)
  • Ruminal Fluid
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Follicular FluidDetected but not QuantifiedNot ApplicableNot AvailablePorcine
    • Warzych, E., Cies...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine
    • H. Steinshamn, R....
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine
    • H. Steinshamn, R....
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine
    • H. Steinshamn, R....
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine
    • H. Steinshamn, R....
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected and Quantified1000 mg/kgNot AvailableBovine
    • M.J. Abarghuei, Y...
details
MilkDetected and Quantified1100 mg/kgNot AvailableBovine
    • M.J. Abarghuei, Y...
details
MilkDetected and Quantified1100 mg/kgNot AvailableBovine
    • M.J. Abarghuei, Y...
details
MilkDetected and Quantified1300 mg/kgNot AvailableBovine
    • M.J. Abarghuei, Y...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
details
MuscleDetected but not QuantifiedNot ApplicableNot AvailableBovine details
OocyteDetected but not QuantifiedNot ApplicableNot AvailableOvine details
Oocyte (zona-intact oocytes)Detected but not QuantifiedNot ApplicableNot AvailableBovine details
Oocyte (zona-intact oocytes)Detected but not QuantifiedNot ApplicableNot AvailablePorcine details
Oocyte (zona-intact oocytes)Detected but not QuantifiedNot ApplicableNot AvailablePorcine details
Ruminal FluidDetected and Quantified0.5 +/- 0.4 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
DrugBank IDDB00132
HMDB IDHMDB0001388
FooDB IDFDB012462
Phenol Explorer IDNot Available
KNApSAcK IDC00007247
BiGG ID48237
BioCyc IDLINOLENIC_ACID
METLIN ID6208
PDB IDNot Available
Wikipedia LinkAlpha-Linolenic_acid
Chemspider ID4444437
ChEBI ID27432
PubChem Compound ID5280934
Kegg Compound IDC06427
YMDB IDNot Available
ECMDB IDECMDB01388
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available