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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-11-09 23:15:32 UTC
HMDB IDHMDB0001388
Secondary Accession Numbers
  • HMDB01388
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. 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 humans 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 alpha-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). alpha-Linolenic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.
Structure
Data?1582752197
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
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-16.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP6.46SANGSTER (1993)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg173.07230932474
[M+H]+MetCCS_train_pos170.65430932474
[M-H]-Not Available173.8http://allccs.zhulab.cn/database/detail?ID=AllCCS00000248
[M+H]+Not Available170.998http://allccs.zhulab.cn/database/detail?ID=AllCCS00000248
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00027 g/LALOGPS
logP10(6.62) g/LALOGPS
logP10(6.06) g/LChemAxon
logS10(-6) g/LALOGPS
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
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]+176.97631661259
DarkChem[M-H]-176.48131661259
AllCCS[M+H]+175.4732859911
AllCCS[M-H]-176.88332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-Linolenic acidCC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O3410.4Standard polar33892256
alpha-Linolenic acidCC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O2036.2Standard non polar33892256
alpha-Linolenic acidCC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O2154.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
alpha-Linolenic acid,1TMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O[Si](C)(C)C2212.0Semi standard non polar33892256
alpha-Linolenic acid,1TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2453.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - alpha-Linolenic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-052f-7900000000-8765cf82603feb1b448f2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - alpha-Linolenic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-004i-9300000000-302519a616eaed5fcc592014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - alpha-Linolenic acid GC-MS (1 TMS)splash10-005c-9800000000-2d44b3c70e2992b9a8122014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - alpha-Linolenic acid GC-EI-TOF (Non-derivatized)splash10-052f-7900000000-8765cf82603feb1b448f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - alpha-Linolenic acid GC-EI-TOF (Non-derivatized)splash10-004i-9300000000-302519a616eaed5fcc592017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - alpha-Linolenic acid GC-MS (Non-derivatized)splash10-005c-9800000000-2d44b3c70e2992b9a8122017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - alpha-Linolenic acid GC-EI-TOF (Non-derivatized)splash10-052f-5900000000-28710ea35f196c595e032017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Linolenic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-052e-6950000000-27037263e74c8119ead02017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Linolenic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00ds-6931000000-657fa0cc66a206a364092017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Linolenic 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 - alpha-Linolenic acid Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-004i-0190000000-aee97e9ea2c7f0783adf2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Linolenic acid Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-05nb-9500000000-fb92aefc7010272393592012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Linolenic acid Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-0aru-9100000000-a5dddfe6f629d1371fac2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Linolenic acid ESI-TOF 10V, Negative-QTOFsplash10-004i-0090000000-2b7bea03a685454dd1352017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Linolenic acid ESI-TOF , Negative-QTOFsplash10-004i-0090000000-53ddfaed6ce13c37d9572017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Linolenic acid ESI-TOF 20V, Negative-QTOFsplash10-004i-0090000000-e5350a66361bc63d10712017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Linolenic acid ESI-TOF 30V, Negative-QTOFsplash10-004i-0090000000-5731aa5e301022c068132017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Linolenic acid ESI-TOF 10V, Negative-QTOFsplash10-004i-0091010000-6922411e48d747e592b52017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Linolenic acid LC-ESI-IT , negative-QTOFsplash10-001i-0090000000-a18b573ad888d048efa62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Linolenic acid LC-ESI-TOF , negative-QTOFsplash10-004i-0090000000-2b7bea03a685454dd1352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Linolenic acid LC-ESI-TOF , negative-QTOFsplash10-004i-0090000000-e5350a66361bc63d10712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Linolenic acid LC-ESI-TOF , negative-QTOFsplash10-004i-0090000000-5731aa5e301022c068132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Linolenic acid LC-ESI-QTOF 10V, positive-QTOFsplash10-004i-0090000000-1d391027db3704d71cb92020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Linolenic acid LC-ESI-QTOF 20V, positive-QTOFsplash10-00lr-9210000000-41acd8a55f52afec6d792020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Linolenic acid LC-ESI-QTOF 40V, positive-QTOFsplash10-014i-9000000000-a976b4a80a07eb2c46412020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Linolenic acid 40V, Positive-QTOFsplash10-0a4i-9100000000-497eddf5d738a45f83fb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Linolenic acid 10V, Negative-QTOFsplash10-004i-0090000000-0c00ca98901526cb2e262021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Linolenic acid 30V, Negative-QTOFsplash10-004i-1090000000-35ffce9343fe0d15ea0d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Linolenic acid 30V, Negative-QTOFsplash10-004i-0090000000-373584fbab950d6676cc2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Linolenic acid 10V, Positive-QTOFsplash10-01t9-0090000000-ae1f482177d0e208165e2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Linolenic acid 20V, Positive-QTOFsplash10-00o0-5690000000-20804c8382f14ff0ccf42017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Linolenic acid 40V, Positive-QTOFsplash10-014l-8930000000-9d5e342b1351adc71c202017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Linolenic acid 10V, Negative-QTOFsplash10-004i-0090000000-4d3e8d1180800a7b4ed52017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Linolenic acid 20V, Negative-QTOFsplash10-0059-1090000000-67ab14c068a142dd3c302017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Linolenic acid 40V, Negative-QTOFsplash10-0a4i-9230000000-403c610d63380e63109a2017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Adipose Tissue
  • Epidermis
  • Fibroblasts
  • Intestine
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified7.183 +/- 3.592 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified7.183 +/- 35.916 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified10.775 +/- 3.592 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified10.775 +/- 3.592 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified5.962 +/- 3.0528 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified72.191 +/- 31.606 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified79.0146 +/- 33.0425 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified8.548 +/- 3.771 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified80 +/- 30 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified100 +/- 40 uMAdult (>18 years old)MaleNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified5.11 +/- 3.8 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified17.5 +/- 7.6 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified16.8 +/- 7.3 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified18.5 +/- 7.9 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.1 +/- 0.8 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified1.975 +/- 1.223 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified73.0 +/- 45.6 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.115 +/- 0.004 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.73 +/- 0.54 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified66.803 +/- 30.169 uMAdult (>18 years old)BothDepression details
BloodDetected and Quantified21.2 +/- 7.2 uMAdult (>18 years old)BothHypertension details
BloodDetected and Quantified20.5 +/- 7.5 uMAdult (>18 years old)MaleEssential hypertension details
BloodDetected and Quantified22.7 +/- 6.2 uMAdult (>18 years old)FemaleEssential hypertension details
BloodDetected and Quantified24.8 +/- 13.3 uMAdult (>18 years old)Not Specified
Isovaleric acidemia
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified0.49 +/- 0.46 umol/mmol creatinineAdult (>18 years old)FemaleThyroid cancer details
Associated Disorders and Diseases
Disease References
Hypertension
  1. Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32. doi: 10.1291/hypres.31.623. [PubMed:18633173 ]
Essential hypertension
  1. Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32. doi: 10.1291/hypres.31.623. [PubMed:18633173 ]
Major depressive disorder
  1. Sublette ME, Segal-Isaacson CJ, Cooper TB, Fekri S, Vanegas N, Galfalvy HC, Oquendo MA, Mann JJ: Validation of a food frequency questionnaire to assess intake of n-3 polyunsaturated fatty acids in subjects with and without major depressive disorder. J Am Diet Assoc. 2011 Jan;111(1):117-123.e1-2. doi: 10.1016/j.jada.2010.10.007. [PubMed:21185973 ]
Isovaleric acidemia
  1. Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Thyroid cancer
  1. Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9. [PubMed:14643447 ]
Associated OMIM IDs
DrugBank IDDB00132
Phenol Explorer Compound IDNot Available
FooDB IDFDB012462
KNApSAcK IDC00007247
Chemspider ID4444437
KEGG Compound IDC06427
BioCyc IDLINOLENIC_ACID
BiGG ID48237
Wikipedia LinkAlpha-Linolenic_acid
METLIN ID6208
PubChem Compound5280934
PDB IDNot Available
ChEBI ID27432
Food Biomarker OntologyNot Available
VMH IDLNLNCA
MarkerDB IDMDB00000318
Good Scents IDNot Available
References
Synthesis ReferenceLi, Guihua; Qian, Xiangming; Jiang, Yanchao; Ma, Shushi. Preparation of a-linolenic acid from linseed oil. Zhengzhou Gongcheng Xueyuan Xuebao (2004), 25(3), 13-15.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Richieri GV, Ogata RT, Kleinfeld AM: Equilibrium constants for the binding of fatty acids with fatty acid-binding proteins from adipocyte, intestine, heart, and liver measured with the fluorescent probe ADIFAB. J Biol Chem. 1994 Sep 30;269(39):23918-30. [PubMed:7929039 ]
  2. Bajaj M, Suraamornkul S, Romanelli A, Cline GW, Mandarino LJ, Shulman GI, DeFronzo RA: Effect of a sustained reduction in plasma free fatty acid concentration on intramuscular long-chain fatty Acyl-CoAs and insulin action in type 2 diabetic patients. Diabetes. 2005 Nov;54(11):3148-53. [PubMed:16249438 ]
  3. Christensen JH, Fabrin K, Borup K, Barber N, Poulsen J: Prostate tissue and leukocyte levels of n-3 polyunsaturated fatty acids in men with benign prostate hyperplasia or prostate cancer. BJU Int. 2006 Feb;97(2):270-3. [PubMed:16430627 ]
  4. Attar-Bashi NM, Frauman AG, Sinclair AJ: Alpha-linolenic acid and the risk of prostate cancer. What is the evidence? J Urol. 2004 Apr;171(4):1402-7. [PubMed:15017185 ]
  5. Rastogi SK, Singh J: Effect of chemical penetration enhancer and iontophoresis on the in vitro percutaneous absorption enhancement of insulin through porcine epidermis. Pharm Dev Technol. 2005;10(1):97-104. [PubMed:15776817 ]
  6. Allman MA, Pena MM, Pang D: Supplementation with flaxseed oil versus sunflowerseed oil in healthy young men consuming a low fat diet: effects on platelet composition and function. Eur J Clin Nutr. 1995 Mar;49(3):169-78. [PubMed:7774533 ]
  7. Fokkema MR, Brouwer DA, Hasperhoven MB, Martini IA, Muskiet FA: Short-term supplementation of low-dose gamma-linolenic acid (GLA), alpha-linolenic acid (ALA), or GLA plus ALA does not augment LCP omega 3 status of Dutch vegans to an appreciable extent. Prostaglandins Leukot Essent Fatty Acids. 2000 Nov;63(5):287-92. [PubMed:11090255 ]
  8. Becker CC, Lund P, Holmer G, Jensen H, Sandstrom B: Effects of butter oil blends with increased concentrations of stearic, oleic and linolenic acid on blood lipids in young adults. Eur J Clin Nutr. 1999 Jul;53(7):535-41. [PubMed:10452408 ]
  9. Jones DB, Scaretto L, Carter R, Mann JI: Glucose, insulin and platelet fatty acids following myocardial infarction: an association with infarct size. Diabete Metab. 1987 Jul-Aug;13(4):463-6. [PubMed:3315767 ]
  10. Crastes de Paulet A, Babin F, Billeaud C, Bougle D, Sarda P, Mendy F: [Biological effects on premature neonates of a milk formula enriched with alpha-linolenic acid: a multicenter study]. Bull Acad Natl Med. 1994 Feb;178(2):267-73; discussion 273-8. [PubMed:7913655 ]
  11. Li D, Sinclair A, Wilson A, Nakkote S, Kelly F, Abedin L, Mann N, Turner A: Effect of dietary alpha-linolenic acid on thrombotic risk factors in vegetarian men. Am J Clin Nutr. 1999 May;69(5):872-82. [PubMed:10232625 ]
  12. Bhatia KS, Singh J: Effect of linolenic acid/ethanol or limonene/ethanol and iontophoresis on the in vitro percutaneous absorption of LHRH and ultrastructure of human epidermis. Int J Pharm. 1999 Apr 15;180(2):235-50. [PubMed:10370194 ]
  13. Baylin A, Kabagambe EK, Ascherio A, Spiegelman D, Campos H: Adipose tissue alpha-linolenic acid and nonfatal acute myocardial infarction in Costa Rica. Circulation. 2003 Apr 1;107(12):1586-91. Epub 2003 Mar 10. [PubMed:12668490 ]
  14. Williard DE, Nwankwo JO, Kaduce TL, Harmon SD, Irons M, Moser HW, Raymond GV, Spector AA: Identification of a fatty acid delta6-desaturase deficiency in human skin fibroblasts. J Lipid Res. 2001 Apr;42(4):501-8. [PubMed:11290821 ]
  15. Campbell FM, Gordon MJ, Dutta-Roy AK: Preferential uptake of long chain polyunsaturated fatty acids by isolated human placental membranes. Mol Cell Biochem. 1996 Feb 9;155(1):77-83. [PubMed:8717442 ]
  16. Cunnane SC, Hamadeh MJ, Liede AC, Thompson LU, Wolever TM, Jenkins DJ: Nutritional attributes of traditional flaxseed in healthy young adults. Am J Clin Nutr. 1995 Jan;61(1):62-8. [PubMed:7825540 ]
  17. Connor WE: Importance of n-3 fatty acids in health and disease. Am J Clin Nutr. 2000 Jan;71(1 Suppl):171S-5S. [PubMed:10617967 ]
  18. Lauritzen I, Blondeau N, Heurteaux C, Widmann C, Romey G, Lazdunski M: Polyunsaturated fatty acids are potent neuroprotectors. EMBO J. 2000 Apr 17;19(8):1784-93. [PubMed:10775263 ]
  19. Cho E, Hung S, Willett WC, Spiegelman D, Rimm EB, Seddon JM, Colditz GA, Hankinson SE: Prospective study of dietary fat and the risk of age-related macular degeneration. Am J Clin Nutr. 2001 Feb;73(2):209-18. [PubMed:11157315 ]
  20. Kris-Etherton PM, Harris WS, Appel LJ: Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease. Circulation. 2002 Nov 19;106(21):2747-57. [PubMed:12438303 ]
  21. Brouwer IA, Katan MB, Zock PL: Dietary alpha-linolenic acid is associated with reduced risk of fatal coronary heart disease, but increased prostate cancer risk: a meta-analysis. J Nutr. 2004 Apr;134(4):919-22. [PubMed:15051847 ]
  22. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 30 proteins in total.

Enzymes

General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:
PLA2G5
Uniprot ID:
P39877
Molecular weight:
15674.065
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + alpha-Linolenic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Molecular weight:
23256.29
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + alpha-Linolenic aciddetails
General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + alpha-Linolenic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Molecular weight:
16359.535
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + alpha-Linolenic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
Not known; does not seem to have catalytic activity.
Gene Name:
PLA2G12B
Uniprot ID:
Q9BX93
Molecular weight:
Not Available
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + alpha-Linolenic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:
PLA2G10
Uniprot ID:
O15496
Molecular weight:
18153.04
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + alpha-Linolenic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Molecular weight:
15988.525
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + alpha-Linolenic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Does not exhibit detectable activity toward sn-2-arachidonoyl- or linoleoyl-phosphatidylcholine or -phosphatidylethanolamine.
Gene Name:
PLA2G12A
Uniprot ID:
Q9BZM1
Molecular weight:
21066.99
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + alpha-Linolenic aciddetails
General function:
Involved in metabolic process
Specific function:
Catalyzes the release of fatty acids from phospholipids. It has been implicated in normal phospholipid remodeling, nitric oxide-induced or vasopressin-induced arachidonic acid release and in leukotriene and prostaglandin production. May participate in fas mediated apoptosis and in regulating transmembrane ion flux in glucose-stimulated B-cells. Has a role in cardiolipin (CL) deacylation. Required for both speed and directionality of monocyte MCP1/CCL2-induced chemotaxis through regulation of F-actin polymerization at the pseudopods. Isoform ankyrin-iPLA2-1 and isoform ankyrin-iPLA2-2, which lack the catalytic domain, are probably involved in the negative regulation of iPLA2 activity.
Gene Name:
PLA2G6
Uniprot ID:
O60733
Molecular weight:
84092.635
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + alpha-Linolenic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
Thought to participate in the regulation of the phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G2A
Uniprot ID:
P14555
Molecular weight:
16082.525
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + alpha-Linolenic aciddetails

Only showing the first 10 proteins. There are 30 proteins in total.