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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005047

Secondary Accession Numbers

HMDB05047

Metabolite Identification

Common Name

(9E,11E)-Octadecadienoic acid

Description

Conjugated linoleic acid is an integral term for the mixture of positional and geometrical isomers of the octadecadienoic acids, whose two double-bonds are separated with one single-bond. The most common isomers are cis-9, trans-11, and trans-10, cis-12. Conjugated linoleic acid is present in the food namely in the red meat and dairy products which the contemporary dietary recommendations tend to limit. Those limitations should be compensated with dietary supplements. Much attention has focused on the therapeutic potential of conjugated linoleic acid. Initial animal studies associated conjugated linoleic acid with beneficial health properties, such as reducing the risk of cancer, diabetes, atherosclerosis, inflammation and obesity. More recent human conjugated linoleic acid supplementation studies have often shown conflicting and less convincing health benefits. The marked variation between studies may reflect the isomer-specific effect of the individual conjugated linoleic acid isomers, which can often have opposing effects. Detrimental effects have been observed in some studies, in particular after supplementation with the trans-10,cis-12 conjugated linoleic acid isomer. Diet composition may modulate CLA effects on body fat accumulation. As far as human studies are concerned, a specific dietary pattern has not been established. As a result differences among studies and also among subjects in the same study are likely. In rodents, the effects of CLA vary with genotype, suggesting that genetic predisposition to fat accumulation can play an important role in the effectiveness of CLA. Human volunteers with different body mass index have participated in the published studies and even in the same experiment. So, differences in lipid metabolism among subjects could help to explain the discrepancies observed in the literature. Age and maturity may also be crucial. (PMID: 17053429 , 17217167 , 17554969 , 16477173 ).

Structure

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

HMDB0005047
     RDKit          3D
(9E,11E)-Octadecadienoic acid
 52 51  0  0  0  0  0  0  0  0999 V2000
    8.4530   -0.3270   -0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8062    0.7546   -0.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3455    0.4300    0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5782    0.3435   -1.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1299    0.0150   -0.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4442    1.0500    0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0285    0.6626    0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4639   -0.4308   -0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0563   -0.7397    0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4896   -1.8286   -0.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9231   -2.0941   -0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5337   -1.0197    0.7119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9907   -1.3727    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6503   -0.3171    1.8243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6303    1.0359    1.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3410    1.0803   -0.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7928    0.6898    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4831    0.7380   -1.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8371    1.0723   -2.3080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8201    0.4204   -1.3852 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2871   -1.3107   -0.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0435   -0.3454   -1.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5339   -0.1395   -0.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3136    0.7257    0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8638    1.7295   -0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9399    1.2493    0.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2998   -0.5546    0.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9940   -0.4824   -1.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6279    1.2519   -1.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5423   -0.0550   -1.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0231   -0.9675   -0.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9275    1.1846    1.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4028    2.0321   -0.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3626    1.3067    0.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0839   -1.0986   -0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5129   -0.0598    0.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0834   -2.5387   -1.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4501   -2.0651   -1.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0696   -3.1021    0.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0482   -0.9265    1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4839   -0.0295    0.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9798   -2.3154    1.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5183   -1.5912    0.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0168   -0.2447    2.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6575   -0.6295    2.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1593    1.7343    1.8721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6023    1.4196    1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8915    0.3714   -0.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3332    2.1121   -0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3255    1.3466    0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8037   -0.3577    0.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2902   -0.2579   -0.8134 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  1  0
  7  8  2  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
  6 33  1  0
  7 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


  Mrv1652303202019002D          

 20 19  0  0  0  0            999 V2000
 9997.2734 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9882 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7030 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.4187 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.1323 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.8479 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.5616 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.2773 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.9929 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.7065 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.4222 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.1399 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5584 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8435 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1287 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.4139 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6988 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9840 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.2671 9998.0698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9840 9999.3071    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  2  0  0  0  0
  6  7  1  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>
HMDB0005047

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC\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/h7-10H,2-6,11-17H2,1H3,(H,19,20)/b8-7+,10-9+

> <INCHI_KEY>
JBYXPOFIGCOSSB-XBLVEGMJSA-N

> <FORMULA>
C18H32O2

> <MOLECULAR_WEIGHT>
280.4455

> <EXACT_MASS>
280.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
37.12451304490827

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9E,11E)-octadeca-9,11-dienoic acid

> <ALOGPS_LOGP>
7.11

> <JCHEM_LOGP>
6.421876794333333

> <ALOGPS_LOGS>
-6.28

> <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>
88.51879999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.48e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9E,11E-octadecadienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005047
     RDKit          3D
(9E,11E)-Octadecadienoic acid
 52 51  0  0  0  0  0  0  0  0999 V2000
    8.4530   -0.3270   -0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8062    0.7546   -0.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3455    0.4300    0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5782    0.3435   -1.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1299    0.0150   -0.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4442    1.0500    0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0285    0.6626    0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4639   -0.4308   -0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0563   -0.7397    0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4896   -1.8286   -0.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9231   -2.0941   -0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5337   -1.0197    0.7119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9907   -1.3727    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6503   -0.3171    1.8243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6303    1.0359    1.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3410    1.0803   -0.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7928    0.6898    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4831    0.7380   -1.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8371    1.0723   -2.3080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8201    0.4204   -1.3852 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2871   -1.3107   -0.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0435   -0.3454   -1.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5339   -0.1395   -0.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3136    0.7257    0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8638    1.7295   -0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9399    1.2493    0.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2998   -0.5546    0.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9940   -0.4824   -1.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6279    1.2519   -1.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5423   -0.0550   -1.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0231   -0.9675   -0.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9275    1.1846    1.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4028    2.0321   -0.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3626    1.3067    0.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0839   -1.0986   -0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5129   -0.0598    0.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0834   -2.5387   -1.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4501   -2.0651   -1.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0696   -3.1021    0.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0482   -0.9265    1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4839   -0.0295    0.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9798   -2.3154    1.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5183   -1.5912    0.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0168   -0.2447    2.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6575   -0.6295    2.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1593    1.7343    1.8721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6023    1.4196    1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8915    0.3714   -0.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3332    2.1121   -0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3255    1.3466    0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8037   -0.3577    0.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2902   -0.2579   -0.8134 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  1  0
  7  8  2  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
  6 33  1  0
  7 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                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0    8661.5778663.832   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.9118663.064   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8664.2468663.832   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8665.5828663.064   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8666.9148663.832   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8668.2498663.064   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8669.5828663.832   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8670.9188663.064   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8672.2538663.832   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8673.5858663.064   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8674.9218663.832   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8676.2618663.064   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8660.2428663.064   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8658.9088663.832   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8657.5748663.064   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8656.2398663.832   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8654.9048663.064   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8653.5708663.832   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8652.2328663.064   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0    8653.5708665.373   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    HMDB0005047
HETATM    1  C1  UNL     1       8.453  -0.327  -0.868  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.806   0.755  -0.008  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.346   0.430   0.225  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.578   0.344  -1.050  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.130   0.015  -0.784  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.444   1.050   0.072  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.029   0.663   0.288  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.464  -0.431  -0.203  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.056  -0.740   0.059  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.490  -1.829  -0.435  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.923  -2.094  -0.139  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.534  -1.020   0.712  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.991  -1.373   0.969  1.00  0.00           C  
HETATM   14  C14 UNL     1      -4.650  -0.317   1.824  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.630   1.036   1.194  1.00  0.00           C  
HETATM   16  C16 UNL     1      -5.341   1.080  -0.131  1.00  0.00           C  
HETATM   17  C17 UNL     1      -6.793   0.690   0.030  1.00  0.00           C  
HETATM   18  C18 UNL     1      -7.483   0.738  -1.283  1.00  0.00           C  
HETATM   19  O1  UNL     1      -6.837   1.072  -2.308  1.00  0.00           O  
HETATM   20  O2  UNL     1      -8.820   0.420  -1.385  1.00  0.00           O  
HETATM   21  H1  UNL     1       8.287  -1.311  -0.388  1.00  0.00           H  
HETATM   22  H2  UNL     1       8.043  -0.345  -1.890  1.00  0.00           H  
HETATM   23  H3  UNL     1       9.534  -0.139  -0.928  1.00  0.00           H  
HETATM   24  H4  UNL     1       8.314   0.726   0.970  1.00  0.00           H  
HETATM   25  H5  UNL     1       7.864   1.729  -0.517  1.00  0.00           H  
HETATM   26  H6  UNL     1       5.940   1.249   0.854  1.00  0.00           H  
HETATM   27  H7  UNL     1       6.300  -0.555   0.730  1.00  0.00           H  
HETATM   28  H8  UNL     1       5.994  -0.482  -1.653  1.00  0.00           H  
HETATM   29  H9  UNL     1       5.628   1.252  -1.666  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.542  -0.055  -1.728  1.00  0.00           H  
HETATM   31  H11 UNL     1       4.023  -0.968  -0.271  1.00  0.00           H  
HETATM   32  H12 UNL     1       3.927   1.185   1.063  1.00  0.00           H  
HETATM   33  H13 UNL     1       3.403   2.032  -0.482  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.363   1.307   0.897  1.00  0.00           H  
HETATM   35  H15 UNL     1       2.084  -1.099  -0.811  1.00  0.00           H  
HETATM   36  H16 UNL     1      -0.513  -0.060   0.660  1.00  0.00           H  
HETATM   37  H17 UNL     1       0.083  -2.539  -1.054  1.00  0.00           H  
HETATM   38  H18 UNL     1      -2.450  -2.065  -1.138  1.00  0.00           H  
HETATM   39  H19 UNL     1      -2.070  -3.102   0.245  1.00  0.00           H  
HETATM   40  H20 UNL     1      -2.048  -0.927   1.703  1.00  0.00           H  
HETATM   41  H21 UNL     1      -2.484  -0.029   0.187  1.00  0.00           H  
HETATM   42  H22 UNL     1      -3.980  -2.315   1.576  1.00  0.00           H  
HETATM   43  H23 UNL     1      -4.518  -1.591   0.044  1.00  0.00           H  
HETATM   44  H24 UNL     1      -4.017  -0.245   2.756  1.00  0.00           H  
HETATM   45  H25 UNL     1      -5.658  -0.629   2.096  1.00  0.00           H  
HETATM   46  H26 UNL     1      -5.159   1.734   1.872  1.00  0.00           H  
HETATM   47  H27 UNL     1      -3.602   1.420   1.087  1.00  0.00           H  
HETATM   48  H28 UNL     1      -4.892   0.371  -0.842  1.00  0.00           H  
HETATM   49  H29 UNL     1      -5.333   2.112  -0.534  1.00  0.00           H  
HETATM   50  H30 UNL     1      -7.326   1.347   0.765  1.00  0.00           H  
HETATM   51  H31 UNL     1      -6.804  -0.358   0.432  1.00  0.00           H  
HETATM   52  H32 UNL     1      -9.290  -0.258  -0.813  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   32   33
CONECT    7    8    8   34
CONECT    8    9   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

HMDB0005047
     RDKit          3D
(9E,11E)-Octadecadienoic acid
 52 51  0  0  0  0  0  0  0  0999 V2000
    8.4530   -0.3270   -0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8062    0.7546   -0.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3455    0.4300    0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5782    0.3435   -1.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1299    0.0150   -0.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4442    1.0500    0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0285    0.6626    0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4639   -0.4308   -0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0563   -0.7397    0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4896   -1.8286   -0.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9231   -2.0941   -0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5337   -1.0197    0.7119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9907   -1.3727    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6503   -0.3171    1.8243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6303    1.0359    1.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3410    1.0803   -0.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7928    0.6898    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4831    0.7380   -1.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8371    1.0723   -2.3080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8201    0.4204   -1.3852 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2871   -1.3107   -0.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0435   -0.3454   -1.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5339   -0.1395   -0.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3136    0.7257    0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8638    1.7295   -0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9399    1.2493    0.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2998   -0.5546    0.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9940   -0.4824   -1.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6279    1.2519   -1.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5423   -0.0550   -1.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0231   -0.9675   -0.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9275    1.1846    1.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4028    2.0321   -0.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3626    1.3067    0.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0839   -1.0986   -0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5129   -0.0598    0.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0834   -2.5387   -1.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4501   -2.0651   -1.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0696   -3.1021    0.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0482   -0.9265    1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4839   -0.0295    0.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9798   -2.3154    1.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5183   -1.5912    0.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0168   -0.2447    2.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6575   -0.6295    2.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1593    1.7343    1.8721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6023    1.4196    1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8915    0.3714   -0.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3332    2.1121   -0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3255    1.3466    0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8037   -0.3577    0.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2902   -0.2579   -0.8134 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  1  0
  7  8  2  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
  6 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 20 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(9E,11E)-9,11-Octadecadienoic acid	ChEBI
(e,e)-9,11-Octadecadienoic acid	ChEBI
(e,e)-Isolinoleic acid	ChEBI
9-trans, 11-trans-CLA	ChEBI
9-trans,11-trans-Conjugated linoleic acid	ChEBI
9-trans,11-trans-Octadecadienoic acid	ChEBI
9E,11E-CLA	ChEBI
9t,11t-CLA	ChEBI
Conjugated (9E,11E)-linoleic acid	ChEBI
Isolinoleic acid	ChEBI
Mangold's acid	ChEBI
trans,trans-9,11-Octadecadienoic acid	ChEBI
trans-9, trans-11-Octadecadienoic acid	ChEBI
(9E,11E)-9,11-Octadecadienoate	Generator
(e,e)-9,11-Octadecadienoate	Generator
(e,e)-Isolinoleate	Generator
9-trans,11-trans-Conjugated linoleate	Generator
9-trans,11-trans-Octadecadienoate	Generator
Conjugated (9E,11E)-linoleate	Generator
Isolinoleate	Generator
trans,trans-9,11-Octadecadienoate	Generator
trans-9, trans-11-Octadecadienoate	Generator
(9E,11E)-Octadecadienoate	Generator
9,11-Linoleic acid	HMDB, MeSH
CLA 80	HMDB
Conjugated linoleic acid	HMDB
delta9,11-Octadecadienoate	HMDB
Nouracid de 554	HMDB
Ricineic acid	HMDB
Ricinenic acid	HMDB
Selin cla	HMDB
9,11-Linoleic acid, (E,E)-isomer	MeSH, HMDB
9,11-Isolinoleic acid	MeSH, HMDB
Octadeca-9,11-dienoic acid	MeSH, HMDB
9,11-Octadecadienoate	MeSH, HMDB
(9E,11E)-Octadecadienoic acid	HMDB
9,11-Conjugated linoleic acid	HMDB
9-trans,11-trans-Linoleic acid	HMDB
9E,11E-Octadecadienoic acid	HMDB
FA(18:2(9E,11E))	HMDB
delta9,11-Octadecadienoic acid	HMDB
trans-11-trans-9-Octadecadienoic acid	HMDB
trans-9,trans-11 Conjugated linoleic acid	HMDB
trans-9,trans-11-Octadecadienoic acid	HMDB
Δ9,11-Octadecadienoic acid	HMDB
9E,11E-Octadecadienoate	Generator
10E,12Z-Octadecadienoate	Generator

Chemical Formula

C₁₈H₃₂O₂

Average Molecular Weight

280.4455

Monoisotopic Molecular Weight

280.240230268

IUPAC Name

(9E,11E)-octadeca-9,11-dienoic acid

Traditional Name

9E,11E-octadecadienoic acid

CAS Registry Number

1839-11-8

SMILES

CCCCCC\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/h7-10H,2-6,11-17H2,1H3,(H,19,20)/b8-7+,10-9+

InChI Key

JBYXPOFIGCOSSB-XBLVEGMJSA-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

Unsaturated fatty acids (LMFA01030119 )

Ontology

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00015 g/L	ALOGPS
logP	7.11	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	37.12 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	176.5	31661259
DarkChem	[M-H]-	177.268	31661259
DeepCCS	[M+H]+	177.003	30932474
DeepCCS	[M-H]-	172.983	30932474
DeepCCS	[M-2H]-	209.645	30932474
DeepCCS	[M+Na]+	185.818	30932474
AllCCS	[M+H]+	177.3	32859911
AllCCS	[M+H-H2O]+	174.3	32859911
AllCCS	[M+NH4]+	180.2	32859911
AllCCS	[M+Na]+	181.0	32859911
AllCCS	[M-H]-	178.4	32859911
AllCCS	[M+Na-2H]-	180.0	32859911
AllCCS	[M+HCOO]-	181.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	9.88 minutes	32390414
Predicted by Siyang on May 30, 2022	25.1428 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.77 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	36.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3134.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	708.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	271.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	447.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	629.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1102.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	748.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	91.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2324.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	697.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1875.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	871.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	545.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	648.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	654.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(9E,11E)-Octadecadienoic acid	CCCCCC\C=C\C=C\CCCCCCCC(O)=O	3441.4	Standard polar	33892256
(9E,11E)-Octadecadienoic acid	CCCCCC\C=C\C=C\CCCCCCCC(O)=O	2165.5	Standard non polar	33892256
(9E,11E)-Octadecadienoic acid	CCCCCC\C=C\C=C\CCCCCCCC(O)=O	2217.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(9E,11E)-Octadecadienoic acid,1TMS,isomer #1	CCCCCC/C=C/C=C/CCCCCCCC(=O)O[Si](C)(C)C	2290.0	Semi standard non polar	33892256
(9E,11E)-Octadecadienoic acid,1TBDMS,isomer #1	CCCCCC/C=C/C=C/CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2526.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (9E,11E)-Octadecadienoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9550000000-f91f775c11691e572339	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (9E,11E)-Octadecadienoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0079-9531000000-ff0f0a6283e777000b03	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (9E,11E)-Octadecadienoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid ESI-TOF 20V, Negative-QTOF	splash10-004i-0090000000-d3517fc9c425686f3f47	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid ESI-TOF 10V, Negative-QTOF	splash10-004i-0090000000-dfad2b4819a8e09aeb74	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid ESI-TOF 10V, Negative-QTOF	splash10-004i-0093020000-3713e3e16e9fc8ff9d4e	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid ESI-TOF 30V, Negative-QTOF	splash10-004i-0090000000-1ab95baf25a47f7edbbe	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid ESI-TOF , Negative-QTOF	splash10-004i-0091000000-88b67552039f5c14c7ea	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid LC-ESI-TOF , negative-QTOF	splash10-004i-0090000000-d3517fc9c425686f3f47	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid LC-ESI-TOF , negative-QTOF	splash10-004i-0090000000-dfad2b4819a8e09aeb74	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid LC-ESI-TOF , negative-QTOF	splash10-004i-0090000000-1ab95baf25a47f7edbbe	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 20V, Positive-QTOF	splash10-004i-0090000000-d3517fc9c425686f3f47	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 10V, Positive-QTOF	splash10-004i-0090000000-dfad2b4819a8e09aeb74	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 30V, Positive-QTOF	splash10-004i-0090000000-1ab95baf25a47f7edbbe	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 10V, Positive-QTOF	splash10-03di-0090000000-f2c6c9de24118516f0db	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 20V, Positive-QTOF	splash10-022j-5690000000-f4c090f44fe34f660b19	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 40V, Positive-QTOF	splash10-006x-9830000000-42ee75da80e6ee682b90	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 10V, Negative-QTOF	splash10-004i-0090000000-f1e9e4b543f7d4f48bf8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 20V, Negative-QTOF	splash10-01ti-0090000000-665523c6142ff4e39c96	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 40V, Negative-QTOF	splash10-0a4l-9230000000-b43315d97b9995f922a3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 10V, Positive-QTOF	splash10-01qa-5590000000-6740409ad0ee9d0c387c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 20V, Positive-QTOF	splash10-05mk-9510000000-78bd3b0ecfca1dab2bac	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 40V, Positive-QTOF	splash10-0apm-9000000000-98f6af2debd76c0c3c6e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 10V, Negative-QTOF	splash10-004i-0090000000-03fd7d53d39127d02766	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 20V, Negative-QTOF	splash10-01t9-1090000000-c03baa3d5c1c48e8c45c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (9E,11E)-Octadecadienoic acid 40V, Negative-QTOF	splash10-0006-9310000000-07f427d77d98dab09f40	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	19.3 +/- 3.9 uM	Adult (>18 years old)	Both	Normal	2975566	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	25.3 +/- 1.1 uM	Adult (>18 years old)	Both	Lipid peroxidation	4075442	details
Blood	Detected and Quantified	24.0 +/- 11.0 uM	Adult (>18 years old)	Both	Primary biliary Cirrhosis	2882386	details

Associated Disorders and Diseases

Disease References

Lipid peroxidation
Thompson S, Smith MT: Measurement of the diene conjugated form of linoleic acid in plasma by high performance liquid chromatography: a questionable non-invasive assay of free radical activity? Chem Biol Interact. 1985 Nov;55(3):357-66. [PubMed:4075442 ]
Primary biliary cirrhosis
Braganza JM, Day JP: Serum octadeca-9-11 dienoic acid concentrations in primary biliary cirrhosis. Lancet. 1987 Apr 25;1(8539):987. [PubMed:2882386 ]

Associated OMIM IDs

109720 (Primary biliary cirrhosis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023610

KNApSAcK ID

C00053367

Chemspider ID

4445923

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282796

PDB ID

Not Available

ChEBI ID

88464

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Priester, Remmet. 9,11-Octadecadienoic acid. (1939), US 2156737 19390502 CAN 33:44507 AN 1939:44507

Material Safety Data Sheet (MSDS)

Not Available

General References

Toomey S, McMonagle J, Roche HM: Conjugated linoleic acid: a functional nutrient in the different pathophysiological components of the metabolic syndrome? Curr Opin Clin Nutr Metab Care. 2006 Nov;9(6):740-7. [PubMed:17053429 ]
Navarro V, Fernandez-Quintela A, Churruca I, Portillo MP: The body fat-lowering effect of conjugated linoleic acid: a comparison between animal and human studies. J Physiol Biochem. 2006 Jun;62(2):137-47. [PubMed:17217167 ]
Tvrzicka E, Vecka M, Zak A: [Conjugated linoleic acid--the dietary supplement in the prevention of cardiovascular diseases]. Cas Lek Cesk. 2007;146(5):459-65. [PubMed:17554969 ]
Tricon S, Yaqoob P: Conjugated linoleic acid and human health: a critical evaluation of the evidence. Curr Opin Clin Nutr Metab Care. 2006 Mar;9(2):105-10. [PubMed:16477173 ]

Showing metabocard for (9E,11E)-Octadecadienoic acid (HMDB0005047)

MOL for HMDB0005047 ((9E,11E)-Octadecadienoic acid)

3D MOL for HMDB0005047 ((9E,11E)-Octadecadienoic acid)

3D SDF for HMDB0005047 ((9E,11E)-Octadecadienoic acid)

3D-SDF for HMDB0005047 ((9E,11E)-Octadecadienoic acid)

PDB for HMDB0005047 ((9E,11E)-Octadecadienoic acid)

3D PDB for HMDB0005047 ((9E,11E)-Octadecadienoic acid)

SMILES for HMDB0005047 ((9E,11E)-Octadecadienoic acid)

INCHI for HMDB0005047 ((9E,11E)-Octadecadienoic acid)

Structure for HMDB0005047 ((9E,11E)-Octadecadienoic acid)

3D Structure for HMDB0005047 ((9E,11E)-Octadecadienoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra