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Human Metabolome Database Version 3.5

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Showing metabocard for Alpha-Linolenic acid (HMDB01388)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:27 -0700
HMDB ID HMDB01388
Secondary Accession Numbers None
Metabolite Identification
Common Name Alpha-Linolenic acid
Description Alpha-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 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 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (9,12,15)-linolenate
  2. (9,12,15)-linolenic acid
  3. (9Z,12Z,15Z)-Octadecatrienoate
  4. (9Z,12Z,15Z)-Octadecatrienoic acid
  5. (Z,Z,Z)-9,12,15-Octadecatrienoate
  6. (Z,Z,Z)-9,12,15-Octadecatrienoic acid
  7. 9,12,15-Octadecatrienoate
  8. 9,12,15-Octadecatrienoic acid
  9. 9-cis,12-cis,15-cis-Octadecatrienoate
  10. 9-cis,12-cis,15-cis-Octadecatrienoic acid
  11. a-Linolenate
  12. a-Linolenic acid
  13. All-cis-9,12,15-Octadecatrienoate
  14. All-cis-9,12,15-Octadecatrienoic acid
  15. alpha-Linolenate
  16. alpha-Linolenic acid
  17. cis,cis,cis-9,12,15-Octadecatrienoate
  18. cis,cis,cis-9,12,15-Octadecatrienoic acid
  19. cis-9,12,15-Octadecatrienoate
  20. cis-9,12,15-Octadecatrienoic acid
  21. Industrene 120
  22. Linolenate
  23. Linolenic acid
Chemical Formula C18H30O2
Average Molecular Weight 278.4296
Monoisotopic Molecular Weight 278.224580204
IUPAC Name (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
Traditional IUPAC Name α-linolenic acid
CAS Registry Number 463-40-1
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 Key DTOSIQBPPRVQHS-PDBXOOCHSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Lineolic Acids and Derivatives
Sub Class N/A
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Polyunsaturated fatty acids(KEGG)
  • Straight Chain Fatty Acids
  • Unsaturated Fatty Acids
  • Unsaturated fatty acids(KEGG)
  • Unsaturated fatty acids(Lipidmaps)
  • linolenic acid(ChEBI)
  • omega-3 fatty acid(ChEBI)
Substituents
  • Acyclic Alkene
  • Carboxylic Acid
Direct Parent Lineolic Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Food
  • Drug
Biofunction
  • Cell signaling
  • Essential fatty acid
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point -16.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 6.46 SANGSTER (1993)
Predicted Properties
Property Value Source
Water Solubility 2.660E-04 g/L ALOGPS
LogP 6.62 ALOGPS
LogP 6.06 ChemAxon
LogS -6.02 ALOGPS
pKa (strongest acidic) 4.99 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 13 ChemAxon
Refractivity 89.64 ChemAxon
Polarizability 34.44 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Muscle
  • Fibroblasts
  • Intestine
  • Placenta
  • Epidermis
  • Prostate
  • Adipose Tissue
  • Platelet
  • Nervous Tissues
Pathways
Name SMPDB Link KEGG Link
Alpha Linolenic Acid and Linoleic Acid Metabolism SMP00018 map00592 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
5.11 +/- 3.8 uM Adult (>18 years old) Not Specified Normal Not Available
Blood Detected and Quantified
Article_icon
17.5 +/- 7.6 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
16.8 +/- 7.3 uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
Article_icon
18.5 +/- 7.9 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
1.1 +/- 0.8 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
1.975 +/- 1.223 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
0.115 +/- 0.004 uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.73 +/- 0.54 umol/mmol creatinine Adult (>18 years old) Female Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
21.2 +/- 7.2 uM Adult (>18 years old) Both Hypertension Not Available
Blood Detected and Quantified
Article_icon
20.5 +/- 7.5 uM Adult (>18 years old) Male Essential hypertension Not Available
Blood Detected and Quantified
Article_icon
22.7 +/- 6.2 uM Adult (>18 years old) Female Essential hypertension Not Available
Urine Detected and Quantified
Article_icon
0.49 +/- 0.46 umol/mmol creatinine Adult (>18 years old) Female Cancer Not Available
Associated Disorders and Diseases
Disease References
Hypertension
  • 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. Pubmed: 18633173 Link_out
    Essential hypertension
    • 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. Pubmed: 18633173 Link_out
      Thyroid cancer
      • 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 Link_out
        Associated OMIM IDs
        DrugBank ID DB00132 Link_out
        Phenol Explorer Compound ID Not Available
        Phenol Explorer Metabolite ID Not Available
        FoodDB ID FDB012462
        KNApSAcK ID C00007247 Link_out
        Chemspider ID 4444437 Link_out
        KEGG Compound ID C06427 Link_out
        BioCyc ID LINOLENIC_ACID Link_out
        BiGG ID 48237 Link_out
        Wikipedia Link Linolenic acid Link_out
        NuGOwiki Link HMDB01388 Link_out
        Metagene Link HMDB01388 Link_out
        METLIN ID 6208 Link_out
        PubChem Compound 5280934 Link_out
        PDB ID LNL Link_out
        ChEBI ID 27432 Link_out
        References
        Synthesis Reference Li, 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. 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 Link_out
        2. 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 Link_out
        3. 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 Link_out
        4. 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 Link_out
        5. 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 Link_out
        6. 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 Link_out
        7. 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 Link_out
        8. 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 Link_out
        9. 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 Link_out
        10. 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 Link_out
        11. 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 Link_out
        12. 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 Link_out
        13. 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 Link_out
        14. 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 Link_out
        15. 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 Link_out
        16. 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 Link_out
        Enzymes
        Name: Calcium-dependent phospholipase A2
        Reactions:
        • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
        Gene Name: PLA2G5
        Uniprot ID: P39877 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Group IIF secretory phospholipase A2
        Reactions:
        • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
        Gene Name: PLA2G2F
        Uniprot ID: Q9BZM2 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytosolic phospholipase A2
        Reactions:
        • 2-lysophosphatidylcholine + H2O = glycerophosphocholine + a carboxylate [RN:R07291]
        Gene Name: PLA2G4A
        Uniprot ID: P47712 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Phospholipase A2
        Reactions:
        • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
        Gene Name: PLA2G1B
        Uniprot ID: P04054 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Group XIIB secretory phospholipase A2-like protein
        Reactions:
          Gene Name: PLA2G12B
          Uniprot ID: Q9BX93 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Group 10 secretory phospholipase A2
          Reactions:
          • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
          Gene Name: PLA2G10
          Uniprot ID: O15496 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Group IIE secretory phospholipase A2
          Reactions:
          • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
          Gene Name: PLA2G2E
          Uniprot ID: Q9NZK7 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: 85 kDa calcium-independent phospholipase A2
          Reactions:
          • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
          Gene Name: PLA2G6
          Uniprot ID: O60733 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Group IID secretory phospholipase A2
          Reactions:
          • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
          Gene Name: PLA2G2D
          Uniprot ID: Q9UNK4 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Group 3 secretory phospholipase A2
          Reactions:
          • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
          Gene Name: PLA2G3
          Uniprot ID: Q9NZ20 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Bile acid-CoA:amino acid N-acyltransferase
          Reactions:
          • palmitoyl-CoA + H2O = CoA + palmitate [RN:R01274]
          Gene Name: BAAT
          Uniprot ID: Q14032 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Cytosolic acyl coenzyme A thioester hydrolase
          Reactions:
          • palmitoyl-CoA + H2O = CoA + palmitate [RN:R01274]
          Gene Name: ACOT7
          Uniprot ID: O00154 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Acyl-coenzyme A thioesterase 2, mitochondrial
          Reactions:
          • palmitoyl-CoA + H2O = CoA + palmitate [RN:R01274]
          Gene Name: ACOT2
          Uniprot ID: P49753 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Acyl-coenzyme A thioesterase 4
          Reactions:
          • palmitoyl-CoA + H2O = CoA + palmitate [RN:R01274]
          Gene Name: ACOT4
          Uniprot ID: Q8N9L9 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Acyl-coenzyme A thioesterase 8
          Reactions:
          • choloyl-CoA + H2O = cholate + CoA [RN:R07296]
          Gene Name: ACOT8
          Uniprot ID: O14734 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Transient receptor potential cation channel subfamily V member 1
          Reactions:
            Gene Name: TRPV1
            Uniprot ID: Q8NER1 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Fatty acid desaturase 1
            Reactions:
            • --- []
            Gene Name: FADS1
            Uniprot ID: O60427 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Sodium/calcium exchanger 1
            Reactions:
            • --- []
            Gene Name: SLC8A1
            Uniprot ID: P32418 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Fatty acid desaturase 2
            Reactions:
            • --- []
            Gene Name: FADS2
            Uniprot ID: O95864 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Elongation of very long chain fatty acids protein 4
            Reactions:
              Gene Name: ELOVL4
              Uniprot ID: Q9GZR5 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Cytosolic phospholipase A2 beta
              Reactions:
              • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
              Gene Name: PLA2G4B
              Uniprot ID: P0C869 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA