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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-10-23 11:28:21 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005060

Secondary Accession Numbers

HMDB05060

Metabolite Identification

Common Name

Eicosadienoic acid

Description

Eicosadienoic acid is an omega-6 fatty acid found in human milk (PMID: 15256803 ). Omega-6 fatty acids are a family of unsaturated fatty acids which have in common a carbon-carbon double bond in the n−6 position; that is, the sixth bond from the end of the fatty acid. The biological effects of the omega−6 fatty acids are largely mediated by their conversion to n-6 eicosanoids that bind to diverse receptors found in every tissue of the body. Eicosadienoic acid has been identified in the human placenta (PMID: 32033212 ).

Structure

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

HMDB0005060
     RDKit          3D
Eicosadienoic acid
 58 57  0  0  0  0  0  0  0  0999 V2000
   -6.6445   -1.5145   -1.6479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6099   -0.3592   -1.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2945    0.8714   -1.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4267    2.0517   -0.9337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2432    1.9664   -0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7361    1.6256    1.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3667    0.6846    2.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3515   -0.3387    2.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4703   -0.4674    0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1557   -0.3181    0.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4329    0.0010    2.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5624   -1.0625    2.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084   -1.3258    1.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4172   -0.1074    1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4638   -0.5307    0.1654 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2677    0.7171   -0.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3182    0.4407   -1.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2386   -0.6294   -0.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3200   -0.9252   -1.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1897    0.2028   -1.9645 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1528    1.3551   -1.5107 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1968   -0.0535   -2.9150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8363   -1.8905   -0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5357   -1.1062   -2.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2179   -2.3066   -2.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1582   -0.1650   -2.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8642   -0.6828   -0.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1598    1.1008   -1.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8132    0.6346   -0.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0509    2.9617   -0.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012    2.2760   -1.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4391    1.3584   -0.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7985    3.0225    0.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5677    2.2829    1.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9536    0.6637    3.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8909   -1.3869    2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7678   -0.3490    2.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8295   -0.7552   -0.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5660   -0.4386    0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0335    0.3268    3.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2121    0.9284    1.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0571   -2.0348    2.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0728   -0.6937    3.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2811   -2.1578    1.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1275   -1.7256    0.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8902    0.3123    2.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7619    0.6783    0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9669   -0.9281   -0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0737   -1.3428    0.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5755    1.5046   -0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7107    1.0117    0.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8393    1.3763   -1.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7720    0.1244   -2.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6210   -1.5780   -0.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5946   -0.4791    0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9488   -1.7394   -1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8099   -1.2429   -2.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1655    0.1557   -2.7404 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  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  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 22 58  1  0
M  END

  Mrv1652304272018552D          

 22 21  0  0  0  0            999 V2000
   -2.8875   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -8.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -8.5737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -9.2881    0.0000 O   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
  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  2  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
 15 16  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  2  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005060

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/CCCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10H,2-5,8,11-19H2,1H3,(H,21,22)/b7-6-,10-9-

> <INCHI_KEY>
XSXIVVZCUAHUJO-HZJYTTRNSA-N

> <FORMULA>
C20H36O2

> <MOLECULAR_WEIGHT>
308.4986

> <EXACT_MASS>
308.271530396

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
39.93907978229116

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(11Z,14Z)-icosa-11,14-dienoic acid

> <ALOGPS_LOGP>
7.83

> <JCHEM_LOGP>
7.311014124333333

> <ALOGPS_LOGS>
-6.75

> <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>
97.72079999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.42e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
eicosadienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005060
     RDKit          3D
Eicosadienoic acid
 58 57  0  0  0  0  0  0  0  0999 V2000
   -6.6445   -1.5145   -1.6479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6099   -0.3592   -1.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2945    0.8714   -1.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4267    2.0517   -0.9337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2432    1.9664   -0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7361    1.6256    1.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3667    0.6846    2.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3515   -0.3387    2.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4703   -0.4674    0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1557   -0.3181    0.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4329    0.0010    2.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5624   -1.0625    2.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084   -1.3258    1.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4172   -0.1074    1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4638   -0.5307    0.1654 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2677    0.7171   -0.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3182    0.4407   -1.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2386   -0.6294   -0.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3200   -0.9252   -1.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1897    0.2028   -1.9645 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1528    1.3551   -1.5107 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1968   -0.0535   -2.9150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8363   -1.8905   -0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5357   -1.1062   -2.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2179   -2.3066   -2.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1582   -0.1650   -2.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8642   -0.6828   -0.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1598    1.1008   -1.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8132    0.6346   -0.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0509    2.9617   -0.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012    2.2760   -1.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4391    1.3584   -0.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7985    3.0225    0.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5677    2.2829    1.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9536    0.6637    3.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8909   -1.3869    2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7678   -0.3490    2.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8295   -0.7552   -0.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5660   -0.4386    0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0335    0.3268    3.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2121    0.9284    1.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0571   -2.0348    2.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0728   -0.6937    3.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2811   -2.1578    1.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1275   -1.7256    0.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8902    0.3123    2.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7619    0.6783    0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9669   -0.9281   -0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0737   -1.3428    0.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5755    1.5046   -0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7107    1.0117    0.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8393    1.3763   -1.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7720    0.1244   -2.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6210   -1.5780   -0.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5946   -0.4791    0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9488   -1.7394   -1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8099   -1.2429   -2.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1655    0.1557   -2.7404 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  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  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 22 58  1  0
M  END

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0      -5.390  -4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.850  -4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.620  -5.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.850  -6.668   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.620  -8.002   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.850  -9.336   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.620 -10.669   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.850 -12.003   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.620 -13.337   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.850 -14.670   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.620 -16.004   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.160 -16.004   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.850 -17.338   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
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   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0005060
HETATM    1  C1  UNL     1      -6.645  -1.515  -1.648  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.610  -0.359  -1.545  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.295   0.871  -1.031  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.427   2.052  -0.934  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.243   1.966  -0.007  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.736   1.626   1.327  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.367   0.685   2.131  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.352  -0.339   2.018  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.470  -0.467   0.881  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.156  -0.318   0.929  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.433   0.001   2.151  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.562  -1.063   2.531  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.608  -1.326   1.502  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.417  -0.107   1.219  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.464  -0.531   0.165  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.268   0.717  -0.102  1.00  0.00           C  
HETATM   17  C17 UNL     1       5.318   0.441  -1.127  1.00  0.00           C  
HETATM   18  C18 UNL     1       6.239  -0.629  -0.637  1.00  0.00           C  
HETATM   19  C19 UNL     1       7.320  -0.925  -1.638  1.00  0.00           C  
HETATM   20  C20 UNL     1       8.190   0.203  -1.965  1.00  0.00           C  
HETATM   21  O1  UNL     1       8.153   1.355  -1.511  1.00  0.00           O  
HETATM   22  O2  UNL     1       9.197  -0.053  -2.915  1.00  0.00           O  
HETATM   23  H1  UNL     1      -6.836  -1.891  -0.640  1.00  0.00           H  
HETATM   24  H2  UNL     1      -7.536  -1.106  -2.163  1.00  0.00           H  
HETATM   25  H3  UNL     1      -6.218  -2.307  -2.277  1.00  0.00           H  
HETATM   26  H4  UNL     1      -5.158  -0.165  -2.533  1.00  0.00           H  
HETATM   27  H5  UNL     1      -4.864  -0.683  -0.808  1.00  0.00           H  
HETATM   28  H6  UNL     1      -7.160   1.101  -1.730  1.00  0.00           H  
HETATM   29  H7  UNL     1      -6.813   0.635  -0.050  1.00  0.00           H  
HETATM   30  H8  UNL     1      -6.051   2.962  -0.632  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.001   2.276  -1.962  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.439   1.358  -0.382  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.799   3.023   0.120  1.00  0.00           H  
HETATM   34  H12 UNL     1      -5.568   2.283   1.721  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.954   0.664   3.108  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.891  -1.387   2.157  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.768  -0.349   2.997  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.830  -0.755  -0.120  1.00  0.00           H  
HETATM   39  H17 UNL     1      -0.566  -0.439   0.000  1.00  0.00           H  
HETATM   40  H18 UNL     1      -1.033   0.327   3.015  1.00  0.00           H  
HETATM   41  H19 UNL     1       0.212   0.928   1.946  1.00  0.00           H  
HETATM   42  H20 UNL     1       0.057  -2.035   2.758  1.00  0.00           H  
HETATM   43  H21 UNL     1       1.073  -0.694   3.468  1.00  0.00           H  
HETATM   44  H22 UNL     1       2.281  -2.158   1.842  1.00  0.00           H  
HETATM   45  H23 UNL     1       1.128  -1.726   0.571  1.00  0.00           H  
HETATM   46  H24 UNL     1       2.890   0.312   2.108  1.00  0.00           H  
HETATM   47  H25 UNL     1       1.762   0.678   0.758  1.00  0.00           H  
HETATM   48  H26 UNL     1       2.967  -0.928  -0.721  1.00  0.00           H  
HETATM   49  H27 UNL     1       4.074  -1.343   0.647  1.00  0.00           H  
HETATM   50  H28 UNL     1       3.575   1.505  -0.456  1.00  0.00           H  
HETATM   51  H29 UNL     1       4.711   1.012   0.892  1.00  0.00           H  
HETATM   52  H30 UNL     1       5.839   1.376  -1.442  1.00  0.00           H  
HETATM   53  H31 UNL     1       4.772   0.124  -2.066  1.00  0.00           H  
HETATM   54  H32 UNL     1       5.621  -1.578  -0.598  1.00  0.00           H  
HETATM   55  H33 UNL     1       6.595  -0.479   0.385  1.00  0.00           H  
HETATM   56  H34 UNL     1       7.949  -1.739  -1.229  1.00  0.00           H  
HETATM   57  H35 UNL     1       6.810  -1.243  -2.579  1.00  0.00           H  
HETATM   58  H36 UNL     1      10.166   0.156  -2.740  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7    7   34
CONECT    7    8   35
CONECT    8    9   36   37
CONECT    9   10   10   38
CONECT   10   11   39
CONECT   11   12   40   41
CONECT   12   13   42   43
CONECT   13   14   44   45
CONECT   14   15   46   47
CONECT   15   16   48   49
CONECT   16   17   50   51
CONECT   17   18   52   53
CONECT   18   19   54   55
CONECT   19   20   56   57
CONECT   20   21   21   22
CONECT   22   58
END

HMDB0005060
     RDKit          3D
Eicosadienoic acid
 58 57  0  0  0  0  0  0  0  0999 V2000
   -6.6445   -1.5145   -1.6479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6099   -0.3592   -1.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2945    0.8714   -1.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4267    2.0517   -0.9337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2432    1.9664   -0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7361    1.6256    1.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3667    0.6846    2.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3515   -0.3387    2.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4703   -0.4674    0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1557   -0.3181    0.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4329    0.0010    2.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5624   -1.0625    2.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084   -1.3258    1.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4172   -0.1074    1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4638   -0.5307    0.1654 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2677    0.7171   -0.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3182    0.4407   -1.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2386   -0.6294   -0.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3200   -0.9252   -1.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1897    0.2028   -1.9645 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1528    1.3551   -1.5107 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1968   -0.0535   -2.9150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8363   -1.8905   -0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5357   -1.1062   -2.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2179   -2.3066   -2.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1582   -0.1650   -2.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8642   -0.6828   -0.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1598    1.1008   -1.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8132    0.6346   -0.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0509    2.9617   -0.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012    2.2760   -1.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4391    1.3584   -0.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7985    3.0225    0.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5677    2.2829    1.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9536    0.6637    3.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8909   -1.3869    2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7678   -0.3490    2.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8295   -0.7552   -0.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5660   -0.4386    0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0335    0.3268    3.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2121    0.9284    1.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0571   -2.0348    2.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0728   -0.6937    3.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2811   -2.1578    1.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1275   -1.7256    0.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8902    0.3123    2.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7619    0.6783    0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9669   -0.9281   -0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0737   -1.3428    0.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5755    1.5046   -0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7107    1.0117    0.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8393    1.3763   -1.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7720    0.1244   -2.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6210   -1.5780   -0.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5946   -0.4791    0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9488   -1.7394   -1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8099   -1.2429   -2.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1655    0.1557   -2.7404 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  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  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 22 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(11Z,14Z)-Eicosa-11,14-dienoic acid	ChEBI
(11Z,14Z)-Eicosadienoic acid	ChEBI
(11Z,14Z)-Icosa-11,14-dienoic acid	ChEBI
11,14-Eicosadienoic acid	ChEBI
11,14-Icosadienoic acid	ChEBI
(11Z,14Z)-Eicosa-11,14-dienoate	Generator
(11Z,14Z)-Eicosadienoate	Generator
(11Z,14Z)-Icosa-11,14-dienoate	Generator
11,14-Eicosadienoate	Generator
11,14-Icosadienoate	Generator
Eicosadienoate	Generator
11, 14-Icosadienoate	HMDB
11, 14-Icosadienoic acid	HMDB
11,14-trans-Eicosadienoic acid	HMDB
delta11,14-20:2	HMDB
Eicosa-11,14-dienoic acid	HMDB
Eicosa-11,14-dienoic acid, (Z,Z)-isomer	HMDB
N-6 Eicosadienoic acid	HMDB
Dihomolinoleate	HMDB
(11Z,14Z)-Icosadienoate	HMDB
(11Z,14Z)-11,14-Eicosadienate	HMDB
(11Z,14Z)-11,14-Eicosadienic acid	HMDB
(11Z,14Z)-11,14-Eicosadienoate	HMDB
(11Z,14Z)-11,14-Eicosadienoic acid	HMDB
11,14-all-cis-Eicosadienoate	HMDB
11,14-all-cis-Eicosadienoic acid	HMDB
11-cis,14-cis-Eicosadienoate	HMDB
11-cis,14-cis-Eicosadienoic acid	HMDB
Bishomolinoleate	HMDB
Bishomolinoleic acid	HMDB
Dihomo-linoleate (20:2n6)	HMDB
Dihomo-linoleic acid (20:2n6)	HMDB
FA(20:2(11Z,14Z))	HMDB
Homo-gamma-linoleate	HMDB
Homo-gamma-linoleic acid	HMDB
Homo-γ-linoleate	HMDB
Homo-γ-linoleic acid	HMDB
all-cis-11,14-Eicosadienoate	HMDB
all-cis-11,14-Eicosadienoic acid	HMDB
cis,cis-Eicosa-11,14-dienoate	HMDB
cis,cis-Eicosa-11,14-dienoic acid	HMDB
cis,cis-delta11,14-Eicosadienoate	HMDB
cis,cis-delta11,14-Eicosadienoic acid	HMDB
cis,cis-Δ11,14-eicosadienoate	HMDB
cis,cis-Δ11,14-eicosadienoic acid	HMDB
cis-11,cis-14-Eicosadienoate	HMDB
cis-11,cis-14-Eicosadienoic acid	HMDB
delta11,14-Eicosadienoate	HMDB
delta11,14-Eicosadienoic acid	HMDB
Δ11,14-eicosadienoate	HMDB
Δ11,14-eicosadienoic acid	HMDB
FA(20:2n6)	HMDB
Eicosadienoic acid	ChEBI

Chemical Formula

C₂₀H₃₆O₂

Average Molecular Weight

308.4986

Monoisotopic Molecular Weight

308.271530396

IUPAC Name

(11Z,14Z)-icosa-11,14-dienoic acid

Traditional Name

eicosadienoic acid

CAS Registry Number

5598-38-9

SMILES

CCCCC\C=C/C\C=C/CCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C20H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10H,2-5,8,11-19H2,1H3,(H,21,22)/b7-6-,10-9-

InChI Key

XSXIVVZCUAHUJO-HZJYTTRNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

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

icosadienoic acid (CHEBI:73731 )
Unsaturated fatty acids (C16525 )
Polyunsaturated fatty acids (C16525 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)

Organ

Placenta (HMDB: HMDB0005060)

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)

Cellular substructure

Extracellular (HMDB: HMDB0005060)
Membrane (HMDB: HMDB0005060)

Source

Exogenous

Exogenous (HMDB: HMDB0005060)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Nut

Black walnut (FooDB: FOOD00093)

Endogenous

Endogenous (HMDB: HMDB0005060)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	462.10 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.0015 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.251	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	182.375	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001850

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.4e-05 g/L	ALOGPS
logP	7.83	ALOGPS
logP	7.31	ChemAxon
logS	-6.8	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	16	ChemAxon
Refractivity	97.72 m³·mol⁻¹	ChemAxon
Polarizability	39.94 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]+	186.788	31661259
DarkChem	[M-H]-	186.756	31661259
DeepCCS	[M+H]+	184.135	30932474
DeepCCS	[M-H]-	181.777	30932474
DeepCCS	[M-2H]-	215.744	30932474
DeepCCS	[M+Na]+	191.696	30932474
AllCCS	[M+H]+	186.6	32859911
AllCCS	[M+H-H2O]+	183.7	32859911
AllCCS	[M+NH4]+	189.2	32859911
AllCCS	[M+Na]+	189.9	32859911
AllCCS	[M-H]-	186.3	32859911
AllCCS	[M+Na-2H]-	188.3	32859911
AllCCS	[M+HCOO]-	190.5	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.	10.08 minutes	32390414
Predicted by Siyang on May 30, 2022	26.8573 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	39.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3333.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	716.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	282.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	452.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	691.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1203.6 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	847.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	95.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2504.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	751.4 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	2078.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	938.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	561.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	692.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	675.7 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	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Eicosadienoic acid	CCCCC\C=C/C\C=C/CCCCCCCCCC(O)=O	3473.3	Standard polar	33892256
Eicosadienoic acid	CCCCC\C=C/C\C=C/CCCCCCCCCC(O)=O	2258.4	Standard non polar	33892256
Eicosadienoic acid	CCCCC\C=C/C\C=C/CCCCCCCCCC(O)=O	2336.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Eicosadienoic acid,1TMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)O[Si](C)(C)C	2414.3	Semi standard non polar	33892256
Eicosadienoic acid,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2664.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Eicosadienoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9760000000-cd3039251f27ed659833	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eicosadienoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9652000000-051c308924d68202698f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eicosadienoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eicosadienoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosadienoic acid LC-ESI-IT , negative-QTOF	splash10-000i-0091000000-cd5567f72a97a19a5daa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosadienoic acid n/a 21V, positive-QTOF	splash10-0006-0290000000-26edae55398bbe6d8f14	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 30V, positive-QTOF	splash10-003v-9200000000-f117dd4d613f97c9e9a1	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 33V, positive-QTOF	splash10-003u-9100000000-64feb0d0359edf0e55fa	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 37V, positive-QTOF	splash10-003u-9100000000-1c5be01a286361015756	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 40V, positive-QTOF	splash10-005c-9100000000-2af5db21026406ee4f51	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 44V, positive-QTOF	splash10-005c-9100000000-900bb2bb1942a2772e06	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosadienoic acid n/a 21V, positive-QTOF	splash10-05o0-1900000000-87b112cb6d02616a7390	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 0V, positive-QTOF	splash10-0a4i-0009000000-66380db5e2f48c28d914	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 1V, positive-QTOF	splash10-0a4i-0009000000-37933ac7549ff468e6e0	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 3V, positive-QTOF	splash10-0a4i-0019000000-139b1c14ace122806206	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 4V, positive-QTOF	splash10-0a4i-0049000000-bea23a8f63f68b2a2579	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 7V, positive-QTOF	splash10-052g-3594000000-9f6dd586ee4aa178e78e	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosadienoic acid n/a 21V, positive-QTOF	splash10-0hka-0930000000-500174f550638fdb0b03	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosadienoic acid n/a 21V, positive-QTOF	splash10-00di-0490000000-80d1e0e8b9b35e163450	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 4V, positive-QTOF	splash10-0006-0090000000-cf7b1131f470250aedcb	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 6V, positive-QTOF	splash10-0006-0090000000-32033519d24a370bbb6e	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 10V, positive-QTOF	splash10-0006-2590000000-f57018cf6f280ddd27bd	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 14V, positive-QTOF	splash10-059w-7930000000-7f2165e3d0add956aa59	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosadienoic acid 10V, Positive-QTOF	splash10-0006-0092000000-bcb4dbfbca4a66a8f89a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosadienoic acid 20V, Positive-QTOF	splash10-03kd-4591000000-8359fe54412fa3b34e4c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosadienoic acid 40V, Positive-QTOF	splash10-00kg-9850000000-1ce6afea317e415a6b1d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosadienoic acid 10V, Negative-QTOF	splash10-0a4i-0039000000-46defe7a3a5473b710fd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosadienoic acid 20V, Negative-QTOF	splash10-0bti-1096000000-42d4303cc1fdabc4e3c0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosadienoic acid 40V, Negative-QTOF	splash10-0a4l-9140000000-5622f571522f8f140346	2017-09-01	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.418 +/- 0.162 uM	Adult (>18 years old)	Both	Normal	18953024	details
Blood	Detected and Quantified	0.352 +/- 0.029 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	15.0730 +/- 4.182 uM	Adult (>18 years old)	Female	Normal	9368807	details
Blood	Detected and Quantified	20.3 +/- 6.8 uM	Adult (>18 years old)	Not Specified	Normal	27329611	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	16.9 +/- 4.8 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

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

243500 (Isovaleric acidemia)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012619

KNApSAcK ID

Not Available

Chemspider ID

4944228

KEGG Compound ID

C16525

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6439848

PDB ID

Not Available

ChEBI ID

73731

Food Biomarker Ontology

Not Available

VMH ID

EIDI1114AC

MarkerDB ID

Not Available

Good Scents ID

rw1210811

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Minda H, Kovacs A, Funke S, Szasz M, Burus I, Molnar S, Marosvolgyi T, Decsi T: Changes of fatty acid composition of human milk during the first month of lactation: a day-to-day approach in the first week. Ann Nutr Metab. 2004;48(3):202-9. Epub 2004 Jul 13. [PubMed:15256803 ]
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 ]
Lipid Maps (LMFA01030130) [Link]

Showing metabocard for Eicosadienoic acid (HMDB0005060)

MOL for HMDB0005060 (Eicosadienoic acid)

3D MOL for HMDB0005060 (Eicosadienoic acid)

3D SDF for HMDB0005060 (Eicosadienoic acid)

3D-SDF for HMDB0005060 (Eicosadienoic acid)

PDB for HMDB0005060 (Eicosadienoic acid)

3D PDB for HMDB0005060 (Eicosadienoic acid)

SMILES for HMDB0005060 (Eicosadienoic acid)

INCHI for HMDB0005060 (Eicosadienoic acid)

Structure for HMDB0005060 (Eicosadienoic acid)

3D Structure for HMDB0005060 (Eicosadienoic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra