MiMeDB: Showing metabocard for alpha-Linolenic acid (MMDBc0000190)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:39:10 UTC

Update Date

2024-09-29 08:01:15 UTC

Metabolite ID

MMDBc0000190

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>
MMDBc0000190

> <DATABASE_NAME>
MIME

> <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

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	MeSH
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

Molecular Formula

C₁₈H₃₀O₂

Average Mass

278.4296

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Adipose Tissue
Blood
Epidermis
Feces
Fibroblasts
Intestine
Placenta
Platelet
Prostate
Skeletal Muscle
Urine

Tissue Locations

Adipose Tissue
Epidermis
Fibroblasts
Intestine
Placenta
Platelet
Prostate
Skeletal Muscle

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191732	Calcium-dependent phospholipase A2	Unknown	P39877	Homo sapiens
MMDBp0191733	Group IIF secretory phospholipase A2	Unknown	Q9BZM2	Homo sapiens
MMDBp0191734	Cytosolic phospholipase A2	Unknown	P47712	Homo sapiens
MMDBp0191735	Phospholipase A2	Unknown	P04054	Homo sapiens
MMDBp0191736	Group XIIB secretory phospholipase A2-like protein	Unknown	Q9BX93	Homo sapiens
MMDBp0191737	Group 10 secretory phospholipase A2	Unknown	O15496	Homo sapiens
MMDBp0191739	Group IIE secretory phospholipase A2	Unknown	Q9NZK7	Homo sapiens
MMDBp0191741	Group XIIA secretory phospholipase A2	Unknown	Q9BZM1	Homo sapiens
MMDBp0191742	85/88 kDa calcium-independent phospholipase A2	Unknown	O60733	Homo sapiens
MMDBp0191745	Phospholipase A2, membrane associated	Unknown	P14555	Homo sapiens
MMDBp0191746	Group IID secretory phospholipase A2	Unknown	Q9UNK4	Homo sapiens
MMDBp0192178	Cytosolic phospholipase A2 gamma	Unknown	Q9UP65	Homo sapiens
MMDBp0192181	Group 3 secretory phospholipase A2	Unknown	Q9NZ20	Homo sapiens
MMDBp0192196	Bile acid-CoA:amino acid N-acyltransferase	Enzyme	Q14032	Homo sapiens
MMDBp0192655	Cytosolic acyl coenzyme A thioester hydrolase	Enzyme	O00154	Homo sapiens
MMDBp0192656	Acyl-coenzyme A thioesterase 2, mitochondrial	Enzyme	P49753	Homo sapiens
MMDBp0192657	Acyl-coenzyme A thioesterase 4	Enzyme	Q8N9L9	Homo sapiens
MMDBp0192658	Acyl-coenzyme A thioesterase 8	Enzyme	O14734	Homo sapiens
MMDBp0193461	Transient receptor potential cation channel subfamily V member 1	Unknown	Q8NER1	Homo sapiens
MMDBp0193627	Fatty acid desaturase 1	Unknown	O60427	Homo sapiens
MMDBp0193782	Sodium/calcium exchanger 1	Unknown	P32418	Homo sapiens
MMDBp0193876	Fatty acid desaturase 2	Unknown	O95864	Homo sapiens
MMDBp0193978	Elongation of very long chain fatty acids protein 4	Enzyme	Q9GZR5	Homo sapiens
MMDBp0194097	Phospholipase B1, membrane-associated	Unknown	Q6P1J6	Homo sapiens
MMDBp0194634	Cytosolic phospholipase A2 delta	Unknown	Q86XP0	Homo sapiens
MMDBp0194635	Cytosolic phospholipase A2 epsilon	Unknown	Q3MJ16	Homo sapiens
MMDBp0194636	Cytosolic phospholipase A2 zeta	Unknown	Q68DD2	Homo sapiens
MMDBp0195865	Cytosolic phospholipase A2 beta	Unknown	P0C869	Homo sapiens
MMDBp0196516	Acyl-coenzyme A thioesterase 1	Enzyme	Q86TX2	Homo sapiens
MMDBp0196846	HRAS-like suppressor 3	Unknown	P53816

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0036183	PC(16:0/18:3(9Z,12Z,15Z))	alpha-Linolenic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036184	PC(16:1(9Z)/18:3(9Z,12Z,15Z))	alpha-Linolenic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036185	PC(18:0/18:3(9Z,12Z,15Z))	alpha-Linolenic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036186	PC(18:1(11Z)/18:3(9Z,12Z,15Z))	alpha-Linolenic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036187	PC(18:1(9Z)/18:3(9Z,12Z,15Z))	alpha-Linolenic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036188	PC(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))	alpha-Linolenic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036189	PC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))	alpha-Linolenic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036190	PC(20:0/18:3(9Z,12Z,15Z))	alpha-Linolenic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036191	PC(20:1(11Z)/18:3(9Z,12Z,15Z))	alpha-Linolenic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036192	PC(20:2(11Z,14Z)/18:3(9Z,12Z,15Z))	alpha-Linolenic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036193	PC(20:3(5Z,8Z,11Z)/18:3(9Z,12Z,15Z))	alpha-Linolenic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036194	PC(20:3(8Z,11Z,14Z)/18:3(9Z,12Z,15Z))	alpha-Linolenic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036195	PC(22:0/18:3(9Z,12Z,15Z))	alpha-Linolenic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036196	PC(22:1(13Z)/18:3(9Z,12Z,15Z))	alpha-Linolenic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036197	PC(22:2(13Z,16Z)/18:3(9Z,12Z,15Z))	alpha-Linolenic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036198	PC(24:1(15Z)/18:3(9Z,12Z,15Z))	alpha-Linolenic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036199	PC(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))	alpha-Linolenic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036658	PC(18:3(9Z,12Z,15Z)/16:0)	alpha-Linolenic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036659	PC(18:3(9Z,12Z,15Z)/16:1(9Z))	alpha-Linolenic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036660	PC(18:3(9Z,12Z,15Z)/18:0)	alpha-Linolenic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036661	PC(18:3(9Z,12Z,15Z)/18:1(11Z))	alpha-Linolenic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036662	PC(18:3(9Z,12Z,15Z)/18:1(9Z))	alpha-Linolenic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036663	PC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z))	alpha-Linolenic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036664	PC(18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z))	alpha-Linolenic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036665	PC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))	alpha-Linolenic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036666	PC(18:3(9Z,12Z,15Z)/20:1(11Z))	alpha-Linolenic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036667	PC(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))	alpha-Linolenic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036668	PC(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))	alpha-Linolenic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036669	PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))	alpha-Linolenic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036670	PC(18:3(9Z,12Z,15Z)/22:0)	alpha-Linolenic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036671	PC(18:3(9Z,12Z,15Z)/22:1(13Z))	alpha-Linolenic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036672	PC(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))	alpha-Linolenic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036673	PC(18:3(9Z,12Z,15Z)/24:1(15Z))	alpha-Linolenic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036674	PC(18:3(9Z,12Z,15Z)/20:0)	alpha-Linolenic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0038257	MG(18:3(9Z,12Z,15Z)/0:0/0:0)	Glycerol	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0038701	alpha-Linolenic acid	Alpha-Linolenoyl-CoA	Long-chain-fatty-acid--CoA ligase 1	Hydrolysis; Ligation	RHEA	34755880
MMDBr0038834	Alpha-Linolenoyl-CoA	alpha-Linolenic acid	Thioesterase TesA	Hydrolysis	RHEA	34755880
MMDBr0038930	alpha-Linolenic acid	N-[(9Z,12Z,15Z)-Octadeca-9,12,15-trienoyl]-4R-hydroxysphinganine	Alkaline ceramidase YPC1	Hydrolysis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Essential hypertension		Association	Human Blood	HMDB	18633173
Hypertension		Association	Human Blood	HMDB	18633173
Isovaleric acidemia	Slight Decrease	Association	Human Blood	HMDB	27329611
Major depressive disorder		Association	Human Blood	HMDB	21185973
Thyroid cancer	Slight Decrease	Association	Human Urine	HMDB	14643447

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Firmicutes	1	Human ; Human feces; Human saliva; Human mucosa	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Cyanobacteria	1
Bacteria/Eubacteria	Proteobacteria	1	Human ; Human sputum; Human subgingival plaque; Human feces
Bacteria/Eubacteria	Actinobacteria	1	Human
Eukaryota/Fungi	Ascomycota	6

Exposure Sources

Food Exposures

Source Type	Source Sub-type	Source Name	Data Source	Reference
Animal	Not Available	Agar	FooDB	DTU
Animal	Not Available	Anguilliformes	FooDB	DTU
Animal	Not Available	Atlantic halibut	FooDB	DTU
Animal	Not Available	Atlantic salmon	FooDB	34893796
Animal	Not Available	Atlantic wolffish	FooDB	DTU
Animal	Not Available	Burbot	FooDB	DTU
Animal	Not Available	Carp bream	FooDB	DTU
Animal	Not Available	Channel catfish	FooDB	34893796
Animal	Not Available	Charr	FooDB	DTU
Animal	Not Available	Chicken	FooDB	DTU
Animal	Not Available	Cichlidae (tilapia)	FooDB	34893796
Animal	Not Available	Clawed lobster	FooDB	DTU
Animal	Not Available	Clupeinae (herring, sardine, sprat)	FooDB	DTU
Animal	Not Available	Coho salmon	FooDB	34893796
Animal	Not Available	Common dab	FooDB	DTU
Animal	Not Available	Common octopus	FooDB	DTU
Animal	Not Available	Crab	FooDB	DTU
Animal	Not Available	Crayfish	FooDB	DTU
Animal	Not Available	Flatfish	FooDB	DTU
Animal	Not Available	Gadiformes	FooDB	DTU
Animal	Not Available	Gadus (common cod)	FooDB	DTU
Animal	Not Available	Garfish	FooDB	DTU
Animal	Not Available	Greenland halibut/turbot	FooDB	DTU
Animal	Not Available	Haddock	FooDB	DTU
Animal	Not Available	Hippoglossus (common halibut)	FooDB	34893796
Animal	Not Available	Kombu	FooDB	DTU
Animal	Not Available	Lake trout	FooDB	DTU
Animal	Not Available	Lemon sole	FooDB	DTU
Animal	Not Available	Lumpsucker	FooDB	DTU
Animal	Not Available	Marine mussel	FooDB	DTU
Animal	Not Available	Mountain hare	FooDB	DTU
Animal	Not Available	Northern pike	FooDB	DTU
Animal	Not Available	Norway lobster	FooDB	DTU
Animal	Not Available	Norway pout	FooDB	DTU
Animal	Not Available	Orange roughy	FooDB	34893796
Animal	Not Available	Pacific ocean perch	FooDB	DTU
Animal	Not Available	Perciformes	FooDB	DTU
Animal	Not Available	Pikeperch	FooDB	DTU
Animal	Not Available	Pleuronectidae (dab, halibut, plaice)	FooDB	DTU
Animal	Not Available	Pollock	FooDB	DTU
Animal	Not Available	Rainbow trout	FooDB	DTU
Animal	Not Available	Salmonidae (salmon, trout)	FooDB	DTU
Animal	Not Available	Scombridae (bonito, mackerel, tuna)	FooDB	DTU
Animal	Not Available	Shrimp	FooDB	DTU
Animal	Not Available	Snail	FooDB	DTU
Animal	Not Available	Spiny dogfish	FooDB	DTU
Animal	Not Available	Sturgeon	FooDB	DTU
Animal	Not Available	Thunnus	FooDB	DTU
Animal	Not Available	Turbot	FooDB	DTU
Animal	Not Available	Whitefish	FooDB	DTU
Animal	Not Available	Whiting	FooDB	DTU
Plant	Not Available	Allium	FooDB	DTU
Plant	Not Available	Almond	FooDB	DTU
Plant	Not Available	Amaranth	FooDB	34893796
Plant	Not Available	Arabica coffee	FooDB	DTU
Plant	Not Available	Beer	FooDB	DTU
Plant	Not Available	Black salsify	FooDB	DTU
Plant	Not Available	Black walnut	FooDB	DTU
Plant	Not Available	Brandy	FooDB	DTU
Plant	Not Available	Broccoli	FooDB	DTU
Plant	Not Available	Brussel sprouts	FooDB	DTU
Plant	Not Available	Cassava	FooDB	DTU
Plant	Not Available	Cauliflower	FooDB	DTU
Plant	Not Available	Chanterelle	FooDB	DTU
Plant	Not Available	Cherimoya	FooDB	DTU
Plant	Not Available	Chervil	FooDB	DTU
Plant	Not Available	Chicory	FooDB	DTU
Plant	Not Available	Chinese cabbage	FooDB	DTU
Plant	Not Available	Chives	FooDB	DTU
Plant	Not Available	Cinnamon	FooDB	DTU
Plant	Not Available	Common cabbage	FooDB	DTU
Plant	Not Available	Common mushroom	FooDB	DTU
Plant	Not Available	Common pea	FooDB	DTU
Plant	Not Available	Dill	FooDB	DTU
Plant	Not Available	Endive	FooDB	DTU
Plant	Not Available	French plantain	FooDB	DTU
Plant	Not Available	Garden cress	FooDB	DTU
Plant	Not Available	Garden rhubarb	FooDB	DTU
Plant	Not Available	Garlic	FooDB	DTU
Plant	Not Available	Globe artichoke	FooDB	DTU
Plant	Not Available	Horseradish	FooDB	DTU
Plant	Not Available	Jerusalem artichoke	FooDB	DTU
Plant	Not Available	Kale	FooDB	DTU
Plant	Not Available	Kohlrabi	FooDB	DTU
Plant	Not Available	Lentils	FooDB	DTU
Plant	Not Available	Lettuce	FooDB	DTU
Plant	Not Available	Loquat	FooDB	DTU
Plant	Not Available	Nutmeg	FooDB	DTU
Plant	Not Available	Okra	FooDB	DTU
Plant	Not Available	Oyster mushroom	FooDB	DTU
Plant	Not Available	Pak choy	FooDB	DTU
Plant	Not Available	Papaya	FooDB	DTU
Plant	Not Available	Parsley	FooDB	DTU
Plant	Not Available	Parsnip	FooDB	DTU
Plant	Not Available	Pepper (spice)	FooDB	DTU
Plant	Not Available	Potato	FooDB	DTU
Plant	Not Available	Red wine	FooDB	DTU
Plant	Not Available	Robusta coffee	FooDB	DTU
Plant	Not Available	Romaine lettuce	FooDB	DTU
Plant	Not Available	Rose wine	FooDB	DTU
Plant	Not Available	Round kumquat	FooDB	DTU
Plant	Not Available	Savoy cabbage	FooDB	DTU
Plant	Not Available	Sorrel	FooDB	DTU
Plant	Not Available	Soy bean	FooDB	DTU
Plant	Not Available	Spinach	FooDB	DTU
Plant	Not Available	Swede	FooDB	DTU
Plant	Not Available	Sweet potato	FooDB	DTU
Plant	Not Available	Swiss chard	FooDB	DTU
Plant	Not Available	Teff	FooDB	34893796
Plant	Not Available	Turnip	FooDB	DTU
Plant	Not Available	Watercress	FooDB	DTU
Plant	Not Available	Whisky	FooDB	DTU
Plant	Not Available	White cabbage	FooDB	DTU
Plant	Not Available	White wine	FooDB	DTU
Plant	Not Available	Wild celery	FooDB	DTU
Plant	Not Available	Wild leek	FooDB	DTU
Plant	Bean	Common bean	FooDB	DTU
Plant	Bean sprout	Common bean	FooDB	DTU
Plant	Bean sprout	Mung bean	FooDB	DTU
Animal	Brain	Cow	FooDB	34893796
Plant	Cocoa products	Cocoa bean	FooDB	DTU
Plant	Coffee	Arabica coffee	FooDB	DTU
Plant	Coffee	Robusta coffee	FooDB	DTU
Plant	Cotyledon	Cucumber	FooDB	DUKE
Plant	Cotyledon	Muskmelon	FooDB	DUKE
Animal	Egg	Anser	FooDB	DTU
Animal	Egg	Chicken	FooDB	DTU
Animal	Egg	Mallard duck	FooDB	DTU
Animal	Fat	Anser	FooDB	DTU
Animal	Fat	Cow	FooDB	DTU
Animal	Fat	Domestic pig	FooDB	DTU
Animal	Fat	Wild boar	FooDB	DTU
Animal	Fillet	Blue whiting	FooDB	DTU
Animal	Fillet	Catfish	FooDB	DTU
Animal	Fillet	Common ling	FooDB	DTU
Animal	Fillet	Gadus (common cod)	FooDB	DTU
Animal	Fillet	Norway haddock	FooDB	DTU
Animal	Fillet	Pollock	FooDB	DTU
Animal	Fllet	Gadus (common cod)	FooDB	DTU
Plant	Flour	Potato	FooDB	DTU
Plant	Flour	Soy bean	FooDB	DTU
Plant	Fruit	Apple	FooDB	DTU
Plant	Fruit	Apricot	FooDB	DTU
Plant	Fruit	Avocado	FooDB	DTU
Plant	Fruit	Bilberry	FooDB	DTU
Plant	Fruit	Blackcurrant	FooDB	DTU
Plant	Fruit	Chayote	FooDB	DTU
Plant	Fruit	Cherimoya	FooDB	DUKE
Plant	Fruit	Coconut	FooDB	DTU
Plant	Fruit	Common bean	FooDB	DUKE
Plant	Fruit	Common grape	FooDB	DUKE
Plant	Fruit	Common pea	FooDB	DUKE
Plant	Fruit	Cucumber	FooDB	DTU
Plant	Fruit	Cucurbita	FooDB	DTU
Plant	Fruit	Date	FooDB	DTU
Plant	Fruit	Eggplant	FooDB	DTU
Plant	Fruit	Elderberry	FooDB	DTU
Plant	Fruit	European plum	FooDB	DTU
Plant	Fruit	Fig	FooDB	DTU
Plant	Fruit	Garden tomato	FooDB	DTU
Plant	Fruit	Garden tomato (var.)	FooDB	DUKE
Plant	Fruit	Gooseberry	FooDB	DTU
Plant	Fruit	Grape	FooDB	DTU
Plant	Fruit	Grapefruit	FooDB	DTU
Plant	Fruit	Green zucchini	FooDB	DTU
Plant	Fruit	Groundcherry	FooDB	DTU
Plant	Fruit	Guava	FooDB	DTU
Plant	Fruit	Kiwi	FooDB	DTU
Plant	Fruit	Lemon	FooDB	DTU
Plant	Fruit	Lichee	FooDB	DTU
Plant	Fruit	Lime	FooDB	DTU
Plant	Fruit	Lingonberry	FooDB	DTU
Plant	Fruit	Loganberry	FooDB	DTU
Plant	Fruit	Malus (crab apple)	FooDB	DTU
Plant	Fruit	Mandarin orange (clementine, tangerine)	FooDB	DTU
Plant	Fruit	Mango	FooDB	DTU
Plant	Fruit	Muskmelon	FooDB	DTU
Plant	Fruit	Nectarine	FooDB	DTU
Plant	Fruit	Papaya	FooDB	DUKE
Plant	Fruit	Passion fruit	FooDB	DTU
Plant	Fruit	Peach	FooDB	DTU
Plant	Fruit	Pear	FooDB	DTU
Plant	Fruit	Pepper	FooDB	DTU
Plant	Fruit	Pepper (c. frutescens)	FooDB	DUKE
Plant	Fruit	Pepper (spice)	FooDB	DUKE
Plant	Fruit	Persimmon	FooDB	DTU
Plant	Fruit	Pineapple	FooDB	DTU
Plant	Fruit	Pomegranate	FooDB	DTU
Plant	Fruit	Prickly pear	FooDB	DTU
Plant	Fruit	Prunus (cherry, plum)	FooDB	DTU
Plant	Fruit	Quince	FooDB	DTU
Plant	Fruit	Redcurrant	FooDB	DTU
Plant	Fruit	Rose hip	FooDB	DTU
Plant	Fruit	Sour cherry	FooDB	DUKE
Plant	Fruit	Star fruit	FooDB	DTU
Plant	Fruit	Strawberry	FooDB	DTU
Plant	Fruit	Strawberry guava	FooDB	DUKE
Plant	Fruit	Sunburst squash (pattypan squash)	FooDB	DTU
Plant	Fruit	Sweet orange	FooDB	DTU
Plant	Fruit	Tamarind	FooDB	DTU
Plant	Fruit	Vaccinium (blueberry, cranberry, huckleberry)	FooDB	DTU
Plant	Fruit	Watermelon	FooDB	DTU
Plant	Fruit	Winter squash	FooDB	DTU
Plant	Fruit	Yardlong bean	FooDB	DUKE
Animal	Hand	Pig	FooDB	DTU
Animal	Hand with rind	Pig	FooDB	DTU
Animal	Heart	Chicken	FooDB	DTU
Animal	Heart	Cow	FooDB	DTU
Animal	Heart	Pig	FooDB	DTU
Plant	Herb	Purslane	FooDB	DUKE
Animal	Hind leg without rind	Pig	FooDB	DTU
Plant	Juice	Blackcurrant	FooDB	DTU
Plant	Juice	Elderberry	FooDB	DTU
Plant	Juice	Grape	FooDB	DTU
Plant	Juice	Lemon	FooDB	DTU
Plant	Juice	Prunus (cherry, plum)	FooDB	DTU
Plant	Juice	Strawberry	FooDB	DTU
Animal	Kidney	Cow	FooDB	DTU
Animal	Kidney	Pig	FooDB	DTU
Plant	Leaves	Brussel sprouts	FooDB	DUKE
Plant	Leaves	Cabbage	FooDB	DUKE
Plant	Leaves	Celery leaves	FooDB	DTU
Plant	Leaves	Chicory	FooDB	DUKE
Plant	Leaves	Chives	FooDB	DUKE
Plant	Leaves	Coriander	FooDB	DTU
Plant	Leaves	Dandelion	FooDB	DTU
Plant	Leaves	Endive	FooDB	DUKE
Plant	Leaves	Garden cress	FooDB	DUKE
Plant	Leaves	Jute	FooDB	DUKE
Plant	Leaves	Lettuce	FooDB	DUKE
Plant	Leaves	New zealand spinach	FooDB	DUKE
Plant	Leaves	Red beetroot	FooDB	DUKE
Plant	Leaves	Sorrel	FooDB	DUKE
Plant	Leaves	Taro	FooDB	DUKE
Plant	Leaves	Tea	FooDB	DTU
Plant	Leaves	White cabbage	FooDB	DUKE
Plant	Leaves	Winged bean	FooDB	DUKE
Animal	Leg	True frog	FooDB	DTU
Animal	Leg meat	Pig	FooDB	DTU
Animal	Leg with knuckle	Pig	FooDB	DTU
Animal	Liver	Chicken	FooDB	DTU
Animal	Liver	Cow	FooDB	DTU
Animal	Liver	Duck	FooDB	DTU
Animal	Liver	Gadus (common cod)	FooDB	DTU
Animal	Liver	Goose	FooDB	DTU
Animal	Liver	Pig	FooDB	DTU
Animal	Meat and skin	Chicken	FooDB	DTU
Animal	Meat and skin	Duck	FooDB	DTU
Animal	Meat and skin	Goose	FooDB	DTU
Animal	Meat and skin	Pig	FooDB	DTU
Animal	Meat and skin	Turkey	FooDB	DTU
Animal	Milk	Cow	FooDB	16899705
Animal	Milk	Domestic goat	FooDB	DTU
Animal	Milk	Human	FooDB	DTU
Animal	Neck	Pig	FooDB	DTU
Plant	Nut	Brazil nut	FooDB	DTU
Plant	Nut	Chestnut	FooDB	DTU
Plant	Nut	Hazelnut	FooDB	DTU
Plant	Nut	Peanut	FooDB	DTU
Plant	Nut	Pecan nut	FooDB	DTU
Plant	Nut	Pine nut	FooDB	DTU
Plant	Nut	Pistachio	FooDB	DTU
Animal	Oil	Gadus (common cod)	FooDB	DTU
Animal	Oil	Haddock	FooDB	DTU
Plant	Oil	Coconut	FooDB	DTU
Plant	Oil	Cottonseed	FooDB	DTU
Plant	Oil	Flaxseed	FooDB	DTU
Plant	Oil	Oil palm	FooDB	DTU
Plant	Oil	Olive	FooDB	DTU
Plant	Oil	Peanut	FooDB	DTU
Plant	Oil	Rape	FooDB	DTU
Plant	Oil	Safflower	FooDB	DTU
Plant	Oil	Sesame	FooDB	DTU
Plant	Oil	Soy bean	FooDB	DTU
Plant	Oil	Sunflower	FooDB	DTU
Plant	Oil	Thistle	FooDB	DTU
Plant	Oil	Walnut	FooDB	DTU
Plant	Peel	Lemon	FooDB	DTU
Plant	Plant	Common oregano	FooDB	DUKE
Plant	Plant	Common thyme	FooDB	DUKE
Plant	Plant	Spinach	FooDB	DUKE
Plant	Powder	Garlic	FooDB	DTU
Plant	Powder	Rose hip	FooDB	DTU
Plant	Rhizome	Sacred lotus	FooDB	DUKE
Animal	Rib	Pig	FooDB	DTU
Animal	Roe	Gadus (common cod)	FooDB	DTU
Plant	Root	Burdock	FooDB	DUKE
Plant	Root	Carrot	FooDB	DTU
Plant	Root	Cassava	FooDB	DUKE
Plant	Root	Chicory	FooDB	DUKE
Plant	Root	Daikon radish	FooDB	DTU
Plant	Root	Fennel	FooDB	DTU
Plant	Root	Ginger	FooDB	DTU
Plant	Root	Horseradish	FooDB	DTU
Plant	Root	Mountain yam	FooDB	DUKE
Plant	Root	Parsley	FooDB	DTU
Plant	Root	Parsnip	FooDB	DUKE
Plant	Root	Radish	FooDB	DUKE
Plant	Root	Red beetroot	FooDB	DTU
Plant	Root	Sweet potato	FooDB	DUKE
Plant	Root	Taro	FooDB	DUKE
Plant	Root	Wild carrot	FooDB	DUKE
Plant	Seed	Adzuki bean	FooDB	DTU
Plant	Seed	Alfalfa	FooDB	DTU
Plant	Seed	Almond	FooDB	DUKE
Plant	Seed	Arabica coffee	FooDB	DUKE
Plant	Seed	Brazil nut	FooDB	DUKE
Plant	Seed	Breadfruit	FooDB	DUKE
Plant	Seed	Broad bean	FooDB	DUKE
Plant	Seed	Butternut	FooDB	DUKE
Plant	Seed	Caraway	FooDB	DUKE
Plant	Seed	Carrot	FooDB	DUKE
Plant	Seed	Cashew nut	FooDB	DUKE
Plant	Seed	Chickpea	FooDB	DTU
Plant	Seed	Colorado pinyon	FooDB	DUKE
Plant	Seed	Common bean	FooDB	DTU
Plant	Seed	Common pea	FooDB	DTU
Plant	Seed	Common sage	FooDB	DUKE
Plant	Seed	Common walnut	FooDB	DUKE
Plant	Seed	Coriander	FooDB	DTU
Plant	Seed	Dill	FooDB	DUKE
Plant	Seed	Fennel	FooDB	DTU
Plant	Seed	Fig	FooDB	DUKE
Plant	Seed	Flaxseed	FooDB	DTU
Plant	Seed	Garden cress	FooDB	DUKE
Plant	Seed	Ginkgo nuts	FooDB	DUKE
Plant	Seed	Gram bean	FooDB	DUKE
Plant	Seed	Guava	FooDB	DUKE
Plant	Seed	Hyacinth bean	FooDB	DUKE
Plant	Seed	Jute	FooDB	DUKE
Plant	Seed	Lentils	FooDB	DUKE
Plant	Seed	Moth bean	FooDB	DUKE
Plant	Seed	Mung bean	FooDB	DTU
Plant	Seed	Passion fruit	FooDB	DUKE
Plant	Seed	Peanut	FooDB	DUKE
Plant	Seed	Pigeon pea	FooDB	DUKE
Plant	Seed	Pistachio	FooDB	DUKE
Plant	Seed	Poppy	FooDB	DTU
Plant	Seed	Purslane	FooDB	DUKE
Plant	Seed	Sacred lotus	FooDB	DUKE
Plant	Seed	Safflower	FooDB	DUKE
Plant	Seed	Sea-buckthornberry	FooDB	DUKE
Plant	Seed	Sesame	FooDB	DTU
Plant	Seed	Soy bean	FooDB	DTU
Plant	Seed	Summer savory	FooDB	DUKE
Plant	Seed	Sunburst squash (pattypan squash)	FooDB	34893796
Plant	Seed	Sunflower	FooDB	DTU
Plant	Seed	Sweet marjoram	FooDB	DUKE
Plant	Seed	White lupine	FooDB	DUKE
Plant	Seed	White mustard	FooDB	DUKE
Plant	Seed	Wild carrot	FooDB	DUKE
Plant	Seed	Wild celery	FooDB	DUKE
Plant	Seed	Winged bean	FooDB	DUKE
Plant	Seed	Winter squash	FooDB	34893796
Plant	Seed	Yardlong bean	FooDB	DUKE
Plant	Seed	Yellow pond-lily	FooDB	34893796
Plant	Seed essential oil	Blackcurrant	FooDB	DUKE
Plant	Seed oil	Grape	FooDB	DTU
Plant	Shoot	Asparagus	FooDB	DTU
Plant	Shoot	Bamboo shoots	FooDB	DTU
Plant	Shoot	Celeriac	FooDB	DTU
Animal	Shoulder	Pig	FooDB	DTU
Plant	Sprout	Soy bean	FooDB	DTU
Plant	Sprout seedling	Common bean	FooDB	DUKE
Plant	Sprout seedling	Lentils	FooDB	DUKE
Plant	Sprout seedling	Mung bean	FooDB	DUKE
Plant	Stem	Kohlrabi	FooDB	DUKE
Animal	Thymus	Cow	FooDB	DTU
Animal	Thymus	Sheep (mutton, lamb)	FooDB	DTU
Animal	Tongue	Cow	FooDB	DTU
Animal	Tongue	Pig	FooDB	DTU
Animal	Tripe	Cow	FooDB	34893796
Plant	Tuber	Potato	FooDB	DUKE
Plant	Tuber	Winged bean	FooDB	DUKE
Plant	Tuber	Yam	FooDB	DTU
Animal	Meat	See All	FooDB	DTU

Source Type	Source Sub-type	Source Name	Data Source	Reference
Animal	Meat	Chicken	FooDB	DTU
Animal	Meat	Cow	FooDB	DTU
Animal	Meat	Crab	FooDB	DTU
Animal	Meat	Duck	FooDB	DTU
Animal	Meat	Goose	FooDB	DTU
Animal	Meat	Pig	FooDB	DTU
Animal	Meat	Rabbit	FooDB	DTU
Animal	Meat	Rock ptarmigan	FooDB	DTU
Animal	Meat	Sheep (mutton, lamb)	FooDB	DTU
Animal	Meat	Squab	FooDB	DTU
Animal	Meat	Turkey	FooDB	DTU

Other Exposures

Source Type	Data Source	Reference
General Exposome	U.S. Environmental Protection Agency	CompTox
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	20.5	7.5	uM	Adult (>18 years old)	Male	Essential hypertension	HMDB	18633173
Human Blood	Detected and Quantified	22.7	6.2	uM	Adult (>18 years old)	Female	Essential hypertension	HMDB	18633173
Human Blood	Detected and Quantified	21.2	7.2	uM	Adult (>18 years old)	Both	Hypertension	HMDB	18633173
Human Blood	Detected and Quantified	24.8	13.3	uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	HMDB	27329611
Human Blood	Detected and Quantified	66.803	30.169	uM	Adult (>18 years old)	Both	Depression	HMDB	21185973
Human Urine	Detected and Quantified	0.49	0.46	umol/mmol creatinine	Adult (>18 years old)	Female	Thyroid cancer	HMDB	14643447
Human Blood	Detected and Quantified	0.115	0.004	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Urine	Detected and Quantified	0.73	0.54	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	14643447
Human Blood	Detected and Quantified	1.975	1.223	uM	Adult (>18 years old)	Both	Normal	HMDB	18953024
Human Blood	Detected and Quantified	1.975	1.223	uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	10.775	3.592	uM	Adult (>18 years old)	Male	Normal	HMDB	17069347
Human Blood	Detected and Quantified	10.775	3.592	uM	Adult (>18 years old)	Male	Normal	HMDB	17069347
Human Blood	Detected and Quantified	100	40	uM	Adult (>18 years old)	Male	Normal	HMDB	14608088
Human Blood	Detected and Quantified	16.8	7.3	uM	Adult (>18 years old)	Male	Normal	HMDB	18633173
Human Blood	Detected and Quantified	17.5	7.6	uM	Adult (>18 years old)	Both	Normal	HMDB	18633173
Human Blood	Detected and Quantified	18.5	7.9	uM	Adult (>18 years old)	Both	Normal	HMDB	18633173
Human Blood	Detected and Quantified	5.11	3.8	uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	5.962	3.0528	uM	Adult (>18 years old)	Both	Normal	HMDB	17313719
Human Blood	Detected and Quantified	7.183	3.592	uM	Adult (>18 years old)	Male	Normal	HMDB	17069347
Human Blood	Detected and Quantified	7.183	35.916	uM	Adult (>18 years old)	Male	Normal	HMDB	17069347
Human Blood	Detected and Quantified	72.191	31.606	uM	Adult (>18 years old)	Both	Normal	HMDB	21185973
Human Blood	Detected and Quantified	73.0	45.6	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	27329611
Human Blood	Detected and Quantified	79.0146	33.0425	uM	Adult (>18 years old)	Both	Normal	HMDB	21185973
Human Blood	Detected and Quantified	8.548	3.771	uM	Adult (>18 years old)	Female	Normal	HMDB	9368807
Human Blood	Detected and Quantified	80	30	uM	Adult (>18 years old)	Female	Normal	HMDB	14608088
Human Blood	Detected and Quantified	1.1	0.8	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Adipose tissue	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified				Infant (0-1 year old)	Both	Normal	HMDB	22411374
Human Feces	Detected but not Quantified				Infant (0-1 year old)	NULL	Normal	HMDB	24628373
Human Feces	Detected but not Quantified				Infant (0-1 year old)	Not Specified	Normal	HMDB	24628373
Human Feces	Detected but not Quantified				Infant (0-1 year old)	Not Specified	Normal	HMDB	24628373
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0001388

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

References

Synthesis Reference

Not Available

General References

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 ]
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 ]
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. doi: 10.1093/ajcn/61.1.62. [PubMed:7825540 ]
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 ]
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 ]
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. doi: 10.1007/BF00714336. [PubMed:8717442 ]
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. doi: 10.1093/ajcn/69.5.872. [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. doi: 10.1016/s0378-5173(99)00013-7. [PubMed:10370194 ]
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. doi: 10.1038/sj.ejcn.1600785. [PubMed:10452408 ]
Connor WE: Importance of n-3 fatty acids in health and disease. Am J Clin Nutr. 2000 Jan;71(1 Suppl):171S-5S. doi: 10.1093/ajcn/71.1.171S. [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. doi: 10.1093/emboj/19.8.1784. [PubMed:10775263 ]
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. doi: 10.1054/plef.2000.0216. [PubMed:11090255 ]
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. doi: 10.1093/ajcn/73.2.209. [PubMed:11157315 ]
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 ]
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. doi: 10.1161/01.cir.0000038493.65177.94. [PubMed:12438303 ]
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. doi: 10.1161/01.CIR.0000058165.81208.C6. Epub 2003 Mar 10. [PubMed:12668490 ]
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. doi: 10.1097/01.ju.0000116544.09581.55. [PubMed:15017185 ]
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. doi: 10.1093/jn/134.4.919. [PubMed:15051847 ]
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. doi: 10.1081/pdt-49679. [PubMed:15776817 ]
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. doi: 10.2337/diabetes.54.11.3148. [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. doi: 10.1111/j.1464-410X.2006.05951.x. [PubMed:16430627 ]
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 ]

Showing metabocard for alpha-Linolenic acid (MMDBc0000190)

MOL for #<Metabolite:0x00005645c9e9fbf0>

3D MOL for #<Metabolite:0x00005645c9e9fbf0>

3D SDF for #<Metabolite:0x00005645c9e9fbf0>

3D-SDF for #<Metabolite:0x00005645c9e9fbf0>

PDB for #<Metabolite:0x00005645c9e9fbf0>

3D PDB for #<Metabolite:0x00005645c9e9fbf0>

SMILES for #<Metabolite:0x00005645c9e9fbf0>

INCHI for #<Metabolite:0x00005645c9e9fbf0>

Structure for #<Metabolite:0x00005645c9e9fbf0>

3D Structure for #<Metabolite:0x00005645c9e9fbf0>