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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (52) Show 52 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:05 UTC

HMDB ID

HMDB0000673

Secondary Accession Numbers

HMDB00673

Metabolite Identification

Common Name

Linoleic acid

Description

Linoleic acid is a doubly unsaturated fatty acid, also known as an omega-6 fatty acid, occurring widely in plant glycosides. In this particular polyunsaturated fatty acid (PUFA), the first double bond is located between the sixth and seventh carbon atom from the methyl end of the fatty acid (n-6). Linoleic acid is an essential fatty acid in human nutrition because it cannot be synthesized by humans. It is used in the biosynthesis of prostaglandins (via arachidonic acid) and cell membranes (From Stedman, 26th ed). Linoleic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.

Structure

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

HMDB0000673
     RDKit          3D
Linoleic acid
 52 51  0  0  0  0  0  0  0  0999 V2000
    4.1205   -1.5407    3.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9996   -2.0535    1.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4852   -0.9837    0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4171    0.2154    0.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8124    1.2468   -0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7357    0.6289   -1.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6226    0.4534   -2.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3394    0.8808   -1.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7010    1.8815   -2.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4728    1.6798   -3.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3213    0.5117   -2.8829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6655    0.9909   -2.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5750    1.6561   -0.9938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0592    0.8085    0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8813   -0.4258    0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2917   -0.0538    0.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1710   -1.2387    1.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6605   -2.0132    2.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2785   -3.0882    2.5090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5702   -1.6864    2.9881 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2790   -0.9082    3.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2156   -2.3811    3.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1094   -0.9946    3.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2576   -2.8739    1.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9503   -2.4326    1.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4699   -0.6521    0.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853   -1.4259   -0.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4382    0.6549    1.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3953   -0.1299    0.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6152    2.0565   -0.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9670    1.6498    0.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7016    0.2943   -1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5737   -0.0249   -3.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7238   -0.0651   -1.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2978    1.2820   -0.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2485    2.8388   -2.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8591    2.5074   -3.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315    0.0627   -3.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0091   -0.2865   -2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0619    1.7294   -3.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3432    0.1065   -2.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5859    2.0313   -0.7050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9293    2.5717   -1.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0284    0.4964   -0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0981    1.4139    1.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3434   -1.0003    1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9407   -1.0936   -0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3028    0.6580    1.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7328    0.5118   -0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2155   -0.9204    1.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2651   -1.8444    0.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6681   -1.7016    3.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  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  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 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
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 20 52  1  0
M  END


  Mrv1652309272007402D          

 20 19  0  0  0  0            999 V2000
 9997.2377 9998.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9526 9998.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6676 9998.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.4938 9998.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.2075 9998.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.9231 9998.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7481 9998.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.4638 9998.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.1774 9998.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.8930 9998.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.6087 9998.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.3222 9998.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5229 9998.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8081 9998.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0933 9998.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3782 9998.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6633 9998.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9485 9998.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.2337 9998.1743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9485 9999.4117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000673

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-

> <INCHI_KEY>
OYHQOLUKZRVURQ-HZJYTTRNSA-N

> <FORMULA>
C18H32O2

> <MOLECULAR_WEIGHT>
280.4455

> <EXACT_MASS>
280.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
35.86492653946456

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9Z,12Z)-octadeca-9,12-dienoic acid

> <ALOGPS_LOGP>
7.06

> <JCHEM_LOGP>
6.421876794333333

> <ALOGPS_LOGS>
-6.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167283903808

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
88.5188

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.54e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
linoleic

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000673
     RDKit          3D
Linoleic acid
 52 51  0  0  0  0  0  0  0  0999 V2000
    4.1205   -1.5407    3.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9996   -2.0535    1.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4852   -0.9837    0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4171    0.2154    0.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8124    1.2468   -0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7357    0.6289   -1.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6226    0.4534   -2.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3394    0.8808   -1.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7010    1.8815   -2.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4728    1.6798   -3.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3213    0.5117   -2.8829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6655    0.9909   -2.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5750    1.6561   -0.9938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0592    0.8085    0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8813   -0.4258    0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2917   -0.0538    0.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1710   -1.2387    1.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6605   -2.0132    2.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2785   -3.0882    2.5090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5702   -1.6864    2.9881 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2790   -0.9082    3.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2156   -2.3811    3.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1094   -0.9946    3.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2576   -2.8739    1.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9503   -2.4326    1.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4699   -0.6521    0.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853   -1.4259   -0.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4382    0.6549    1.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3953   -0.1299    0.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6152    2.0565   -0.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9670    1.6498    0.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7016    0.2943   -1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5737   -0.0249   -3.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7238   -0.0651   -1.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2978    1.2820   -0.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2485    2.8388   -2.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8591    2.5074   -3.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315    0.0627   -3.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0091   -0.2865   -2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0619    1.7294   -3.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3432    0.1065   -2.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5859    2.0313   -0.7050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9293    2.5717   -1.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0284    0.4964   -0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0981    1.4139    1.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3434   -1.0003    1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9407   -1.0936   -0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3028    0.6580    1.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7328    0.5118   -0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2155   -0.9204    1.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2651   -1.8444    0.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6681   -1.7016    3.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  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  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 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
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 20 52  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8661.5108664.027   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.8458663.259   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8664.1808664.027   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8665.7228664.027   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8667.0548663.259   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8668.3908664.027   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8669.9308664.027   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8671.2668663.259   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8672.5988664.027   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8673.9348663.259   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8675.2708664.027   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8676.6028663.259   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8660.1768663.259   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8658.8428664.027   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8657.5078663.259   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8656.1738664.027   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8654.8388663.259   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8653.5048664.027   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8652.1708663.259   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0    8653.5048665.568   0.000  0.00  0.00           O+0
CONECT    1    2   13                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    1   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    HMDB0000673
HETATM    1  C1  UNL     1       4.121  -1.541   3.109  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.000  -2.054   1.689  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.485  -0.984   0.755  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.417   0.215   0.737  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.812   1.247  -0.237  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.736   0.629  -1.528  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.623   0.453  -2.174  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.339   0.881  -1.621  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.701   1.882  -2.515  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.473   1.680  -3.052  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.321   0.512  -2.883  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.665   0.991  -2.316  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.575   1.656  -0.994  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.059   0.809   0.123  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.881  -0.426   0.401  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.292  -0.054   0.777  1.00  0.00           C  
HETATM   17  C17 UNL     1      -5.171  -1.239   1.077  1.00  0.00           C  
HETATM   18  C18 UNL     1      -4.660  -2.013   2.210  1.00  0.00           C  
HETATM   19  O1  UNL     1      -5.278  -3.088   2.509  1.00  0.00           O  
HETATM   20  O2  UNL     1      -3.570  -1.686   2.988  1.00  0.00           O  
HETATM   21  H1  UNL     1       3.279  -0.908   3.398  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.216  -2.381   3.823  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.109  -0.995   3.145  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.258  -2.874   1.688  1.00  0.00           H  
HETATM   25  H5  UNL     1       4.950  -2.433   1.320  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.470  -0.652   0.965  1.00  0.00           H  
HETATM   27  H7  UNL     1       3.485  -1.426  -0.267  1.00  0.00           H  
HETATM   28  H8  UNL     1       4.438   0.655   1.739  1.00  0.00           H  
HETATM   29  H9  UNL     1       5.395  -0.130   0.385  1.00  0.00           H  
HETATM   30  H10 UNL     1       4.615   2.056  -0.301  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.967   1.650   0.268  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.702   0.294  -1.969  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.574  -0.025  -3.173  1.00  0.00           H  
HETATM   34  H14 UNL     1       0.724  -0.065  -1.570  1.00  0.00           H  
HETATM   35  H15 UNL     1       1.298   1.282  -0.624  1.00  0.00           H  
HETATM   36  H16 UNL     1       1.249   2.839  -2.731  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.859   2.507  -3.717  1.00  0.00           H  
HETATM   38  H18 UNL     1      -1.631   0.063  -3.887  1.00  0.00           H  
HETATM   39  H19 UNL     1      -1.009  -0.287  -2.234  1.00  0.00           H  
HETATM   40  H20 UNL     1      -3.062   1.729  -3.056  1.00  0.00           H  
HETATM   41  H21 UNL     1      -3.343   0.106  -2.285  1.00  0.00           H  
HETATM   42  H22 UNL     1      -3.586   2.031  -0.705  1.00  0.00           H  
HETATM   43  H23 UNL     1      -1.929   2.572  -1.074  1.00  0.00           H  
HETATM   44  H24 UNL     1      -1.028   0.496  -0.075  1.00  0.00           H  
HETATM   45  H25 UNL     1      -2.098   1.414   1.057  1.00  0.00           H  
HETATM   46  H26 UNL     1      -2.343  -1.000   1.177  1.00  0.00           H  
HETATM   47  H27 UNL     1      -2.941  -1.094  -0.487  1.00  0.00           H  
HETATM   48  H28 UNL     1      -4.303   0.658   1.630  1.00  0.00           H  
HETATM   49  H29 UNL     1      -4.733   0.512  -0.088  1.00  0.00           H  
HETATM   50  H30 UNL     1      -6.215  -0.920   1.314  1.00  0.00           H  
HETATM   51  H31 UNL     1      -5.265  -1.844   0.146  1.00  0.00           H  
HETATM   52  H32 UNL     1      -3.668  -1.702   3.983  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5   28   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   40   41
CONECT   13   14   42   43
CONECT   14   15   44   45
CONECT   15   16   46   47
CONECT   16   17   48   49
CONECT   17   18   50   51
CONECT   18   19   19   20
CONECT   20   52
END

HMDB0000673
     RDKit          3D
Linoleic acid
 52 51  0  0  0  0  0  0  0  0999 V2000
    4.1205   -1.5407    3.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9996   -2.0535    1.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4852   -0.9837    0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4171    0.2154    0.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8124    1.2468   -0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7357    0.6289   -1.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6226    0.4534   -2.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3394    0.8808   -1.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7010    1.8815   -2.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4728    1.6798   -3.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3213    0.5117   -2.8829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6655    0.9909   -2.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5750    1.6561   -0.9938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0592    0.8085    0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8813   -0.4258    0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2917   -0.0538    0.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1710   -1.2387    1.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6605   -2.0132    2.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2785   -3.0882    2.5090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5702   -1.6864    2.9881 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2790   -0.9082    3.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2156   -2.3811    3.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1094   -0.9946    3.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2576   -2.8739    1.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9503   -2.4326    1.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4699   -0.6521    0.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853   -1.4259   -0.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4382    0.6549    1.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3953   -0.1299    0.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6152    2.0565   -0.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9670    1.6498    0.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7016    0.2943   -1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5737   -0.0249   -3.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7238   -0.0651   -1.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2978    1.2820   -0.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2485    2.8388   -2.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8591    2.5074   -3.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315    0.0627   -3.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0091   -0.2865   -2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0619    1.7294   -3.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3432    0.1065   -2.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5859    2.0313   -0.7050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9293    2.5717   -1.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0284    0.4964   -0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0981    1.4139    1.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3434   -1.0003    1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9407   -1.0936   -0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3028    0.6580    1.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7328    0.5118   -0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2155   -0.9204    1.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2651   -1.8444    0.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6681   -1.7016    3.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  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  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 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
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 20 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(9Z,12Z)-Octadecadienoic acid	ChEBI
(Z,Z)-9,12-Octadecadienoic acid	ChEBI
9-cis,12-cis-Octadecadienoic acid	ChEBI
9Z,12Z-Octadecadienoic acid	ChEBI
Acide cis-linoleique	ChEBI
Acide linoleique	ChEBI
Acido linoleico	ChEBI
all-cis-9,12-Octadecadienoic acid	ChEBI
C18:2 9C, 12C Omega6 todos cis-9,12-octadienoico	ChEBI
C18:2, N-6,9 all-cis	ChEBI
cis,cis-9,12-Octadecadienoic acid	ChEBI
cis,cis-Linoleic acid	ChEBI
cis-Delta(9,12)-Octadecadienoic acid	ChEBI
LA	ChEBI
Linolic acid	ChEBI
9-cis,12-cis-Octadecadienoate	Kegg
(9Z,12Z)-Octadecadienoate	Generator
(Z,Z)-9,12-Octadecadienoate	Generator
9Z,12Z-Octadecadienoate	Generator
all-cis-9,12-Octadecadienoate	Generator
cis,cis-9,12-Octadecadienoate	Generator
cis,cis-Linoleate	Generator
cis-delta(9,12)-Octadecadienoate	Generator
cis-Δ(9,12)-octadecadienoate	Generator
cis-Δ(9,12)-octadecadienoic acid	Generator
Linolate	Generator
Linoleate	Generator
(9Z,12Z)-9,12-Octadecadienoate	HMDB
(9Z,12Z)-9,12-Octadecadienoic acid	HMDB
9-cis,12-cis-Linoleate	HMDB
9-cis,12-cis-Linoleic acid	HMDB
9Z,12Z-Linoleate	HMDB
9Z,12Z-Linoleic acid	HMDB
cis-9,cis-12-Octadecadienoate	HMDB
cis-9,cis-12-Octadecadienoic acid	HMDB
cis-D9,12-Octadecadienoate	HMDB
cis-D9,12-Octadecadienoic acid	HMDB
Emersol 315	HMDB
Extra linoleic 90	HMDB
Polylin 515	HMDB
Unifac 6550	HMDB
Acid, 9,12-octadecadienoic	HMDB
Linoelaidic acid	HMDB
Linoleic acid, (e,e)-isomer	HMDB
Linoleic acid, (Z,Z)-isomer	HMDB
Linoleic acid, (Z,Z)-isomer, 14C-labeled	HMDB
Linoleic acid, ammonium salt, (Z,Z)-isomer	HMDB
Linoleic acid, potassium salt, (Z,Z)-isomer	HMDB
9 trans,12 trans Octadecadienoic acid	HMDB
9-trans,12-trans-Octadecadienoic acid	HMDB
Linoleic acid, sodium salt, (e,e)-isomer	HMDB
Linoleic acid, sodium salt, (Z,Z)-isomer	HMDB
trans,trans-9,12-Octadecadienoic acid	HMDB
9,12-Octadecadienoic acid	HMDB
Linoelaidic acid, (e,Z)-isomer	HMDB
Linoleic acid, calcium salt, (Z,Z)-isomer	HMDB
Linolelaidic acid	HMDB
9,12 Octadecadienoic acid	HMDB
Linoleic acid, (Z,e)-isomer	HMDB
FA(18:2(9Z,12Z))	HMDB

Chemical Formula

C₁₈H₃₂O₂

Average Molecular Weight

280.4455

Monoisotopic Molecular Weight

280.240230268

IUPAC Name

(9Z,12Z)-octadeca-9,12-dienoic acid

Traditional Name

linoleic

CAS Registry Number

60-33-3

SMILES

CCCCC\C=C/C\C=C/CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-

InChI Key

OYHQOLUKZRVURQ-HZJYTTRNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
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-6 fatty acid (CHEBI:17351 )
octadecadienoic acid (CHEBI:17351 )
Unsaturated fatty acids (C01595 )
Polyunsaturated fatty acids (C01595 )
Unsaturated fatty acids (LMFA01030120 )

Ontology

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-8.5 °C	Not Available
Boiling Point	229.00 to 230.00 °C. @ 16.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.038 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	7.05	SANGSTER (1993)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	173.244	30932474
[M-H]-	Not Available	174.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000206

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00015 g/L	ALOGPS
logP	7.06	ALOGPS
logP	6.42	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	88.52 m³·mol⁻¹	ChemAxon
Polarizability	35.86 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	178.546	31661259
DarkChem	[M-H]-	177.761	31661259
AllCCS	[M+H]+	177.38	32859911
AllCCS	[M-H]-	178.476	32859911
DeepCCS	[M+H]+	178.248	30932474
DeepCCS	[M-H]-	174.581	30932474
DeepCCS	[M-2H]-	210.773	30932474
DeepCCS	[M+Na]+	187.063	30932474
AllCCS	[M+H]+	177.4	32859911
AllCCS	[M+H-H2O]+	174.3	32859911
AllCCS	[M+NH4]+	180.2	32859911
AllCCS	[M+Na]+	181.0	32859911
AllCCS	[M-H]-	178.5	32859911
AllCCS	[M+Na-2H]-	180.1	32859911
AllCCS	[M+HCOO]-	181.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Linoleic acid	CCCCC\C=C/C\C=C/CCCCCCCC(O)=O	3266.3	Standard polar	33892256
Linoleic acid	CCCCC\C=C/C\C=C/CCCCCCCC(O)=O	2067.0	Standard non polar	33892256
Linoleic acid	CCCCC\C=C/C\C=C/CCCCCCCC(O)=O	2140.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Linoleic acid,1TMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)O[Si](C)(C)C	2216.7	Semi standard non polar	33892256
Linoleic acid,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2459.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Linoleic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-000t-7900000000-b6ee03c4800464c37471	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Linoleic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-00vi-9300000000-c92dac639ced59eb5dbe	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Linoleic acid GC-MS (1 TMS)	splash10-003s-9700000000-77e67d7b1a161e6ecfa6	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Linoleic acid GC-EI-TOF (Non-derivatized)	splash10-000t-7900000000-b6ee03c4800464c37471	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Linoleic acid GC-EI-TOF (Non-derivatized)	splash10-00vi-9300000000-c92dac639ced59eb5dbe	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Linoleic acid GC-MS (Non-derivatized)	splash10-003s-9700000000-77e67d7b1a161e6ecfa6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Linoleic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9750000000-50d69948d56dd2ba6e42	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Linoleic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0079-9631000000-cc93c24bbf14d81ae9b6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Linoleic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Linoleic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-015a-9200000000-a193c27810bedf93c498	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linoleic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0f89-0190000000-2be9501b1d4a9fcbd1c0	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linoleic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0uk9-0790000000-7f6e35a591f977bc488e	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linoleic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0udi-0090000000-c56edc2bbf9d6752aec5	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linoleic acid FAB-EBEB (JMS-HX/HX 110A, JEOL) , Negative-QTOF	splash10-004i-0090000000-baf4579e26c6b393d391	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linoleic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-004i-0090000000-815c1682b2c59ba96f10	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linoleic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-004i-0090000000-3406b2b2d5756807e1cd	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linoleic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-004i-0090000000-2fb4975278fa4d118f43	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linoleic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0a6r-9380000000-37f833673c248405c8ef	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linoleic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-0a4i-9200000000-7d34ed5900a17ffe3f9b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linoleic acid ESI-TOF 10V, Negative-QTOF	splash10-004i-0090010000-f8df6099e003402f2566	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linoleic acid ESI-TOF , Negative-QTOF	splash10-004i-0091021000-0e44779958d5744d873b	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linoleic acid ESI-TOF 10V, Negative-QTOF	splash10-004i-0091021000-0e44779958d5744d873b	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linoleic acid ESI-TOF 20V, Negative-QTOF	splash10-004i-0091021000-0e44779958d5744d873b	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linoleic acid ESI-TOF 30V, Negative-QTOF	splash10-004i-0091021000-0e44779958d5744d873b	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linoleic acid ESI-TOF 10V, Negative-QTOF	splash10-004i-0090010000-f8df6099e003402f2566	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linoleic acid ESI-TOF , Negative-QTOF	splash10-004i-0091021000-0e44779958d5744d873b	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linoleic acid ESI-TOF 10V, Negative-QTOF	splash10-004i-0090000000-adbf36f0a17c33ac33f8	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linoleic acid ESI-TOF 20V, Negative-QTOF	splash10-004i-0090000000-2747c83af78732eb6e16	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linoleic acid ESI-TOF 30V, Negative-QTOF	splash10-004i-0090000000-a0415b1cb63b4562b40e	2017-09-12	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleic acid 10V, Positive-QTOF	splash10-03di-0090000000-8bdf8d54a29f73494242	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleic acid 20V, Positive-QTOF	splash10-0239-4590000000-e5ee57553b064eae2efe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleic acid 40V, Positive-QTOF	splash10-00rf-9830000000-b26ba057a2b4d135b478	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleic acid 10V, Negative-QTOF	splash10-004i-0090000000-f1e9e4b543f7d4f48bf8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleic acid 20V, Negative-QTOF	splash10-01ti-0090000000-665523c6142ff4e39c96	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleic acid 40V, Negative-QTOF	splash10-0a4l-9240000000-dca36a25ad7519d500c3	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Adipose Tissue
Epidermis
Erythrocyte
Fibroblasts
Intestine
Kidney
Neuron
Placenta
Platelet
Prostate
Skeletal Muscle
Spleen

Pathways

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

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	23.39 +/- 2.75 uM	Adult (>18 years old)	Female	Normal	14634727	details
Blood	Detected and Quantified	110 (42-370) uM	Adult (>18 years old)	Both	Normal	8412012	details
Blood	Detected and Quantified	83.8 +/- 38 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	193.7 +/- 72.0 uM	Adult (>18 years old)	Both	Normal	18633173	details
Blood	Detected and Quantified	264 +/- 17.0 uM	Adult (>18 years old)	Both	Normal	25004141	details
Blood	Detected and Quantified	183.7 +/- 69.9 uM	Adult (>18 years old)	Male	Normal	18633173	details
Blood	Detected and Quantified	207.9 +/- 73.0 uM	Adult (>18 years old)	Female	Normal	18633173	details
Blood	Detected and Quantified	734.546 +/- 92.710 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	798.729 +/- 99.841 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	927.0964 +/- 110.538 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	930.662 +/- 89.144 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	61 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	17.7 +/- 4.7 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	14.733 +/- 4.331 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	74 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	134 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	192 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	246 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	291 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	308 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	311 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	11.8-21.6 uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	525 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	563 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	618 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	1021.482 +/- 224.215 uM	Adult (>18 years old)	Both	Normal	17313719	details
Blood	Detected and Quantified	1065.519 +/- 201.893 uM	Adult (>18 years old)	Female	Normal	9368807	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22007635	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	22061338	details
Blood	Detected and Quantified	15.2 +/- 0.437 uM	Adult (>18 years old)	Both	Normal	20671299	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	11.0 +/- 3.0 uM	Adult (>18 years old)	Not Specified	Normal	8412012	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23940645	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24029555	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23384618	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24424155	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28842642	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28587349	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.05 +/- 0.05 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	1.19 +/- 0.61 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	14643447	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	22.61 +/- 2.80 uM	Adult (>18 years old)	Female	Gestational diabetes mellitus (GDM)	14634727	details
Blood	Detected and Quantified	886.0 +/- 626.6 uM	Adult (>18 years old)	Both	Cirrhosis	3101533	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Oesophageal cancer	22291914	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Lung cancer	25961003	details
Blood	Detected and Quantified	175.9 +/- 65.0 uM	Adult (>18 years old)	Both	Hypertension	18633173	details
Blood	Detected and Quantified	159 +/- 12.0 uM	Adult (>18 years old)	Both	Schizophrenia	25004141	details
Blood	Detected and Quantified	2796.7 +/- 493.9 uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	27329611	details
Blood	Detected and Quantified	167.0 +/- 63.8 uM	Adult (>18 years old)	Male	Essential hypertension	18633173	details
Blood	Detected and Quantified	195.2 +/- 64.4 uM	Adult (>18 years old)	Female	Essential hypertension	18633173	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22007635	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Breast cancer	22061338	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	23940645	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	CCD	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ileal Crohn's disease	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	liver cirrhosis	23384618	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Not Specified	Premature neonates	23210743	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	28587349	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	24424155	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	28842642	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Interstitial cystitis	27188581	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	23940645	details
Urine	Detected and Quantified	0.18 +/- 0.45 umol/mmol creatinine	Adult (>18 years old)	Female	Thyroid cancer	14643447	details

Associated Disorders and Diseases

Disease References

Gestational diabetes
Min Y, Ghebremeskel K, Lowy C, Thomas B, Crawford MA: Adverse effect of obesity on red cell membrane arachidonic and docosahexaenoic acids in gestational diabetes. Diabetologia. 2004 Jan;47(1):75-81. Epub 2003 Nov 22. [PubMed:14634727 ]
Cirrhosis
Szebeni J, Eskelson C, Sampliner R, Hartmann B, Griffin J, Dormandy T, Watson RR: Plasma fatty acid pattern including diene-conjugated linoleic acid in ethanol users and patients with ethanol-related liver disease. Alcohol Clin Exp Res. 1986 Dec;10(6):647-50. [PubMed:3101533 ] Huang HJ, Zhang AY, Cao HC, Lu HF, Wang BH, Xie Q, Xu W, Li LJ: Metabolomic analyses of faeces reveals malabsorption in cirrhotic patients. Dig Liver Dis. 2013 Aug;45(8):677-82. doi: 10.1016/j.dld.2013.01.001. Epub 2013 Feb 4. [PubMed:23384618 ]
Hypertension
Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32. doi: 10.1291/hypres.31.623. [PubMed:18633173 ]
Essential hypertension
Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32. doi: 10.1291/hypres.31.623. [PubMed:18633173 ]
Perillyl alcohol administration for cancer treatment
Lv W, Yang T: Identification of possible biomarkers for breast cancer from free fatty acid profiles determined by GC-MS and multivariate statistical analysis. Clin Biochem. 2012 Jan;45(1-2):127-33. doi: 10.1016/j.clinbiochem.2011.10.011. Epub 2011 Oct 26. [PubMed:22061338 ]
Lung Cancer
Chen Y, Ma Z, Min L, Li H, Wang B, Zhong J, Dai L: Biomarker identification and pathway analysis by serum metabolomics of lung cancer. Biomed Res Int. 2015;2015:183624. doi: 10.1155/2015/183624. Epub 2015 Apr 16. [PubMed:25961003 ]
Schizophrenia
Fukushima T, Iizuka H, Yokota A, Suzuki T, Ohno C, Kono Y, Nishikiori M, Seki A, Ichiba H, Watanabe Y, Hongo S, Utsunomiya M, Nakatani M, Sadamoto K, Yoshio T: Quantitative analyses of schizophrenia-associated metabolites in serum: serum D-lactate levels are negatively correlated with gamma-glutamylcysteine in medicated schizophrenia patients. PLoS One. 2014 Jul 8;9(7):e101652. doi: 10.1371/journal.pone.0101652. eCollection 2014. [PubMed:25004141 ] Xuan J, Pan G, Qiu Y, Yang L, Su M, Liu Y, Chen J, Feng G, Fang Y, Jia W, Xing Q, He L: Metabolomic profiling to identify potential serum biomarkers for schizophrenia and risperidone action. J Proteome Res. 2011 Dec 2;10(12):5433-43. doi: 10.1021/pr2006796. Epub 2011 Nov 8. [PubMed:22007635 ]
Isovaleric acidemia
Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Colorectal cancer
Weir TL, Manter DK, Sheflin AM, Barnett BA, Heuberger AL, Ryan EP: Stool microbiome and metabolome differences between colorectal cancer patients and healthy adults. PLoS One. 2013 Aug 6;8(8):e70803. doi: 10.1371/journal.pone.0070803. Print 2013. [PubMed:23940645 ] Phua LC, Chue XP, Koh PK, Cheah PY, Ho HK, Chan EC: Non-invasive fecal metabonomic detection of colorectal cancer. Cancer Biol Ther. 2014 Apr;15(4):389-97. doi: 10.4161/cbt.27625. Epub 2014 Jan 14. [PubMed:24424155 ] Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ] Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ] Wang X, Wang J, Rao B, Deng L: Gut flora profiling and fecal metabolite composition of colorectal cancer patients and healthy individuals. Exp Ther Med. 2017 Jun;13(6):2848-2854. doi: 10.3892/etm.2017.4367. Epub 2017 Apr 20. [PubMed:28587349 ]
Bladder infections
Braundmeier-Fleming A, Russell NT, Yang W, Nas MY, Yaggie RE, Berry M, Bachrach L, Flury SC, Marko DS, Bushell CB, Welge ME, White BA, Schaeffer AJ, Klumpp DJ: Stool-based biomarkers of interstitial cystitis/bladder pain syndrome. Sci Rep. 2016 May 18;6:26083. doi: 10.1038/srep26083. [PubMed:27188581 ]
Ulcerative colitis
Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Thyroid cancer
Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9. [PubMed:14643447 ]

Associated OMIM IDs

145500 (Hypertension)
211980 (Lung Cancer)
181500 (Schizophrenia)
243500 (Isovaleric acidemia)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17351

Food Biomarker Ontology

Not Available

VMH ID

LNLC

MarkerDB ID

MDB00000213

Good Scents ID

rw1045901

References

Synthesis Reference

Walborsky, Harry M.; Davis, Robert H.; Howton, David R. A total synthesis of linoleic acid. Journal of the American Chemical Society (1951), 73 2590-4.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
Schurer NY, Stremmel W, Grundmann JU, Schliep V, Kleinert H, Bass NM, Williams ML: Evidence for a novel keratinocyte fatty acid uptake mechanism with preference for linoleic acid: comparison of oleic and linoleic acid uptake by cultured human keratinocytes, fibroblasts and a human hepatoma cell line. Biochim Biophys Acta. 1994 Feb 10;1211(1):51-60. [PubMed:8123682 ]
Valianpour F, Wanders RJ, Overmars H, Vaz FM, Barth PG, van Gennip AH: Linoleic acid supplementation of Barth syndrome fibroblasts restores cardiolipin levels: implications for treatment. J Lipid Res. 2003 Mar;44(3):560-6. Epub 2002 Dec 16. [PubMed:12562862 ]
Horrobin DF: Essential fatty acid metabolism and its modification in atopic eczema. Am J Clin Nutr. 2000 Jan;71(1 Suppl):367S-72S. [PubMed:10617999 ]
Imokawa G, Yada Y, Higuchi K, Okuda M, Ohashi Y, Kawamata A: Pseudo-acylceramide with linoleic acid produces selective recovery of diminished cutaneous barrier function in essential fatty acid-deficient rats and has an inhibitory effect on epidermal hyperplasia. J Clin Invest. 1994 Jul;94(1):89-96. [PubMed:8040295 ]
Kawajiri H, Hsi LC, Kamitani H, Ikawa H, Geller M, Ward T, Eling TE, Glasgow WC: Arachidonic and linoleic acid metabolism in mouse intestinal tissue: evidence for novel lipoxygenase activity. Arch Biochem Biophys. 2002 Feb 1;398(1):51-60. [PubMed:11811948 ]
Iso H, Sato S, Umemura U, Kudo M, Koike K, Kitamura A, Imano H, Okamura T, Naito Y, Shimamoto T: Linoleic acid, other fatty acids, and the risk of stroke. Stroke. 2002 Aug;33(8):2086-93. [PubMed:12154268 ]
Seidel D, Heipertz R, Weisner B: Cerebrospinal fluid lipids in demyelinating disease. II. Linoleic acid as an index of impaired blood-CSF barrier. J Neurol. 1980 Jan;222(3):177-82. [PubMed:6153705 ]
Salo P, Seppanen-Laakso T, Laakso I, Seppanen R, Niinikoski H, Viikari J, Simell O: Low-saturated fat, low-cholesterol diet in 3-year-old children: effect on intake and composition of trans fatty acids and other fatty acids in serum phospholipid fraction-The STRIP study. Special Turku coronary Risk factor Intervention Project for children. J Pediatr. 2000 Jan;136(1):46-52. [PubMed:10636973 ]
Grimsgaard S, Bonaa KH, Jacobsen BK, Bjerve KS: Plasma saturated and linoleic fatty acids are independently associated with blood pressure. Hypertension. 1999 Sep;34(3):478-83. [PubMed:10489397 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 52 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Calcium-dependent phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:: PLA2G5
Uniprot ID:: P39877
Molecular weight:: 15674.065

Reactions

Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic acid	details

Enzyme Details

2. Group IIF secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:: PLA2G2F
Uniprot ID:: Q9BZM2
Molecular weight:: 23256.29

Reactions

Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic acid	details

Enzyme Details

3. Cytosolic phospholipase A2

General function:: Involved in metabolic process
Specific function:: Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:: PLA2G4A
Uniprot ID:: P47712
Molecular weight:: 85210.19

Reactions

Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic acid	details

Enzyme Details

4. Phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:: PLA2G1B
Uniprot ID:: P04054
Molecular weight:: 16359.535

Reactions

Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic acid	details

Enzyme Details

5. Group XIIB secretory phospholipase A2-like protein

General function:: Involved in phospholipase A2 activity
Specific function:: Not known; does not seem to have catalytic activity.
Gene Name:: PLA2G12B
Uniprot ID:: Q9BX93
Molecular weight:: Not Available

Reactions

Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic acid	details

Enzyme Details

6. Group 10 secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:: PLA2G10
Uniprot ID:: O15496
Molecular weight:: 18153.04

Reactions

Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic acid	details

Enzyme Details

7. Group IIE secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:: PLA2G2E
Uniprot ID:: Q9NZK7
Molecular weight:: 15988.525

Reactions

Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic acid	details

Enzyme Details

8. Group XIIA secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Does not exhibit detectable activity toward sn-2-arachidonoyl- or linoleoyl-phosphatidylcholine or -phosphatidylethanolamine.
Gene Name:: PLA2G12A
Uniprot ID:: Q9BZM1
Molecular weight:: 21066.99

Reactions

Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic acid	details

Enzyme Details

9. 85/88 kDa calcium-independent phospholipase A2

General function:: Involved in metabolic process
Specific function:: Catalyzes the release of fatty acids from phospholipids. It has been implicated in normal phospholipid remodeling, nitric oxide-induced or vasopressin-induced arachidonic acid release and in leukotriene and prostaglandin production. May participate in fas mediated apoptosis and in regulating transmembrane ion flux in glucose-stimulated B-cells. Has a role in cardiolipin (CL) deacylation. Required for both speed and directionality of monocyte MCP1/CCL2-induced chemotaxis through regulation of F-actin polymerization at the pseudopods. Isoform ankyrin-iPLA2-1 and isoform ankyrin-iPLA2-2, which lack the catalytic domain, are probably involved in the negative regulation of iPLA2 activity.
Gene Name:: PLA2G6
Uniprot ID:: O60733
Molecular weight:: 84092.635

Reactions

Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic acid	details

Enzyme Details

10. Phospholipase A2, membrane associated

General function:: Involved in phospholipase A2 activity
Specific function:: Thought to participate in the regulation of the phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:: PLA2G2A
Uniprot ID:: P14555
Molecular weight:: 16082.525

Reactions

Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Linoleic acid	details

Only showing the first 10 proteins. There are 52 proteins in total.

Show all enzymes and transporters

Showing metabocard for Linoleic acid (HMDB0000673)

MOL for HMDB0000673 (Linoleic acid)

3D MOL for HMDB0000673 (Linoleic acid)

3D SDF for HMDB0000673 (Linoleic acid)

3D-SDF for HMDB0000673 (Linoleic acid)

PDB for HMDB0000673 (Linoleic acid)

3D PDB for HMDB0000673 (Linoleic acid)

SMILES for HMDB0000673 (Linoleic acid)

INCHI for HMDB0000673 (Linoleic acid)

Structure for HMDB0000673 (Linoleic acid)

3D Structure for HMDB0000673 (Linoleic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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