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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:02 UTC

HMDB ID

HMDB0000477

Secondary Accession Numbers

HMDB00477

Metabolite Identification

Common Name

7Z,10Z-Hexadecadienoic acid

Description

7Z,10Z-Hexadecadienoic acid is a conjugated dienoic fatty acid metabolite of conjugated linoleic acid (CLA). CLAs are a naturally occurring group of positional and geometric isomers of linoleic acid, with potential beneficial effects on atherosclerosis, carcinogenesis or obesity in human. Although the molecular mechanisms are largely unknown, it has been proposed that the anti-atherogenic actions comprise reduction of membrane-bound arachidonic acid and peroxisome proliferator-activated receptor (PPAR)-γ-dependent inhibition of Nuclear Factor kappa B (NF-κB) activation and subsequently reduced prostanoid release. (PMID 16275160 ).

Structure

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

HMDB0000477
     RDKit          3D
7Z,10Z-Hexadecadienoic acid
 46 45  0  0  0  0  0  0  0  0999 V2000
    3.5919    1.7130    1.7910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5869    0.6208    1.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1696   -0.6886    1.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0082   -0.8381    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4213   -0.5696   -1.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9930    0.8026   -1.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7910    1.1580   -1.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6367    0.4046   -2.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934   -0.9965   -2.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2819   -1.7504   -1.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1421   -1.3132   -0.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5883   -1.6888   -0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5651   -1.3014    0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6220    0.1596    0.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6560    0.4278    1.8100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7315    1.8797    2.1202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5443    2.2444    2.9973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9573    2.8308    1.4943 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3386    2.2595    2.7177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849    2.4954    0.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6351    1.3547    1.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7452    0.9943    1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417    0.4469    2.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7790   -1.0419    2.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3087   -1.4338    1.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3589   -1.9258   -0.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9621   -0.2448    0.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6774   -1.3697   -1.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3155   -0.7885   -2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7855    1.6028   -1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484    2.2854   -1.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1507    0.8387   -3.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1784    0.7783   -1.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0257   -1.5482   -2.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2945   -2.8435   -1.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1438   -0.2683   -0.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929   -1.9844    0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8699   -1.1137   -1.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840   -2.7420   -0.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5691   -1.6121    0.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4047   -1.8319    1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9518    0.7596   -0.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6542    0.5638    1.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4067   -0.1808    2.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6408    0.0681    1.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2699    3.3870    0.7043 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  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 18 46  1  0
M  END

7Z,10Z-Hexadecadienoic acid.mol
  Mrv0541 02231218322D          

 18 17  0  0  0  0            999 V2000
    2.2687    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6813   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2687   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4437   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312   -1.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2063   -1.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063   -2.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0312   -2.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4438   -1.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688   -1.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6813   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6813    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688    1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6813    1.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688    2.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4437    0.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6812    1.0717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  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
  1 17  2  0  0  0  0
  1 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000477

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h6-7,9-10H,2-5,8,11-15H2,1H3,(H,17,18)/b7-6-,10-9-

> <INCHI_KEY>
WPJGPAAPSBVXNU-HZJYTTRNSA-N

> <FORMULA>
C16H28O2

> <MOLECULAR_WEIGHT>
252.3923

> <EXACT_MASS>
252.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
31.67223267358412

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(7Z,10Z)-hexadeca-7,10-dienoic acid

> <ALOGPS_LOGP>
6.23

> <JCHEM_LOGP>
5.532739464333334

> <ALOGPS_LOGS>
-5.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.955292438746737

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
79.3168

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.67e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7Z,10Z-hexadecadienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000477
     RDKit          3D
7Z,10Z-Hexadecadienoic acid
 46 45  0  0  0  0  0  0  0  0999 V2000
    3.5919    1.7130    1.7910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5869    0.6208    1.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1696   -0.6886    1.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0082   -0.8381    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4213   -0.5696   -1.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9930    0.8026   -1.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7910    1.1580   -1.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6367    0.4046   -2.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934   -0.9965   -2.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2819   -1.7504   -1.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1421   -1.3132   -0.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5883   -1.6888   -0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5651   -1.3014    0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6220    0.1596    0.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6560    0.4278    1.8100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7315    1.8797    2.1202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5443    2.2444    2.9973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9573    2.8308    1.4943 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3386    2.2595    2.7177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849    2.4954    0.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6351    1.3547    1.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7452    0.9943    1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417    0.4469    2.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7790   -1.0419    2.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3087   -1.4338    1.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3589   -1.9258   -0.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9621   -0.2448    0.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6774   -1.3697   -1.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3155   -0.7885   -2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7855    1.6028   -1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484    2.2854   -1.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1507    0.8387   -3.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1784    0.7783   -1.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0257   -1.5482   -2.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2945   -2.8435   -1.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1438   -0.2683   -0.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929   -1.9844    0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8699   -1.1137   -1.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840   -2.7420   -0.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5691   -1.6121    0.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4047   -1.8319    1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9518    0.7596   -0.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6542    0.5638    1.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4067   -0.1808    2.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6408    0.0681    1.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2699    3.3870    0.7043 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  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 18 46  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 7Z,10Z-Hexadecadienoic acid.mol                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       4.235   0.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.005  -0.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.235  -2.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.695  -2.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.925  -3.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.385  -3.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.385  -4.668   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.925  -4.668   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.695  -3.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.235  -3.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.005  -2.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.235  -0.667   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.005   0.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.235   2.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.005   3.334   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.235   4.668   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.695   0.667   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.005   2.001   0.000  0.00  0.00           O+0
CONECT    1    2   17   18                                                  
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   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0000477
HETATM    1  C1  UNL     1       3.592   1.713   1.791  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.587   0.621   1.574  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.170  -0.689   1.218  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.008  -0.838   0.032  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.421  -0.570  -1.335  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.993   0.803  -1.416  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.791   1.158  -1.711  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.637   0.405  -2.021  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.493  -0.997  -2.142  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.282  -1.750  -1.383  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.142  -1.313  -0.274  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.588  -1.689  -0.621  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.565  -1.301   0.433  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.622   0.160   0.726  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.656   0.428   1.810  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.732   1.880   2.120  1.00  0.00           C  
HETATM   17  O1  UNL     1      -5.544   2.244   2.997  1.00  0.00           O  
HETATM   18  O2  UNL     1      -3.957   2.831   1.494  1.00  0.00           O  
HETATM   19  H1  UNL     1       3.339   2.260   2.718  1.00  0.00           H  
HETATM   20  H2  UNL     1       3.485   2.495   0.981  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.635   1.355   1.861  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.745   0.994   1.009  1.00  0.00           H  
HETATM   23  H5  UNL     1       2.142   0.447   2.633  1.00  0.00           H  
HETATM   24  H6  UNL     1       3.779  -1.042   2.117  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.309  -1.434   1.236  1.00  0.00           H  
HETATM   26  H8  UNL     1       4.359  -1.926  -0.040  1.00  0.00           H  
HETATM   27  H9  UNL     1       4.962  -0.245   0.103  1.00  0.00           H  
HETATM   28  H10 UNL     1       2.677  -1.370  -1.434  1.00  0.00           H  
HETATM   29  H11 UNL     1       4.315  -0.789  -2.018  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.785   1.603  -1.205  1.00  0.00           H  
HETATM   31  H13 UNL     1       1.648   2.285  -1.721  1.00  0.00           H  
HETATM   32  H14 UNL     1       0.151   0.839  -3.004  1.00  0.00           H  
HETATM   33  H15 UNL     1      -0.178   0.778  -1.298  1.00  0.00           H  
HETATM   34  H16 UNL     1       1.026  -1.548  -2.940  1.00  0.00           H  
HETATM   35  H17 UNL     1      -0.294  -2.843  -1.595  1.00  0.00           H  
HETATM   36  H18 UNL     1      -1.144  -0.268  -0.011  1.00  0.00           H  
HETATM   37  H19 UNL     1      -0.893  -1.984   0.595  1.00  0.00           H  
HETATM   38  H20 UNL     1      -2.870  -1.114  -1.552  1.00  0.00           H  
HETATM   39  H21 UNL     1      -2.684  -2.742  -0.880  1.00  0.00           H  
HETATM   40  H22 UNL     1      -4.569  -1.612   0.074  1.00  0.00           H  
HETATM   41  H23 UNL     1      -3.405  -1.832   1.395  1.00  0.00           H  
HETATM   42  H24 UNL     1      -3.952   0.760  -0.163  1.00  0.00           H  
HETATM   43  H25 UNL     1      -2.654   0.564   1.028  1.00  0.00           H  
HETATM   44  H26 UNL     1      -4.407  -0.181   2.720  1.00  0.00           H  
HETATM   45  H27 UNL     1      -5.641   0.068   1.468  1.00  0.00           H  
HETATM   46  H28 UNL     1      -4.270   3.387   0.704  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   28   29
CONECT    6    7    7   30
CONECT    7    8   31
CONECT    8    9   32   33
CONECT    9   10   10   34
CONECT   10   11   35
CONECT   11   12   36   37
CONECT   12   13   38   39
CONECT   13   14   40   41
CONECT   14   15   42   43
CONECT   15   16   44   45
CONECT   16   17   17   18
CONECT   18   46
END

HMDB0000477
     RDKit          3D
7Z,10Z-Hexadecadienoic acid
 46 45  0  0  0  0  0  0  0  0999 V2000
    3.5919    1.7130    1.7910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5869    0.6208    1.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1696   -0.6886    1.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0082   -0.8381    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4213   -0.5696   -1.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9930    0.8026   -1.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7910    1.1580   -1.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6367    0.4046   -2.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934   -0.9965   -2.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2819   -1.7504   -1.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1421   -1.3132   -0.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5883   -1.6888   -0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5651   -1.3014    0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6220    0.1596    0.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6560    0.4278    1.8100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7315    1.8797    2.1202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5443    2.2444    2.9973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9573    2.8308    1.4943 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3386    2.2595    2.7177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849    2.4954    0.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6351    1.3547    1.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7452    0.9943    1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417    0.4469    2.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7790   -1.0419    2.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3087   -1.4338    1.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3589   -1.9258   -0.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9621   -0.2448    0.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6774   -1.3697   -1.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3155   -0.7885   -2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7855    1.6028   -1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484    2.2854   -1.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1507    0.8387   -3.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1784    0.7783   -1.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0257   -1.5482   -2.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2945   -2.8435   -1.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1438   -0.2683   -0.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929   -1.9844    0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8699   -1.1137   -1.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840   -2.7420   -0.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5691   -1.6121    0.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4047   -1.8319    1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9518    0.7596   -0.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6542    0.5638    1.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4067   -0.1808    2.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6408    0.0681    1.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2699    3.3870    0.7043 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  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 18 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Z,Z)-7,10-Hexadecadienoic acid	ChEBI
(Z,Z)-Hexadeca-7,10-dienoic acid	ChEBI
7-cis,10-cis-Hexadecadienoic acid	ChEBI
C16:2N-6,9	ChEBI
(Z,Z)-7,10-Hexadecadienoate	Generator
(Z,Z)-Hexadeca-7,10-dienoate	Generator
7-cis,10-cis-Hexadecadienoate	Generator
7Z,10Z-Hexadecadienoate	Generator
(7Z,10Z)-Hexadecadienoate	HMDB
7Z,10Z-Hexadecadienoic acid	ChEBI

Chemical Formula

C₁₆H₂₈O₂

Average Molecular Weight

252.3923

Monoisotopic Molecular Weight

252.20893014

IUPAC Name

(7Z,10Z)-hexadeca-7,10-dienoic acid

Traditional Name

7Z,10Z-hexadecadienoic acid

CAS Registry Number

28290-73-5

SMILES

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

InChI Identifier

InChI=1S/C16H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h6-7,9-10H,2-5,8,11-15H2,1H3,(H,17,18)/b7-6-,10-9-

InChI Key

WPJGPAAPSBVXNU-HZJYTTRNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

hexadecadienoic acid (CHEBI:86147 )
Unsaturated fatty acids (LMFA01030807 )

Ontology

Not Available

Physical Properties

State

Solid

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	0.00067 g/L	ALOGPS
logP	6.23	ALOGPS
logP	5.53	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	4.96	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	12	ChemAxon
Refractivity	79.32 m³·mol⁻¹	ChemAxon
Polarizability	31.67 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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]+	170.653	31661259
DarkChem	[M-H]-	169.79	31661259
AllCCS	[M+H]+	168.127	32859911
AllCCS	[M-H]-	170.202	32859911
DeepCCS	[M+H]+	172.283	30932474
DeepCCS	[M-H]-	168.263	30932474
DeepCCS	[M-2H]-	205.089	30932474
DeepCCS	[M+Na]+	181.098	30932474
AllCCS	[M+H]+	168.1	32859911
AllCCS	[M+H-H2O]+	164.8	32859911
AllCCS	[M+NH4]+	171.2	32859911
AllCCS	[M+Na]+	172.1	32859911
AllCCS	[M-H]-	170.2	32859911
AllCCS	[M+Na-2H]-	171.5	32859911
AllCCS	[M+HCOO]-	173.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7Z,10Z-Hexadecadienoic acid	CCCCC\C=C/C\C=C/CCCCCC(O)=O	3044.6	Standard polar	33892256
7Z,10Z-Hexadecadienoic acid	CCCCC\C=C/C\C=C/CCCCCC(O)=O	1876.1	Standard non polar	33892256
7Z,10Z-Hexadecadienoic acid	CCCCC\C=C/C\C=C/CCCCCC(O)=O	1945.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7Z,10Z-Hexadecadienoic acid,1TMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCC(=O)O[Si](C)(C)C	2017.4	Semi standard non polar	33892256
7Z,10Z-Hexadecadienoic acid,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCC(=O)O[Si](C)(C)C(C)(C)C	2255.1	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 - 7Z,10Z-Hexadecadienoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-7910000000-7b6ef798284664078588	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7Z,10Z-Hexadecadienoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-05g0-9630000000-4019881c64a2f6c89037	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7Z,10Z-Hexadecadienoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7Z,10Z-Hexadecadienoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7Z,10Z-Hexadecadienoic acid 10V, Positive-QTOF	splash10-000i-0090000000-05769e9022511fa4a57a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7Z,10Z-Hexadecadienoic acid 20V, Positive-QTOF	splash10-0acc-6980000000-bec20c540e3f64027411	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7Z,10Z-Hexadecadienoic acid 40V, Positive-QTOF	splash10-052f-9700000000-ed1ece5105820ceae10c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7Z,10Z-Hexadecadienoic acid 10V, Negative-QTOF	splash10-0udi-0090000000-101b1f2a083eac50d3d7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7Z,10Z-Hexadecadienoic acid 20V, Negative-QTOF	splash10-0zgi-0090000000-21ebd490f19df758cd1d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7Z,10Z-Hexadecadienoic acid 40V, Negative-QTOF	splash10-0a4l-9320000000-69bc9ee2cd3db4847b1b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7Z,10Z-Hexadecadienoic acid 10V, Positive-QTOF	splash10-0uei-7690000000-11a2a56977ed2a984e1a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7Z,10Z-Hexadecadienoic acid 20V, Positive-QTOF	splash10-05o1-9200000000-5749042899575d74edc6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7Z,10Z-Hexadecadienoic acid 40V, Positive-QTOF	splash10-05o4-9000000000-9378c729c4309f3d78c7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7Z,10Z-Hexadecadienoic acid 10V, Negative-QTOF	splash10-0udi-0090000000-defe05133d0afa7c26fb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7Z,10Z-Hexadecadienoic acid 20V, Negative-QTOF	splash10-0ue9-1090000000-ec083e41e9e5ca5b24ed	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7Z,10Z-Hexadecadienoic acid 40V, Negative-QTOF	splash10-0006-9300000000-6690d743c0c10a9151c2	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohns disease	26848182	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Iron deficiency	26848182	details

Associated Disorders and Diseases

Disease References

Crohn's disease
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Iron deficiency
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]

Associated OMIM IDs

266600 (Crohn's disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022066

KNApSAcK ID

Not Available

Chemspider ID

13628094

KEGG Compound ID

Not Available

BioCyc ID

CPD-17290

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5464

PubChem Compound

13932172

PDB ID

Not Available

ChEBI ID

86147

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Beaudoin, Adrien; Martin, Genevieve. Method of extracting lipids from marine and aquatic animal tissues. PCT Int. Appl. (2000), 58 pp. CODEN: PIXXD2 WO 2000023546 A1 20000427 CAN 132:305471 AN 2000:278070

Material Safety Data Sheet (MSDS)

Not Available

General References

Muller A, Ringseis R, Dusterloh K, Gahler S, Eder K, Steinhart H: Detection of conjugated dienoic fatty acids in human vascular smooth muscle cells treated with conjugated linoleic acid. Biochim Biophys Acta. 2005 Dec 15;1737(2-3):145-51. Epub 2005 Oct 21. [PubMed:16275160 ]

Showing metabocard for 7Z,10Z-Hexadecadienoic acid (HMDB0000477)

MOL for HMDB0000477 (7Z,10Z-Hexadecadienoic acid)

3D MOL for HMDB0000477 (7Z,10Z-Hexadecadienoic acid)

3D SDF for HMDB0000477 (7Z,10Z-Hexadecadienoic acid)

3D-SDF for HMDB0000477 (7Z,10Z-Hexadecadienoic acid)

PDB for HMDB0000477 (7Z,10Z-Hexadecadienoic acid)

3D PDB for HMDB0000477 (7Z,10Z-Hexadecadienoic acid)

SMILES for HMDB0000477 (7Z,10Z-Hexadecadienoic acid)

INCHI for HMDB0000477 (7Z,10Z-Hexadecadienoic acid)

Structure for HMDB0000477 (7Z,10Z-Hexadecadienoic acid)

3D Structure for HMDB0000477 (7Z,10Z-Hexadecadienoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra