Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (30) Show 30 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:09 UTC

HMDB ID

HMDB0001388

Secondary Accession Numbers

HMDB01388

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. 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0001388
     RDKit          3D
alpha-Linolenic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
   -8.3044    0.9772   -0.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5366    0.5811    0.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9361   -0.7218    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6605   -0.9439    0.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6012    0.0787    0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8848   -0.3389    1.6479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6156   -0.5780    1.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8226   -0.4490    0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7760    0.5682    0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5062    0.3892    0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1119   -0.8999    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9432   -0.7910   -0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0418    0.2128   -0.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9535   -0.1577    0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0534    0.8720    0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8647    0.9524   -0.8365 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5327   -0.3449   -1.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4449   -0.7382   -0.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9769   -1.2031    0.9280 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8097   -0.5999   -0.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5779    1.2379   -1.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9030    1.8750   -0.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9564    0.1453   -1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9400    1.4352    0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3928    0.4335    1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6135   -1.5577   -0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3237   -1.9850   -0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1301    1.0543    0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0988    0.2474   -0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5056   -0.4351    2.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869   -0.8917    2.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4083   -1.4728    0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3055   -0.1763   -0.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1409    1.5790    0.9321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1600    1.2410    0.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7913   -1.2253    1.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3894   -1.7209    0.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917   -0.4217   -1.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4180   -1.7595   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5822    1.2024   -0.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6402    0.2729   -1.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3873   -0.0912    1.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3313   -1.1984    0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6776    0.6927    1.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5177    1.8630    0.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2889    1.3594   -1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7169    1.6761   -0.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0985   -0.1397   -2.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7934   -1.1531   -1.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1981    0.2509   -0.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
M  END


  Mrv1652309272007302D          

 20 19  0  0  0  0            999 V2000
    2.0296   -3.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3145   -3.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6012   -3.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1137   -3.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8269   -3.9278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1137   -2.6913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9358   -3.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6510   -3.9223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1114   -3.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3963   -3.9223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7435   -3.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4586   -3.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1724   -3.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4264   -3.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6020   -3.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8868   -3.9223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6811   -3.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8567   -3.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1416   -3.9223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3648   -3.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
  1 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 13 16  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 17 10  1  0  0  0  0
  8 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001388

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C18H30O2

> <MOLECULAR_WEIGHT>
278.4296

> <EXACT_MASS>
278.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
34.98036100681455

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid

> <ALOGPS_LOGP>
6.62

> <JCHEM_LOGP>
6.059955137666666

> <ALOGPS_LOGS>
-6.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167283903808

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
89.6354

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.66e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α linolenic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001388
     RDKit          3D
alpha-Linolenic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
   -8.3044    0.9772   -0.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5366    0.5811    0.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9361   -0.7218    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6605   -0.9439    0.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6012    0.0787    0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8848   -0.3389    1.6479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6156   -0.5780    1.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8226   -0.4490    0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7760    0.5682    0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5062    0.3892    0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1119   -0.8999    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9432   -0.7910   -0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0418    0.2128   -0.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9535   -0.1577    0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0534    0.8720    0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8647    0.9524   -0.8365 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5327   -0.3449   -1.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4449   -0.7382   -0.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9769   -1.2031    0.9280 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8097   -0.5999   -0.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5779    1.2379   -1.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9030    1.8750   -0.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9564    0.1453   -1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9400    1.4352    0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3928    0.4335    1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6135   -1.5577   -0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3237   -1.9850   -0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1301    1.0543    0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0988    0.2474   -0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5056   -0.4351    2.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869   -0.8917    2.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4083   -1.4728    0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3055   -0.1763   -0.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1409    1.5790    0.9321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1600    1.2410    0.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7913   -1.2253    1.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3894   -1.7209    0.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917   -0.4217   -1.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4180   -1.7595   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5822    1.2024   -0.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6402    0.2729   -1.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3873   -0.0912    1.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3313   -1.1984    0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6776    0.6927    1.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5177    1.8630    0.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2889    1.3594   -1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7169    1.6761   -0.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0985   -0.1397   -2.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7934   -1.1531   -1.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1981    0.2509   -0.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0       3.789  -7.332   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.454  -6.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.122  -7.332   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.212  -6.564   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.544  -7.332   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -0.212  -5.024   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      20.413  -6.554   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.749  -7.322   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.875  -6.554   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.540  -7.322   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.121  -6.560   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.456  -7.328   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.788  -6.556   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.996  -6.554   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.457  -6.554   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.122  -7.322   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.205  -6.554   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.666  -6.554   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.331  -7.322   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.081  -6.549   0.000  0.00  0.00           C+0
CONECT    1    2   11                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    8    9                                                       
CONECT    8    7   20                                                       
CONECT    9    7   10                                                       
CONECT   10    9   17                                                       
CONECT   11    1   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   16                                                       
CONECT   14   15   19                                                       
CONECT   15   14   16                                                       
CONECT   16   15   13                                                       
CONECT   17   18   10                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    8                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    HMDB0001388
HETATM    1  C1  UNL     1      -8.304   0.977  -0.960  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.537   0.581   0.324  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.936  -0.722   0.112  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.660  -0.944   0.170  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.601   0.079   0.459  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.885  -0.339   1.648  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.616  -0.578   1.622  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.823  -0.449   0.417  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.776   0.568   0.668  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.506   0.389   0.608  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.112  -0.900   0.270  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.943  -0.791  -0.979  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.042   0.213  -0.818  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.953  -0.158   0.298  1.00  0.00           C  
HETATM   15  C15 UNL     1       5.053   0.872   0.419  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.865   0.952  -0.836  1.00  0.00           C  
HETATM   17  C17 UNL     1       6.533  -0.345  -1.217  1.00  0.00           C  
HETATM   18  C18 UNL     1       7.445  -0.738  -0.129  1.00  0.00           C  
HETATM   19  O1  UNL     1       6.977  -1.203   0.928  1.00  0.00           O  
HETATM   20  O2  UNL     1       8.810  -0.600  -0.262  1.00  0.00           O  
HETATM   21  H1  UNL     1      -7.578   1.238  -1.754  1.00  0.00           H  
HETATM   22  H2  UNL     1      -8.903   1.875  -0.701  1.00  0.00           H  
HETATM   23  H3  UNL     1      -8.956   0.145  -1.250  1.00  0.00           H  
HETATM   24  H4  UNL     1      -6.940   1.435   0.565  1.00  0.00           H  
HETATM   25  H5  UNL     1      -8.393   0.434   1.066  1.00  0.00           H  
HETATM   26  H6  UNL     1      -7.613  -1.558  -0.108  1.00  0.00           H  
HETATM   27  H7  UNL     1      -5.324  -1.985  -0.011  1.00  0.00           H  
HETATM   28  H8  UNL     1      -5.130   1.054   0.683  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.099   0.247  -0.470  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.506  -0.435   2.569  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.087  -0.892   2.527  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.408  -1.473   0.206  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.305  -0.176  -0.526  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.141   1.579   0.932  1.00  0.00           H  
HETATM   35  H15 UNL     1       1.160   1.241   0.826  1.00  0.00           H  
HETATM   36  H16 UNL     1       1.791  -1.225   1.136  1.00  0.00           H  
HETATM   37  H17 UNL     1       0.389  -1.721   0.225  1.00  0.00           H  
HETATM   38  H18 UNL     1       1.292  -0.422  -1.816  1.00  0.00           H  
HETATM   39  H19 UNL     1       2.418  -1.760  -1.251  1.00  0.00           H  
HETATM   40  H20 UNL     1       2.582   1.202  -0.586  1.00  0.00           H  
HETATM   41  H21 UNL     1       3.640   0.273  -1.765  1.00  0.00           H  
HETATM   42  H22 UNL     1       3.387  -0.091   1.278  1.00  0.00           H  
HETATM   43  H23 UNL     1       4.331  -1.198   0.232  1.00  0.00           H  
HETATM   44  H24 UNL     1       5.678   0.693   1.319  1.00  0.00           H  
HETATM   45  H25 UNL     1       4.518   1.863   0.501  1.00  0.00           H  
HETATM   46  H26 UNL     1       5.289   1.359  -1.663  1.00  0.00           H  
HETATM   47  H27 UNL     1       6.717   1.676  -0.666  1.00  0.00           H  
HETATM   48  H28 UNL     1       7.099  -0.140  -2.160  1.00  0.00           H  
HETATM   49  H29 UNL     1       5.793  -1.153  -1.419  1.00  0.00           H  
HETATM   50  H30 UNL     1       9.198   0.251  -0.662  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4    4   26
CONECT    4    5   27
CONECT    5    6   28   29
CONECT    6    7    7   30
CONECT    7    8   31
CONECT    8    9   32   33
CONECT    9   10   10   34
CONECT   10   11   35
CONECT   11   12   36   37
CONECT   12   13   38   39
CONECT   13   14   40   41
CONECT   14   15   42   43
CONECT   15   16   44   45
CONECT   16   17   46   47
CONECT   17   18   48   49
CONECT   18   19   19   20
CONECT   20   50
END

HMDB0001388
     RDKit          3D
alpha-Linolenic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
   -8.3044    0.9772   -0.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5366    0.5811    0.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9361   -0.7218    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6605   -0.9439    0.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6012    0.0787    0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8848   -0.3389    1.6479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6156   -0.5780    1.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8226   -0.4490    0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7760    0.5682    0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5062    0.3892    0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1119   -0.8999    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9432   -0.7910   -0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0418    0.2128   -0.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9535   -0.1577    0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0534    0.8720    0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8647    0.9524   -0.8365 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5327   -0.3449   -1.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4449   -0.7382   -0.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9769   -1.2031    0.9280 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8097   -0.5999   -0.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5779    1.2379   -1.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9030    1.8750   -0.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9564    0.1453   -1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9400    1.4352    0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3928    0.4335    1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6135   -1.5577   -0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3237   -1.9850   -0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1301    1.0543    0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0988    0.2474   -0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5056   -0.4351    2.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869   -0.8917    2.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4083   -1.4728    0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3055   -0.1763   -0.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1409    1.5790    0.9321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1600    1.2410    0.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7913   -1.2253    1.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3894   -1.7209    0.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917   -0.4217   -1.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4180   -1.7595   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5822    1.2024   -0.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6402    0.2729   -1.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3873   -0.0912    1.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3313   -1.1984    0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6776    0.6927    1.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5177    1.8630    0.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2889    1.3594   -1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7169    1.6761   -0.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0985   -0.1397   -2.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7934   -1.1531   -1.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1981    0.2509   -0.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(9,12,15)-Linolenic acid	ChEBI
(9Z,12Z,15Z)-Octadecatrienoic acid	ChEBI
(Z,Z,Z)-9,12,15-Octadecatrienoic acid	ChEBI
9,12,15-Octadecatrienoic acid	ChEBI
9-cis,12-cis,15-cis-Octadecatrienoic acid	ChEBI
ALA	ChEBI
all-cis-9,12,15-Octadecatrienoic acid	ChEBI
cis,cis,cis-9,12,15-Octadecatrienoic acid	ChEBI
cis-Delta(9,12,15)-Octadecatrienoic acid	ChEBI
Linolenic acid	ChEBI
Linolenate	Kegg
alpha-Linolenate	Kegg
(9,12,15)-Linolenate	Generator
(9Z,12Z,15Z)-Octadecatrienoate	Generator
(Z,Z,Z)-9,12,15-Octadecatrienoate	Generator
9,12,15-Octadecatrienoate	Generator
9-cis,12-cis,15-cis-Octadecatrienoate	Generator
all-cis-9,12,15-Octadecatrienoate	Generator
cis,cis,cis-9,12,15-Octadecatrienoate	Generator
cis-delta(9,12,15)-Octadecatrienoate	Generator
cis-Δ(9,12,15)-octadecatrienoate	Generator
cis-Δ(9,12,15)-octadecatrienoic acid	Generator
a-Linolenate	Generator
a-Linolenic acid	Generator
Α-linolenate	Generator
Α-linolenic acid	Generator
alpha Linolenic acid	HMDB
cis-9,12,15-Octadecatrienoate	HMDB
cis-9,12,15-Octadecatrienoic acid	HMDB
Industrene 120	HMDB
FA(18:3(9Z,12Z,15Z))	HMDB
FA(18:3n3)	HMDB

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 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

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic 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 Framework

Aliphatic acyclic compounds

External Descriptors

omega-3 fatty acid (CHEBI:27432 )
linolenic acid (CHEBI:27432 )
Unsaturated fatty acids (C06427 )
Polyunsaturated fatty acids (C06427 )
Unsaturated fatty acids (LMFA01030152 )

Ontology

Not Available

Physical Properties

State

Liquid

Experimental Molecular 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)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	173.072	30932474
[M+H]+	MetCCS_train_pos	170.654	30932474
[M-H]-	Not Available	173.8	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000248
[M+H]+	Not Available	170.998	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000248

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00027 g/L	ALOGPS
logP	6.62	ALOGPS
logP	6.06	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	89.64 m³·mol⁻¹	ChemAxon
Polarizability	34.98 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	176.976	31661259
DarkChem	[M-H]-	176.481	31661259
AllCCS	[M+H]+	175.47	32859911
AllCCS	[M-H]-	176.883	32859911
DeepCCS	[M+H]+	174.181	30932474
DeepCCS	[M-H]-	171.823	30932474
DeepCCS	[M-2H]-	204.831	30932474
DeepCCS	[M+Na]+	180.274	30932474
AllCCS	[M+H]+	175.5	32859911
AllCCS	[M+H-H2O]+	172.3	32859911
AllCCS	[M+NH4]+	178.4	32859911
AllCCS	[M+Na]+	179.2	32859911
AllCCS	[M-H]-	176.9	32859911
AllCCS	[M+Na-2H]-	178.4	32859911
AllCCS	[M+HCOO]-	180.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Linolenic acid	CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O	3410.4	Standard polar	33892256
alpha-Linolenic acid	CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O	2036.2	Standard non polar	33892256
alpha-Linolenic acid	CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O	2154.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
alpha-Linolenic acid,1TMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O[Si](C)(C)C	2212.0	Semi standard non polar	33892256
alpha-Linolenic acid,1TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2453.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - alpha-Linolenic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-052f-7900000000-8765cf82603feb1b448f	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - alpha-Linolenic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-004i-9300000000-302519a616eaed5fcc59	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - alpha-Linolenic acid GC-MS (1 TMS)	splash10-005c-9800000000-2d44b3c70e2992b9a812	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - alpha-Linolenic acid GC-EI-TOF (Non-derivatized)	splash10-052f-7900000000-8765cf82603feb1b448f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - alpha-Linolenic acid GC-EI-TOF (Non-derivatized)	splash10-004i-9300000000-302519a616eaed5fcc59	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - alpha-Linolenic acid GC-MS (Non-derivatized)	splash10-005c-9800000000-2d44b3c70e2992b9a812	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - alpha-Linolenic acid GC-EI-TOF (Non-derivatized)	splash10-052f-5900000000-28710ea35f196c595e03	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Linolenic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-052e-6950000000-27037263e74c8119ead0	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Linolenic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00ds-6931000000-657fa0cc66a206a36409	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Linolenic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Linolenic acid Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-004i-0190000000-aee97e9ea2c7f0783adf	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Linolenic acid Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-05nb-9500000000-fb92aefc701027239359	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Linolenic acid Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-0aru-9100000000-a5dddfe6f629d1371fac	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Linolenic acid ESI-TOF 10V, Negative-QTOF	splash10-004i-0090000000-2b7bea03a685454dd135	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Linolenic acid ESI-TOF , Negative-QTOF	splash10-004i-0090000000-53ddfaed6ce13c37d957	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Linolenic acid ESI-TOF 20V, Negative-QTOF	splash10-004i-0090000000-e5350a66361bc63d1071	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Linolenic acid ESI-TOF 30V, Negative-QTOF	splash10-004i-0090000000-5731aa5e301022c06813	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Linolenic acid ESI-TOF 10V, Negative-QTOF	splash10-004i-0091010000-6922411e48d747e592b5	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Linolenic acid LC-ESI-IT , negative-QTOF	splash10-001i-0090000000-a18b573ad888d048efa6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Linolenic acid LC-ESI-TOF , negative-QTOF	splash10-004i-0090000000-2b7bea03a685454dd135	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Linolenic acid LC-ESI-TOF , negative-QTOF	splash10-004i-0090000000-e5350a66361bc63d1071	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Linolenic acid LC-ESI-TOF , negative-QTOF	splash10-004i-0090000000-5731aa5e301022c06813	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Linolenic acid LC-ESI-QTOF 10V, positive-QTOF	splash10-004i-0090000000-1d391027db3704d71cb9	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Linolenic acid LC-ESI-QTOF 20V, positive-QTOF	splash10-00lr-9210000000-41acd8a55f52afec6d79	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Linolenic acid LC-ESI-QTOF 40V, positive-QTOF	splash10-014i-9000000000-a976b4a80a07eb2c4641	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Linolenic acid 40V, Positive-QTOF	splash10-0a4i-9100000000-497eddf5d738a45f83fb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Linolenic acid 10V, Negative-QTOF	splash10-004i-0090000000-0c00ca98901526cb2e26	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Linolenic acid 30V, Negative-QTOF	splash10-004i-1090000000-35ffce9343fe0d15ea0d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Linolenic acid 30V, Negative-QTOF	splash10-004i-0090000000-373584fbab950d6676cc	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Linolenic acid 10V, Positive-QTOF	splash10-01t9-0090000000-ae1f482177d0e208165e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Linolenic acid 20V, Positive-QTOF	splash10-00o0-5690000000-20804c8382f14ff0ccf4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Linolenic acid 40V, Positive-QTOF	splash10-014l-8930000000-9d5e342b1351adc71c20	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Linolenic acid 10V, Negative-QTOF	splash10-004i-0090000000-4d3e8d1180800a7b4ed5	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Linolenic acid 20V, Negative-QTOF	splash10-0059-1090000000-67ab14c068a142dd3c30	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Linolenic acid 40V, Negative-QTOF	splash10-0a4i-9230000000-403c610d63380e63109a	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View 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

Name	SMPDB/PathBank	KEGG
alpha-Linolenic acid metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	7.183 +/- 3.592 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	7.183 +/- 35.916 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	10.775 +/- 3.592 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	10.775 +/- 3.592 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	5.962 +/- 3.0528 uM	Adult (>18 years old)	Both	Normal	17313719	details
Blood	Detected and Quantified	72.191 +/- 31.606 uM	Adult (>18 years old)	Both	Normal	21185973	details
Blood	Detected and Quantified	79.0146 +/- 33.0425 uM	Adult (>18 years old)	Both	Normal	21185973	details
Blood	Detected and Quantified	8.548 +/- 3.771 uM	Adult (>18 years old)	Female	Normal	9368807	details
Blood	Detected and Quantified	80 +/- 30 uM	Adult (>18 years old)	Female	Normal	14608088	details
Blood	Detected and Quantified	100 +/- 40 uM	Adult (>18 years old)	Male	Normal	14608088	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	5.11 +/- 3.8 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	17.5 +/- 7.6 uM	Adult (>18 years old)	Both	Normal	18633173	details
Blood	Detected and Quantified	16.8 +/- 7.3 uM	Adult (>18 years old)	Male	Normal	18633173	details
Blood	Detected and Quantified	18.5 +/- 7.9 uM	Adult (>18 years old)	Both	Normal	18633173	details
Blood	Detected and Quantified	1.1 +/- 0.8 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	1.975 +/- 1.223 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	73.0 +/- 45.6 uM	Adult (>18 years old)	Not Specified	Normal	27329611	details
Blood	Detected and Quantified	0.115 +/- 0.004 uM	Adult (>18 years old)	Both	Normal	20671299	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.73 +/- 0.54 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	14643447	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	66.803 +/- 30.169 uM	Adult (>18 years old)	Both	Depression	21185973	details
Blood	Detected and Quantified	21.2 +/- 7.2 uM	Adult (>18 years old)	Both	Hypertension	18633173	details
Blood	Detected and Quantified	20.5 +/- 7.5 uM	Adult (>18 years old)	Male	Essential hypertension	18633173	details
Blood	Detected and Quantified	22.7 +/- 6.2 uM	Adult (>18 years old)	Female	Essential hypertension	18633173	details
Blood	Detected and Quantified	24.8 +/- 13.3 uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	27329611	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	0.49 +/- 0.46 umol/mmol creatinine	Adult (>18 years old)	Female	Thyroid cancer	14643447	details

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. doi: 10.1291/hypres.31.623. [PubMed:18633173 ]
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. doi: 10.1291/hypres.31.623. [PubMed:18633173 ]
Major depressive disorder
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
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
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 ] 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 ] 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
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

145500 (Hypertension)
608516 (Major depressive disorder)
243500 (Isovaleric acidemia)
114500 (Colorectal cancer)

External Links

DrugBank ID

DB00132

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

27432

Food Biomarker Ontology

Not Available

VMH ID

LNLNCA

MarkerDB ID

MDB00000318

Good Scents ID

Not Available

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

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Calcium-dependent phospholipase A2

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 acid	details

Enzyme Details

2. Group IIF secretory phospholipase A2

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 acid	details

Enzyme Details

3. Cytosolic phospholipase A2

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 acid	details

Enzyme Details

4. Phospholipase A2

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 acid	details

Enzyme Details

5. Group XIIB secretory phospholipase A2-like protein

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 acid	details

Enzyme Details

6. Group 10 secretory phospholipase A2

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 acid	details

Enzyme Details

7. Group IIE secretory phospholipase A2

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 acid	details

Enzyme Details

8. Group XIIA secretory phospholipase A2

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 acid	details

Enzyme Details

9. 85/88 kDa calcium-independent phospholipase A2

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 acid	details

Enzyme Details

10. Phospholipase A2, membrane associated

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 acid	details

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

Show all enzymes and transporters

Showing metabocard for alpha-Linolenic acid (HMDB0001388)

MOL for HMDB0001388 (alpha-Linolenic acid)

3D MOL for HMDB0001388 (alpha-Linolenic acid)

3D SDF for HMDB0001388 (alpha-Linolenic acid)

3D-SDF for HMDB0001388 (alpha-Linolenic acid)

PDB for HMDB0001388 (alpha-Linolenic acid)

3D PDB for HMDB0001388 (alpha-Linolenic acid)

SMILES for HMDB0001388 (alpha-Linolenic acid)

INCHI for HMDB0001388 (alpha-Linolenic acid)

Structure for HMDB0001388 (alpha-Linolenic acid)

3D Structure for HMDB0001388 (alpha-Linolenic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions