MiMeDB: Showing metabocard for Linoleic acid (MMDBc0000136)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:37:11 UTC

Update Date

2022-08-30 23:58:24 UTC

Metabolite ID

MMDBc0000136

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>
MMDBc0000136

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₈H₃₂O₂

Average Mass

280.4455

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Adipose Tissue
Blood
Cerebrospinal Fluid (CSF)
Epidermis
Erythrocyte
Feces
Fibroblasts
Intestine
Kidney
Neuron
Placenta
Platelet
Prostate
Saliva
Skeletal Muscle
Spleen
Urine

Tissue Locations

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

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191732	Calcium-dependent phospholipase A2	Unknown	P39877	Homo_sapiens
MMDBp0191733	Group IIF secretory phospholipase A2	Unknown	Q9BZM2	Homo_sapiens
MMDBp0191734	Cytosolic phospholipase A2	Unknown	P47712	Homo_sapiens
MMDBp0191735	Phospholipase A2	Unknown	P04054	Homo_sapiens
MMDBp0191736	Group XIIB secretory phospholipase A2-like protein	Unknown	Q9BX93	Homo_sapiens
MMDBp0191737	Group 10 secretory phospholipase A2	Unknown	O15496	Homo_sapiens
MMDBp0191739	Group IIE secretory phospholipase A2	Unknown	Q9NZK7	Homo_sapiens
MMDBp0191741	Group XIIA secretory phospholipase A2	Unknown	Q9BZM1	Homo_sapiens
MMDBp0191742	85/88 kDa calcium-independent phospholipase A2	Unknown	O60733	Homo_sapiens
MMDBp0191745	Phospholipase A2, membrane associated	Unknown	P14555	Homo_sapiens
MMDBp0191746	Group IID secretory phospholipase A2	Unknown	Q9UNK4	Homo_sapiens
MMDBp0192178	Cytosolic phospholipase A2 gamma	Unknown	Q9UP65	Homo_sapiens
MMDBp0192181	Group 3 secretory phospholipase A2	Unknown	Q9NZ20	Homo_sapiens
MMDBp0192196	Bile acid-CoA:amino acid N-acyltransferase	Enzyme	Q14032	Homo_sapiens
MMDBp0192584	Arachidonate 5-lipoxygenase	Unknown	P09917	Homo_sapiens
MMDBp0192585	Arachidonate 15-lipoxygenase B	Unknown	O15296	Homo_sapiens
MMDBp0192589	Arachidonate 15-lipoxygenase	Unknown	P16050	Homo_sapiens
MMDBp0192630	Cytochrome P450 3A4	Unknown	P08684	Homo_sapiens
MMDBp0192647	Cytochrome P450 2C9	Unknown	P11712	Homo_sapiens
MMDBp0192649	Cytochrome P450 2C19	Unknown	P33261	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
MMDBp0193099	Cytochrome P450 2E1	Unknown	P05181	Homo_sapiens
MMDBp0193101	Cytochrome P450 3A43	Unknown	Q9HB55	Homo_sapiens
MMDBp0193102	Cytochrome P450 1B1	Unknown	Q16678	Homo_sapiens
MMDBp0193104	Cytochrome P450 2C18	Unknown	P33260	Homo_sapiens
MMDBp0193106	Cytochrome P450 2F1	Unknown	P24903	Homo_sapiens
MMDBp0193107	Cytochrome P450 4X1	Unknown	Q8N118	Homo_sapiens
MMDBp0193108	Cytochrome P450 2B6	Unknown	P20813	Homo_sapiens
MMDBp0193109	Cytochrome P450 3A5	Unknown	P20815	Homo_sapiens
MMDBp0193111	Cytochrome P450 2A13	Unknown	Q16696	Homo_sapiens
MMDBp0193112	Cytochrome P450 3A7	Unknown	P24462	Homo_sapiens
MMDBp0193113	Cytochrome P450 4B1	Unknown	P13584	Homo_sapiens
MMDBp0193114	Cytochrome P450 4Z1	Unknown	Q86W10	Homo_sapiens
MMDBp0193115	Cytochrome P450 1A2	Unknown	P05177	Homo_sapiens
MMDBp0193116	Cytochrome P450 19A1	Unknown	P11511	Homo_sapiens
MMDBp0193117	Cytochrome P450 2C8	Unknown	P10632	Homo_sapiens
MMDBp0193118	Cytochrome P450 2S1	Unknown	Q96SQ9	Homo_sapiens
MMDBp0193120	Cytochrome P450 2J2	Unknown	P51589	Homo_sapiens
MMDBp0193121	Cytochrome P450 2A7	Unknown	P20853	Homo_sapiens
MMDBp0193122	Cytochrome P450 2A6	Unknown	P11509	Homo_sapiens
MMDBp0194097	Phospholipase B1, membrane-associated	Unknown	Q6P1J6	Homo_sapiens
MMDBp0194192	Cytochrome P450, family 1, subfamily A, polypeptide 1	Enzyme	A0N0X8	Homo_sapiens
MMDBp0194634	Cytosolic phospholipase A2 delta	Unknown	Q86XP0	Homo_sapiens
MMDBp0194635	Cytosolic phospholipase A2 epsilon	Unknown	Q3MJ16	Homo_sapiens
MMDBp0194636	Cytosolic phospholipase A2 zeta	Unknown	Q68DD2	Homo_sapiens
MMDBp0195865	Cytosolic phospholipase A2 beta	Unknown	P0C869	Homo_sapiens
MMDBp0196019	Cytochrome P450 2D6	Enzyme	Q6NWU0	Homo_sapiens
MMDBp0196516	Acyl-coenzyme A thioesterase 1	Enzyme	Q86TX2	Homo_sapiens
MMDBp0196846	HRAS-like suppressor 3	Unknown	P53816

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

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Cirrhosis	Increased	Association	Human Blood	HMDB	3101533
Essential hypertension	Decreased	Association	Human Blood	HMDB	18633173
Gestational diabetes		Association	Human Blood	HMDB	14634727
Hypertension		Association	Human Blood	HMDB	18633173
Isovaleric acidemia		Association	Human Blood	HMDB	27329611
Schizophrenia		Association	Human Blood	HMDB	25004141
Thyroid cancer	Slight Decrease	Association	Human Urine	HMDB	14643447

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	2	Human	Microbial culture
Bacteria	Firmicutes	4	Human	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	1	Human feces	Unknown

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified								HMDB
Human	Detected and Quantified	886.0	626.6			Adult (>18 years old)	Both	Cirrhosis	HMDB	3101533
Human	Detected and Quantified	167.0	63.8			Adult (>18 years old)	Male	Essential hypertension	HMDB	18633173
Human	Detected and Quantified	195.2	64.4			Adult (>18 years old)	Female	Essential hypertension	HMDB	18633173
Human	Detected and Quantified	22.61	2.80			Adult (>18 years old)	Female	Gestational diabetes mellitus (GDM)	HMDB	14634727
Human	Detected and Quantified	175.9	65.0			Adult (>18 years old)	Both	Hypertension	HMDB	18633173
Human	Detected and Quantified	2796.7	493.9			Adult (>18 years old)	Not Specified	Isovaleric acidemia	HMDB	27329611
Human	Detected and Quantified	159	12.0			Adult (>18 years old)	Both	Schizophrenia	HMDB	25004141
Human	Detected and Quantified	0.18	0.45			Adult (>18 years old)	Female	Thyroid cancer	HMDB	14643447
Human	Detected and Quantified	61				Adult (>18 years old)	Both	Normal	HMDB	2000815
Human	Detected and Quantified	74				Adult (>18 years old)	Both	Normal	HMDB	2000815
Human	Detected and Quantified	134				Adult (>18 years old)	Both	Normal	HMDB	2000815
Human	Detected and Quantified	192				Adult (>18 years old)	Both	Normal	HMDB	2000815
Human	Detected and Quantified	246				Adult (>18 years old)	Both	Normal	HMDB	2000815
Human	Detected and Quantified	291				Adult (>18 years old)	Both	Normal	HMDB	2000815
Human	Detected and Quantified	308				Adult (>18 years old)	Both	Normal	HMDB	2000815
Human	Detected and Quantified	311				Adult (>18 years old)	Both	Normal	HMDB	2000815
Human	Detected and Quantified	525				Adult (>18 years old)	Both	Normal	HMDB	2000815
Human	Detected and Quantified	563				Adult (>18 years old)	Both	Normal	HMDB	2000815
Human	Detected and Quantified	618				Adult (>18 years old)	Both	Normal	HMDB	2000815
Human	Detected and Quantified	1.19	0.61			Adult (>18 years old)	Female	Normal	HMDB	14643447
Human	Detected and Quantified	1021.482	224.215			Adult (>18 years old)	Both	Normal	HMDB	17313719
Human	Detected and Quantified	1065.519	201.893			Adult (>18 years old)	Female	Normal	HMDB	9368807
Human	Detected and Quantified	11.0	3.0			Adult (>18 years old)	Not Specified	Normal	HMDB	8412012
Human	Detected and Quantified	110		42	370	Adult (>18 years old)	Both	Normal	HMDB	8412012
Human	Detected and Quantified	14.733	4.331			Adult (>18 years old)	Both	Normal	HMDB	18953024
Human	Detected and Quantified	14.733	4.331			Adult (>18 years old)	Both	Normal	HMDB	21359215
Human	Detected and Quantified	15.2	0.437			Adult (>18 years old)	Both	Normal	HMDB	20671299
Human	Detected and Quantified	183.7	69.9			Adult (>18 years old)	Male	Normal	HMDB	18633173
Human	Detected and Quantified	193.7	72.0			Adult (>18 years old)	Both	Normal	HMDB	18633173
Human	Detected and Quantified	207.9	73.0			Adult (>18 years old)	Female	Normal	HMDB	18633173
Human	Detected and Quantified	23.39	2.75			Adult (>18 years old)	Female	Normal	HMDB	14634727
Human	Detected and Quantified	264	17.0			Adult (>18 years old)	Both	Normal	HMDB	25004141
Human	Detected and Quantified	734.546	92.710			Adult (>18 years old)	Male	Normal	HMDB	17069347
Human	Detected and Quantified	798.729	99.841			Adult (>18 years old)	Male	Normal	HMDB	17069347
Human	Detected and Quantified	83.8	38			Adult (>18 years old)	Both	Normal	HMDB	21359215
Human	Detected and Quantified	927.0964	110.538			Adult (>18 years old)	Male	Normal	HMDB	17069347
Human	Detected and Quantified	930.662	89.144			Adult (>18 years old)	Male	Normal	HMDB	17069347
Human	Detected and Quantified	0.05	0.05			Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human	Detected and Quantified			11.8	21.6	Adult (>18 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human	Detected and Quantified	17.7	4.7			Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
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 Intestine	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 Neuron	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 Prostate	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 Spleen	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Not Specified	Normal	HMDB	24421258
Human Feces	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	19573517
Human Feces	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	20669995
Human Feces	Detected but not Quantified					Infant (0-1 year old)	Both	Normal	HMDB	22411374
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	23940645
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	24029555
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	24424155
Human Blood	Detected but not Quantified					Adult (>18 years old)	Female	Normal	HMDB	22061338
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	19636438
Human Feces	Detected but not Quantified					Children (1-13 years old)	Both	Normal	HMDB	19636438
Human Blood	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	22007635
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	23384618
Human Feces	Detected but not Quantified					Infant (0-1 year old)	Not Specified	Normal	HMDB	24628373
Human Feces	Detected but not Quantified					Infant (0-1 year old)	Not Specified	Normal	HMDB	24628373
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	28842642
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	28587349
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

HMDB0000673

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

CMMC Knowledgebase

Not Available

General References

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. doi: 10.1007/BF00313116. [PubMed:6153705 ]
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. doi: 10.1172/JCI117352. [PubMed:8040295 ]
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. doi: 10.1016/0005-2760(94)90138-4. [PubMed:8123682 ]
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. doi: 10.1007/BF00711898. [PubMed:8412012 ]
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. doi: 10.1161/01.hyp.34.3.478. [PubMed:10489397 ]
Horrobin DF: Essential fatty acid metabolism and its modification in atopic eczema. Am J Clin Nutr. 2000 Jan;71(1 Suppl):367S-72S. doi: 10.1093/ajcn/71.1.367s. [PubMed:10617999 ]
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. doi: 10.1016/s0022-3476(00)90048-9. [PubMed:10636973 ]
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. doi: 10.1006/abbi.2001.2685. [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. doi: 10.1161/01.str.0000023890.25066.50. [PubMed:12154268 ]
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. doi: 10.1194/jlr.M200217-JLR200. Epub 2002 Dec 16. [PubMed:12562862 ]
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 ]
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 ]

Showing metabocard for Linoleic acid (MMDBc0000136)

MOL for #<Metabolite:0x0000560bdfda0a48>

3D MOL for #<Metabolite:0x0000560bdfda0a48>

3D SDF for #<Metabolite:0x0000560bdfda0a48>

3D-SDF for #<Metabolite:0x0000560bdfda0a48>

PDB for #<Metabolite:0x0000560bdfda0a48>

3D PDB for #<Metabolite:0x0000560bdfda0a48>

SMILES for #<Metabolite:0x0000560bdfda0a48>

INCHI for #<Metabolite:0x0000560bdfda0a48>

Structure for #<Metabolite:0x0000560bdfda0a48>

3D Structure for #<Metabolite:0x0000560bdfda0a48>