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	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

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

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-052f-7900000000-8765cf82603feb1b448f	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-004i-9300000000-302519a616eaed5fcc59	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-005c-9800000000-2d44b3c70e2992b9a812	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-052f-7900000000-8765cf82603feb1b448f	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-9300000000-302519a616eaed5fcc59	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-005c-9800000000-2d44b3c70e2992b9a812	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-052f-5900000000-28710ea35f196c595e03	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052e-6950000000-27037263e74c8119ead0	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00ds-6931000000-657fa0cc66a206a36409	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-004i-0190000000-aee97e9ea2c7f0783adf	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-05nb-9500000000-fb92aefc701027239359	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0aru-9100000000-a5dddfe6f629d1371fac	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0090000000-2b7bea03a685454dd135	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0090000000-53ddfaed6ce13c37d957	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0090000000-e5350a66361bc63d1071	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004i-0090000000-5731aa5e301022c06813	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0091010000-6922411e48d747e592b5	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-001i-0090000000-a18b573ad888d048efa6	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0090000000-2b7bea03a685454dd135	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0090000000-e5350a66361bc63d1071	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0090000000-5731aa5e301022c06813	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-004i-0090000000-1d391027db3704d71cb9	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive	splash10-00lr-9210000000-41acd8a55f52afec6d79	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive	splash10-014i-9000000000-a976b4a80a07eb2c4641	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-497eddf5d738a45f83fb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-0c00ca98901526cb2e26	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-004i-1090000000-35ffce9343fe0d15ea0d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-004i-0090000000-373584fbab950d6676cc	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-0090000000-ae1f482177d0e208165e	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00o0-5690000000-20804c8382f14ff0ccf4	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-8930000000-9d5e342b1351adc71c20	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-4d3e8d1180800a7b4ed5	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0059-1090000000-67ab14c068a142dd3c30	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9230000000-403c610d63380e63109a	2017-07-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)		2012-12-05	View Spectrum

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	Data Source	Reference
MMDBr0001110	alpha-Linolenic acid	Alpha-Linolenoyl-CoA	Not Available	VMH	15292367
MMDBr0002887	Cholest-5-En-3Beta-Yl (9Z,12Z,15Z-Octadecatrienoate)	Cholesterol	carboxyl ester lipase	VMH	11230747 8112342
MMDBr0002902	alpha-Linolenic acid	Gamma-linolenoyl-CoA	Not Available	VMH	8584017
MMDBr0004522	alpha-Linolenic acid	Alpha-Linolenoyl-CoA	Not Available	VMH	10479480 9784915
MMDBr0009261	Alpha-Linolenoyl-CoA	alpha-Linolenic acid	acyl-CoA thioesterase 1	VMH	30371894
MMDBr0010214	Cholest-5-En-3Beta-Yl (9Z,12Z,15Z-Octadecatrienoate)	Cholesterol	carboxyl ester lipase	VMH; KEGG	30371894

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	Firmicutes	1	Human ; Human feces; Human saliva; Human mucosa	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Cyanobacteria	1
Bacteria	Proteobacteria	1	Human ; Human sputum; Human subgingival plaque; Human feces
Bacteria	Actinobacteria	1	Human
Eukaryota/Fungi	Ascomycota	6

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Neck	Domestic pig	FooDB	31437929
Animal		Salmo salar	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal		Astacidea	FooDB	31437929
Animal	Meat	Sheep	FooDB	31437929
Animal	Heart	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Egg	Gallus gallus	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Rib	Domestic pig	FooDB	31437929
Animal		Gadiformes	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Turkey	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Thymus	Cattle	FooDB	31437929
Animal	Meat and skin	Chicken	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Fat	Sus scrofa domestica	FooDB	31437929
Animal		Gadus	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Microstomus kitt	FooDB	31437929
Animal	Egg	Anas platyrhynchos	FooDB	31437929
Animal		Clupeinae	FooDB	31437929
Animal		Mytilidae	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Leg meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Mountain hare	FooDB	31437929
Animal	Meat	Rock ptarmigan	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Egg	Gallus gallus	FooDB	31437929
Animal		Hippoglossus hippoglossus	FooDB	31437929
Animal	Meat and skin	Chicken	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Squalus acanthias	FooDB	31437929
Animal	Kidney	Cattle	FooDB	31437929
Animal	Heart	Chicken	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Tongue	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Kidney	Domestic pig	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Leg	Ranidae	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Octopus vulgaris	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Sheep	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Oil	Melanogrammus aeglefinus	FooDB	31437929
Animal	Tripe	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Fillet	Sebastes viviparus	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Tongue	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Hand with rind	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Rib	Domestic pig	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Oil	Gadus	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat and skin	Chicken	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Abramis brama	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Clupeinae	FooDB	31437929
Animal	Egg	Anser sp.	FooDB	31437929
Animal		Microstomus kitt	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Pleuronectiformes	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Chicken	FooDB	31437929
Animal	Egg	Gallus gallus	FooDB	31437929
Animal		Cichlidae	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Liver	Cattle	FooDB	31437929
Animal	Meat	Sheep	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Anarhichas lupus	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Heart	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Tongue	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Liver	Cattle	FooDB	31437929
Animal	Meat	Sheep	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Scombridae	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Melanogrammus aeglefinus	FooDB	31437929
Animal	Rib	Domestic pig	FooDB	31437929
Animal	Meat		FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Tongue	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Hand	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Milk	Homo sapiens	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Fllet	Gadus	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Brain	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat		FooDB	31437929
Animal	Fat	Cattle	FooDB	31437929
Animal	Meat and skin	Chicken	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Salmonidae	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Fat	Anser sp.	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat and skin	Chicken	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Egg	Gallus gallus	FooDB	31437929
Animal	Meat	Sheep	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Tongue	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Heart	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Nephropidae	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Liver	Chicken	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Fillet	Molva molva	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Cichlidae	FooDB	31437929
Animal	Liver		FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Heart	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Hoplostethus atlanticus	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal		Pollachius	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Oncorhynchus mykiss	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Hand	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat and skin	Domestic pig	FooDB	31437929
Animal		Trisopterus esmarkii	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Fillet	Gadus	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Homo sapiens	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat and skin	Chicken	FooDB	31437929
Animal	Liver	Domestic pig	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal		Esox lucius	FooDB	31437929
Animal		Reinhardtius hippoglossoides	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Tripe	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal		Belone belone	FooDB	31437929
Animal		Salmonidae	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Liver	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Gastropoda	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Sheep	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Egg	Gallus gallus	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal		Merlangius merlangus	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Kidney	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Limanda limanda	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Nephropidae	FooDB	31437929
Animal	Meat	Pigeon	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Liver		FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Heart	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Scophthalmus maximus	FooDB	31437929
Animal	Shoulder	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Turkey	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Anguilliformes	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Fillet	Pollachius	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Liver	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Hand	Domestic pig	FooDB	31437929
Animal	Milk	Capra aegagrus hircus	FooDB	31437929
Animal		Caridea	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat and skin	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat and skin	Chicken	FooDB	31437929
Animal	Liver	Domestic pig	FooDB	31437929
Animal	Liver	Gadus	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Eucheuma	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Reinhardtius hippoglossoides	FooDB	31437929
Animal		Chicken	FooDB	31437929
Animal	Milk	Homo sapiens	FooDB	31437929
Animal	Meat and skin		FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Brachyura	FooDB	31437929
Animal	Liver	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Salvelinus	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Acipenseridae	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Oncorhynchus mykiss	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Sheep	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Egg	Gallus gallus	FooDB	31437929
Animal		Hippoglossus	FooDB	31437929
Animal		Thunnus	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Fillet	Micromesistius poutassou	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Liver	Cattle	FooDB	31437929
Animal		Oncorhynchus kisutch	FooDB	31437929
Animal	Fillet	Siluriformes	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Perciformes	FooDB	31437929
Animal	Meat	Pigeon	FooDB	31437929
Animal	Meat and skin	Domestic pig	FooDB	31437929
Animal		Nephrops norvegicus	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Thymus	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Neck	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat and skin	Turkey	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Clupeinae	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Fillet	Pollachius	FooDB	31437929
Animal		Saccharina japonica	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Kidney	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Liver	Domestic pig	FooDB	31437929
Animal	Hind leg without rind	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Egg	Gallus gallus	FooDB	31437929
Animal		Caridea	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat and skin	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Oncorhynchus mykiss	FooDB	31437929
Animal	Meat and skin	Chicken	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Liver	Cattle	FooDB	31437929
Animal	Meat and skin		FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Roe	Gadus	FooDB	31437929
Animal	Meat		FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal		Cyclopteridae	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Salvelinus namaycush	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Brachyura	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Acipenseridae	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Meat	Sheep	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal		Hippoglossus	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Egg	Gallus gallus	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Fat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Liver	Cattle	FooDB	31437929
Animal		Lota lota	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Ictalurus punctatus	FooDB	31437929
Animal	Thymus	Sheep	FooDB	31437929
Animal		Coregonus	FooDB	31437929
Animal	Meat and skin	Domestic pig	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Brain	Cattle	FooDB	31437929
Animal	Rib	Domestic pig	FooDB	31437929
Animal	Meat	Turkey	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Chicken	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Fat	Sus scrofa	FooDB	31437929
Animal		Mytilidae	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Clupeinae	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Fat	Cattle	FooDB	31437929
Animal	Thymus	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Leg with knuckle	Domestic pig	FooDB	31437929
Animal	Tongue	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat and skin	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Egg	Gallus gallus	FooDB	31437929
Animal		Oncorhynchus mykiss	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Chicken	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat		FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Kidney	Cattle	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Pleuronectidae	FooDB	31437929
Animal		Sebastes alutus	FooDB	31437929
Animal	Meat	Domestic pig	FooDB	31437929
Animal	Meat	Cattle	FooDB	31437929
Animal		Sander lucioperca	FooDB	31437929
Food			FooDB	31437929
Food			FooDB	31437929
Food	Cocoa products	Theobroma cacao	FooDB	31437929
Food	Cocoa products	Theobroma cacao	FooDB	31437929
Food	Cocoa products	Theobroma cacao	FooDB	31437929
Food			FooDB	31437929
Food			FooDB	31437929
Food	Cocoa products	Theobroma cacao	FooDB	31437929
Food			FooDB	31437929
Food	Cocoa products	Theobroma cacao	FooDB	31437929
Food			FooDB	31437929
Food			FooDB	31437929
Food	Cocoa products	Theobroma cacao	FooDB	31437929
Food			FooDB	31437929
Food	Coffee	Coffea arabica	FooDB	31437929
Food	Cocoa products	Theobroma cacao	FooDB	31437929
Food	Cocoa products	Theobroma cacao	FooDB	31437929
Food		Coffea arabica	FooDB	31437929
Food	Cocoa products	Theobroma cacao	FooDB	31437929
Food			FooDB	31437929
Food			FooDB	31437929
Food			FooDB	31437929
Food	Coffee	Coffea canephora	FooDB	31437929
Food	Cocoa products	Theobroma cacao	FooDB	31437929
Food	Cocoa products	Theobroma cacao	FooDB	31437929
Food			FooDB	31437929
Food			FooDB	31437929
Food	Cocoa products	Theobroma cacao	FooDB	31437929
Food		Coffea canephora	FooDB	31437929
Food	Cocoa products	Theobroma cacao	FooDB	31437929
Food			FooDB	31437929
Food	Cocoa products	Theobroma cacao	FooDB	31437929
Food	Cocoa products	Theobroma cacao	FooDB	31437929
Food			FooDB	31437929
Food			FooDB	31437929
Food	Cocoa products	Theobroma cacao	FooDB	31437929
Food			FooDB	31437929
Food	Cocoa products	Theobroma cacao	FooDB	31437929
Food	Cocoa products	Theobroma cacao	FooDB	31437929
Food	Cocoa products	Theobroma cacao	FooDB	31437929
Food			FooDB	31437929
Plant	Stem	Brassica oleracea var. gongylodes	FooDB	31437929
Plant	Fruit	Cucurbita pepo var. cylindrica	FooDB	31437929
Plant	Seed	Ficus carica	FooDB	31437929
Plant	Seed	Arachis hypogaea	FooDB	31437929
Plant	Seed	Vigna angularis	FooDB	31437929
Plant	Seed	Daucus carota	FooDB	31437929
Plant	Shoot	Asparagus officinalis	FooDB	31437929
Plant	Fruit	Ananas comosus	FooDB	31437929
Plant	Seed	Medicago sativa	FooDB	31437929
Plant		Brassica oleracea l. var. capitata l. f. alba dc.	FooDB	31437929
Plant	Fruit	Citrus sinensis	FooDB	31437929
Plant	Oil	Cocos nucifera	FooDB	31437929
Plant	Fruit	Fragaria x ananassa	FooDB	31437929
Plant	Fruit	Prunus persica	FooDB	31437929
Plant	Nut	Pinus	FooDB	31437929
Plant	Fruit	Cucurbita	FooDB	31437929
Plant	Seed	Foeniculum vulgare	FooDB	31437929
Plant	Fruit	Cucumis melo	FooDB	31437929
Plant	Root	Raphanus sativus var. longipinnatus	FooDB	31437929
Plant	Fruit	Vaccinium vitis-idaea	FooDB	31437929
Plant	Flower	Sambucus nigra	FooDB	31437929
Plant		Spinacia oleracea	FooDB	31437929
Plant	Fruit	Ribes rubrum	FooDB	31437929
Plant		Brassica oleracea	FooDB	31437929
Plant		Brassica oleracea var. botrytis	FooDB	31437929
Plant	Fruit	Sambucus	FooDB	31437929
Plant		Cantharellus cibarius	FooDB	31437929
Plant	Fruit	Capsicum annuum	FooDB	31437929
Plant	Nut	Corylus	FooDB	31437929
Plant	Fruit	Cucurbita pepo var. clypeata	FooDB	31437929
Plant	Seed	Borago officinalis	FooDB	31437929
Plant		Scorzonera hispanica	FooDB	31437929
Plant	Root	Pastinaca sativa	FooDB	31437929
Plant	Leaves	Mentha spicata	FooDB	31437929
Plant		Manihot esculenta	FooDB	31437929
Plant	Flower	Linum usitatissimum	FooDB	31437929
Plant	Seed	Cucurbita maxima	FooDB	31437929
Plant		Ipomoea batatas	FooDB	31437929
Plant	Leaves	Brassica oleracea var. italica	FooDB	31437929
Plant	Seed	Phaseolus vulgaris	FooDB	31437929
Plant	Oil	Helianthus annuus	FooDB	31437929
Plant	Seed oil	Vitis	FooDB	31437929
Plant	Root	Beta vulgaris var. rubra	FooDB	31437929
Plant	Seed	Glycine max	FooDB	31437929
Plant		Lactuca sativa	FooDB	31437929
Plant	Seed	Anethum graveolens	FooDB	31437929
Plant	Fruit	Citrus aurantiifolia	FooDB	31437929
Plant	Fruit	Ficus carica	FooDB	31437929
Plant	Seed	Sesamum orientale	FooDB	31437929
Plant	Fruit	Pisum sativum	FooDB	31437929
Plant		Brassica oleracea var. gemmifera	FooDB	31437929
Plant	Seed	Hippophae rhamnoides	FooDB	31437929
Plant	Fruit	Actinidia chinensis	FooDB	31437929
Plant	Seed	Eruca vesicaria ssp. sativa	FooDB	31437929
Plant	Fruit	Cucurbita pepo var. cylindrica	FooDB	31437929
Plant	Fruit	Passiflora edulis	FooDB	31437929
Plant	Seed	Sinapis alba	FooDB	31437929
Plant		Musa x paradisiaca	FooDB	31437929
Plant		Allium	FooDB	31437929
Plant		Lens culinaris	FooDB	31437929
Plant	Leaves	Apium graveolens var. secalinum	FooDB	31437929
Plant		Abelmoschus esculentus	FooDB	31437929
Plant	Seed	Punica granatum	FooDB	31437929
Plant	Fruit	Cucurbita pepo var. cylindrica	FooDB	31437929
Plant	Fruit	Citrus x paradisi	FooDB	31437929
Plant	Seed	Pinus edulis	FooDB	31437929
Plant	Root	Daucus carota ssp. sativus	FooDB	31437929
Plant	Nut	Arachis hypogaea	FooDB	31437929
Plant		Pisum sativum	FooDB	31437929
Plant		Cichorium intybus	FooDB	31437929
Plant	Root	Zingiber officinale	FooDB	31437929
Plant	Fruit	Mangifera indica	FooDB	31437929
Plant	Seed	Medicago sativa	FooDB	31437929
Plant	Root	Arctium lappa	FooDB	31437929
Plant	Shoot	Asparagus officinalis	FooDB	31437929
Plant	Fruit	Phoenix dactylifera	FooDB	31437929
Plant	Tuber	Solanum tuberosum	FooDB	31437929
Plant	Leaves		FooDB	31437929
Plant	Fruit	Ananas comosus	FooDB	31437929
Plant	Fruit	Prunus persica	FooDB	31437929
Plant	Seed	Origanum majorana	FooDB	31437929
Plant	Fruit	Hippophae rhamnoides	FooDB	31437929
Plant		Rorippa nasturtium-aquaticum	FooDB	31437929
Plant	Seed	Phaseolus vulgaris	FooDB	31437929
Plant	Root	Raphanus sativus var. longipinnatus	FooDB	31437929
Plant	Juice	Citrus limon	FooDB	31437929
Plant	Plant	Laurus nobilis	FooDB	31437929
Plant	Seed	Juglans regia	FooDB	31437929
Plant		Carica papaya	FooDB	31437929
Plant	Fruit	Malus	FooDB	31437929
Plant	Seed	Glycine max	FooDB	31437929
Plant	Seed	Vigna mungo	FooDB	31437929
Plant	Fruit	Solanum lycopersicum	FooDB	31437929
Plant		Cynara scolymus	FooDB	31437929
Plant		Brassica oleracea	FooDB	31437929
Plant	Fruit	Ribes rubrum	FooDB	31437929
Plant	Fruit	Solanum melongena	FooDB	31437929
Plant		Brassica oleracea var. botrytis	FooDB	31437929
Plant	Bulb	Allium sativum l. var. sativum	FooDB	31437929
Plant	Oil	Juglans	FooDB	31437929
Plant	Leaves	Psophocarpus tetragonolobus	FooDB	31437929
Plant	Seed	Linum usitatissimum	FooDB	31437929
Plant		Petroselinum crispum	FooDB	31437929
Plant	Fruit	Capsicum annuum	FooDB	31437929
Plant	Fruit	Ribes nigrum	FooDB	31437929
Plant	Fruit	Ribes nigrum	FooDB	31437929
Plant		Lepidium sativum	FooDB	31437929
Plant		Pastinaca sativa	FooDB	31437929
Plant	Leaves		FooDB	31437929
Plant	Fruit	Cucurbita maxima	FooDB	31437929
Plant	Fruit	Vitis	FooDB	31437929
Plant	Fruit	Capsicum annuum	FooDB	31437929
Plant	Seed	Helianthus annuus	FooDB	31437929
Plant	Root	Ipomoea batatas	FooDB	31437929
Plant	Fruit	Cucumis melo	FooDB	31437929
Plant	Root	Beta vulgaris var. rubra	FooDB	31437929
Plant	Sprout	Glycine max	FooDB	31437929
Plant	Fruit	Persea americana	FooDB	31437929
Plant	Fruit	Prunus cerasus	FooDB	31437929
Plant		Lactuca sativa	FooDB	31437929
Plant	Fruit	Cucumis sativus	FooDB	31437929
Plant		Brassica oleracea var. gongylodes	FooDB	31437929
Plant	Seed	Pistacia vera	FooDB	31437929
Plant	Fruit	Fragaria x ananassa	FooDB	31437929
Plant	Juice	Prunus	FooDB	31437929
Plant		Anethum graveolens	FooDB	31437929
Plant	Leaves	Cichorium intybus	FooDB	31437929
Plant	Fruit	Phaseolus vulgaris	FooDB	31437929
Plant	Seed	Juglans cinerea	FooDB	31437929
Plant		Agaricus bisporus	FooDB	31437929
Plant		Lactuca sativa l. var. longifolia	FooDB	31437929
Plant	Oil	Sesamum orientale	FooDB	31437929
Plant	Seed	Psophocarpus tetragonolobus	FooDB	31437929
Plant		Allium	FooDB	31437929
Plant	Fruit	Citrus aurantiifolia	FooDB	31437929
Plant		Brassica oleracea var. gemmifera	FooDB	31437929
Plant	Flour	Solanum tuberosum	FooDB	31437929
Plant	Fruit	Citrus reticulata	FooDB	31437929
Plant	Seed	Artocarpus altilis	FooDB	31437929
Plant		Helianthus tuberosus	FooDB	31437929
Plant	Root	Armoracia rusticana	FooDB	31437929
Plant		Brassica oleracea var. italica	FooDB	31437929
Plant	Leaves	Tetragonia tetragonioides	FooDB	31437929
Plant	Root	Foeniculum vulgare	FooDB	31437929
Plant	Seed	Pisum sativum	FooDB	31437929
Plant	Leaves		FooDB	31437929
Plant	Peel	Citrus limon	FooDB	31437929
Plant	Leaves	Lepidium sativum	FooDB	31437929
Plant	Fruit	Litchi chinensis	FooDB	31437929
Plant	Pollen or spore	Taraxacum officinale	FooDB	31437929
Plant	Seed	Cajanus cajan	FooDB	31437929
Plant	Seed	Cicer arietinum	FooDB	31437929
Plant	Seed oil	Trigonella foenum-graecum	FooDB	31437929
Plant	Fruit	Solanum lycopersicum	FooDB	31437929
Plant	Seed	Juglans nigra	FooDB	31437929
Plant	Fruit	Psidium cattleianum	FooDB	31437929
Plant	Root	Cichorium intybus	FooDB	31437929
Plant		Brassica oleracea var. sabauda	FooDB	31437929
Plant	Fruit	Ficus carica	FooDB	31437929
Plant	Powder	Rosa	FooDB	31437929
Plant	Tuber	Psophocarpus tetragonolobus	FooDB	31437929
Plant	Oil	Linum usitatissimum	FooDB	31437929
Plant	Fruit	Solanum melongena	FooDB	31437929
Plant		Eragrostis tef	FooDB	31437929
Plant	Seed	Lepidium sativum	FooDB	31437929
Plant	Seed	Vigna aconitifolia	FooDB	31437929
Plant	Fruit	Physalis	FooDB	31437929
Plant	Leaves		FooDB	31437929
Plant	Fruit	Punica granatum	FooDB	31437929
Plant	Plant	Artemisia dracunculus	FooDB	31437929
Plant	Leaves		FooDB	31437929
Plant	Seed	Coriandrum sativum	FooDB	31437929
Plant	Leaves	Lactuca sativa	FooDB	31437929
Plant	Fruit	Cucumis melo	FooDB	31437929
Plant		Brassica napus	FooDB	31437929
Plant	Fruit	Elettaria cardamomum	FooDB	31437929
Plant	Fruit	Cucurbita pepo var. cylindrica	FooDB	31437929
Plant	Nut	Pistacia vera	FooDB	31437929
Plant		Amaranthus	FooDB	31437929
Plant	Oil	Gossypium	FooDB	31437929
Plant	Fruit	Persea americana	FooDB	31437929
Plant	Fruit	Diospyros	FooDB	31437929
Plant	Juice	Prunus	FooDB	31437929
Plant	Fruit	Fragaria x ananassa	FooDB	31437929
Plant	Fruit	Prunus domestica	FooDB	31437929
Plant		Brassica oleracea	FooDB	31437929
Plant	Fruit	Solanum lycopersicum var. lycopersicum	FooDB	31437929
Plant	Herb	Portulaca oleracea	FooDB	31437929
Plant	Shoot	Asparagus officinalis	FooDB	31437929
Plant	Fruit	Vitis vinifera	FooDB	31437929
Plant	Leaves	Mentha x piperita	FooDB	31437929
Plant	Fruit	Malus pumila	FooDB	31437929
Plant		Allium ampeloprasum	FooDB	31437929
Plant	Fruit	Capsicum annuum	FooDB	31437929
Plant	Fruit	Ribes rubrum	FooDB	31437929
Plant		Lactuca sativa	FooDB	31437929
Plant	Seed essential oil	Ribes nigrum	FooDB	31437929
Plant	Fruit	Prunus armeniaca	FooDB	31437929
Plant	Fruit	Annona cherimola	FooDB	31437929
Plant	Oil	Carthamus tinctorius	FooDB	31437929
Plant	Seed	Phaseolus vulgaris	FooDB	31437929
Plant	Fruit	Sechium edule	FooDB	31437929
Plant	Nut	Carya illinoinensis	FooDB	31437929
Plant		Brassica rapa var. rapa	FooDB	31437929
Plant	Fruit	Ananas comosus	FooDB	31437929
Plant	Fruit	Piper nigrum	FooDB	31437929
Plant		Solanum tuberosum	FooDB	31437929
Plant	Fruit	Rubus x loganobaccus	FooDB	31437929
Plant	Fruit	Citrus sinensis	FooDB	31437929
Plant	Root	Daucus carota ssp. sativus	FooDB	31437929
Plant		Ipomoea batatas	FooDB	31437929
Plant	Leaves	Allium schoenoprasum	FooDB	31437929
Plant	Bean sprout	Vigna radiata	FooDB	31437929
Plant	Seed	Portulaca oleracea	FooDB	31437929
Plant	Shoot	Apium graveolens var. rapaceum	FooDB	31437929
Plant	Fruit	Solanum lycopersicum	FooDB	31437929
Plant	Seed	Ocimum basilicum	FooDB	31437929
Plant	Seed oil	Vitellaria paradoxa	FooDB	31437929
Plant	Seed	Linum usitatissimum	FooDB	31437929
Plant		Brassica rapa var. chinensis	FooDB	31437929
Plant	Fruit	Rosa	FooDB	31437929
Plant		Lens culinaris	FooDB	31437929
Plant	Seed	Vigna unguiculata ssp. unguiculata	FooDB	31437929
Plant	Root	Daucus carota ssp. sativus	FooDB	31437929
Plant	Seed	Sesamum orientale	FooDB	31437929
Plant	Fruit	Cucurbita	FooDB	31437929
Plant	Fruit	Cucurbita pepo var. cylindrica	FooDB	31437929
Plant	Seed	Pisum sativum	FooDB	31437929
Plant	Root	Dioscorea pentaphylla	FooDB	31437929
Plant	Fruit	Citrus limon	FooDB	31437929
Plant	Fruit	Capsicum annuum var. annuum	FooDB	31437929
Plant	Leaves		FooDB	31437929
Plant	Leaves	Spinacia oleracea	FooDB	31437929
Plant	Nut	Bertholletia excelsa	FooDB	31437929
Plant		Brassica oleracea var. italica	FooDB	31437929
Plant	Sprout seedling	Phaseolus vulgaris	FooDB	31437929
Plant	Seed	Apium graveolens	FooDB	31437929
Plant	Leaves	Corchorus olitorius	FooDB	31437929
Plant	Bean	Phaseolus vulgaris	FooDB	31437929
Plant	Juice	Vitis	FooDB	31437929
Plant	Leaves	Cichorium endivia	FooDB	31437929
Plant	Leaves	Taraxacum officinale	FooDB	31437929
Plant		Cichorium intybus	FooDB	31437929
Plant	Fruit	Cucumis melo	FooDB	31437929
Plant	Fruit	Prunus	FooDB	31437929
Plant		Anethum graveolens	FooDB	31437929
Plant		Brassica rapa	FooDB	31437929
Plant	Fruit	Citrus reticulata	FooDB	31437929
Plant	Seed	Corchorus olitorius	FooDB	31437929
Plant	Oil	Arachis hypogaea	FooDB	31437929
Plant	Oil	Brassica napus var. napus	FooDB	31437929
Plant	Fruit	Malus pumila	FooDB	31437929
Plant	Seed	Carum carvi	FooDB	31437929
Plant	Oil	Carthamus tinctorius	FooDB	31437929
Plant	Leaves	Brassica oleracea var. gemmifera	FooDB	31437929
Plant	Plant	Allium ampeloprasum	FooDB	31437929
Plant	Oil	Cocos nucifera	FooDB	31437929
Plant	Fruit	Prunus armeniaca	FooDB	31437929
Plant	Leaves	Coriandrum sativum	FooDB	31437929
Plant	Plant	Theobroma cacao	FooDB	31437929
Plant	Bulb	Allium cepa	FooDB	31437929
Plant		Juglans nigra	FooDB	31437929
Plant	Seed	Cucurbita pepo var. clypeata	FooDB	31437929
Plant		Solanum tuberosum	FooDB	31437929
Plant	Wood	Tilia	FooDB	31437929
Plant	Juice	Ribes nigrum	FooDB	31437929
Plant	Leaves	Lactuca sativa	FooDB	31437929
Plant	Cotyledon	Cucumis sativus	FooDB	31437929
Plant	Seed	Papaver	FooDB	31437929
Plant	Seed	Vigna radiata	FooDB	31437929
Plant	Oil	Linum usitatissimum	FooDB	31437929
Plant	Leaves	Camellia sinensis	FooDB	31437929
Plant	Fruit	Prunus domestica	FooDB	31437929
Plant	Fruit	Prunus persica var. nucipersica	FooDB	31437929
Plant	Seed	Ceratonia siliqua	FooDB	31437929
Plant	Leaves	Brassica oleracea l. var. capitata l. f. alba dc.	FooDB	31437929
Plant		Annona cherimola	FooDB	31437929
Plant	Fruit	Ginkgo biloba	FooDB	31437929
Plant	Leaves	Brassica oleracea var. capitata	FooDB	31437929
Plant	Fruit	Solanum lycopersicum	FooDB	31437929
Plant	Flour	Glycine max	FooDB	31437929
Plant	Fruit	Psidium guajava	FooDB	31437929
Plant	Plant	Origanum vulgare	FooDB	31437929
Plant	Fruit	Citrullus lanatus	FooDB	31437929
Plant	Cotyledon	Cucumis melo	FooDB	31437929
Plant		Lens culinaris	FooDB	31437929
Plant	Plant	Capparis spinosa	FooDB	31437929
Plant		Cichorium endivia	FooDB	31437929
Plant	Seed	Vicia faba	FooDB	31437929
Plant	Plant	Spinacia oleracea	FooDB	31437929
Plant	Fruit	Cucurbita pepo var. cylindrica	FooDB	31437929
Plant	Seed	Sesamum orientale	FooDB	31437929
Plant	Seed	Daucus carota ssp. sativus	FooDB	31437929
Plant	Seed	Pisum sativum	FooDB	31437929
Plant	Juice	Fragaria x ananassa	FooDB	31437929
Plant	Shoot	Phyllostachys edulis	FooDB	31437929
Plant	Shoot	Asparagus officinalis	FooDB	31437929
Plant	Fruit	Vitis	FooDB	31437929
Plant		Allium schoenoprasum	FooDB	31437929
Plant	Fruit	Cucumis sativus	FooDB	31437929
Plant	Leaves	Oenothera biennis	FooDB	31437929
Plant	Rhizome	Nelumbo nucifera	FooDB	31437929
Plant	Bean	Phaseolus vulgaris	FooDB	31437929
Plant	Fruit	Cucurbita	FooDB	31437929
Plant	Seed	Satureja hortensis	FooDB	31437929
Plant	Oil	Elaeis	FooDB	31437929
Plant	Oil	Brassica napus var. napus	FooDB	31437929
Plant		Anthriscus cerefolium	FooDB	31437929
Plant		Brassica oleracea var. botrytis	FooDB	31437929
Plant	Seed	Anacardium occidentale	FooDB	31437929
Plant	Juice	Sambucus	FooDB	31437929
Plant		Brassica oleracea var. gemmifera	FooDB	31437929
Plant	Fruit	Pyrus communis	FooDB	31437929
Plant		Brassica napus var. pabularia	FooDB	31437929
Plant		Eriobotrya japonica	FooDB	31437929
Plant		Tilia cordata	FooDB	31437929
Plant	Leaves	Colocasia esculenta	FooDB	31437929
Plant	Fruit	Malus pumila	FooDB	31437929
Plant		Rheum rhabarbarum	FooDB	31437929
Plant	Seed	Bertholletia excelsa	FooDB	31437929
Plant	Fruit	Averrhoa carambola	FooDB	31437929
Plant	Seed	Prunus dulcis	FooDB	31437929
Plant	Seed	Lens culinaris	FooDB	31437929
Plant	Seed	Cydonia oblonga	FooDB	31437929
Plant	Powder	Allium sativum	FooDB	31437929
Plant	Fruit	Cocos nucifera	FooDB	31437929
Plant	Leaves	Coriandrum sativum	FooDB	31437929
Plant	Fruit	Vaccinium	FooDB	31437929
Plant	Bean sprout	Phaseolus vulgaris	FooDB	31437929
Plant		Beta vulgaris ssp. cicla	FooDB	31437929
Plant	Fruit	Cucurbita pepo var. clypeata	FooDB	31437929
Plant	Seed	Cicer arietinum	FooDB	31437929
Plant		Solanum tuberosum	FooDB	31437929
Plant	Juice	Ribes nigrum	FooDB	31437929
Plant	Fruit	Ribes uva-crispa	FooDB	31437929
Plant		Rumex acetosa	FooDB	31437929
Plant	Fruit	Cucurbita pepo var. cylindrica	FooDB	31437929
Plant	Fruit	Malus pumila	FooDB	31437929
Plant		Linum usitatissimum	FooDB	31437929
Plant	Seed	Nelumbo nucifera	FooDB	31437929
Plant		Piper nigrum	FooDB	31437929
Plant	Seed	Vigna radiata	FooDB	31437929
Plant	Cotyledon	Momordica charantia	FooDB	31437929
Plant		Citrus japonica	FooDB	31437929
Plant	Fruit	Citrus sinensis	FooDB	31437929
Plant	Leaves	Camellia sinensis	FooDB	31437929
Plant		Spinacia oleracea	FooDB	31437929
Plant	Fruit	Prunus persica	FooDB	31437929
Plant	Oil	Glycine max	FooDB	31437929
Plant	Fruit	Vaccinium myrtillus	FooDB	31437929
Plant	Nut	Castanea	FooDB	31437929
Plant		Cichorium endivia	FooDB	31437929
Plant	Root	Colocasia esculenta	FooDB	31437929
Plant	Seed	Pachyrhizus erosus	FooDB	31437929
Plant	Fruit essential oil	Salvia officinalis	FooDB	31437929
Plant	Root	Daucus carota	FooDB	31437929
Plant	Seed	Carthamus tinctorius	FooDB	31437929
Plant	Fruit	Opuntia	FooDB	31437929
Plant	Seed oil	Tamarindus indica	FooDB	31437929
Plant	Shoot	Asparagus officinalis	FooDB	31437929
Plant	Fruit	Rubus idaeus	FooDB	31437929
Plant	Fruit	Carica papaya	FooDB	31437929
Plant		Cinnamomum	FooDB	31437929
Plant	Seed	Psidium guajava	FooDB	31437929
Plant	Seed	Ginkgo biloba	FooDB	31437929
Plant	Juice	Fragaria x ananassa	FooDB	31437929
Plant	Seed	Pisum sativum	FooDB	31437929
Plant	Sprout seedling	Lens culinaris	FooDB	31437929
Plant	Leaves	Rumex acetosa	FooDB	31437929
Plant	Tuber	Dioscorea	FooDB	31437929
Plant	Fruit	Vigna unguiculata ssp. sesquipedalis	FooDB	31437929
Plant	Bean	Phaseolus vulgaris	FooDB	31437929
Plant	Root	Manihot esculenta	FooDB	31437929
Plant	Root	Petroselinum crispum	FooDB	31437929
Plant	Seed	Lablab purpureus	FooDB	31437929
Plant	Oil	Olea europaea	FooDB	31437929
Plant		Brassica oleracea	FooDB	31437929
Plant	Fruit	Capsicum annuum	FooDB	31437929
Plant	Fruit	Cucurbita	FooDB	31437929
Plant		Vicia faba	FooDB	31437929
Plant		Anthriscus cerefolium	FooDB	31437929
Plant	Fruit	Ribes rubrum	FooDB	31437929
Plant		Brassica oleracea var. botrytis	FooDB	31437929
Plant		Myristica fragrans	FooDB	31437929
Plant	Juice	Sambucus	FooDB	31437929
Plant	Oil	Cirsium	FooDB	31437929
Plant	Fruit	Cucumis sativus	FooDB	31437929
Plant		Brassica oleracea var. gemmifera	FooDB	31437929
Plant	Seed	Coffea arabica	FooDB	31437929
Plant	Fruit	Musa x paradisiaca	FooDB	31437929
Plant	Silk stigma style	Crocus sativus	FooDB	31437929
Plant		Lactuca sativa	FooDB	31437929
Plant	Sprout seedling	Vigna radiata	FooDB	31437929
Plant	Seed	Nuphar lutea	FooDB	31437929
Plant	Fruit	Mangifera indica	FooDB	31437929
Plant	Leaves	Beta vulgaris var. rubra	FooDB	31437929
Plant	Fruit	Cucurbita pepo var. cylindrica	FooDB	31437929
Plant	Fruit	Cydonia oblonga	FooDB	31437929
Plant	Bean	Phaseolus vulgaris	FooDB	31437929
Plant	Seed	Helianthus annuus	FooDB	31437929
Plant	Fruit	Vaccinium	FooDB	31437929
Plant		Apium graveolens	FooDB	31437929
Plant	Fruit	Capsicum annuum	FooDB	31437929
Plant	Fruit	Ribes nigrum	FooDB	31437929
Plant	Fruit	Pyrus communis	FooDB	31437929
Plant		Glycine max	FooDB	31437929
Plant	Fruit	Tamarindus indica	FooDB	31437929
Plant		Pleurotus ostreatus	FooDB	31437929
Plant		Rheum rhabarbarum	FooDB	31437929
Plant	Root	Zingiber officinale	FooDB	31437929
Plant	Seed	Vigna unguiculata ssp. sesquipedalis	FooDB	31437929
Plant	Leaves	Rosmarinus officinalis	FooDB	31437929
Plant	Root	Raphanus sativus	FooDB	31437929
Plant		Prunus dulcis	FooDB	31437929
Plant	Fruit	Psidium guajava	FooDB	31437929
Plant	Seed	Lupinus albus	FooDB	31437929
Plant	Fruit	Ribes uva-crispa	FooDB	31437929
Plant	Oil	Elaeis	FooDB	31437929
Plant		Lens culinaris	FooDB	31437929
Plant	Plant	Thymus vulgaris	FooDB	31437929
Plant		Allium	FooDB	31437929
Plant	Seed	Passiflora edulis	FooDB	31437929
Plant		Armoracia rusticana	FooDB	31437929
Plant	Plant	Glycine max	FooDB	31437929
Plant		Allium sativum	FooDB	31437929
Plant	Seed	Salvia officinalis	FooDB	31437929

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

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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 ]
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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 ]
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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:0x00007f46ddc09420>

3D MOL for #<Metabolite:0x00007f46ddc09420>

3D SDF for #<Metabolite:0x00007f46ddc09420>

3D-SDF for #<Metabolite:0x00007f46ddc09420>

PDB for #<Metabolite:0x00007f46ddc09420>

3D PDB for #<Metabolite:0x00007f46ddc09420>

SMILES for #<Metabolite:0x00007f46ddc09420>

INCHI for #<Metabolite:0x00007f46ddc09420>

Structure for #<Metabolite:0x00007f46ddc09420>

3D Structure for #<Metabolite:0x00007f46ddc09420>