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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:40 UTC

Update Date

2022-03-07 02:49:13 UTC

HMDB ID

HMDB0002183

Secondary Accession Numbers

HMDB0062579
HMDB02183
HMDB62579

Metabolite Identification

Common Name

Docosahexaenoic acid

Description

Docosahexaenoic acid (DHA) is an omega-3 essential fatty acid. Chemically, DHA is a carboxylic acid with a 22-carbon chain and six cis- double bonds with the first double bond located at the third carbon from the omega end. DHA is most often found in fish oil. It is a major fatty acid in sperm and brain phospholipids, especially in the retina. Dietary DHA can reduce the level of blood triglycerides in humans, which may reduce the risk of heart disease (Wikipedia ). Docosahexaenoic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.

Structure

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

HMDB0002183
     RDKit          3D
Docosahexaenoic acid
 56 55  0  0  0  0  0  0  0  0999 V2000
    1.7913    1.7482   -0.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2807    1.5735    0.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9767    1.1409   -0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6793    0.0660   -1.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0220   -1.0142   -0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5932   -1.0868    1.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8958   -2.0694    1.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4245   -3.2774    0.9782 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9594   -3.4113    1.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1430   -3.4696    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4686   -3.4112   -1.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9227   -2.4275   -2.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0929   -1.4490   -2.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4792   -1.1538   -0.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9280   -1.3694   -0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8157   -0.4804   -0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4465    0.9216   -0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9014    1.2299    1.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7214    2.2055    1.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2800    3.1040    0.6127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7994    2.9431    0.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4627    3.8036   -0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7891    4.5518   -1.0753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8426    3.7923   -0.4324 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1179    1.4807    0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6720    2.8105   -0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5971    1.1881   -1.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2665    0.8880    1.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6219    2.5957    0.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8541    1.8582   -1.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1137   -0.0335   -2.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8024   -2.0055   -0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1933   -1.1142   -0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9068   -0.2670    1.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6514   -1.9415    2.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8832   -4.2084    1.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230   -3.3690   -0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5862   -3.4605    2.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0746   -3.6318    0.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814   -4.4855   -1.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6116   -3.3957   -1.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727   -2.5095   -3.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2325   -0.7859   -2.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3909    0.0120   -0.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1325   -1.4763    0.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2522   -2.4067   -0.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8632   -0.8004   -0.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1038    1.5190   -0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4154    1.2214   -0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5168    0.5957    2.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0327    2.3893    2.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0339    4.1554    0.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9671    2.9685   -0.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0001    1.8637    0.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1198    3.2062    1.6942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3180    4.6785   -0.3525 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  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END

LMFA01030185
  Mrv1652303312018252D          

 24 23  0  0  0  0            999 V2000
   18.5234    5.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2379    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9524    5.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6669    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3815    5.2475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6669    6.4850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6984    5.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9840    5.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2695    5.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4445    5.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7301    5.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0156    5.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1906    5.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4761    5.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7617    5.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9367    5.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2223    5.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5078    5.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6828    5.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9684    5.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2539    5.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4289    5.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7144    5.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0000    5.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  4  6  2  0  0  0  0
  1  7  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 12 13  2  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 15 16  2  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  2  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 21 22  2  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002183

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-

> <INCHI_KEY>
MBMBGCFOFBJSGT-KUBAVDMBSA-N

> <FORMULA>
C22H32O2

> <MOLECULAR_WEIGHT>
328.4883

> <EXACT_MASS>
328.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.626277984771455

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid

> <ALOGPS_LOGP>
6.83

> <JCHEM_LOGP>
6.752464827666667

> <ALOGPS_LOGS>
-6.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.8854984143453795

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
111.3892

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.86e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
docosahexaenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002183
     RDKit          3D
Docosahexaenoic acid
 56 55  0  0  0  0  0  0  0  0999 V2000
    1.7913    1.7482   -0.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2807    1.5735    0.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9767    1.1409   -0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6793    0.0660   -1.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0220   -1.0142   -0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5932   -1.0868    1.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8958   -2.0694    1.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4245   -3.2774    0.9782 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9594   -3.4113    1.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1430   -3.4696    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4686   -3.4112   -1.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9227   -2.4275   -2.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0929   -1.4490   -2.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4792   -1.1538   -0.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9280   -1.3694   -0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8157   -0.4804   -0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4465    0.9216   -0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9014    1.2299    1.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7214    2.2055    1.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2800    3.1040    0.6127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7994    2.9431    0.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4627    3.8036   -0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7891    4.5518   -1.0753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8426    3.7923   -0.4324 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1179    1.4807    0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6720    2.8105   -0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5971    1.1881   -1.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2665    0.8880    1.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6219    2.5957    0.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8541    1.8582   -1.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1137   -0.0335   -2.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8024   -2.0055   -0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1933   -1.1142   -0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9068   -0.2670    1.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6514   -1.9415    2.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8832   -4.2084    1.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230   -3.3690   -0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5862   -3.4605    2.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0746   -3.6318    0.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814   -4.4855   -1.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6116   -3.3957   -1.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727   -2.5095   -3.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2325   -0.7859   -2.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3909    0.0120   -0.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1325   -1.4763    0.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2522   -2.4067   -0.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8632   -0.8004   -0.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1038    1.5190   -0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4154    1.2214   -0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5168    0.5957    2.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0327    2.3893    2.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0339    4.1554    0.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9671    2.9685   -0.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0001    1.8637    0.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1198    3.2062    1.6942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3180    4.6785   -0.3525 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  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END

HEADER    PROTEIN                                 31-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LMFA01030185                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAR-20         0                                  
HETATM    1  C   UNK     0      34.577   9.795   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      35.911  10.566   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      37.244   9.795   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      38.578  10.566   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      39.912   9.795   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      38.578  12.105   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      33.037   9.795   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.703  10.565   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.370   9.795   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.830   9.795   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      27.496  10.565   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.162   9.795   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.622   9.795   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.289  10.565   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.955   9.795   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.415   9.795   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.082  10.565   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.748   9.795   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.208   9.795   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.874  10.565   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.541   9.795   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.001   9.795   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.667  10.565   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.333   9.795   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1    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                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0002183
HETATM    1  C1  UNL     1       1.791   1.748  -0.179  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.281   1.573   0.223  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.977   1.141  -0.979  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.679   0.066  -1.114  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.022  -1.014  -0.224  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.593  -1.087   1.143  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.896  -2.069   1.671  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.425  -3.277   0.978  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.959  -3.411   1.101  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.143  -3.470   0.077  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.469  -3.411  -1.319  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.923  -2.428  -2.235  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.093  -1.449  -2.054  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.479  -1.154  -0.726  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.928  -1.369  -0.671  1.00  0.00           C  
HETATM   16  C16 UNL     1      -2.816  -0.480  -0.369  1.00  0.00           C  
HETATM   17  C17 UNL     1      -2.447   0.922  -0.027  1.00  0.00           C  
HETATM   18  C18 UNL     1      -2.901   1.230   1.353  1.00  0.00           C  
HETATM   19  C19 UNL     1      -3.721   2.205   1.628  1.00  0.00           C  
HETATM   20  C20 UNL     1      -4.280   3.104   0.613  1.00  0.00           C  
HETATM   21  C21 UNL     1      -5.799   2.943   0.656  1.00  0.00           C  
HETATM   22  C22 UNL     1      -6.463   3.804  -0.327  1.00  0.00           C  
HETATM   23  O1  UNL     1      -5.789   4.552  -1.075  1.00  0.00           O  
HETATM   24  O2  UNL     1      -7.843   3.792  -0.432  1.00  0.00           O  
HETATM   25  H1  UNL     1       1.118   1.481   0.636  1.00  0.00           H  
HETATM   26  H2  UNL     1       1.672   2.811  -0.433  1.00  0.00           H  
HETATM   27  H3  UNL     1       1.597   1.188  -1.131  1.00  0.00           H  
HETATM   28  H4  UNL     1       3.266   0.888   1.057  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.622   2.596   0.533  1.00  0.00           H  
HETATM   30  H6  UNL     1       3.854   1.858  -1.849  1.00  0.00           H  
HETATM   31  H7  UNL     1       5.114  -0.033  -2.171  1.00  0.00           H  
HETATM   32  H8  UNL     1       4.802  -2.006  -0.743  1.00  0.00           H  
HETATM   33  H9  UNL     1       6.193  -1.114  -0.174  1.00  0.00           H  
HETATM   34  H10 UNL     1       4.907  -0.267   1.874  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.651  -1.941   2.767  1.00  0.00           H  
HETATM   36  H12 UNL     1       3.883  -4.208   1.533  1.00  0.00           H  
HETATM   37  H13 UNL     1       3.823  -3.369  -0.031  1.00  0.00           H  
HETATM   38  H14 UNL     1       1.586  -3.461   2.143  1.00  0.00           H  
HETATM   39  H15 UNL     1       0.075  -3.632   0.381  1.00  0.00           H  
HETATM   40  H16 UNL     1       1.281  -4.485  -1.769  1.00  0.00           H  
HETATM   41  H17 UNL     1       2.612  -3.396  -1.475  1.00  0.00           H  
HETATM   42  H18 UNL     1       1.273  -2.509  -3.320  1.00  0.00           H  
HETATM   43  H19 UNL     1      -0.232  -0.786  -2.868  1.00  0.00           H  
HETATM   44  H20 UNL     1      -0.391   0.012  -0.603  1.00  0.00           H  
HETATM   45  H21 UNL     1       0.132  -1.476   0.080  1.00  0.00           H  
HETATM   46  H22 UNL     1      -2.252  -2.407  -0.920  1.00  0.00           H  
HETATM   47  H23 UNL     1      -3.863  -0.800  -0.374  1.00  0.00           H  
HETATM   48  H24 UNL     1      -3.104   1.519  -0.752  1.00  0.00           H  
HETATM   49  H25 UNL     1      -1.415   1.221  -0.172  1.00  0.00           H  
HETATM   50  H26 UNL     1      -2.517   0.596   2.154  1.00  0.00           H  
HETATM   51  H27 UNL     1      -4.033   2.389   2.691  1.00  0.00           H  
HETATM   52  H28 UNL     1      -4.034   4.155   0.994  1.00  0.00           H  
HETATM   53  H29 UNL     1      -3.967   2.969  -0.388  1.00  0.00           H  
HETATM   54  H30 UNL     1      -6.000   1.864   0.503  1.00  0.00           H  
HETATM   55  H31 UNL     1      -6.120   3.206   1.694  1.00  0.00           H  
HETATM   56  H32 UNL     1      -8.318   4.679  -0.352  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4    4   30
CONECT    4    5   31
CONECT    5    6   32   33
CONECT    6    7    7   34
CONECT    7    8   35
CONECT    8    9   36   37
CONECT    9   10   10   38
CONECT   10   11   39
CONECT   11   12   40   41
CONECT   12   13   13   42
CONECT   13   14   43
CONECT   14   15   44   45
CONECT   15   16   16   46
CONECT   16   17   47
CONECT   17   18   48   49
CONECT   18   19   19   50
CONECT   19   20   51
CONECT   20   21   52   53
CONECT   21   22   54   55
CONECT   22   23   23   24
CONECT   24   56
END

HMDB0002183
     RDKit          3D
Docosahexaenoic acid
 56 55  0  0  0  0  0  0  0  0999 V2000
    1.7913    1.7482   -0.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2807    1.5735    0.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9767    1.1409   -0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6793    0.0660   -1.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0220   -1.0142   -0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5932   -1.0868    1.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8958   -2.0694    1.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4245   -3.2774    0.9782 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9594   -3.4113    1.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1430   -3.4696    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4686   -3.4112   -1.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9227   -2.4275   -2.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0929   -1.4490   -2.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4792   -1.1538   -0.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9280   -1.3694   -0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8157   -0.4804   -0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4465    0.9216   -0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9014    1.2299    1.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7214    2.2055    1.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2800    3.1040    0.6127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7994    2.9431    0.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4627    3.8036   -0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7891    4.5518   -1.0753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8426    3.7923   -0.4324 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1179    1.4807    0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6720    2.8105   -0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5971    1.1881   -1.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2665    0.8880    1.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6219    2.5957    0.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8541    1.8582   -1.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1137   -0.0335   -2.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8024   -2.0055   -0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1933   -1.1142   -0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9068   -0.2670    1.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6514   -1.9415    2.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8832   -4.2084    1.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230   -3.3690   -0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5862   -3.4605    2.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0746   -3.6318    0.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814   -4.4855   -1.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6116   -3.3957   -1.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727   -2.5095   -3.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2325   -0.7859   -2.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3909    0.0120   -0.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1325   -1.4763    0.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2522   -2.4067   -0.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8632   -0.8004   -0.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1038    1.5190   -0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4154    1.2214   -0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5168    0.5957    2.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0327    2.3893    2.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0339    4.1554    0.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9671    2.9685   -0.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0001    1.8637    0.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1198    3.2062    1.6942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3180    4.6785   -0.3525 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  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid	ChEBI
22:6(N-3)	ChEBI
22:6-4, 7,10,13,16,19	ChEBI
4,7,10,13,16,19-Docosahexaenoic acid	ChEBI
all-cis-4,7,10,13,16,19-Docosahexaenoic acid	ChEBI
all-cis-DHA	ChEBI
Cervonic acid	ChEBI
DHA	ChEBI
Doconexent	ChEBI
DOCOSA-4,7,10,13,16,19-hexaenoIC ACID	ChEBI
Docosahexaenoate	Kegg
4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoic acid	Kegg
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoic acid	Kegg
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoate	Generator
4,7,10,13,16,19-Docosahexaenoate	Generator
all-cis-4,7,10,13,16,19-Docosahexaenoate	Generator
Cervonate	Generator
DOCOSA-4,7,10,13,16,19-hexaenoate	Generator
4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoate	Generator
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoate	Generator
all-Z-Docosahexaenoate	HMDB
all-Z-Docosahexaenoic acid	HMDB
cis-4,7,10,13,16,19-Docosahexanoate	HMDB
cis-4,7,10,13,16,19-Docosahexanoic acid	HMDB
Doconexento	HMDB
Doconexentum	HMDB
Doxonexent	HMDB
Acids, docosahexaenoic	HMDB
Acids, docosahexenoic	HMDB
Docosahexaenoic acid, 4,7,10,13,16,19-(all-Z-isomer)	HMDB
Docosahexaenoic acid (all-Z isomer)	HMDB
Docosahexaenoic acid, 4,7,10,13,16,19-isomer	HMDB
Efalex	HMDB
(4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-Docosahexaenoic acid	HMDB
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexenoic acid	HMDB
(all-Z)-4,7,10,13,16,19-Docosahexaenoic acid	HMDB
4-cis,7-cis,10-cis,13-cis,16-cis,19-cis-Docosahexaenoic acid	HMDB
FA(22:6(4Z,7Z,10Z,13Z,16Z,19Z))	HMDB
FA(22:6n3)	HMDB
delta4,7,10,13,16,19-Docosahexaenoic acid	HMDB
Δ4,7,10,13,16,19-docosahexaenoic acid	HMDB
Docosahexaenoic acid	HMDB
Choline docosahexaenoate	HMDB
Choline docosahexaenoic acid	HMDB
Docosahexaenoylcholine	HMDB

Chemical Formula

C₂₂H₃₂O₂

Average Molecular Weight

328.4883

Monoisotopic Molecular Weight

328.240230268

IUPAC Name

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid

Traditional Name

docosahexaenoic acid

CAS Registry Number

6217-54-5

SMILES

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

InChI Identifier

InChI=1S/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-

InChI Key

MBMBGCFOFBJSGT-KUBAVDMBSA-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

omega-3 fatty acid (CHEBI:28125 )
docosahexaenoic acid (CHEBI:28125 )
Unsaturated fatty acids (C06429 )
Docosanoids (C06429 )
Polyunsaturated fatty acids (C06429 )
Unsaturated fatty acids (LMFA01030185 )

Ontology

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]-	Baker	191.122	30932474
[M+H]+	Baker	184.62	30932474
[M-H]-	Not Available	191.122	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001852
[M+H]+	Not Available	184.62	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001852

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00019 g/L	ALOGPS
logP	6.83	ALOGPS
logP	6.75	ChemAxon
logS	-6.2	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	111.39 m³·mol⁻¹	ChemAxon
Polarizability	38.63 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]+	192.614	31661259
DarkChem	[M-H]-	191.921	31661259
DeepCCS	[M+H]+	186.932	30932474
DeepCCS	[M-H]-	184.574	30932474
DeepCCS	[M-2H]-	217.46	30932474
DeepCCS	[M+Na]+	193.026	30932474
AllCCS	[M+H]+	188.6	32859911
AllCCS	[M+H-H2O]+	185.6	32859911
AllCCS	[M+NH4]+	191.3	32859911
AllCCS	[M+Na]+	192.0	32859911
AllCCS	[M-H]-	185.7	32859911
AllCCS	[M+Na-2H]-	187.5	32859911
AllCCS	[M+HCOO]-	189.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Docosahexaenoic acid	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O	4132.5	Standard polar	33892256
Docosahexaenoic acid	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O	2242.9	Standard non polar	33892256
Docosahexaenoic acid	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O	2521.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Docosahexaenoic acid,1TMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C	2562.9	Semi standard non polar	33892256
Docosahexaenoic acid,1TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C	2809.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Docosahexaenoic acid GC-MS (1 TMS)	splash10-004l-9800000000-86f34228f9e92b6da2c6	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Docosahexaenoic acid GC-MS (Non-derivatized)	splash10-004l-9800000000-86f34228f9e92b6da2c6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Docosahexaenoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0690-5590000000-145821d84e425eec8f98	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Docosahexaenoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0079-9363000000-db2668be2bbd1dbdd562	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Docosahexaenoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-002f-9400000000-60bd7bfd4de9015476c7	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosahexaenoic acid LC-ESI-IT , negative-QTOF	splash10-001i-0190000000-e6566b5aff7cefa4ae5d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosahexaenoic acid LC-ESI-QQ , negative-QTOF	splash10-004i-0069000000-c76c91e0abd1895adb8b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosahexaenoic acid LC-ESI-QQ , negative-QTOF	splash10-001r-0069000000-a25e6a700612620a1217	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosahexaenoic acid 35V, Negative-QTOF	splash10-0ab9-9321000000-6b36fbd84ed730000eac	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosahexaenoic acid 35V, Negative-QTOF	splash10-0a4i-9642000000-5ecff42b9082b57b5be6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosahexaenoic acid 35V, Negative-QTOF	splash10-004i-0389000000-737691a3fc2f16b3c59e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosahexaenoic acid 40V, Positive-QTOF	splash10-00l6-9510000000-8e81381f5f447b18e9fc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosahexaenoic acid 10V, Positive-QTOF	splash10-004i-0009000000-071caf7af6bdab525160	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosahexaenoic acid 20V, Positive-QTOF	splash10-004i-1669000000-4e72cfd5cc68b32bd371	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosahexaenoic acid 20V, Negative-QTOF	splash10-0059-1179000000-289993a223b524e7c74f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosahexaenoic acid 10V, Negative-QTOF	splash10-004i-0019000000-aa9263466508c9f2e65c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosahexaenoic acid 30V, Negative-QTOF	splash10-004i-7389000000-4e6afa18acb803f01d23	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosahexaenoic acid 35V, Negative-QTOF	splash10-0a4i-9442000000-c452e1856fb3038c7f1e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosahexaenoic acid 20V, Positive-QTOF	splash10-004i-1569000000-4e72cfd5cc68b32bd371	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoic acid 10V, Positive-QTOF	splash10-01t9-0139000000-7f2351e9d6b367bd3e6d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoic acid 20V, Positive-QTOF	splash10-001i-3592000000-10365ee2a8e305e24bd4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoic acid 40V, Positive-QTOF	splash10-0ktf-8960000000-6382301474f6f5630982	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoic acid 10V, Negative-QTOF	splash10-004i-0019000000-f498ba345a6e0d89ae44	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoic acid 20V, Negative-QTOF	splash10-0059-1069000000-be6f83d34620dceb650e	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoic acid 40V, Negative-QTOF	splash10-0a4l-9130000000-abfb63ab3950fe4edf48	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoic acid 10V, Positive-QTOF	splash10-03fr-1439000000-c5fd83b4d4f8531d17e2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoic acid 20V, Positive-QTOF	splash10-01q9-3922000000-a59c9fe862e58a93dd03	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoic acid 40V, Positive-QTOF	splash10-05o3-7900000000-c8cfc5620efa939690bb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoic acid 10V, Negative-QTOF	splash10-004i-0009000000-abcf527af18f1147a0aa	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoic acid 20V, Negative-QTOF	splash10-056r-1119000000-fbe7758a1c75272194e2	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Adipose Tissue
Brain
Epidermis
Erythrocyte
Fibroblasts
Intestine
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Prostate
Retina
Skeletal Muscle
Testis

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	94.2 +/- 31.3 uM	Adult (>18 years old)	Both	Normal	18633173	details
Blood	Detected and Quantified	4.66 +/- 3.3 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	90.9 +/- 21.6 uM	Adult (>18 years old)	Male	Normal	18633173	details
Blood	Detected and Quantified	98.7 +/- 41.0 uM	Adult (>18 years old)	Female	Normal	18633173	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24740205	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24740205	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24801555	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected and Quantified	2.3 +/- 1.2 uM	Adult (>18 years old)	Both	Normal	2361977	details
Blood	Detected and Quantified	0.9 +/- 0.3 uM	Adult (>18 years old)	Both	Normal	2361977	details
Blood	Detected and Quantified	1.777 +/- 0.796 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	0.990 +/- 0.009 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	128.5 +/- 46.1 uM	Adult (>18 years old)	Not Specified	Normal	27329611	details
Blood	Detected and Quantified	103.504 +/- 30.442 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	100.460 +/- 24.354 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	66.973 +/- 21.310 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	0.00347 uM	Adult (>18 years old)	Not Specified	Normal	11593343	details
Blood	Detected and Quantified	0.00391 uM	Adult (>18 years old)	Not Specified	Normal	11593343	details
Blood	Detected and Quantified	0.00414 uM	Adult (>18 years old)	Not Specified	Normal	11593343	details
Blood	Detected and Quantified	0.00461 uM	Adult (>18 years old)	Not Specified	Normal	11593343	details
Blood	Detected and Quantified	60.885 +/- 12.177 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	154.252 +/- 47.155 uM	Adult (>18 years old)	Both	Normal	17313719	details
Blood	Detected and Quantified	165.607 +/- 68.496 uM	Adult (>18 years old)	Both	Normal	21185973	details
Blood	Detected and Quantified	189.352 +/- 70.0177 uM	Adult (>18 years old)	Both	Normal	21185973	details
Blood	Detected and Quantified	255.260 +/- 75.162 uM	Adult (>18 years old)	Female	Normal	9368807	details
Blood	Detected and Quantified	420 +/- 110 uM	Adult (>18 years old)	Male	Normal	14608088	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.15 +/- 0.015 uM	Adult (>18 years old)	Both	Normal	12967724	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected and Quantified	5.5 +/- 6.3 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	14643447	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	64.7 +/- 39.2 uM	Adult (>18 years old)	Both	Hypertension	18633173	details
Blood	Detected and Quantified	56.6 +/- 36.7 uM	Adult (>18 years old)	Male	Essential hypertension	18633173	details
Blood	Detected and Quantified	83.0 +/- 39.0 uM	Adult (>18 years old)	Female	Essential hypertension	18633173	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Blood	Detected and Quantified	20.66 uM	Newborn (0-30 days old)	Female	Peroxisomal biogenesis disorder	9818927	details
Blood	Detected and Quantified	122.36 uM	Infant (0-1 year old)	Male	Peroxisomal biogenesis disorder	9818927	details
Blood	Detected and Quantified	135.43 uM	Newborn (0-30 days old)	Female	Rhizomelic chondrodysplasia punctata	9818927	details
Blood	Detected and Quantified	144.700-160.300 uM	Children (1-13 years old)	Female	Peroxisomal biogenesis disorder	9818927	details
Blood	Detected and Quantified	64.3 +/- 28.5 uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	27329611	details
Blood	Detected and Quantified	146.733 +/- 61.798 uM	Adult (>18 years old)	Both	Depression	21185973	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.43 +/- 0.3 uM	Adult (>18 years old)	Both	Stroke	12967724	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Not Specified	Premature neonates	23210743	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected and Quantified	4.4 +/- 9.4 umol/mmol creatinine	Adult (>18 years old)	Both	Thyroid cancer	14643447	details

Associated Disorders and Diseases

Disease References

Hypertension
Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32. doi: 10.1291/hypres.31.623. [PubMed:18633173 ]
Essential hypertension
Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32. doi: 10.1291/hypres.31.623. [PubMed:18633173 ]
Major depressive disorder
Sublette ME, Segal-Isaacson CJ, Cooper TB, Fekri S, Vanegas N, Galfalvy HC, Oquendo MA, Mann JJ: Validation of a food frequency questionnaire to assess intake of n-3 polyunsaturated fatty acids in subjects with and without major depressive disorder. J Am Diet Assoc. 2011 Jan;111(1):117-123.e1-2. doi: 10.1016/j.jada.2010.10.007. [PubMed:21185973 ]
Rhizomelic chondrodysplasia punctata
Baumgartner MR, Poll-The BT, Verhoeven NM, Jakobs C, Espeel M, Roels F, Rabier D, Levade T, Rolland MO, Martinez M, Wanders RJ, Saudubray JM: Clinical approach to inherited peroxisomal disorders: a series of 27 patients. Ann Neurol. 1998 Nov;44(5):720-30. [PubMed:9818927 ]
Isovaleric acidemia
Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Stroke
Pilitsis JG, Coplin WM, O'Regan MH, Wellwood JM, Diaz FG, Fairfax MR, Michael DB, Phillis JW: Measurement of free fatty acids in cerebrospinal fluid from patients with hemorrhagic and ischemic stroke. Brain Res. 2003 Sep 26;985(2):198-201. [PubMed:12967724 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Thyroid cancer
Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9. [PubMed:14643447 ]

Associated OMIM IDs

145500 (Hypertension)
608516 (Major depressive disorder)
215100 (Rhizomelic chondrodysplasia punctata)
243500 (Isovaleric acidemia)
601367 (Stroke)
114500 (Colorectal cancer)

External Links

DrugBank ID

DB03756

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003003

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

28125

Food Biomarker Ontology

Not Available

VMH ID

CRVNC

MarkerDB ID

MDB00000383

Good Scents ID

Not Available

References

Synthesis Reference

Wright, Stephen W.; Kuo, Elaine Y.; Corey, E. J. An effective process for the isolation of Docosahexaenoic acid in quantity from cod liver oil. Journal of Organic Chemistry (1987), 52(19), 4399-4401.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Woodman RJ, Mori TA, Burke V, Puddey IB, Barden A, Watts GF, Beilin LJ: Effects of purified eicosapentaenoic acid and docosahexaenoic acid on platelet, fibrinolytic and vascular function in hypertensive type 2 diabetic patients. Atherosclerosis. 2003 Jan;166(1):85-93. [PubMed:12482554 ]
Watanabe A, Saito S, Tsuchida T, Higuchi K, Okita M: Low plasma levels of docosahexaenoic acid in patients with liver cirrhosis and its correction with a polyunsaturated fatty acid-enriched soft oil capsule. Nutrition. 1999 Apr;15(4):284-8. [PubMed:10319360 ]
Sanders TA: Polyunsaturated fatty acids in the food chain in Europe. Am J Clin Nutr. 2000 Jan;71(1 Suppl):176S-8S. [PubMed:10617968 ]
Gomez de Segura IA, Valderrabano S, Vazquez I, Vallejo-Cremades MT, Gomez-Garcia L, Sanchez M, de Miguel E: Protective effects of dietary enrichment with docosahexaenoic acid plus protein in 5-fluorouracil-induced intestinal injury in the rat. Eur J Gastroenterol Hepatol. 2004 May;16(5):479-85. [PubMed:15097041 ]
Shingu T, Karanian JW, Kim HY, Yergey JA, Salem N Jr: Discovery of novel brain lipoxygenase products formed from docosahexaenoic acid (22:6w3). Adv Alcohol Subst Abuse. 1988;7(3-4):235-40. [PubMed:2975919 ]
Hong S, Tjonahen E, Morgan EL, Lu Y, Serhan CN, Rowley AF: Rainbow trout (Oncorhynchus mykiss) brain cells biosynthesize novel docosahexaenoic acid-derived resolvins and protectins-Mediator lipidomic analysis. Prostaglandins Other Lipid Mediat. 2005 Dec;78(1-4):107-16. Epub 2005 Jun 13. [PubMed:16303609 ]
Hibbeln JR, Bissette G, Umhau JC, George DT: Omega-3 status and cerebrospinal fluid corticotrophin releasing hormone in perpetrators of domestic violence. Biol Psychiatry. 2004 Dec 1;56(11):895-7. [PubMed:15576068 ]
Jorgensen MH, Hernell O, Hughes E, Michaelsen KF: Is there a relation between docosahexaenoic acid concentration in mothers' milk and visual development in term infants? J Pediatr Gastroenterol Nutr. 2001 Mar;32(3):293-6. [PubMed:11345178 ]
Crabtree JT, Gordon MJ, Campbell FM, Dutta-Roy AK: Differential distribution and metabolism of arachidonic acid and docosahexaenoic acid by human placental choriocarcinoma (BeWo) cells. Mol Cell Biochem. 1998 Aug;185(1-2):191-8. [PubMed:9746226 ]
Gordon N: Nutrition and cognitive function. Brain Dev. 1997 Apr;19(3):165-70. [PubMed:9134186 ]
Martinez M: Severe deficiency of docosahexaenoic acid in peroxisomal disorders: a defect of delta 4 desaturation? Neurology. 1990 Aug;40(8):1292-8. [PubMed:2143272 ]
Bohles H, Arndt S, Ohlenschlager U, Beeg T, Gebhardt B, Sewell AC: Maternal plasma homocysteine, placenta status and docosahexaenoic acid concentration in erythrocyte phospholipids of the newborn. Eur J Pediatr. 1999 Mar;158(3):243-6. [PubMed:10094448 ]
Crawford MA, Bloom M, Broadhurst CL, Schmidt WF, Cunnane SC, Galli C, Gehbremeskel K, Linseisen F, Lloyd-Smith J, Parkington J: Evidence for the unique function of docosahexaenoic acid during the evolution of the modern hominid brain. Lipids. 1999;34 Suppl:S39-47. [PubMed:10419087 ]
Andersson L, Sternby B, Nilsson A: Hydrolysis of phosphatidylethanolamine by human pancreatic phospholipase A2. Effect of bile salts. Scand J Gastroenterol. 1994 Feb;29(2):182-7. [PubMed:8171289 ]
Brossard N, Croset M, Normand S, Pousin J, Lecerf J, Laville M, Tayot JL, Lagarde M: Human plasma albumin transports [13C]docosahexaenoic acid in two lipid forms to blood cells. J Lipid Res. 1997 Aug;38(8):1571-82. [PubMed:9300779 ]
Berry CB, Hayes D, Murphy A, Wiessner M, Rauen T, McBean GJ: Differential modulation of the glutamate transporters GLT1, GLAST and EAAC1 by docosahexaenoic acid. Brain Res. 2005 Mar 10;1037(1-2):123-33. [PubMed:15777760 ]
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 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Cytosolic acyl coenzyme A thioester hydrolase

General function:: Lipid transport and metabolism
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May play an important physiological function in brain. May play a regulatory role by modulating the cellular levels of fatty acyl-CoA ligands for certain transcription factors as well as the substrates for fatty acid metabolizing enzymes, contributing to lipid homeostasis. Has broad specificity, active towards fatty acyl-CoAs with chain-lengths of C8-C18. Has a maximal activity toward palmitoyl-CoA.
Gene Name:: ACOT7
Uniprot ID:: O00154
Molecular weight:: 40454.945

Reactions

Cervonyl coenzyme A + Water → Coenzyme A + Docosahexaenoic acid	details

Enzyme Details

2. Acyl-coenzyme A thioesterase 2, mitochondrial

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Displays high levels of activity on medium- and long chain acyl CoAs.
Gene Name:: ACOT2
Uniprot ID:: P49753
Molecular weight:: 53218.02

Reactions

Cervonyl coenzyme A + Water → Coenzyme A + Docosahexaenoic acid	details

Enzyme Details

3. Acyl-coenzyme A thioesterase 4

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH (By similarity). Succinyl-CoA thioesterase that also hydrolyzes long chain saturated and unsaturated monocarboxylic acyl-CoAs.
Gene Name:: ACOT4
Uniprot ID:: Q8N9L9
Molecular weight:: 46326.09

Reactions

Cervonyl coenzyme A + Water → Coenzyme A + Docosahexaenoic acid	details

Enzyme Details

4. Cytochrome P450 2U1

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the hydroxylation of arachidonic acid, docosahexaenoic acid and other long chain fatty acids. May modulate the arachidonic acid signaling pathway and play a role in other fatty acid signaling processes.
Gene Name:: CYP2U1
Uniprot ID:: Q7Z449
Molecular weight:: 61986.525

Enzyme Details

5. Acyl-coenzyme A thioesterase 1

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Active towards fatty acyl-CoA with chain-lengths of C12-C16 (By similarity).
Gene Name:: ACOT1
Uniprot ID:: Q86TX2
Molecular weight:: 46276.96

Reactions

Cervonyl coenzyme A + Water → Coenzyme A + Docosahexaenoic acid	details

Showing metabocard for Docosahexaenoic acid (HMDB0002183)

MOL for HMDB0002183 (Docosahexaenoic acid)

3D MOL for HMDB0002183 (Docosahexaenoic acid)

3D SDF for HMDB0002183 (Docosahexaenoic acid)

3D-SDF for HMDB0002183 (Docosahexaenoic acid)

PDB for HMDB0002183 (Docosahexaenoic acid)

3D PDB for HMDB0002183 (Docosahexaenoic acid)

SMILES for HMDB0002183 (Docosahexaenoic acid)

INCHI for HMDB0002183 (Docosahexaenoic acid)

Structure for HMDB0002183 (Docosahexaenoic acid)

3D Structure for HMDB0002183 (Docosahexaenoic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions