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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2013-05-01 17:29:32 UTC

Update Date

2022-09-22 17:44:09 UTC

HMDB ID

HMDB0060039

Secondary Accession Numbers

HMDB60039

Metabolite Identification

Common Name

Dihomo-alpha-linolenic acid

Description

Dihomo-alpha-linolenic acid, also known as 11,14,17-eicosatrienoic acid, is a rare polyunsaturated fatty acid of the omega-3 series. In normal humans, it represents less than 0.25% of serum phospholipid fatty acids. However, it is one of the most active essential fatty acids when assayed for the inhibition of fatty acid elongation/desaturation reactions which convert dietary C-18 fatty acids to C-20 eicosanoid precursors. (http://www.caymanchem.com)

Structure

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

HMDB0060039
     RDKit          3D
Dihomo-alpha-linolenic acid
 56 55  0  0  0  0  0  0  0  0999 V2000
    4.1529    2.4929   -2.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6854    1.3269   -1.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2925    0.0562   -1.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0597   -0.7337   -0.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4097   -0.3950    0.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9480   -1.4219    1.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1022   -1.2394    2.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4953    0.0277    2.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0810    0.2773    2.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1003   -0.4655    2.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2099   -1.8399    1.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6697   -1.9021    0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7684   -1.4842    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4002   -1.5399   -1.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8481   -1.1266   -0.9663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0626    0.2610   -0.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5324    0.6559   -0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1965    0.6161   -1.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6406    1.0117   -1.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8273    2.3879   -1.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8802    3.1715   -0.9962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1114    2.8967   -0.9724 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8326    3.1646   -1.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2846    3.1122   -2.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7328    2.0985   -2.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7177    1.5410   -0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5732    1.2270   -1.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0654   -0.2470   -2.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4560   -1.6484   -1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5573   -0.4713    0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1923    0.6033    0.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3310   -2.4691    1.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8833   -2.1227    3.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1046    0.8766    2.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7474    0.1825    3.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7268    1.3192    2.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0449   -0.0207    2.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3826   -2.4100    2.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1423   -2.3588    1.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7633   -2.9105   -0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2545   -1.1490   -0.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3622   -2.1260    1.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8774   -0.4150    0.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759   -2.5473   -1.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8479   -0.8397   -1.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3596   -1.3252   -1.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3705   -1.8116   -0.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5071    0.9995   -1.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7153    0.3811    0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5666    1.6691   -0.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0855    0.0128    0.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1009   -0.3729   -2.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7145    1.3354   -2.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1111    0.8478   -2.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1620    0.3245   -0.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6749    2.5166   -0.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  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
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 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


  Mrv1652302102020362D          

 22 21  0  0  0  0            999 V2000
 9997.1024 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8173 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5323 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2468 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0717 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7874 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.5031 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.3280 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.0437 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.7573 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.5823 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.2979 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.0156 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.3876 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6728 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.9578 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.2429 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.5281 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8133 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.0983 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.3814 9998.0698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.0983 9999.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 14  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  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  1  0  0  0  0
 20 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060039

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C=C/C\C=C/C\C=C/CCCCCCCCCC(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/h3-4,6-7,9-10H,2,5,8,11-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-

> <INCHI_KEY>
AHANXAKGNAKFSK-PDBXOOCHSA-N

> <FORMULA>
C20H34O2

> <MOLECULAR_WEIGHT>
306.4828

> <EXACT_MASS>
306.255880332

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.73490615526083

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(11Z,14Z,17Z)-icosa-11,14,17-trienoic acid

> <ALOGPS_LOGP>
7.24

> <JCHEM_LOGP>
6.9490924676666666

> <ALOGPS_LOGS>
-6.60

> <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>
98.83739999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.73e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
eicosatrienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060039
     RDKit          3D
Dihomo-alpha-linolenic acid
 56 55  0  0  0  0  0  0  0  0999 V2000
    4.1529    2.4929   -2.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6854    1.3269   -1.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2925    0.0562   -1.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0597   -0.7337   -0.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4097   -0.3950    0.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9480   -1.4219    1.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1022   -1.2394    2.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4953    0.0277    2.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0810    0.2773    2.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1003   -0.4655    2.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2099   -1.8399    1.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6697   -1.9021    0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7684   -1.4842    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4002   -1.5399   -1.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8481   -1.1266   -0.9663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0626    0.2610   -0.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5324    0.6559   -0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1965    0.6161   -1.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6406    1.0117   -1.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8273    2.3879   -1.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8802    3.1715   -0.9962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1114    2.8967   -0.9724 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8326    3.1646   -1.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2846    3.1122   -2.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7328    2.0985   -2.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7177    1.5410   -0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5732    1.2270   -1.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0654   -0.2470   -2.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4560   -1.6484   -1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5573   -0.4713    0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1923    0.6033    0.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3310   -2.4691    1.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8833   -2.1227    3.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1046    0.8766    2.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7474    0.1825    3.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7268    1.3192    2.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0449   -0.0207    2.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3826   -2.4100    2.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1423   -2.3588    1.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7633   -2.9105   -0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2545   -1.1490   -0.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3622   -2.1260    1.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8774   -0.4150    0.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759   -2.5473   -1.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8479   -0.8397   -1.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3596   -1.3252   -1.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3705   -1.8116   -0.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5071    0.9995   -1.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7153    0.3811    0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5666    1.6691   -0.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0855    0.0128    0.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1009   -0.3729   -2.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7145    1.3354   -2.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1111    0.8478   -2.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1620    0.3245   -0.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6749    2.5166   -0.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  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
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 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                                 10-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-FEB-20         0                                  
HETATM    1  C   UNK     0    8661.2588663.064   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.5928663.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8663.9278663.064   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8665.2618663.832   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8666.8018663.832   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8668.1368663.064   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8669.4728663.832   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8671.0128663.832   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8672.3488663.064   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8673.6808663.832   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8675.2208663.832   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8676.5568663.064   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8677.8968663.832   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8659.9248663.832   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8658.5898663.064   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8657.2558663.832   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8655.9208663.064   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8654.5868663.832   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8653.2518663.064   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8651.9178663.832   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8650.5798663.064   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0    8651.9178665.373   0.000  0.00  0.00           O+0
CONECT    1    2   14                                                       
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                                                            
CONECT   14    1   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    HMDB0060039
HETATM    1  C1  UNL     1       4.153   2.493  -2.071  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.685   1.327  -1.213  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.292   0.056  -1.641  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.060  -0.734  -0.922  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.410  -0.395   0.483  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.948  -1.422   1.435  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.102  -1.239   2.431  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.495   0.028   2.736  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.081   0.277   2.658  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.100  -0.465   2.271  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.210  -1.840   1.780  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.670  -1.902   0.333  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.768  -1.484   0.366  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.400  -1.540  -1.015  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.848  -1.127  -0.966  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.063   0.261  -0.465  1.00  0.00           C  
HETATM   17  C17 UNL     1      -4.532   0.656  -0.431  1.00  0.00           C  
HETATM   18  C18 UNL     1      -5.196   0.616  -1.759  1.00  0.00           C  
HETATM   19  C19 UNL     1      -6.641   1.012  -1.668  1.00  0.00           C  
HETATM   20  C20 UNL     1      -6.827   2.388  -1.205  1.00  0.00           C  
HETATM   21  O1  UNL     1      -5.880   3.172  -0.996  1.00  0.00           O  
HETATM   22  O2  UNL     1      -8.111   2.897  -0.972  1.00  0.00           O  
HETATM   23  H1  UNL     1       4.833   3.165  -1.509  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.285   3.112  -2.356  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.733   2.098  -2.929  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.718   1.541  -0.141  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.573   1.227  -1.431  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.065  -0.247  -2.683  1.00  0.00           H  
HETATM   29  H7  UNL     1       5.456  -1.648  -1.331  1.00  0.00           H  
HETATM   30  H8  UNL     1       6.557  -0.471   0.534  1.00  0.00           H  
HETATM   31  H9  UNL     1       5.192   0.603   0.796  1.00  0.00           H  
HETATM   32  H10 UNL     1       5.331  -2.469   1.333  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.883  -2.123   3.113  1.00  0.00           H  
HETATM   34  H12 UNL     1       4.105   0.877   2.279  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.747   0.182   3.880  1.00  0.00           H  
HETATM   36  H14 UNL     1       1.727   1.319   2.993  1.00  0.00           H  
HETATM   37  H15 UNL     1       0.045  -0.021   2.331  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.383  -2.410   2.347  1.00  0.00           H  
HETATM   39  H17 UNL     1       2.142  -2.359   1.852  1.00  0.00           H  
HETATM   40  H18 UNL     1       0.763  -2.911  -0.068  1.00  0.00           H  
HETATM   41  H19 UNL     1       1.254  -1.149  -0.261  1.00  0.00           H  
HETATM   42  H20 UNL     1      -1.362  -2.126   1.036  1.00  0.00           H  
HETATM   43  H21 UNL     1      -0.877  -0.415   0.672  1.00  0.00           H  
HETATM   44  H22 UNL     1      -1.276  -2.547  -1.416  1.00  0.00           H  
HETATM   45  H23 UNL     1      -0.848  -0.840  -1.693  1.00  0.00           H  
HETATM   46  H24 UNL     1      -3.360  -1.325  -1.928  1.00  0.00           H  
HETATM   47  H25 UNL     1      -3.371  -1.812  -0.234  1.00  0.00           H  
HETATM   48  H26 UNL     1      -2.507   0.999  -1.074  1.00  0.00           H  
HETATM   49  H27 UNL     1      -2.715   0.381   0.590  1.00  0.00           H  
HETATM   50  H28 UNL     1      -4.567   1.669  -0.006  1.00  0.00           H  
HETATM   51  H29 UNL     1      -5.085   0.013   0.317  1.00  0.00           H  
HETATM   52  H30 UNL     1      -5.101  -0.373  -2.263  1.00  0.00           H  
HETATM   53  H31 UNL     1      -4.715   1.335  -2.485  1.00  0.00           H  
HETATM   54  H32 UNL     1      -7.111   0.848  -2.669  1.00  0.00           H  
HETATM   55  H33 UNL     1      -7.162   0.324  -0.931  1.00  0.00           H  
HETATM   56  H34 UNL     1      -8.675   2.517  -0.223  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4    4   28
CONECT    4    5   29
CONECT    5    6   30   31
CONECT    6    7    7   32
CONECT    7    8   33
CONECT    8    9   34   35
CONECT    9   10   10   36
CONECT   10   11   37
CONECT   11   12   38   39
CONECT   12   13   40   41
CONECT   13   14   42   43
CONECT   14   15   44   45
CONECT   15   16   46   47
CONECT   16   17   48   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

HMDB0060039
     RDKit          3D
Dihomo-alpha-linolenic acid
 56 55  0  0  0  0  0  0  0  0999 V2000
    4.1529    2.4929   -2.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6854    1.3269   -1.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2925    0.0562   -1.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0597   -0.7337   -0.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4097   -0.3950    0.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9480   -1.4219    1.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1022   -1.2394    2.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4953    0.0277    2.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0810    0.2773    2.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1003   -0.4655    2.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2099   -1.8399    1.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6697   -1.9021    0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7684   -1.4842    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4002   -1.5399   -1.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8481   -1.1266   -0.9663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0626    0.2610   -0.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5324    0.6559   -0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1965    0.6161   -1.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6406    1.0117   -1.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8273    2.3879   -1.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8802    3.1715   -0.9962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1114    2.8967   -0.9724 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8326    3.1646   -1.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2846    3.1122   -2.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7328    2.0985   -2.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7177    1.5410   -0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5732    1.2270   -1.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0654   -0.2470   -2.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4560   -1.6484   -1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5573   -0.4713    0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1923    0.6033    0.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3310   -2.4691    1.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8833   -2.1227    3.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1046    0.8766    2.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7474    0.1825    3.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7268    1.3192    2.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0449   -0.0207    2.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3826   -2.4100    2.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1423   -2.3588    1.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7633   -2.9105   -0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2545   -1.1490   -0.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3622   -2.1260    1.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8774   -0.4150    0.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759   -2.5473   -1.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8479   -0.8397   -1.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3596   -1.3252   -1.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3705   -1.8116   -0.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5071    0.9995   -1.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7153    0.3811    0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5666    1.6691   -0.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0855    0.0128    0.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1009   -0.3729   -2.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7145    1.3354   -2.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1111    0.8478   -2.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1620    0.3245   -0.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6749    2.5166   -0.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  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
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 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
(11Z,14Z,17Z)-Eicosa-11,14,17-trienoic acid	ChEBI
(11Z,14Z,17Z)-Icosa-11,14,17-trienoic acid	ChEBI
(Z,Z,Z)-11,14,17-Eicosatrienoic acid	ChEBI
11,14,17-Eicosatrienoic acid	ChEBI
11,14,17-Icosatrienoic acid	ChEBI
11C,14C,17C-Eicosatrienoic acid	ChEBI
11C,14C,17C-Eicosatriensaeure	ChEBI
20:3, N-3,6,9 all-cis	ChEBI
all-cis-11,14,17-Eicosatrienoic acid	ChEBI
all-cis-Eicosa-11,14,17-trienoic acid	ChEBI
all-cis-Eicosa-11,14,17-triensaeure	ChEBI
C20:3, N-3,6,9 all-cis	ChEBI
cis,cis,cis-11,14,17-Eicosatrienoic acid	ChEBI
Eicosa-11Z,14Z,17Z-trienoic acid	ChEBI
Eicosatrienoic acid	ChEBI
ETA	ChEBI
ETE	ChEBI
(11Z,14Z,17Z)-Eicosa-11,14,17-trienoate	Generator
(11Z,14Z,17Z)-Icosa-11,14,17-trienoate	Generator
(Z,Z,Z)-11,14,17-Eicosatrienoate	Generator
11,14,17-Eicosatrienoate	Generator
11,14,17-Icosatrienoate	Generator
11C,14C,17C-Eicosatrienoate	Generator
all-cis-11,14,17-Eicosatrienoate	Generator
all-cis-Eicosa-11,14,17-trienoate	Generator
cis,cis,cis-11,14,17-Eicosatrienoate	Generator
Eicosa-11Z,14Z,17Z-trienoate	Generator
Eicosatrienoate	Generator
Dihomo-a-linolenate	Generator
Dihomo-a-linolenic acid	Generator
Dihomo-alpha-linolenate	Generator
Dihomo-α-linolenate	Generator
Dihomo-α-linolenic acid	Generator
Dihomolinolenate	HMDB
11,14,17-Eicosatrienoic acid, (Z,Z,Z)-isomer	HMDB
Bishomo-a-linolenate	HMDB
Bishomo-a-linolenic acid	HMDB
Bishomo-alpha-linolenate	HMDB
Bishomo-α-linolenate	HMDB
Bishomo-α-linolenic acid	HMDB
Bishomo-alpha-linolenic acid	HMDB
Dihomo-linolenate	HMDB
Dihomo-linolenic acid	HMDB
Dihomolinolenic acid	HMDB
FA(20:3(11Z,14Z,17Z))	HMDB
FA(20:3n3)	HMDB
Homo-alpha-linolenic acid	HMDB
Homo-α-linolenic acid	HMDB
Dihomo-alpha-linolenic acid	HMDB

Chemical Formula

C₂₀H₃₄O₂

Average Molecular Weight

306.4828

Monoisotopic Molecular Weight

306.255880332

IUPAC Name

(11Z,14Z,17Z)-icosa-11,14,17-trienoic acid

Traditional Name

eicosatrienoic acid

CAS Registry Number

17046-59-2

SMILES

CC\C=C/C\C=C/C\C=C/CCCCCCCCCC(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/h3-4,6-7,9-10H,2,5,8,11-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-

InChI Key

AHANXAKGNAKFSK-PDBXOOCHSA-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

omega-3 fatty acid (CHEBI:53460 )
icosatrienoic acid (CHEBI:53460 )
Polyunsaturated fatty acids (C16522 )
Unsaturated fatty acids (LMFA01030378 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 20671299)

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0060039)

Excreta

Biofluid or Excreta

Feces (PMID: 22411374)
Urine (HMDB: HMDB0060039)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0060039)

Source

Exogenous

Exogenous (HMDB: HMDB0060039)

Food

Food (HMDB: HMDB0060039)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Herb and spice

Oilseed crop

Evening primrose (FooDB: FOOD00120)

Endogenous

Endogenous (HMDB: HMDB0060039)

Animal

Animal (HMDB: HMDB0060039)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0060039)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0060039)

Lipid metabolism pathway (HMDB: HMDB0060039)

Biochemical process

Lipid transport (HMDB: HMDB0060039)

Role

Biological role

Energy source (HMDB: HMDB0060039)

Physical Properties

State

Not Available

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	7.7e-05 g/L	ALOGPS
logP	7.24	ALOGPS
logP	6.95	ChemAxon
logS	-6.6	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	15	ChemAxon
Refractivity	98.84 m³·mol⁻¹	ChemAxon
Polarizability	38.73 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]+	184.687	31661259
DarkChem	[M-H]-	184.651	31661259
DeepCCS	[M+H]+	182.487	30932474
DeepCCS	[M-H]-	180.129	30932474
DeepCCS	[M-2H]-	213.016	30932474
DeepCCS	[M+Na]+	188.58	30932474
AllCCS	[M+H]+	184.5	32859911
AllCCS	[M+H-H2O]+	181.6	32859911
AllCCS	[M+NH4]+	187.2	32859911
AllCCS	[M+Na]+	188.0	32859911
AllCCS	[M-H]-	185.1	32859911
AllCCS	[M+Na-2H]-	187.0	32859911
AllCCS	[M+HCOO]-	189.2	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.	9.01 minutes	32390414
Predicted by Siyang on May 30, 2022	26.0788 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.65 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3228.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	656.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	263.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	449.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	715.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1182.2 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	776.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	89.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2421.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	770.0 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	1990.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	917.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	550.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	579.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	620.1 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	8.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihomo-alpha-linolenic acid	CC\C=C/C\C=C/C\C=C/CCCCCCCCCC(O)=O	3620.0	Standard polar	33892256
Dihomo-alpha-linolenic acid	CC\C=C/C\C=C/C\C=C/CCCCCCCCCC(O)=O	2226.4	Standard non polar	33892256
Dihomo-alpha-linolenic acid	CC\C=C/C\C=C/C\C=C/CCCCCCCCCC(O)=O	2352.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihomo-alpha-linolenic acid,1TMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCCCC(=O)O[Si](C)(C)C	2410.4	Semi standard non polar	33892256
Dihomo-alpha-linolenic acid,1TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2655.3	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

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	0.341 +/- 0.016 uM	Adult (>18 years old)	Both	Normal	20671299	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB006293

KNApSAcK ID

Not Available

Chemspider ID

4471954

KEGG Compound ID

C16522

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5312529

PDB ID

Not Available

ChEBI ID

53460

Food Biomarker Ontology

Not Available

VMH ID

M00010

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Quehenberger O, Armando AM, Brown AH, Milne SB, Myers DS, Merrill AH, Bandyopadhyay S, Jones KN, Kelly S, Shaner RL, Sullards CM, Wang E, Murphy RC, Barkley RM, Leiker TJ, Raetz CR, Guan Z, Laird GM, Six DA, Russell DW, McDonald JG, Subramaniam S, Fahy E, Dennis EA: Lipidomics reveals a remarkable diversity of lipids in human plasma. J Lipid Res. 2010 Nov;51(11):3299-305. doi: 10.1194/jlr.M009449. Epub 2010 Jul 29. [PubMed:20671299 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Dihomo-alpha-linolenic acid (HMDB0060039)

MOL for HMDB0060039 (Dihomo-alpha-linolenic acid)

3D MOL for HMDB0060039 (Dihomo-alpha-linolenic acid)

3D SDF for HMDB0060039 (Dihomo-alpha-linolenic acid)

3D-SDF for HMDB0060039 (Dihomo-alpha-linolenic acid)

PDB for HMDB0060039 (Dihomo-alpha-linolenic acid)

3D PDB for HMDB0060039 (Dihomo-alpha-linolenic acid)

SMILES for HMDB0060039 (Dihomo-alpha-linolenic acid)

INCHI for HMDB0060039 (Dihomo-alpha-linolenic acid)

Structure for HMDB0060039 (Dihomo-alpha-linolenic acid)

3D Structure for HMDB0060039 (Dihomo-alpha-linolenic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized