MiMeDB: Showing metabocard for Erucic acid (MMDBc0048107)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 21:50:53 UTC

Update Date

2022-12-15 22:52:17 UTC

Metabolite ID

MMDBc0048107

Metabolite Identification

Common Name

Erucic acid

Description

Erucic acid is a 22-carbon, monounsaturated omega-9 fatty acid found mainly in the Brassica family of plants such as canola, rapeseed, wallflower seed, mustard seed as well as Brussels spouts and broccoli. Some Brassica cultivars can have up to 40 to 50 percent of their oil recovered as erucic acid. Erucic acid is also known as cis-13-docosenoic acid. The trans isomer is known as brassidic acid. Erucic acid occurs in nature only along with bitter-tasting compounds. Erucic acid has many of the same uses as mineral oils but with the advantage that it is more readily bio-degradable. Its high tolerance to temperature makes it suitable for transmission oil. Erucic acid‚Äôs ability to polymerize and dry means it can be - and is - used as a binder for oil paints. Increased levels of eicosenoic acid (20:Ln9) and erucic acid (22:1N9) have been found in the red blood cell membranes of autistic subjects with developmental regression (PMID: 16581239 ). Erucic acid is broken down long-chain acyl-coenzyme A (CoA) dehydrogenase, which is produced in the liver. This enzyme breaks this long chain fatty acid into shorter-chain fatty acids. Human infants have relatively low amounts of this enzyme and because of this, babies should not be given foods high in erucic acid. Food-grade rapeseed oil (also known as canola oil) is regulated to a maximum of 2% erucic acid by weight in the US and 5% in the EU, with special regulations for infant food. Canola was bred from rapeseed cultivars of B. napus and B. rapa at the University of Manitoba, Canada. Canola oil is derived from a variety of rapeseed that is low in erucic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292223502D          

 65 64  0  0  0  0            999 V2000
    3.3296    3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7586    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7586    2.7474    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8433    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1028    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8172    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5578    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2722    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5317    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2462    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9867    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7012    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9607    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0454    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6751    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4156    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7599    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1301    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3896    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1041    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8446    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5591    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8185    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9033    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5330    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2735    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6177    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9880    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2475    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467    3.9849    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   13.3322    2.7474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441    4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8677    4.8578    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4974    5.4991    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296    5.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5060    5.1744    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8763    4.5331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296    6.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1532    6.0953    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7830    6.7366    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151    6.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7915    6.4119    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1618    5.7706    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151    7.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4387    7.3328    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0685    7.9741    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9007    7.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0771    7.6494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4473    7.0081    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9007    8.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243    8.5703    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3540    9.2116    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862    8.9349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5987    9.6493    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    9.3474    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7737    8.2204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
  2 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 41 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 44 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
 47 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  1  0  0  0  0
 50 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 53 56  1  0  0  0  0
 56 57  1  0  0  0  0
 56 58  1  0  0  0  0
 56 59  1  0  0  0  0
 59 60  1  0  0  0  0
 59 61  1  0  0  0  0
 59 62  1  0  0  0  0
 62 63  1  0  0  0  0
 62 64  1  0  0  0  0
 62 65  1  0  0  0  0
M  CHG  1  39  -1
M  END


  Mrv1652304292223502D          

 65 64  0  0  0  0            999 V2000
    3.3296    3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7586    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7586    2.7474    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8433    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1028    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8172    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5578    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2722    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5317    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2462    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9867    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7012    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9607    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0454    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6751    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4156    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7599    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1301    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3896    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1041    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8446    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5591    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8185    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9033    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5330    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2735    2.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6177    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9880    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2475    4.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467    3.9849    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   13.3322    2.7474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441    4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8677    4.8578    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4974    5.4991    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296    5.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5060    5.1744    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8763    4.5331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296    6.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1532    6.0953    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7830    6.7366    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151    6.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7915    6.4119    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1618    5.7706    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151    7.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4387    7.3328    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0685    7.9741    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9007    7.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0771    7.6494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4473    7.0081    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9007    8.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243    8.5703    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3540    9.2116    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862    8.9349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5987    9.6493    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    9.3474    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7737    8.2204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
  2 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 41 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 44 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
 47 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  1  0  0  0  0
 50 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 53 56  1  0  0  0  0
 56 57  1  0  0  0  0
 56 58  1  0  0  0  0
 56 59  1  0  0  0  0
 59 60  1  0  0  0  0
 59 61  1  0  0  0  0
 59 62  1  0  0  0  0
 62 63  1  0  0  0  0
 62 64  1  0  0  0  0
 62 65  1  0  0  0  0
M  CHG  1  39  -1
M  END
> <DATABASE_ID>
MMDBc0048107

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(/[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([O-])=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h9-10H,2-8,11-21H2,1H3,(H,23,24)/p-1/b10-9-

> <INCHI_KEY>
DPUOLQHDNGRHBS-KTKRTIGZSA-M

> <FORMULA>
C22H41O2

> <MOLECULAR_WEIGHT>
337.569

> <EXACT_MASS>
337.31120414

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
44.78868648181294

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(13Z)-docos-13-enoate

> <ALOGPS_LOGP>
9.11

> <JCHEM_LOGP>
8.562073111

> <ALOGPS_LOGS>
-7.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952019655228562

> <JCHEM_POLAR_SURFACE_AREA>
40.129999999999995

> <JCHEM_REFRACTIVITY>
116.64329999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.06e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
erucate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  H   UNK     0       6.215   6.668   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       7.549   7.438   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.883   6.668   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0       8.883   5.128   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0      10.216   7.438   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0      10.907   8.815   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0       9.525   8.815   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0      10.859   5.292   0.000  0.00  0.00           H+0
HETATM   10  H   UNK     0      12.241   5.292   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0      12.884   7.438   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0      13.575   8.815   0.000  0.00  0.00           H+0
HETATM   13  H   UNK     0      12.193   8.815   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0      14.217   6.668   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0      13.526   5.292   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0      14.909   5.292   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0      15.551   7.438   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0      16.242   8.815   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0      14.860   8.815   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0      16.885   6.668   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      16.194   5.292   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      17.576   5.292   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0      18.218   7.438   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0      18.910   8.815   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      17.527   8.815   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0      19.552   6.668   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0      18.861   5.292   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      20.243   5.292   0.000  0.00  0.00           H+0
HETATM   29  C   UNK     0      20.886   7.438   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0      21.577   8.815   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      20.195   8.815   0.000  0.00  0.00           H+0
HETATM   32  C   UNK     0      22.219   6.668   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0      21.528   5.292   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      22.911   5.292   0.000  0.00  0.00           H+0
HETATM   35  C   UNK     0      23.553   7.438   0.000  0.00  0.00           C+0
HETATM   36  H   UNK     0      24.244   8.815   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0      22.862   8.815   0.000  0.00  0.00           H+0
HETATM   38  C   UNK     0      24.887   6.668   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      26.220   7.438   0.000  0.00  0.00           O-1
HETATM   40  O   UNK     0      24.887   5.128   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       7.549   8.978   0.000  0.00  0.00           C+0
HETATM   42  H   UNK     0       9.086   9.068   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0       8.395  10.265   0.000  0.00  0.00           H+0
HETATM   44  C   UNK     0       6.215   9.748   0.000  0.00  0.00           C+0
HETATM   45  H   UNK     0       4.678   9.659   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0       5.369   8.462   0.000  0.00  0.00           H+0
HETATM   47  C   UNK     0       6.215  11.288   0.000  0.00  0.00           C+0
HETATM   48  H   UNK     0       7.753  11.378   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0       7.062  12.575   0.000  0.00  0.00           H+0
HETATM   50  C   UNK     0       4.882  12.058   0.000  0.00  0.00           C+0
HETATM   51  H   UNK     0       3.344  11.969   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.035  10.772   0.000  0.00  0.00           H+0
HETATM   53  C   UNK     0       4.882  13.598   0.000  0.00  0.00           C+0
HETATM   54  H   UNK     0       6.419  13.688   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0       5.728  14.885   0.000  0.00  0.00           H+0
HETATM   56  C   UNK     0       3.548  14.368   0.000  0.00  0.00           C+0
HETATM   57  H   UNK     0       2.011  14.279   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.702  13.082   0.000  0.00  0.00           H+0
HETATM   59  C   UNK     0       3.548  15.908   0.000  0.00  0.00           C+0
HETATM   60  H   UNK     0       5.085  15.998   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.394  17.195   0.000  0.00  0.00           H+0
HETATM   62  C   UNK     0       2.214  16.678   0.000  0.00  0.00           C+0
HETATM   63  H   UNK     0       2.984  18.012   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.881  17.448   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.444  15.345   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   41                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32   36   37   38                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   35   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41    2   42   43   44                                             
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   41   45   46   47                                             
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47   44   48   49   50                                             
CONECT   48   47                                                            
CONECT   49   47                                                            
CONECT   50   47   51   52   53                                             
CONECT   51   50                                                            
CONECT   52   50                                                            
CONECT   53   50   54   55   56                                             
CONECT   54   53                                                            
CONECT   55   53                                                            
CONECT   56   53   57   58   59                                             
CONECT   57   56                                                            
CONECT   58   56                                                            
CONECT   59   56   60   61   62                                             
CONECT   60   59                                                            
CONECT   61   59                                                            
CONECT   62   59   63   64   65                                             
CONECT   63   62                                                            
CONECT   64   62                                                            
CONECT   65   62                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  128    0
END

Synonyms

Value	Source
(13Z)-Docosenoate	ChEBI
(22:1n9)	ChEBI
(Z)-13-Docosenoate	ChEBI
cis-Delta(13)-Docosenoate	ChEBI
Docos-13C-enoate	ChEBI
(13Z)-Docosenoic acid	Generator
(Z)-13-Docosenoic acid	Generator
cis-delta(13)-Docosenoic acid	Generator
cis-Δ(13)-docosenoate	Generator
cis-Δ(13)-docosenoic acid	Generator
Docos-13C-enoic acid	Generator
Erucic acid	Generator

Molecular Formula

C₂₂H₄₁O₂

Average Mass

337.569

Monoisotopic Mass

337.31120414

IUPAC Name

(13Z)-docos-13-enoate

Traditional Name

erucate

CAS Registry Number

112-86-7

SMILES

[H]\C(=C(/[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([O-])=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h9-10H,2-8,11-21H2,1H3,(H,23,24)/p-1/b10-9-

InChI Key

DPUOLQHDNGRHBS-KTKRTIGZSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents

Substituents

Very long-chain 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
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid anion (CHEBI:32393 )
unsaturated fatty acid anion (CHEBI:32393 )
docosenoate (CHEBI:32393 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.1e-05 g/L	ALOGPS
logP	9.11	ALOGPS
logP	8.56	ChemAxon
logS	-7.5	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.13 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	116.64 m³·mol⁻¹	ChemAxon
Polarizability	44.79 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Adrenal Gland
Blood
Feces
Placenta

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0004647	13Z-docosenoyl-CoA	Coenzyme A	Not Available	RE3239C	VMH	0
MMDBr0005133	Adenosine triphosphate	Adenosine monophosphate	Solute carrier family 27 (fatty acid transporter), member 1	Absorption Or Uptake of 13-Docosenoic Acid into Cells	VMH	16868315 17901542 16357361 16357361 17495600
MMDBr0006750	Erucic acid	Erucic acid	Not Available	Ce2512Te	VMH	30371894
MMDBr0009245	Adenosine triphosphate	Adenosine monophosphate	Not Available	Long-Chain-Fatty-Acid Coenzyme A Ligase	VMH	30371894
MMDBr0009246	Adenosine triphosphate	ADP	Atp-binding cassette, sub-family a (abc1), member 1	HMR_0321	VMH	30371894
MMDBr0009985	Adenosine triphosphate	Adenosine monophosphate	Not Available	Long-Chain-Fatty-Acid Coenzyme A Ligase	VMH	30371894
MMDBr0010212	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010250	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010787	Erucic acid	Erucic acid	Not Available	HMR_9766	VMH	30371894
MMDBr0036339	PC(14:0/22:1(13Z))	LysoPC(14:0/0:0)	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036520	PC(14:1(9Z)/22:1(13Z))	Erucic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036484	PC(18:1(11Z)/22:1(13Z))	LysoPC(18:1(11Z))	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036470	PC(18:1(9Z)/22:1(13Z))	LysoPC(18:1(9Z))	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036496	PC(18:2(9Z,12Z)/22:1(13Z))	LysoPC(18:2(9Z,12Z))	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036521	PC(18:3(6Z,9Z,12Z)/22:1(13Z))	Erucic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036377	PC(18:3(9Z,12Z,15Z)/22:1(13Z))	LysoPC(18:3(9Z,12Z,15Z)/0:0)	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036522	PC(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))	Erucic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036523	PC(20:0/22:1(13Z))	Erucic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036524	PC(20:1(11Z)/22:1(13Z))	Erucic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036525	PC(20:3(5Z,8Z,11Z)/22:1(13Z))	Erucic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036526	PC(20:3(8Z,11Z,14Z)/22:1(13Z))	Erucic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036923	PC(22:1(13Z)/14:1(9Z))	Erucic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036924	PC(22:1(13Z)/18:1(11Z))	Erucic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036925	PC(22:1(13Z)/18:1(9Z))	Erucic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036926	PC(22:1(13Z)/18:2(9Z,12Z))	Erucic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036927	PC(22:1(13Z)/18:3(6Z,9Z,12Z))	Erucic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036928	PC(22:1(13Z)/18:3(9Z,12Z,15Z))	Erucic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036929	PC(22:1(13Z)/18:4(6Z,9Z,12Z,15Z))	Erucic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036930	PC(22:1(13Z)/20:0)	Erucic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036931	PC(22:1(13Z)/20:1(11Z))	Erucic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036932	PC(22:1(13Z)/20:3(5Z,8Z,11Z))	Erucic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036933	PC(22:1(13Z)/20:3(8Z,11Z,14Z))	Erucic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036934	PC(22:1(13Z)/14:0)	Erucic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0038259	MG(22:1(13Z)/0:0/0:0)	Glycerol	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0038708	Erucic acid	13Z-docosenoyl-CoA	Long-chain-fatty-acid--CoA ligase 1	Hydrolysis; Ligation	RHEA	34755880
MMDBr0038980	Erucic acid	N-(13Z-Docosenoyl)-4R-hydroxysphinganine	Alkaline ceramidase YPC1	Hydrolysis	RHEA	34755880
MMDBr0039039	MG(22:1(13Z)/0:0/0:0)	Erucic acid	Monoacylglycerol lipase	Lipid (ester bond) hydrolysis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Adrenomyeloneuropathy	Increased	Association	Human Blood	HMDB	8350883
Isovaleric acidemia	Decreased	Association	Human Blood	HMDB	27329611

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	150.0		125.0	160.0	uM	Adult (>18 years old)	Both	Adrenomyeloneuropathy	HMDB	8350883
Human Blood	Detected and Quantified	3.4	2.2			uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	HMDB	27329611
Human Blood	Detected and Quantified	0.028	0.002			uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	1.264	1.590			uM	Adult (>18 years old)	Both	Normal	HMDB	18953024
Human Blood	Detected and Quantified	1.264	1.590			uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	20.2	6.8			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	27329611
Human Adrenal gland	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 Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4574385

KEGG Compound ID

Not Available

BioCyc ID

CPD-14292

BiGG ID

Not Available

Wikipedia Link

Erucic acid

METLIN ID

Not Available

PubChem Compound

5460999

PDB ID

Not Available

ChEBI ID

32393

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Rizzo WB, Leshner RT, Odone A, Dammann AL, Craft DA, Jensen ME, Jennings SS, Davis S, Jaitly R, Sgro JA: Dietary erucic acid therapy for X-linked adrenoleukodystrophy. Neurology. 1989 Nov;39(11):1415-22. doi: 10.1212/wnl.39.11.1415. [PubMed:2682348 ]
Bu B, Ashwood P, Harvey D, King IB, Water JV, Jin LW: Fatty acid compositions of red blood cell phospholipids in children with autism. Prostaglandins Leukot Essent Fatty Acids. 2006 Apr;74(4):215-21. doi: 10.1016/j.plefa.2006.02.001. [PubMed:16581239 ]
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Showing metabocard for Erucic acid (MMDBc0048107)

MOL for #<Metabolite:0x000055c79a13cc18>

3D MOL for #<Metabolite:0x000055c79a13cc18>

3D SDF for #<Metabolite:0x000055c79a13cc18>

3D-SDF for #<Metabolite:0x000055c79a13cc18>

PDB for #<Metabolite:0x000055c79a13cc18>

3D PDB for #<Metabolite:0x000055c79a13cc18>

SMILES for #<Metabolite:0x000055c79a13cc18>

INCHI for #<Metabolite:0x000055c79a13cc18>

Structure for #<Metabolite:0x000055c79a13cc18>

3D Structure for #<Metabolite:0x000055c79a13cc18>