NP-MRD: Showing NP-Card for Linoleic acid (NP0000790)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-10-07 20:41:56 UTC

NP-MRD ID

NP0000790

Secondary Accession Numbers

None

Natural Product 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>
NP0000790

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

280.4455 Da

Monoisotopic Mass

280.24023 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	LOTUS Database	35616633
Abies pinsapo	LOTUS Database	35616633
Abutilon ramosum	LOTUS Database	35616633
Acacia mearnsii	LOTUS Database	35616633
Achillea fragrantissima	LOTUS Database	35616633
Aconitum japonicum	LOTUS Database	35616633
Acorus calamus	LOTUS Database	35616633
Acorus calanus L.	KNApSAcK Database	22123792
Adenophora triphylla	LOTUS Database	35616633
Aegle marmelos	Plant	KNApSAcK
Aesculus hippocastanum	LOTUS Database	35616633
Aesculus hippocastanum L.	KNApSAcK Database	22123792
Agaricus bisporus	LOTUS Database	35616633
Agaricus blazei	LOTUS Database	35616633
Agave americana	LOTUS Database	35616633
Agave decipiens	LOTUS Database	35616633
Ageratum conyzoides	LOTUS Database	35616633
Ailanthus altissima	LOTUS Database	35616633
Ailuropoda melanoleuca	LOTUS Database	35616633
Aleurites moluccana	KNApSAcK Database	22123792
Aleurites moluccanus	Plant	KNApSAcK
Aleurites montana	KNApSAcK Database	22123792
Allium cepa	LOTUS Database	35616633
Allium hirtifolium	Plant	KNApSAcK
Allium obliquum	LOTUS Database	35616633
Allium sativum	LOTUS Database	35616633
Alpinia oxyphylla	KNApSAcK Database	22123792
Althaea officinalis	LOTUS Database	35616633
Amaranthus caudatus	LOTUS Database	35616633
Amaranthus paniculatus	LOTUS Database	35616633
Amaranthus tricolor	LOTUS Database	35616633
Anagallis arvensis	LOTUS Database	35616633
Anethum graveolens	LOTUS Database	35616633
Angelica pubescens	LOTUS Database	35616633
Anisophyllea laurina	LOTUS Database	35616633
Aphanamixis polystachya	KNApSAcK Database	22123792
Apios americana	LOTUS Database	35616633
Arabidopsis thaliana	LOTUS Database	35616633
Arachis hypogaea	LOTUS Database	35616633
Arisaema tortuosum	LOTUS Database	35616633
Arnica montana	LOTUS Database	35616633
Artemisia baldshuanica	LOTUS Database	35616633
Artocarpus heterophyllus	LOTUS Database	35616633
Asclepias syriaca	LOTUS Database	35616633
Asparagus officinalis	Plant	KNApSAcK
Atractylodes lancea	LOTUS Database	35616633
Attalea colenda	LOTUS Database	35616633
Averrhoa carambola	KNApSAcK Database	22123792
Azima tetracantha	LOTUS Database	35616633
Barringtonia asiatica	LOTUS Database	35616633
Bauhinia tomentosa	KNApSAcK Database	22123792
Bellis perennis	LOTUS Database	35616633
Bidens pilosa	LOTUS Database	35616633
Bidens tripartita	LOTUS Database	35616633
Boa constrictor	LOTUS Database	35616633
Boehmeria holosericea	KNApSAcK Database	22123792
Boehmeria nivea	LOTUS Database	35616633
Boehmeria tricuspis	KNApSAcK Database	22123792
Bombax ceiba	LOTUS Database	35616633
Borago officinalis	LOTUS Database	35616633
Brassica hirta	KNApSAcK Database	22123792
Brassica napus	LOTUS Database	35616633
Brassica rapa	LOTUS Database	35616633
Bredemeyera brevifolia	LOTUS Database	35616633
Brunfelsia americana	LOTUS Database	35616633
Bryonia alba	LOTUS Database	35616633
Cachrys sicula	LOTUS Database	35616633
Calophyllum calaba	KNApSAcK Database	22123792
Calophyllum inophyllum	KNApSAcK Database	22123792
Camellia sinensis	LOTUS Database	35616633
Canarium album	LOTUS Database	35616633
Canavalia ensiformis	LOTUS Database	35616633
Cannabis sativa	CannabisDB	Not Available
Capparis spinosa	LOTUS Database	35616633
Carica papaya	LOTUS Database	35616633
Carthamus oxyacanthus	LOTUS Database	35616633
Carthamus tinctorius	LOTUS Database	35616633
Caryodendron orinocense	LOTUS Database	35616633
Cassia absu	Plant	KNApSAcK
Cassia fistula	LOTUS Database	35616633
Cassia javanica	LOTUS Database	35616633
Catharanthus roseus	LOTUS Database	35616633
Cedrela odorata	LOTUS Database	35616633
Celastrus hypoleucus	LOTUS Database	35616633
Celastrus paniculata	LOTUS Database	35616633
Centaurea aspera	LOTUS Database	35616633
Chamaecyparis formosensis	LOTUS Database	35616633
Chamaemalum nobile	-	KNApSAcK
Chlamydomonas reinhardtii	LOTUS Database	35616633
Citrullus colocynthis	LOTUS Database	35616633
Citrullus lanatus	LOTUS Database	35616633
Citrus reticulata	LOTUS Database	35616633
Citrus sinensis	LOTUS Database	35616633
Cleome amblyocarpa	LOTUS Database	35616633
Clitoria ternata	KNApSAcK Database	22123792
Clitoria ternatea	LOTUS Database	35616633
Clivia miniata	LOTUS Database	35616633
Clonostachys candelabrum	LOTUS Database	35616633
Coix lacryma-jobi	LOTUS Database	35616633
Colletia spinosissima	LOTUS Database	35616633
Consolida regalis	LOTUS Database	35616633
Cordia sinensis	LOTUS Database	35616633
Corymbia citriodora	LOTUS Database	35616633
Crotalaria pallida	LOTUS Database	35616633
Crotalaria retusa	LOTUS Database	35616633
Cryptolepis buchananii	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Cryptostegia grandiflora	LOTUS Database	35616633
Cucumis melo	LOTUS Database	35616633
Cucumis sativus	LOTUS Database	35616633
Cucurbita foetidissima	LOTUS Database	35616633
Cucurbita pepo	LOTUS Database	35616633
Cullen corylifolium	Plant	KNApSAcK
Cuphea appendiculata	LOTUS Database	35616633
Curcuma longa	Plant	KNApSAcK
Curcurbita pepo L.	-	KNApSAcK
Cuscuta campestris	LOTUS Database	35616633
Cyamopsis tetragonoloba	LOTUS Database	35616633
Cynara cornigera	LOTUS Database	35616633
Cystoclonium purpureum	LOTUS Database	35616633
Dalbergia lanceolaria	LOTUS Database	35616633
Datura stramonium	LOTUS Database	35616633
Daucus carota ssp. sativus	KNApSAcK Database	22123792
Delonix regia	LOTUS Database	35616633
Dictamnus albus	LOTUS Database	35616633
Dimerostemma brasilianum	LOTUS Database	35616633
Dipteryx lacunifera	LOTUS Database	35616633
Dipteryx odorata	LOTUS Database	35616633
Dirca palustris	LOTUS Database	35616633
Dovyalis caffra	LOTUS Database	35616633
Drymaria cordata	KNApSAcK Database	22123792
Dryopteris expansa	LOTUS Database	35616633
Duhaldea cappa	LOTUS Database	35616633
Echinacea purpurea	LOTUS Database	35616633
Echium auberianum	KNApSAcK Database	22123792
Echium boissieri	KNApSAcK Database	22123792
Echium gentianoides	KNApSAcK Database	22123792
Echium giganteum	KNApSAcK Database	22123792
Echium lusitanicum	KNApSAcK Database	22123792
Echium pitardii	KNApSAcK Database	22123792
Echium plantagineum	KNApSAcK Database	22123792
Echium sabulicola	KNApSAcK Database	22123792
Echium strictum	KNApSAcK Database	22123792
Echium vulgare	KNApSAcK Database	22123792
Elaeagnus angustifolia	LOTUS Database	35616633
Elaeis guineensis	LOTUS Database	35616633
Epilobium parviflorum	LOTUS Database	35616633
Equilabium molle	LOTUS Database	35616633
Erigeron caucasicus	LOTUS Database	35616633
Erigeron philadelphicus	LOTUS Database	35616633
Eriobotrya japonica	LOTUS Database	35616633
Erucaria microcarpa	LOTUS Database	35616633
Erycibe expansa	KNApSAcK Database	22123792
Erythrina suberosa	LOTUS Database	35616633
Euphausia superba	LOTUS Database	35616633
Euphorbia characias	LOTUS Database	35616633
Euphorbia glareosa	LOTUS Database	35616633
Euphorbia milii	LOTUS Database	35616633
Fagus orientalis	LOTUS Database	35616633
Fernandoa adenophylla	LOTUS Database	35616633
Foeniculum vulgare	LOTUS Database	35616633
Frullania anomala	Plant	KNApSAcK
Frullania incumbens	Plant	KNApSAcK
Frullania lobulata	Plant	KNApSAcK
Frullania probosciphora	Plant	KNApSAcK
Frullania pycnantha	Plant	KNApSAcK
Frullania scandens	Plant	KNApSAcK
Frullania solanderiana	Plant	KNApSAcK
Frullania spinifera	Plant	KNApSAcK
Fumaria vaillantii	LOTUS Database	35616633
Gaillardia suavis	LOTUS Database	35616633
Ganoderma australe	LOTUS Database	35616633
Garcinia dulcis	LOTUS Database	35616633
Gardenia resinifera	LOTUS Database	35616633
Gladiolus italicus	LOTUS Database	35616633
Gleditsia triacanthos	LOTUS Database	35616633
Glycine max	KNApSAcK Database	22123792
Gnetum edule	LOTUS Database	35616633
Gossypium hirsutum	LOTUS Database	35616633
Gremmeniella abietina	LOTUS Database	35616633
Gustavia longifolia	LOTUS Database	35616633
Gynura japonica	LOTUS Database	35616633
Hansenia weberbaueriana	LOTUS Database	35616633
Helianthus porteri	LOTUS Database	35616633
Heracleum dissectum	LOTUS Database	35616633
Hibiscus cannabinus	LOTUS Database	35616633
Hibiscus sabdariffa	LOTUS Database	35616633
Hieracium intybaceum All.	LOTUS Database	35616633
Hippophae rhamnoides	LOTUS Database	35616633
Hirschfeldia incana	LOTUS Database	35616633
Homo sapiens	LOTUS Database	35616633
Houttuynia cordata	LOTUS Database	35616633
Hoya coronaria	LOTUS Database	35616633
Humulus lupulus	LOTUS Database	35616633
Hygrophorus chrysodon	LOTUS Database	35616633
Hyoscyamus muticus	LOTUS Database	35616633
Hypericum perforatum	LOTUS Database	35616633
Inezia integrifolia	LOTUS Database	35616633
Inula grandis	LOTUS Database	35616633
Iris sofarana	LOTUS Database	35616633
Iris soforana	KNApSAcK Database	22123792
Isatis tinctoria	KNApSAcK Database	22123792
Jasminum auriculatum	KNApSAcK Database	22123792
Jasminum fluminense	LOTUS Database	35616633
Jatropha curcus	KNApSAcK Database	22123792
Jatropha gossypifolia	LOTUS Database	35616633
Jodina rhombifolia	LOTUS Database	35616633
Justicia heterocarpa T.ANDERS	KNApSAcK Database	22123792
Lactuca saligna L.	LOTUS Database	35616633
Lactuca serriola	LOTUS Database	35616633
Lagenaria breviflora	LOTUS Database	35616633
Lagerstroemia speciosa	LOTUS Database	35616633
Lagerstroemia thomsonil	KNApSAcK Database	22123792
Laminaria japonica	KNApSAcK Database	22123792
Lantana camara	LOTUS Database	35616633
Lantana ukambensis	LOTUS Database	35616633
Larix gmelini	LOTUS Database	35616633
Lathraea squamaria	LOTUS Database	35616633
Laurus nobilis	KNApSAcK Database	22123792
Laurus nobilis L.	Plant	KNApSAcK
Lemna aequinoctialis	LOTUS Database	35616633
Lepidium meyenii	LOTUS Database	35616633
Lepidium meyenii Maca	KNApSAcK Database	22123792
Leptolyngbya tenuis	LOTUS Database	35616633
Leptomitus lacteus	LOTUS Database	35616633
Leucaena glauca	LOTUS Database	35616633
Leucopaxillus gentianeus	LOTUS Database	35616633
Ligularia macrophylla	LOTUS Database	35616633
Ligularia nelumbifolia	LOTUS Database	35616633
Ligustrum lucidum	LOTUS Database	35616633
Linum usitatissimum	LOTUS Database	35616633
Lupinus albus	KNApSAcK Database	22123792
Lygodium japonicum	LOTUS Database	35616633
Maackia amurensis	LOTUS Database	35616633
Macadamia integrifolia	LOTUS Database	35616633
Maclura pomifera	LOTUS Database	35616633
Macrococculus pomiferus	LOTUS Database	35616633
Malus domestica	LOTUS Database	35616633
Malva sylvestris	LOTUS Database	35616633
Mandragora autumnalis	KNApSAcK Database	22123792
Mangifera indica	KNApSAcK Database	22123792
Matricaria chamomilla	KNApSAcK Database	22123792
Mentha spicata	LOTUS Database	35616633
Michelia alba	LOTUS Database	35616633
Microglossa pyrifolia	LOTUS Database	35616633
Mikania goyazensis	LOTUS Database	35616633
Mitracarpus hirtus	LOTUS Database	35616633
Momordica charantia	LOTUS Database	35616633
Monascus pilosus	LOTUS Database	35616633
Mucuna puriens	Plant	KNApSAcK
Musa paradisiaca	LOTUS Database	35616633
Myuroclada maximowiczii	LOTUS Database	35616633
Narthecium ossifragum	LOTUS Database	35616633
Nervilia plicata	LOTUS Database	35616633
Nicotiana tabacum	KNApSAcK Database	22123792
Nigella sativa	Plant	KNApSAcK
Nothapodytes nimmoniana	LOTUS Database	35616633
Nymphaea alba	KNApSAcK Database	22123792
Ocimum basilicum	LOTUS Database	35616633
Oenothera biennis	LOTUS Database	35616633
Oenothera villosa	LOTUS Database	35616633
Olea europaea	LOTUS Database	35616633
Oleandra wallichii	LOTUS Database	35616633
Ononis natrix	LOTUS Database	35616633
Opisthoplatia orientalis	LOTUS Database	35616633
Panax ginseng	Plant	KNApSAcK
Panax quinquefolius	LOTUS Database	35616633
Pandanus conoideus	LOTUS Database	35616633
Papaver bracteatum	LOTUS Database	35616633
Parinari montana	LOTUS Database	35616633
Passiflora foetida	LOTUS Database	35616633
Paxillus involutus	LOTUS Database	35616633
Peganum harmala	LOTUS Database	35616633
Penicillium javanicum	LOTUS Database	35616633
Penicillium oxalicum	LOTUS Database	35616633
Pentaclethra macrophylla	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Periploca sepium	LOTUS Database	35616633
Petiveria alliacea	LOTUS Database	35616633
Phaseolus coccineus	LOTUS Database	35616633
Picea jezoensis	LOTUS Database	35616633
Picea obovata	LOTUS Database	35616633
Pinus monticola	LOTUS Database	35616633
Pinus pinaster	LOTUS Database	35616633
Pinus resinosa	LOTUS Database	35616633
Pinus sibirica	KNApSAcK Database	22123792
Pistacia vera	LOTUS Database	35616633
Pithecellobium dulce	LOTUS Database	35616633
Plagiochila porelloides	LOTUS Database	35616633
Plantago ovata	LOTUS Database	35616633
Pleurotus ostreatus	LOTUS Database	35616633
Pleurotus pulmonarius	LOTUS Database	35616633
Pongamia pinnata	LOTUS Database	35616633
Populus tremula	LOTUS Database	35616633
Populus tremuloides	LOTUS Database	35616633
Portulaca oleracea	LOTUS Database	35616633
Potentilla asiatica	KNApSAcK Database	22123792
Potentilla desertorum	KNApSAcK Database	22123792
Potentilla orientalis	KNApSAcK Database	22123792
Poterium polygamum	-	KNApSAcK
Prunus africana	LOTUS Database	35616633
Prunus armeniaca	LOTUS Database	35616633
Prunus cerasus	LOTUS Database	35616633
Prunus laurocerasus	LOTUS Database	35616633
Prunus mume	LOTUS Database	35616633
Pseudostellaria heterophylla	LOTUS Database	35616633
Psophocarpus tetragonolobus	LOTUS Database	35616633
Psoralea corylifolia	KNApSAcK Database	22123792
Pterodon emarginatus	LOTUS Database	35616633
Punica granatum	KNApSAcK Database	22123792
Pythium aphanidermatum	LOTUS Database	35616633
Rana temporaria	LOTUS Database	35616633
Rhodotorula glutinis	LOTUS Database	35616633
Rhytidiadelphus squarrosus	LOTUS Database	35616633
Ribes nigrum	LOTUS Database	35616633
Rosa canina	LOTUS Database	35616633
Rosa platyacantha	LOTUS Database	35616633
Rosa taiwanensis	LOTUS Database	35616633
Saccharina japonica	Plant	KNApSAcK
Salvia fruticosa	LOTUS Database	35616633
Saussurea involucrata	LOTUS Database	35616633
Saussurea medusa	LOTUS Database	35616633
Saxifraga stolonifera Meerb.	KNApSAcK Database	22123792
Scomber japonicus	LOTUS Database	35616633
Scrophularia nodosa	LOTUS Database	35616633
Scurrula atropurpurea	LOTUS Database	35616633
Sebastiana sebiferum	-	KNApSAcK
Senegalia mellifera	Plant	KNApSAcK
Senna alexandrina	LOTUS Database	35616633
Senna corymbosa	LOTUS Database	35616633
Serenoa repens	LOTUS Database	35616633
Serpocaulon loriceum	LOTUS Database	35616633
Sesamum indicum	LOTUS Database	35616633
Sideritis taurica	LOTUS Database	35616633
Silybum marianum	KNApSAcK Database	22123792
Sinapis alba	Plant	KNApSAcK
Skeletonema marinoi	LOTUS Database	35616633
Solanum argentinum	LOTUS Database	35616633
Solanum tuberosum	KNApSAcK Database	22123792
Spermacoce pusilla	LOTUS Database	35616633
Spinacia oleracea	LOTUS Database	35616633
Spongiporus leucomallellus (Murril)	-	KNApSAcK
Stellaria dichotoma	LOTUS Database	35616633
Sterculia tragacantha	LOTUS Database	35616633
Strychnos spinosa	LOTUS Database	35616633
Suaeda aegyptiaca	LOTUS Database	35616633
Syzygium cumini	LOTUS Database	35616633
Talaromyces flavus	LOTUS Database	35616633
Taraxacum officinale	LOTUS Database	35616633
Taxus mairei	LOTUS Database	35616633
Terminalia pallida	LOTUS Database	35616633
Thalictrum revolutum	LOTUS Database	35616633
Theobroma cacao	LOTUS Database	35616633
Thlaspi arvense	LOTUS Database	35616633
Thuja occidentalis	LOTUS Database	35616633
Tilia cordata	Plant	KNApSAcK
Tilia cordata Mill.	KNApSAcK Database	22123792
Tilia tomentosa	LOTUS Database	35616633
Toona sinensis	LOTUS Database	35616633
Tornabea scutellifera	LOTUS Database	35616633
Trichodesma zeylanicum	LOTUS Database	35616633
Trichosanthes tricuspidata	LOTUS Database	35616633
Trifolium repens	LOTUS Database	35616633
Trigonella foenum-graecum	LOTUS Database	35616633
Trillium erectum	LOTUS Database	35616633
Tripterygium hypoglaucum	KNApSAcK Database	22123792
Turnera ulmifolia	LOTUS Database	35616633
Typha domingensis	LOTUS Database	35616633
Typha domingensis P.	KNApSAcK Database	22123792
Ulva pertusa	LOTUS Database	35616633
Vachellia constricta	LOTUS Database	35616633
Ventilago denticulata	LOTUS Database	35616633
Vigna angularis	LOTUS Database	35616633
Vigna subterranea	LOTUS Database	35616633
Viguiera dentata	LOTUS Database	35616633
Vitex agnus-castus	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633
Warburgia ugandensis	LOTUS Database	35616633
Wedelia acapulcensis	LOTUS Database	35616633
Withania somnifera	Plant	KNApSAcK
Zanthoxylum beecheyanum	LOTUS Database	35616633
Zea mays	LOTUS Database	35616633
Ziziphus jujuba	LOTUS Database	35616633
Ziziphus spina-christi	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Aspergillus insuetus	KNApSAcK Database	22123792
Ganoderma lucidum	KNApSAcK Database	22123792
Homo sapiens (Serum)	KNApSAcK Database	22123792
Monascus pilosus BCRC38072	KNApSAcK Database	22123792

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 )

Physical Properties

State

Liquid

Experimental 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, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.

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

External Links

HMDB ID

HMDB0000673

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1045901

References

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 ]

Showing NP-Card for Linoleic acid (NP0000790)

MOL for NP0000790 (Linoleic acid)

3D MOL for NP0000790 (Linoleic acid)

3D SDF for NP0000790 (Linoleic acid)

3D-SDF for NP0000790 (Linoleic acid)

PDB for NP0000790 (Linoleic acid)

3D PDB for NP0000790 (Linoleic acid)

SMILES for NP0000790 (Linoleic acid)

INCHI for NP0000790 (Linoleic acid)

Structure for NP0000790 (Linoleic acid)

3D Structure for NP0000790 (Linoleic acid)