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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (16) Show 16 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:31 UTC

Update Date

2020-11-09 23:16:22 UTC

HMDB ID

HMDB0001999

Secondary Accession Numbers

HMDB01999

Metabolite Identification

Common Name

Eicosapentaenoic acid

Description

Eicosapentaenoic acid (EPA or also icosapentaenoic acid) is an important polyunsaturated fatty acid found in fish oils. It serves as the precursor for the prostaglandin-3 and thromboxane-3 families. A diet rich in eicosapentaenoic acid lowers serum lipid concentration, reduces incidence of cardiovascular disorders, prevents platelet aggregation, and inhibits arachidonic acid conversion into the thromboxane-2 and prostaglandin-2 families. Eicosapentaenoic acid is an omega-3 fatty acid. In physiological literature, it is given the name 20:5(n-3). Its systematic chemical name is all-cis-5,8,11,14,17-icosapentaenoic acid. It also has the trivial name timnodonic acid. Chemically, EPA is a carboxylic acid with a 20-carbon chain and five cis double bonds; the first double bond is located at the third carbon from the omega end. Because of the presence of double bonds, EPS is a polyunsaturated fatty acid. Metabolically it acts as a precursor for prostaglandin-3 (which inhibits platelet aggregation), thromboxane-3, and leukotriene-5 groups. It is found in fish oils of cod liver, herring, mackerel, salmon, menhaden, and sardine. It is also found in human breast milk (Wikipedia ).

Structure

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

HMDB0001999
     RDKit          3D
Eicosapentaenoic acid
 52 51  0  0  0  0  0  0  0  0999 V2000
   -8.2536   -1.9837   -0.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5264   -1.0591    0.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0615    0.0941   -0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8148    0.4167   -0.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7111   -0.3325    0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7921   -0.7899   -0.8515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5453   -0.4088   -0.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9784    0.5012    0.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4828    1.7538   -0.4694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2476    2.0973   -0.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8093    1.3804    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492    1.0367   -0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0926    1.4612   -0.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    2.3170    0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6126    1.8924    1.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1980    0.7745    1.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0086   -0.4602    0.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3603   -0.8164    0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3275   -2.1319   -0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3895   -2.2120   -1.5698 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1907   -3.3712   -2.0784 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7082   -1.1503   -2.1054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5558   -2.7782   -0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0566   -2.5265    0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5770   -1.4240   -1.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8121   -1.6214    1.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3833   -0.7063    1.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8430    0.7165   -0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5643    1.2965   -1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2653    0.1713    1.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0792   -1.3188    0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2061   -1.4686   -1.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8727   -0.7651   -1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0953   -0.1031    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5867    0.7128    1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1605    2.3753   -1.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0738    3.0307   -0.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5121    0.5376    1.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1711    2.1403    1.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5448    0.3960   -1.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7769    1.1672   -1.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7861    2.9386    1.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1165    3.2045   -0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9409    2.7236    2.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9819    0.7151    2.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8660   -1.3310    1.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2562   -0.5213    0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6256   -0.0252   -0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1445   -0.8106    1.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929   -2.9075    0.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3689   -2.4607   -0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1775   -0.3675   -2.5760 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  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 22 52  1  0
M  END

 
  Mrv0541 05281313312D          
 
 22 21  0  0  0  0            999 V2000
   12.8416  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6781  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0886  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3892  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3775  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1003  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5409  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9369  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8299  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6898  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0769  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4009  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3658  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2375  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6547  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9486  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9018  -11.3357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6547  -10.0808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7015  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5381  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2492  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9603  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001999

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-

> <INCHI_KEY>
JAZBEHYOTPTENJ-JLNKQSITSA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.451

> <EXACT_MASS>
302.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
35.92931841565799

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid

> <ALOGPS_LOGP>
6.53

> <JCHEM_LOGP>
6.225249154333334

> <ALOGPS_LOGS>
-6.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771840522258

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
101.07059999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.89e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
eicosapentaenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001999
     RDKit          3D
Eicosapentaenoic acid
 52 51  0  0  0  0  0  0  0  0999 V2000
   -8.2536   -1.9837   -0.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5264   -1.0591    0.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0615    0.0941   -0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8148    0.4167   -0.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7111   -0.3325    0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7921   -0.7899   -0.8515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5453   -0.4088   -0.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9784    0.5012    0.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4828    1.7538   -0.4694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2476    2.0973   -0.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8093    1.3804    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492    1.0367   -0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0926    1.4612   -0.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    2.3170    0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6126    1.8924    1.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1980    0.7745    1.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0086   -0.4602    0.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3603   -0.8164    0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3275   -2.1319   -0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3895   -2.2120   -1.5698 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1907   -3.3712   -2.0784 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7082   -1.1503   -2.1054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5558   -2.7782   -0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0566   -2.5265    0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5770   -1.4240   -1.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8121   -1.6214    1.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3833   -0.7063    1.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8430    0.7165   -0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5643    1.2965   -1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2653    0.1713    1.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0792   -1.3188    0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2061   -1.4686   -1.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8727   -0.7651   -1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0953   -0.1031    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5867    0.7128    1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1605    2.3753   -1.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0738    3.0307   -0.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5121    0.5376    1.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1711    2.1403    1.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5448    0.3960   -1.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7769    1.1672   -1.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7861    2.9386    1.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1165    3.2045   -0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9409    2.7236    2.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9819    0.7151    2.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8660   -1.3310    1.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2562   -0.5213    0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6256   -0.0252   -0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1445   -0.8106    1.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929   -2.9075    0.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3689   -2.4607   -0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1775   -0.3675   -2.5760 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  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 22 52  1  0
M  END

HEADER    PROTEIN                                 28-MAY-13   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-MAY-13         0                                  
HETATM    1  C   UNK     0      23.971 -20.379   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.532 -20.379   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.565 -21.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.860 -21.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.238 -20.379   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.187 -20.379   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.676 -20.379   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.749 -20.379   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.349 -21.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      31.154 -21.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.944 -20.379   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      32.482 -20.379   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.616 -21.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      34.043 -20.379   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.289 -20.379   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      35.371 -21.160   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.883 -21.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      14.289 -18.817   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      36.776 -20.379   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      38.338 -20.379   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      39.665 -21.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      40.993 -20.379   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17   18                                                  
CONECT   16   14   19                                                       
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0001999
HETATM    1  C1  UNL     1      -8.254  -1.984  -0.498  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.526  -1.059   0.495  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.061   0.094  -0.284  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.815   0.417  -0.402  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.711  -0.333   0.226  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.792  -0.790  -0.851  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.545  -0.409  -0.884  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.978   0.501   0.151  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.483   1.754  -0.469  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.248   2.097  -0.328  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.809   1.380   0.411  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.849   1.037  -0.583  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.093   1.461  -0.524  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.589   2.317   0.519  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.613   1.892   1.446  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.198   0.774   1.592  1.00  0.00           C  
HETATM   17  C17 UNL     1       5.009  -0.460   0.851  1.00  0.00           C  
HETATM   18  C18 UNL     1       6.360  -0.816   0.226  1.00  0.00           C  
HETATM   19  C19 UNL     1       6.327  -2.132  -0.466  1.00  0.00           C  
HETATM   20  C20 UNL     1       5.390  -2.212  -1.570  1.00  0.00           C  
HETATM   21  O1  UNL     1       5.191  -3.371  -2.078  1.00  0.00           O  
HETATM   22  O2  UNL     1       4.708  -1.150  -2.105  1.00  0.00           O  
HETATM   23  H1  UNL     1      -7.556  -2.778  -0.864  1.00  0.00           H  
HETATM   24  H2  UNL     1      -9.057  -2.526   0.036  1.00  0.00           H  
HETATM   25  H3  UNL     1      -8.577  -1.424  -1.378  1.00  0.00           H  
HETATM   26  H4  UNL     1      -6.812  -1.621   1.072  1.00  0.00           H  
HETATM   27  H5  UNL     1      -8.383  -0.706   1.167  1.00  0.00           H  
HETATM   28  H6  UNL     1      -7.843   0.717  -0.795  1.00  0.00           H  
HETATM   29  H7  UNL     1      -5.564   1.296  -1.004  1.00  0.00           H  
HETATM   30  H8  UNL     1      -4.265   0.171   1.071  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.079  -1.319   0.672  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.206  -1.469  -1.627  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.873  -0.765  -1.703  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.095  -0.103   0.538  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.587   0.713   1.013  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.161   2.375  -1.039  1.00  0.00           H  
HETATM   37  H15 UNL     1       0.074   3.031  -0.808  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.512   0.538   1.027  1.00  0.00           H  
HETATM   39  H17 UNL     1       1.171   2.140   1.174  1.00  0.00           H  
HETATM   40  H18 UNL     1       1.545   0.396  -1.400  1.00  0.00           H  
HETATM   41  H19 UNL     1       3.777   1.167  -1.365  1.00  0.00           H  
HETATM   42  H20 UNL     1       2.786   2.939   1.029  1.00  0.00           H  
HETATM   43  H21 UNL     1       4.117   3.204  -0.060  1.00  0.00           H  
HETATM   44  H22 UNL     1       4.941   2.724   2.169  1.00  0.00           H  
HETATM   45  H23 UNL     1       5.982   0.715   2.413  1.00  0.00           H  
HETATM   46  H24 UNL     1       4.866  -1.331   1.599  1.00  0.00           H  
HETATM   47  H25 UNL     1       4.256  -0.521   0.090  1.00  0.00           H  
HETATM   48  H26 UNL     1       6.626  -0.025  -0.517  1.00  0.00           H  
HETATM   49  H27 UNL     1       7.144  -0.811   1.026  1.00  0.00           H  
HETATM   50  H28 UNL     1       5.993  -2.907   0.301  1.00  0.00           H  
HETATM   51  H29 UNL     1       7.369  -2.461  -0.756  1.00  0.00           H  
HETATM   52  H30 UNL     1       5.177  -0.367  -2.576  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4    4   28
CONECT    4    5   29
CONECT    5    6   30   31
CONECT    6    7    7   32
CONECT    7    8   33
CONECT    8    9   34   35
CONECT    9   10   10   36
CONECT   10   11   37
CONECT   11   12   38   39
CONECT   12   13   13   40
CONECT   13   14   41
CONECT   14   15   42   43
CONECT   15   16   16   44
CONECT   16   17   45
CONECT   17   18   46   47
CONECT   18   19   48   49
CONECT   19   20   50   51
CONECT   20   21   21   22
CONECT   22   52
END

HMDB0001999
     RDKit          3D
Eicosapentaenoic acid
 52 51  0  0  0  0  0  0  0  0999 V2000
   -8.2536   -1.9837   -0.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5264   -1.0591    0.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0615    0.0941   -0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8148    0.4167   -0.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7111   -0.3325    0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7921   -0.7899   -0.8515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5453   -0.4088   -0.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9784    0.5012    0.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4828    1.7538   -0.4694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2476    2.0973   -0.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8093    1.3804    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492    1.0367   -0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0926    1.4612   -0.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    2.3170    0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6126    1.8924    1.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1980    0.7745    1.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0086   -0.4602    0.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3603   -0.8164    0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3275   -2.1319   -0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3895   -2.2120   -1.5698 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1907   -3.3712   -2.0784 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7082   -1.1503   -2.1054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5558   -2.7782   -0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0566   -2.5265    0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5770   -1.4240   -1.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8121   -1.6214    1.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3833   -0.7063    1.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8430    0.7165   -0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5643    1.2965   -1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2653    0.1713    1.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0792   -1.3188    0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2061   -1.4686   -1.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8727   -0.7651   -1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0953   -0.1031    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5867    0.7128    1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1605    2.3753   -1.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0738    3.0307   -0.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5121    0.5376    1.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1711    2.1403    1.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5448    0.3960   -1.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7769    1.1672   -1.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7861    2.9386    1.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1165    3.2045   -0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9409    2.7236    2.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9819    0.7151    2.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8660   -1.3310    1.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2562   -0.5213    0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6256   -0.0252   -0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1445   -0.8106    1.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929   -2.9075    0.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3689   -2.4607   -0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1775   -0.3675   -2.5760 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  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 22 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic acid	ChEBI
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoate	ChEBI
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acid	ChEBI
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid	ChEBI
(all-Z)-5,8,11,14,17-Eicosapentaenoic acid	ChEBI
5,8,11,14,17-EICOSAPENTAENOIC ACID	ChEBI
5,8,11,14,17-Icosapentaenoic acid	ChEBI
all-cis-5,8,11,14,17-Eicosapentaenoic acid	ChEBI
all-cis-Icosa-5,8,11,14,17-pentaenoic acid	ChEBI
cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoic acid	ChEBI
cis-5,8,11,14,17-Eicosapentaenoic acid	ChEBI
cis-5,8,11,14,17-EPA	ChEBI
cis-Delta(5,8,11,14,17)-Eicosapentaenoic acid	ChEBI
EPA	ChEBI
Icosapent	ChEBI
Icosapentaenoic acid	ChEBI
Icosapento	ChEBI
Icosapentum	ChEBI
Timnodonic acid	ChEBI
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoate	Kegg
5Z,8Z,11Z,14Z,17Z-Eicosapentaenoic acid	Kegg
(5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoic acid	Kegg
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoate	Generator
(all-Z)-5,8,11,14,17-Eicosapentaenoate	Generator
5,8,11,14,17-EICOSAPENTAENOate	Generator
5,8,11,14,17-Icosapentaenoate	Generator
all-cis-5,8,11,14,17-Eicosapentaenoate	Generator
all-cis-Icosa-5,8,11,14,17-pentaenoate	Generator
cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoate	Generator
cis-5,8,11,14,17-Eicosapentaenoate	Generator
cis-delta(5,8,11,14,17)-Eicosapentaenoate	Generator
cis-Δ(5,8,11,14,17)-eicosapentaenoate	Generator
cis-Δ(5,8,11,14,17)-eicosapentaenoic acid	Generator
Icosapentaenoate	Generator
Timnodonate	Generator
5Z,8Z,11Z,14Z,17Z-Eicosapentaenoate	Generator
(5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoate	Generator
Eicosapentaenoate	Generator
Omega-3-eicosapentaenoic acid	HMDB
Acid, eicosapentanoic	HMDB
Eicosapentanoic acid	HMDB
Omega 3 eicosapentaenoic acid	HMDB
all-cis-Icosapentaenoate	HMDB
all-cis-Icosapentaenoic acid	HMDB
(5Z,8Z,11Z,14Z,17Z)-Eicosa-5,8,11,14,17-pentaenoic acid	HMDB
(all-Z)-delta5,8,11,14,17-Eicosapentaenoic acid	HMDB
(all-Z)-Δ5,8,11,14,17-eicosapentaenoic acid	HMDB
(all-cis)-5,8,11,14,17-Eicosapentaenoic acid	HMDB
FA(20:5(5Z,8Z,11Z,14Z,17Z))	HMDB
FA(20:5n3)	HMDB
Eicosapentaenoic acid	HMDB

Chemical Formula

C₂₀H₃₀O₂

Average Molecular Weight

302.451

Monoisotopic Molecular Weight

302.224580204

IUPAC Name

(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid

Traditional Name

eicosapentaenoic acid

CAS Registry Number

10417-94-4

SMILES

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

InChI Identifier

InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-

InChI Key

JAZBEHYOTPTENJ-JLNKQSITSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

omega-3 fatty acid (CHEBI:28364 )
icosapentaenoic acid (CHEBI:28364 )
Unsaturated fatty acids (C06428 )
Polyunsaturated fatty acids (C06428 )
Liner triterpenes (C06428 )
Unsaturated fatty acids (LMFA01030759 )

Ontology

Not Available

Adipose Tissue (HMDB: HMDB0001999)

Epithelium

Epidermis (HMDB: HMDB0001999)

Muscle tissue

Skeletal Muscle (HMDB: HMDB0001999)

Biofluid or Excreta

Excreta

Urine (PMID: 32966057)
Feces (PMID: 27275383)
Sweat (PMID: 26755145)

Non-excretory biofluid

Blood (PMID: 18203893)

Cell

Hematocyte

Platelet (HMDB: HMDB0001999)

Organ

Cellular substructure

Membrane (HMDB: HMDB0001999)
Extracellular (HMDB: HMDB0001999)

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Poultry

Chicken (FooDB: FOOD00329)
Squab (FooDB: FOOD00481)
Pheasant (FooDB: FOOD00430)
Turkey (FooDB: FOOD00494)
Anatidae (FooDB: FOOD00576)
Quail (FooDB: FOOD00541)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Guinea hen (FooDB: FOOD00373)
Rock ptarmigan (FooDB: FOOD00597)

Venison

Deer (FooDB: FOOD00524)

Bovine

Bison (FooDB: FOOD00301)
Cattle (Beef, Veal) (FooDB: FOOD00495)

Swine

Domestic pig (FooDB: FOOD00536)

Lagomorph

Mountain hare (FooDB: FOOD00581)
Rabbit (FooDB: FOOD00528)

Caprae

Domestic goat (FooDB: FOOD00529)

Aquatic origin

Fish

Fishes (FooDB: FOOD00865)
Bluefish (FooDB: FOOD00306)
Atlantic wolffish (FooDB: FOOD00296)
Common carp (FooDB: FOOD00322)
Atlantic herring (FooDB: FOOD00292)
Atlantic pollock (FooDB: FOOD00295)
Striped bass (FooDB: FOOD00298)
Northern bluefin tuna (FooDB: FOOD00305)
Cisco (FooDB: FOOD00334)
Channel catfish (FooDB: FOOD00324)
Pacific cod (FooDB: FOOD00337)
Atlantic cod (FooDB: FOOD00338)
Atlantic croaker (FooDB: FOOD00345)
Freshwater eel (FooDB: FOOD00357)
European anchovy (FooDB: FOOD00362)
Florida pompano (FooDB: FOOD00366)
Greenland halibut/turbot (FooDB: FOOD00370)
Grouper (FooDB: FOOD00372)
Hippoglossus (Common halibut) (FooDB: FOOD00375)
King mackerel (FooDB: FOOD00392)
Lingcod (FooDB: FOOD00398)
Striped mullet (FooDB: FOOD00412)
Burbot (FooDB: FOOD00313)
Freshwater drum (FooDB: FOOD00352)
Pacific jack mackerel (FooDB: FOOD00383)
Pacific herring (FooDB: FOOD00424)
Northern pike (FooDB: FOOD00431)
Pacific rockfish (FooDB: FOOD00426)
Rainbow trout (FooDB: FOOD00444)
Orange roughy (FooDB: FOOD00448)
Pink salmon (FooDB: FOOD00450)
Sablefish (FooDB: FOOD00449)
Chum salmon (FooDB: FOOD00451)
Atlantic salmon (FooDB: FOOD00455)
Coho salmon (FooDB: FOOD00452)
Sockeye salmon (FooDB: FOOD00453)
Chinook salmon (FooDB: FOOD00454)
Rainbow smelt (FooDB: FOOD00443)
Scup (FooDB: FOOD00463)
Shark (FooDB: FOOD00471)
Spanish mackerel (FooDB: FOOD00460)
Sea trout (FooDB: FOOD00468)
American shad (FooDB: FOOD00470)
Snapper (FooDB: FOOD00477)
Sheepshead (FooDB: FOOD00474)
Skipjack tuna (FooDB: FOOD00476)
Greater sturgeon (FooDB: FOOD00483)
White sucker (FooDB: FOOD00484)
Pumpkinseed sunfish (FooDB: FOOD00486)
Swordfish (FooDB: FOOD00487)
Tilefish (FooDB: FOOD00490)
Whitefish (FooDB: FOOD00503)
Pollock (FooDB: FOOD00513)
Gadus (Common cod) (FooDB: FOOD00515)
Sheefish (FooDB: FOOD00472)
Whiting (FooDB: FOOD00504)
Yellowfin tuna (FooDB: FOOD00511)
Atlantic halibut (FooDB: FOOD00516)
Percoidei (Bass and others) (FooDB: FOOD00526)
Flatfish (FooDB: FOOD00535)
Pacific halibut (FooDB: FOOD00517)
Spot croaker (FooDB: FOOD00557)
Anchovy (FooDB: FOOD00566)
Sturgeon (FooDB: FOOD00570)
Anguilliformes (FooDB: FOOD00577)
Gadiformes (FooDB: FOOD00580)
Lemon sole (FooDB: FOOD00583)
Catfish (FooDB: FOOD00605)
Carp bream (FooDB: FOOD00568)
Pacific ocean perch (FooDB: FOOD00598)
True sole (FooDB: FOOD00604)
Cichlidae (Tilapia) (FooDB: FOOD00699)
Norway haddock (FooDB: FOOD00588)
Japanese sea bass (FooDB: FOOD00974)
Haddock (FooDB: FOOD00374)
Blue whiting (FooDB: FOOD00567)
Clupeinae (Herring, Sardine, Sprat) (FooDB: FOOD00520)
Charr (FooDB: FOOD00571)
Spiny dogfish (FooDB: FOOD00575)
Common dab (FooDB: FOOD00574)
Garfish (FooDB: FOOD00579)
Lake trout (FooDB: FOOD00582)
Common ling (FooDB: FOOD00397)
Lumpsucker (FooDB: FOOD00585)
Scombridae (Bonito, Mackerel, Tuna) (FooDB: FOOD00586)
Norway pout (FooDB: FOOD00590)
Perciformes (FooDB: FOOD00527)
Pikeperch (FooDB: FOOD00595)
Pleuronectidae (Dab, Halibut, Plaice) (FooDB: FOOD00596)
Salmonidae (Salmon, Trout) (FooDB: FOOD00493)
Thunnus (FooDB: FOOD00607)
Turbot (FooDB: FOOD00364)
Atlantic menhaden (FooDB: FOOD00560)
Dolphin fish (FooDB: FOOD00351)
Atlantic mackerel (FooDB: FOOD00293)
Painted comber (FooDB: FOOD00294)
Walleye (FooDB: FOOD00496)
Alaska pollock (FooDB: FOOD00497)
Pacific sardine (FooDB: FOOD00461)
Albacore tuna (FooDB: FOOD00514)
Smelt (FooDB: FOOD00519)

Crustacean

Mollusk

Blue mussel (FooDB: FOOD00304)
Common octopus (FooDB: FOOD00339)
Cuttlefish (FooDB: FOOD00347)
Eastern oyster (FooDB: FOOD00356)
Pacific oyster (FooDB: FOOD00425)
Scallop (FooDB: FOOD00462)
Whelk (FooDB: FOOD00500)
Squid (FooDB: FOOD00532)
Marine mussel (FooDB: FOOD00587)
Snail (FooDB: FOOD00603)
True oyster (FooDB: FOOD00592)
Abalone (FooDB: FOOD00279)
Bivalvia (Clam, Mussel, Oyster) (FooDB: FOOD00531)
Conch (FooDB: FOOD00611)

Seaweed

Roe

Roe (FooDB: FOOD00698)

Bivalvia

Clam (FooDB: FOOD00952)

Amphibian

True frog (FooDB: FOOD00578)

Fish product

Other fish product (FooDB: FOOD00665)

Pinniped

Cetacean

Cetacea (Dolphin, Porpoise, Whale) (FooDB: FOOD00609)
Beluga whale (FooDB: FOOD00300)

Other aquatic food

Jellyfish (FooDB: FOOD00565)
Green turtle (FooDB: FOOD00702)

Vegetable

Onion-family vegetable

Cabbage

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Water spinach (FooDB: FOOD00977)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Lettuce (FooDB: FOOD00095)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Swamp cabbage (FooDB: FOOD00091)
Romaine lettuce (FooDB: FOOD00888)

Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Eggplant (FooDB: FOOD00174)
Jalapeno pepper (FooDB: FOOD00955)
Groundcherry (FooDB: FOOD00371)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Red bell pepper (FooDB: FOOD00880)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Italian sweet red pepper (FooDB: FOOD00881)

Stalk vegetable

Garden rhubarb (FooDB: FOOD00154)
Celery stalks (FooDB: FOOD00215)

Other vegetable

Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)
Sacred lotus (FooDB: FOOD00402)
Horseradish tree (FooDB: FOOD00379)
Chinese water chestnut (FooDB: FOOD00332)
Carob (FooDB: FOOD00321)

Mushroom

Vegetable product

Other vegetable product (FooDB: FOOD00671)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Nut

Peanut (FooDB: FOOD00016)
Cashew nut (FooDB: FOOD00011)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pistachio (FooDB: FOOD00140)
Pine nut (FooDB: FOOD00138)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Butternut (FooDB: FOOD00316)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Chestnut (FooDB: FOOD00045)
European chestnut (FooDB: FOOD00363)
Mixed nuts (FooDB: FOOD00771)

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Persian lime (FooDB: FOOD00543)
Grapefruit (FooDB: FOOD00256)
Sweet orange (FooDB: FOOD00057)

Drupe

Apricot (FooDB: FOOD00144)
Nectarine (FooDB: FOOD00229)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)

Berry

Redcurrant (FooDB: FOOD00156)
Grape (FooDB: FOOD00369)
Loganberry (FooDB: FOOD00400)
Black raisin (FooDB: FOOD00968)
Green plum (FooDB: FOOD00979)
Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Lingonberry (FooDB: FOOD00194)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)

Fruit product

Cereal and cereal product

Other bread (FooDB: FOOD00269)
Potato bread (FooDB: FOOD00811)

Bread products

Other bread product (FooDB: FOOD00805)

Flat bread

Sweet bread

Raisin bread (FooDB: FOOD00817)

Gourd

Cucumber (FooDB: FOOD00065)
Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Chayote (FooDB: FOOD00325)
Butternut squash (FooDB: FOOD00317)
Yellow zucchini (FooDB: FOOD00876)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Bean

Green lentil (FooDB: FOOD00970)

Soy

Soy product

Soy bean (FooDB: FOOD00085)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)

Beverage

Fermented beverage

Distilled beverage

Vodka (FooDB: FOOD00622)
Spirit (FooDB: FOOD00276)
Gin (FooDB: FOOD00625)
Liquor (FooDB: FOOD00616)
Rum (FooDB: FOOD00629)
Whisky (FooDB: FOOD00623)

Other beverage

Fortified wines

Water

Water (FooDB: FOOD00664)

Nutritional beverage

Nutritional drink (FooDB: FOOD00754)
Energy drink (FooDB: FOOD00703)

Alcoholic beverage

Cocktail (FooDB: FOOD00739)
Other alcoholic beverage (FooDB: FOOD00278)

Confectionery

Other confectionery

Honey (FooDB: FOOD00626)
Marzipan (FooDB: FOOD00644)
Nougat (FooDB: FOOD00634)
Toffee (FooDB: FOOD00635)
Meringue (FooDB: FOOD00680)
Icing (FooDB: FOOD00700)

Chocolate spread (FooDB: FOOD00676)
Dulce de leche (FooDB: FOOD00714)

Milk dessert

Sweet custard (FooDB: FOOD00716)
Junket (FooDB: FOOD00726)

Milk and milk product

Other milk product

Fermented milk

Fermented milk product

Unfermented milk

Milk (Other mammals) (FooDB: FOOD00690)
Milk (Human) (FooDB: FOOD00666)
Milk (Cow) (FooDB: FOOD00618)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)

Baking good

Substitute

Seasoning

Vinegar (FooDB: FOOD00628)
Salt (FooDB: FOOD00647)
Adobo (FooDB: FOOD00758)

Sugar

Sugar (FooDB: FOOD00651)

Dressing

Salad dressing (FooDB: FOOD00645)

Condiment

Sauce

Sauce (FooDB: FOOD00646)

Margarine-like spread (FooDB: FOOD00844)
Margarine (FooDB: FOOD00843)
Shortening (FooDB: FOOD00783)

Fish oil (FooDB: FOOD00990)

Cocoa and cocoa product

Cocoa product

Baby food

Baby food (FooDB: FOOD00668)

Unclassified food or beverage

Unclassified food or beverage (FooDB: FOOD00672)

Dish

Ground meat

Sausage (FooDB: FOOD00652)
Meatball (FooDB: FOOD00653)
Pate (FooDB: FOOD00655)
Meatloaf (FooDB: FOOD00737)
Cold cut (FooDB: FOOD00770)

Potato puffs (FooDB: FOOD00846)
Potato gratin (FooDB: FOOD00847)

Jewish cuisine

Gefilte fish (FooDB: FOOD00833)

Tex-mex cuisine

Chili (FooDB: FOOD00707)
Nachos (FooDB: FOOD00710)
Burrito (FooDB: FOOD00704)
Taco (FooDB: FOOD00708)

Levantine cuisine

Hummus (FooDB: FOOD00845)

Sandwich

Berber cuisine

Couscous (FooDB: FOOD00740)

Mexican cuisine

Quesadilla (FooDB: FOOD00748)

Asian cuisine

Egg roll (FooDB: FOOD00717)
Rice cake (FooDB: FOOD00796)

Latin american cuisine

Tamale (FooDB: FOOD00795)
Empanada (FooDB: FOOD00830)
Pupusa (FooDB: FOOD00829)
Arepa (FooDB: FOOD00831)

Coffee and coffee product

Coffee

Coffee product

Coffee mocha (FooDB: FOOD00743)

Snack

Egg

Eggs (FooDB: FOOD00619)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Alpha Linolenic Acid and Linoleic Acid Metabolism (HMDB: HMDB0001999)

5-hydroxyeicosatetraenoic-acid inhibitor (HMDB: HMDB0001999)
collagenase inhibitor (HMDB: HMDB0001999)
cyclooxygenase 2 inhibitor (HMDB: HMDB0001999)
tyrosine-kinase inhibitor (HMDB: HMDB0001999)
VEGF inhibitor (HMDB: HMDB0001999)

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

nephroprotective agent (HMDB: HMDB0001999)

Pharmaceutical industry

Biomarker

Isovaleric acidemia (MarkerDB: MDB00000363)
Hypertension (MarkerDB: MDB00000363)

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]-	MetCCS_train_neg	178.535	30932474
[M-H]-	Not Available	178.535	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000259

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00029 g/L	ALOGPS
logP	6.53	ALOGPS
logP	6.23	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	101.07 m³·mol⁻¹	ChemAxon
Polarizability	35.93 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	184.623	31661259
DarkChem	[M-H]-	184.428	31661259
DeepCCS	[M+H]+	181.904	30932474
DeepCCS	[M-H]-	179.546	30932474
DeepCCS	[M-2H]-	212.432	30932474
DeepCCS	[M+Na]+	187.997	30932474
AllCCS	[M+H]+	181.2	32859911
AllCCS	[M+H-H2O]+	178.1	32859911
AllCCS	[M+NH4]+	184.0	32859911
AllCCS	[M+Na]+	184.9	32859911
AllCCS	[M-H]-	180.4	32859911
AllCCS	[M+Na-2H]-	182.0	32859911
AllCCS	[M+HCOO]-	183.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Eicosapentaenoic acid	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O	3845.0	Standard polar	33892256
Eicosapentaenoic acid	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O	2092.3	Standard non polar	33892256
Eicosapentaenoic acid	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O	2330.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Eicosapentaenoic acid,1TMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2364.4	Semi standard non polar	33892256
Eicosapentaenoic acid,1TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2613.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Eicosapentaenoic acid GC-MS (1 TMS)	splash10-004l-9700000000-09ea61ed836b88205028	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Eicosapentaenoic acid GC-MS (Non-derivatized)	splash10-004l-9700000000-09ea61ed836b88205028	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eicosapentaenoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-5490000000-ee15446245c5d0190ca2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eicosapentaenoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0adr-9462000000-6310373b498d395ee4b1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eicosapentaenoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-05ox-9400000000-567226e93d65502352cd	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 - Eicosapentaenoic acid LC-ESI-QQ , negative-QTOF	splash10-0udi-0029000000-02c67e3601df249d2476	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosapentaenoic acid 10V, Positive-QTOF	splash10-0udi-0009000000-1f183f43649d7b5d2f92	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosapentaenoic acid 20V, Positive-QTOF	splash10-0udi-2987000000-6239462e49ad0240cfd9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosapentaenoic acid 10V, Negative-QTOF	splash10-0udi-0009000000-028a784c6c5a01da151c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosapentaenoic acid 40V, Positive-QTOF	splash10-000x-9600000000-177a8f3f229d3ffe1c4f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosapentaenoic acid 20V, Negative-QTOF	splash10-0udi-0039000000-41dbbfbea0e69ff3303d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eicosapentaenoic acid 20V, Positive-QTOF	splash10-0udi-2988000000-6239462e49ad0240cfd9	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoic acid 10V, Positive-QTOF	splash10-0udr-1196000000-2fd0631ba34b61c02823	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoic acid 20V, Positive-QTOF	splash10-0a4l-5891000000-6b514ce76e6321b59f49	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoic acid 40V, Positive-QTOF	splash10-052f-8950000000-5f7ac71eb4fd77059c96	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoic acid 10V, Negative-QTOF	splash10-0udi-0029000000-63f4108595227b77b5f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoic acid 20V, Negative-QTOF	splash10-0zfr-2079000000-c196324eb61e1a26da90	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoic acid 40V, Negative-QTOF	splash10-0a4i-9230000000-844643f720715a477b35	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoic acid 10V, Negative-QTOF	splash10-0udi-0019000000-da419ae96bb8b07031de	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoic acid 20V, Negative-QTOF	splash10-0ue9-2179000000-483c2cd6dc1d5799c3e4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoic acid 40V, Negative-QTOF	splash10-0596-9530000000-b5f6ca6a7368abde8826	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoic acid 10V, Positive-QTOF	splash10-0f79-3985000000-f0a1f1db5a552a314689	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoic acid 20V, Positive-QTOF	splash10-001l-5910000000-a82843e1aa65987b4a17	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoic acid 40V, Positive-QTOF	splash10-00l6-9600000000-da4dd030385c445969bc	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)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Sweat
Urine

Tissue Locations

Adipose Tissue
Epidermis
Erythrocyte
Fibroblasts
Kidney
Leukocyte
Liver
Placenta
Platelet
Skeletal Muscle

Pathways

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

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.435 +/- 0.010 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	2100.0 +/- 990.0 uM	Adult (>18 years old)	Male	Normal	18203893	details
Blood	Detected and Quantified	11.0 +/- 8.3 uM	Adult (>18 years old)	Both	Normal	18633173	details
Blood	Detected and Quantified	1.09 +/- 0.72 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	11.1 +/- 9.5 uM	Adult (>18 years old)	Male	Normal	18633173	details
Blood	Detected and Quantified	10.8 +/- 6.2 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	32966057	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)	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)	Female	Normal	27355821	details
Blood	Detected and Quantified	270 +/- 160 uM	Adult (>18 years old)	Male	Normal	18203893	details
Blood	Detected and Quantified	36.370 +/- 16.532 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	33.0632 +/- 9.919 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	23.144 +/- 9.919 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	0.00039 uM	Adult (>18 years old)	Both	Normal	11593343	details
Blood	Detected and Quantified	0.00058 uM	Adult (>18 years old)	Both	Normal	11593343	details
Blood	Detected and Quantified	0.00052 uM	Adult (>18 years old)	Both	Normal	11593343	details
Blood	Detected and Quantified	0.00073 uM	Adult (>18 years old)	Both	Normal	11593343	details
Blood	Detected and Quantified	19.838 +/- 9.919 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	37.890 +/- 24.764 uM	Adult (>18 years old)	Both	Normal	17313719	details
Blood	Detected and Quantified	66.457 +/- 42.321 uM	Adult (>18 years old)	Both	Normal	21185973	details
Blood	Detected and Quantified	70.425 +/- 48.603 uM	Adult (>18 years old)	Both	Normal	21185973	details
Blood	Detected and Quantified	260 +/- 110 uM	Adult (>18 years old)	Female	Normal	14608088	details
Blood	Detected and Quantified	79.649 +/- 51.182 uM	Adult (>18 years old)	Female	Normal	9368807	details
Blood	Detected and Quantified	200 +/- 110 uM	Adult (>18 years old)	Male	Normal	14608088	details
Blood	Detected and Quantified	0.401 +/- 0.068 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	67.6 +/- 50.2 uM	Adult (>18 years old)	Not Specified	Normal	27329611	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
Sweat	Detected but not Quantified	Not Quantified	Adult	Both	Normal	26755145	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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	11.0 +/- 7.3 uM	Adult (>18 years old)	Both	Hypertension	18633173	details
Blood	Detected and Quantified	10.6 +/- 7.2 uM	Adult (>18 years old)	Male	Essential hypertension	18633173	details
Blood	Detected and Quantified	11.9 +/- 7.6 uM	Adult (>18 years old)	Female	Essential hypertension	18633173	details
Blood	Detected and Quantified	63.151 +/- 36.700 uM	Adult (>18 years old)	Both	Depression	21185973	details
Blood	Detected and Quantified	13.9 +/- 17.9 uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	27329611	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	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	Adult (>18 years old)	Both	Colorectal Cancer	27275383	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 ]
Isovaleric acidemia
Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] 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 ]

Associated OMIM IDs

145500 (Hypertension)
608516 (Major depressive disorder)
243500 (Isovaleric acidemia)
114500 (Colorectal cancer)

External Links

DrugBank ID

DB00159

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Eicosapentaenoic acid

METLIN ID

6423

PubChem Compound

446284

PDB ID

Not Available

ChEBI ID

28364

Food Biomarker Ontology

Not Available

VMH ID

TMNDNC

MarkerDB ID

MDB00000363

Good Scents ID

Not Available

References

Synthesis Reference

Sandri, Jacqueline; Viala, Jacques. Syntheses of all-(Z)-5,8,11,14,17-Eicosapentaenoic Acid and all-(Z)-4,7,10,13,16,19-Docosahexaenoic Acid from (Z)-1,1,6,6-tetraisopropoxy-3-hexene. Journal of Organic Chemistry (1995), 60(20), 6627-30.

Material Safety Data Sheet (MSDS)

Not Available

General References

Hino K, Murakami Y, Nagai A, Kitase A, Hara Y, Furutani T, Ren F, Yamaguchi Y, Yutoku K, Yamashita S, Okuda M, Okita M, Okita K: Alpha-tocopherol [corrected] and ascorbic acid attenuates the ribavirin [corrected] induced decrease of eicosapentaenoic acid in erythrocyte membrane in chronic hepatitis C patients. J Gastroenterol Hepatol. 2006 Aug;21(8):1269-75. [PubMed:16872308 ]
Francois CA, Connor SL, Bolewicz LC, Connor WE: Supplementing lactating women with flaxseed oil does not increase docosahexaenoic acid in their milk. Am J Clin Nutr. 2003 Jan;77(1):226-33. [PubMed:12499346 ]
Hafstrom I, Ringertz B, Gyllenhammar H, Palmblad J, Harms-Ringdahl M: Effects of fasting on disease activity, neutrophil function, fatty acid composition, and leukotriene biosynthesis in patients with rheumatoid arthritis. Arthritis Rheum. 1988 May;31(5):585-92. [PubMed:2837251 ]
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 ]
Sipka S, Dey I, Buda C, Csongor J, Szegedi G, Farkas T: The mechanism of inhibitory effect of eicosapentaenoic acid on phagocytic activity and chemotaxis of human neutrophil granulocytes. Clin Immunol Immunopathol. 1996 Jun;79(3):224-8. [PubMed:8635279 ]
Miwa H, Yamamoto M, Futata T, Kan K, Asano T: Thin-layer chromatography and high-performance liquid chromatography for the assay of fatty acid compositions of individual phospholipids in platelets from non-insulin-dependent diabetes mellitus patients: effect of eicosapentaenoic acid ethyl ester administration. J Chromatogr B Biomed Appl. 1996 Mar 3;677(2):217-23. [PubMed:8704924 ]
Kim HH, Shin CM, Park CH, Kim KH, Cho KH, Eun HC, Chung JH: Eicosapentaenoic acid inhibits UV-induced MMP-1 expression in human dermal fibroblasts. J Lipid Res. 2005 Aug;46(8):1712-20. Epub 2005 Jun 1. [PubMed:15930517 ]
Gillis RC, Daley BJ, Enderson BL, Karlstad MD: Eicosapentaenoic acid and gamma-linolenic acid induce apoptosis in HL-60 cells. J Surg Res. 2002 Sep;107(1):145-53. [PubMed:12384078 ]
Takenaga M, Hirai A, Terano T, Tamura Y, Kitagawa H, Yoshida S: Comparison of the in vitro effect of eicosapentaenoic acid (EPA)-derived lipoxygenase metabolites on human platelet function with those of arachidonic acid. Thromb Res. 1986 Feb 1;41(3):373-84. [PubMed:3010490 ]
Hereliuk VI: [The role of arachidonic and eicosapentaenoic acid lipoxygenase products in the pathogenesis of generalized parodontosis]. Fiziol Zh. 2000;46(6):112-5. [PubMed:11424554 ]
Aas V, Rokling-Andersen MH, Kase ET, Thoresen GH, Rustan AC: Eicosapentaenoic acid (20:5 n-3) increases fatty acid and glucose uptake in cultured human skeletal muscle cells. J Lipid Res. 2006 Feb;47(2):366-74. Epub 2005 Nov 21. [PubMed:16301737 ]
Kim HH, Cho S, Lee S, Kim KH, Cho KH, Eun HC, Chung JH: Photoprotective and anti-skin-aging effects of eicosapentaenoic acid in human skin in vivo. J Lipid Res. 2006 May;47(5):921-30. Epub 2006 Feb 7. [PubMed:16467281 ]
Herrmann W, Beitz J: [Decreasing atherogenic risks by an eicosapentaenoic acid-rich diet]. Z Gesamte Inn Med. 1987 Mar 1;42(5):117-22. [PubMed:3035811 ]
Ide T, Okamura T, Kumashiro R, Koga Y, Hino T, Hisamochi A, Ogata K, Tanaka K, Kuwahara R, Seki R, Sata M: A pilot study of eicosapentaenoic acid therapy for ribavirin-related anemia in patients with chronic hepatitis C. Int J Mol Med. 2003 Jun;11(6):729-32. [PubMed:12736713 ]
Dunstan JA, Roper J, Mitoulas L, Hartmann PE, Simmer K, Prescott SL: The effect of supplementation with fish oil during pregnancy on breast milk immunoglobulin A, soluble CD14, cytokine levels and fatty acid composition. Clin Exp Allergy. 2004 Aug;34(8):1237-42. [PubMed:15298564 ]
Luostarinen R, Saldeen T: Dietary fish oil decreases superoxide generation by human neutrophils: relation to cyclooxygenase pathway and lysosomal enzyme release. Prostaglandins Leukot Essent Fatty Acids. 1996 Sep;55(3):167-72. [PubMed:8931114 ]
Calzada C, Vericel E, Lagarde M: Lower levels of lipid peroxidation in human platelets incubated with eicosapentaenoic acid. Biochim Biophys Acta. 1992 Jul 29;1127(2):147-52. [PubMed:1643099 ]
Lagarde M, Croset M, Vericel E, Calzada C: Effects of small concentrations of eicosapentaenoic acid on platelets. J Intern Med Suppl. 1989;731:177-9. [PubMed:2539831 ]
Bays HE, Ballantyne CM, Kastelein JJ, Isaacsohn JL, Braeckman RA, Soni PN: Eicosapentaenoic acid ethyl ester (AMR101) therapy in patients with very high triglyceride levels (from the Multi-center, plAcebo-controlled, Randomized, double-blINd, 12-week study with an open-label Extension [MARINE] trial). Am J Cardiol. 2011 Sep 1;108(5):682-90. doi: 10.1016/j.amjcard.2011.04.015. Epub 2011 Jun 16. [PubMed:21683321 ]
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 ]

Only showing the first 10 proteins. There are 16 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Bile acid-CoA:amino acid N-acyltransferase

General function:: Involved in thiolester hydrolase activity
Specific function:: Involved in bile acid metabolism. In liver hepatocytes catalyzes the second step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi. The major components of bile are cholic acid and chenodeoxycholic acid. In a first step the bile acids are converted to an acyl-CoA thioester, either in peroxisomes (primary bile acids deriving from the cholesterol pathway), or cytoplasmic at the endoplasmic reticulum (secondary bile acids). May catalyze the conjugation of primary or secondary bile acids, or both. The conjugation increases the detergent properties of bile acids in the intestine, which facilitates lipid and fat-soluble vitamin absorption. In turn, bile acids are deconjugated by bacteria in the intestine and are recycled back to the liver for reconjugation (secondary bile acids). May also act as an acyl-CoA thioesterase that regulates intracellular levels of free fatty acids. In vitro, catalyzes the hydrolysis of long- and very long-chain saturated acyl-CoAs to the free fatty acid and coenzyme A (CoASH), and conjugates glycine to these acyl-CoAs.
Gene Name:: BAAT
Uniprot ID:: Q14032
Molecular weight:: 46298.865

Enzyme Details

2. Long-chain-fatty-acid--CoA ligase 4

General function:: Involved in catalytic activity
Specific function:: Activation of long-chain fatty acids for both synthesis of cellular lipids, and degradation via beta-oxidation. Preferentially uses arachidonate and eicosapentaenoate as substrates.
Gene Name:: ACSL4
Uniprot ID:: O60488
Molecular weight:: 74435.495

References

Heimli H, Hollung K, Drevon CA: Eicosapentaenoic acid-induced apoptosis depends on acyl CoA-synthetase. Lipids. 2003 Mar;38(3):263-8. [PubMed:12784866 ]
Covault J, Pettinati H, Moak D, Mueller T, Kranzler HR: Association of a long-chain fatty acid-CoA ligase 4 gene polymorphism with depression and with enhanced niacin-induced dermal erythema. Am J Med Genet B Neuropsychiatr Genet. 2004 May 15;127B(1):42-7. [PubMed:15108178 ]

Enzyme Details

3. Long-chain-fatty-acid--CoA ligase 3

General function:: Involved in catalytic activity
Specific function:: Acyl-CoA synthetases (ACSL) activates long-chain fatty acids for both synthesis of cellular lipids, and degradation via beta-oxidation. ACSL3 mediates hepatic lipogenesis (By similarity). Preferentially uses myristate, laurate, arachidonate and eicosapentaenoate as substrates (By similarity). Has mainly an anabolic role in energy metabolism. Required for the incorporation of fatty acids into phosphatidylcholine, the major phospholipid located on the surface of VLDL (very low density lipoproteins).
Gene Name:: ACSL3
Uniprot ID:: O95573
Molecular weight:: 80419.415

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

4. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

References

Lee JY, Plakidas A, Lee WH, Heikkinen A, Chanmugam P, Bray G, Hwang DH: Differential modulation of Toll-like receptors by fatty acids: preferential inhibition by n-3 polyunsaturated fatty acids. J Lipid Res. 2003 Mar;44(3):479-86. Epub 2002 Dec 1. [PubMed:12562875 ]
Ait-Said F, Elalamy I, Werts C, Gomard MT, Jacquemin C, Couetil JP, Hatmi M: Inhibition by eicosapentaenoic acid of IL-1beta-induced PGHS-2 expression in human microvascular endothelial cells: involvement of lipoxygenase-derived metabolites and p38 MAPK pathway. Biochim Biophys Acta. 2003 Feb 20;1631(1):77-84. [PubMed:12573452 ]
Machida T, Hiramatsu M, Hamaue N, Minami M, Hirafuji M: Docosahexaenoic acid enhances cyclooxygenase-2 induction by facilitating p44/42, but not p38, mitogen-activated protein kinase activation in rat vascular smooth muscle cells. J Pharmacol Sci. 2005 Sep;99(1):113-6. Epub 2005 Sep 1. [PubMed:16141635 ]
Das UN: Can COX-2 inhibitor-induced increase in cardiovascular disease risk be modified by essential fatty acids? J Assoc Physicians India. 2005 Jul;53:623-7. [PubMed:16190133 ]
Chene G, Dubourdeau M, Balard P, Escoubet-Lozach L, Orfila C, Berry A, Bernad J, Aries MF, Charveron M, Pipy B: n-3 and n-6 polyunsaturated fatty acids induce the expression of COX-2 via PPARgamma activation in human keratinocyte HaCaT cells. Biochim Biophys Acta. 2007 May;1771(5):576-89. Epub 2007 Mar 16. [PubMed:17459764 ]
Vecchio AJ, Simmons DM, Malkowski MG: Structural basis of fatty acid substrate binding to cyclooxygenase-2. J Biol Chem. 2010 Jul 16;285(29):22152-63. doi: 10.1074/jbc.M110.119867. Epub 2010 May 12. [PubMed:20463020 ]

Enzyme Details

5. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Malkowski MG, Thuresson ED, Lakkides KM, Rieke CJ, Micielli R, Smith WL, Garavito RM: Structure of eicosapentaenoic and linoleic acids in the cyclooxygenase site of prostaglandin endoperoxide H synthase-1. J Biol Chem. 2001 Oct 5;276(40):37547-55. Epub 2001 Jul 27. [PubMed:11477109 ]
Machida T, Hiramatsu M, Hamaue N, Minami M, Hirafuji M: Docosahexaenoic acid enhances cyclooxygenase-2 induction by facilitating p44/42, but not p38, mitogen-activated protein kinase activation in rat vascular smooth muscle cells. J Pharmacol Sci. 2005 Sep;99(1):113-6. Epub 2005 Sep 1. [PubMed:16141635 ]
Das UN: COX-2 inhibitors and metabolism of essential fatty acids. Med Sci Monit. 2005 Jul;11(7):RA233-7. Epub 2005 Jun 29. [PubMed:15990700 ]
Das UN: Can COX-2 inhibitor-induced increase in cardiovascular disease risk be modified by essential fatty acids? J Assoc Physicians India. 2005 Jul;53:623-7. [PubMed:16190133 ]
Yang P, Chan D, Felix E, Cartwright C, Menter DG, Madden T, Klein RD, Fischer SM, Newman RA: Formation and antiproliferative effect of prostaglandin E(3) from eicosapentaenoic acid in human lung cancer cells. J Lipid Res. 2004 Jun;45(6):1030-9. Epub 2004 Mar 1. [PubMed:14993240 ]
Vecchio AJ, Simmons DM, Malkowski MG: Structural basis of fatty acid substrate binding to cyclooxygenase-2. J Biol Chem. 2010 Jul 16;285(29):22152-63. doi: 10.1074/jbc.M110.119867. Epub 2010 May 12. [PubMed:20463020 ]
Lee JY, Plakidas A, Lee WH, Heikkinen A, Chanmugam P, Bray G, Hwang DH: Differential modulation of Toll-like receptors by fatty acids: preferential inhibition by n-3 polyunsaturated fatty acids. J Lipid Res. 2003 Mar;44(3):479-86. Epub 2002 Dec 1. [PubMed:12562875 ]

Enzyme Details

6. 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

(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA + Water → Coenzyme A + Eicosapentaenoic acid	details

Enzyme Details

7. 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

(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA + Water → Coenzyme A + Eicosapentaenoic acid	details

Enzyme Details

8. 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

(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA + Water → Coenzyme A + Eicosapentaenoic acid	details

Enzyme Details

9. Acyl-coenzyme A thioesterase 8

General function:: Involved in acyl-CoA thioesterase 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. May mediate Nef-induced down-regulation of CD4. Major thioesterase in peroxisomes. Competes with BAAT (Bile acid CoA: amino acid N-acyltransferase) for bile acid-CoA substrate (such as chenodeoxycholoyl-CoA). Shows a preference for medium-length fatty acyl-CoAs (By similarity). May be involved in the metabolic regulation of peroxisome proliferation.
Gene Name:: ACOT8
Uniprot ID:: O14734
Molecular weight:: 35914.02

Enzyme Details

10. Free fatty acid receptor 1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for medium and long chain saturated and unsaturated fatty acids. Binding of the ligand increase intracellular calcium concentration and amplify glucose-stimulated insulin secretion. The activity of this receptor is mediated by G- proteins that activate phospholipase C. Seems to act through a G(q) and G(i)-mediated pathway
Gene Name:: FFAR1
Uniprot ID:: O14842
Molecular weight:: 31456.6

References

Itoh Y, Hinuma S: GPR40, a free fatty acid receptor on pancreatic beta cells, regulates insulin secretion. Hepatol Res. 2005 Oct;33(2):171-3. Epub 2005 Oct 6. [PubMed:16214394 ]

Only showing the first 10 proteins. There are 16 proteins in total.

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Showing metabocard for Eicosapentaenoic acid (HMDB0001999)

MOL for HMDB0001999 (Eicosapentaenoic acid)

3D MOL for HMDB0001999 (Eicosapentaenoic acid)

3D SDF for HMDB0001999 (Eicosapentaenoic acid)

3D-SDF for HMDB0001999 (Eicosapentaenoic acid)

PDB for HMDB0001999 (Eicosapentaenoic acid)

3D PDB for HMDB0001999 (Eicosapentaenoic acid)

SMILES for HMDB0001999 (Eicosapentaenoic acid)

INCHI for HMDB0001999 (Eicosapentaenoic acid)

Structure for HMDB0001999 (Eicosapentaenoic acid)

3D Structure for HMDB0001999 (Eicosapentaenoic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

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References

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Reactions

References