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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:11:52 UTC

Update Date

2022-03-07 02:51:28 UTC

HMDB ID

HMDB0013025

Secondary Accession Numbers

HMDB13025

Metabolite Identification

Common Name

6,9,12,15,18,21-Tetracosahexaenoic acid

Description

6,9,12,15,18,21-Tetracosahexaenoic acid (24:6n-3) is one of the n-3 PUFA and is a very long chain fatty acid. Distribution of 24:6n-3 in marine organisms was investigated by several researchers. Takagi et al. reported relatively high contents of 24:6n-3 in sea lilies and brittle stars (4–10% of total fatty acids). High 24:6n-3 content was also found in marine coelenterates. In some edible fishes, 24:6n-3 was detected at significant levels (0–10% of total fatty acids).The existence of 24:6n-3 in mammalian tissues was reported with other very long chain fatty acids in the spermatozoa,the retina, and the brain. Voss et al. reported that 24:6n-3 is formed as an intermediate in the metabolic pathway from 20:5n-3 to 22:6n-3 in rat liver. Even though 24:6n-3 is a PUFA existing in fish and mammalian species, physiological functions of 24:6n-3 have not been studied. As functions to be studied, anti-inflammatory and antiallergic. effects of 24:6n-3 are noteworthy because these events are known to be closely related to the unsaturated fatty acid metabolism such as in the arachidonic acid cascade, and 20:5n-3 and 22:6n-3 were reported to suppress inflammatory actions by influencing arachidonic acid metabolism.s24:6n-3 could inhibit the antigen-stimulated production of LT-related compounds as well as other n-3 polyunsaturated fatty acids (PUFA) such as eicosapentaenoic. acid (20:5n-3) and docosahexaenoic acid (22:6n-3), which are major n-3 PUFA in fish oils; 24:6n-3 was also shown to reduce the histamine content in MC/9 cells at 25 uM (27% reduction from the control), and the effect was diminished with increase of the fatty acid concentration (up to 100 uM). These two n-3 PUFA, 20:5n-3 and 22:6n-3, also reduced the histamine content (16 and 20% reduction at 25 μM, respectively), whereas arachidonic acid (20:4n-6) increased it (18% increase at 25 μM).

Structure

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


  Mrv1652305171803562D          

 26 25  0  0  0  0            999 V2000
    1.7605    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    5.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    6.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    6.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    6.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    6.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    6.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    5.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5263    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5263    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  4  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  4  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 26 24  1  0  0  0  0
M  END

HMDB0013025
     RDKit          3D
6,9,12,15,18,21-Tetracosahexaenoic acid
 62 61  0  0  0  0  0  0  0  0999 V2000
    9.3417   -2.0919    2.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3386   -0.8505    1.6033 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9451   -1.1489    0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9444   -0.6721   -0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9472    0.2940    0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9260    1.5343   -0.7350 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0005    2.0800   -1.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6156    1.7466   -1.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500    0.4819   -1.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1803    0.2625   -0.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3836    1.3791    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9656    1.1331   -0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3578    2.0453   -0.9525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0541    1.7984   -1.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5331    0.5088   -0.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5771    0.4360    0.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0905   -0.8257    0.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5169   -1.0718    0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4617   -1.1936    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8558   -1.4365    0.6720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7862   -0.3454    1.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1927   -0.5830    0.7020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3423   -0.6605   -0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7481   -0.8918   -1.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2663   -2.0302   -1.0898 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5327    0.1260   -1.7174 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8146   -1.8425    3.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3614   -2.4062    2.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8346   -2.9520    1.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4267   -0.5042    1.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7379   -0.0846    2.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5907   -1.8850   -0.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7776   -0.9979   -1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9643   -0.1921    0.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2760    0.5635    1.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9231    2.0698   -0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3086    3.0696   -1.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9645    2.6230   -1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5850    1.6879   -2.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6489   -0.4450   -1.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286   -0.7636   -0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7075    2.3795   -0.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4640    1.3631    1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4645    0.2140    0.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8770    2.9301   -1.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6484    2.6546   -1.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0520    1.7206   -2.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0611   -0.4164   -1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0698    1.3765    0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5164   -1.6864    0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0170   -0.9144    1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7411   -1.1458   -0.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1798   -1.1108    2.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8839   -1.5339   -0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1877   -2.3687    1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7130   -0.2977    2.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4441    0.6602    0.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5940   -1.5207    1.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8694    0.2192    1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7265   -1.4692   -1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0117    0.3028   -1.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0788    0.6791   -1.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 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
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
 23 61  1  0
 26 62  1  0
M  END


  Mrv1652305171803562D          

 26 25  0  0  0  0            999 V2000
    1.7605    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    5.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    6.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    6.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    6.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    6.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    6.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    5.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5263    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5263    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  4  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  4  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 26 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013025

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC=CCC=CCC=CCC=CCC=CCC=CCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-23H2,1H3,(H,25,26)

> <INCHI_KEY>
YHGJECVSSKXFCJ-UHFFFAOYSA-N

> <FORMULA>
C24H36O2

> <MOLECULAR_WEIGHT>
356.55

> <EXACT_MASS>
356.271530399

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.14517895101757

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
tetracosa-6,9,12,15,18,21-hexaenoic acid

> <ALOGPS_LOGP>
7.28

> <JCHEM_LOGP>
7.641602157666666

> <ALOGPS_LOGS>
-6.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.922492763245736

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
120.5912

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.97e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tetracosa-6,9,12,15,18,21-hexaenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013025
     RDKit          3D
6,9,12,15,18,21-Tetracosahexaenoic acid
 62 61  0  0  0  0  0  0  0  0999 V2000
    9.3417   -2.0919    2.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3386   -0.8505    1.6033 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9451   -1.1489    0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9444   -0.6721   -0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9472    0.2940    0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9260    1.5343   -0.7350 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0005    2.0800   -1.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6156    1.7466   -1.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500    0.4819   -1.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1803    0.2625   -0.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3836    1.3791    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9656    1.1331   -0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3578    2.0453   -0.9525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0541    1.7984   -1.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5331    0.5088   -0.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5771    0.4360    0.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0905   -0.8257    0.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5169   -1.0718    0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4617   -1.1936    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8558   -1.4365    0.6720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7862   -0.3454    1.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1927   -0.5830    0.7020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3423   -0.6605   -0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7481   -0.8918   -1.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2663   -2.0302   -1.0898 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5327    0.1260   -1.7174 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8146   -1.8425    3.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3614   -2.4062    2.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8346   -2.9520    1.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4267   -0.5042    1.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7379   -0.0846    2.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5907   -1.8850   -0.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7776   -0.9979   -1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9643   -0.1921    0.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2760    0.5635    1.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9231    2.0698   -0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3086    3.0696   -1.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9645    2.6230   -1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5850    1.6879   -2.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6489   -0.4450   -1.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286   -0.7636   -0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7075    2.3795   -0.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4640    1.3631    1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4645    0.2140    0.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8770    2.9301   -1.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6484    2.6546   -1.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0520    1.7206   -2.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0611   -0.4164   -1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0698    1.3765    0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5164   -1.6864    0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0170   -0.9144    1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7411   -1.1458   -0.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1798   -1.1108    2.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8839   -1.5339   -0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1877   -2.3687    1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7130   -0.2977    2.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4441    0.6602    0.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5940   -1.5207    1.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8694    0.2192    1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7265   -1.4692   -1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0117    0.3028   -1.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0788    0.6791   -1.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 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
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
 23 61  1  0
 26 62  1  0
M  END

HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         0                                  
HETATM    1  C   UNK     0       3.286   8.057   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.286   9.597   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.953  10.367   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.953  11.907   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.619  12.677   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.715  11.907   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.048  12.677   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.382  11.907   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.382  10.367   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.716   9.597   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.716   8.057   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.382   7.287   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.382   5.747   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.048   4.977   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.715   5.747   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.619   4.977   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.953   5.747   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.286   4.977   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       9.955   1.127   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                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

COMPND    HMDB0013025
HETATM    1  C1  UNL     1       9.342  -2.092   2.480  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.339  -0.851   1.603  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.945  -1.149   0.223  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.944  -0.672  -0.428  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.947   0.294   0.063  1.00  0.00           C  
HETATM    6  C6  UNL     1       6.926   1.534  -0.735  1.00  0.00           C  
HETATM    7  C7  UNL     1       6.001   2.080  -1.439  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.616   1.747  -1.767  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.150   0.482  -1.228  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.180   0.262  -0.372  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.384   1.379   0.188  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.966   1.133  -0.215  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.358   2.045  -0.953  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.054   1.798  -1.352  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.533   0.509  -0.819  1.00  0.00           C  
HETATM   16  C16 UNL     1      -2.577   0.436   0.013  1.00  0.00           C  
HETATM   17  C17 UNL     1      -3.090  -0.826   0.570  1.00  0.00           C  
HETATM   18  C18 UNL     1      -4.517  -1.072   0.191  1.00  0.00           C  
HETATM   19  C19 UNL     1      -5.462  -1.194   1.112  1.00  0.00           C  
HETATM   20  C20 UNL     1      -6.856  -1.436   0.672  1.00  0.00           C  
HETATM   21  C21 UNL     1      -7.786  -0.345   1.129  1.00  0.00           C  
HETATM   22  C22 UNL     1      -9.193  -0.583   0.702  1.00  0.00           C  
HETATM   23  C23 UNL     1      -9.342  -0.660  -0.788  1.00  0.00           C  
HETATM   24  C24 UNL     1     -10.748  -0.892  -1.201  1.00  0.00           C  
HETATM   25  O1  UNL     1     -11.266  -2.030  -1.090  1.00  0.00           O  
HETATM   26  O2  UNL     1     -11.533   0.126  -1.717  1.00  0.00           O  
HETATM   27  H1  UNL     1       8.815  -1.842   3.418  1.00  0.00           H  
HETATM   28  H2  UNL     1      10.361  -2.406   2.769  1.00  0.00           H  
HETATM   29  H3  UNL     1       8.835  -2.952   1.992  1.00  0.00           H  
HETATM   30  H4  UNL     1      10.427  -0.504   1.602  1.00  0.00           H  
HETATM   31  H5  UNL     1       8.738  -0.085   2.096  1.00  0.00           H  
HETATM   32  H6  UNL     1       9.591  -1.885  -0.349  1.00  0.00           H  
HETATM   33  H7  UNL     1       7.778  -0.998  -1.476  1.00  0.00           H  
HETATM   34  H8  UNL     1       5.964  -0.192   0.190  1.00  0.00           H  
HETATM   35  H9  UNL     1       7.276   0.563   1.135  1.00  0.00           H  
HETATM   36  H10 UNL     1       7.923   2.070  -0.692  1.00  0.00           H  
HETATM   37  H11 UNL     1       6.309   3.070  -1.945  1.00  0.00           H  
HETATM   38  H12 UNL     1       3.964   2.623  -1.514  1.00  0.00           H  
HETATM   39  H13 UNL     1       4.585   1.688  -2.926  1.00  0.00           H  
HETATM   40  H14 UNL     1       4.649  -0.445  -1.606  1.00  0.00           H  
HETATM   41  H15 UNL     1       2.929  -0.764  -0.043  1.00  0.00           H  
HETATM   42  H16 UNL     1       2.708   2.379  -0.097  1.00  0.00           H  
HETATM   43  H17 UNL     1       2.464   1.363   1.317  1.00  0.00           H  
HETATM   44  H18 UNL     1       0.465   0.214   0.106  1.00  0.00           H  
HETATM   45  H19 UNL     1       0.877   2.930  -1.247  1.00  0.00           H  
HETATM   46  H20 UNL     1      -1.648   2.655  -1.000  1.00  0.00           H  
HETATM   47  H21 UNL     1      -1.052   1.721  -2.467  1.00  0.00           H  
HETATM   48  H22 UNL     1      -1.061  -0.416  -1.081  1.00  0.00           H  
HETATM   49  H23 UNL     1      -3.070   1.377   0.287  1.00  0.00           H  
HETATM   50  H24 UNL     1      -2.516  -1.686   0.119  1.00  0.00           H  
HETATM   51  H25 UNL     1      -3.017  -0.914   1.657  1.00  0.00           H  
HETATM   52  H26 UNL     1      -4.741  -1.146  -0.866  1.00  0.00           H  
HETATM   53  H27 UNL     1      -5.180  -1.111   2.155  1.00  0.00           H  
HETATM   54  H28 UNL     1      -6.884  -1.534  -0.413  1.00  0.00           H  
HETATM   55  H29 UNL     1      -7.188  -2.369   1.199  1.00  0.00           H  
HETATM   56  H30 UNL     1      -7.713  -0.298   2.238  1.00  0.00           H  
HETATM   57  H31 UNL     1      -7.444   0.660   0.777  1.00  0.00           H  
HETATM   58  H32 UNL     1      -9.594  -1.521   1.181  1.00  0.00           H  
HETATM   59  H33 UNL     1      -9.869   0.219   1.077  1.00  0.00           H  
HETATM   60  H34 UNL     1      -8.727  -1.469  -1.233  1.00  0.00           H  
HETATM   61  H35 UNL     1      -9.012   0.303  -1.225  1.00  0.00           H  
HETATM   62  H36 UNL     1     -12.079   0.679  -1.037  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   30   31
CONECT    3    4    4   32
CONECT    4    5   33
CONECT    5    6   34   35
CONECT    6    7    7   36
CONECT    7    8   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   19   52
CONECT   19   20   53
CONECT   20   21   54   55
CONECT   21   22   56   57
CONECT   22   23   58   59
CONECT   23   24   60   61
CONECT   24   25   25   26
CONECT   26   62
END

HMDB0013025
     RDKit          3D
6,9,12,15,18,21-Tetracosahexaenoic acid
 62 61  0  0  0  0  0  0  0  0999 V2000
    9.3417   -2.0919    2.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3386   -0.8505    1.6033 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9451   -1.1489    0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9444   -0.6721   -0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9472    0.2940    0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9260    1.5343   -0.7350 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0005    2.0800   -1.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6156    1.7466   -1.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500    0.4819   -1.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1803    0.2625   -0.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3836    1.3791    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9656    1.1331   -0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3578    2.0453   -0.9525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0541    1.7984   -1.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5331    0.5088   -0.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5771    0.4360    0.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0905   -0.8257    0.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5169   -1.0718    0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4617   -1.1936    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8558   -1.4365    0.6720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7862   -0.3454    1.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1927   -0.5830    0.7020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3423   -0.6605   -0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7481   -0.8918   -1.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2663   -2.0302   -1.0898 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5327    0.1260   -1.7174 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8146   -1.8425    3.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3614   -2.4062    2.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8346   -2.9520    1.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4267   -0.5042    1.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7379   -0.0846    2.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5907   -1.8850   -0.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7776   -0.9979   -1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9643   -0.1921    0.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2760    0.5635    1.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9231    2.0698   -0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3086    3.0696   -1.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9645    2.6230   -1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5850    1.6879   -2.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6489   -0.4450   -1.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286   -0.7636   -0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7075    2.3795   -0.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4640    1.3631    1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4645    0.2140    0.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8770    2.9301   -1.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6484    2.6546   -1.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0520    1.7206   -2.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0611   -0.4164   -1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0698    1.3765    0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5164   -1.6864    0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0170   -0.9144    1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7411   -1.1458   -0.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1798   -1.1108    2.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8839   -1.5339   -0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1877   -2.3687    1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7130   -0.2977    2.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4441    0.6602    0.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5940   -1.5207    1.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8694    0.2192    1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7265   -1.4692   -1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0117    0.3028   -1.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0788    0.6791   -1.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 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
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
 23 61  1  0
 26 62  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6,9,12,15,18,21-Tetracosahexaenoate	Generator
Tetracosa-6,9,12,15,18,21-hexaenoate	HMDB

Chemical Formula

C₂₄H₃₆O₂

Average Molecular Weight

356.55

Monoisotopic Molecular Weight

356.271530399

IUPAC Name

tetracosa-6,9,12,15,18,21-hexaenoic acid

Traditional Name

tetracosa-6,9,12,15,18,21-hexaenoic acid

CAS Registry Number

Not Available

SMILES

CCC=CCC=CCC=CCC=CCC=CCC=CCCCCC(O)=O

InChI Identifier

InChI=1S/C24H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-23H2,1H3,(H,25,26)

InChI Key

YHGJECVSSKXFCJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents

Substituents

Very long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0013025)
Membrane (HMDB: HMDB0013025)

Source

Exogenous

Exogenous (HMDB: HMDB0013025)

Food

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Endogenous (HMDB: HMDB0013025)

Process

Not Available

Role

Not Available

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	7.1e-05 g/L	ALOGPS
logP	7.28	ALOGPS
logP	7.64	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	4.92	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	120.59 m³·mol⁻¹	ChemAxon
Polarizability	44.15 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
DeepCCS	[M+H]+	185.316	30932474
DeepCCS	[M-H]-	182.958	30932474
DeepCCS	[M-2H]-	215.844	30932474
DeepCCS	[M+Na]+	191.409	30932474
AllCCS	[M+H]+	197.1	32859911
AllCCS	[M+H-H2O]+	194.4	32859911
AllCCS	[M+NH4]+	199.6	32859911
AllCCS	[M+Na]+	200.3	32859911
AllCCS	[M-H]-	195.4	32859911
AllCCS	[M+Na-2H]-	197.9	32859911
AllCCS	[M+HCOO]-	200.7	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.	5.12 minutes	32390414
Predicted by Siyang on May 30, 2022	31.5655 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.42 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	44.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3695.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	715.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	306.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	601.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	899.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1495.0 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	716.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	97.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2903.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	993.9 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	2257.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1107.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	661.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	508.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	702.6 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	9.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6,9,12,15,18,21-Tetracosahexaenoic acid	CCC=CCC=CCC=CCC=CCC=CCC=CCCCCC(O)=O	4183.2	Standard polar	33892256
6,9,12,15,18,21-Tetracosahexaenoic acid	CCC=CCC=CCC=CCC=CCC=CCC=CCCCCC(O)=O	2405.4	Standard non polar	33892256
6,9,12,15,18,21-Tetracosahexaenoic acid	CCC=CCC=CCC=CCC=CCC=CCC=CCCCCC(O)=O	2721.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6,9,12,15,18,21-Tetracosahexaenoic acid,1TMS,isomer #1	CCC=CCC=CCC=CCC=CCC=CCC=CCCCCC(=O)O[Si](C)(C)C	2747.9	Semi standard non polar	33892256
6,9,12,15,18,21-Tetracosahexaenoic acid,1TBDMS,isomer #1	CCC=CCC=CCC=CCC=CCC=CCC=CCCCCC(=O)O[Si](C)(C)C(C)(C)C	3004.0	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 - 6,9,12,15,18,21-Tetracosahexaenoic 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 - 6,9,12,15,18,21-Tetracosahexaenoic acid 10V, Positive-QTOF	splash10-000i-0009000000-0aecad3f10eefdf7d1b1	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,9,12,15,18,21-Tetracosahexaenoic acid 20V, Positive-QTOF	splash10-03ds-4559000000-d044187c05f199f03f75	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,9,12,15,18,21-Tetracosahexaenoic acid 40V, Positive-QTOF	splash10-01p2-9673000000-fe0e36efc6429aef7914	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,9,12,15,18,21-Tetracosahexaenoic acid 10V, Negative-QTOF	splash10-0a4i-0009000000-2a2103fe5e22d781b9b9	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,9,12,15,18,21-Tetracosahexaenoic acid 20V, Negative-QTOF	splash10-0bti-0009000000-093b42344e6284ef767d	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,9,12,15,18,21-Tetracosahexaenoic acid 40V, Negative-QTOF	splash10-0a4l-9123000000-94c48fd43abe43b10fe7	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,9,12,15,18,21-Tetracosahexaenoic acid 10V, Negative-QTOF	splash10-0a4i-0009000000-96a0c6d373c7eb750860	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,9,12,15,18,21-Tetracosahexaenoic acid 20V, Negative-QTOF	splash10-0a4r-1009000000-f3cf175eec093aa8f784	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,9,12,15,18,21-Tetracosahexaenoic acid 40V, Negative-QTOF	splash10-052f-9033000000-5d444b34f231862080c2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,9,12,15,18,21-Tetracosahexaenoic acid 10V, Positive-QTOF	splash10-0a4r-1119000000-6b60214ee63c5d7a07ae	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,9,12,15,18,21-Tetracosahexaenoic acid 20V, Positive-QTOF	splash10-05ar-7966000000-0bb0202f87452308f75b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,9,12,15,18,21-Tetracosahexaenoic acid 40V, Positive-QTOF	splash10-053u-9710000000-e8579e42e6d94744c449	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54508254

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

TETHEX3

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Nichols PD, Danaher KT, Koslow JA: Occurrence of high levels of tetracosahexaenoic acid in the jellyfish Aurelia sp. Lipids. 2003 Nov;38(11):1207-10. [PubMed:14733367 ]
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 ]
(). Takagi, T., Kaneniwa, M., and Itabashi, Y. (1986) Fatty Acids in Crinoidea and Ophiuroidea: Occurrence of All-cis-6,9,12,15, 18,21-Tetracosahexaenoic Acid, Lipids 21, 430–433.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 6,9,12,15,18,21-Tetracosahexaenoic acid (HMDB0013025)

MOL for HMDB0013025 (6,9,12,15,18,21-Tetracosahexaenoic acid)

3D MOL for HMDB0013025 (6,9,12,15,18,21-Tetracosahexaenoic acid)

3D SDF for HMDB0013025 (6,9,12,15,18,21-Tetracosahexaenoic acid)

3D-SDF for HMDB0013025 (6,9,12,15,18,21-Tetracosahexaenoic acid)

PDB for HMDB0013025 (6,9,12,15,18,21-Tetracosahexaenoic acid)

3D PDB for HMDB0013025 (6,9,12,15,18,21-Tetracosahexaenoic acid)

SMILES for HMDB0013025 (6,9,12,15,18,21-Tetracosahexaenoic acid)

INCHI for HMDB0013025 (6,9,12,15,18,21-Tetracosahexaenoic acid)

Structure for HMDB0013025 (6,9,12,15,18,21-Tetracosahexaenoic acid)

3D Structure for HMDB0013025 (6,9,12,15,18,21-Tetracosahexaenoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra