NP-MRD: Showing NP-Card for Alpha-Linolenic acid (NP0000694)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-17 15:42:41 UTC

NP-MRD ID

NP0000694

Secondary Accession Numbers

None

Natural Product 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>
NP0000694

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-

> <INCHI_KEY>
DTOSIQBPPRVQHS-PDBXOOCHSA-N

> <FORMULA>
C18H30O2

> <MOLECULAR_WEIGHT>
278.4296

> <EXACT_MASS>
278.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
34.98036100681455

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.62

> <JCHEM_LOGP>
6.059955137666666

> <ALOGPS_LOGS>
-6.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167283903808

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
89.6354

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.66e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α linolenic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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

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

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

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

View in JSmol View NMR Assignments

Synonyms

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

Chemical Formula

C₁₈H₃₀O₂

Average Mass

278.4296 Da

Monoisotopic Mass

278.22458 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	FooDB	DTU Food
Abies pinsapo	LOTUS Database	35616633
Abramis brama	FooDB	DTU Food
Abrus precatorius	LOTUS Database	35616633
Abutilon ramosum	LOTUS Database	35616633
Acacia polyacantha	LOTUS Database	35616633
Acanthopanax gracilistylus	KNApSAcK Database	22123792
Acipenseridae	FooDB	DTU Food
Actinidia chinensis	FooDB	DTU Food
Aegle marmelos	Plant	KNApSAcK
Aesculus hippocastanum	LOTUS Database	35616633
Agaricus bisporus	FooDB	DTU Food
Agaricus blazei	LOTUS Database	35616633
Agave	FooDB	FooDB
Agave americana	LOTUS Database	35616633
Agave decipiens	LOTUS Database	35616633
Allamanda cathartica	LOTUS Database	35616633
Allium ampeloprasum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium ascalonicum	FooDB	FooDB
Allium cepa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium cepa L.	FooDB	DTU Food
Allium fistulosum	FooDB	FooDB
Allium hirtifolium	Plant	KNApSAcK
Allium obliquum	LOTUS Database	35616633
Allium sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium schoenoprasum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium tuberosum	FooDB	FooDB
Aloe vera var.chinensis	KNApSAcK Database	22123792
Aloysia triphylla	FooDB	FooDB
Alpinia oxyphylla	KNApSAcK Database	22123792
Amaranthus	FooDB	USDA
Amaranthus spinosus	LOTUS Database	35616633
Amaranthus tricolor	LOTUS Database	35616633
Amelanchier alnifolia	FooDB	FooDB
Anabaena flos-aquae	KNApSAcK Database	22123792
Anacardium occidentale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ananas comosus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Anarhichas lupus	FooDB	DTU Food
Anatidae	FooDB	DTU Food
Anethum graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Angelica keiskei	FooDB	FooDB
Anguilliformes	FooDB	DTU Food
Annona cherimola	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Annona muricata	FooDB	FooDB
Annona reticulata	FooDB	FooDB
Annona squamosa	FooDB	FooDB
Anthriscus cerefolium	FooDB	DTU Food
Apios americana	LOTUS Database	35616633
Apium graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Apium graveolens var. dulce	FooDB	FooDB
Apium graveolens var. rapaceum	FooDB	DTU Food
Apium graveolens var. secalinum	FooDB	DTU Food
Arabidopsis thaliana	KNApSAcK Database	22123792
Arachis hypogaea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Arctium lappa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Armoracia rusticana	FooDB	DTU Food
Artemisia dracunculus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Artemisia vulgaris	FooDB	FooDB
Artocarpus altilis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Artocarpus heterophyllus	FooDB	FooDB
Asclepias syriaca	LOTUS Database	35616633
Asparagus officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Astacidea	FooDB	DTU Food
Astragalus danicus	LOTUS Database	35616633
Astragalus mongholicus	KNApSAcK Database	22123792
Attalea speciosa	FooDB	FooDB
Auricularia auricula-judae	FooDB	FooDB
Auricularia polytricha	FooDB	FooDB
Avena sativa L.	FooDB	DTU Food
Averrhoa carambola	KNApSAcK Database	22123792
Azadirachta indica	KNApSAcK Database	22123792
Azima tetracantha	LOTUS Database	35616633
Basella alba	FooDB	FooDB
Bellis perennis	LOTUS Database	35616633
Belone belone	FooDB	DTU Food
Benincasa hispida	FooDB	FooDB
Bertholletia excelsa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Beta vulgaris	FooDB	FooDB
Beta vulgaris ssp. cicla	FooDB	DTU Food
Bidens pilosa	LOTUS Database	35616633
Boehmeria nivea	LOTUS Database	35616633
Borago officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Bos taurus	FooDB	DTU Food
Brachyura	FooDB	DTU Food
Brassica alboglabra	FooDB	FooDB
Brassica juncea	FooDB	FooDB
Brassica napus	FooDB	DTU Food
Brassica napus var. napus	FooDB	DTU Food
Brassica oleracea	FooDB	DTU Food
Brassica oleracea var. botrytis	FooDB	DTU Food
Brassica oleracea var. capitata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. gemmifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. gongylodes	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. italica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. sabauda	FooDB	DTU Food
Brassica oleracea var. viridis	FooDB	FooDB
Brassica rapa	FooDB	DTU Food
Brassica rapa ssp. chinensis	FooDB	DTU Food
Brassica rapa var. pekinensis	FooDB	FooDB
Brassica rapa var. rapa	FooDB	DTU Food
Brassica ruvo	FooDB	FooDB
Brosimum alicastrum	FooDB	FooDB
Bryonia alba	LOTUS Database	35616633
Bupleurum chinense	KNApSAcK Database	22123792
Byrsonima crassifolia	FooDB	FooDB
Cajanus cajan	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Calophyllum calaba	KNApSAcK Database	22123792
Calophyllum inophyllum	KNApSAcK Database	22123792
Camellia sinensis	LOTUS Database	35616633
Canarium ovatum	FooDB	FooDB
Canavalia ensiformis	LOTUS Database	35616633
Cannabis sativa	CannabisDB	Not Available
Cantharellus cibarius	FooDB	DTU Food
Capparis spinosa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Capsicum annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Capsicum annuum L.	FooDB	FooDB
Capsicum annuum var. annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Capsicum chinense	FooDB	FooDB
Capsicum pubescens	FooDB	FooDB
Carica papaya	LOTUS Database	35616633
Carica papaya L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Caridea	FooDB	DTU Food
Carissa macrocarpa	FooDB	FooDB
Carthamus tinctorius	KNApSAcK Database	22123792
Carum carvi	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Carya	FooDB	FooDB
Carya illinoinensis	FooDB	DTU Food
Castanea	FooDB	DTU Food
Castanea crenata	FooDB	FooDB
Castanea mollissima	FooDB	FooDB
Castanea sativa	FooDB	FooDB
Catharanthus roseus	LOTUS Database	35616633
Celastrus paniculata	LOTUS Database	35616633
Celosia cristada	KNApSAcK Database	22123792
Centaurea aspera	LOTUS Database	35616633
Ceratonia siliqua	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Chamaecyparis formosensis	LOTUS Database	35616633
Chamaemelum nobile	KNApSAcK Database	22123792
Chamerion angustifolium	FooDB	FooDB
Chenopodium album	FooDB	FooDB
Chenopodium quinoa	FooDB	FooDB
Chlorella vulgaris	KNApSAcK Database	22123792
Chrysanthemum coronarium	FooDB	FooDB
Cicer arietinum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cichlidae	FooDB	USDA
Cichorium endivia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cichorium intybus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cinnamomum	FooDB	DTU Food
Cinnamomum aromaticum	FooDB	FooDB
Cinnamomum verum	FooDB	FooDB
Cirsium	FooDB	DTU Food
Citrullus lanatus	FooDB	DTU Food
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	DTU Food
Citrus aurantiifolia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus latifolia	FooDB	FooDB
Citrus limon	FooDB	DTU Food
Citrus maxima	FooDB	FooDB
Citrus paradisi	FooDB	DTU Food
Citrus reticulata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Clitoria ternata	KNApSAcK Database	22123792
Clitoria ternatea	LOTUS Database	35616633
Clupeinae	FooDB	DTU Food
Cocos nucifera	FooDB	DTU Food
Coffea arabica L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Coffea canephora	FooDB	DTU Food
Colletia spinosissima	LOTUS Database	35616633
Colocasia esculenta	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Columbidae	FooDB	DTU Food
Consolida regalis	LOTUS Database	35616633
Corchorus aestuans	LOTUS Database	35616633
Corchorus olitorius	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Coregonus	FooDB	DTU Food
Coriandrum sativum L.	FooDB	DTU Food
Corylus	FooDB	DTU Food
Corylus avellana	FooDB	FooDB
Crataegus pinnatifida	KNApSAcK Database	22123792
Crateva religiosa	FooDB	FooDB
Crocus sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Crotalaria pallida	LOTUS Database	35616633
Croton cortesianus	LOTUS Database	35616633
Croton tiglium	KNApSAcK Database	22123792
Cryptomeria japonica	LOTUS Database	35616633
Cucumis melo	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cucumis metuliferus	FooDB	FooDB
Cucumis sativus	LOTUS Database	35616633
Cucumis sativus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cucurbita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cucurbita foetidissima	LOTUS Database	35616633
Cucurbita maxima	FooDB	DTU Food
Cucurbita moschata	FooDB	FooDB
Cullen corylifolium	Plant	KNApSAcK
Cuminum cyminum	FooDB	FooDB
Cuphea epilobiifolia	LOTUS Database	35616633
Curcuma longa	Plant	KNApSAcK
Cuscuta pentagona	LOTUS Database	35616633
Cyclopteridae	FooDB	DTU Food
Cydonia oblonga	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cymbopogon citratus	FooDB	FooDB
Cynara cardunculus	FooDB	FooDB
Cynara scolymus	FooDB	DTU Food
Cystoclonium purpureum	LOTUS Database	35616633
Daucus carota	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Daucus carota ssp. sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Dictamnus albus	LOTUS Database	35616633
Dimocarpus longan	FooDB	FooDB
Dioscorea	FooDB	DTU Food
Dioscorea pentaphylla	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Diospyros	FooDB	DTU Food
Diospyros kaki	FooDB	FooDB
Diospyros virginiana	FooDB	FooDB
Dipteryx lacunifera	LOTUS Database	35616633
Dolichomitra cymbifolia	LOTUS Database	35616633
Drymaria cordata	KNApSAcK Database	22123792
Drypetes roxburghii	LOTUS Database	35616633
Durio zibethinus	FooDB	FooDB
Dysphania ambrosioides	FooDB	FooDB
Echinacea purpurea	LOTUS Database	35616633
Echium auberianum	KNApSAcK Database	22123792
Echium boissieri	KNApSAcK Database	22123792
Echium gentianoides	KNApSAcK Database	22123792
Echium giganteum	KNApSAcK Database	22123792
Echium lusitanicum	KNApSAcK Database	22123792
Echium pitardii	KNApSAcK Database	22123792
Echium plantagineum	KNApSAcK Database	22123792
Echium sabulicola	KNApSAcK Database	22123792
Echium strictum	KNApSAcK Database	22123792
Echium vulgare	KNApSAcK Database	22123792
Elaeagnus angustifolia	LOTUS Database	35616633
Elaeis	FooDB	DTU Food
Elaeis guineensis	LOTUS Database	35616633
Eleocharis dulcis	FooDB	FooDB
Elettaria cardamomum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Elymus repens	LOTUS Database	35616633
Empetrum nigrum	FooDB	FooDB
Engraulidae	FooDB	DTU Food
Epilobium parviflorum	LOTUS Database	35616633
Epimedium brevicornum	KNApSAcK Database	22123792
Eragrostis tef	FooDB	USDA
Erigeron caucasicus	LOTUS Database	35616633
Eriobotrya japonica	FooDB	DTU Food
Eruca vesicaria	LOTUS Database	35616633
Eruca vesicaria subsp. Sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Esox lucius	FooDB	DTU Food
Eucheuma	FooDB	DTU Food
Eugenia javanica	FooDB	FooDB
Eugenia uniflora	FooDB	FooDB
Euphausia superba	LOTUS Database	35616633
Euphorbia characias	LOTUS Database	35616633
Euphorbia glareosa	LOTUS Database	35616633
Eurhynchium striatum	LOTUS Database	35616633
Eutrema japonicum	FooDB	FooDB
Fagopyrum esculentum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Fagopyrum tataricum	FooDB	FooDB
Fagus	FooDB	FooDB
Feijoa sellowiana	FooDB	FooDB
Fernandoa adenophylla	LOTUS Database	35616633
Festuca rubra	LOTUS Database	35616633
Ficus carica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Fimbristylis quinquangularis	LOTUS Database	35616633
Flammulina velutipes	FooDB	FooDB
Foeniculum vulgare	FooDB	DTU Food
Fragaria x ananassa	FooDB	DTU Food
Gadiformes	FooDB	DTU Food
Gadus	FooDB	DTU Food
Gallus gallus	FooDB	DTU Food
Garcinia mangostana	FooDB	FooDB
Garcinia xanthochymus	LOTUS Database	35616633
Gastropoda	FooDB	DTU Food
Gaylussacia baccata	FooDB	FooDB
Ginkgo biloba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gleditsia triacanthos	LOTUS Database	35616633
Glycine max	KNApSAcK Database	22123792
Gnetum edule	LOTUS Database	35616633
Gossypium	FooDB	DTU Food
Gossypium hirsutum	LOTUS Database	35616633
Gracilaria gracilis	LOTUS Database	35616633
Grifola frondosa	FooDB	FooDB
Gymnanthemum myrianthum	LOTUS Database	35616633
Hedysarum alpinum	FooDB	FooDB
Helianthus annuus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Helianthus porteri	LOTUS Database	35616633
Helianthus tuberosus	FooDB	DTU Food
Hibiscus cannabinus	LOTUS Database	35616633
Hibiscus sabbariffa	FooDB	FooDB
Hieracium intybaceum All.	LOTUS Database	35616633
Hippoglossus	FooDB	USDA
Hippoglossus hippoglossus	FooDB	DTU Food
Hippophae rhamnoides	KNApSAcK Database	22123792
Hirschfeldia incana	LOTUS Database	35616633
Homo sapiens	LOTUS Database	35616633
Hoplostethus atlanticus	FooDB	USDA
Hordeum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Houttuynia cordata	LOTUS Database	35616633
Hoya latifolia	LOTUS Database	35616633
Hyoscyamus muticus	LOTUS Database	35616633
Hypericum perforatum	LOTUS Database	35616633
Hyssopus officinalis L.	FooDB	FooDB
Ictalurus punctatus	FooDB	USDA
Illicium verum	FooDB	FooDB
Inezia integrifolia	LOTUS Database	35616633
Ipomoea aquatica	FooDB	FooDB
Ipomoea batatas	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Isatis tinctoria	LOTUS Database	35616633
Jasminum auriculatum	KNApSAcK Database	22123792
Jodina rhombifolia	LOTUS Database	35616633
Juglans	FooDB	DTU Food
Juglans ailanthifolia	FooDB	FooDB
Juglans cinerea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Juglans nigra L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Juglans regia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lablab purpureus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lactarius deliciosus	LOTUS Database	35616633
Lactuca sativa	FooDB	15986496
Lactuca serriola	LOTUS Database	35616633
Lagenaria siceraria	FooDB	FooDB
Lagopus muta	FooDB	DTU Food
Lallemantia iberica	LOTUS Database	35616633
Lallemantia royleana	LOTUS Database	35616633
Lantana ukambensis	LOTUS Database	35616633
Larix gmelini	LOTUS Database	35616633
Lathraea squamaria	LOTUS Database	35616633
Lathyrus sativus	FooDB	FooDB
Laurus nobilis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lemna aequinoctialis	LOTUS Database	35616633
Lens culinaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lentinus edodes	FooDB	FooDB
Lepidium meyenii	LOTUS Database	35616633
Lepidium meyenii Maca	KNApSAcK Database	22123792
Lepidium sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Leporidae	FooDB	DTU Food
Leptolyngbya tenuis	LOTUS Database	35616633
Lepus timidus	FooDB	DTU Food
Levisticum officinale	FooDB	FooDB
Ligularia macrophylla	LOTUS Database	35616633
Ligustrum lucidum	LOTUS Database	35616633
Limanda limanda	FooDB	DTU Food
Linum usitatissimum	KNApSAcK Database	22123792
Litchi chinensis	FooDB	DTU Food
Lota lota	FooDB	DTU Food
Luffa acutangula	LOTUS Database	35616633
Luffa aegyptiaca	FooDB	FooDB
Lupinus	FooDB	FooDB
Lupinus albus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lycium chinense	KNApSAcK Database	22123792
Macadamia	FooDB	FooDB
Macadamia tetraphylla	FooDB	FooDB
Macrococculus pomiferus	LOTUS Database	35616633
Malpighia emarginata	FooDB	FooDB
Malus	FooDB	DTU Food
Malus pumila	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Malva sylvestris	LOTUS Database	35616633
Mammea americana	FooDB	FooDB
Mangifera indica	KNApSAcK Database	22123792
Manihot esculenta	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Manilkara zapota	FooDB	FooDB
Maranta arundinacea	FooDB	FooDB
Matricaria recutita	FooDB	FooDB
Matteuccia struthiopteris	FooDB	FooDB
Medicago sativa	FooDB	DTU Food
Melanogrammus aeglefinus	FooDB	DTU Food
Meleagris gallopavo	FooDB	DTU Food
Melissa officinalis L.	FooDB	FooDB
Mentha	FooDB	FooDB
Mentha aquatica	FooDB	FooDB
Mentha arvensis	FooDB	FooDB
Mentha spicata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha x piperita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Merlangius merlangus	FooDB	DTU Food
Mespilus germanica	FooDB	FooDB
Metroxylon sagu	FooDB	FooDB
Micromesistius poutassou	FooDB	DTU Food
Microstomus kitt	FooDB	DTU Food
Mikania goyazensis	LOTUS Database	35616633
Molva molva	FooDB	DTU Food
Momordica charantia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Morchellaceae	FooDB	FooDB
Morella rubra	FooDB	FooDB
Moringa oleifera	FooDB	FooDB
Morus	FooDB	FooDB
Morus nigra	FooDB	FooDB
Mosla chinensis	LOTUS Database	35616633
Mucuna puriens	Plant	KNApSAcK
Mus musculus	LOTUS Database	35616633
Musa acuminata	FooDB	FooDB
Musa paradisiaca	LOTUS Database	35616633
Musa x paradisiaca	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Myrica	FooDB	FooDB
Myristica fragrans	FooDB	DTU Food
Mytilidae	FooDB	DTU Food
Nelumbo	FooDB	FooDB
Nelumbo nucifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Neolitsea hiiranensis	LOTUS Database	35616633
Nepeta cataria	LOTUS Database	35616633
Nephelium lappaceum	FooDB	FooDB
Nephropidae	FooDB	DTU Food
Nephrops norvegicus	FooDB	DTU Food
Nervilia aragoana	LOTUS Database	35616633
Nicotiana tabacum	KNApSAcK Database	22123792
Nigella sativa	LOTUS Database	35616633
Nigella sativa L	KNApSAcK Database	22123792
Nonea macrosperma	LOTUS Database	35616633
Nuphar lutea	FooDB	USDA
Nymphaea alba	KNApSAcK Database	22123792
Ocimum basilicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Octopus vulgaris	FooDB	DTU Food
Oecophylla smaragdina	LOTUS Database	35616633
Oenothera biennis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Olea europaea	FooDB	DTU Food
Oleandra wallichii	LOTUS Database	35616633
Oncorhynchus gorbuscha	FooDB	USDA
Oncorhynchus kisutch	FooDB	USDA
Oncorhynchus mykiss	FooDB	DTU Food
Oncorhynchus nerka	FooDB	USDA
Ononis natrix	LOTUS Database	35616633
Ophiocordyceps sinensis	Fungi	KNApSAcK
Opuntia	FooDB	DTU Food
Opuntia cochenillifera	FooDB	FooDB
Opuntia macrorhiza	FooDB	FooDB
Origanum majorana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Origanum onites	FooDB	FooDB
Origanum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Origanum X majoricum	FooDB	FooDB
Oryza rufipogon	FooDB	FooDB
Oryza sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ovis aries	FooDB	DTU Food
Pachyrhizus erosus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Panax ginseng	FooDB	FooDB
Pangium edule	FooDB	FooDB
Panicum miliaceum	FooDB	DTU Food
Papaver	FooDB	DTU Food
Passiflora edulis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pastinaca sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pediomelum esculentum	FooDB	FooDB
Peperomia bracteata	LOTUS Database	35616633
Perciformes	FooDB	DTU Food
Perideridia oregana	FooDB	FooDB
Perilla frutescens	LOTUS Database	35616633
Perilla frutescens var.arguta	KNApSAcK Database	22123792
Persea americana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Petasites japonicus	FooDB	FooDB
Petroselinum crispum	FooDB	DTU Food
Phaseolus coccineus	FooDB	FooDB
Phaseolus lunatus	FooDB	FooDB
Phaseolus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phoenix dactylifera	FooDB	DTU Food
Photinia melanocarpa	FooDB	FooDB
Phyllostachys edulis	FooDB	DTU Food
Physalis	FooDB	DTU Food
Physalis philadelphica var. immaculata	FooDB	FooDB
Phytolacca americana	FooDB	FooDB
Picea jezoensis	LOTUS Database	35616633
Picea obovata	LOTUS Database	35616633
Pimenta dioica	FooDB	FooDB
Pimpinella anisum	FooDB	FooDB
Pinus	FooDB	DTU Food
Pinus edulis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pinus resinosa	LOTUS Database	35616633
Pinus sibirica	KNApSAcK Database	22123792
Piper nigrum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pistacia vera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pisum sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Plagiochila porelloides	LOTUS Database	35616633
Plantago ovata	LOTUS Database	35616633
Platycodon grandiflorus	LOTUS Database	35616633
Pleuronectidae	FooDB	DTU Food
Pleuronectiformes	FooDB	DTU Food
Pleurotus ostreatus	FooDB	DTU Food
Pollachius	FooDB	DTU Food
Polygonum alpinum	FooDB	FooDB
Polypodium aureum	LOTUS Database	35616633
Pongamia pinnata	LOTUS Database	35616633
Populus tremula	LOTUS Database	35616633
Portulaca oleracea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Potentilla asiatica	KNApSAcK Database	22123792
Potentilla desertorum	KNApSAcK Database	22123792
Potentilla orientalis	KNApSAcK Database	22123792
Poterium polygamum	-	KNApSAcK
Pouteria sapota	FooDB	FooDB
Premna microphylla	LOTUS Database	35616633
Primula pulverulenta	LOTUS Database	35616633
Prunus armeniaca	KNApSAcK Database	22123792
Prunus avium	FooDB	FooDB
Prunus avium L.	FooDB	DTU Food
Prunus cerasus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus domestica	FooDB	DTU Food
Prunus dulcis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus mume	LOTUS Database	35616633
Prunus persica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus persica var. nucipersica	FooDB	DTU Food
Prunus persica var. persica	FooDB	FooDB
Prunus tomentosa	FooDB	FooDB
Prunus virginiana	FooDB	FooDB
Pseudostellaria heterophylla	LOTUS Database	35616633
Psidium cattleianum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Psidium guajava	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Psophocarpus tetragonolobus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Psoralea corylifolia	KNApSAcK Database	22123792
Punica granatum	KNApSAcK Database	22123792
Pyrus communis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pyrus pyrifolia	FooDB	FooDB
Quercus	FooDB	FooDB
Rana temporaria	LOTUS Database	35616633
Ranidae	FooDB	DTU Food
Raphanus sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Raphanus sativus var. longipinnatus	FooDB	DTU Food
Raphanus sativus var. sativus	FooDB	FooDB
Reinhardtius hippoglossoides	FooDB	DTU Food
Rheum rhabarbarum	FooDB	DTU Food
Rhodotorula glutinis	LOTUS Database	35616633
Ribes aureum	FooDB	FooDB
Ribes glandulosum	FooDB	FooDB
Ribes nigrum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ribes rubrum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ribes uva-crispa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Rosa	FooDB	DTU Food
Rosa canina	LOTUS Database	35616633
Rosa platyacantha	LOTUS Database	35616633
Rosa taiwanensis	LOTUS Database	35616633
Rosa transmorrisonensis	LOTUS Database	35616633
Rubus arcticus	FooDB	FooDB
Rubus chamaemorus	FooDB	FooDB
Rubus idaeus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Rubus occidentalis	FooDB	FooDB
Rubus spectabilis	FooDB	FooDB
Rumex	FooDB	FooDB
Rumex acetosa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Rumex articus	FooDB	FooDB
Saccharina japonica	FooDB	DTU Food
Sagittaria latifolia	FooDB	FooDB
Salix herbacea	LOTUS Database	35616633
Salix pulchra	FooDB	FooDB
Salmea scandens	LOTUS Database	35616633
Salmo salar	FooDB	USDA
Salmonidae	FooDB	DTU Food
Salvelinus	FooDB	DTU Food
Salvelinus namaycush	FooDB	DTU Food
Salvia elegans	FooDB	FooDB
Salvia fruticosa	LOTUS Database	35616633
Salvia hispanica	FooDB	FooDB
Salvia miltiorrhiza	LOTUS Database	35616633
Salvia officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salvia rosmarinus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salvia trijuga	LOTUS Database	35616633
Sambucus nigra	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sambucus nigra L.	FooDB	DTU Food
Sander lucioperca	FooDB	DTU Food
Satureja hortensis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Satureja montana	FooDB	FooDB
Saussurea medusa	LOTUS Database	35616633
Schotia brachypetala	LOTUS Database	35616633
Scombridae	FooDB	DTU Food
Scophthalmus maximus	FooDB	DTU Food
Scorzonera hispanica	FooDB	DTU Food
Scrophularia nodosa	LOTUS Database	35616633
Scurrula atropurpurea	KNApSAcK Database	22123792
Scurrura atropurpurea	-	KNApSAcK
Sebastes alutus	FooDB	DTU Food
Sebastes viviparus	FooDB	DTU Food
Secale cereale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sechium edule	FooDB	DTU Food
Senna alexandrina	LOTUS Database	35616633
Senna didymobotrya	LOTUS Database	35616633
Serenoa repens	LOTUS Database	35616633
Sesamum indicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sesbania bispinosa	FooDB	FooDB
Sideritis taurica	LOTUS Database	35616633
Siluriformes	FooDB	DTU Food
Silybum marianum	KNApSAcK Database	22123792
Sinapis alba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sisymbrium	FooDB	FooDB
Solanum lycopersicum	FooDB	DTU Food
Solanum lycopersicum var. cerasiforme	FooDB	FooDB
Solanum lycopersicum var. lycopersicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solanum melongena	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solanum quitoense	FooDB	FooDB
Solanum tuberosum	KNApSAcK Database	22123792
Sorbus aucuparia	FooDB	FooDB
Sorghum bicolor	FooDB	USDA
Spinacia oleracea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Squalus acanthias	FooDB	DTU Food
Sterculia tragacantha	LOTUS Database	35616633
Stilpnopappus tomentosus	LOTUS Database	35616633
Stuckenia pectinata	LOTUS Database	35616633
Suaeda aegyptiaca	LOTUS Database	35616633
Sus scrofa domestica	FooDB	DTU Food
Syzygium aromaticum	FooDB	FooDB
Syzygium cumini	FooDB	FooDB
Syzygium jambos	FooDB	FooDB
Talaromyces flavus	LOTUS Database	35616633
Tamarindus indica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Taonia atomaria	LOTUS Database	35616633
Taraxacum officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Taxus mairei	LOTUS Database	35616633
Tetragonia tetragonioides	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Thalictrum revolutum	LOTUS Database	35616633
Thelesperma	FooDB	FooDB
Theobroma cacao	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Thunnus	FooDB	DTU Food
Thymus pulegioides	FooDB	FooDB
Thymus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tilia cordata	FooDB	KNAPSACK
Tilia cordata Mill.	KNApSAcK Database	22123792
Tilia L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tragopogon porrifolius	FooDB	FooDB
Treculia africana	LOTUS Database	35616633
Trichosanthes kirilowii	KNApSAcK Database	22123792
Trichosanthes rosthornii	KNApSAcK Database	22123792
Trifolium alexandrinum	LOTUS Database	35616633
Trigonella foenum-graecum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Trisopterus esmarkii	FooDB	DTU Food
Triticum	FooDB	DTU Food
Triticum aestivum	KNApSAcK Database	22123792
Triticum durum	FooDB	DTU Food
Triticum spelta	FooDB	USDA
Triticum turanicum	FooDB	USDA
Typha angustifolia	FooDB	FooDB
Typha domingensis	LOTUS Database	35616633
Typha domingensis P.	KNApSAcK Database	22123792
Ulva fasciata	LOTUS Database	35616633
Vaccinium	FooDB	DTU Food
Vaccinium angustifolium	FooDB	FooDB
Vaccinium angustifolium X Vaccinium corymbosum	FooDB	FooDB
Vaccinium arboreum	FooDB	FooDB
Vaccinium corymbosum	FooDB	FooDB
Vaccinium deliciosum	FooDB	FooDB
Vaccinium elliottii	FooDB	FooDB
Vaccinium macrocarpon	FooDB	FooDB
Vaccinium myrtilloides	FooDB	FooDB
Vaccinium myrtillus	FooDB	DTU Food
Vaccinium ovalifolium	FooDB	FooDB
Vaccinium ovatum	FooDB	FooDB
Vaccinium oxycoccos	FooDB	FooDB
Vaccinium parvifolium	FooDB	FooDB
Vaccinium reticulatum	FooDB	FooDB
Vaccinium stamineum	FooDB	FooDB
Vaccinium uliginosum	FooDB	FooDB
Vaccinium vitis-idaea	FooDB	DTU Food
Valerianella locusta	FooDB	FooDB
Vanilla	FooDB	FooDB
Ventilago denticulata	LOTUS Database	35616633
Verbena officinalis	FooDB	FooDB
Viburnum edule	FooDB	FooDB
Vicia faba	KNApSAcK Database	22123792
Vigna aconitifolia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna angularis	FooDB	DTU Food
Vigna mungo	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna radiata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna subterranea	LOTUS Database	35616633
Vigna umbellata	FooDB	FooDB
Vigna unguiculata	FooDB	FooDB
Vigna unguiculata ssp. cylindrica	FooDB	FooDB
Vigna unguiculata ssp. unguiculata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna unguiculata var. sesquipedalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vitellaria paradoxa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vitis	FooDB	DTU Food
Vitis aestivalis	FooDB	FooDB
Vitis labrusca	FooDB	FooDB
Vitis rotundifolia	FooDB	FooDB
Vitis vinifera	LOTUS Database	35616633
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Wedelia calycina	LOTUS Database	35616633
Withania somnifera	Plant	KNApSAcK
Xanthosoma sagittifolium	FooDB	FooDB
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zingiber officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zizania	FooDB	FooDB
Zizania aquatica	FooDB	FooDB
Ziziphus spina-christi	LOTUS Database	35616633
Ziziphus zizyphus	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Cordyceps sinensis	KNApSAcK Database	22123792
Homo sapiens (Serum)	KNApSAcK Database	22123792
Psalliota bispora	KNApSAcK Database	22123792

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 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-16.5 °C	Not Available
Boiling Point	230.00 to 231.00 °C. @ 1.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.12 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.46	Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.

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

External Links

HMDB ID

HMDB0001388

DrugBank ID

DB00132

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1045911

References

General References

Richieri GV, Ogata RT, Kleinfeld AM: Equilibrium constants for the binding of fatty acids with fatty acid-binding proteins from adipocyte, intestine, heart, and liver measured with the fluorescent probe ADIFAB. J Biol Chem. 1994 Sep 30;269(39):23918-30. [PubMed:7929039 ]
Bajaj M, Suraamornkul S, Romanelli A, Cline GW, Mandarino LJ, Shulman GI, DeFronzo RA: Effect of a sustained reduction in plasma free fatty acid concentration on intramuscular long-chain fatty Acyl-CoAs and insulin action in type 2 diabetic patients. Diabetes. 2005 Nov;54(11):3148-53. [PubMed:16249438 ]
Christensen JH, Fabrin K, Borup K, Barber N, Poulsen J: Prostate tissue and leukocyte levels of n-3 polyunsaturated fatty acids in men with benign prostate hyperplasia or prostate cancer. BJU Int. 2006 Feb;97(2):270-3. [PubMed:16430627 ]
Attar-Bashi NM, Frauman AG, Sinclair AJ: Alpha-linolenic acid and the risk of prostate cancer. What is the evidence? J Urol. 2004 Apr;171(4):1402-7. [PubMed:15017185 ]
Rastogi SK, Singh J: Effect of chemical penetration enhancer and iontophoresis on the in vitro percutaneous absorption enhancement of insulin through porcine epidermis. Pharm Dev Technol. 2005;10(1):97-104. [PubMed:15776817 ]
Allman MA, Pena MM, Pang D: Supplementation with flaxseed oil versus sunflowerseed oil in healthy young men consuming a low fat diet: effects on platelet composition and function. Eur J Clin Nutr. 1995 Mar;49(3):169-78. [PubMed:7774533 ]
Fokkema MR, Brouwer DA, Hasperhoven MB, Martini IA, Muskiet FA: Short-term supplementation of low-dose gamma-linolenic acid (GLA), alpha-linolenic acid (ALA), or GLA plus ALA does not augment LCP omega 3 status of Dutch vegans to an appreciable extent. Prostaglandins Leukot Essent Fatty Acids. 2000 Nov;63(5):287-92. [PubMed:11090255 ]
Becker CC, Lund P, Holmer G, Jensen H, Sandstrom B: Effects of butter oil blends with increased concentrations of stearic, oleic and linolenic acid on blood lipids in young adults. Eur J Clin Nutr. 1999 Jul;53(7):535-41. [PubMed:10452408 ]
Jones DB, Scaretto L, Carter R, Mann JI: Glucose, insulin and platelet fatty acids following myocardial infarction: an association with infarct size. Diabete Metab. 1987 Jul-Aug;13(4):463-6. [PubMed:3315767 ]
Crastes de Paulet A, Babin F, Billeaud C, Bougle D, Sarda P, Mendy F: [Biological effects on premature neonates of a milk formula enriched with alpha-linolenic acid: a multicenter study]. Bull Acad Natl Med. 1994 Feb;178(2):267-73; discussion 273-8. [PubMed:7913655 ]
Li D, Sinclair A, Wilson A, Nakkote S, Kelly F, Abedin L, Mann N, Turner A: Effect of dietary alpha-linolenic acid on thrombotic risk factors in vegetarian men. Am J Clin Nutr. 1999 May;69(5):872-82. [PubMed:10232625 ]
Bhatia KS, Singh J: Effect of linolenic acid/ethanol or limonene/ethanol and iontophoresis on the in vitro percutaneous absorption of LHRH and ultrastructure of human epidermis. Int J Pharm. 1999 Apr 15;180(2):235-50. [PubMed:10370194 ]
Baylin A, Kabagambe EK, Ascherio A, Spiegelman D, Campos H: Adipose tissue alpha-linolenic acid and nonfatal acute myocardial infarction in Costa Rica. Circulation. 2003 Apr 1;107(12):1586-91. Epub 2003 Mar 10. [PubMed:12668490 ]
Williard DE, Nwankwo JO, Kaduce TL, Harmon SD, Irons M, Moser HW, Raymond GV, Spector AA: Identification of a fatty acid delta6-desaturase deficiency in human skin fibroblasts. J Lipid Res. 2001 Apr;42(4):501-8. [PubMed:11290821 ]
Campbell FM, Gordon MJ, Dutta-Roy AK: Preferential uptake of long chain polyunsaturated fatty acids by isolated human placental membranes. Mol Cell Biochem. 1996 Feb 9;155(1):77-83. [PubMed:8717442 ]
Cunnane SC, Hamadeh MJ, Liede AC, Thompson LU, Wolever TM, Jenkins DJ: Nutritional attributes of traditional flaxseed in healthy young adults. Am J Clin Nutr. 1995 Jan;61(1):62-8. [PubMed:7825540 ]
Lauritzen I, Blondeau N, Heurteaux C, Widmann C, Romey G, Lazdunski M: Polyunsaturated fatty acids are potent neuroprotectors. EMBO J. 2000 Apr 17;19(8):1784-93. [PubMed:10775263 ]
Cho E, Hung S, Willett WC, Spiegelman D, Rimm EB, Seddon JM, Colditz GA, Hankinson SE: Prospective study of dietary fat and the risk of age-related macular degeneration. Am J Clin Nutr. 2001 Feb;73(2):209-18. [PubMed:11157315 ]
Brouwer IA, Katan MB, Zock PL: Dietary alpha-linolenic acid is associated with reduced risk of fatal coronary heart disease, but increased prostate cancer risk: a meta-analysis. J Nutr. 2004 Apr;134(4):919-22. [PubMed:15051847 ]

Showing NP-Card for Alpha-Linolenic acid (NP0000694)

MOL for NP0000694 (Alpha-Linolenic acid)

3D MOL for NP0000694 (Alpha-Linolenic acid)

3D SDF for NP0000694 (Alpha-Linolenic acid)

3D-SDF for NP0000694 (Alpha-Linolenic acid)

PDB for NP0000694 (Alpha-Linolenic acid)

3D PDB for NP0000694 (Alpha-Linolenic acid)

SMILES for NP0000694 (Alpha-Linolenic acid)

INCHI for NP0000694 (Alpha-Linolenic acid)

Structure for NP0000694 (Alpha-Linolenic acid)

3D Structure for NP0000694 (Alpha-Linolenic acid)