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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2008-09-16 13:19:52 UTC

Update Date

2022-03-07 02:50:54 UTC

HMDB ID

HMDB0010378

Secondary Accession Numbers

HMDB10378

Metabolite Identification

Common Name

5,8,11-Eicosatrienoic acid

Description

5,8,11-Eicosatrienoic acid (Mead acid) is a carboxylic acid with a 20-carbon chain and three methylene-interrupted cis double bonds. The first double bond is located at the ninth carbon from the omega end. In physiological literature, it is given the name 20:3(n-9). In the presence of lipoxygenase, Mead acid can form various hydroxy products (HETE). It is the only polyunsaturated fatty acid that the body can make de novo. Its elevated presence in the blood is an indication of essential fatty acid (EFA)deficiency. During dietary EFA insufficiency, especially arachidonic acid deficiency, the body will make Mead acid by the elongation and desaturation of oleic acid. (Wikipedia).

Structure

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

HMDB0010378
     RDKit          3D
5,8,11-Eicosatrienoic acid
 56 55  0  0  0  0  0  0  0  0999 V2000
   -7.0898   -1.3468   -2.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7818   -1.7829   -1.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5698   -0.8591   -0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3027   -1.1786    0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0614   -1.0750   -0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8198    0.2811   -1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6828    1.3690   -0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4904    1.0512    0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4040    2.1223    1.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4237    2.9424    2.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8461    3.0201    1.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1689    2.1839    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1475    1.3083    0.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0219    1.1067    1.4160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4341    1.4108    1.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4585    0.5980    1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3726   -0.8037    1.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8785   -1.7206    0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0340   -1.5228   -0.7269 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5310   -2.4087   -1.8046 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5051   -3.1616   -1.6202 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9265   -2.4301   -3.0604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5288   -2.1889   -2.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7513   -0.9970   -1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8668   -0.4922   -2.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9738   -1.7477   -2.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8847   -2.8486   -1.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5831    0.1754   -0.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4133   -1.0191    0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3978   -2.2634    0.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2433   -0.6248    1.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1870   -1.7698   -1.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2167   -1.4297    0.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5385    0.5318   -1.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8159    0.2330   -1.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3841    2.2931   -0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6001    1.5450    0.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7811    0.0611    1.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6667    0.7697    0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3150    2.2617    2.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5869    3.7152    2.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7072    3.1826    2.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8274    4.1116    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5923    2.2937   -0.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3263    0.7124   -0.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6689    1.6081    2.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9570    0.0065    1.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6635    2.4371    0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4838    0.9452    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0857   -0.9620    2.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3721   -1.1316    1.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8197   -2.7622    0.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8976   -1.3847    0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9603   -1.7391   -0.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1826   -0.4650   -1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4923   -2.1613   -3.8500 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  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  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
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 22 56  1  0
M  END


  Mrv0541 02241200532D          

 22 21  0  0  0  0            999 V2000
    5.9205   -8.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6349   -8.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3494   -8.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0639   -8.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7783   -8.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4928   -8.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2073   -8.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9218   -8.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6363   -8.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3507   -8.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0652   -8.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7797   -8.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4941   -8.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2086   -8.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9231   -8.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6376   -8.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3521   -8.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0665   -8.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7810   -8.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4955   -8.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2100   -8.2263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4955   -9.4638    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  1  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  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  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
 20 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0010378

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h9-10,12-13,15-16H,2-8,11,14,17-19H2,1H3,(H,21,22)/b10-9-,13-12-,16-15-

> <INCHI_KEY>
UNSRRHDPHVZAHH-YOILPLPUSA-N

> <FORMULA>
C20H34O2

> <MOLECULAR_WEIGHT>
306.4828

> <EXACT_MASS>
306.255880332

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
39.07977505475794

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z,8Z,11Z)-icosa-5,8,11-trienoic acid

> <ALOGPS_LOGP>
7.35

> <JCHEM_LOGP>
6.9490924676666666

> <ALOGPS_LOGS>
-6.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771840522258

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
98.8374

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.27e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mead acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0010378
     RDKit          3D
5,8,11-Eicosatrienoic acid
 56 55  0  0  0  0  0  0  0  0999 V2000
   -7.0898   -1.3468   -2.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7818   -1.7829   -1.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5698   -0.8591   -0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3027   -1.1786    0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0614   -1.0750   -0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8198    0.2811   -1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6828    1.3690   -0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4904    1.0512    0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4040    2.1223    1.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4237    2.9424    2.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8461    3.0201    1.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1689    2.1839    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1475    1.3083    0.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0219    1.1067    1.4160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4341    1.4108    1.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4585    0.5980    1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3726   -0.8037    1.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8785   -1.7206    0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0340   -1.5228   -0.7269 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5310   -2.4087   -1.8046 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5051   -3.1616   -1.6202 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9265   -2.4301   -3.0604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5288   -2.1889   -2.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7513   -0.9970   -1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8668   -0.4922   -2.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9738   -1.7477   -2.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8847   -2.8486   -1.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5831    0.1754   -0.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4133   -1.0191    0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3978   -2.2634    0.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2433   -0.6248    1.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1870   -1.7698   -1.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2167   -1.4297    0.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5385    0.5318   -1.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8159    0.2330   -1.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3841    2.2931   -0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6001    1.5450    0.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7811    0.0611    1.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6667    0.7697    0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3150    2.2617    2.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5869    3.7152    2.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7072    3.1826    2.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8274    4.1116    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5923    2.2937   -0.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3263    0.7124   -0.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6689    1.6081    2.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9570    0.0065    1.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6635    2.4371    0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4838    0.9452    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0857   -0.9620    2.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3721   -1.1316    1.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8197   -2.7622    0.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8976   -1.3847    0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9603   -1.7391   -0.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1826   -0.4650   -1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4923   -2.1613   -3.8500 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  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  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
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 22 56  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      11.052 -16.126   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.385 -15.356   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.719 -16.126   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.053 -15.356   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.386 -16.126   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.720 -15.356   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.054 -16.126   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.387 -15.356   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.721 -16.126   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.055 -16.126   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.388 -15.356   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.722 -16.126   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.056 -16.126   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.389 -15.356   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.723 -16.126   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.057 -16.126   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      32.391 -15.356   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      33.724 -16.126   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      35.058 -15.356   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      36.392 -16.126   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      37.725 -15.356   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      36.392 -17.666   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    HMDB0010378
HETATM    1  C1  UNL     1      -7.090  -1.347  -2.257  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.782  -1.783  -1.593  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.570  -0.859  -0.423  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.303  -1.179   0.333  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.061  -1.075  -0.487  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.820   0.281  -1.062  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.683   1.369  -0.025  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.490   1.051   0.906  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.404   2.122   1.876  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.424   2.942   2.062  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.846   3.020   1.353  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.169   2.184   0.242  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.148   1.308   0.235  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.022   1.107   1.416  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.434   1.411   1.109  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.458   0.598   1.196  1.00  0.00           C  
HETATM   17  C17 UNL     1       5.373  -0.804   1.628  1.00  0.00           C  
HETATM   18  C18 UNL     1       5.879  -1.721   0.496  1.00  0.00           C  
HETATM   19  C19 UNL     1       5.034  -1.523  -0.727  1.00  0.00           C  
HETATM   20  C20 UNL     1       5.531  -2.409  -1.805  1.00  0.00           C  
HETATM   21  O1  UNL     1       6.505  -3.162  -1.620  1.00  0.00           O  
HETATM   22  O2  UNL     1       4.926  -2.430  -3.060  1.00  0.00           O  
HETATM   23  H1  UNL     1      -7.529  -2.189  -2.832  1.00  0.00           H  
HETATM   24  H2  UNL     1      -7.751  -0.997  -1.463  1.00  0.00           H  
HETATM   25  H3  UNL     1      -6.867  -0.492  -2.928  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.974  -1.748  -2.341  1.00  0.00           H  
HETATM   27  H5  UNL     1      -5.885  -2.849  -1.273  1.00  0.00           H  
HETATM   28  H6  UNL     1      -5.583   0.175  -0.816  1.00  0.00           H  
HETATM   29  H7  UNL     1      -6.413  -1.019   0.278  1.00  0.00           H  
HETATM   30  H8  UNL     1      -4.398  -2.263   0.635  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.243  -0.625   1.288  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.187  -1.770  -1.366  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.217  -1.430   0.119  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.539   0.532  -1.847  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.816   0.233  -1.580  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.384   2.293  -0.563  1.00  0.00           H  
HETATM   37  H15 UNL     1      -3.600   1.545   0.554  1.00  0.00           H  
HETATM   38  H16 UNL     1      -1.781   0.061   1.434  1.00  0.00           H  
HETATM   39  H17 UNL     1      -0.667   0.770   0.287  1.00  0.00           H  
HETATM   40  H18 UNL     1      -2.315   2.262   2.564  1.00  0.00           H  
HETATM   41  H19 UNL     1      -0.587   3.715   2.907  1.00  0.00           H  
HETATM   42  H20 UNL     1       1.707   3.183   2.072  1.00  0.00           H  
HETATM   43  H21 UNL     1       0.827   4.112   0.892  1.00  0.00           H  
HETATM   44  H22 UNL     1       0.592   2.294  -0.697  1.00  0.00           H  
HETATM   45  H23 UNL     1       2.326   0.712  -0.657  1.00  0.00           H  
HETATM   46  H24 UNL     1       2.669   1.608   2.336  1.00  0.00           H  
HETATM   47  H25 UNL     1       2.957   0.007   1.697  1.00  0.00           H  
HETATM   48  H26 UNL     1       4.663   2.437   0.768  1.00  0.00           H  
HETATM   49  H27 UNL     1       6.484   0.945   0.935  1.00  0.00           H  
HETATM   50  H28 UNL     1       6.086  -0.962   2.485  1.00  0.00           H  
HETATM   51  H29 UNL     1       4.372  -1.132   1.854  1.00  0.00           H  
HETATM   52  H30 UNL     1       5.820  -2.762   0.872  1.00  0.00           H  
HETATM   53  H31 UNL     1       6.898  -1.385   0.275  1.00  0.00           H  
HETATM   54  H32 UNL     1       3.960  -1.739  -0.548  1.00  0.00           H  
HETATM   55  H33 UNL     1       5.183  -0.465  -1.067  1.00  0.00           H  
HETATM   56  H34 UNL     1       5.492  -2.161  -3.850  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   34   35
CONECT    7    8   36   37
CONECT    8    9   38   39
CONECT    9   10   10   40
CONECT   10   11   41
CONECT   11   12   42   43
CONECT   12   13   13   44
CONECT   13   14   45
CONECT   14   15   46   47
CONECT   15   16   16   48
CONECT   16   17   49
CONECT   17   18   50   51
CONECT   18   19   52   53
CONECT   19   20   54   55
CONECT   20   21   21   22
CONECT   22   56
END

HMDB0010378
     RDKit          3D
5,8,11-Eicosatrienoic acid
 56 55  0  0  0  0  0  0  0  0999 V2000
   -7.0898   -1.3468   -2.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7818   -1.7829   -1.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5698   -0.8591   -0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3027   -1.1786    0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0614   -1.0750   -0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8198    0.2811   -1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6828    1.3690   -0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4904    1.0512    0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4040    2.1223    1.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4237    2.9424    2.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8461    3.0201    1.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1689    2.1839    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1475    1.3083    0.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0219    1.1067    1.4160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4341    1.4108    1.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4585    0.5980    1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3726   -0.8037    1.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8785   -1.7206    0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0340   -1.5228   -0.7269 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5310   -2.4087   -1.8046 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5051   -3.1616   -1.6202 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9265   -2.4301   -3.0604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5288   -2.1889   -2.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7513   -0.9970   -1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8668   -0.4922   -2.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9738   -1.7477   -2.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8847   -2.8486   -1.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5831    0.1754   -0.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4133   -1.0191    0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3978   -2.2634    0.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2433   -0.6248    1.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1870   -1.7698   -1.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2167   -1.4297    0.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5385    0.5318   -1.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8159    0.2330   -1.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3841    2.2931   -0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6001    1.5450    0.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7811    0.0611    1.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6667    0.7697    0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3150    2.2617    2.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5869    3.7152    2.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7072    3.1826    2.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8274    4.1116    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5923    2.2937   -0.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3263    0.7124   -0.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6689    1.6081    2.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9570    0.0065    1.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6635    2.4371    0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4838    0.9452    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0857   -0.9620    2.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3721   -1.1316    1.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8197   -2.7622    0.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8976   -1.3847    0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9603   -1.7391   -0.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1826   -0.4650   -1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4923   -2.1613   -3.8500 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  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  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
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 22 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z,8Z,11Z)-Eicosa-5,8,11-trienoic acid	ChEBI
(5Z,8Z,11Z)-Eicosatrienoic acid	ChEBI
5Z,8Z,11Z-Eicosatrienoic acid	ChEBI
5Z,8Z,11Z-Icosatrienoic acid	ChEBI
all-cis-Eicosa-5,8,11-trienoic acid	ChEBI
all-cis-Icosa-5,8,11-trienoic acid	ChEBI
C20:3N-9,12,15	ChEBI
ETrE(5Z,8Z,11Z)	ChEBI
Mead acid	ChEBI
(5Z,8Z,11Z)-Eicosa-5,8,11-trienoate	Generator
(5Z,8Z,11Z)-Eicosatrienoate	Generator
5Z,8Z,11Z-Eicosatrienoate	Generator
5Z,8Z,11Z-Icosatrienoate	Generator
all-cis-Eicosa-5,8,11-trienoate	Generator
all-cis-Icosa-5,8,11-trienoate	Generator
5,8,11-Eicosatrienoate	Generator
5,8,11-Eicosatrienoic acid	MeSH, HMDB
ETrA acid	MeSH, HMDB
(5Z,8Z,11Z)-Icosatrienoate	Generator, HMDB

Chemical Formula

C₂₀H₃₄O₂

Average Molecular Weight

306.4828

Monoisotopic Molecular Weight

306.255880332

IUPAC Name

(5Z,8Z,11Z)-icosa-5,8,11-trienoic acid

Traditional Name

mead acid

CAS Registry Number

20590-32-3

SMILES

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

InChI Identifier

InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h9-10,12-13,15-16H,2-8,11,14,17-19H2,1H3,(H,21,22)/b10-9-,13-12-,16-15-

InChI Key

UNSRRHDPHVZAHH-YOILPLPUSA-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

icosatrienoic acid (CHEBI:72865 )
Unsaturated fatty acids (LMFA01030381 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)

Cellular substructure

Membrane (HMDB: HMDB0010378)
Extracellular (HMDB: HMDB0010378)

Source

Exogenous

Exogenous (HMDB: HMDB0010378)

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)

Endogenous

Endogenous (HMDB: HMDB0010378)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Isovaleric acidemia (MarkerDB: MDB00030041)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.3e-05 g/L	ALOGPS
logP	7.35	ALOGPS
logP	6.95	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	4.82	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	15	ChemAxon
Refractivity	98.84 m³·mol⁻¹	ChemAxon
Polarizability	39.08 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]+	184.102	31661259
DarkChem	[M-H]-	185.842	31661259
DeepCCS	[M+H]+	184.522	30932474
DeepCCS	[M-H]-	182.164	30932474
DeepCCS	[M-2H]-	215.049	30932474
DeepCCS	[M+Na]+	190.615	30932474
AllCCS	[M+H]+	184.6	32859911
AllCCS	[M+H-H2O]+	181.6	32859911
AllCCS	[M+NH4]+	187.2	32859911
AllCCS	[M+Na]+	188.0	32859911
AllCCS	[M-H]-	185.2	32859911
AllCCS	[M+Na-2H]-	187.1	32859911
AllCCS	[M+HCOO]-	189.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,8,11-Eicosatrienoic acid	CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(O)=O	3595.2	Standard polar	33892256
5,8,11-Eicosatrienoic acid	CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(O)=O	2195.3	Standard non polar	33892256
5,8,11-Eicosatrienoic acid	CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(O)=O	2331.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5,8,11-Eicosatrienoic acid,1TMS,isomer #1	CCCCCCCC/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2383.8	Semi standard non polar	33892256
5,8,11-Eicosatrienoic acid,1TBDMS,isomer #1	CCCCCCCC/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2629.7	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 - 5,8,11-Eicosatrienoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-9270000000-463f91799534dd9ba1f8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,8,11-Eicosatrienoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0209-9241000000-4adccb37d26c8a88baaf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,8,11-Eicosatrienoic 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8,11-Eicosatrienoic acid 10V, Positive-QTOF	splash10-000i-0092000000-602cfb1975c490e3881a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8,11-Eicosatrienoic acid 20V, Positive-QTOF	splash10-03ds-3490000000-1350ff64ed6aa1f5820a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8,11-Eicosatrienoic acid 40V, Positive-QTOF	splash10-05mp-9860000000-d900ed087b26c9530957	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8,11-Eicosatrienoic acid 10V, Negative-QTOF	splash10-0a4i-0039000000-659857ef79dd2148ca8d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8,11-Eicosatrienoic acid 20V, Negative-QTOF	splash10-0bti-1095000000-43d44a6c226a6b2adffe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8,11-Eicosatrienoic acid 40V, Negative-QTOF	splash10-0a4l-9140000000-3585933dc08c1124a8e8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8,11-Eicosatrienoic acid 10V, Positive-QTOF	splash10-0a4r-3496000000-59740f5ce9cee4674e11	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8,11-Eicosatrienoic acid 20V, Positive-QTOF	splash10-0a4r-9841000000-2a63f76b4744a3c7d280	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8,11-Eicosatrienoic acid 40V, Positive-QTOF	splash10-05nf-9300000000-2f17ca6393b3b1176c7a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8,11-Eicosatrienoic acid 10V, Negative-QTOF	splash10-0a4i-0019000000-22be6eda7da2c017414e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8,11-Eicosatrienoic acid 20V, Negative-QTOF	splash10-0a4i-2069000000-f9c4ad2fc23eeba4a000	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8,11-Eicosatrienoic acid 40V, Negative-QTOF	splash10-052f-9120000000-d8a09defc53f04953c55	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.095 +/- 0.012 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.987 +/- 0.45 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	4.274 +/- 4.372 uM	Adult (>18 years old)	Female	Normal	9368807	details
Blood	Detected and Quantified	1.316 +/- 1.365 uM	Adult (>18 years old)	Both	Normal	18953024	details
Blood	Detected and Quantified	10.7 +/- 4.4 uM	Adult (>18 years old)	Not Specified	Normal	27329611	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	6.3 +/- 3.8 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
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Not Specified	Premature neonates	23210743	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

Not Available

KNApSAcK ID

C00052345

Chemspider ID

4471956

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5312531

PDB ID

Not Available

ChEBI ID

72865

Food Biomarker Ontology

Not Available

VMH ID

M02457

MarkerDB ID

MDB00030041

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 5,8,11-Eicosatrienoic acid (HMDB0010378)

MOL for HMDB0010378 (5,8,11-Eicosatrienoic acid)

3D MOL for HMDB0010378 (5,8,11-Eicosatrienoic acid)

3D SDF for HMDB0010378 (5,8,11-Eicosatrienoic acid)

3D-SDF for HMDB0010378 (5,8,11-Eicosatrienoic acid)

PDB for HMDB0010378 (5,8,11-Eicosatrienoic acid)

3D PDB for HMDB0010378 (5,8,11-Eicosatrienoic acid)

SMILES for HMDB0010378 (5,8,11-Eicosatrienoic acid)

INCHI for HMDB0010378 (5,8,11-Eicosatrienoic acid)

Structure for HMDB0010378 (5,8,11-Eicosatrienoic acid)

3D Structure for HMDB0010378 (5,8,11-Eicosatrienoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra