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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:35 UTC

Update Date

2022-03-07 02:49:12 UTC

HMDB ID

HMDB0002068

Secondary Accession Numbers

HMDB02068

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

HMDB0002068
     RDKit          3D
Erucic acid
 66 65  0  0  0  0  0  0  0  0999 V2000
    8.1745   -2.0910   -0.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0949   -1.1050   -0.5372 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6422    0.2775   -0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6105    1.2971    0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5208    1.3654   -0.9951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4655    2.3870   -0.6140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8209    2.0597    0.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1389    0.6958    0.6716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5523    0.4816    1.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2859    0.3068    2.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2993    0.3106    1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3647   -1.0508    1.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4041   -1.1980    0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5168   -0.2091    0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5036   -0.4269   -0.9467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1453   -1.7482   -0.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8524   -2.2038    0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9923   -1.6234    0.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0525   -0.3600    1.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9598    0.9934    1.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9698    1.5677    0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2605    1.0135   -1.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7546    0.0348   -1.7180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2790    1.6408   -1.9315 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4962   -2.7022   -0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0747   -1.5312   -1.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8318   -2.7863   -1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6011   -1.4949    0.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3556   -1.1209   -1.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4759    0.3355    0.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0894    0.5479   -1.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2427    0.9589    1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0425    2.2915    0.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9699    1.7027   -1.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0379    0.3883   -1.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9650    3.3681   -0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917    2.4696   -1.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5456    2.0237    1.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0585    2.8161    0.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9564   -0.0997    0.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5251    0.5530   -0.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2466    0.4703    2.8515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435    0.1507    3.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4596    1.1062    1.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362    0.6394    0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8074   -1.2613    2.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4313   -1.7956    0.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9738   -1.1513   -0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8333   -2.2162    0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1918    0.8396    0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0341   -0.3328    1.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1904    0.3899   -1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482   -0.3085   -1.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8406   -1.7477   -1.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3852   -2.5440   -1.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1665   -3.3175   -0.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0490   -2.5255    1.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9007   -1.8013    0.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2576   -2.4272    1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2049   -0.4271    2.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9668   -0.3593    2.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0937    1.6633    2.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9371    1.3656    0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9608    1.7478    0.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6485    2.6588   -0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0175    1.0485   -2.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  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  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  0
 17 57  1  0
 18 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 20 62  1  0
 20 63  1  0
 21 64  1  0
 21 65  1  0
 24 66  1  0
M  END


  Mrv1652309042000262D          

 24 23  0  0  0  0            999 V2000
 9995.4484 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1632 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8781 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5929 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3081 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0216 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8485 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5620 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2777 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.9932 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.7067 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.4224 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.1379 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.8535 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.5691 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.7337 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.0189 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.3040 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.5892 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.8744 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.1577 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.4428 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.7279 9997.0199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9990.4428 9998.2571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 16  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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002068

> <DATABASE_NAME>
hmdb

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

> <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)/b10-9-

> <INCHI_KEY>
DPUOLQHDNGRHBS-KTKRTIGZSA-N

> <FORMULA>
C22H42O2

> <MOLECULAR_WEIGHT>
338.5677

> <EXACT_MASS>
338.318480588

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
45.6006376809593

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(13Z)-docos-13-enoic acid

> <ALOGPS_LOGP>
8.97

> <JCHEM_LOGP>
8.562073111

> <ALOGPS_LOGS>
-7.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952019655228562

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
105.80619999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.27e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
erucic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002068
     RDKit          3D
Erucic acid
 66 65  0  0  0  0  0  0  0  0999 V2000
    8.1745   -2.0910   -0.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0949   -1.1050   -0.5372 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6422    0.2775   -0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6105    1.2971    0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5208    1.3654   -0.9951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4655    2.3870   -0.6140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8209    2.0597    0.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1389    0.6958    0.6716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5523    0.4816    1.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2859    0.3068    2.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2993    0.3106    1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3647   -1.0508    1.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4041   -1.1980    0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5168   -0.2091    0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5036   -0.4269   -0.9467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1453   -1.7482   -0.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8524   -2.2038    0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9923   -1.6234    0.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0525   -0.3600    1.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9598    0.9934    1.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9698    1.5677    0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2605    1.0135   -1.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7546    0.0348   -1.7180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2790    1.6408   -1.9315 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4962   -2.7022   -0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0747   -1.5312   -1.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8318   -2.7863   -1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6011   -1.4949    0.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3556   -1.1209   -1.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4759    0.3355    0.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0894    0.5479   -1.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2427    0.9589    1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0425    2.2915    0.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9699    1.7027   -1.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0379    0.3883   -1.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9650    3.3681   -0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917    2.4696   -1.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5456    2.0237    1.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0585    2.8161    0.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9564   -0.0997    0.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5251    0.5530   -0.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2466    0.4703    2.8515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435    0.1507    3.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4596    1.1062    1.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362    0.6394    0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8074   -1.2613    2.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4313   -1.7956    0.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9738   -1.1513   -0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8333   -2.2162    0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1918    0.8396    0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0341   -0.3328    1.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1904    0.3899   -1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482   -0.3085   -1.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8406   -1.7477   -1.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3852   -2.5440   -1.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1665   -3.3175   -0.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0490   -2.5255    1.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9007   -1.8013    0.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2576   -2.4272    1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2049   -0.4271    2.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9668   -0.3593    2.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0937    1.6633    2.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9371    1.3656    0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9608    1.7478    0.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6485    2.6588   -0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0175    1.0485   -2.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  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  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  0
 17 57  1  0
 18 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 20 62  1  0
 20 63  1  0
 21 64  1  0
 21 65  1  0
 24 66  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8658.1708661.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8659.5058661.872   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8660.8398661.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8662.1738661.872   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8663.5088661.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8664.8408661.872   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8666.3848661.872   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8667.7168661.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8669.0528661.872   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8670.3878661.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8671.7198661.872   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8673.0558661.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8674.3918661.872   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8675.7278661.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8677.0628661.872   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8656.8368661.872   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8655.5028661.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8654.1678661.872   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8652.8338661.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8651.4998661.872   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8650.1618661.104   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8648.8278661.872   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8647.4928661.104   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0    8648.8278663.413   0.000  0.00  0.00           O+0
CONECT    1    2   16                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16    1   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0002068
HETATM    1  C1  UNL     1       8.175  -2.091  -0.948  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.095  -1.105  -0.537  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.642   0.277  -0.394  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.610   1.297   0.021  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.521   1.365  -0.995  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.465   2.387  -0.614  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.821   2.060   0.707  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.139   0.696   0.672  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.552   0.482   1.992  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.286   0.307   2.210  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.299   0.311   1.112  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.365  -1.051   1.124  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.404  -1.198   0.051  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.517  -0.209   0.157  1.00  0.00           C  
HETATM   15  C15 UNL     1      -3.504  -0.427  -0.947  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.145  -1.748  -0.983  1.00  0.00           C  
HETATM   17  C17 UNL     1      -4.852  -2.204   0.184  1.00  0.00           C  
HETATM   18  C18 UNL     1      -5.992  -1.623   0.866  1.00  0.00           C  
HETATM   19  C19 UNL     1      -6.052  -0.360   1.557  1.00  0.00           C  
HETATM   20  C20 UNL     1      -5.960   0.993   1.059  1.00  0.00           C  
HETATM   21  C21 UNL     1      -6.970   1.568   0.157  1.00  0.00           C  
HETATM   22  C22 UNL     1      -7.260   1.014  -1.139  1.00  0.00           C  
HETATM   23  O1  UNL     1      -6.755   0.035  -1.718  1.00  0.00           O  
HETATM   24  O2  UNL     1      -8.279   1.641  -1.931  1.00  0.00           O  
HETATM   25  H1  UNL     1       8.496  -2.702  -0.062  1.00  0.00           H  
HETATM   26  H2  UNL     1       9.075  -1.531  -1.263  1.00  0.00           H  
HETATM   27  H3  UNL     1       7.832  -2.786  -1.736  1.00  0.00           H  
HETATM   28  H4  UNL     1       6.601  -1.495   0.359  1.00  0.00           H  
HETATM   29  H5  UNL     1       6.356  -1.121  -1.383  1.00  0.00           H  
HETATM   30  H6  UNL     1       8.476   0.335   0.322  1.00  0.00           H  
HETATM   31  H7  UNL     1       8.089   0.548  -1.396  1.00  0.00           H  
HETATM   32  H8  UNL     1       6.243   0.959   1.025  1.00  0.00           H  
HETATM   33  H9  UNL     1       7.042   2.292   0.194  1.00  0.00           H  
HETATM   34  H10 UNL     1       5.970   1.703  -1.951  1.00  0.00           H  
HETATM   35  H11 UNL     1       5.038   0.388  -1.181  1.00  0.00           H  
HETATM   36  H12 UNL     1       4.965   3.368  -0.496  1.00  0.00           H  
HETATM   37  H13 UNL     1       3.692   2.470  -1.374  1.00  0.00           H  
HETATM   38  H14 UNL     1       4.546   2.024   1.538  1.00  0.00           H  
HETATM   39  H15 UNL     1       3.058   2.816   0.915  1.00  0.00           H  
HETATM   40  H16 UNL     1       3.956  -0.100   0.574  1.00  0.00           H  
HETATM   41  H17 UNL     1       2.525   0.553  -0.201  1.00  0.00           H  
HETATM   42  H18 UNL     1       3.247   0.470   2.852  1.00  0.00           H  
HETATM   43  H19 UNL     1       0.944   0.151   3.261  1.00  0.00           H  
HETATM   44  H20 UNL     1      -0.460   1.106   1.427  1.00  0.00           H  
HETATM   45  H21 UNL     1       0.636   0.639   0.142  1.00  0.00           H  
HETATM   46  H22 UNL     1      -0.807  -1.261   2.094  1.00  0.00           H  
HETATM   47  H23 UNL     1       0.431  -1.796   0.929  1.00  0.00           H  
HETATM   48  H24 UNL     1      -0.974  -1.151  -0.971  1.00  0.00           H  
HETATM   49  H25 UNL     1      -1.833  -2.216   0.153  1.00  0.00           H  
HETATM   50  H26 UNL     1      -2.192   0.840   0.125  1.00  0.00           H  
HETATM   51  H27 UNL     1      -3.034  -0.333   1.151  1.00  0.00           H  
HETATM   52  H28 UNL     1      -4.190   0.390  -1.041  1.00  0.00           H  
HETATM   53  H29 UNL     1      -2.848  -0.309  -1.902  1.00  0.00           H  
HETATM   54  H30 UNL     1      -4.841  -1.748  -1.886  1.00  0.00           H  
HETATM   55  H31 UNL     1      -3.385  -2.544  -1.353  1.00  0.00           H  
HETATM   56  H32 UNL     1      -5.167  -3.318  -0.073  1.00  0.00           H  
HETATM   57  H33 UNL     1      -4.049  -2.525   1.012  1.00  0.00           H  
HETATM   58  H34 UNL     1      -6.901  -1.801   0.180  1.00  0.00           H  
HETATM   59  H35 UNL     1      -6.258  -2.427   1.703  1.00  0.00           H  
HETATM   60  H36 UNL     1      -5.205  -0.427   2.378  1.00  0.00           H  
HETATM   61  H37 UNL     1      -6.967  -0.359   2.291  1.00  0.00           H  
HETATM   62  H38 UNL     1      -6.094   1.663   2.039  1.00  0.00           H  
HETATM   63  H39 UNL     1      -4.937   1.366   0.779  1.00  0.00           H  
HETATM   64  H40 UNL     1      -7.961   1.748   0.707  1.00  0.00           H  
HETATM   65  H41 UNL     1      -6.648   2.659  -0.023  1.00  0.00           H  
HETATM   66  H42 UNL     1      -9.017   1.048  -2.230  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7   36   37
CONECT    7    8   38   39
CONECT    8    9   40   41
CONECT    9   10   10   42
CONECT   10   11   43
CONECT   11   12   44   45
CONECT   12   13   46   47
CONECT   13   14   48   49
CONECT   14   15   50   51
CONECT   15   16   52   53
CONECT   16   17   54   55
CONECT   17   18   56   57
CONECT   18   19   58   59
CONECT   19   20   60   61
CONECT   20   21   62   63
CONECT   21   22   64   65
CONECT   22   23   23   24
CONECT   24   66
END

HMDB0002068
     RDKit          3D
Erucic acid
 66 65  0  0  0  0  0  0  0  0999 V2000
    8.1745   -2.0910   -0.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0949   -1.1050   -0.5372 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6422    0.2775   -0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6105    1.2971    0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5208    1.3654   -0.9951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4655    2.3870   -0.6140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8209    2.0597    0.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1389    0.6958    0.6716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5523    0.4816    1.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2859    0.3068    2.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2993    0.3106    1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3647   -1.0508    1.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4041   -1.1980    0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5168   -0.2091    0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5036   -0.4269   -0.9467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1453   -1.7482   -0.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8524   -2.2038    0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9923   -1.6234    0.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0525   -0.3600    1.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9598    0.9934    1.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9698    1.5677    0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2605    1.0135   -1.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7546    0.0348   -1.7180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2790    1.6408   -1.9315 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4962   -2.7022   -0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0747   -1.5312   -1.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8318   -2.7863   -1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6011   -1.4949    0.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3556   -1.1209   -1.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4759    0.3355    0.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0894    0.5479   -1.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2427    0.9589    1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0425    2.2915    0.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9699    1.7027   -1.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0379    0.3883   -1.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9650    3.3681   -0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917    2.4696   -1.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5456    2.0237    1.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0585    2.8161    0.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9564   -0.0997    0.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5251    0.5530   -0.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2466    0.4703    2.8515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435    0.1507    3.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4596    1.1062    1.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362    0.6394    0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8074   -1.2613    2.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4313   -1.7956    0.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9738   -1.1513   -0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8333   -2.2162    0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1918    0.8396    0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0341   -0.3328    1.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1904    0.3899   -1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482   -0.3085   -1.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8406   -1.7477   -1.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3852   -2.5440   -1.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1665   -3.3175   -0.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0490   -2.5255    1.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9007   -1.8013    0.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2576   -2.4272    1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2049   -0.4271    2.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9668   -0.3593    2.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0937    1.6633    2.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9371    1.3656    0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9608    1.7478    0.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6485    2.6588   -0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0175    1.0485   -2.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  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  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  0
 17 57  1  0
 18 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 20 62  1  0
 20 63  1  0
 21 64  1  0
 21 65  1  0
 24 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(13Z)-13-Docosenoic acid	ChEBI
(13Z)-Docosenoic acid	ChEBI
(Z)-13-Docosenoic acid	ChEBI
(Z)-Docos-13-enoic acid	ChEBI
13-cis-Docosenoic acid	ChEBI
22:1Omega9	ChEBI
C22:1N-9	ChEBI
cis-13-Docosenoic acid	ChEBI
cis-Delta(13)-Docosenoic acid	ChEBI
cis-Eruic acid	ChEBI
Docos-13C-enoic acid	ChEBI
Erucasaeure	ChEBI
(13Z)-13-Docosenoate	Generator
(13Z)-Docosenoate	Generator
(Z)-13-Docosenoate	Generator
(Z)-Docos-13-enoate	Generator
13-cis-Docosenoate	Generator
cis-13-Docosenoate	Generator
cis-delta(13)-Docosenoate	Generator
cis-Δ(13)-docosenoate	Generator
cis-Δ(13)-docosenoic acid	Generator
cis-Eruate	Generator
Docos-13C-enoate	Generator
Erucate	Generator
13-Docosenoic acid	HMDB
Erucic acid, (Z)-isomer	HMDB
13-Docosenoate	HMDB
13-Docosenoic acid (acd/name 4.0)	HMDB
cis-Erucic acid	HMDB
delta 13-cis-Docosenoate	HMDB
delta 13-cis-Docosenoic acid	HMDB
Delta.13-cis-docosenoate	HMDB
Delta.13-cis-docosenoic acid	HMDB
Prifrac 2990	HMDB
(Z)-Erucic acid	HMDB
13(Z)-Docosenoic acid	HMDB
FA(22:1(13Z))	HMDB
FA(22:1n9)	HMDB
cis-13-Erucic acid	HMDB
delta13-cis-Docosenoic acid	HMDB
Δ13-cis-docosenoic acid	HMDB
Erucic acid	HMDB

Chemical Formula

C₂₂H₄₂O₂

Average Molecular Weight

338.5677

Monoisotopic Molecular Weight

338.318480588

IUPAC Name

(13Z)-docos-13-enoic acid

Traditional Name

erucic acid

CAS Registry Number

112-86-7

SMILES

CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O

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)/b10-9-

InChI Key

DPUOLQHDNGRHBS-KTKRTIGZSA-N

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
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

docosenoic acid (CHEBI:28792 )
Unsaturated fatty acids (C08316 )
Monounsaturated fatty acids (C08316 )
Unsaturated fatty acids (LMFA01030089 )

Ontology

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	33.5 °C	Not Available
Boiling Point	386.15 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	9.5e-05 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	9.459 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	188.502	30932474
[M-H]-	Not Available	188.502	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000261

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.3e-05 g/L	ALOGPS
logP	8.97	ALOGPS
logP	8.56	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	4.95	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	19	ChemAxon
Refractivity	105.81 m³·mol⁻¹	ChemAxon
Polarizability	45.6 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	192.272	31661259
DarkChem	[M-H]-	192.676	31661259
DeepCCS	[M+H]+	190.378	30932474
DeepCCS	[M-H]-	187.698	30932474
DeepCCS	[M-2H]-	222.828	30932474
DeepCCS	[M+Na]+	199.119	30932474
AllCCS	[M+H]+	198.5	32859911
AllCCS	[M+H-H2O]+	195.9	32859911
AllCCS	[M+NH4]+	200.8	32859911
AllCCS	[M+Na]+	201.5	32859911
AllCCS	[M-H]-	193.9	32859911
AllCCS	[M+Na-2H]-	196.1	32859911
AllCCS	[M+HCOO]-	198.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	11.12 minutes	32390414
Predicted by Siyang on May 30, 2022	29.2752 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.76 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	44.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3653.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	814.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	314.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	457.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	717.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1271.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1048.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	104.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2743.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	764.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2265.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1026.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	608.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	834.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	734.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Erucic acid	CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O	3561.6	Standard polar	33892256
Erucic acid	CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O	2479.2	Standard non polar	33892256
Erucic acid	CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O	2546.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Erucic acid,1TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCCCC(=O)O[Si](C)(C)C	2618.4	Semi standard non polar	33892256
Erucic acid,1TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2901.6	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces

Tissue Locations

Adrenal Gland
Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.264 +/- 1.590 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	0.028 +/- 0.002 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	20.2 +/- 6.8 uM	Adult (>18 years old)	Not Specified	Normal	27329611	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	150.0 (125.0-160.0) uM	Adult (>18 years old)	Both	Adrenomyeloneuropathy	8350883	details
Blood	Detected and Quantified	3.4 +/- 2.2 uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	27329611	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Adrenomyeloneuropathy
Aubourg P, Adamsbaum C, Lavallard-Rousseau MC, Rocchiccioli F, Cartier N, Jambaque I, Jakobezak C, Lemaitre A, Boureau F, Wolf C, et al.: A two-year trial of oleic and erucic acids ("Lorenzo's oil") as treatment for adrenomyeloneuropathy. N Engl J Med. 1993 Sep 9;329(11):745-52. [PubMed:8350883 ]
Isovaleric acidemia
Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

300100 (Adrenomyeloneuropathy)
243500 (Isovaleric acidemia)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Erucic_acid

METLIN ID

6470

PubChem Compound

5281116

PDB ID

Not Available

ChEBI ID

28792

Food Biomarker Ontology

Not Available

VMH ID

DOCO13AC

MarkerDB ID

MDB00000374

Good Scents ID

rw1242821

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

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. [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. [PubMed:16581239 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Erucic acid (HMDB0002068)

MOL for HMDB0002068 (Erucic acid)

3D MOL for HMDB0002068 (Erucic acid)

3D SDF for HMDB0002068 (Erucic acid)

3D-SDF for HMDB0002068 (Erucic acid)

PDB for HMDB0002068 (Erucic acid)

3D PDB for HMDB0002068 (Erucic acid)

SMILES for HMDB0002068 (Erucic acid)

INCHI for HMDB0002068 (Erucic acid)

Structure for HMDB0002068 (Erucic acid)

3D Structure for HMDB0002068 (Erucic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized