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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:39 UTC

Update Date

2022-03-07 02:49:13 UTC

HMDB ID

HMDB0002177

Secondary Accession Numbers

HMDB02177

Metabolite Identification

Common Name

Cis-8,11,14,17-Eicosatetraenoic acid

Description

Cis-8,11,14,17-Eicosatetraenoic acid is an eicosanoid present in marine lipids, a minor n-3 polyunsaturated fatty acid (PUFA) which is a position isomer of 20:4n-6. n-3 PUFA contained in marine lipids appear to have a protective effect against coronary heart disease and thrombosis. Human platelets metabolize 8,11,14,17-eicosatetraenoic acid primarily into 12-hydroxy-8,10,14,17-eicosatetraenoic acid. The eicosanoids are a diverse family of molecules that have powerful effects on cell function. They are best known as intercellular messengers, having autocrine and paracrine effects following their secretion from the cells that synthesize them. The diversity of possible products that can be synthesized from eicosatrienoic acid is due, in part to the variety of enzymes that can act on it. Studies have placed many, but not all, of these enzymes at or inside the nucleus. In some cases, the nuclear import or export of eicosatrienoic acid-processing enzymes is highly regulated. Furthermore, nuclear receptors that are activated by specific eicosanoids are known to exist. Taken together, these findings indicate that the enzymatic conversion of eicosatrienoic acid to specific signaling molecules can occur in the nucleus, that it is regulated, and that the synthesized products may act within the nucleus. PMID: 3109494 , 8142566 , 16574479 , 15896193 , 10037447 ). Trans fatty acids are characteristically produced during industrial hydrogenation of plant oils.

Structure

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

HMDB0002177
     RDKit          3D
Cis-8,11,14,17-Eicosatetraenoic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
    7.2867    2.0850    2.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6387    0.7142    2.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7447    0.3782    1.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6801    0.1772    0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2798    0.2556    0.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5586   -1.0269    0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5127   -1.0945   -0.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9314    0.0593   -1.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9478   -0.2352   -2.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8967   -0.2790   -3.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4568   -0.0321   -2.6747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2612   -1.2443   -2.9090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8155   -1.9155   -1.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7226   -1.5683   -0.5392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2158   -1.3484   -0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6991   -0.2517   -0.9504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0793    0.2201   -0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7188    0.7584    0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8926   -0.2066    1.3895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5666    0.4906    2.5300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8676    1.6876    2.4143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8263   -0.2294    3.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5325    2.8910    2.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1013    2.2599    1.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7028    2.0230    3.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2996   -0.0626    2.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6869    0.6217    2.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7556    0.2903    0.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9210   -0.0701   -0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2716    0.3820    1.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7628    1.1559    0.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8790   -1.9461    0.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9717   -2.0460   -0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9313    0.2104   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4517    1.0122   -0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9299   -0.4259   -2.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0325   -0.5121   -4.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025    0.7431   -3.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5470    0.4553   -1.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3483   -1.5321   -3.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4056   -2.8191   -2.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4113   -2.4516    0.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2368   -0.6506   -0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0621   -1.1058    0.9832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7343   -2.2926   -0.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5131   -0.6022   -2.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9712    0.6175   -0.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1499    1.0295   -1.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7755   -0.5809   -1.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7739    1.0928   -0.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2693    1.7350    0.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6405   -0.9864    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0504   -0.7794    1.7421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7937    0.1216    4.6014 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  2  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
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 22 54  1  0
M  END

  Mrv0541 02231219242D          

 22 21  0  0  0  0            999 V2000
    4.4122  -12.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1267  -11.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8412  -12.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5556  -12.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2701  -11.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9846  -12.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6991  -12.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4136  -11.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1281  -12.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8425  -12.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5570  -11.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2715  -12.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9859  -12.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7004  -11.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4149  -12.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1294  -11.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8439  -12.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5583  -11.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2728  -12.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9873  -11.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7017  -12.1441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9873  -10.9066    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  2  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  2  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  1  0  0  0  0
 20 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002177

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13H,2,5,8,11,14-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-

> <INCHI_KEY>
HQPCSDADVLFHHO-LTKCOYKYSA-N

> <FORMULA>
C20H32O2

> <MOLECULAR_WEIGHT>
304.4669

> <EXACT_MASS>
304.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
37.34842805299986

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoic acid

> <ALOGPS_LOGP>
6.83

> <JCHEM_LOGP>
6.587170811

> <ALOGPS_LOGS>
-6.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.885823686047827

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
99.954

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.65e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002177
     RDKit          3D
Cis-8,11,14,17-Eicosatetraenoic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
    7.2867    2.0850    2.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6387    0.7142    2.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7447    0.3782    1.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6801    0.1772    0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2798    0.2556    0.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5586   -1.0269    0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5127   -1.0945   -0.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9314    0.0593   -1.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9478   -0.2352   -2.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8967   -0.2790   -3.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4568   -0.0321   -2.6747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2612   -1.2443   -2.9090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8155   -1.9155   -1.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7226   -1.5683   -0.5392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2158   -1.3484   -0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6991   -0.2517   -0.9504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0793    0.2201   -0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7188    0.7584    0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8926   -0.2066    1.3895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5666    0.4906    2.5300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8676    1.6876    2.4143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8263   -0.2294    3.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5325    2.8910    2.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1013    2.2599    1.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7028    2.0230    3.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2996   -0.0626    2.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6869    0.6217    2.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7556    0.2903    0.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9210   -0.0701   -0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2716    0.3820    1.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7628    1.1559    0.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8790   -1.9461    0.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9717   -2.0460   -0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9313    0.2104   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4517    1.0122   -0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9299   -0.4259   -2.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0325   -0.5121   -4.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025    0.7431   -3.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5470    0.4553   -1.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3483   -1.5321   -3.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4056   -2.8191   -2.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4113   -2.4516    0.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2368   -0.6506   -0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0621   -1.1058    0.9832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7343   -2.2926   -0.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5131   -0.6022   -2.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9712    0.6175   -0.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1499    1.0295   -1.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7755   -0.5809   -1.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7739    1.0928   -0.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2693    1.7350    0.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6405   -0.9864    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0504   -0.7794    1.7421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7937    0.1216    4.6014 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  2  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
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 22 54  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       8.236 -22.669   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.570 -21.899   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.904 -22.669   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.237 -22.669   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.571 -21.899   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.905 -22.669   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.238 -22.669   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.572 -21.899   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.906 -22.669   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.239 -22.669   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.573 -21.899   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.907 -22.669   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.240 -22.669   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.574 -21.899   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.908 -22.669   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.242 -21.899   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.575 -22.669   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.909 -21.899   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      32.243 -22.669   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      33.576 -21.899   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      34.910 -22.669   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      33.576 -20.359   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    HMDB0002177
HETATM    1  C1  UNL     1       7.287   2.085   2.675  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.639   0.714   2.424  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.745   0.378   1.004  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.680   0.177   0.251  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.280   0.256   0.701  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.559  -1.027   0.494  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.513  -1.095  -0.277  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.931   0.059  -1.022  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.948  -0.235  -2.461  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.897  -0.279  -3.205  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.457  -0.032  -2.675  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.261  -1.244  -2.909  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.815  -1.915  -1.957  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.723  -1.568  -0.539  1.00  0.00           C  
HETATM   15  C15 UNL     1      -3.216  -1.348  -0.096  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.699  -0.252  -0.950  1.00  0.00           C  
HETATM   17  C17 UNL     1      -5.079   0.220  -0.914  1.00  0.00           C  
HETATM   18  C18 UNL     1      -5.719   0.758   0.288  1.00  0.00           C  
HETATM   19  C19 UNL     1      -5.893  -0.207   1.390  1.00  0.00           C  
HETATM   20  C20 UNL     1      -6.567   0.491   2.530  1.00  0.00           C  
HETATM   21  O1  UNL     1      -6.868   1.688   2.414  1.00  0.00           O  
HETATM   22  O2  UNL     1      -6.826  -0.229   3.667  1.00  0.00           O  
HETATM   23  H1  UNL     1       6.533   2.891   2.572  1.00  0.00           H  
HETATM   24  H2  UNL     1       8.101   2.260   1.965  1.00  0.00           H  
HETATM   25  H3  UNL     1       7.703   2.023   3.710  1.00  0.00           H  
HETATM   26  H4  UNL     1       7.300  -0.063   2.954  1.00  0.00           H  
HETATM   27  H5  UNL     1       5.687   0.622   2.908  1.00  0.00           H  
HETATM   28  H6  UNL     1       7.756   0.290   0.550  1.00  0.00           H  
HETATM   29  H7  UNL     1       5.921  -0.070  -0.808  1.00  0.00           H  
HETATM   30  H8  UNL     1       4.272   0.382   1.826  1.00  0.00           H  
HETATM   31  H9  UNL     1       3.763   1.156   0.349  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.879  -1.946   0.978  1.00  0.00           H  
HETATM   33  H11 UNL     1       1.972  -2.046  -0.433  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.931   0.210  -0.572  1.00  0.00           H  
HETATM   35  H13 UNL     1       2.452   1.012  -0.895  1.00  0.00           H  
HETATM   36  H14 UNL     1       2.930  -0.426  -2.904  1.00  0.00           H  
HETATM   37  H15 UNL     1       1.032  -0.512  -4.285  1.00  0.00           H  
HETATM   38  H16 UNL     1      -0.902   0.743  -3.411  1.00  0.00           H  
HETATM   39  H17 UNL     1      -0.547   0.455  -1.726  1.00  0.00           H  
HETATM   40  H18 UNL     1      -1.348  -1.532  -3.981  1.00  0.00           H  
HETATM   41  H19 UNL     1      -2.406  -2.819  -2.216  1.00  0.00           H  
HETATM   42  H20 UNL     1      -1.411  -2.452   0.060  1.00  0.00           H  
HETATM   43  H21 UNL     1      -1.237  -0.651  -0.262  1.00  0.00           H  
HETATM   44  H22 UNL     1      -3.062  -1.106   0.983  1.00  0.00           H  
HETATM   45  H23 UNL     1      -3.734  -2.293  -0.171  1.00  0.00           H  
HETATM   46  H24 UNL     1      -3.513  -0.602  -2.031  1.00  0.00           H  
HETATM   47  H25 UNL     1      -2.971   0.617  -0.876  1.00  0.00           H  
HETATM   48  H26 UNL     1      -5.150   1.029  -1.738  1.00  0.00           H  
HETATM   49  H27 UNL     1      -5.776  -0.581  -1.375  1.00  0.00           H  
HETATM   50  H28 UNL     1      -6.774   1.093  -0.005  1.00  0.00           H  
HETATM   51  H29 UNL     1      -5.269   1.735   0.631  1.00  0.00           H  
HETATM   52  H30 UNL     1      -6.641  -0.986   1.024  1.00  0.00           H  
HETATM   53  H31 UNL     1      -5.050  -0.779   1.742  1.00  0.00           H  
HETATM   54  H32 UNL     1      -6.794   0.122   4.601  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   13   40
CONECT   13   14   41
CONECT   14   15   42   43
CONECT   15   16   44   45
CONECT   16   17   46   47
CONECT   17   18   48   49
CONECT   18   19   50   51
CONECT   19   20   52   53
CONECT   20   21   21   22
CONECT   22   54
END

HMDB0002177
     RDKit          3D
Cis-8,11,14,17-Eicosatetraenoic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
    7.2867    2.0850    2.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6387    0.7142    2.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7447    0.3782    1.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6801    0.1772    0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2798    0.2556    0.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5586   -1.0269    0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5127   -1.0945   -0.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9314    0.0593   -1.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9478   -0.2352   -2.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8967   -0.2790   -3.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4568   -0.0321   -2.6747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2612   -1.2443   -2.9090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8155   -1.9155   -1.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7226   -1.5683   -0.5392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2158   -1.3484   -0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6991   -0.2517   -0.9504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0793    0.2201   -0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7188    0.7584    0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8926   -0.2066    1.3895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5666    0.4906    2.5300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8676    1.6876    2.4143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8263   -0.2294    3.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5325    2.8910    2.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1013    2.2599    1.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7028    2.0230    3.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2996   -0.0626    2.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6869    0.6217    2.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7556    0.2903    0.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9210   -0.0701   -0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2716    0.3820    1.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7628    1.1559    0.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8790   -1.9461    0.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9717   -2.0460   -0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9313    0.2104   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4517    1.0122   -0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9299   -0.4259   -2.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0325   -0.5121   -4.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025    0.7431   -3.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5470    0.4553   -1.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3483   -1.5321   -3.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4056   -2.8191   -2.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4113   -2.4516    0.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2368   -0.6506   -0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0621   -1.1058    0.9832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7343   -2.2926   -0.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5131   -0.6022   -2.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9712    0.6175   -0.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1499    1.0295   -1.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7755   -0.5809   -1.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7739    1.0928   -0.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2693    1.7350    0.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6405   -0.9864    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0504   -0.7794    1.7421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7937    0.1216    4.6014 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  2  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
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 22 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(8Z,11Z,14Z,17Z)-Eicosa-8,11,14,17-tetraenoic acid	ChEBI
(8Z,11Z,14Z,17Z)-Eicosatetraenoic acid	ChEBI
(8Z,11Z,14Z,17Z)-Icosatetraenoic acid	ChEBI
(Z,Z,Z,Z)-Eicosa-8,11,14,17-tetraenoic acid	ChEBI
(Z,Z,Z,Z)-Icosa-8,11,14,17-tetraenoic acid	ChEBI
8Z,11Z,14Z,17Z-Eicosatetraenoic acid	ChEBI
all-cis-8,11,14,17-Eicosatetraenoic acid	ChEBI
all-Z-8,11,14,17-Eicosatetraenoic acid	ChEBI
all-Z-8,11,14,17-Icosatetraenoic acid	ChEBI
ETA	ChEBI
Omega-3-arachidonic acid	ChEBI
(8Z,11Z,14Z,17Z)-Eicosa-8,11,14,17-tetraenoate	Generator
(8Z,11Z,14Z,17Z)-Eicosatetraenoate	Generator
(8Z,11Z,14Z,17Z)-Icosatetraenoate	Generator
(Z,Z,Z,Z)-Eicosa-8,11,14,17-tetraenoate	Generator
(Z,Z,Z,Z)-Icosa-8,11,14,17-tetraenoate	Generator
8Z,11Z,14Z,17Z-Eicosatetraenoate	Generator
all-cis-8,11,14,17-Eicosatetraenoate	Generator
all-Z-8,11,14,17-Eicosatetraenoate	Generator
all-Z-8,11,14,17-Icosatetraenoate	Generator
Omega-3-arachidonate	Generator
cis-8,11,14,17-Eicosatetraenoate	Generator
8, 11, 14, 17-Icosatetraenoate	HMDB
8, 11, 14, 17-Icosatetraenoic acid	HMDB
8,11,14,17-Eicosatetraenoate	HMDB
8,11,14,17-Eicosatetraenoic acid	HMDB
8,11,14,17-Eicosatetraenoic acid, Z-isomer	HMDB

Chemical Formula

C₂₀H₃₂O₂

Average Molecular Weight

304.4669

Monoisotopic Molecular Weight

304.240230268

IUPAC Name

(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoic acid

Traditional Name

(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoic acid

CAS Registry Number

2091-26-1

SMILES

CC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCC(O)=O

InChI Identifier

InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13H,2,5,8,11,14-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-

InChI Key

HQPCSDADVLFHHO-LTKCOYKYSA-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:71488 )
icosatetraenoic acid (CHEBI:71488 )
Unsaturated fatty acids (LMFA01030818 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)

Cellular substructure

Extracellular (HMDB: HMDB0002177)
Membrane (HMDB: HMDB0002177)

Source

Exogenous

Exogenous (HMDB: HMDB0002177)

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Endogenous (HMDB: HMDB0002177)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Alpha Linolenic Acid and Linoleic Acid Metabolism (PathBank: SMP0087171)

Role

Not Available

Physical Properties

State

Liquid

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	187.333	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001908
[M+H]+	Not Available	178.6	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001908

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00016 g/L	ALOGPS
logP	6.83	ALOGPS
logP	6.59	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	4.89	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	14	ChemAxon
Refractivity	99.95 m³·mol⁻¹	ChemAxon
Polarizability	37.35 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]+	184.913	31661259
DarkChem	[M-H]-	183.402	31661259
DeepCCS	[M+H]+	180.728	30932474
DeepCCS	[M-H]-	178.37	30932474
DeepCCS	[M-2H]-	211.257	30932474
DeepCCS	[M+Na]+	186.821	30932474
AllCCS	[M+H]+	182.8	32859911
AllCCS	[M+H-H2O]+	179.8	32859911
AllCCS	[M+NH4]+	185.6	32859911
AllCCS	[M+Na]+	186.4	32859911
AllCCS	[M-H]-	183.4	32859911
AllCCS	[M+Na-2H]-	185.2	32859911
AllCCS	[M+HCOO]-	187.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cis-8,11,14,17-Eicosatetraenoic acid	CC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCC(O)=O	3738.9	Standard polar	33892256
Cis-8,11,14,17-Eicosatetraenoic acid	CC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCC(O)=O	2160.6	Standard non polar	33892256
Cis-8,11,14,17-Eicosatetraenoic acid	CC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCC(O)=O	2332.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cis-8,11,14,17-Eicosatetraenoic acid,1TMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C	2385.2	Semi standard non polar	33892256
Cis-8,11,14,17-Eicosatetraenoic acid,1TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2627.8	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 - Cis-8,11,14,17-Eicosatetraenoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-6790000000-9f82428f04530524e4d2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-01w0-7962000000-84eacc6d7a7ceee0c99a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic 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 - Cis-8,11,14,17-Eicosatetraenoic acid Linear Ion Trap , negative-QTOF	splash10-0a4i-0090000000-ac340d2fdec196225551	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid Linear Ion Trap , positive-QTOF	splash10-002f-0591000000-9c83feea251cbef18bac	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid Linear Ion Trap , positive-QTOF	splash10-059m-0491000000-c78942db68649dad3705	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 10V, Negative-QTOF	splash10-0udi-0039000000-057a58eb03c1d61d43f9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 20V, Negative-QTOF	splash10-0zg0-1095000000-a5e878ae7122108346ea	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 40V, Negative-QTOF	splash10-0a4l-9240000000-d349b1db215c158d4b05	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 10V, Negative-QTOF	splash10-0udi-0019000000-e301ae96559ee65daa0e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 20V, Negative-QTOF	splash10-0udr-2069000000-b0db6033219193d0d9e4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 40V, Negative-QTOF	splash10-006x-9320000000-58917ba5f6a987214949	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 10V, Positive-QTOF	splash10-052r-0092000000-adcd16a168a2136833fa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 20V, Positive-QTOF	splash10-0a4r-4691000000-e3736249247ab6a17228	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 40V, Positive-QTOF	splash10-052n-8950000000-af9e1166c7a23305f645	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 10V, Positive-QTOF	splash10-0a4r-4796000000-26f15a5b60f20cad946e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 20V, Positive-QTOF	splash10-001l-7910000000-dcb9693160ae6a462cd8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-8,11,14,17-Eicosatetraenoic acid 40V, Positive-QTOF	splash10-0036-9300000000-a07065b94af0ab13e426	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
alpha-Linolenic acid metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.007 (0 - 0.014) uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details

Abnormal Concentrations

Not Available

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

FDB022887

KNApSAcK ID

Not Available

Chemspider ID

9897310

KEGG Compound ID

Not Available

BioCyc ID

CPD-8121

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11722594

PDB ID

Not Available

ChEBI ID

71488

Food Biomarker Ontology

Not Available

VMH ID

EICOSTET

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Careaga MM, Sprecher H: Metabolism of 8,11,14,17-eicosatetraenoic acid by human platelet lipoxygenase and cyclooxygenase. Biochim Biophys Acta. 1987 Jul 13;920(1):94-101. [PubMed:3109494 ]
Loick HM, Theissen JL: [Eicosanoids as mediators in ARDS]. Anasthesiol Intensivmed Notfallmed Schmerzther. 1994 Feb;29(1):3-9. [PubMed:8142566 ]
Luo M, Flamand N, Brock TG: Metabolism of arachidonic acid to eicosanoids within the nucleus. Biochim Biophys Acta. 2006 May-Jun;1761(5-6):618-25. Epub 2006 Mar 20. [PubMed:16574479 ]
Charbeneau RP, Peters-Golden M: Eicosanoids: mediators and therapeutic targets in fibrotic lung disease. Clin Sci (Lond). 2005 Jun;108(6):479-91. [PubMed:15896193 ]
Croset M, Bordet JC, Lagarde M: Inhibition of prostaglandin H synthase and activation of 12-lipoxygenase by 8,11,14,17-eicosatetraenoic acid in human endothelial cells and platelets. Biochem Pharmacol. 1999 Mar 15;57(6):631-8. [PubMed:10037447 ]

Showing metabocard for Cis-8,11,14,17-Eicosatetraenoic acid (HMDB0002177)

MOL for HMDB0002177 (Cis-8,11,14,17-Eicosatetraenoic acid)

3D MOL for HMDB0002177 (Cis-8,11,14,17-Eicosatetraenoic acid)

3D SDF for HMDB0002177 (Cis-8,11,14,17-Eicosatetraenoic acid)

3D-SDF for HMDB0002177 (Cis-8,11,14,17-Eicosatetraenoic acid)

PDB for HMDB0002177 (Cis-8,11,14,17-Eicosatetraenoic acid)

3D PDB for HMDB0002177 (Cis-8,11,14,17-Eicosatetraenoic acid)

SMILES for HMDB0002177 (Cis-8,11,14,17-Eicosatetraenoic acid)

INCHI for HMDB0002177 (Cis-8,11,14,17-Eicosatetraenoic acid)

Structure for HMDB0002177 (Cis-8,11,14,17-Eicosatetraenoic acid)

3D Structure for HMDB0002177 (Cis-8,11,14,17-Eicosatetraenoic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra