MiMeDB: Showing metabocard for Eicosapentaenoic acid (MMDBc0000579)

Not Available

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:50:22 UTC

Update Date

2024-10-09 22:51:55 UTC

Metabolite ID

MMDBc0000579

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>
MMDBc0000579

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₂₀H₃₀O₂

Average Mass

302.451

Monoisotopic Mass

302.224580204

IUPAC Name

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

Traditional Name

eicosapentaenoic acid

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-004l-9700000000-09ea61ed836b88205028	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-9700000000-09ea61ed836b88205028	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-5490000000-ee15446245c5d0190ca2	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0adr-9462000000-6310373b498d395ee4b1	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0029000000-02c67e3601df249d2476	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-1f183f43649d7b5d2f92	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-2987000000-6239462e49ad0240cfd9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-028a784c6c5a01da151c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000x-9600000000-177a8f3f229d3ffe1c4f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0039000000-41dbbfbea0e69ff3303d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-2988000000-6239462e49ad0240cfd9	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-1196000000-2fd0631ba34b61c02823	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-5891000000-6b514ce76e6321b59f49	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-8950000000-5f7ac71eb4fd77059c96	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0029000000-63f4108595227b77b5f0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-2079000000-c196324eb61e1a26da90	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9230000000-844643f720715a477b35	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0019000000-da419ae96bb8b07031de	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ue9-2179000000-483c2cd6dc1d5799c3e4	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0596-9530000000-b5f6ca6a7368abde8826	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f79-3985000000-f0a1f1db5a552a314689	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001l-5910000000-a82843e1aa65987b4a17	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00l6-9600000000-da4dd030385c445969bc	2021-09-23	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-05ox-9400000000-567226e93d65502352cd	2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Adipose Tissue
Blood
Epidermis
Erythrocyte
Feces
Fibroblasts
Kidney
Leukocyte
Liver
Placenta
Platelet
Skeletal Muscle
Sweat
Urine

Tissue Locations

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

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192196	Bile acid-CoA:amino acid N-acyltransferase	Enzyme	Q14032	Homo sapiens
MMDBp0192214	Long-chain-fatty-acid--CoA ligase 4	Unknown	O60488	Homo sapiens
MMDBp0192288	Long-chain-fatty-acid--CoA ligase 3	Unknown	O95573	Homo sapiens
MMDBp0192587	Prostaglandin G/H synthase 2	Unknown	P35354	Homo sapiens
MMDBp0192588	Prostaglandin G/H synthase 1	Unknown	P23219	Homo sapiens
MMDBp0192655	Cytosolic acyl coenzyme A thioester hydrolase	Enzyme	O00154	Homo sapiens
MMDBp0192656	Acyl-coenzyme A thioesterase 2, mitochondrial	Enzyme	P49753	Homo sapiens
MMDBp0192657	Acyl-coenzyme A thioesterase 4	Enzyme	Q8N9L9	Homo sapiens
MMDBp0192658	Acyl-coenzyme A thioesterase 8	Enzyme	O14734	Homo sapiens
MMDBp0193393	Free fatty acid receptor 1	Unknown	O14842	Homo sapiens
MMDBp0193442	Peroxisome proliferator-activated receptor gamma	Enzyme	P37231	Homo sapiens
MMDBp0193461	Transient receptor potential cation channel subfamily V member 1	Unknown	Q8NER1	Homo sapiens
MMDBp0193506	Peroxisome proliferator-activated receptor delta	Enzyme	Q03181	Homo sapiens
MMDBp0193627	Fatty acid desaturase 1	Unknown	O60427	Homo sapiens
MMDBp0193782	Sodium/calcium exchanger 1	Unknown	P32418	Homo sapiens
MMDBp0196516	Acyl-coenzyme A thioesterase 1	Enzyme	Q86TX2	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001117	Eicosapentaenoic acid	(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA	Not Available	VMH	15292367
MMDBr0004540	Eicosapentaenoic acid	(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA	Not Available	VMH	10479480 9784915
MMDBr0004838	Eicosapentaenoic acid	5-Hydroperoxy-Epa	Not Available	VMH	10617998
MMDBr0004839	Eicosapentaenoic acid	5-Hydroperoxy-Epa	arachidonate 5-lipoxygenase	VMH	10617998
MMDBr0004841	Eicosapentaenoic acid	15(S)-Hydroperoxy-Epe	Not Available	VMH	11034610
MMDBr0004842	Eicosapentaenoic acid	15(S)-Hydroperoxy-Epe	prostaglandin-endoperoxide synthase 1 (prostaglandin G/H synthase and cyclooxygenase)	VMH	11034610
MMDBr0004843	Eicosapentaenoic acid	15(S)-Hydroperoxy-Epe	prostaglandin-endoperoxide synthase 1 (prostaglandin G/H synthase and cyclooxygenase)	VMH	11034610
MMDBr0004844	Eicosapentaenoic acid	15(S)-Hydroperoxy-Epe	acyl-CoA oxidase 2, branched chain	VMH	11034610
MMDBr0005727	1-Timnodnoyl-Cholesterol, Cholesterol-Ester (20:5, Delta 5,8,11,14,17)	Cholesterol	carboxyl ester lipase	VMH	30371894
MMDBr0009265	(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA	Eicosapentaenoic acid	acyl-CoA thioesterase 1	VMH	30371894
MMDBr0009751	Eicosapentaenoic acid	Prostaglandin H3	prostaglandin-endoperoxide synthase 1 (prostaglandin G/H synthase and cyclooxygenase)	VMH	30371894
MMDBr0009752	Eicosapentaenoic acid	Prostaglandin H3	prostaglandin-endoperoxide synthase 1 (prostaglandin G/H synthase and cyclooxygenase)	VMH	30371894
MMDBr0010215	Cholest-5-En-3Beta-Yl (5Z,8Z,11Z,14Z,17Z-Eicosapentaenoate)	Cholesterol	carboxyl ester lipase	VMH; KEGG	30371894
MMDBr0010252	Cholest-5-En-3Beta-Yl (5Z,8Z,11Z,14Z,17Z-Eicosapentaenoate)	Cholesterol	carboxyl ester lipase	VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Essential hypertension	Decreased	Association	Human Blood	HMDB	18633173
Hypertension		Association	Human Blood	HMDB	18633173
Isovaleric acidemia	Slight Decrease	Association	Human Blood	HMDB	27329611
Major depressive disorder	Increased	Association	Human Blood	HMDB	21185973

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Verrucomicrobia	1	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Bacteroidetes	2	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	4	Human stool; Human ; Human feces; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Species	Data Source	Reference
Animal	Haliotis	FooDB	Manually Annotated
Animal	Strombidae	FooDB	Manually Annotated
Animal	Clupea harengus harengus	FooDB	Manually Annotated
Animal	Undaria pinnatifida	FooDB	Manually Annotated
Animal	Peprilus triacanthus	FooDB	Manually Annotated
Animal	Rhodophyta	FooDB	Manually Annotated
Animal	Myoxocephalus	FooDB	Manually Annotated
Animal	Eucheuma	FooDB	Manually Annotated
Animal	Saccharina japonica	FooDB	Manually Annotated
Animal	Spirulina	FooDB	Manually Annotated
Animal	Lota lota	FooDB	Manually Annotated
Animal	Porphyra umbilicalis	FooDB	Manually Annotated
Animal	Chondrus crispus	FooDB	Manually Annotated
Animal	Laminaria	FooDB	Manually Annotated
Plant	Asparagus officinalis	FooDB	Manually Annotated
Plant	Chamerion angustifolium	FooDB	Manually Annotated
Plant	Levisticum officinale	FooDB	Manually Annotated
Plant	Vaccinium elliottii	FooDB	Manually Annotated
Plant	Ziziphus zizyphus	FooDB	Manually Annotated
Plant	Matricaria recutita	FooDB	Manually Annotated
Plant	Dimocarpus longan	FooDB	Manually Annotated
Plant	Citrus aurantiifolia	FooDB	Manually Annotated
Plant	Lactuca sativa	FooDB	Manually Annotated
Plant	Pimpinella anisum	FooDB	Manually Annotated
Plant	Artemisia dracunculus	FooDB	Manually Annotated
Plant	Salvia hispanica	FooDB	Manually Annotated
Plant	Eragrostis tef	FooDB	Manually Annotated
Plant	Cynara cardunculus	FooDB	Manually Annotated
Plant	Vitellaria paradoxa	FooDB	Manually Annotated
Plant	Pangium edule	FooDB	Manually Annotated
Plant	Pistacia vera	FooDB	Manually Annotated
Plant	Allium	FooDB	Manually Annotated
Plant	Brassica oleracea var. viridis	FooDB	Manually Annotated
Plant	Agave	FooDB	Manually Annotated
Plant	Malus pumila	FooDB	Manually Annotated
Plant	Punica granatum	FooDB	Manually Annotated
Plant	Hedysarum alpinum	FooDB	Manually Annotated
Plant	Diospyros	FooDB	Manually Annotated
Plant	Vigna aconitifolia	FooDB	Manually Annotated
Plant	Amaranthus	FooDB	Manually Annotated
Plant	Mammea americana	FooDB	Manually Annotated
Plant	Gossypium	FooDB	Manually Annotated
Plant	Brassica alboglabra	FooDB	Manually Annotated
Plant	Beta vulgaris	FooDB	Manually Annotated
Plant	Annona squamosa	FooDB	Manually Annotated
Plant	Apium graveolens var. dulce	FooDB	Manually Annotated
Plant		FooDB	Manually Annotated
Plant	Vitis	FooDB	Manually Annotated
Plant	Xanthosoma sagittifolium	FooDB	Manually Annotated
Plant	Basella alba	FooDB	Manually Annotated
Plant	Capsicum baccatum var. baccatum	FooDB	Manually Annotated
Plant	Citrus latifolia	FooDB	Manually Annotated
Plant	Carya illinoinensis	FooDB	Manually Annotated
Plant	Byrsonima crassifolia	FooDB	Manually Annotated
Plant	Cucumis sativus	FooDB	Manually Annotated
Plant	Capsicum pubescens	FooDB	Manually Annotated
Plant	Crateva religiosa	FooDB	Manually Annotated
Plant	Vitis aestivalis	FooDB	Manually Annotated
Plant	Eugenia javanica	FooDB	Manually Annotated
Plant		FooDB	Manually Annotated
Plant	Mentha arvensis	FooDB	Manually Annotated
Plant	Ribes rubrum	FooDB	Manually Annotated
Plant	Brassica rapa var. chinensis	FooDB	Manually Annotated
Plant	Cinnamomum aromaticum	FooDB	Manually Annotated
Plant	Vaccinium stamineum	FooDB	Manually Annotated
Plant	Ipomoea batatas	FooDB	Manually Annotated
Plant	Portulaca oleracea	FooDB	Manually Annotated
Plant	Solanum lycopersicum var. cerasiforme	FooDB	Manually Annotated
Plant	Chenopodium album	FooDB	Manually Annotated
Plant	Cucurbita maxima	FooDB	Manually Annotated
Plant	Psophocarpus tetragonolobus	FooDB	Manually Annotated
Plant	Pastinaca sativa	FooDB	Manually Annotated
Plant	Allium ampeloprasum	FooDB	Manually Annotated
Plant	Sechium edule	FooDB	Manually Annotated
Plant	Brassica oleracea	FooDB	Manually Annotated
Plant	Grataegosorbus mitschurinii	FooDB	Manually Annotated
Plant	Lactuca sativa l. var. longifolia	FooDB	Manually Annotated
Plant	Origanum x majoricum	FooDB	Manually Annotated
Plant	Diospyros virginiana	FooDB	Manually Annotated
Plant	Rubus x loganobaccus	FooDB	Manually Annotated
Plant	Tragopogon porrifolius	FooDB	Manually Annotated
Plant	Taraxacum officinale	FooDB	Manually Annotated
Plant	Rumex	FooDB	Manually Annotated
Plant	Allium ascalonicum	FooDB	Manually Annotated
Plant	Curcuma longa	FooDB	Manually Annotated
Plant	Rubus chamaemorus	FooDB	Manually Annotated
Plant	Citrullus lanatus var. fistulosus	FooDB	Manually Annotated
Plant	Elettaria cardamomum	FooDB	Manually Annotated
Plant	Amelanchier alnifolia	FooDB	Manually Annotated
Plant	Eugenia uniflora	FooDB	Manually Annotated
Plant	Ananas comosus	FooDB	Manually Annotated
Plant	Persea americana	FooDB	Manually Annotated
Plant	Annona reticulata	FooDB	Manually Annotated
Plant	Sesbania bispinosa	FooDB	Manually Annotated
Plant	Ribes x nidigrolaria	FooDB	Manually Annotated
Plant	Chenopodium quinoa	FooDB	Manually Annotated
Plant	Cichorium intybus	FooDB	Manually Annotated
Plant	Brassica oleracea var. botrytis	FooDB	Manually Annotated
Plant	Garcinia mangostana	FooDB	Manually Annotated
Plant	Lathyrus sativus	FooDB	Manually Annotated
Plant	Dioscorea pentaphylla	FooDB	Manually Annotated
Plant	Allium tuberosum	FooDB	Manually Annotated
Plant	Cucumis melo	FooDB	Manually Annotated
Plant	Corchorus olitorius	FooDB	Manually Annotated
Plant	Juglans nigra	FooDB	Manually Annotated
Plant	Gaylussacia baccata	FooDB	Manually Annotated
Plant	Petasites japonicus	FooDB	Manually Annotated
Plant	Cinnamomum verum	FooDB	Manually Annotated
Plant	Prunus tomentosa	FooDB	Manually Annotated
Plant	Glycine max	FooDB	Manually Annotated
Plant	Mentha x piperita	FooDB	Manually Annotated
Plant	Maranta arundinacea	FooDB	Manually Annotated
Plant	Ocimum basilicum	FooDB	Manually Annotated
Plant	Matteuccia struthiopteris	FooDB	Manually Annotated
Plant	Cucurbita moschata	FooDB	Manually Annotated
Plant	Macadamia	FooDB	Manually Annotated
Plant	Tilia	FooDB	Manually Annotated
Plant	Vaccinium myrtilloides	FooDB	Manually Annotated
Plant	Citrus limon	FooDB	Manually Annotated
Plant	Capsicum annuum var. annuum	FooDB	Manually Annotated
Plant	Papaver	FooDB	Manually Annotated
Plant	Rosa	FooDB	Manually Annotated
Plant	Nelumbo	FooDB	Manually Annotated
Plant	Apium graveolens var. rapaceum	FooDB	Manually Annotated
Plant	Brassica oleracea var. conica	FooDB	Manually Annotated
Plant	Sesamum orientale	FooDB	Manually Annotated
Plant	Annona cherimola	FooDB	Manually Annotated
Plant	Lippia graveolens	FooDB	Manually Annotated
Plant	Brassica rapa var. pekinensis	FooDB	Manually Annotated
Plant	Brassica rapa	FooDB	Manually Annotated
Plant	Prunus	FooDB	Manually Annotated
Plant	Capparis spinosa	FooDB	Manually Annotated
Plant	Citrus sinensis	FooDB	Manually Annotated
Plant	Lens culinaris	FooDB	Manually Annotated
Plant	Vaccinium deliciosum	FooDB	Manually Annotated
Plant	Phaseolus lunatus	FooDB	Manually Annotated
Plant	Artocarpus heterophyllus	FooDB	Manually Annotated
Plant	Prunus virginiana	FooDB	Manually Annotated
Plant	Musa acuminata	FooDB	Manually Annotated
Plant	Citrullus lanatus	FooDB	Manually Annotated
Plant	Vigna unguiculata ssp. unguiculata	FooDB	Manually Annotated
Plant	Macadamia tetraphylla	FooDB	Manually Annotated
Plant	Linum usitatissimum	FooDB	Manually Annotated
Plant	Lagenaria siceraria	FooDB	Manually Annotated
Plant	Carum carvi	FooDB	Manually Annotated
Plant	Carissa macrocarpa	FooDB	Manually Annotated
Plant	Prunus domestica	FooDB	Manually Annotated
Plant	Prunus armeniaca	FooDB	Manually Annotated
Plant	Phyllostachys edulis	FooDB	Manually Annotated
Plant	Satureja hortensis	FooDB	Manually Annotated
Plant	Allium schoenoprasum	FooDB	Manually Annotated
Plant	Citrus reticulata	FooDB	Manually Annotated
Plant	Averrhoa carambola	FooDB	Manually Annotated
Plant	Sorbus aucuparia	FooDB	Manually Annotated
Plant	Brassica rapa var. rapa	FooDB	Manually Annotated
Plant	Nelumbo nucifera	FooDB	Manually Annotated
Plant	Brassica oleracea var. costata	FooDB	Manually Annotated
Plant	Anethum graveolens	FooDB	Manually Annotated
Plant	Panax	FooDB	Manually Annotated
Plant	Bertholletia excelsa	FooDB	Manually Annotated
Plant	Coriandrum sativum	FooDB	Manually Annotated
Plant	Ceratonia siliqua	FooDB	Manually Annotated
Plant	Cymbopogon citratus	FooDB	Manually Annotated
Plant	Luffa aegyptiaca	FooDB	Manually Annotated
Plant	Rubus occidentalis	FooDB	Manually Annotated
Plant	Vigna umbellata	FooDB	Manually Annotated
Plant	Carthamus tinctorius	FooDB	Manually Annotated
Plant	Cicer arietinum	FooDB	Manually Annotated
Plant	Allium fistulosum	FooDB	Manually Annotated
Plant	Capsicum	FooDB	Manually Annotated
Plant	Lupinus	FooDB	Manually Annotated
Plant	Anacardium occidentale	FooDB	Manually Annotated
Plant	Tilia cordata	FooDB	Manually Annotated
Plant	Vaccinium alaskaense	FooDB	Manually Annotated
Plant	Prunus persica var. nucipersica	FooDB	Manually Annotated
Plant	Durio zibethinus	FooDB	Manually Annotated
Plant	Eriobotrya japonica	FooDB	Manually Annotated
Plant	Brassica napus var. pabularia	FooDB	Manually Annotated
Plant	Ribes glandulosum	FooDB	Manually Annotated
Plant	Camellia sinensis	FooDB	Manually Annotated
Plant	Diospyros kaki	FooDB	Manually Annotated
Plant	Oenothera biennis	FooDB	Manually Annotated
Plant	Verbena officinalis	FooDB	Manually Annotated
Plant	Virola surinamensis	FooDB	Manually Annotated
Plant	Vaccinium oxycoccos	FooDB	Manually Annotated
Plant	Theobroma cacao	FooDB	Manually Annotated
Plant	Solanum lycopersicum var. lycopersicum	FooDB	Manually Annotated
Plant	Rumex acetosa	FooDB	Manually Annotated
Plant	Phaseolus vulgaris	FooDB	Manually Annotated
Plant	Vaccinium parvifolium	FooDB	Manually Annotated
Plant	Aloysia triphylla	FooDB	Manually Annotated
Plant	Pyrus pyrifolia	FooDB	Manually Annotated
Plant	Daucus carota ssp. sativus	FooDB	Manually Annotated
Plant	Capsicum chinense	FooDB	Manually Annotated
Plant	Brassica oleracea var. capitata	FooDB	Manually Annotated
Plant	Vaccinium myrtillus	FooDB	Manually Annotated
Plant	Syzygium aromaticum	FooDB	Manually Annotated
Plant	Vaccinium reticulatum	FooDB	Manually Annotated
Plant	Solanum quitoense	FooDB	Manually Annotated
Plant	Theobroma grandiflorum	FooDB	Manually Annotated
Plant	Vicia faba	FooDB	Manually Annotated
Plant	Ginkgo biloba	FooDB	Manually Annotated
Plant	Vigna unguiculata ssp. cylindrica	FooDB	Manually Annotated
Plant	Flammulina velutipes	FooDB	Manually Annotated
Plant	Satureja montana	FooDB	Manually Annotated
Plant		FooDB	Manually Annotated
Plant	Citrus japonica	FooDB	Manually Annotated
Plant	Perideridia oregana	FooDB	Manually Annotated
Plant	Prunus avium	FooDB	Manually Annotated
Plant	Vaccinium arboreum	FooDB	Manually Annotated
Plant	Pouteria sapota	FooDB	Manually Annotated
Plant	Wasabia japonica	FooDB	Manually Annotated
Plant	Origanum onites	FooDB	Manually Annotated
Plant	Piper nigrum	FooDB	Manually Annotated
Plant	Vitis vinifera	FooDB	Manually Annotated
Plant	Capsicum annuum	FooDB	Manually Annotated
Plant	Origanum vulgare	FooDB	Manually Annotated
Plant	Viburnum edule	FooDB	Manually Annotated
Plant	Dioscorea	FooDB	Manually Annotated
Plant	Vaccinium uliginosum	FooDB	Manually Annotated
Plant	Momordica charantia	FooDB	Manually Annotated
Plant	Rubus ursinus x idaeus	FooDB	Manually Annotated
Plant	Brassica oleracea var. italica	FooDB	Manually Annotated
Plant	Castanea	FooDB	Manually Annotated
Plant	Pleurotus ostreatus	FooDB	Manually Annotated
Plant	Cirsium	FooDB	Manually Annotated
Plant	Opuntia	FooDB	Manually Annotated
Plant	Solanum melongena	FooDB	Manually Annotated
Plant	Raphanus sativus var. sativus	FooDB	Manually Annotated
Plant	Colocasia esculenta	FooDB	Manually Annotated
Plant	Prunus persica var. persica	FooDB	Manually Annotated
Plant	Anthriscus cerefolium	FooDB	Manually Annotated
Plant	Nuphar lutea	FooDB	Manually Annotated
Plant	Pachyrhizus erosus	FooDB	Manually Annotated
Plant	Lupinus albus	FooDB	Manually Annotated
Plant	Myristica fragrans	FooDB	Manually Annotated
Plant	Cichorium endivia	FooDB	Manually Annotated
Plant	Elaeis	FooDB	Manually Annotated
Plant	Feijoa sellowiana	FooDB	Manually Annotated
Plant	Dysphania ambrosioides	FooDB	Manually Annotated
Plant	Cinnamomum	FooDB	Manually Annotated
Plant	Photinia melanocarpa	FooDB	Manually Annotated
Plant	Ribes uva-crispa	FooDB	Manually Annotated
Plant	Raphanus sativus var. niger	FooDB	Manually Annotated
Plant	Apium graveolens	FooDB	Manually Annotated
Plant	Rheum rhabarbarum	FooDB	Manually Annotated
Plant	Vaccinium	FooDB	Manually Annotated
Plant	Lablab purpureus	FooDB	Manually Annotated
Plant	Crocus sativus	FooDB	Manually Annotated
Plant	Salvia officinalis	FooDB	Manually Annotated
Plant	Syzygium jambos	FooDB	Manually Annotated
Plant	Salix pulchra	FooDB	Manually Annotated
Plant	Castanea sativa	FooDB	Manually Annotated
Plant	Citrus maxima	FooDB	Manually Annotated
Plant	Annona muricata	FooDB	Manually Annotated
Plant	Fagus	FooDB	Manually Annotated
Plant	Cydonia oblonga	FooDB	Manually Annotated
Plant	Opuntia cochenillifera	FooDB	Manually Annotated
Plant	Vaccinium ovatum	FooDB	Manually Annotated
Plant	Cucurbita	FooDB	Manually Annotated
Plant	Cocos nucifera	FooDB	Manually Annotated
Plant	Thymus pulegioides	FooDB	Manually Annotated
Plant	Phaseolus coccineus	FooDB	Manually Annotated
Plant	Mespilus germanica	FooDB	Manually Annotated
Plant	Tamarindus indica	FooDB	Manually Annotated
Plant	Brassica rapa var. perviridis	FooDB	Manually Annotated
Plant	Cucurbita pepo var. cylindrica	FooDB	Manually Annotated
Plant	Mentha aquatica	FooDB	Manually Annotated
Plant	Salvia elegans	FooDB	Manually Annotated
Plant	Mentha	FooDB	Manually Annotated
Plant	Sagittaria latifolia	FooDB	Manually Annotated
Plant	Sambucus	FooDB	Manually Annotated
Plant	Syzygium cumini	FooDB	Manually Annotated
Plant	Pinus	FooDB	Manually Annotated
Plant	Psidium guajava	FooDB	Manually Annotated
Plant	Olea europaea	FooDB	Manually Annotated
Plant	Tilia tomentosa	FooDB	Manually Annotated
Plant	Typha angustifolia	FooDB	Manually Annotated
Plant	Empetrum nigrum	FooDB	Manually Annotated
Plant	Solanum tuberosum	FooDB	Manually Annotated
Plant	Myrica rubra	FooDB	Manually Annotated
Plant	Valerianella locusta	FooDB	Manually Annotated
Plant	Vaccinium angustifolium x vaccinium corymbosum	FooDB	Manually Annotated
Plant	Daucus carota	FooDB	Manually Annotated
Plant	Vaccinium vitis-idaea	FooDB	Manually Annotated
Plant	Sisymbrium	FooDB	Manually Annotated
Plant	Vanilla	FooDB	Manually Annotated
Plant	Carya	FooDB	Manually Annotated
Plant	Physalis philadelphica var. immaculata	FooDB	Manually Annotated
Plant	Borago officinalis	FooDB	Manually Annotated
Plant	Raphanus sativus	FooDB	Manually Annotated
Plant	Brassica oleracea l. var. capitata l. f. alba dc.	FooDB	Manually Annotated
Plant	Hyssopus officinalis	FooDB	Manually Annotated
Plant	Manihot esculenta	FooDB	Manually Annotated
Plant	Prunus dulcis	FooDB	Manually Annotated
Plant	Scorzonera hispanica	FooDB	Manually Annotated
Plant	Vigna radiata	FooDB	Manually Annotated
Plant	Beta vulgaris ssp. cicla	FooDB	Manually Annotated
Plant	Vigna unguiculata ssp. sesquipedalis	FooDB	Manually Annotated
Plant	Angelica keiskei	FooDB	Manually Annotated
Plant	Ipomoea aquatica	FooDB	Manually Annotated
Plant	Musa x paradisiaca	FooDB	Manually Annotated
Plant	Rubus spectabilis	FooDB	Manually Annotated
Plant	Cuminum cyminum	FooDB	Manually Annotated
Plant	Allium sativum	FooDB	Manually Annotated
Plant	Cantharellus cibarius	FooDB	Manually Annotated
Plant	Sinapis alba	FooDB	Manually Annotated
Plant	Fragaria x ananassa	FooDB	Manually Annotated
Plant	Arachis hypogaea	FooDB	Manually Annotated
Plant	Brassica ruvo	FooDB	Manually Annotated
Plant	Pyrus communis	FooDB	Manually Annotated
Plant	Rubus idaeus	FooDB	Manually Annotated
Plant	Morus nigra	FooDB	Manually Annotated
Plant	Apium graveolens var. secalinum	FooDB	Manually Annotated
Plant	Abelmoschus esculentus	FooDB	Manually Annotated
Plant	Moringa oleifera	FooDB	Manually Annotated
Plant	Solanum lycopersicum	FooDB	Manually Annotated
Plant	Pinus edulis	FooDB	Manually Annotated
Plant	Passiflora edulis	FooDB	Manually Annotated
Plant	Opuntia macrorhiza	FooDB	Manually Annotated
Plant	Vigna angularis	FooDB	Manually Annotated
Plant	Manilkara zapota	FooDB	Manually Annotated
Plant	Cucurbita pepo var. clypeata	FooDB	Manually Annotated
Plant	Mentha spicata	FooDB	Manually Annotated
Plant	Allium cepa	FooDB	Manually Annotated
Plant	Corylus	FooDB	Manually Annotated
Plant	Malus	FooDB	Manually Annotated
Plant	Sambucus nigra	FooDB	Manually Annotated
Plant	Helianthus annuus	FooDB	Manually Annotated
Plant	Juglans	FooDB	Manually Annotated
Plant	Mangifera indica	FooDB	Manually Annotated
Plant	Ribes nigrum	FooDB	Manually Annotated
Plant	Zingiber officinale	FooDB	Manually Annotated
Plant	Illicium verum	FooDB	Manually Annotated
Plant	Petroselinum crispum	FooDB	Manually Annotated
Plant		FooDB	Manually Annotated
Plant	Pisum sativum	FooDB	Manually Annotated
Plant	Chamaemelum nobile	FooDB	Manually Annotated
Plant	Laurus nobilis	FooDB	Manually Annotated
Plant	Auricularia auricula-judae	FooDB	Manually Annotated
Plant	Attalea speciosa	FooDB	Manually Annotated
Plant	Juglans ailanthifolia	FooDB	Manually Annotated
Plant	Melissa officinalis	FooDB	Manually Annotated
Plant	Hippophae rhamnoides	FooDB	Manually Annotated
Plant	Polygonum alpinum	FooDB	Manually Annotated
Plant	Brassica juncea	FooDB	Manually Annotated
Plant	Pediomelum esculentum	FooDB	Manually Annotated
Plant	Auricularia polytricha	FooDB	Manually Annotated
Plant	Camellia oleifera	FooDB	Manually Annotated
Plant	Vaccinium corymbosum	FooDB	Manually Annotated
Plant	Chrysanthemum coronarium	FooDB	Manually Annotated
Plant	Eleocharis dulcis	FooDB	Manually Annotated
Plant	Spinacia oleracea	FooDB	Manually Annotated
Plant	Carica papaya	FooDB	Manually Annotated
Plant	Thymus vulgaris	FooDB	Manually Annotated
Plant	Actinidia chinensis	FooDB	Manually Annotated
Plant	Rubus arcticus	FooDB	Manually Annotated
Plant	Pimenta dioica	FooDB	Manually Annotated
Plant	Medicago sativa	FooDB	Manually Annotated
Plant	Agaricus bisporus	FooDB	Manually Annotated
Plant	Cajanus cajan	FooDB	Manually Annotated
Plant	Vigna mungo	FooDB	Manually Annotated
Plant	Rumex articus	FooDB	Manually Annotated
Plant	Hibiscus sabdariffa	FooDB	Manually Annotated
Plant	Origanum majorana	FooDB	Manually Annotated
Plant	Armoracia rusticana	FooDB	Manually Annotated
Plant	Benincasa hispida	FooDB	Manually Annotated
Plant	Prunus persica	FooDB	Manually Annotated
Plant	Canarium ovatum	FooDB	Manually Annotated
Plant	Ribes aureum var. villosum	FooDB	Manually Annotated
Plant	Cucurbita pepo var. cylindrica	FooDB	Manually Annotated
Plant	Brassica oleracea var. gemmifera	FooDB	Manually Annotated
Plant	Foeniculum vulgare	FooDB	Manually Annotated
Plant	Arctium lappa	FooDB	Manually Annotated
Plant	Vaccinium macrocarpon	FooDB	Manually Annotated
Plant	Phoenix dactylifera	FooDB	Manually Annotated
Plant	Brassica oleracea var. gongylodes	FooDB	Manually Annotated
Plant	Juglans cinerea	FooDB	Manually Annotated
Plant	Eruca vesicaria ssp. sativa	FooDB	Manually Annotated
Plant		FooDB	Manually Annotated
Plant	Prunus cerasus	FooDB	Manually Annotated
Plant	Artocarpus altilis	FooDB	Manually Annotated
Plant	Metroxylon sagu	FooDB	Manually Annotated
Plant	Rosmarinus officinalis	FooDB	Manually Annotated
Plant	Vigna unguiculata	FooDB	Manually Annotated
Plant	Cynara scolymus	FooDB	Manually Annotated
Plant	Cyathea	FooDB	Manually Annotated
Plant	Vitis rotundifolia	FooDB	Manually Annotated
Plant	Citrus x paradisi	FooDB	Manually Annotated
Plant	Brosimum alicastrum	FooDB	Manually Annotated
Plant	Lentinus edodes	FooDB	Manually Annotated
Plant	Psidium cattleianum	FooDB	Manually Annotated
Plant	Ficus carica	FooDB	Manually Annotated
Plant	Castanea mollissima	FooDB	Manually Annotated
Plant	Morus	FooDB	Manually Annotated
Plant	Beta vulgaris var. rubra	FooDB	Manually Annotated
Plant	Lepidium sativum	FooDB	Manually Annotated
Plant	Vitis labrusca	FooDB	Manually Annotated
Plant	Phytolacca americana	FooDB	Manually Annotated
Plant	Grifola frondosa	FooDB	Manually Annotated
Plant	Helianthus tuberosus	FooDB	Manually Annotated
Plant	Tetragonia tetragonioides	FooDB	Manually Annotated
Plant	Artemisia vulgaris	FooDB	Manually Annotated
Plant	Cucumis metuliferus	FooDB	Manually Annotated
Plant	Myrica	FooDB	Manually Annotated
Plant	Nephelium lappaceum	FooDB	Manually Annotated
Plant	Castanea crenata	FooDB	Manually Annotated
Plant	Litchi chinensis	FooDB	Manually Annotated
Plant	Corylus avellana	FooDB	Manually Annotated
Plant	Vaccinium angustifolium	FooDB	Manually Annotated
Plant	Juglans regia	FooDB	Manually Annotated
Plant	Quercus	FooDB	Manually Annotated
Plant		FooDB	Manually Annotated
Plant	Trigonella foenum-graecum	FooDB	Manually Annotated
Plant	Malpighia emarginata	FooDB	Manually Annotated
Plant	Physalis	FooDB	Manually Annotated
Plant	Thelesperma	FooDB	Manually Annotated
Plant	Brassica oleracea var. sabauda	FooDB	Manually Annotated
Plant	Brassica napus	FooDB	Manually Annotated

Source Type	Activity	Data Source	Reference
General Exposome	Not Available	U.S. Environmental Protection Agency	CompTox
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	10.6	7.2	uM	Adult (>18 years old)	Male	Essential hypertension	HMDB	18633173
Human Blood	Detected and Quantified	11.9	7.6	uM	Adult (>18 years old)	Female	Essential hypertension	HMDB	18633173
Human Blood	Detected and Quantified	11.0	7.3	uM	Adult (>18 years old)	Both	Hypertension	HMDB	18633173
Human Blood	Detected and Quantified	13.9	17.9	uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	HMDB	27329611
Human Blood	Detected and Quantified	63.151	36.700	uM	Adult (>18 years old)	Both	Depression	HMDB	21185973
Human Blood	Detected and Quantified	0.00039		uM	Adult (>18 years old)	Both	Normal	HMDB	11593343
Human Blood	Detected and Quantified	0.00052		uM	Adult (>18 years old)	Both	Normal	HMDB	11593343
Human Blood	Detected and Quantified	0.00058		uM	Adult (>18 years old)	Both	Normal	HMDB	11593343
Human Blood	Detected and Quantified	0.00073		uM	Adult (>18 years old)	Both	Normal	HMDB	11593343
Human Blood	Detected and Quantified	0.401	0.068	uM	Adult (>18 years old)	Both	Normal	HMDB	18953024
Human Blood	Detected and Quantified	0.401	0.068	uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	0.435	0.010	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	1.09	0.72	uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	10.8	6.2	uM	Adult (>18 years old)	Female	Normal	HMDB	18633173
Human Blood	Detected and Quantified	11.0	8.3	uM	Adult (>18 years old)	Both	Normal	HMDB	18633173
Human Blood	Detected and Quantified	11.1	9.5	uM	Adult (>18 years old)	Male	Normal	HMDB	18633173
Human Blood	Detected and Quantified	19.838	9.919	uM	Adult (>18 years old)	Male	Normal	HMDB	17069347
Human Blood	Detected and Quantified	200	110	uM	Adult (>18 years old)	Male	Normal	HMDB	14608088
Human Blood	Detected and Quantified	2100.0	990.0	uM	Adult (>18 years old)	Male	Normal	HMDB	18203893
Human Blood	Detected and Quantified	23.144	9.919	uM	Adult (>18 years old)	Male	Normal	HMDB	17069347
Human Blood	Detected and Quantified	260	110	uM	Adult (>18 years old)	Female	Normal	HMDB	14608088
Human Blood	Detected and Quantified	270	160	uM	Adult (>18 years old)	Male	Normal	HMDB	18203893
Human Blood	Detected and Quantified	33.0632	9.919	uM	Adult (>18 years old)	Male	Normal	HMDB	17069347
Human Blood	Detected and Quantified	36.370	16.532	uM	Adult (>18 years old)	Male	Normal	HMDB	17069347
Human Blood	Detected and Quantified	37.890	24.764	uM	Adult (>18 years old)	Both	Normal	HMDB	17313719
Human Blood	Detected and Quantified	66.457	42.321	uM	Adult (>18 years old)	Both	Normal	HMDB	21185973
Human Blood	Detected and Quantified	67.6	50.2	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	27329611
Human Blood	Detected and Quantified	70.425	48.603	uM	Adult (>18 years old)	Both	Normal	HMDB	21185973
Human Blood	Detected and Quantified	79.649	51.182	uM	Adult (>18 years old)	Female	Normal	HMDB	9368807
Human Adipose tissue	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Erythrocyte	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Leukocyte	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Sweat	Detected but not Quantified				Adult	Both	Normal	HMDB	26755145
Human Blood	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	24740205
Human Blood	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	24801555
Human Blood	Detected but not Quantified				Adult (>18 years old)	Female	Normal	HMDB	27355821
Human Blood	Detected but not Quantified				Adult (>18 years old)	Female	Normal	HMDB	27355821
Human Blood	Detected but not Quantified				Adult (>18 years old)	Female	Normal	HMDB	27355821
Human Blood	Detected but not Quantified				Adult (>18 years old)	Female	Normal	HMDB	27355821
Human Blood	Detected but not Quantified				Adult (>18 years old)	Female	Normal	HMDB	27355821
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0001999

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.1016/0005-2760(92)90270-6. [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. doi: 10.1111/j.1365-2796.1989.tb01452.x. [PubMed:2539831 ]
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. doi: 10.1002/art.1780310502. [PubMed:2837251 ]
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. doi: 10.1016/0049-3848(86)90248-3. [PubMed:3010490 ]
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 ]
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. doi: 10.1006/clin.1996.0072. [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. doi: 10.1016/0378-4347(95)00445-9. [PubMed:8704924 ]
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. doi: 10.1016/s0952-3278(96)90093-9. [PubMed:8931114 ]
Hereliuk VI: [The role of arachidonic and eicosapentaenoic acid lipoxygenase products in the pathogenesis of generalized parodontosis]. Fiziol Zh (1994). 2000;46(6):112-5. [PubMed:11424554 ]
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. doi: 10.1006/jsre.2002.6496. [PubMed:12384078 ]
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. doi: 10.1016/s0021-9150(02)00307-6. [PubMed:12482554 ]
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. doi: 10.1093/ajcn/77.1.226. [PubMed:12499346 ]
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. doi: 10.1111/j.1365-2222.2004.02028.x. [PubMed:15298564 ]
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. doi: 10.1194/jlr.M500105-JLR200. Epub 2005 Jun 1. [PubMed:15930517 ]
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. doi: 10.1194/jlr.M500300-JLR200. 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. doi: 10.1194/jlr.M500420-JLR200. Epub 2006 Feb 7. [PubMed:16467281 ]
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Showing metabocard for Eicosapentaenoic acid (MMDBc0000579)

MOL for #<Metabolite:0x00007fdb71921f18>

3D MOL for #<Metabolite:0x00007fdb71921f18>

3D SDF for #<Metabolite:0x00007fdb71921f18>

3D-SDF for #<Metabolite:0x00007fdb71921f18>

PDB for #<Metabolite:0x00007fdb71921f18>

3D PDB for #<Metabolite:0x00007fdb71921f18>

SMILES for #<Metabolite:0x00007fdb71921f18>

INCHI for #<Metabolite:0x00007fdb71921f18>

Structure for #<Metabolite:0x00007fdb71921f18>

3D Structure for #<Metabolite:0x00007fdb71921f18>