MiMeDB: Showing metabocard for Eicosapentaenoic acid (MMDBc0000579)

Microbial

Human

Plant

Animal

Pharmaceutical

Xenobiotic

Record Information

Version

2.0

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

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (void)	2025-10-23	406.2
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	38.9
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	902.0
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	638.3
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	1247.5
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	612.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	3225.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	90.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	700.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	986.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	599.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	513.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	261.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	8.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	458.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	754.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	575.9
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1956.2
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	2436.1

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Eicosapentaenoic acid_TMS_1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2130.54
Gas Chromatography	Eicosapentaenoic acid_TMS_1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	standard polar	2025-10-23	2638.34

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0036243	PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z))	Eicosapentaenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036244	PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))	Eicosapentaenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036245	PC(18:0/20:5(5Z,8Z,11Z,14Z,17Z))	Eicosapentaenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036246	PC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))	Eicosapentaenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036247	PC(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))	Eicosapentaenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036248	PC(20:0/20:5(5Z,8Z,11Z,14Z,17Z))	Eicosapentaenoic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036717	PC(20:5(5Z,8Z,11Z,14Z,17Z)/16:0)	Eicosapentaenoic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036718	PC(20:5(5Z,8Z,11Z,14Z,17Z)/16:1(9Z))	Eicosapentaenoic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036719	PC(20:5(5Z,8Z,11Z,14Z,17Z)/18:1(11Z))	Eicosapentaenoic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036720	PC(20:5(5Z,8Z,11Z,14Z,17Z)/18:1(9Z))	Eicosapentaenoic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0036721	PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:0)	Eicosapentaenoic acid	cGAMP-activated phospholipase	Hydrolysis	RHEA	34755880
MMDBr0038703	Eicosapentaenoic acid	(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA	Long-chain-fatty-acid--CoA ligase 1	Hydrolysis; Ligation	RHEA	34755880
MMDBr0038951	Eicosapentaenoic acid	N-(Eicosapentaenoyl)-4R-hydroxysphinganine	Alkaline ceramidase YPC1	Hydrolysis	RHEA	34755880

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/Eubacteria	Verrucomicrobia	1	Human feces; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Bacteroidetes	2	Human feces; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Firmicutes	4	Human feces; Human ; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
General Exposome	U.S. Environmental Protection Agency	CompTox
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	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

CMMC Knowledgebase

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 ]
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Showing metabocard for Eicosapentaenoic acid (MMDBc0000579)

MOL for #<Metabolite:0x00005624ca1e6190>

3D MOL for #<Metabolite:0x00005624ca1e6190>

3D SDF for #<Metabolite:0x00005624ca1e6190>

3D-SDF for #<Metabolite:0x00005624ca1e6190>

PDB for #<Metabolite:0x00005624ca1e6190>

3D PDB for #<Metabolite:0x00005624ca1e6190>

SMILES for #<Metabolite:0x00005624ca1e6190>

INCHI for #<Metabolite:0x00005624ca1e6190>

Structure for #<Metabolite:0x00005624ca1e6190>

3D Structure for #<Metabolite:0x00005624ca1e6190>